WO2019068914A1 - Formulations comprenant des tensioactifs, des liquides organiques et des améliorants de viscosité - Google Patents

Formulations comprenant des tensioactifs, des liquides organiques et des améliorants de viscosité Download PDF

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WO2019068914A1
WO2019068914A1 PCT/EP2018/077227 EP2018077227W WO2019068914A1 WO 2019068914 A1 WO2019068914 A1 WO 2019068914A1 EP 2018077227 W EP2018077227 W EP 2018077227W WO 2019068914 A1 WO2019068914 A1 WO 2019068914A1
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formulation
surfactant
carbon atoms
linear
branched
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PCT/EP2018/077227
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English (en)
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Pascal Herve
Matthieu Guirardel
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Rhodia Operations
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents

Definitions

  • Formulations comprising surfactants, organic liquids and viscosifiers
  • the present invention relates to formulations comprising surfactants
  • compositions comprising biologically active ingredients, for example compositions comprising pharmaceutically active compositions and agriculturally active compositions.
  • insecticides, fungicides, herbicides, miticides and plant growth regulators as well as tank-mix adjuvants or fertilizers are generally produced in pure or highly concentrated form. However, they are to be used on agricultural operation sites in low concentration. To this end, they are usually formulated with other ingredients that enable easy dilution by the farm operator. The dilution is generally performed by mixing the agricultural concentrated formulation with water.
  • EC emulsifiable concentrates
  • SC suspensions concentrates
  • oil dispersions consists in a suspension of active material(s) in an apolar medium, generally an oily fluid intended to be diluted with water before use.
  • WO 2013/043678 discloses some concentrate formulations that can be readily combined with pesticide to form an oil dispersion which subsequently may be diluted, in particular by a farm operator, with water to form the corresponding pesticide emulsion.
  • These prior art formulations include as oily vehicle at least one vegetable oil alkyl ester.
  • WO 2016/142518 discloses concentrate formulations comprising at least 20 % by weight of at least one non-ionic surfactant chosen from
  • polyethylene glycol esters of fatty acids surfactants relative to the total weight of the concentrate formulation, a liquid medium wholly or partly formed from at least one non esterified vegetable oil or mixtures thereof, at least one phyllosilicate, said phyllosilicate being present in a content of less than or equal to 5 % by weight relative to the total weight of the concentrate formulation and at least one activator of said phyllosilicate.
  • a further embodiment of the invention is directed to the use of the
  • a still further embodiment of the invention relates to a method for
  • preventing or combatting diseases in animals such as mammals, or for preventing or combatting infestation of plants by pests and/or of regulating plant growth, comprising the application of a mixture obtained by diluting a formulation according to the invention which additionally comprises a biologically active ingredient.
  • formulation mean a formulation that forms an emulsion when diluted into water and mixed by inversion of the vial.
  • CIPAC MT36 and MT180 inversions of the vial
  • stable meaning that no or only little phase separation of cream is observed
  • the formulations in accordance with the invention comprise as component a) at least 3 wt%, based on the total weight of the formulation, of at least one surfactant S.
  • the formulation comprises from 3 to 50, preferably from 5 to 40 and more preferably from 10 to 35 wt% of the surfactant S.
  • the surfactant S comprises at least two C2-C10 oxyalkylene units.
  • the surfactant S which is comprised in the invented formulation is free of aromatic ring.
  • the invented formulation is either free of any surfactant S * comprising one or more aromatic rings (whatever alkoxylated or not), or comprises at least one surfactant S * comprising one or more aromatic rings in an amount that does not exceed 10 wt.%, based on the total weight of surfactant S and surfactant S * .
  • the invented formulation is either free of any surfactant S * comprising one or more aromatic rings, or comprises at least one surfactant S * comprising one or more aromatic rings in an amount that does not exceed 3 wt.%, based on the total weight of surfactant S and surfactant S * .
  • the invented formulation is essentially free or is free of any surfactant S * comprising one or more aromatic rings.
  • the invented formulation is free of any surfactant S * comprising one or more aromatic rings.
  • aromatic rings include aromatic rings (such as benzene ring) or heteroaromatic rings (such as furan ring).
  • aromatic rings include aromatic rings that are available as single rings (such as benzene ring) and aromatic rings that are part of fused ring systems (such as naphthalene ring).
  • optional surfactants S *1 comprising at least two C2-C10 oxyalkylene units but comprising one or more aromatic rings (such as nonylphenol ethoxylates) can only be incorporated in the invented formulation to the extent that their content in the formulation does not exceed 10 wt.%, based on the total weight of surfactant S and surfactant S * .
  • optional surfactants S *2 which are free of oxyalkylene units and which comprise one or more aromatic rings (such as sodium dodecylbenzene sulfonate).
  • surfactant means a compound that, when present in water, lowers the surface tension of water. Surfactants may act as detergents, wetting agents, surfactants, foaming agents, and dispersants.
  • Surfactants S can be generally grouped into ionic and non-ionic
  • the surfactant S is advantageously selected from the group consisting of anionic surfactants, cationic surfactants, non-ionic surfactants, amphoteric surfactants and mixtures thereof.
  • the surfactant S is preferably selected from non-ionic surfactants and from mixtures of at least one non-ionic surfactant with at least one cationic surfactant, it being understood that the aforesaid non-ionic and cationic surfactants each comprise at least two C2-C10 oxyalkylene units and are free of any aromatic ring.
  • the surfactant S is more preferably is preferably selected from non-ionic surfactants.
  • an oxyalkylene moiety also referred to as
  • alkylene oxide moiety
  • r is C2-C10 alkylene.
  • Divalent group r can be linear or branched. In the surfactant S, it is preferred that divalent group r is linear.
  • Divalent group r is preferably a C2-C6 group, such as n-hexylene, n- pentylene, n-butylene, n-propylene or ethylene. It is more preferably selected from the group consisting of n-propylene (-CH2-CH2-CH2-), ethylene (-CH2-CH2-) and mixtures thereof. Still more preferably, it is ethylene, and the corresponding oxyalkylene moiety is known as ethylene oxide or oxyethylene (-CH2-CH2-O-).
  • the total number of oxyalkylene moieties in the surfactant S may vary to a large extent, and will be easily optimized by the skilled person depending on the chemical nature of the non-oxyalkylene moieties which the surfactant S may also comprise.
  • the total number of oxyalkylene moieties in the surfactant S can be of at least 3, at least 4, at least 6, at least 8, at least 12, at least 16, at least 20, at least 50, at least 200 or at least 1000.
