Login| Sign Up| Help| Contact|

Patent Searching and Data


Title:
MELAMINE-BASED POLYMERS AND USES THEREOF
Document Type and Number:
WIPO Patent Application WO/2021/245663
Kind Code:
A4
Abstract:
The present disclosure relates to melamine-based compounds that act as carrier for biocides, products comprising the compounds and uses thereof.

Inventors:
HITRIK MARIA (IL)
Application Number:
PCT/IL2021/050650
Publication Date:
January 13, 2022
Filing Date:
June 01, 2021
Export Citation:
Click for automatic bibliography generation   Help
Assignee:
BIO FENCE LTD (IL)
International Classes:
C08G12/32; C07D251/64; C07D487/22; C08G12/38; C08L61/28; C08L61/30; C09D161/28; C09D161/30
Attorney, Agent or Firm:
SEGAL, Dalia (IL)
Download PDF:
Claims:
AMENDED CLAIMS received by the International Bureau on 22 November 2021 (22.11.21 )

1. A melamine-based compound having a structure represented by Formula (I): wherein M is a melamine-based monomeric unit, *, **, *** denote polymerization points, n denote the number of * and is selected from 0 to 100, q denote the number of ** and is selected from 0 to 100, r denote the number of *** and is selected from 0 to 100, provided that n+q+r is at least 1 and wherein A, B and C are end groups and each is independently selected from OH,

H, -CH2-(OH), -C(=O)-H, -C(=O)-OH, -CH3, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted hetcrocyclyl, optionally substituted aryl, optionally substituted heteroaryl, (C(OH))m, (C(OH))m-(O- CH2)p, (C(OH))m.(OCH2-NH-C(O)-NH-CH2OCH2-)p, (C(OH))m-(-NH-C(=O)-NH-CH2)p, (C(OH))m-(C(=O))p, (C(OH))m-(CH2)p-C(=O) or (C(OH))m-(CH2)p-C(OH).

2. The melamine-based compound of claim 1, wherein the monomeric units having a structure represented by Formula (II):

wherein:

Xi, X2, X3, is each independently of the other selected from H, alkyl, alkenyl, alkynyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl;

Li. L2, L3 is each independently of the other selected from absent, optionally substituted alkyl, optionally substituted alkylene, optionally substituted alkynyl, optionally substituted heteroalkyl, optionally substituted heteroalkylene, optionally substituted heteroalkynyl, or

Li is R1-Ra, wherein R1 is selected from (N)m, (C(OH))m, (CH2)m, (CH)m, (C)m,

S(O)m;

L2 is R2-R13, wherein R2 is selected from (N)m, (C(OH))m, (CH2)m, (CH)m, (C)m,

S(O)m;

L3 is R3-Rc, wherein R3 is selected from (N)m, (C(OH))m, (CH2)m, (CH)m, (C)m, S(O)m; m is an integer selected from 1 to 10, each of Ra, Rb, Rc is independently of the other selected from absent or alkyl, alkylene, alkynyl, (-0-)p, (-0-CH2-)P, (-OCH2-NH-C(=O)-NH-CH2OCH2-)P, (-OCH2- C(=O)-NH-C(=O)-CH2OCH2-)p, (-OCH2-NH-C(=O)-NH-CH2-)p, (-NH-)p, (-NH-C(=O)- )p, (-NH-C(=O)-NH-)p, (-NH-C(=O)-NH-CH2)p, (-NH-C(=O)-NH-CH2O-)p, -NH-(CH2)p- C(=O), -NH-(CH2)P-C(OH), -NH-C(=O)-(CH2)p-, -(NH-CH2)p-, -NH-(CH2)p-, -NH- (S(=O))P-(CH2)p-, -(NH-S(=O)-(CH2))p-, (C(=O))p, (-C(=O)-NH-C(=O)-)p, -C(=O)- (CH2)P-C(=O), -C(=O)-(CH2)P-NH, -NH-(CH2)P-NH, -C(=O)-(CH2)P-C(OH), -C(=O)- NH-(CH2)p-, C(=O)-(CH2)p-, (C(=O)-CH2)p, -(CH2)P, -(CH2)P-C(=O), -(CH2)P-NH, -(CH2)p-C(OH), (C(OH))p, -C(OH)-(CH2)p-C(=O), -C(OH)-(CH2)P-NH, -C(OH)-(CH2)p- C(OH), -S-S-(CH2)p-, -S-(CH2)p-, -(S-CH2)p-; p is an integer selected from 1 to 10 and represents a connection point.

