Biocide compositions

Patent metadata

Field	Value
Publication number	US-9833002-B2
Application number	US-201615193983-A
Country	US
Kind code	B2
Filing date	Jun 27, 2016
Priority date	Aug 2, 2013
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

Disclosed are biocide compositions. The compositions are useful in applications relating to the production, transportation, storage, and separation of crude oil and natural gas. Also disclosed are methods of using the compositions, particularly in applications relating to the production, transportation, storage, and separation of crude oil and natural gas.

First claim

What is claimed is:

1. A method of controlling microbe proliferation in a system used in a coal-fired process, a waste-water process, a farm, a slaughter house, a land-fill, a municipality waste-water plant, a coking coal process, or a biofuel process, the method comprising contacting the system with an effective amount of a biocide composition, the biocide composition comprising
an imidazoline compound;
a quaternary amine; and
a phosphonium compound;
wherein the imidazoline compound has a structure of formula (I), (II), or (III),

wherein
R 1 , R 4 , and R 5 are each independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, and heterocycle,
said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, and heterocycle each independently, at each occurrence, unsubstituted or substituted with 1 to 3 substituents independently selected from halogen, —COR 6 , —CO 2 R 7 , —SO 3 R 8 , —PO 3 H 2 ,)—CON(R 9 )(R 10 ), —OR 11 , and —N(R 12 )(R 13 );
R 2 is a radical derived from a fatty acid;
R 3 and R x are independently selected from a radical derived from an unsaturated acid;
R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently, at each occurrence, selected from hydrogen, alkyl, and alkenyl;
R 12 and R 13 are each independently, at each occurrence, selected from hydrogen, alkyl, —COR 14 , —CO 2 R 15 , -alkyl-COR 16 , and -alkyl-CO 2 R 17 ; and
R 14 ,R 15 , R 16 , and R 17 are each independently, at each occurrence, selected from hydrogen, alkyl, and alkenyl.

2. The method of claim 1 , wherein the imidazoline compound has formula (I),

wherein
R 1 , R 4 , and R 5 are each independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, and heterocycle,
said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, and heterocycle each independently, at each occurrence, unsubstituted or substituted with 1 to 3 substituents independently selected from halogen, -COR 6 , —CO 2 R 7 , —SO 3 R 8 , —PO 3 H 2 , —CON(R 9 )(R 10 ) —OR 11 , and —N(R 12 )(R 13 );
R 2 is a radical derived from a fatty acid;
R 3 is selected from a radical derived from an unsaturated acid;
R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently, at each occurrence, selected from hydrogen, alkyl, and alkenyl;
R 12 and R 13 are each independently, at each occurrence, selected from hydrogen, alkyl, —COR 14 , —CO 2 R 15 , -alkyl-COR 16 , and -alkyl-CO 2 R 17 ; and
R 14 , R 15 , R 16 , and R 17 are each independently, at each occurrence, selected from hydrogen, alkyl, and alkenyl.

3. The method of claim 2 , wherein
R 1 is unsubstituted C 2 -C 6 -alkyl;
R 2 is —C 17 H 35 , —C 17 H 33 , or —C 17 H 31 ;
R 3 is —CH 2 CH 2 CO 2 R e , wherein R e is hydrogen, C 1 -C 6 -alkyl, or R e is absent;
R 4 is hydrogen; and
R 5 is hydrogen.

4. The method of claim 2 , wherein
R 1 is linear C 2 -alkyl, substituted with one substituent that is a terminal —N(R 12 )(R 13 ), wherein R 12 is hydrogen and R 13 is —COR 14 , wherein R 14 is —C 17 H 35 , —C 17 H 33 , or —C 17 H 31 ;
R 2 is —C 17 H 35 , —C 17 H 33 , or —C 17 H 31 ;
R 3 is —CH 2 CH 2 CO 2 R e , wherein R e is hydrogen, C 1 -C 6 -alkyl, or R e is absent;
R 4 is hydrogen; and
R 5 is hydrogen.

5. The method of claim 2 , wherein
R 1 is linear C 2 -alkyl, substituted with one substituent that is a terminal —N(R 12 )(R 13 ), wherein R 12 and R 13 are each a —C 2 -alkyl-CO 2 R 17 , wherein R 17 is hydrogen or R 17 is absent;
R 2 is —C 17 H 35 , —C 17 H 33 , or —C 17 H 31 ;
R 3 is —CH 2 CH 2 CO 2 R e , wherein R e is hydrogen, C 1 -C 6 -alkyl, or R e is absent;
R 4 is hydrogen; and
R 5 is hydrogen.

