US-20260123627-A1 - NATURAL OIL-BASED WATER SOLUBLE BIOCIDE

US20260123627A1US 20260123627 A1US20260123627 A1US 20260123627A1US-20260123627-A1

Abstract

A biocidal agent includes a natural oil-derived aliphatic fatty-acid chain and at least one quaternary ammonium salt moiety at one end of the natural oil-derived aliphatic fatty-acid chain. A non-ionic surfactant is bonded to each of the at least one quaternary ammonium salt moiety to form a liphophilic core with polar extremities to form a self-emulsified water-soluble biocidal agent. The synthetized green, biocompatible compound showed Log 6 reduction of Gram+, Gram−, yeast and fungus microbial organisms.

Inventors

Joseph Antoun

Assignees

FLORIDA BIOTECH, LLC

Dates

Publication Date: 20260507
Application Date: 20241105

Claims (12)

1 . A biocidal agent comprising: a natural oil-derived aliphatic fatty-acid chain; at least one quaternary ammonium salt moiety at one end of the natural oil-derived aliphatic fatty-acid chain; and a non-ionic surfactant bonded to each of the at least one quaternary ammonium salt moiety to form a liphophilic core with polar extremities to form a self-emulsified water soluble biocidal agent.
2 . The biocidal agent according to claim 1 , wherein the non-ionic surfactant includes 6 to 8 moles of ethylene oxide.
3 . The biocidal agent according to claim 1 , wherein the natural oil-derived aliphatic fatty-acid chain is a soybean oil-based aliphatic fatty-acid chain.
4 . The biocidal agent according to claim 1 , wherein the wherein the natural oil-derived aliphatic fatty-acid chain is a canola oil-based aliphatic fatty-acid chain.
5 . A biocidal agent comprising: a soybean oil-derived aliphatic fatty-acid chain; at least one quaternary ammonium salt moiety at one end of the soybean oil-derived aliphatic fatty-acid chain; and a non-ionic surfactant bonded to each of the at least one quaternary ammonium salt moiety to form a liphophilic core with polar extremities to form a self-emulsified water soluble biocidal agent.
6 . The biocidal agent according to claim 5 , wherein the non-ionic surfactant includes 6 moles of ethylene oxide.
7 . A method of producing a biocidal agent, the method comprising the steps of: providing a functionalized natural oil-derived fatty-acid derivative; providing at least one quaternary ammonium salt moiety and at least one siloxane moiety on a functionalized end of the functionalized natural oil-derived fatty acid derivative; binding a non-ionic surfactant to each of the at least one quaternary ammonium salt moiety to form a lipophilic core with polar extremities to form a self-emulsified water soluble biocidal agent.
8 . The method according to claim 7 , wherein the providing a functionalized natural oil-derived fatty-acid derivative includes providing a natural oil-derived fatty-acid and functionalizing the natural oil-derived fatty-acid.
9 . The method according to claim 8 , wherein the natural oil-derived fatty-acid is derived from soybean oil.
10 . The method according to claim 9 , wherein the functionalizing the soybean oil includes epoxidizing the soybean oil, the functionalized natural oil-derivative being epoxidized soybean oil.
11 . The method according to claim 7 , wherein the functionalizing the natural oil-derived fatty acid derivative includes at least one of amidation, transesterification, and carbonization.
12 . The method according to claim 7 , wherein the method further includes solubilizing the biocidal agent in water.

Description

TECHNICAL FIELD The present disclosure relates generally to biocides, and more particularly to a biocompatible water soluble biocide. BACKGROUND Microbial infections induced through bacterial adhesion and colonization on hard non-porous surfaces of medical devices are one of the main complications of using such devices, as they can cause high rates of mortality. The creation of biofilm on material surfaces triggers these bacterial infections. Since the first synthesis of penicillin in 1928, various new antibiotics have been developed for remedying microbial infections, owing to its great bactericidal action and minimal toxicity to mammalian cells. Considering that the growth rate of new antimicrobial drugs can barely keep up with the advancement of bacterial resistance, it is becoming progressively clear that the “post-antibiotic era” is on the horizon. Annually, more than 700,000 patients pass away due to drug-resistant germs. As a result, there is a vital requirement to generate new antibacterial biomaterials to enhance bacterial selectivity and lessen antibiotic resistance. Therefore, the prevention of bacterial attachment and the subsequent formation of biofilms on these surfaces is important. Biomaterials play an essential function in disease treatment and healthcare improvement. The diversity, function, and wide variety of biomaterials employed worldwide have improved considerably in recent years. Nevertheless, the attachment of harmful microorganisms to biomaterial surfaces, leading to biofilm growth, continues to be a major issue that seriously restricts the functional use of these systems. Various strategies have been developed to reduce the exposure of medical devices to bacterial colonization, biofilm formation and infections. Traditionally, two approaches have been widely utilized to fight against microorganisms: passive defense through using fouling resistant coatings, which can prevent the initial attachment of bacteria to a material over a short period of time; and active attack via incorporation of antimicrobial agents, including polycations, nanoparticles, enzymes, and antibiotics to kill the attached bacteria. For example, work has been done to develop an antibacterial polyurethane coating from soybean oil-based polyol with built-in quaternary ammonium salt functionalities. Similar work has been conducted to prepare antibacterial waterborne polyurethanes derived from soybean oil and quaternary ammonium salts containing chain extenders and castor oil-based polyurethane coatings utilizing quaternized triethanolamine chain extenders. The application of vegetable oil-based polyurethane has also been extended to other biomedical applications such as wound dressing, cardiac patches and tissue engineering. However, several drawbacks of these strategies limit the practical application of them. Without biocidal activity, the passive defense mechanisms are only partially effective for preventing bacterial adhesion. Once the minimum number of bacteria adheres to the surface, they can quickly grow and form a stable biofilm. On the other hand, although the active attack agents effectively prevent the formation of viable biofilms on surfaces, they often require high levels of toxicity for being effective and also suffer from problems relating to their improper biocompatibility, leaching out from the surface, short periods of biocidal activity, and the development of bacterial resistance. SUMMARY Accordingly, a new generation of biobased, biocompatible, effective and reactive water soluble biocidal agents is disclosed herein. The new water soluble compounds can replace the current chlorine, hydrogen peroxide, alcohol and quaternary ammonium disinfectant molecules used in current biocidal products which show many secondary effects and have high toxicity. That is, the preparation of stable surface active biobased antibacterial/biocidal agents are described herein. Such biocidal agents can adhere effectively to bacteria while also killing all types of bacteria without concern for bacterial resistance, solving the disadvantages of the current approaches, such as increased bacterial resistance induced through impregnation of additives such as antibiotics, metallic nanoparticles, N-halamines, and quaternary ammonium salts (QAS). Moreover, in contradiction to the existing compounds, the biocidal agents described herein are biocompatible, have low toxicity, and are biodegradable, therefore having a low carbon fingerprint on the environment. As a non-limiting example, biocidal, biocompatible, water-soluble, and dispersible soybean oil-based components for various biomedical applications are disclosed. The intended biocidal materials not only have proper biocidal activity against Gram-positive bacteria, Gram negative bacteria, and fungi and yeast but will also be water soluble and could be used as a new generation of safe, green, and bio-based antimicrobial agents. For example, a water soluble siloxane cross-linke