3. The melamine-based compound of claim 2, wherein Li is absent or R1-Ra.

4. The melamine-based compound of claim 2, wherein L2 is absent or R2-Rb.

5. The melamine-based compound of claim 2, wherein L3 is absent or R3-Rc.

6. The melamine-based compound of any one of claims 2 to 5, wherein Xi, X2, X3, is each independently of the other selected from H and C1-C6 alkyl.

7. The melamine-based compound of any one of claims 2 to 6, wherein Ri R2 R3 is independently of the other selected to be absent, (C(OH))m, (CH2)m, and m is independently selected from 1 to 6.

8. The melamine-based compound of any one of claims 2 to 7, wherein (ii) R1 is (C(OH))m, R2 is (C(OH))m and R3 is (C(OH))m, (iii) R1 is (C(OH))m, R2 is absent and R3 is absent, (iv) R1 is (CH2)m, R2 is absent and R3 is absent or (v) R1 is (CH2)m, R2 is (C(OH)) m and R3 is absent, and m is independently selected from 1 to 6.

9. The melamine-based compound of any one of claims 2 to 8, wherein R1 is (C(OH)), (CH2), R2 is absent or (C(OH)) and R3 is absent or (C(OH)).

10. The melamine-based compound of any one of claims 2 to 9, wherein each of Ra, Rb, Rc is independently of the other selected to be absent, (-0-CH2)p, (OCH2-NH-C(=O)- NH-CH2O CH2-)p, (-NH-C(=O)-NH-CH2)p, -(CH2)P-C(=O), -(CH2)P-C(OH), (C(OH))p, or (-NH-CH2-)p, wherein p is an integer between 1 to 10.

11. The melamine-based compound of any one of claims 2 to 10, wherein R1 is absent, (C(OH))m, or (CH2)m and Ra is absent, (-0-CH2)p, (OCH2-NH-C(=O)-NH- CH2OCH2-)p, (-NH-C(=O)-NH-CH2)p, -(CH2)P-C(=O), -(CH2)p-C(OH), (-NH-CH2-)p, or (C(OH))p.

12. The melamine-based compound of any one of claims 2 to 10, wherein R2 is absent or (C(OH))m and Rb is absent, (-0-CH2)p, (OCH2-NH-C(=O)-NH-CH2OCH2-)p, (-NH- C(=O)-NH-CH2)p, , -(CH2)p-C(=O), -(CH2)P-C(OH) or (C(OH))p.

13. The melamine-based compound of claim 12, wherein R2 is absent or (C(OH))m and Rb is absent, (CH2)p-C(OH) or (C(OH))p.

14. The melamine-based compound of any one of claims 2 to 10, wherein R3 is absent, (CFhV, or (C(OH)) mand Rc is absent, (CH2)p-C(OH), NH-CH2)P, or (C(OH))p.

