EP0380325A2
Expired / Lapsed
EP
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Microencapsulated agriculturally active material
Assignee: Griffin Corp
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Filing: 1990-01-24
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Granted: —
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Expires: 2010-01-24
Abstract
Abstract Agriculturally active materials, such as pesticides, herbicides and the like and a process for microencapsulating said materials. The present invention includes trifluralin having a polymorphic form characterized by a yellow color and a melting point of approximately 41°-- 43° C. The present invention also includes a method of using the yellow polymorphic form of trifluralin as a herbicide. In addition, the present invention includes a method of microencapsulating low-melting agricurally active materials, such as trifluralin. The microencapsulation process comprises the steps of heating a low-melting, water-immiscible, agricurally active material to a molten state. The molten active material is then combined with an aqueous solution of a water-soluble, film-forming polymer at a temperature sufficient to maintain the active material in its molten state. The active material is then dispersed or emulsified in the aqueous solution so that the active material has a primary particle size of between approximately 0.1 and 10 microns. The resulting dispersion or emulsion is then spray dried at a temperature between approximately 50° and 220° C. so as to microencapsulate the active material in the polymer. Compounds for promoting the rapid solidification of the active material are also disclosed.
Inventors
- 👤 John Misselbrook
- 👤 Larry J. Mckinney
- 👤 James H. Lefiles
- 👤 Edwin F. Hoff, Jr.
- 👤 Elliot Bergman
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 22:21
CPC Classifications
A; A01; A01N; A01N25/00; A01N25/08; A01N25/10; A01N25/26; A01N25/28; A01N33/00; A01N33/16; A01N33/18
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
24 words
A herbicidal composition comprising alpha, alpha, alpha-trifluoro-2,6-dinitro-N,N-di-n-propyl-p-toluidine having a polymorphic form characterised by a yellow colour and a melting point of approximately 41°-43° C.
Claim 2
Dependent Claim
24 words
A herbicidal composition comprising alpha, alpha, alpha-trifluoro-2,6-dinitro-N,N-di-n-propyl-p-toluidine having a polymorphic form characterised by a yellow colour and a melting point of approximately 41°-43° C.
Claim 3
Dependent Claim
25 words
A herbicidal composition according to claim 1, wherein said alpha, alpha, alpha-trifluoro-2,6-dinitro-N,N-di-n-propyl-p-toluidine is microencapsulated in a water-soluble microcapsule, said microcapsule substantially maintaining said polymorphic form.
Claim 4
Dependent Claim
20 words
The herbicidal composition of claim 2, wherein said microcapsule has a particle size of between approximately 10 and 500 microns.
Claim 5
Dependent Claim
104 words
A process for microencapsulating low-melting, agriculturally active materials, comprising the steps of: heating a low-melting, water immiscible, agriculturally active material to a molten state; combining said molten active material and an aqueous solution of a water-soluble, film-forming polymer at a temperature sufficient to maintain said active material in said molten state; dispersing or emulsifying said active material in said aqueous solution so that said active material has a primary particle size of between approximately 0.1 and 10 microns; and spray drying the resulting dispersion or emulsion at a temperature between about 50° and 220°C so as to microencapsulate said active material in said polymer.
Claim 6
Dependent Claim
104 words
A process for microencapsulating low-melting, agriculturally active materials, comprising the steps of: heating a low-melting, water immiscible, agriculturally active material to a molten state; combining said molten active material and an aqueous solution of a water-soluble, film-forming polymer at a temperature sufficient to maintain said active material in said molten state; dispersing or emulsifying said active material in said aqueous solution so that said active material has a primary particle size of between approximately 0.1 and 10 microns; and spray drying the resulting dispersion or emulsion at a temperature between about 50° and 220°C so as to microencapsulate said active material in said polymer.
Claim 7
Dependent Claim
26 words
The process of claim 4, further comprising the step of cooling said microencapsulated active material to a temperature below the melting point of said active material.