  • the total number of oxyalkylene moieties in the surfactant S can be of at most 5000, at most 1000, at most 200, at most 50, at most 20, at most 16, at most 12 or at most 8. Any ranges of values for the total number of oxyalkylene moieties obtained by combining any above cited lower limit with any above cited upper limit should be considered as herein clearly and unambiguously described.
  • the surfactant S may contain from 0 up to at most 4, at most 3, at most 2 or at most 1 carbon atom(s) other than the carbon atoms contained in its oxyalkylene units -r-O-
  • the surfactant S may be essentially free or completely free of carbon atoms other than the carbon atoms contained in its oxyalkylene units -r-O-.
  • the hereinafter described poly(alkylene oxide)s often meet these features.
  • the surfactant S may further contain at least 6, at least 8, at least 10, at least 12, at least 14, at least 16, at least 18 or at least 20 carbon atoms other than the carbon atoms contained in its oxyalkylene units -r-O-; the hereinafter described emulsifiers often meet these features.
  • the surfactant S may contain carbon atoms other than the carbon atoms contained in its oxyalkylene units -r-O- in an amount not exceeding 40, 30, 25, 20, 18 or 16 carbon atoms.
  • the surfactant S is advantageously free of ethylenic unsaturation.
  • the surfactant S is an ionic surfactant.
  • Ionic surfactants can be characterized by the ionic nature of at least part of their hydrophilic moiety (possibly, all) their hydrophilic moiety(-ies).
  • Ionic surfactants suitable as surfactants S are of mixed ionic-non ionic nature, in that they comprise at least one non ionic moiety (namely the oxyalkylene units) in addition to the at least one ionic moiety; said non ionic moiety is optionally directly connected to said ionic moiety.
  • the ionic surfactant S which can be cationic or anionic, further includes at least one non-ionic hydrophilic moiety.
  • the additional non ionic moiety is directly connected to an ionic moiety of the ionic surfactant S, and can therefore form a combination of hydrophilic moieties of mixed ionic-non ionic nature, such as in oxyalkylene sulfates of formula -O-A y -SO3 " wherein A denotes an oxyalkylene unit (e.g.
  • the non ionic moiety consists generally of one or more C2-C10, preferably C2-C 4 oxyalkylene units, preferably oxyethylene and/or oxypropylene units, and more preferably oxyethylene units.
  • the total number of oxyalkylene units in the ionic surfactant is in this case preferably of from 2 to 50, preferably of from 3 to 25 and even more preferably of from 4 to 12.
  • Exemplary representatives of alkoxylated ionic surfactants S are ether carboxylates of formula R-O-Ay-Ch -COOX wherein R is C8-C20 alkyl or C8-C20 alkenyl (such as oleyl), A is a C2-Ciooxyalkylene unit (e.g. CH2CH2O), X is ammonium or an alkali metal and y ranges from 2 to 50.
  • ester carboxylates of a di-, tri- or tetracarboxylic acid are obtainable by the condensation reaction of an alcohol with the di-, tri- or tetracarboxylic acid (e.g. glycolic acid, citric acid or tetrabutane carboxylic acid), wherein the alcohol has been previously alkoxylated.
  • an alcohol e.g. glycolic acid, citric acid or tetrabutane carboxylic acid
  • ether sulfonates of formula R-O-A y -CH 2 -SO 3 X wherein R is C 8 -C 2 o alkyl or C8-C20 alkenyl (such as oleyl), A is a C2-C10 oxyalkylene unit (e.g.
  • X is ammonium or an alkali metal and y ranges from 2 to 50,
  • X is ammonium or an alkali metal and y ranges from 2 to 50,
  • R is C8-C20 alkyl or C8-C20 alkenyl (such as oleyl)
  • A is a oxyalkylene unit (e.g. CH2CH2O)
  • X and X' are independently ammonium or an alkali metal and y ranges from 2 to 50, and
  • surfactants S are or include a non-ionic surfactant, and same will now be described in some more detail.
  • Non-ionic surfactants S are advantageously selected from the group
  • ether-based non-ionic surfactants consisting of ether-based non-ionic surfactants, ester-based non-ionic surfactants, amine-based non-ionic surfactants, amide-based non-ionic surfactants, fluoro-surfactants and mixtures thereof.
  • poly(alkylene oxide)s suitable for use in the present invention are polymers essentially all or all the repeating units of which comply with general formula -r-O- wherein r represents a divalent alkylene group having from 2 to 10 carbon atoms. Such poly(alkylene oxide)s may be terminated by a hydroxyl group.
  • Particularly suitable poly(alkylene oxide)s are those wherein r has from 2 to 4 carbon atoms, preferably from 2 to 3 carbon atoms, more preferably 2 carbon atoms.
  • the poly(alkylene oxide)s may be either linear or branched. Linear poly(alkylene oxides) are generally preferred.
  • poly(alkylene oxide)s include
  • polyoxyalkylene polyols such as polyoxyethylene glycol [also known as poly(ethylene glycol) or poly(ethylene oxide)], polyoxyethylene triol, polyoxyethylene tetraol, polyoxypropylene glycol [also commonly referred to as poly(propylene glycol) or poly(propylene oxide)], polyoxypropylene triol, polyoxypropylene tetraol, polyoxybutylene glycol, polyoxypentylene glycol, polyoxyhexylene glycol, polyoxyheptylene glycol, and
  • polyoxyoctylene glycol polyoxyoctylene glycol. These polymers may be used either individually or in combinations of two or more; for example, it can be cited random copolymers of ethylene oxide and propylene oxide, and poly(ethylene oxide)-poly(propylene oxide) block copolymers.
  • the hydroxyl end groups of the poly(alkylene oxide)s may according to a preferred embodiment be partly or fully substituted by alkoxide groups, preferably methoxy or alkoxy.
  • alkoxide groups preferably methoxy or alkoxy.
  • Suitable oxyalkylene-containing compounds suitable as surfactants S in the formulation in accordance with the instant invention are amine- terminated poly(alkylene oxide)s, in particular amine-terminated
  • poly(ethylene oxide)s or amine-terminated poly(propylene oxide)s including copolymers comprising both mentioned types of oxyalkylene units which are commercially available under the tradename Jeffamine ® from Huntsman Chemical Corporation.
  • the molecular weight of the poly(alkylene oxide)s in accordance with this embodiment may cover a wide range as discussed above generally for surfactants S.
  • poly(alkylene oxide)s having a number average or weight average molecular weight of at least 20,000, preferably at least 200,000 and even more preferably at least 1 ,000,000 are advantageous.
  • average molecular weights of at most 20,000, preferably at most 10,000 and even more preferably at most 1000 are useful.
