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CN-122004238-A - Antimicrobial compositions, methods of making and uses thereof

CN122004238ACN 122004238 ACN122004238 ACN 122004238ACN-122004238-A

Abstract

The present invention relates to antimicrobial compositions, methods of making and uses thereof. The antimicrobial composition comprises at least one silver compound, at least one organic complexing agent, and one or more bases, wherein the organic complexing agent has the structure of formula I wherein R 1 is independently hydrogen, linear or branched C 1 -C 5 alkyl, or amino optionally substituted with C 1 -C 5 alkyl, R 2 is independently linear C 1 -C 5 alkylene optionally substituted with C 1 -C 5 alkyl, and R 3 is independently hydrogen, linear or branched C 1 -C 5 alkyl, or linear or branched C 2 -C 5 alkyl substituted with carboxy. When formulated into aqueous compositions, the compositions have good physical stability and even good color stability, particularly heat and/or light resistance, are aesthetically pleasing to consumers and are non-toxic and low cost, particularly useful in household care compositions, personal care compositions, and industrial cleaning compositions.

Inventors

  • LI SIYU
  • LIU XIAOCHI
  • QI JINGJUAN
  • LV SHUNING
  • WU QINGFENG

Assignees

  • 科莱恩国际有限公司

Dates

Publication Date
20260512
Application Date
20241111

Claims (20)