Claim 8
Dependent Claim
109 words
The process of claim 4, further comprising the step of combining with said aqueous solution or said molten active material, an effective amount of crystallization initiating compound selected from benzoic acid, sodium benzoate, salicylic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine; 3,5-dinitro-N⁴,N⁴-dipropylsulfanilamide, 2-dipropylamino-3, 5-dinitrobenzotrifluoride, sodium dodecylbenzene sulfonate, tetrasodium N-(1,2-dicarboxyethyl)-N-octadecylsulfosuccinamate, diotyl ester of sodium sulfosuccinic acid, sodium N-methyl-N-oleoyl taurate, sorbitan monolaurate, tetramethyl decynediol, dodecylphenol-9 mole ethoxylate, tetramethyl decynediol, polyoxyethylene (20) sorbitan monostearate, polyoxyethylene (20) soribitan triolate, polyoxyethylene (2) cetyl ether, polyoxyethylene (8) stearate, diethylene glycol monostearate, polyethylene glycol 400 monostearate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, polyoxyethylene (20) sorbitan monolaurate, polyoxyethylene (20) sorbitan monooleate, nonylphenol 4 mole ethoxylate and mixtures thereof.
Claim 9
Dependent Claim
137 words
A process according to claim 4, for microencapsulating a herbicidal composition comprising the steps of: heating a herbicidal agent comprising alpha, alpha, alpha-trifluoro-2,6-dinitro-N,N-di-n-propyl-p-toluidine to a temperature between approximately 47° and 50°C.; combining said heated herbicidal agent and an aqueous solution of between approximately 1% and 50% by weight of a partially hydrolyzed polyvinyl acetate, said polyvinyl acetate having a degree of hydrolysis of between approximately 75% and 99% and a molecular weight of between approximately 10,000 and 100,000 at a temperature between approximately 50° and 100° C.; emulsifying said herbicidal agent in said solution so that said herbicidal composition has a primary particle size of between approximately 0.1 and 10 microns; and spray drying said emulsion at a temperature between approximately 50° and 220° C so as to encapsulate said herbicidal agent in microcapsules of polyvinyl alcohol.
Claim 10
Dependent Claim
22 words
The process of claim 7, further comprising the step of cooling said microcapsules to a temperature between approximately -20° and 30° C.
Claim 11
Dependent Claim
49 words
The process of claim 7, further comprising the step of heating and cooling said microcapsules to a temperature and for a period of time sufficient to substantially convert said herbicidal agent to a polymorphic form characterised by a yellow colour and a melting point of approximately 41° -43° C.
Claim 12
Dependent Claim
67 words
The process of claim 7, further comprising the step of combining with said aqueous solution or said molten active material, an effective amount of a compound selected from the group consisting of polyoxyethylene (2) cetyl ether, polyoxyethylene (8) stearate, diethylene glycol monostearate, polyethylene glycol 400 monostearate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, polyoxyethylene (20) sorbitan monolaurate, polyoxyethylene (20) sorbitan monooleate, nonylphenol 4 mole ethoxylate and mixtures thereof.
Claim 13
Dependent Claim
36 words
The process of claim 7, further comprising the steps of packaging said microencapsulated herbicidal agent while said herbicidal agent is still molten and cooling said packaged product to a temperature between approximately -20° and 30° C.
Claim 14
Dependent Claim
40 words
The process of claim 7, further comprising the steps of packaging said microencapsulated herbicidal agent, heating said packaged product so that said herbicidal agent is remelted and cooling said packaged product to a temperature between approximately -20° and 30° C.
Claim 15
Dependent Claim
70 words
A process for microencapsulating agriculturally active materials comprising the steps of: grinding a high-melting, water-immiscible active material to a primary particle size of between approximately 0.1 and 10 microns; combining said ground active material and an aqueous solution of a water-soluble, film-forming polymer; and spray drying the resulting dispersion or emulsion at a temperature between about 50° and 220° C so as to microencapsulate said active material in said polymer.
Claim 16
Dependent Claim
70 words
A process for microencapsulating agriculturally active materials comprising the steps of: grinding a high-melting, water-immiscible active material to a primary particle size of between approximately 0.1 and 10 microns; combining said ground active material and an aqueous solution of a water-soluble, film-forming polymer; and spray drying the resulting dispersion or emulsion at a temperature between about 50° and 220° C so as to microencapsulate said active material in said polymer.
