Antibiofilm formulations and methods

Patent metadata

Field	Value
Publication number	US-2024188564-A1
Application number	US-202218284164-A
Country	US
Kind code	A1
Filing date	Mar 25, 2022
Priority date	Mar 26, 2021
Publication date	Jun 13, 2024
Grant date	—

Abstract

An antibiofilm composition is provided. The antibiofilm composition includes a polycarboxylic acid derivative or a salt thereof, onto which a hydrophobic group, a poly(ethylene oxide) group and/or a poly(propylene oxide) group is covalently bound, an essential oil, and a biosurfactant.

First claim

1 - 70 . (canceled)

71 . An antibiofilm combination, comprising:
a compound of Formula (I):

or a salt thereof, wherein:
R is selected from the group consisting of

(C 1 -C 24 )alkyl, (C 2 -C 24 )alkenyl, (C 2 -C 24 )alkynyl, -(EO) t -(PO) w1 -(C 1 -C 24 )alkyl, -(EO) t -(PO) w1 -(C 2 -C 24 )alkenyl, -(EO) t -(PO) w1 -(C 2 -C 24 )alkynyl,
-(PO) w1 -(EO)(C 2 -C 24 )alkenyl, -(PO) w1 -(EO)(C 2 -C 24 )alkynyl, —(CH 2 ) p —OR 1 , —(CH 2 ) p —NR 1 R 2 , —(CH 2 ) p —OC(═O)R 1 , —(CH 2 ) p —NR 2 C(═O)R 1 , (C 1 -C 24 )acyl, aryl and a steroidyl group; each Y 1 , Y 2 , Y 3 and Y 4 is independently selected from the group consisting of —OR 3 and —NR 3 R 4 ; Y 5 is selected from the group consisting of —OR 1 and —NR 1 R 2 ; each R 1 is independently selected from the group consisting of (C 1 -C 24 )alkyl, -(EO) t C 1 -C 24 )alkyl, (C 2 -C 24 )alkenyl, -(EO) t -(PO) w1 -(C 1 -C 24 )alkyl, -(EO) t -(PO) w1 -(C 2 -C 24 )alkenyl, -(EO) t -(PO) w1 -(C 2 -C 24 )alkynyl, -(PO) w1 -(EO)4C 2 -C 24 )alkenyl, -(PO) w1 -(EO)(C 2 -C 24 )alkynyl, aryl and a steroidyl group; each R 2 , R 3 and R 4 is independently selected from the group consisting of H, (C 1 -C 24 )alkyl, (C 2 -C 24 )alkenyl, (C 2 -C 24 )alkynyl, -(EO) t -(PO) w1 -(C 1 -C 24 )alkyl, -(EO) t -(PO) w1 -C 2 -C 24 )alkenyl, -(EO) t -(PO) w1 -(C 2 -C 24 )alkynyl, -(PO) w1 -(EO) t -C 1 -C 24 )alkyl, -(PO) w1 -(EO)4C 2 -C 24 )alkenyl, -(PO) w1 -(EO) t -(C 2 -C 24 )alkynyl, aryl and a steroidyl group; each Z is independently selected from the group consisting of (C 2 -C 6 )alkylene, (C 3 -C 6 )cycloalkylene and —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —; wherein each (C 2 -C 6 )alkylene and (C 3 -C 6 )cycloalkylene is independently unsubstituted or substituted by one or more identical or different substituents R 5 ; wherein each aryl, (C 1 -C 24 )alkyl, (C 2 -C 24 )alkenyl and (C 2 -C 24 )alkynyl is independently unsubstituted or substituted by one or more identical or different substituents R 6 ; wherein each R 5 and each R 6 is independently selected from the group consisting of halogen, —OH, —O—(C 1 -C 4 )alkyl, CF 3 , and —CN; each n is independently 1, 2, 3 or 4; each p is independently 2, 3 or 4; each t is independently a number between 1 and 50; and each w1 is independently a number between 0 and 10.
an essential oil; and
a biosurfactant selected from the group consisting of an alkyl polyglycoside, a rhamnolipid,
a sophorolipid and a combination thereof.

72 . The antibiofilm combination of claim 71 , wherein:
each R 1 is independently selected from the group consisting of (C 8 -C 18 )alkyl and -(EO) t -C 8 -C 18 )alkyl; R 2 and R 4 are each H; and each R 3 is independently selected from the group consisting of H, (C 8 -C 18 )alkyl and (EO) t -(C 8 -C 18 )alkyl, wherein each t is independently a number between 1 and 30.

73 . The antibiofilm combination of claim 71 , wherein Z is selected from the group consisting of —CH 2 —CH 2 —,

and —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —.

74 . The antibiofilm combination of claim 71 , wherein n is 1 or 2.