  • the molecular weight of the suitable poly(alkylene oxides) may also be optimized in view of the specific application case. For example, a methoxy-terminated poly(ethylene oxide) having a number average or a weight average molecular weight of at most 2,000 may be used.
  • Copolymers comprising oxyethylene and oxypropylene units in random or block distribution may also be suitable and respective products are commercially available under the tradename Pluronics ® from BASF.
  • the surfactant S can consist essentially of or consist of at least one hydrophilic block and at least one lipophilic block.
  • the surfactant S comprises advantageously up to four hydrophilic first blocks and up to four lipophilic blocks.
  • the surfactant S comprises 1 or 2 hydrophilic first blocks and 1 or 2 lipophilic blocks.
  • Many surfactants S in accordance with the present invention have one and only one hydrophilic first block and one and only one lipophilic block. Certain substances among such surfactants S may qualify as emulsifiers.
  • the surfactant S may be chosen from ether based alkoxylated non ionic surfactants. Ethers of carboxylic acids-based non-ionic surfactants, alcohol-based non-ionic surfactants, oside-based non-ionic surfactants and silicone non-ionic surfactants may be mentioned as examples of such surfactants.
  • non-ionic surfactants S of interest are ethers of carboxylic acids having the following formula :
  • R 0 is C 8 -C 2 o alkyl or C 8 -C 2 o alkenyl
  • R is C2-C10 alkylene, for example -CH2-CH2-, -CH2-CH2-CH2- or a mixture thereof, and y ranges from 2 to 50.
  • ethers of carboxylic acids-based non-ionic surfactants are preferably represented by polyoxyethylene-based non-ionic surfactants, polyoxypropylene-based non-ionic surfactants, and polyoxyethylene- polyoxypropylene-based non-ionic surfactants.
  • a polyoxyethylene-based non-ionic surfactant may be a polyoxyethylene alkyl ether or a
  • polyoxyethylene alkyl ethers include compounds such as polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene octyl ether, polyoxyethylene oleyl ether, polyoxyethylene stearyl ether, polyoxyethylene isostearyl ether.
  • Alcohol-based non-ionic surfactants of interest in accordance with the present invention may be represented by alkoxylated alcohols.
  • alkoxylated relies upon the presence of oxyalkylene units, for which the total number of these units generally ranges from 2 to 50, preferably from 3 to 25, preferably from 4 to 12, preferably from 2 to 10, most preferably from 2 to 6 or, in accordance witn another embodiment, preferably from 10 to 50, most preferably from 10 to 35.
  • Alkoxylated alcohols of interest may be represented by a compound of the general formula as follows:
  • R 2 is C6-C30 alkyl or C6-C30 alkenyl, preferably C8-C20 alkyl or Cs- C20 alkenyl, more preferably lauryl or myristyl or palmityl
  • R 22 is C2-C10 alkylene, for example -CH2-CH2-, -CH2-CH2-CH2- or a mixture thereof, and y ranges from 2 to 50.
  • alkoxylated alcohols suitable as a non-ionic surfactant S are the products of the condensation of (i) from 2 to 50 moles of at least one C2-C3 alkylene oxide, such as ethylene oxide, with (ii) a mole of a saturated or unsaturated (preferably ethylenically unsaturated) fatty alcohol, especially a C8-C20 alcohol chosen from lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, linoleyl alcohol, linolenyl alcohol, oxoalcohols and mixtures thereof.
  • a saturated or unsaturated (preferably ethylenically unsaturated) fatty alcohol especially a C8-C20 alcohol chosen from lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, linoleyl alcohol, linolenyl alcohol, oxoalcohols and mixtures thereof
  • Alcoxylated alcohols may be commercially available under the tradenames Brij ® (Atlas Chemical Co.), Genapol ® (Clariant) and Lutensol ® (BASF).
  • ester-based non-ionic surfactants of interest as surfactants S one may cite alkoxylated oils and fats. These compounds encompass ethoxylated and/or propoxylated derivatives of lanolin (wool fat) or of castor oil.
  • Lanolin is the generic name of a wax containing a mixture of esters and polyesters of high-molecular-weight alcohols and fatty acids.
  • Castor oil is a mixture of a triglyceride of fatty acids.
  • ester-based non-ionic surfactants may be represented by alkoxylated acids, such as the compounds represented by monoesters and diesters.
  • Monoesters of interest as surfactants S may be represented by a
  • R 3 is C6-C30 alkyl or C6-C30 alkenyl, preferably C8-C20 alkyl or Cs- C20 alkenyl
  • R 32 is C2-C10 alkylene, for example -CH2-CH2-, -CH2-CH2-CH2- or a mixture thereof, and y ranges from 2 to 50.
  • alkoxylated acid monoesters are the condensation products of from 2 to 50 moles (in particular, from 4 to 16 moles) of an alkylene oxide (such as ethylene oxide) with one mole of a saturated or
  • unsaturated fatty acid chosen from lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid and mixtures therof.
  • Deplastol ® product which is a condensate of about 4-5 mol oxyethylene units with lauric acid and/or myristic acid (Cognis, Germany). Corresponding propoxylated and/or butylated fatty acids may also be included in the alkoxylated acids monoesters of interest.
  • Diesters of interest may be represented by a compound of the general formula as follows
  • R 4 and R 43 are independently a C6-C30 alkyl or C6-C3o alkenyl, preferably a C8-C20 alkyl or C8-C20 alkenyl
  • R 42 is C2-C10 alkylene, for example -CH2-CH2-, -CH2-CH2-CH2- or a mixture thereof, and y ranges from 2 to 50.
  • ester-based non-ionic surfactants of interest may include
  • alkoxylated glycol such as alkoxylated ethylene glycol esters and alkoxylated propylene glycol esters.
  • Alkoxylated ethylene glycol respectively propylene glycol esters may be represented by a compound of the general formula as follows
  • R 5 is C6-C30 alkyl or C6-C30 alkenyl, preferably C8-C20 alkyl or Cs- C20 alkenyl
  • R 52 is hydrogen or methyl
  • R 53 is C2-C10 alkylene, for example -CH2-CH2-, -CH2-CH2-CH2-, -CH 2 -CH(CH 3 )- or a mixture thereof, and y ranges from 2 to 50.
  • Alkoxylated esters of monoglycerides, dialkoxylated esters of diglycerides and trialkoxylated esters of triglycerides may also be compounds of interest, said esters being the reaction products of glycerol, or one of its derivatives, with a carboxylic acid comprising from 8 to 20 carbon atoms and comprise in total from 6 to 60 oxyalkylene units.