Claim 17
Dependent Claim
22 words
A method of controlling weeds comprising the step of applying to soil effective amount of a herbicidal composition according to claim 1.
Claim 18
Independent Claim
84 words
A method of reducing nitrosamine impurities in herbicides comprising the steps of: dispersing or emulsifying a water-immiscible nitrosamine-containing herbicide in an aqueous solution or dispersion of a water-soluble, film-forming polymer such that said dispersed or emulsified herbicide has a particle size between approximately 0.1 and 10 microns; and spray drying the resulting dispersion or emulsion at a temperature between about 50° and 220° C so as to microencapsulate said herbicide in said polymer, whereby the amount of nitrosamine in said microencapsulated herbicide is reduced.
Claim 19
Independent Claim
84 words
A method of reducing nitrosamine impurities in herbicides comprising the steps of: dispersing or emulsifying a water-immiscible nitrosamine-containing herbicide in an aqueous solution or dispersion of a water-soluble, film-forming polymer such that said dispersed or emulsified herbicide has a particle size between approximately 0.1 and 10 microns; and spray drying the resulting dispersion or emulsion at a temperature between about 50° and 220° C so as to microencapsulate said herbicide in said polymer, whereby the amount of nitrosamine in said microencapsulated herbicide is reduced.
Claim 20
Dependent Claim
125 words
A process for converting active materials which exhibit more than one or more heat-alterable polymorphic forms from one polymorphic form to a desired polymorphic form comprising steps of: heating a water-immiscible active material which exhibits two or more heat-alterable polymorphic forms, said active material being in one polymorphic form prior to heating; combining said active material and an aqueous solution of a water-soluble, film-forming polymer, dispersing or emulsifying said active material in said aqueous solution so that said active material has a primary particle size of between 0.1 and 10 microns; spray drying the resulting dispersion or emulsion so as to microencapsulate said active material in said polymer, and cooling said microencapsulated active material, whereby said microencapsulated active material is in another desired polymorphic state.
Claim 21
Dependent Claim
125 words
A process for converting active materials which exhibit more than one or more heat-alterable polymorphic forms from one polymorphic form to a desired polymorphic form comprising steps of: heating a water-immiscible active material which exhibits two or more heat-alterable polymorphic forms, said active material being in one polymorphic form prior to heating; combining said active material and an aqueous solution of a water-soluble, film-forming polymer, dispersing or emulsifying said active material in said aqueous solution so that said active material has a primary particle size of between 0.1 and 10 microns; spray drying the resulting dispersion or emulsion so as to microencapsulate said active material in said polymer, and cooling said microencapsulated active material, whereby said microencapsulated active material is in another desired polymorphic state.
Claim 22
Dependent Claim
34 words
A fungicidal composition comprising tetrachloroisophthalonitrile having a polymorphic form characterised by a white colour and a melting point of approximately 251° C microencapsulated in a water-soluble microcapsule, said microcapsule substantially maintaining said polymorphic form.
Claim 23
Dependent Claim
34 words
A fungicidal composition comprising tetrachloroisophthalonitrile having a polymorphic form characterised by a white colour and a melting point of approximately 251° C microencapsulated in a water-soluble microcapsule, said microcapsule substantially maintaining said polymorphic form.
Claim 24
Independent Claim
138 words
A method of controlling pests comprising the step of applying to said pests an effective amount of a polymorphic pesticide selected from the group consisting of alpha, alpha, alpha-trifluro-2, 6-dinitro-N,N-di-n-propyl-p-toluidine in a polymorphic form characterised by a yellow colour and a melting point of approximately 41° -43° C; N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine in a polymorphic form characterised by a yellow colour and a melting point of approximately 52° -55°C; tetrachlorosisophthalonitrile in a polymorphic form characterised by a white colour and a melting point of approximately 251°C;methyl-N,N-dimethyl-N-[(methylcarbomyl)oxy]-1-thiooxamimidate having a polymorphic form characterised by a white colour and a melting point of approximately 101° -102°C; 4-hydroxy-3,5-diiodobenzonitrile octanoate having a polymorphic form characterised by a tan colour and a melting point of approximately 53° -56°C and 2-chloro-4-ethylamino-6-isopropylamino-S-triazine having a polymorphic form characterised by a white colour and a melting point of approximately 174° -178oC.
