Polyamide nanoparticles and uses thereof

Patent metadata

Field	Value
Publication number	US-2019002706-A1
Application number	US-201816123758-A
Country	US
Kind code	A1
Filing date	Sep 6, 2018
Priority date	Jan 23, 2014
Publication date	Jan 3, 2019
Grant date	—

Abstract

Nanoparticles of N-halamine-derivatized crosslinked polyamide. Process of preparing the polymeric nanoparticles per se and incorporated in or on a substrate. Uses of the polymeric nanoparticles and of substrates incorporating same, particularly for reducing a formation of organic-based contaminants, e.g., load of a microorganism or of a biofilm.

First claim

What is claimed is:

1 . An article comprising a composition-of-matter of comprising a plurality of crosslinked polymeric backbones, wherein at least 80% of said plurality of crosslinked polymeric backbones are characterized by an average hydrodynamic diameter of less than 500 nm, said crosslinked polymeric backbones being represented by the general Formula I:
([A 1 ] x [A 2 ] y )B n
wherein:
(a) A 1 is a monomeric unit derived from a secondary diamide compound, said secondary diamide compound being represented by the general formula II:

such that
R 1 and R 3 are hydrogen or a methyl group; and
R 2 is C 1 -C 4 alkyl group;
(b) A 2 is a monomeric unit being a primary amide selected from the group consisting of: acrylamide, alkylacrylamide, and any derivative thereof;
(c) each of said plurality of polymeric backbones is crosslinked by at least one A 1 ;
(d) B, in each instance, is a halogen atom independently selected from the group consisting of Cl, Br, and I;
(e) x and y are integers, independently, representing the total numbers of A 1 and A 2 , respectively, in said plurality of crosslinked polymeric backbones, said x and said y having a value of at least 5:
(f) n represents the total numbers of said B; and wherein:
said composition is incorporating within, or coated on a surface of said article.

2 . The article of claim 1 , being selected from the group consisting of a medical device, organic waste processing device, fluidic device, water system device, tubing, an agricultural device, a package, a sealing article, a fuel container and a construction element.

3 . The article of claim 1 , wherein said halogen atom, in one or more instances, is bound to the nitrogen belonging to said A 1 and/or to said A 2 .

4 . A method of inhibiting or reducing a formation of load of organic-based contaminant on or within an article, the method comprising incorporating within, or coating on a surface of said article, a composition-of-matter comprising:
a plurality of crosslinked polymeric backbones, wherein at least 80% of said plurality of crosslinked polymeric backbones are characterized by an average hydrodynamic diameter of less than 500 nm, said crosslinked polymeric backbones being represented by the general Formula I:
([A 1 ] x [A 2 ] y )B n
wherein:
(a) A 1 is a monomeric unit derived from a secondary diamide compound, said secondary diamide compound being represented by the general formula II:

R 1 and R 3 are hydrogen or a methyl group; and
R 2 is C 1 -C 4 alkyl group;
(b) A 2 is a monomeric unit being a primary amide selected from the group consisting of: acrylamide, alkylacrylamide, and any derivative thereof;
(c) each of said plurality of polymeric backbones is crosslinked by at least one A 1 ;
(d) B, in each instance, is a halogen atom independently selected from the group consisting of Cl, Br, and I;
(e) x and y are integers, independently, representing the total numbers of A 1 and A 2 , respectively, in said plurality of crosslinked polymeric backbones, said x and said y having a value of at least 5; and wherein:
(f) n represents the total numbers of said B.

5 . The method of claim 4 , wherein said load of organic-based contaminant is selected from a load of a microorganism, or biofilm, said microorganism being selected from the group consisting of: viruses, fungi, parasites, yeast, bacteria, and protozoa.

6 . The method of claim 5 , wherein the bacterium is selected from the group consisting of: Gram positive bacteria, and Gram negative bacteria.

7 . The method of claim 6 , wherein the bacterium is selected from the group consisting of Gram negative bacteria.

8 . The method of claim 4 , wherein said load of organic-based contaminant is maintained substantially reduced over a period of up to at least six months.

9 . The method of claim 4 , further comprising one or more dehalogenating-rehalogenating cycles with halogen atoms selected from the group consisting of Cl, Br, and I.

10 . The method of claim 9 , wherein said load of organic-based contaminant is maintained substantially reduced after at least one dehalogenating-rehalogenating cycle with said halogen atom.

11 . The method of claim 4 , wherein said A 2 is methacrylamide.

12 . The method of claim 4 , wherein said A 1 is selected from the group consisting of: N,N′-methylene bisacrylamide, N,N′-ethylene bisacrylamide, and any derivative thereof.

13 . The method of claim 12 , wherein said A 1 is N,N′-methylene bisacrylamide.

14 . The method of claim 4 , wherein said halogen atom, in one or more instances, is bound to the nitrogen belonging to said A 1 and/or to said A 2 .

15 . The method of claim 4 , wherein said n has a value such that n/(x+y) multiplied by 100 is at least 0.1.

16 . The method of claim 4 , wherein said composition-of-matter is prepared by the process comprising:
co-polymerizing a plurality of said monomeric units, A 1 and A 2 , said co-polymerizing comprising dispersing said monomers in a weight ratio of A 1 /A 2 that ranges from about 1/9 to about 6/4 in a surfactant-free aqueous phase comprising at least one water soluble initiator, to thereby obtain a plurality of crosslinked polymeric backbones characterized by an average hydrodynamic diameter of less than 500 nm with a size distribution of that varies within a range of less than 20%.

17 . The method of claim 16 , wherein said at least one water soluble initiator is selected from the group consisting of: AIBNCO 2 H, H 2 O 2 , potassium persulfate (PPS), and azobisisobutylonitrile (AIBN).

18 . The method of claim 16 , wherein said surfactant-free aqueous phase further comprises one or more reducing agent selected from the group consisting of: a sulfite, a bisulfate, thiosulfate, formamidinesulfinic acid, and ascorbic acid.

19 . The method of claim 16 , wherein said process further comprises a step of at least partially halogenating said polymeric material, by an addition of a halide source.

20 . The method of claim 19 , wherein said halide source comprises a salt of a material selected from the group consisting of: di-X-isocyanurate, N—X-succinimide, or hypo-halite, wherein said halite and X each are each, independently, selected from the group consisting of: Cl, I, or Br.

Assignees

• Univ Bar Ilan

Inventors

• Margel Shlomo
• Banin Ehud
• Gutman Ori
• Natan Michal

Classifications

• B82Y5/00

  Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery · CPC title

• C09D133/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title

• C09D5/1662 Primary

  Synthetic film-forming substance · CPC title

• A01N37/28

  containing the group [IMAGE cpc-sch-A01N-0937.gif]; Thio analogues thereof · CPC title

• C08F220/56 Primary

  Acrylamide; Methacrylamide · CPC title