  • non limitating ester-based non-ionic surfactants one may cite polyoxyethylene alkylesters, polyoxyethylene glycerine aliphatic acid esters, polyoxyethylene castor oil, polyoxyethylene sorbitol aliphatic acid esters, polyethylene glycols aliphatic acid esters, polyoxyethylene sorbitan aliphatic esters, polyethylene glycol fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbit fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene castor oil, polyoxyethylene cured castor oil, polyoxyethylene cured castor oil fatty acid ester, polyoxyalkylenated fatty acid esters, oxyalkylenated alkyl polyglycosides.
  • polyoxyethylene glycerin fatty acid esters one may cite polyoxyethylene hydrogenated castor oil, polyoxyethylene castor oil, polyoxyethylene glyceryl monostearate, polyoxyethylene glyceryl monooleate, and polyoxyethylene glyceryl monoisostearate.
  • polyethylene glycol fatty acid esters one may cite polyethylene glycol monostearate, polyethylene glycol monooleate and polyethylene glycol monolaurate.
  • Amine-based or amide based non-ionic surfactants are alo suitable and polyoxyethylene alkylamides or polyoxyethylene aliphatic acid amides may be mentioned in this regard.
  • surfactants S in accordance with the present invention may be any surfactants S in accordance with the present invention.
  • alkoxylated alkanolamides such as alkoxylated
  • Particularly preferred as surfactants in the formulations according to the invention are polyethylene glycol esters of fatty acids.
  • polyethylene glycol fatty acid monoesters and polyethylene glycol fatty acid diesters are typically mono- and di-esters of polyethylene glycols and saturated or unsaturated (C8-C22), more typically (C12-C18), fatty acids and mixtures thereof, such as for example, poly(ethylene glycol) monomyristates, poly(ethylene glycol)
  • poly(ethylene glycol) distearates poly(ethylene glycol) monooleates, poly(ethylene glycol) dioleates, poly(ethylene glycol) linolenates, poly(ethylene glycol) dibehenates, poly(ethylene glycol) monobehenates, poly(ethylene glycol) monoerucates, and their mixtures.
  • Alkamuls ® AP commercialized by Solvay under the names Alkamuls ® AP, Alkamuls ® A, Alkamuls ® VO/2003 and Alkamuls ® VO2005.
  • Alkamuls ® VO/2003 and Alkamuls ® VO2005 are particularly preferred according to the present invention.
  • the specific surfactant S used according to the invention contributes to the obtention of a pourable formulation, and facilitates emulsification when the formulation is placed in the presence of water. It also provides stabilization over time of the so-formed emulsion by limiting, or even avoiding, phase separation.
  • the formulations according to the invention comprise an organic liquid or, more generally, an organic liquid medium.
  • liquid medium means a medium that is in the liquid phase at room temperature and a pressure of one
  • the organic liquid used in the formulation according to the invention is a good solvent and can be a polar solvent or a mixture of a polar solvent and an apolar solvent.
  • alcohols having from 1 to 10 carbon atoms preferably selected from methanol, ethanol, isopropanol, butanol, isobutanol, diethylene glycol, butylene glycol, methyl propane diol or ethylhexanol may be mentioned here.
  • Augeo ® SL191 which is a racemic mixture of (+/-)-2,2-dimethyl-4- hydroxymethyl-1 ,3-dioxolane also known as isopropylidene glycerol.
  • alkyl esters having from 2 to 12
  • carbon atoms preferably selected from ethyl acetate, propyl acetate, butyl acetate, hexyl acetate, octyl acetate or from mixtures of (i) alcohols having from 1 to 10 carbon atoms (preferably selected from methanol, ethanol, isopropanol, butanol, isobutanol, diethylene glycol, butylene glycol, methyl propane diol, ethylhexanol), (ii) alkyl esters having from 2 to 12 carbon atoms (preferably selected from ethyl acetate, propyl acetate, butyl acetate, hexyl acetate, octyl acetate) and (iii) acetal derivatives having from 2 to 12 carbon atoms (preferably selected from the Augeo ® family of solvents (available from Solvay SA) such as Augeo ® SL191 which is a racemic mixture (+/-
  • Preferred organic liquids as component b) are non-esterified vegetable oils or mixtures thereof.
  • non-esterified vegetable oil means a native vegetable oil that is chemically not transformed and in particular not esterified. In other words, it is equivalent to its natural form.
  • non-esterified vegetable oils are understood to be triglycerides or mixtures of triglycerides.
  • this vegetable oil or mixtures thereof constitutes the
  • liquid phase of the formulation is dedicated to vehicle at least the surfactant S and the viscosifier.
  • These vegetable oils may be selected for example from the group consisting of:
  • soybean oil consisting of soybean oil, corn oil, cottonseed oil, sunflower oil, maize oil, rice oil, olive oil, linseed oil, rapeseed oil, canola oil, palm oil, coconut oil and mixtures thereof.
  • Rapeseed oil, canola oil, soybean oil and corn oil are particularly desirable
  • the formulation according to the invention may preferably contain from 10 to 90 % by weight, for instance from 40 to 85 % by weight, in particular from 40 to 80 % by weight, for instance from 50 to 75 % by weight relative to its total weight, of at least one organic liquid as component b), and in particular of a non-esterified vegetable oil or mixtures thereof.
  • compositions according to the invention comprise as component c) at least 0.1 wt% of at least one viscosifier selected from N- hydrocarbyldiamides of general formula (I)
  • R a or R b is selected from hydrogen or a linear, branched or cyclic, saturated or unsaturated, hydrocarbon chain having from 1 to 40 carbon atoms, with the proviso that either R a or R b is hydrogen,
  • R c is a cyclic or branched, saturated or unsaturated, hydrocarbon aliphatic chain having from 2 to 25 carbon atoms.
  • the viscosifier is a N-hydrocarbyldiamide composition
  • the viscosifier is a N-hydrocarbyldiamide composition
  • R 1 is selected from linear or branched or cyclic, saturated or unsaturated, hydrocarbon chains having from 1 to 40 carbon atoms,
  • R 2 is selected from linear or branched, saturated or unsaturated, hydrocarbon aliphatic chains having from 1 to 15 carbon atoms
  • R 3 is selected from linear or branched alkyl groups with 1 to 8 carbon atoms
  • R 4 is selected from linear or branched or cyclic, saturated or unsaturated, hydrocarbon chains having from 1 to 40 carbon atoms,
  • R 5 is selected from linear or branched, saturated or unsaturated, hydrocarbon aliphatic chains having from 1 to 15 carbon atoms, and
  • R 6 is selected from linear or branched alkyl groups with 1 to 8 carbon atoms.
