IP Library Granted Patent US 11,021,414
Granted Patent B2
US 11,021,414 · App. 16/799,772 · Granted Jun 1, 2021

Liquid formulations of urease inhibitors for fertilizers

Inventors: Gary David McKnight (High Point, NC); David Bruce Parker (Canyon, TX); Yang Zehni (Ningbo, CN); Ray Perkins (Bakersville, NC); Wei Xu (Sugarland, TX)
C05G3/90C05C9/00C05C9/005C05C9/02C05G5/00C05G5/20C05G5/23C05G5/30C07F9/224C09K15/28
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Quick Facts
Patent No.
US 11,021,414
App. No.
16/799,772
Granted
Jun 1, 2021
Kind
B2
Abstract

An improved solvent system for the formulation and application of N-alkyl thiophosphoric triamide urease inhibitors. These formulations provide safety and performance benefits relative to existing alternatives and enable storage, transport and subsequent coating or blending with urea based or organic based fertilizers. These formulations are comprised primarily of environmentally friendly aprotic and protic solvents (particularly dimethyl sulfoxide and alcohols/polyols) to stabilize the urease inhibitor.

Claims (44)

1. A liquid fertilizer composition comprising

a. a first solution comprising urea and water,

b. a second solution comprising one or more phosphoramides and dimethyl sulfoxide,

c. optionally dicyandiamide, wherein said second solution is added to said first solution to generate said liquid fertilizer composition.

2. The liquid fertilizer composition of claim 1 , wherein the one or more phosphoramides are selected from the group consisting of aliphatic phosphoric triamides and N-alkyl thiophosphoric triamides.

3. The liquid fertilizer composition of claim 1 , wherein the one or more phosphoramides comprise N-(n-butyl) thiophosphoric triamide and wherein a weight percent ratio of N-(n-butyl) thiophosphoric triamide to said dimethyl sulfoxide comprises 5-58.9%.

4. The liquid fertilizer composition of claim 1 , wherein said composition further comprises one or more erotic solvents selected from the group consisting of a) one or more C 1 to C 6 alcohols, b) one or more polyols selected from the group consisting of alkylene glycols and poly(alkylene) glycols, wherein the one or more alkylene glycols are selected from the group consisting of ethylene glycol, propylene glycol, and butylene glycol and wherein the one or more poly(alkylene) glycols are selected from the group consisting of polymethylene glycols, polyethylene glycols, polypropylene glycols, and polybutylene glycols c) glycerin, d) one or more glycerin derivatives, e) one or more alkyl lactates selected from the group consisting of ethyl lactate, propyl lactate, and butyl lactate, and f) one or more alkanolamines selected from the group consisting of ethanolamine, diethanolamine, dipropanolamine, methyl diethanolamine, monoisopropanolamine, and triethanolamine.

5. The liquid fertilizer composition of claim 1 , wherein the liquid, fertilizer composition further comprises one or more aprotic solvents selected from the group consisting of a) one or more alkylene carbonates selected from the group consisting of propylene carbonate, ethylene carbonate, and butylene carbonate, b) 2-methoxyethyl ether, c) cyclohexylpyrrolidone, d) 1,3 dimethyl-2-imidazolidinone, e) dimethyloxyethane, and f) an organo phosphorous liquid hexamethyl phosphoramide.

6. The liquid fertilizer composition of claim 3 , wherein the weight percent ratio of N-(n-butyl) thiophosphoric triamide to dimethyl sulfoxide comprises 20-58.9%.

7. The liquid fertilizer composition of claim 1 , wherein the composition further comprises one or more surfactants.

8. The liquid fertilizer composition of claim 7 , wherein said one or more surfactants comprise nonionic surfactants with a HLB range of 6-18.

