IP Library Granted Patent US 6,846,419
Granted Patent B2
US 6,846,419 · App. 10/348,161 · Granted Jan 25, 2005

Phosphonamide and phosphonamide blend compositions and method to treat water

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Quick Facts
Patent No.
US 6,846,419
App. No.
10/348,161
Granted
Jan 25, 2005
Kind
B2
Abstract

The invention is a water treatment composition comprising at least one phosphonamide and blends thereof and a method to treat water. As phosphonamides are generally odorless, and typically solids, phosphonamide and phosphonamide blend compositions are generally odorless, conveniently processed and manufactured, and safely used without risks of exposure to odors and vapors associated with the corresponding amines. Advantageously, phosphonamides blended with amino-phosphate esters provide useful treatment compositions. The inventive compositions are generally used to treat water contained in water flow systems such as boilers and cooling towers.

Claims (32)

1. A method of treating water in a flowing water system selected from the group consisting of boilers and cooling towers to treat impurities, which can foul the boiler or cooling tower, comprising the step of:

adding to water a composition comprising at least one phosphonamide formed from a reaction between an amine and a phosphonic acid, in an amount sufficient to treat the water, wherein the phosphonamide is an amine derivativized to an amide by said reaction.

2. The method claimed in claim 1 wherein the amine is of the general formula HN—R 1 R 2 wherein R 1 and R 2 independently are selected from the group consisting of H, alkyl, cycloalkyl, aryl, and heteroaryl organic structures having up to 10 atoms selected from the group consisting of C, N, and O,

and wherein R 1 and R 2 taken together with the nitrogen to which they are attached can form a 5 or 6 membered ring containing 0-2 additional heteroatoms selected from N or O.

3. The method claimed in claim 1 wherein the amine is selected from the group consisting of cyclohexylamine, morpholine, octadecylamine, N,N-dimethyl-1,3-propanediamine, and ammonium hydroxide.

4. The method claimed in claim 1 wherein the phosphonic acid is selected from the group consisting of aminotri(methylene phosphonic acid), 1-hydroxyethylidene-1,1-diphosphonic acid, and 2-phosphono-butane-1,2,4-tricarboxylic acid.

5. The method claimed in claim 1 comprising adding to the water a blend of at least two phosphonamides formed from different amines and a phosphonic acid, wherein said blend has a cumulative amine to phosphonic acid mole ratio in the range of from about 1:1 to about 10:1.

6. The method claimed in claim 5 wherein each phosphonamide is present in at least about 10% by weight of the composition.

7. The method claimed in claim 1 further comprising adding to the water an amino-phosphate ester formed from a hydroxyamine and a phosphonic acid.

8. The method claimed in claim 7 wherein the amino-phosphate ester is present in at least about 10% by weight of the composition.

9. The method claimed in claim 7 wherein the hydroxyamine is selected from the group consisting of N,N-diethylethanolamine, 2-amino-2-methyl-1-propanol, 1,1-dimethylamine-propanol, and 2-dimethylamino-2-methyl-1-propanol.

10. The method claimed in claim 1 further comprising adding to the water a hardness control agent.

11. The method claimed in claim 10 wherein the hardness control agent is a sulfonated water soluble polymeric compound.

12. The method claimed in claim 1 wherein the phosphonamide is present in at least about 10% by weight of the composition.

13. The method claimed in claim 1 wherein the composition is a solid.

14. The method claimed in claim 1 wherein the composition is added to boiler water to treat water in a boiler and boiler feedlines.

15. The method claimed in claim 1 wherein the composition is added to water in a cooling tower.

16. The method claimed in claim 1 comprising adding to water an amount of a blend of:

at least two phosphonamides formed from at least two different amines selected from the group consisting of cyclohexylamine, morpholine, octadecylamine, N,N-dimethyl-1,3-propanediamine, and ammonium hydroxide, and a first phosphonic acid; and

an amino-phosphate ester formed from a hydroxyamine selected from the group consisting of N,N-diethylethanolamine, 2-amino-2-methyl-1-propanol, 1,1-dimethylamine-propanol, and 2-dimethylamino-2-methyl-1-propanol, and a second phosphonic acid,

wherein the blend has a cumulative amine to cumulative amine to phosphonic acid mole ratio in the range of from about 1:1 to about 10:1.

17. The method claimed in claim 16 wherein the first acid is the same as the second acid.

18. The method claimed in claim 16 wherein the first and second phosphonic acids are independently selected from the group consisting of aminotri(methylene phosphonic acid), 1-hydroxyethylidene-1,1-diphosphonic acid, and 2-phosphono-butane-1,2,4-tricarboxylic acid.

19. The method claimed in claim 1 comprising adding to water an amount of a blend of:

a morpholine-1-hydroxy-ethylidene-phosphoryl-phosphonamide formed from morpholine present in a range of from about 10% to about 50% by weight and 1-hydroxy-ethylidene-1,1-di-phosphonic acid;

a cyclohexylamine-1-hydroxy-ethylidene-phosphoryl-phosphonamide formed from cyclohexylamine present in a range of from about 10% to about 66% by weight and 1-hydroxy-ethylidene-1,1-di-phosphonic acid; and

a diethylaminoethanol-1-hydroxy-ethylidene-phosphoryl-phosphonate ester formed from diethylaminoethanol present in a range of from about 10% to about 70% by weight and 1-hydroxy-ethylidene-1,1-di-phosphonic acid,

wherein the cumulative amine to 1-hydroxy-ethylidene-1,1-di-phosphonic acid weight ratio is in the range of from about 1:1 to about 10:1.

20. The method claimed in claim 19 wherein the blend is added to boiler water to treat water in a boiler and boiler feedlines.

21. The method claimed in claim 1 comprising adding to water in a cooling tower:

a cyclohexylamine-1-hydroxy-ethylidene-phosphoryl-phosphonamide formed from cyclohexylamine and 1-hydroxy-ethylidene-diphosphonic acid and having a cyclohexylamine to 1-hydroxy-ethylidene-diphosphonic acid mole ratio in the range of from about 1:10 to about2:1, and

a copolymer, in an amount sufficient to treat the water.

Assignments (4)
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL RECORDED AT REEL 029549/FRAME 0142 Recorded Mar 15, 2017
From: ANTARES CAPITAL LP, SUCCESSOR AGENT TO GENERAL ELECTRIC CAPITAL CORPORATION
To: DUBOIS CHEMICALS, INC.
Reel/Frame 042020/0826 →
ASSIGNMENT OF INTELLECTUAL PROPERTY SECURITY AGREEMENTS Recorded Oct 9, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS RETIRING AGENT
To: ANTARES CAPITAL LP, AS SUCCESSOR AGENT
Reel/Frame 036826/0621 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Dec 31, 2012
From: KEYBANK NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
To: DUBOIS CHEMICALS, INC.
Reel/Frame 029554/0757 →
SECURITY AGREEMENT Recorded Dec 28, 2012
From: DUBOIS CHEMICALS, INC.
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS AGENT
Reel/Frame 029549/0142 →