  • R a or R b is selected from hydrogen or a linear, branched or cyclic, saturated or unsaturated, hydrocarbon chain having from 1 to 40 carbon atoms, with the proviso that one and only one of R a or R b is hydrogen.
  • R c in formula (I) is a cyclic or branched, saturated or unsaturated
  • hydrocarbon aliphatic chain having from 2 to 25 carbon atoms.
  • hydrocarbon chain is to be understood as a hydrocarbon chain comprising carbon atoms and hydrogen atoms, wherein said hydrocarbon chain may optionally be substituted by one or more heteroatoms, such as oxygen atoms.
  • aliphatic chain is to be understood as a non-aromatic chain.
  • R a or R b of the compound of formula (I) is a hydrocarbon chain constituted only by carbon atoms and hydrogen atoms.
  • R a or R b of the compound of formula (I) is aromatic.
  • R a or R b may be selected from phenyl or furyl groups.
  • R a or R b of the compound of formula (I) is a linear, branched or cyclic aliphatic (non- aromatic) hydrocarbon chain.
  • R a or R b is selected from a linear or branched, saturated or unsaturated, hydrocarbon chain having from 2 to 40 carbon atoms, preferably from 4 to 32 carbon atoms, more preferably from 5 to 24 carbon atoms, even more preferably from 6 to 18 carbon atoms.
  • R a or R b is selected from a linear, unbranched, saturated or unsaturated, hydrocarbon aliphatic chain having from 2 to 40 carbon atoms, preferably from 4 to 32 carbon atoms, more preferably from 5 to 24 carbon atoms, even more preferably from 6 to 18 carbon atoms.
  • R a or R b is selected from a linear unbranched saturated hydrocarbon aliphatic chain having from 2 to 40 carbon atoms, preferably from 4 to 32 carbon atoms, more preferably from 5 to 24 carbon atoms, even more preferably from 6 to 18 carbon atoms.
  • R a or R b is selected from pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl, palmityl, stearyl, 12-hydroxy stearyl, oleyl, 12-hydroxyloleyl, linoleyl, linolenyl, arachidyl, behenyl or erucyl groups.
  • R c is not cyclic.
  • R c is selected from hydrocarbon aliphatic chains comprising a hydrocarbon main chain having from 1 to 14 carbon atoms and a side chain having from 1 to 6 carbon atoms.
  • R c is selected from hydrocarbon aliphatic chains comprising a hydrocarbon main chain having from 2 to 8 carbon atoms and a side chain having from 1 to 4 carbon atoms.
  • R is selected
  • the compounds of formula (I) according to the invention do not present urea functions of type -NH-CO-NH-.
  • the viscosifier is a N-hydrocarbyldiamide composition
  • a N-hydrocarbyldiamide composition comprising
  • the molar ratio of the compound of formula (la) to compound (lb) is preferably in the range of from 70:30 to 99: 1 , preferably in the range of from 75:25 to 98:2, more preferably of from 85: 15 to 97:3 and most preferably of from 90:10 to 97:3.
  • aggregated weight proportion of compounds (la) and (lb) is preferably at least 50 wt%, further preferably at least 80 wt%, more preferably at least 90 wt% of the total weight of the composition.
  • the N- hydrocarbyldiamide composition essentially consists of compounds (ia) and (lb) or consists of compounds (la) and (lb).
  • N- hydrocarbyldiamide compositions in which R is identical to R 4 , R 2 is identical to R 5 and R 3 is identical to R 6 , i.e. the N-hydrocarbyldiamide composition is preferably an isomer mixture.
  • R 1 or R 4 of the compound of formula (la) respectively formula (lb) is a hydrocarbon chain constituted only of carbon atoms and hydrogen atoms.
  • R 1 or R 4 of the invention are identical to each other embodiment of the invention.
  • compound of formula (la) respectively formula (lb) is a linear, branched or cyclic aliphatic (non-aromatic) hydrocarbon chain.
  • R or R 4 is selected from a linear or branched, saturated or unsaturated, hydrocarbon chain having from 2 to 40 carbon atoms, preferably from 4 to 32 carbon atoms, more preferably from 5 to 24 carbon atoms, even more preferably from 6 to 18 carbon atoms.
  • R 1 and/or R 4 can preferably be selected from
  • R 2 and/or R 5 are preferably selected from hydrocarbon aliphatic chains comprising a hydrocarbon main chain having from 1 to 14 carbon atoms.
  • R 2 and/or R 5 preferably comprise from 1 to 12 carbon atoms, more preferably 1 to 4 carbon atoms and still more preferably 1 to 2 carbon atoms
  • R 2 and/or R 5 are preferably selected from (i) linear alkylene
  • linear alkylene chains and (ii) from linear alkylene chains substitued by one and only one linear alkyl group, wherein the linear alkyl group substituent comprises a number of carbon atoms that is preferably lower, more preferably does not comprise more than half of the carbon atoms of the linear alkylene chains and more preferably does not exceed two and more preferably does not exceed one carbon atom. More preferably, R 2 and/or R 5 are linear alkylene chains.
  • R 2 and/or R 5 are methylene.
  • R 2 and/or R 5 include
  • R 2 and R 5 may also be; -CH(CH 2 -CH 3 )-CH 2 -.
  • R 3 and R 6 are linear or branched alkyl groups with 1 to 8, preferably 1 to 4 carbon atoms, most preferably R 3 and R 6 are methyl.
  • the compounds of formula (la) and (lb) forming the N- hydrocarbyldiamide mixture according to the invention do not present urea functions of type -NH-CO-NH-.
  • the compounds of formula (I) or the mixtures consisting of the compounds of formula (la) and (lb) may be obtained by a process wherein at least one amine and at least one reactant selected from an imide, a diacid, a diester, a primary diamide, an ester amide, an acid ester or other combinations are reacted.
  • a preferred process for manufacturing the N-hydrocarbyldiamide mixtures of compounds (la) and (lb) comprises the steps of
  • step b) subjecting the reaction product obtained in step a) to at least two cycles of recrystallization and washing steps. With increasing number of recrystallization cycles, the ratio of compounds of formula (la) and (lb) increases, if (la) and (lb) are isomers of the same N-hydrocarbyldiamide.
  • Ammonia may also be added during the process if it is not already present in the molecule as amide or imide functions. Ammonia may allow favoring the manufacture of the mono-alkyl form (versus the dialkyl form) of the diamide and may also allow favoring the elimination of by-products formed during the reaction (such as alcohol coming from reaction with ester as a co-product).
  • the process for manuifacture of the viscosifier comprises the direct reaction between a cyclic imide and an amine.