  1. 1. An antimicrobial composition comprising at least one silver compound, at least one organic complexing agent, and one or more bases, wherein the organic complexing agent has the structure of formula I: Wherein the method comprises the steps of R 1 is independently hydrogen, linear or branched C 1 -C 5 alkyl, or amino optionally substituted by C 1 -C 5 alkyl, and R 2 is independently linear C 1 -C 5 alkylene optionally substituted with C 1 -C 5 alkyl, preferably linear C 2 -C 5 alkylene optionally substituted with C 1 -C 5 alkyl; r 3 is independently hydrogen, linear or branched C 1 -C 5 alkyl, or linear or branched C 2 -C 5 alkyl substituted with carboxy.
  2. 2. The antimicrobial composition of claim 1, wherein the molar ratio of the silver compound to the organic complexing agent is from 1:1.5 to 1:60, preferably from 1:6 to 1:48.
  3. 3. The antimicrobial composition according to claim 1 or 2, wherein the silver compound is selected from the group consisting of silver oxide, silver halide, silver citrate, silver acetate, silver nitrate, silver carbonate, silver sulfate, silver sulfide, silver phosphate, silver benzoate, silver salicylate and mixtures thereof, preferably selected from the group consisting of silver oxide.
  4. 4. An antimicrobial composition according to any one of claims 1 to 3, wherein R 2 in formula I is independently selected from methylene, ethylene, 1, 3-propylene, 1, 4-butylene, 1, 5-pentylene, isopropylene (1, 2-propylene), 2-methyl-1, 3-propylene, 2-methyl-1, 4-butylene, 3-methyl-1, 4-butylene, 2, 3-dimethyl-1, 4-butylene, 2-ethyl-1, 4-butylene, 3-ethyl-1, 4-butylene, 2-methyl-1, 5-pentylene, 3-methyl-1, 5-pentylene, 4-methyl-1, 5-pentylene, 2-ethyl-1, 5-pentylene, 3-ethyl-1, 5-pentylene and 4-ethyl-1, 5-pentylene, R 2 is preferably selected from methylene, ethylene, 1, 2-propylene, 1, 3-propylene and 1, 4-butylene, more preferably from 1, 3-propylene and 1, 4-butylene.
  5. 5. The antimicrobial composition of any one of claims 1 to 4, wherein R 1 in formula I is independently selected from hydrogen, methyl, ethyl, propyl (n-propyl, isopropyl), butyl (n-butyl, isobutyl, sec-butyl, tert-butyl), pentyl (n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, tert-pentyl, 1, 2-dimethylpropyl, 2-ethylpropyl), amino, methylamino, dimethylamino, ethylamino, and diethylamino, preferably R 1 is hydrogen or methyl.
  6. 6. The antimicrobial composition according to any one of claims 1 to 5, wherein R 3 in formula I is independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, tert-pentyl, 1, 2-dimethylpropyl, 2-ethylpropyl, and carboxyethyl, carboxypropyl, carboxybutyl and carboxypentyl, preferably hydrogen.
  7. 7. An antimicrobial composition according to any one of claims 1 to 6, wherein the organic complexing agent is selected from the group consisting of 3-aminopropionic acid, 3-aminobutyric acid, 4-aminobutyric acid, 5-aminopentanoic acid, 6-aminocaproic acid and N-methyl-substituted derivatives thereof, N-ethyl-substituted derivatives, N-propyl-substituted derivatives, N-butyl-substituted derivatives, N-pentyl-substituted derivatives, N-carboxyethyl-substituted derivatives, N-carboxypropyl-substituted derivatives, N-carboxybutyl-substituted derivatives, N-carboxypentyl-substituted derivatives, and mixtures of these, preferably from the group consisting of 3-aminobutyric acid, 4-aminobutyric acid, 5-aminopentanoic acid, 6-aminocaproic acid and N-methyl-substituted derivatives thereof, N-carboxyethyl-substituted derivatives and mixtures of these, more preferably from the group consisting of 3-aminobutyric acid and 4-aminobutyric acid and N-methyl-substituted derivatives thereof, N-carboxyethyl-substituted derivatives and mixtures of these.
  8. 8. The antimicrobial composition according to any one of claims 1 to 7, wherein the base is selected from alkali metal hydroxides, preferably sodium hydroxide and potassium hydroxide.
  9. 9. The antimicrobial composition of any one of claims 1 to 8, wherein the antimicrobial composition comprises water.
  10. 10. Antimicrobial composition according to claim 9, wherein the pH of the composition is between 7 and 12, preferably between 8 and 12, particularly preferably between 9 and 12.
  11. 11. The antimicrobial composition according to claim 9 or 10, wherein the at least one silver compound is present in an amount of 0.01 wt.% to 2 wt.%, preferably 0.05 wt.% to 1 wt.%, particularly preferably 0.05 wt.% to 0.5 wt.%, based on the total weight of the antimicrobial composition.
  12. 12. The antimicrobial composition according to any one of claims 9 to 11, wherein the antimicrobial composition comprises 0.2 wt% to 30 wt%, preferably 0.2 wt% to 10 wt%, more preferably 0.2 wt% to 4 wt% of the at least one organic complexing agent, based on the total weight of the antimicrobial composition.
  13. 13. The antimicrobial composition according to any one of claims 9 to 12, wherein the composition comprises a free base, wherein the amount of free base is preferably less than 0.5 wt%.
  14. 14. The antimicrobial composition of any one of claims 9 to 13, wherein the antimicrobial composition comprises a silver complex formed from the reaction of the silver compound with the organic complexing agent, the organic complexing agent being a ligand in the complex.
  15. 15. The antimicrobial composition according to claim 14, wherein the antimicrobial composition is a colloidal dispersion comprising silver complex nanoparticles having a hydrodynamic diameter of less than 500nm, in particular less than 300nm.
  16. 16. The antimicrobial composition of any one of claims 1-8, wherein the antimicrobial composition is a gel or a solid.
  17. 17. An aqueous antimicrobial composition, wherein the aqueous antimicrobial composition comprises or consists of: -0.01% to 2% by weight, preferably 0.05% to 1% by weight, particularly preferably 0.05% to 0.5% by weight of a silver compound selected from silver oxides; -0.2% to 30% by weight, preferably 0.2% to 10% by weight, more preferably 0.2% to 4% by weight of at least one organic complexing agent selected from the group consisting of 3-aminobutyric acid, 4-aminobutyric acid, 5-aminopentanoic acid, 6-aminocaproic acid and mixtures thereof; -one or more bases selected from sodium hydroxide and potassium hydroxide, in such an amount as to adjust the pH of the composition between 8 and 12, preferably between 9 and 12, and -Water.
  18. 18. A method of preparing an antimicrobial composition according to any one of claims 1 to 17, comprising the step of mixing all components used to prepare the composition.
  19. 19. The method of claim 18, wherein the method is performed at room temperature or elevated temperature, such as heating to a temperature of up to 70 ℃, and the mixture reacts to form an aqueous dispersion comprising a silver complex.
  20. 20. The method of claim 18 or 19, wherein the organic complexing agent and alkali are first dissolved in water to form a solution, and then the silver compound is added to the solution.