Claim 25
Independent Claim
138 words
A method of controlling pests comprising the step of applying to said pests an effective amount of a polymorphic pesticide selected from the group consisting of alpha, alpha, alpha-trifluro-2, 6-dinitro-N,N-di-n-propyl-p-toluidine in a polymorphic form characterised by a yellow colour and a melting point of approximately 41° -43° C; N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine in a polymorphic form characterised by a yellow colour and a melting point of approximately 52° -55°C; tetrachlorosisophthalonitrile in a polymorphic form characterised by a white colour and a melting point of approximately 251°C;methyl-N,N-dimethyl-N-[(methylcarbomyl)oxy]-1-thiooxamimidate having a polymorphic form characterised by a white colour and a melting point of approximately 101° -102°C; 4-hydroxy-3,5-diiodobenzonitrile octanoate having a polymorphic form characterised by a tan colour and a melting point of approximately 53° -56°C and 2-chloro-4-ethylamino-6-isopropylamino-S-triazine having a polymorphic form characterised by a white colour and a melting point of approximately 174° -178oC.
Claim 26
Dependent Claim
34 words
A pesticidal composition comprising 4-hydroxy-3,5-diiodobenzonitrile ocanoate having a polymorphic form characterised by a tan colour and a melting point of approximately 53°-56°C microencapsulated in a water-soluble microcapsule, said microcapsule substantially maintaining said polymorphic form.
Claim 27
Dependent Claim
34 words
A pesticidal composition comprising 4-hydroxy-3,5-diiodobenzonitrile ocanoate having a polymorphic form characterised by a tan colour and a melting point of approximately 53°-56°C microencapsulated in a water-soluble microcapsule, said microcapsule substantially maintaining said polymorphic form.
Claim 28
Dependent Claim
33 words
A pesticidal composition comprising 2-chloro-4-ethylamino-6-isopropylamino-S-triazine having a polymorphic form characterised by a white colour and a melting point of approximately 174°-178°C microencapsulated in a water-soluble microcapsule, said microcapsule substantially maintaining said polymorphic form.
Claim 29
Dependent Claim
33 words
A pesticidal composition comprising 2-chloro-4-ethylamino-6-isopropylamino-S-triazine having a polymorphic form characterised by a white colour and a melting point of approximately 174°-178°C microencapsulated in a water-soluble microcapsule, said microcapsule substantially maintaining said polymorphic form.
Claim 30
Dependent Claim
20 words
A pesticidal composition comprising trifluralin and an effective amount of sodium dodecylbenzene sulfonate microencapsulated in a microcapsule of polyvinyl alcohol.
Claim 31
Dependent Claim
20 words
A pesticidal composition comprising trifluralin and an effective amount of sodium dodecylbenzene sulfonate microencapsulated in a microcapsule of polyvinyl alcohol.
Claim 32
Dependent Claim
11 words
A pesticidal composition comprising 2-chloro-2′,6′-diethyl-N-(methoxymethyl) acetanilide microencapsulated in a water-soluble microcapsule.
Claim 33
Dependent Claim
11 words
A pesticidal composition comprising 2-chloro-2′,6′-diethyl-N-(methoxymethyl) acetanilide microencapsulated in a water-soluble microcapsule.
Claim 34
Dependent Claim
33 words
A pesticidal composition comprising N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine having a polymorphic form characterised by a yellow colour and a melting point of approximately 52°-55°C microencapsulated in a water-soluble microcapsule, said microcapsule substantially maintaining said polymorphic form.
Claim 35
Dependent Claim
33 words
A pesticidal composition comprising N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine having a polymorphic form characterised by a yellow colour and a melting point of approximately 52°-55°C microencapsulated in a water-soluble microcapsule, said microcapsule substantially maintaining said polymorphic form.
References Cited (Backward Citations)
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