9. A liquid fertilizer composition comprising

a. a first solution comprising urea and water,

b. one or more phosphoramides,

c. a first solvent,

d. either of a second solvent or a third solvent, or both the second solvent and the third solvent,

wherein said first solvent is one or more polar aprotic solvents selected from the group consisting of

i. dimethyl sulfoxide, and

ii. one or more members selected from the group consisting of dialkyl, diaryl, or alkylaryl sulfoxide(s) of formula

R 9 S(O) x R 10

wherein

R 9 and R 10 are each independently a C 1 -C 6 alkylene group, an aryl group or C 1 -C 3 alkylenearyl group, or R 9 and R 10 with the sulfur to which they are attached form a 4 to 8 membered ring wherein R 9 and R 10 together are a C 1 -C 6 alkylene group which optionally contains one or more atoms selected from the group consisting of O, S, Se, Te, N, and P in the ring, and

x=1 or 2,

wherein said second solvent comprises one or more aprotic solvents that are not identical to the first solvent and said third solvent comprises one or more protic solvents, wherein said one or more phosphoramides is added as a second solution to said first solution, wherein said second solution comprising said one or more phosphoramides is initially dissolved in any of said first solvent, said second solvent, said third solvent, or combinations thereof,

e. optionally dicyandiamide,

to generate the liquid fertilizer composition.

10. The liquid fertilizer composition of claim 9 , wherein the one or more phosphoramides comprises N-(n-butyl) thiophosphoric triamide.

11. The liquid fertilizer composition of claim 9 , wherein a weight percent ratio of N-(n-butyl) thiophosphoric triamide to said first solvent combined with one or more members selected from the group consisting of the second solvent and the third solvent comprises 5-75%.

12. The liquid fertilizer composition of claim 9 , wherein said first solvent comprises dimethyl sulfoxide.

13. The liquid fertilizer composition of claim 9 , wherein said third solvent is selected from the group consisting of a) one or more C 1 to C 6 alcohols, b) one or more polyols selected from the group consisting of alkylene glycols and poly(alkylene) glycols, wherein the one or more alkylene glycols are selected from the group consisting of ethylene glycol, propylene glycol, and butylene glycol and wherein one or more poly(alkylene) glycols are selected from the group consisting of polymethylene glycols, polyethylene glycols, polypropylene glycols, and polybutylene glycols c) glycerin, d) one or more glycerin derivatives, e) one or more alkyl lactates selected from the group consisting of ethyl lactate, propyl lactate, and butyl lactate, and f) one or more alkanolamines selected from, the group consisting of ethanolamine, diethanolamine, dipropanolamine, methyl diethanolamine, monoisopropanolamine, and triethanolamine.

14. The liquid fertilizer composition of claim 13 , wherein said third solvent comprises polyethylene glycols.

15. The liquid fertilizer composition of claim 9 , wherein said second solvent is selected from the group consisting of a) one or more alkylene carbonates selected from the group consisting of propylene carbonate, ethylene carbonate, and butylene carbonate, b) 2-methoxyethyl ether, c) cyclohexylpyrrolidone, d) 1,3 dimethyl-2-imidazolidinone, and e) organo phosphorous liquid hexamethyl phosphoramides.

16. The liquid fertilizer composition of claim 9 , wherein the composition further comprises one or more surfactants.

17. The liquid fertilizer composition of claim 16 , wherein said one or more surfactants comprise nonionic surfactants with a HLB range of 6-18.

18. A liquid fertilizer composition comprising

a. a first solution comprising urea and water,

b. N-(n-butyl) thiophosphoric triamide,

c. dimethyl sulfoxide,

d. one or more protic solvents selected from the group consisting of polyethylene glycols, glycerin and one or more glycerin derivatives,

wherein said N-(n-butyl) thiophosphoric triamide is added as a second solution to said first solution, wherein said second solution comprises said N-(n-butyl) thiophosphoric triamide initially dissolved in any of said dimethyl sulfoxide, said one or more protic solvents, or combinations thereof, and

e. optionally dicyandiamide,

to generate the liquid fertilizer composition.

19. The liquid fertilizer composition of claim 18 , wherein a compositional weight percent ratio of N-(n-butyl) thiophosphoric triamide to dimethyl sulfoxide and polyethylene glycol comprise 5-20%.

20. The liquid fertilizer composition of claim 18 , wherein said one or more glycerin derivatives comprise esters of glycerin.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2022
From: WORLD SOURCE ENTERPRISES LLC
To: SOILGENIC TECHNOLOGIES, LLC
Reel/Frame 060592/0249 →
Continuity (6)
Continuation 16294002 · Mar 6, 2019
Continuation 15792288 · Oct 24, 2017
Continuation 15636211 · Jun 28, 2017
Continuation 13890082 · May 8, 2013
Provisional Application 61708105 · Oct 1, 2012
Related Publication 20200189990A1 · Jun 18, 2020
Cited By (3)
US 12,358,847 US 12,459,873 US 12,698,243