15. The melamine- based compound of any one of claims 2 to 14, wherein (i) R1 is (C(O)), Ra is absent, C(=O), (CH2)4-C(=O) or (CH2)3-C(=O), R2 is absent and R3 is absent, (11) R1 is (C(OH)), Ra is absent, C(OH), (CH2)4-C(OH), (CH2)3-C(OH), R2 is (C(OH)) Rb is absent, C(OH), (CH2)4-C(OH) or (CH2)3-C(OH), R3 is (C(OH)) and Rc is absent, C(OH), (CH2)4-C(OH) or (CH2)3-C(OH), (111) R1 is (C(OH)), Ra is C(OH), (CH2)4-C(OH), (CH2)3-C(OH), R2 IS C(OH) Rb is C(OH), (CH2)4-C(OH) or (CH2)3- C(OH), R3 IS C(OH) and Rc is C(OH), (CH2)4-C(OH) or (CH2)3-C(OH), (iv) R1 is (C(OH)), Ra is absent, C(OH), (CH2)4-C(OH), (CH2)3-C(OH), R2 is absent and R3 is absent, (v) R1 is (C(OH)), Ra is (CH2)4-C(OH), (CH2)3-C(OH), R2 is absent and R3 is absent, (vi) R1 is (CH2), Ra is absent, -O-CH2, OCH2-NH-C(O)-NH-CH2OCH2-, R2 is absent and R3 is absent, (vii) R1 is (CH2), Ra is absent, (-NH-CFh^-O-CFh, OCH2-NH- C(O)-NH-CH2OCH2-, R2 IS (exon)), Rb is (CH2)4-C(OH), (CH2)3-C(OH) and R3 is absent, (vin) R1 is (CH2), Ra is absent, (-NH-CH2)4, -O-CH2, OCH2-NH-C(O)-NH- CH2OCH2-, R2 IS absent, R3 is (CH2) and Rc is absent, (-NH-CH2)4, -O-CH2, OCH2-NH- C(O)-NH-CH2OCH2-or (ix) a combination thereof.

16. The melamine-based compound of claim 2, wherein the monomeric unit having a structure represented by Formula (VI): wherein Ra is as defined herein above.

17. The melamine-based compound of claim 16, wherein Ra is-(CH2)p-C(=O) and p is 1, 2, 3, 4, 5, or 6.

18. The melamine-based compound of claim 16, wherein Ra is (CH2)3-C(=O) or (CH2)4-C(=O).

19. The melamine- based compound of claim 1, wherein the monomeric unit having a structure represented by Formula (VII): wherein Ra, Rc, are as defined herein above.

20. The melamine-based compound of claim 19, wherein Ra is C(OH), Rb is C(OH) and Rc is C(OH).

21. The melamine-based compound of claim 19, wherein Ra is -(CH2)p-C(OH), Rb is -(CH2)p-C(OH), RC IS -(CH2)P-C(OH) and p is 3 or 4.

22. The melamine-based compound of any one of claims 19 to 21, wherein Xi is methyl or H.

23. The melamine- based compound of claim 1, wherein the monomeric unit having a structure represented by Formula (IX): wherein Ra is as defined herein above.

24. The melamine-based compound of claim 23, wherein Ra is absent, C(OH), - (CH2)p-C(OH) and p is 1, 2, 3, 4, 5, or 6.

25. The melamine-based compound of claim 23 or 24, wherein Ra is absent, C(OH), (CH2)3-C(OH) or (CH2)4-C(OH).

26. The melamine- based compound of claim 1, wherein the monomeric unit having a structure represented by Formula (XI): wherein Ra, Rc, are as defined herein above.

27. The melamine-based compound of claim 26, wherein Rc is absent, C(OH), - (CH2)p-C(OH) and p is 1, 2, 3, 4, 5, or 6.

28. The melamine-based compound of claim 26 or 27, wherein Rc is absent, C(OH), (CH2)3-C(OH) or (CH2)4-C(OH).

29. The melamine- based compound of claim 1, wherein the monomeric unit having a structure represented by Formula (XIa): wherein Ra, as defined herein above. 31. The melamine-based compound of any one of claims 26 to 30, wherein Ra is - 0(CH2)p-,(NH-(CH2))p, (-OCH2-NH-C(O)-NH-CH2O- CH2)p, (-NH-C(O)-NH-CH2)P and p is 1, 2, 3, 4, 5, or 6.

32. The melamine-based compound of any one of claims 1-31, wherein the monomeric unit having a structure represented by Formula (XV):

33. The melamine-based compound of claim 1 to 31, wherein the monomeric unit having a structure represented by Formula (XVII), (XVII) or (XVIII):

34. The melamine-based compound of any one of claims 1 to 31, wherein the monomeric unit having a structure represented by Formula (XX), (XXa), (XXb), (XXI), (XXIa) or (XXIb), (XXII), (XXIII), (XIV) or (XV):

35. The melamine-based compound of any one of claims 1 to 34 for use as a carrier for at least one biocide. 36. The melamine-based compound of any one of claims 1 to 34 for use as an adjuvant for at least one biocide.

