IP Library Granted Patent US 12708117
Granted Patent B2
US 12708117 · App. 18/265,799 · Granted Aug 18, 2026

Surface antimicrobial treatments

Inventors: Valentina Beghetto (Treviso, IT); Vanessa Gatto (Treviso, IT); Silvia Conca (Treviso, IT); Noemi Bardella (Treviso, IT)
Assignee: CROSSING S.R.L.
A01N55/00A01N25/02A01N25/10A01N25/34A01N43/707A01N43/84A01P1/00
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Quick Facts
Patent No.
US 12708117
App. No.
18/265,799
Granted
Aug 18, 2026
Kind
B2
Abstract

Compositions comprising triazine quaternary ammonium salts and silane compounds, their method of preparation and use which provides for the application of the compositions to surfaces or materials of different chemical nature to which they confer antimicrobial and antifouling properties. The material obtained with the described treatment does not release antimicrobial or antifouling agents into the environment in contact, and from the surfaces or materials treated.

Claims (27)

1 . A composition comprising at least one silane compound F(I), and at least one triazine quaternary ammonium salt F(II),

wherein F(I) is (3-aminopropyl)triethoxysilane and F(II) is 4-(4,6-dichloro-1,3,5-triazin-2-yl)-4-(3-dodecanamidopropyl)morpholin-4-ium chloride; or

wherein F(I) is (3-aminopropyl) trimethoxysilane and F(II) is 1-(4-chloro-6-(dodecylamino)-1,3,5-triazin-2-yl)-3-methyl-1H-imidazole-3-ium chloride; or wherein F(I) is a mixture of triethoxy (propyl) silane and 2-(triethoxysilyl) ethan-1-ol, and F(II) is a mixture of 4-(4-chloro-6-(tetradecylamino)-1,3,5-triazin-2-yl)-4-ethylmorpholin-4-ium chloride and 4-(4-chloro-6-((3-(triethoxysilyl)propyl) amino)-1,3,5-triazin-2-yl)-4-(2-(decanoyloxy) ethyl)morpholin-4-ium chloride; or

wherein F(I) is (3-aminopropyl) triethoxysilane, and F(II) is a mixture of 4-(4,6-dichloro-1,3,5-triazin-2-yl)-4-(3-dodecanamidopropyl) morpholin-4-ium chloride and 1-(4-chloro-6-(dodecylamino)-1,3,5-triazin-2-yl)-3-methyl-1H-imidazol-3-ium chloride; or

wherein F(I) is 3-(dimethoxy (methyl) silyl) propane-1-amine, and F(II) is a mixture of 4,6-dichloro-N,N-diethyl-N-octadecyl-1,3,5-triazin-2-ammonium chloride and 1-(4-chloro-6-methoxy-1.3.5-triazin-2-yl)-1-(2-(dodecanoyloxy) ethyl) piperidin-1-ium perchlorate; or

wherein F(I) is propylsilanotriol, and F(II) is a mixture of 1-(4-(hexadecylamino)-6-(2-(triethoxysilyl) ethoxy)-1,3,5-triazin-2-yl)-1-methylpyrrolidin-1-ium chloride and 1-(4-chloro-6- ((3-(trimethoxysilyl) propyl) amino)-1,3,5-triazin-2-yl)-1-(5-tetradecanamidopentyl)pyrrolidine-1-ium chloride; or

wherein F(I) is a mixture of (3-aminopropyl) trimethoxysilane and triethoxy (3-isocyanatopropyl) silane, and F(II) is a mixture of 1.1′-(6-chlorine-1,3,5-triazin-2,4-diyl)bis (1-(3-tetradecanamidopropyl)-1H-imidazol-1-ium) chloride and 1-(4,6-bis ((3-(trimethoxysilyl)propyl)amino)-1,3,5-triazin-2-yl)-1-(4-(decanoyloxy)butyl)-1H-imidazol-1-ium chloride; or

wherein F(I) is a mixture of triethoxy(propyl) silane and 3-(trimethoxysilyl) propan-1-thiol, and F(II) is a mixture of 1-(4-ethoxy-6-((3-(trimethoxysilyl)propyl)amino)-1,3,5-triazin-2-y1)-1-(7-nonanamidoheptyl)piperidine-1-ium chloride and 1-(4-chloro-6- ((3-(triethoxysilyl)propyl)amino)-1,3,5-triazin-2-yl)-1-(2-(dodecanoyloxy)ethyl) pyrrolidine-1-ium chloride.