  • the imide may be preferably selected from 2-methyl-glutarimide, 3-methyl- glutarimide, 2-ethyl-glutarimide, 3-ethyl-glutarimide, 2-methyl-succinimide and 2-ethyl-succinimide.
  • the imide can be a cyclic imide of formula (III-1 ):
  • the amine is preferably a primary amine of general formula R 1 '-NH2, with R defined as above.
  • the reaction for preparing the viscosifier may be performed for example, at a temperature ranging from 20°C to 200°C, preferably from 50°C to 180°C, more preferably from 100°C to 160°C.
  • the reaction may be performed with a progressive heating in order to avoid loss of amines through evaporation or may be performed under pressure to keep the amine in the liquid phase.
  • the temperature of the mixture is approximately equal to the boiling point of the amine.
  • the reaction for preparing the viscosifier is preferably performed under atmospheric pressure.
  • the viscosifier used as component c) in the formulations according to the invention may be partially or fully solubilized in the organic liquid (solvent). It is preferably fully solubilized in the organic liquid (solvent).
  • the viscosifier used as component c) in the formulations according to the invention may be available in the form of a mixture M comprising the N- hydrocarbyldiamide (I), in particular (la) and (lb), and at least one solvent, said compound of formula (I) respectively the mixture of (la) and (lb) being partially or fully solubilized in said solvent.
  • the N-hydrocarbyldiamide compounds (I) or (la) and (lb) are preferably fully solubilized in the at least one solvent.
  • the mixture M is preferably a solution comprising at least one solvent and, fully dissolved therein, at least one compound of formula (I) or the compounds of formula (la) and (lb), that is to say the mixture M is free of any compound that would be insolubilized in the solvent.
  • the mixture M is one which, when at room temperature and at atmospheric pressure (20 °C, 1 atm), comprises the N- hydrocarbyldiamides (I) or (la) and (lb) in partially or fully solubilized form in the solvent. More preferably, the mixture M is one which, when at room temperature and at atmospheric pressure, comprises the N- hydrocarbyldiamides of formula (I) or the mixture of (la) and (lb) in fully solubilized form.
  • the mixture M is one which, when at 60°C and at
  • the mixture M is one which, when at 40°C and at atmospheric pressure, comprises the N- hydrocarbyldiamides (I) or (la) and (lb) in fully solubilized form.
  • the mixture M is a solution when it is put at 60°C and at atmospheric pressure.
  • the mixture M is a solution when it is put at 40°C and at atmospheric pressure. More preferably, the mixture M is a solution when it is put at room temperature (20°C) and at atmospheric pressure.
  • the solvent used in the mixture M is a good solvent and can be a polar solvent or a mixture of a polar solvent and an apolar solvent.
  • polar solvents it is to be understood solvents having a polar and hydrogen bonding components respectively ⁇ ⁇ and 5h (Hansen solubility parameter) strictly greater than 0. Hansen solubility parameters are well known for the skilled person: ⁇ ⁇ corresponds to the energy from dipolar intermolecular forces between molecules and 5h corresponds to the energy from hydrogen bonds between molecules.
  • the solvent of the mixture M is selected from alcohols having from 1 to 10 carbon atoms, preferably selected from methanol, ethanol, isopropanol, butanol, isobutanol, diethylene glycol, butylene glycol, methyl propane diol.
  • the solvent of the mixture M is selected from acetal derivatives having from 2 to 12 carbon atoms, and is preferably selected from the Augeo® family of solvents (available from Solvay SA) such as Augeo® SL191 which is a racemic mixture (+/-)-2,2- dimethyl-4-hydroxymethyl-1 ,3-dioxolane also known as isopropylidene glycerol.
  • the solvent of the mixture M is itself a mixture of (i) alcohols having from 1 to 10 carbon atoms
  • alkyl esters having from 2 to 12 carbon atoms preferably selected from ethyl acetate, propyl acetate, butyl acetate, hexyl acetate, ethylhexyl acetate or octyl acetate
  • acetal derivatives having from 2 to 12 carbon atoms preferably selected from the Solvay available Augeo family of solvents (available from Solvay SA) such as Augeo® SL191 which is a racemic mixture (+/-)-2,2-dimethyl-4-hydroxymethyl-1 ,3-dioxolane also known as isopropylidene glycerol).
  • the solvent of the mixture M is selected from lactate esters, in particular selected from methyl lactate, ethyl lactate, n-propyl lactate, n-butyl lactate, 2-ethylhexyl lactate, especially from methyl L-lactate, ethyl L-lactate, n-propyl L-lactate, n-butyl L-lactate, 2-ethylhexyl L-lactate.
  • the mixture M may be from a liquid state to a flowable thick paste at
  • temperatures ranging from 20°C to 50°C.
  • the N-hydrocarbyldiamide compound I respectively the mixture of N-hydrocarbyldiamines of formula (la) and (lb) in accordance with a preferred embodiment represents from 1 % to 75% by weight, preferably from 10% to 50% by weight, more preferably from 15% to 30% by weight, of the total weight of the mixture M.
  • the mixture M comprises
  • the mixture M may be obtained by simple mixing of the ingredients (N- hydrocarbyldiamide compounds and solvent), preferably at a temperature comprised between 10°C and 60°C, ideally about 25°C (room
  • the formulations according to the invention in a preferred embodiment, comprise as component d) at least one biologically active ingredient, preferably a pharmaceutically active ingredient or an agriculturally active ingredient.
  • the amount thereof is usually at least 0,5 wt%, preferably of form 1 -20 wt%, even more preferably of from 2 to 15 wt% of the weight of the formulation.
  • biologically active ingredient when used herein, is intended to denote an entity which interacts with biological material in a manner that dieseases in animals, such as mammals, may be prevented or combatted or which influences growth of agricultural crops or which combats weeds, insects, bacteria or fungi in agricultural crops.
  • the formulation comprises an agriculturally active ingredient selected from the group consisiting of agriculturally active ingredient is selected from herbicides, insecticides, fungicides, parasiticides, plant growth regulators, fertilizers, bactericides and insect repellents.
  • the biologically active compounds are preferably biologically active compounds used to control agricultural pests and include, for example, herbicides, plant growth regulators, crop dessicants, fungicides, bacteriocides, bacteriostats, insecticides, and insect repellants.
  • the formulation according to the invention may further contain any additive usually contemplated in phytosanitary formulations like for example safeners.
  • any additive usually contemplated in phytosanitary formulations like for example safeners.
  • the formulations according to the invention allow to achieve stabilized oil dispersions or emulsions with a great diversity of salts and/or active materials, in particular active compounds used to control agricultural pests.