Description

Antimicrobial compositions, methods of making and uses thereof Technical Field The present invention relates to antimicrobial compositions, in particular to an antimicrobial composition comprising a silver compound, in particular an aqueous antimicrobial composition, a process for its preparation and its use in household care compositions, personal care compositions and industrial cleaning compositions. Background Silver-containing compositions are well known as broad spectrum antimicrobial agents for general use in medical and daily care products. However, high levels of silver compounds in aqueous form, even for chelation of silver ions, are prone to destabilization upon exposure to alkaline conditions, heat and light, such as significant discoloration of the solution, e.g., yellowing, reddening, even to tan or even to produce brown, gray or black particles which in turn are prone to agglomeration and/or sedimentation. Poor stability not only reduces the antimicrobial efficacy of the aqueous formulation, but also gives the consumer an unpleasant aesthetic feel. In addition, most silver oxides and salts have poor solubility in water. The antimicrobial efficacy of silver-based antimicrobial agents tends to gradually decrease over time, especially in the alkaline environment of the cleaning/cleansing composition. Callicarpa willebrand von Neigri (KARL WILHELM von)) The "micro-kinetic effect" (oligodynamic effect) of silver was first described in 1893, in which silver ions and silver-based compounds exhibit powerful antimicrobial properties even at very low concentrations. Once silver ions are released from the silver metal or particles into the environment, the silver ions interact with microorganisms such as bacteria, viruses, and fungi and disrupt critical molecular structures and processes. This can lead to microbial inactivation and death. This ability of trace silver ions to exert microbiocidal effects is initially referred to as the "micro-kinetic effect" and has been used in a variety of antimicrobial applications requiring continuous microbiological control with minimum concentrations of silver compounds. US6939566B2 discloses a microbiocidal formulation comprising at least one disinfectant and a complex of the formula R-M, wherein R is at least one organic chelating moiety, M is at least one metal ion, and wherein R is present in at least equimolar amounts based on the amount of M, and M has microbiocidal effect on at least one microorganism, wherein the at least one organic chelating moiety is an amino acid, wherein the amino acid is selected to form a complex with M at a pH of 2 or less, wherein the amino acid comprises double bond oxygen, wherein the double bond oxygen of the amino acid complexes with M at a pH of 2 or less, and wherein the disinfectant and the complex are different, and wherein the complex is a solid in the formulation. The amino acid used is an alpha-amino acid. The formulation is preferably a concentrate in gel or solid form. In the examples, soluble silver nitrate and alpha-amino acids are used to form complexes which are insoluble precipitates that are visible to the naked eye, and hydrogen peroxide is additionally used in the formulation as a disinfectant in combination with the above complexes for preservation of flowers and plants. US8637088B2 discloses an antimicrobial composition containing soluble silver dihydrogen citrate as a source of soluble silver ions, together with complexing and chelating agents that help stabilize the silver ions, allowing antimicrobial efficacy to be maintained even at neutral or alkaline pH values. The complexing agents used are alkanolamines, such as monoethanolamine and aminoalcohols, to prevent precipitation of silver ions. In addition, alpha-amino acids such as glutamic acid or chelating agents such as EDTA may provide further silver ion stabilization. The disclosed formulations with pH values above 6 show potent antimicrobial activity. The document is silent about long-term storage stability or color stability. US10093885B2 or EP3099772B1 discloses an aqueous composition comprising a oligodynamic metal, a chelating agent, an organic acid and less than 1 wt% of a free base. Stable aqueous antimicrobial compositions can be starting from a wider source of silver compounds and exhibit good stability against precipitation, with improved red discoloration. The chelating agent is selected from ethylenediamine tetraacetic acid (EDTA), ethylenediamine disuccinate (EDDS), N-bis (carboxymethyl) glutamic acid (GLDA), diethylenetriamine pentaacetic acid (DTPA), nitrilotriacetic acid (NTA) or Ethanol Diglycine (EDG). Chelating agents are generally used in the form of their salts with metals. It was found in this document that the stability and control of the tendency to discolouration of alkaline aqueous compositions containing a micro-kinetic metal can be improved by reducing the free base content of the composition by the addition of an organic aci