US 11,981,611 B2
Nitrification inhibitors to improve fertilizer efficiency
Gary David McKnight, High Point, NC (US); and Randall Linwood Rayborn, Burlington, NC (US)
Assigned to SOILGENIC TECHNOLOGIES, LLC, High Point, NC (US)
Filed by Soilgenic Technologies, LLC, High Point, NC (US)
Filed on Aug. 22, 2022, as Appl. No. 17/892,963.
Application 17/892,963 is a continuation of application No. 16/154,640, filed on Oct. 8, 2018, granted, now 11,440,854.
Application 16/154,640 is a continuation in part of application No. 15/985,656, filed on May 21, 2018, granted, now 11,414,359.
Application 15/985,656 is a continuation in part of application No. 15/957,575, filed on Apr. 19, 2018, abandoned.
Application 15/957,575 is a continuation in part of application No. 15/854,319, filed on Dec. 26, 2017, granted, now 10,273,194.
Application 15/854,319 is a continuation in part of application No. 15/641,264, filed on Jul. 4, 2017, abandoned.
Claims priority of provisional application 62/358,116, filed on Jul. 4, 2016.
Prior Publication US 2023/0013743 A1, Jan. 19, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C05F 11/08 (2006.01); C05C 1/00 (2006.01); C05C 3/00 (2006.01); C05C 9/00 (2006.01); C05C 9/02 (2006.01); C05C 11/00 (2006.01); C05F 3/00 (2006.01); C05F 17/00 (2020.01); C05G 3/90 (2020.01); C05G 5/23 (2020.01); C05G 5/27 (2020.01); C05G 5/30 (2020.01); C09D 7/20 (2018.01)
CPC C05F 11/08 (2013.01) [C05C 1/00 (2013.01); C05C 3/00 (2013.01); C05C 9/00 (2013.01); C05C 9/02 (2013.01); C05C 11/00 (2013.01); C05F 3/00 (2013.01); C05F 17/00 (2013.01); C05G 3/90 (2020.02); C05G 5/23 (2020.02); C05G 5/27 (2020.02); C05G 5/30 (2020.02); C09D 7/20 (2018.01)] 20 Claims
OG exemplary drawing
 
1. A fertilizer composition comprising a) one or more solid nitrogen sources, and b) a liquid fertilizer additive composition, wherein the one or more solid nitrogen sources are nitrogen sources granules, wherein the liquid fertilizer additive composition comprises a liquid reaction composition, wherein the liquid reaction composition comprises i) one or more biodegradable polymers and/or oligomers, and ii) a reaction medium, wherein the one or more biodegradable polymers and/or oligomers comprise one or more dicyandiamide-formaldehyde reaction products, wherein the one or more dicyandiamide-formaldehyde reaction products are formed in the reaction medium, wherein the reaction medium comprises a non-aqueous polar, aprotic solvent (NAPAOL), wherein the NAPAOL comprises one or more polar, aprotic solvents selected from the group consisting of:
(1) dimethyl sulfoxide,
(2) one or more sulfoxides selected from the group consisting of (a) dialkylsulfoxide, (b) diarylsulfoxide, and (c) alkylaryl-sulfoxide having the formula:
R9S(O)xR10,
wherein R9 and R10 are each independently a C1-6 alkylene group, an aryl group, or C1-3alkylenearyl group or R9 and R10 together with the sulfur to which they are attached form a 4 to 8 membered ring wherein R9 and R10 together are a C1-6 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 is 1 or 2,
(3) one or more alkylene carbonates selected from the group consisting of ethylene carbonate, propylene carbonate and butylene carbonate,
(4) 1-Methyl-2-pyrrolidone,
(5) one or more organo phosphorous liquids selected from the group consisting of hexamethylphosphoramide and one or more trialkylphosphates selected from the group represented by the formula:

OG Complex Work Unit Chemistry
wherein:
R22 is alkyl radical —C1H3 to —C6H13
R23 is alkyl radical —C1H3 to —C6H13
R24 is alkyl radical —C1H3 to —C6H13
(6) 1,2-dimethyloxyethane,
(7) 2-methoxyethyl ether, and
(8) cyclohexylpyrrolidone,
wherein the reaction medium's properties are:
a) environmentally safe,
b) flashpoint above 145° F.,
c) safe for contact with humans and animals,
d) able to maintain the one or more dicyandiamide-formaldehyde reaction products at levels of 1-50% in down to at least 10° C., and
e) provide even delivery of the one or more dicyandiamide-formaldehyde reaction products to the surface of a fertilizer granules and to the surface of the nitrogen sources granules while not causing clumping of the granules, and
wherein said liquid fertilizer additive composition comprises 0.05-10% of the fertilizer composition.
 
16. A fertilizer composition comprising a) one or more solid nitrogen sources, and b) a liquid fertilizer additive composition, wherein the one or more solid nitrogen sources are nitrogen sources granules, wherein the liquid fertilizer additive composition comprises i) a liquid reaction composition and ii) one or more nitrification inhibitors, wherein the liquid reaction composition comprises i) one or more biodegradable polymers and/or oligomers, and ii) a reaction medium, wherein the one or more biodegradable polymers and/or oligomers comprise one or more dicyandiamide-formaldehyde reaction products, wherein the one or more dicyandiamide-formaldehyde reaction products are formed in the reaction medium, wherein the reaction medium comprises a non-aqueous polar, aprotic solvent (NAPAOL), wherein the NAPAOL comprises one or more polar, aprotic solvents selected from the group consisting of:
(1) dimethyl sulfoxide,
(2) one or more sulfoxide selected from the group consisting of (a) dialkylsulfoxide, (b) diarylsulfoxide, and (c) alkylaryl-sulfoxide having the formula:
R9S(O)xR10
wherein R9 and R10 are each independently a C1-6 alkylene group, an aryl group, or C1-3 alkylenearyl group or R9 and R10 together with the sulfur to which they are attached form a 4 to 8 membered ring wherein R9 and R10 together are a C1-6 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 is 1 or 2,
(3) one or more alkylene carbonates selected from the group consisting of ethylene carbonate, propylene carbonate and butylene carbonate
(4) 1-Methyl-2-pyrrolidone,
(5) one or more organo phosphorous liquids selected from the group consisting of hexamethylphosphoramide and one or more trialkylphosphates selected from the structure:

OG Complex Work Unit Chemistry
wherein:
R22 is an alkyl radical —C1H3 to —C6H13
R23 is an alkyl radical —C1H3 to —C6H13
R24 is an alkyl radical —C1H3 to —C6H13
(6) 1,2-dimethyloxyethane,
(7) 2-methoxyethyl ether, and
(8) cyclohexylpyrrolidone,
and wherein the one or more dicyandiamide-formaldehyde reaction products comprise one or more structures:

OG Complex Work Unit Chemistry
wherein R43, R44, R45 and R46 are one or more members independently selected from the group consisting of: H and —CH2OH wherein at least one of R43, R44, R45 and R46 is —CH2OH,

OG Complex Work Unit Chemistry
wherein R47, R48, R49 R50, R51 and R52 are one or more members independently selected from the group consisting of: H, and —CH2OH,

OG Complex Work Unit Chemistry
wherein R53, R54, R55, R56, R57, R58, R59 and R60 are one or more members independently selected from the group consisting of: H and —CH2OH, wherein said liquid fertilizer additive composition is generated under non-aqueous conditions,

OG Complex Work Unit Chemistry
wherein R61, R62, R63, R64, R65, R66, R67 and R68 are one or more members
independently selected from the group consisting of: H and —CH2OH, wherein said one or more dicyandiamide-formaldehyde reaction products are made by using non-aqueous reaction conditions, and wherein said liquid reaction composition comprises more than 10% by weight of said one or more structures.