  • these concentrate formulations may also be convenient for vehiculing other active materials like fertilizers.
  • These active materials and/or salts may be of very different chemical nature, like for example organic, inorganic, liposoluble or not.
  • the farm operators may prepare pulverizable liquid compositions and in particular aqueous emulsions or suspoemulsions by diluting a concentrate according to the invention. Generally, they just proceed to a dilution with water and oil if necessary, and optionally also supplement the so-obtained pulverizable formulation with at least one ingredient chosen from salts, hydrocolloids and their mixtures.
  • a concentrate formulation according to the invention it is also possible for a concentrate formulation according to the invention to already contain such a material.
  • the salts may be chosen among sodium carbonate,
  • hydrocolloid particularly convenient for the invention may be cited the guar.
  • a formulation according to the invention may be used by the farm operators for preparing different pulverizable compositions which may be kept for a long time without any undesirable phenomenon of demixtion.
  • the non-aqueous formulations supplemented with at least one ingredient chosen from salts like sodium carbonate, sodium bicarbonate, ammonium sulfate or their mixtures; hydrocolloids such as guar; and their mixtures as well as the corresponding emulsions obtained by a dilution of the concentrates into water, are also known under the name of tankmix.
  • a tankmix may be obtained by adding to a formulation according to the invention prepared as above mentioned, at least an ingredient chosen from salts, hydrocolloids and their mixtures to a homogenizer. The so obtained composition is then blended and diluted or not with water to form an emulsion.
  • invention contains less than 2 % by weight of water and preferably is anhydrous.
  • Tankmix formulations according to the invention are pourable, show a good storage stability, are emulsifiable and provide stable emulsions when diluted into water.
  • the formulation according to the invention is also particularly interesting for industrial firms which, by using only one concentrate, may prepare a great diversity of pesticidal oil dispersions.
  • a pesticidal oil dispersion according to the invention may contain until 50 % in particular from 1 to 20 %, more preferably 3 to 10 % by weight of solid pesticidal active material(s) with respect to its total weight.
  • the particle size of such active materials preferably is lower than 50 ⁇ in particular lower than 20 ⁇ and more particularly lower than 10 ⁇ . This size may be measured by laser diffraction (CIPAC MT 187) or rough estimation of average diameter by optical microscopy.
  • formulations according to the invention keep their storage stability when containing the active materials active materials.
  • Pesticidal oil dispersions obtained with the formulations according to the invention are still pourable. In particular, they preferably have a viscosity ranging from 500 to 3000 mPas.
  • compositions containing active ingredients where the active ingredients or e.g. adjuvants have to be suspended as particulate matter.
  • Particulate matter for the purpose of the present invention is intended to denote any particles with different densities equal or different from the continuous medium. If the density is different from the density of the continuous medium, the latter should have a non zero yield stress value, preferably a yield stress value above 0.5 Pa and preferably above 0.75 Pa.
  • a formulation according to the invention may be obtained by adding, in the order listed, a non-esterified vegetable oil as organic liquid, a viscosifier as defined in the claims, a surfactant S as defined in the claims and, optionally, an active ingredient according to the invention to a
  • the samples were melted at 120°C under shear set at 100s-1 immediately followed by a oscillatory collection of elastic modulus G' versus time (frequency of 1 Hz at a 0.1 % strain) as the temperature was quenched from 120°C to 25°C then remaining at 25°C using the Peltier temperature controlled stage.
  • a gel was prepared with 0.75 wt% of C6 Gelator (65/35) from example 1 in Rapeseed oil RADIA 6105 from Oleon and 30 wt% of the nonionic surfactant Alkamuls VO2003 from Solvay.
  • the obtained gel was transparent and resisted to an upside-down flip of the vial.
  • Upon injection in water with a 50 times or more dilution ratio good immediate "blooming" self-emu Isification was observed.
  • a gel was prepared with 0.75 wt% of C6 Gelator (65/35) from example 1 in methylated rapeseed oil RADIA 7956 from Oleon and 30 wt% of the nonionic surfactant Alkamuls T85V from Solvay. The obtained gel was transparent and resisted to an upside-down flip of the vial. Upon injection in water with a 50 times or more dilution ratio good immediate "blooming" self-emulsification was observed. [00208] (Example 5
  • a formulation 1 was prepared with Rapeseed oil RADIA 6105 from Oleon, 0.75 wt% of the C6 gelator (65/35) from example 1 and 30wt% of the nonionic surfactant Alkamuls VO 2003 from Solvay. Then 4 wt% of Nicosulfuron was added to the formulation.
  • the obtained pesticidal formulation was stable against sedimentation and presented no or very little syneresis upon storage at 45°C.
  • the sample displayed good shear thinning behavior when subjected to a steady shear in a rheometer compatible with an easy pour from a container when shaken.
  • a formulation 2 was prepared with methylated Rapeseed oil RADIA 7956 from Oleon, 0.75wt% of the C6 gelator (65/35) from example 1 and 30wt% of the nonionic surfactant Alkamuls T85V from Solvay. 4 wt% of
  • Nicosulfuron was added to the formulation.
  • the obtained pesticidal formulation was stable against sedimentation and presented no or very little syneresis upon storage at 45°C.
  • the sample displayed good shear thinning behavior when subjected to a steady shear in a rheometer compatible with an easy pour from a container when shaken.
  • a mixture M was prepared by weighing the C6 gelator (65/35) from
  • example 1 in n-Propyl L-lactate (Purasolv NPL from Corbion) to obtain a 25wt% solution and placing it in an oven at 60°C for complete dissolution.
  • Viscosity measurements were made using a Gilson Viscoman.
  • Stability measurements were conducted by placing the formulations in a 40°C oven and capturing the image of each formulation after the storage time at 40°C indicated in each example.
  • a composition A1 was prepared in Rapeseed oil RADIA 6105 from Oleon and adding Mesotrione powder, the nonionic surfactant Alkamuls VO2003 from Solvay wet grinding it with Ultraturrax (IKA T10 Basic S10N-5G medium speed) for 1.5 minutes.
  • the mixture M from example 7 previously heated to 60°C is then introduced to the composition A1 to form the formulation B1.
  • the formulation B1 is as follows: Mesotrione (1 OOg/l), Alkamuls VO 2003 7wt%, C6 Gelator 0.65wt%, n-Propyl L-lactate 1.95w% the rest being rapeseed oil. After a hand mixing at room temperature, the formulation B1 is left at rest until gel formation. The flowable formulation is obtained using vortex mixing with glass beads.