75 . The antibiofilm combination of claim 71 , wherein R is

76 . The antibiofilm combination of claim 75 , wherein Y 1 =OH, Y 2 =OH and Y 3 =OH.

77 . The antibiofilm combination of claim 75 , wherein Y 1 =Y 5 , Y 2 =OH and Y 3 =OH.

78 . The antibiofilm combination of claim 71 , wherein the compound of Formula (I) is:

or a salt thereof.

79 . The antibiofilm combination of claim 71 , wherein the compound of Formula (I) is:

or a salt thereof.

80 . The antibiofilm combination of claim 71 , wherein R is

(C 8 -C 18 )alkyl, (C 8 -C 18 )alkenyl, (C 8 -C 18 )alkynyl or —(CH 2 ) p —OC(═O)R 1 , wherein p=2.

81 . An antibiofilm combination, comprising:
a compound of Formula (IIIA):

or a salt thereof, wherein:
R 19 is selected from the group consisting of H, (C 1 -C 24 )alkyl, (C 2 -C 24 )alkenyl, (C 2 -C 24 )alkynyl, -(EO) t -(PO) w1 -(C 1 -C 24 )alkyl, -(EO) t -(PO) w1 -(C 2 -C 24 )alkenyl,
-(EO) t -(PO) w1 -(C 2 -C 24 )alkynyl,
-(PO) w1 -(EO) t -(C 2 -C 24 )alkenyl and -(PO) w1 -(EO) t -(C 2 -C 24 )alkynyl,
R 18 is selected from the group consisting of H, (C 1 -C 24 )alkyl, (C 2 -C 24 )alkenyl,
(C 2 -C 24 )alkynyl; -(EO) t -(PO) w1 -(C 1 -C 24 )alkyl, -(EO) t -(PO) w1 -(C 2 -C 24 )alkenyl,
-(EO) t -(PO) w1 -(C 2 -C 24 )alkynyl,
-(PO) w1 -(EO) t -(C 2 -C 24 )alkenyl and -(PO) w1 -(EO) t -(C 2 -C 24 )alkynyl,
wherein at least one of R 18 and R 19 is not H;
each (C 1 -C 24 )alkyl, (C 2 -C 24 )alkenyl and (C 2 -C 24 )alkynyl is independently unsubstituted or substituted by one or more identical or different substituents R 6;
wherein each R 6 is independently selected from the group consisting of halogen, —OH, —O—(C 1 -C 4 )alkyl, CF 3 , and —CN;
each t is independently a number between 1 and 50; and
each w1 is independently a number between 1 and 10;

an essential oil; and
a biosurfactant selected from the group consisting of an alkyl polyglycoside, a rhamnolipid,
a sophorolipid and a combination thereof.

82 . An antibiofilm combination, comprising:
a compound of Formula (VII):

or a salt thereof, wherein:
R 20 is selected from the group consisting of: (C 1 -C 24 )alkyl, (C 2 -C 24 )alkenyl,
(C 2 -C 24 )alkynyl, -(EO) t -(PO) w1 -(C 1 -C 24 )alkyl, -(EO) t -(PO) w1 -(C 2 -C 24 )alkenyl,
-(EO) t (PO) w1 -(C 2 -C 24 )alkynyl, -(PO) w1 -(EO) t -(C 1 -C 24 )alkyl,
-(PO) w1 -(EO)(C 2 -C 24 )alkenyl, -(PO) w1 -(EO) t -C 2 -C 24 )alkynyl,

t is a number between 1 and 50;

u is a number between 1 and 23;
w1 is a number between 0 and 10; and
w2 is a number between 0 and 10;
each (C 1 -C 24 )alkyl, (C 2 -C 24 )alkenyl and (C 2 -C 24 )alkynyl is independently unsubstituted or substituted by one or more identical or different substituents R 6 ;
wherein each R 6 is independently selected from the group consisting of halogen, —OH, —O—(C 1 -C 4 )alkyl, CF 3 , and —CN

an essential oil; and
a biosurfactant selected from the group consisting of an alkyl polyglycoside, a rhamnolipid,
a sophorolipid and a combination thereof.

83 . The antibiofilm combination of cla

Assignees

• Suncor Energy Inc

Inventors

• Fefer Michael
• Liu Jun
• Ng Kenneth
• Terazono Yuichi
• Ckurshumova Wenzi

Classifications

• A01N65/44

  Poaceae or Gramineae [Grass family], e.g. bamboo, lemon grass or citronella grass · CPC title

• A01N45/00

  Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring (halogenated hydrocarbons A01N29/08; condensed with heterocyclic rings A01N43/00) · CPC title

• A01N37/36

  containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids · CPC title

• A01N35/02

  containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals · CPC title

• A01N31/14

  Ethers · CPC title