37. The melamine-based compound of any one of claims 1 to 34, in a form of a polymeric matrix holding the matrix the at least one biocide.

38. The melamine-based compound of any one of claims 1 to 37, wherein the biocide is a negatively charged, polar, electronegative biocide.

39. The melamine-based compound of any one of claims 1 to 38, wherein the biocide is at least one of a chloride-based biocide, a bromide-based biocide, an iodide-based biocide, hydrogen peroxide, or a preservative.

40. The melamine-based compound of any one of claims 36 to 39, wherein the melamine-based compound and the at least one biocide are capable of interacting by non- covalent binding.

41. A product comprising the melamine-based compound of any one of claims 1 to 40 and at least one product specific-substance.

42. The product of claim 41, wherein the at least one product specific- substance is at least one of a second polymer, a powder mixture, an adhesive, a sealant, a pigment, a varnish or a wax.

43. The product of claim 42, wherein the second polymer is selected from polystyrene, polyamide, polyethyleneimine, polycarbonate, polyolefin, styrene- acrylonitrile, acrylonitrile-butadiene-styrene, polyester, polyurethane, epoxide, polyphenylene ether, halogen-substituted organic polymer, phthalic acid amide, polyphenylene sulfide, liquid crystal polymers, polyethylene terephthalate cyclohexane or combinations thereof.

44. The product of any one of claims 41 to 43 for use in coating a surface.

45. The product of claim 44, wherein the surface is metal surface, wood surface, plastic surface, ceramic surface, glass surface, tiles, textile surface or combination thereof.

46. The product of any one of claims 41 to 43, being a paint formulation. 47. A particulate matter comprising the melamine-based compound of any one of claims 1 to 34.

48. The particulate matter of claim 47, comprising at least one second polymer.

49. The particulate matter of claim 48, wherein the second polymer is or comprises one or more polyolefins.

50. A polymeric fiber, film or non-woven fabric comprising the melamine-based compound of any one of claims 1 to 34.

51. A method for reducing or eliminating growth of at least one microbe, the method comprises applying an effective amount of a melamine-based compound, a population of polymers or a product comprising the same, on at least one surface, and applying on said surface at least one biocide, wherein the melamine-based compound is defined in any one of claims 1 to 34, and wherein the melamine-based compound and the at least one biocide are capable of interacting by non-covalent binding to thereby reduce or eliminate growth of at least one microbial.

52. The method of claim 51, comprising applying the at least one biocide by spraying, brushing, fogging, wiping, dipping or any combination thereof.

53. The method of claim 5 lor 52, wherein the biocide is a negatively charged, polar, electronegative biocide.

54. The method of any one of claims 51 to 53, wherein the surface is metal surface, wood surface, plastic surface, ceramic surface, glass surface, tiles, textile surface or combination thereof

55. The method o of any one of claims 51 to 54, wherein the microbe is at least one of bacteria, a virus, a yeast, a fungi, a protozoa, an algae, an archaea, their toxins or by products

56. A melamine-based compound having a structure represented by Formula (I):

wherein M is a melamine-based monomeric unit, *, **, *** denote polymerization points, n denote the number of * and is selected from 0 to 100, q denote the number of ** and is selected from 0 to 100, r denote the number of *** and is selected from 0 to 100, and wherein A, B and C are end groups and each is independently selected from OH, H, -CH2-(OH), -C(=O)-H, -C(=O)-OH, -CH , optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted hetcrocyclyl, optionally substituted aryl, optionally substituted heteroaryl, (C(OH))m, (C(OH))m-(O-CH2)p, (C(OH))m.(OCH2-NH-C(=O)-NH-CH2OCH2-)p, (C(OH))m-(-NH- C(=O)-NH-CH2)p, (C(OH))m-(C(=O))p, (C(OH))m-(CH2)p-C(=O) or (C(OH))m-(CH2)p- C(OH) for use as a carrier of at least one biocide, wherein the melamine-based compound is capable of interacting by non-covalent binding with at least one biocide.

57. The melamine-based compound of claim 56, wherein n+q+r is 0 or 1.

58. The melamine-based compound of claim 56 or 57, wherein the melamine-based monomeric unit is as defined in any one of claims 2 to 34.