6. The method of claim 1 , wherein the imidazoline compound has formula (II),

wherein
R 1 , R 4 , and R 5 are each independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, and heterocycle,
said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, and heterocycle each independently, at each occurrence, unsubstituted or substituted with 1 to 3 substituents independently selected from halogen, —COR 6 , —CO 2 R 7 , —SO 3 R 8 , —PO 3 H 2 ,)—CON(R 9 )(R 10 ), —OR 11 , and —N(R 12 )(R 13 );
R 2 is a radical derived from a fatty acid;
R 3 and R x are each independently selected from a radical derived from an unsaturated acid;
R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently, at each occurrence, selected from hydrogen, alkyl, and alkenyl;
R 12 and R 13 are each independently, at each occurrence, selected from hydrogen, alkyl, —COR 14 , —CO 2 R 15 , -alkyl-COR 16 , and -alkyl-CO 2 R 17 ; and
R 14 , R 15 , R 16 , and R 17 are each independently, at each occurrence, selected from hydrogen, alkyl, and alkenyl.

7. The method of claim 6 , wherein
R 1 is unsubstituted C 2 -C 6 -alkyl;
R 2 is —C 17 H 35 , —C 17 H 33 , or —C 17 H 31 ;
R 3 is —CH 2 CH 2 CO 2 R e , wherein R e is hydrogen, C 1 -C 6 -alkyl, or R e is absent;
R x is —CH 2 CH 2 CO 2 R e , wherein R e is hydrogen, C 1 -C 6 -alkyl, or R e is absent;
R 4 is hydrogen; and
R 5 is hydrogen.

8. The method of claim 6 , wherein
R 1 is linear C 2 -alkyl, substituted with one substituent that is a terminal —N(R 12 )(R 13 ), wherein R 12 is hydrogen and R 13 is —COR 14 , wherein R 14 is —C 17 H 35 , —C 17 H 33 , or —C 17 H 31 ;
R 2 is —C i7 H 35 , —C 17 H 33 , or —C 17 H 31 ;
R 3 is —CH 2 CH 2 CO 2 R e , wherein R e is hydrogen, C 1 -C 6 -alkyl, or R e is absent;
R x is —CH 2 CH 2 CO 2 R e , wherein R e is hydrogen, C 1 -C 6 -alkyl, or R e is absent;
R 4 is hydrogen; and
R 5 is hydrogen.

9. The method of claim 6 , wherein
R 1 is linear C 2 -alkyl, substituted with one substituent that is a terminal —N(R 12 )(R 13 ), wherein R 12 and R 13 are each a —C 2 -alkyl-CO 2 R 17 , wherein R 17 is hydrogen or R 17 is absent;
R 2 is —C 17 H 35 , —C 17 H 33 , or —C 17 H 31 ;
R 3 is —CH 2 CH 2 CO 2 R e , wherein R e is hydrogen, C 1 -C 6 -alkyl, or R e is absent;
R x is —CH 2 CH 2 CO 2 R e , wherein R e is hydrogen, C 1 -C 6 -alkyl, or R e is absent;
R 4 is hydrogen; and
R 5 is hydrogen.

10. The method of claim 1 , wherein the imidazoline compound has formula (III),

wherein
R 1 , R 4 , and R 5 are each independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, and heterocycle,
said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, and heterocycle each independently, at each occurrence, unsubstituted or substituted with 1 to 3 substituents independently selected from halogen, —COR 6 , —CO 2 R 7 , —SO 3 R 8 , —PO 3 H 2 , —CON(R 9 )(R 10 ), and —N(R 12 )(R 13 );
R 2 is a radical derived from a fatty acid;
R 6 , R 7 , R 8 , R 9 , and R 10 are each independently, at each occurrence, selected from hydrogen, alkyl, and alkenyl;
R 12 and R 13 are each independently, at each occurrence, selected from hydrogen, alkyl, —COR 14

Assignees

• Ecolab Usa Inc

Inventors

• Keasler Victor
• Clark Jeffrey Caleb
• Keller-Schultz Carrie
• Bennett Brian

Classifications

• A01N43/50 Primary

  1,3-Diazoles; Hydrogenated 1,3-diazoles · CPC title

• A01N57/34 Primary

  having phosphorus-to-halogen bonds; Phosphonium salts · CPC title

• A01N33/12

  Quaternary ammonium compounds · CPC title

• A01N59/26

  Phosphorus; Compounds thereof · CPC title

• A01N43/28

  with two hetero atoms in positions 1,3 · CPC title