  • a composition A2 was prepared in methylated Rapeseed oil RADIA 7956 from Oleon and adding Mesotrione powder, the nonionic Alkamuls T85V from Solvay wet grinding it with Ultraturrax (IKA T10 Basic S10N-5G medium speed) for 1.5 minutes.
  • the mixture M from example 7 previously heated to 60°C is then introduced to the composition A2 to form the formulation B2.
  • the formulation B2 is as follows: Mesotrione (1 OOg/l), Alkamuls T85V 7wt%, C6 Gelator 1.2wt%, n-Propyl L-lactate 3.6w% the rest being methylated rapeseed oil. After a hand mixing at room
  • the formulation B2 is left at rest until gel formation.
  • the flowable formulation is obtained using vortex mixing with glass beads.
  • a composition A3 was prepared in Soy Bean Oil Amesolv SOR Soybean oil from Ametech and adding Mesotrione powder, the nonionic surfactant Alkamuls VO2003 from Solvay wet grinding it with Ultraturrax (IKA T10 Basic S10N-5G medium speed) for 1.5 minutes.
  • the mixture M from example 7 previously heated to 60°C is then introduced to the composition A3 to form the formulation B3.
  • the formulation B3 is as follows:
  • a composition A4 was prepared in Methyl Soyate Amesolv MTES from
  • the nonionic surfactant Alkamuls T85V from Solvay wet grinding it with Ultraturrax (IKA T10 Basic S10N-5G medium speed) for 1.5 minutes.
  • the mixture M from example 7 previously heated to 60°C is then introduced to the composition A4 to form the formulation B4.
  • the formulation B4 is as follows: Mesotrione (1 OOg/l), Alkamuls T85V 7wt%, C6 Gelator 1.2wt%, n-Propyl L-lactate 3.6w% the rest being Methyl Soyate. After a hand mixing at room temperature, the formulation B4 is left at rest until gel formation. The flowable formulation is obtained using vortex mixing with glass beads.
  • composition A5 was prepared in Rapeseed oil RADIA 6105 from Oleon and adding Nicosulfuron powder, the nonionic surfactant Alkamuls
  • VO2003 from Solvay wet grinding it with Ultraturrax (IKA T10 Basic S10N- 5G medium speed) for 1.5 minutes.
  • the mixture M from example 7 previously heated to 60°C is then introduced to the composition A5 to form the formulation B5.
  • the formulation B5 is as follows: Nicosulfuron (100g/l), Alkamuls VO 2003 7wt%, C6 Gelator 0.65wt%, n-Propyl L-lactate 1.95w% the rest being rapeseed oil. After a hand mixing at room temperature, the formulation B5 is left at rest until gel formation. The flowable formulation is obtained using vortex mixing with glass beads.
  • Pesticidal compositions in methylated rapeseed oil are known in the art.
  • a composition A6 was prepared in methylated Rapeseed oil RADIA 7956 from Oleon and adding Nicosulfuron powder, the nonionic Alkamuls T85V from Solvay wet grinding it with Ultraturrax (IKA T10 Basic S10N-5G medium speed) for 1.5 minutes.
  • the mixture M from example 7 previously heated to 60°C is then introduced to the composition A6 to form the formulation B6.
  • the formulation B6 is as follows: Nicosulfuron (1 OOg/l), Alkamuls T85V 7wt%, C6 Gelator 1.5wt%, n-Propyl L-lactate 4.5w% the rest being methylated rapeseed oil. After a hand mixing at room

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Abstract

L'invention concerne une formulation émulsionnable non aqueuse comprenant a) au moins 3 % en poids d'au moins un tensioactif, b) au moins 10 % en poids d'un liquide organique, c) au moins 0,1 % en poids d'au moins un améliorant de viscosité choisi parmi les N-hydrocarbyldiamides ou leurs mélanges.
PCT/EP2018/077227 2017-10-05 2018-10-05 Formulations comprenant des tensioactifs, des liquides organiques et des améliorants de viscosité WO2019068914A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05320617A (ja) * 1992-05-21 1993-12-03 New Japan Chem Co Ltd 新しい有機性ゲル化剤
JP2956817B2 (ja) * 1993-11-15 1999-10-04 日清製油株式会社 有機媒体の固化剤またはゲル化剤
WO2010031867A1 (fr) 2008-09-22 2010-03-25 Rhodia Operations Produit comprenant des diamides, procede de preparation et utilisations
EP2364591A1 (fr) * 2010-03-09 2011-09-14 Cognis IP Management GmbH Compositions biocides comprenant des alkylamides d'acides dicarboxyliques
WO2013043678A1 (fr) 2011-09-19 2013-03-28 Rhodia Operations Compositions d'adjuvant, compositions de pesticide agricole, et procédés pour fabriquer et utiliser de telles compositions
WO2016142518A1 (fr) 2015-03-12 2016-09-15 Rhodia Operations Formulations de concentré, dispersions d'huile agrochimiques, procédés et utilisations de celles-ci

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05320617A (ja) * 1992-05-21 1993-12-03 New Japan Chem Co Ltd 新しい有機性ゲル化剤
JP2956817B2 (ja) * 1993-11-15 1999-10-04 日清製油株式会社 有機媒体の固化剤またはゲル化剤
WO2010031867A1 (fr) 2008-09-22 2010-03-25 Rhodia Operations Produit comprenant des diamides, procede de preparation et utilisations
EP2364591A1 (fr) * 2010-03-09 2011-09-14 Cognis IP Management GmbH Compositions biocides comprenant des alkylamides d'acides dicarboxyliques
WO2013043678A1 (fr) 2011-09-19 2013-03-28 Rhodia Operations Compositions d'adjuvant, compositions de pesticide agricole, et procédés pour fabriquer et utiliser de telles compositions
WO2016142518A1 (fr) 2015-03-12 2016-09-15 Rhodia Operations Formulations de concentré, dispersions d'huile agrochimiques, procédés et utilisations de celles-ci

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
NIEK ZWEEP ET AL: "Balancing Hydrogen Bonding and van der Waals Interactions in Cyclohexane-Based Bisamide and Bisurea Organogelators +", LANGMUIR, vol. 25, no. 15, 4 August 2009 (2009-08-04), US, pages 8802 - 8809, XP055428950, ISSN: 0743-7463, DOI: 10.1021/la9004714 *
SHANE M. HICKEY ET AL: "Organogelators based on the norbornane scaffold", SUPRAMOLECULAR CHEMISTRY., vol. 27, no. 5-6, 13 December 2014 (2014-12-13), US, pages 425 - 435, XP055383352, ISSN: 1061-0278, DOI: 10.1080/10610278.2014.990391 *

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