Polyamide nanoparticles and uses thereof

Patent metadata

Field	Value
Publication number	US-10072161-B2
Application number	US-201515113313-A
Country	US
Kind code	B2
Filing date	Jan 22, 2015
Priority date	Jan 23, 2014
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

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. 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:

such that
R 1 and R 3 are hydrogen or a methyl group; and
R 2 is C1-C4 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 A1;
(d) B, in each instance, is a halogen atom independently selected from the group consisting of Cl, Br, and I, 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 ;
(e) x and y are integers, independently, representing the total numbers of A1 and A2, respectively, in said plurality of crosslinked polymeric backbones, said x and said y having a value of at least 5; and
(f) n represents the total numbers of said B.

2. The composition-of-matter of claim 1 , wherein said A 2 is methacrylamide.

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

4. The composition-of-matter of claim 3 , wherein said A 1 is N,N′-methylene bisacrylamide.

5. The composition-of-matter of claim 1 , wherein said n has a value such that n/(x+y) multiplied by 100 is at least 0.1.

6. The composition-of-matter of claim 1 , being in the form of a dry powder.

7. The composition-of-matter of claim 1 , wherein said plurality of crosslinked polymeric backbones is characterized by an average hydrodynamic diameter of less than 50 nm with a size distribution of that varies within a range of less than 20%.

8. The composition-of-matter of claim 1 , further comprising a substrate, wherein said plurality of crosslinked polymeric backbones is incorporated or coated in/on at least a portion of said substrate.

9. The composition-of-matter of claim 8 , wherein said substrate is or forms a part of an article.

10. The composition-of-matter of claim 8 , wherein said substrate comprises or is made of a polymer, wood, a metal, glass, carbon, a biopolymer and/or silicon.

11. An article comprising the composition-of-matter of claim 1 .

12. The article of claim 11 , 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.

13. A method of inhibiting or reducing a formation of load of organic-based contaminant on or within an article, the method comprising incorporating or coating the composition-of-matter of claim 1 on and/or within said article.

14. The method of claim 13 , wherein said load of organic-based contaminant is a load of a microorganism, and/or a formation of a biofilm or biofouling in and/or on an article, said microorganism being selected from the group consisting of: viruses, fungi, parasites, yeast, bacteria, and protozoa.

15. The method of claim 13 , further comprising one or more dehalogenating-rehalogenating cycles with halogen atoms selected from the group consisting of Cl, Br, and I.

16. A process of preparing the composition-of-matter of claim 1 , 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 process 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 PPS (potassium persulfate) and AIBN (azobisisobutylonitrile).

18. The process of claim 17 , wherein said surfactant-free aqueous phase further comprising one or more reducing agent selected from the group consisting of: a sulfite, a bisulfite, thiosulfate, formamidinesulfinic acid, and ascorbic acid.

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

20. The composition-of-matter of claim 1 , wherein at least 1% of the hydrogens bound to a nitrogen atom in the crosslinked polymeric backbones are substituted by a halogen atom.

Assignees

• Univ Bar Ilan
• Univ Bar Ilan

Inventors

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

Classifications

• C08F2810/20

  leading to a crosslinking, either explicitly or inherently · CPC title

• C08F220/56 Primary

  Acrylamide; Methacrylamide · CPC title

• B82Y5/00

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

• C09D5/14

  Paints containing biocides, e.g. fungicides, insecticides or pesticides (C09D5/16 takes precedence) · CPC title

• C08F222/385

  Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide · CPC title