2 . The composition according to claim 1 wherein F(I) and F(II) are respectively in a weight ratio ranging from 0.5:1 to 50:1.

3 . The composition according to claim 1 wherein F(I) and F(II) are respectively in a weight ratio ranging from 1:1 to 40:1.

4 . The composition according to claim 1 further comprising a solvent, a rheological property modifier, a thickener, an adhesion agent, an inorganic catalyst or an organic catalyst.

5 . A process for preparing the composition according to claim 1 comprising the steps of:

a) preparing an amount of at least one compound F(I) and an amount of at least one compound F(II) necessary for the composition, b) mixing, and c) recovering the composition according to claim 1 .

6 . The process according to claim 5 wherein the mixing takes place at a temperature between 0° C. and 50° C., for a variable time between 15 minutes and 2 hours.

7 . The process according to claim 5 wherein the mixing is carried out by a mechanical means or a magnetic stirrer.

8 . A process for making a surface or material permanently antimicrobial or antifouling, the process comprising applying the composition according to claim 1 on the surface or material by spraying, coating, painting, trowelling, or deposition by immersion.

9 . The process according to claim 8 further comprising diluting the composition in at least one dispersing agent or diluent selected from the group of: an organic solvent, water, a silane, a polyester, a polyurethane, a polyacrylate, an acrylic monomer, an acrylic resin, an epoxy resin, a polyamide, a polysilane, a polysiloxane, a phenolic resin, a silicone, a melamine, and a gelcoat.

10 . The process according to claim 9 wherein the organic solvent is selected from the group consisting of a halogenated organic solvent, an aliphatic ether, an alcohol, a ketone, an ester, an aromatic hydrocarbon, an aliphatic hydrocarbon, DMSO, an amide, and a carbonate.

11 . The process according to claim 9 wherein the composition is dispersed in at least one dispersing agent with a weight ratio (weight/weight) of dispersing agent: composition of between 1 and 30.

12 . The process according to claim 9 wherein the diluting takes place at a temperature ranging from 0° C. to 50° C., for a time ranging from 15 minutes to 2 hours.

13 . The process according to claim 9 wherein the diluting takes place by mixing conducted with the aid of a mechanical means or a magnetic stirrer.

14 . The process according to claim 8 further comprising adding the composition to a compound or another composition used to form a coating on the surface or on the material without releasing a toxic substance in the environment.

15 . The process according to claim 8 wherein the surface or material is selected from the group consisting of: polypropylene for food or pharmaceutical product packaging, leather, steel, ventilation duct steel, fiberglass, non-acrylic paint, acrylic paint, fiberglass, plasterboard, polyethylene, epoxy resin, wood, paper, wallpaper, and fabric.

16 . An antimicrobial and antifouling material comprising a surface permanently having antimicrobial and antifouling properties, which is obtained by the process according to claim 8 .

17 . A method for preparing a gas impermeable food and pharmaceutical packaging, comprising combining the composition according to claim 1 with a food and pharmaceutical packaging made of a linear hydrocarbon polymer.

18 . The method according to claim 17 wherein the linear hydrocarbon polymer is selected from the group consisting of polyethylene (PE), polybutene (PB) and polypropylene (PP).

19 . The method according to claim 17 , wherein the combining comprises applying the composition on a surface or a material of the food and pharmaceutical packaging by spraying, coating, painting, trowelling, or deposition by immersion.