WO2009133181A1 - Composes de type ether-amide, procede de preparation et utilisations - Google Patents
Composes de type ether-amide, procede de preparation et utilisations Download PDFInfo
- Publication number
- WO2009133181A1 WO2009133181A1 PCT/EP2009/055287 EP2009055287W WO2009133181A1 WO 2009133181 A1 WO2009133181 A1 WO 2009133181A1 EP 2009055287 W EP2009055287 W EP 2009055287W WO 2009133181 A1 WO2009133181 A1 WO 2009133181A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- formula
- groups
- formulation
- compound
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/22—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from nitriles
Definitions
- the subject of the present invention is new compounds of the ether amide type.
- solvents are used for the formulation of phytosanitary assets, especially in the form of emulsifiable concentrates (Emulsifiable Concentrate "EC") intended to be diluted in water by the farmer, before application to a field.
- EC emulsifiable Concentrate
- the industry is looking for new compounds to vary or optimize products and processes in which solvents, including polar solvents, are to be used.
- solvents including polar solvents
- the industry needs low cost compounds with interesting properties of use.
- the industry also needs compounds with a toxicological and / or ecological profile perceived as favorable, in particular low volatility (low VOC), good biodegradability, low toxicity and / or low hazard.
- dialkylamides The use as solvents of dialkylamides is known. It is a product of formula R-CONMe 2 or R is a hydrocarbon group such as an alkyl, typically C 6 -C 30 . Such products are marketed under the name
- Genagen® by the company Clariant. These solvents find applications particularly in the phytosanitary field. These solvents, however, have a limited range of use and do not allow solubilizing certain phytosanitary actives at certain concentrations, in useful temperature ranges, without crystal formation.
- the present invention satisfies at least one of the requirements expressed above by proposing a compound of formula (I) below: R a R b C (OR 1 ) -CHR c -CONR 2 R 3 (I) where
- R a , R b and R c are groups chosen from hydrogen atom and linear or branched alkyl groups, preferably dC 3 , - R 1 is a group R ' 1 or - (AO) n R ' 1 , where
- R ' 1 is a group selected from hydrocarbon groups comprising an average number of carbon atoms ranging from 1 to 36, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, said aromatic groups may comprise a heteroatom in a aromatic cycle,
- AO identical or different, represents a group of formula -CH 2 -CH 2 -O-, -CHMe-CH 2 -O-, or -CH 2 -CHMe-O-
- n is an average number greater than or equal to 0, ranging for example from 0 to 50,
- R 2 and R 3 which are identical or different, are groups chosen from a hydrogen atom and hydrocarbon groups comprising an average number of carbon atoms ranging from 1 to 36, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted, R 2 and R 3 may optionally together form a ring, optionally substituted and / or optionally comprising a heteroatom, - R 2 and R 3 are not simultaneously hydrogen atoms.
- the invention also relates to a process for preparing the compound.
- the invention also relates to the use of the compound as surfactant, solvent, co-solvent, etchant, crystallization inhibitor, cleaning agent, degreasing agent, plasticizer or coalescing agent.
- the subject of the invention is also a method of solvation, co-solvation, plasticization, coalescence and / or crystallization inhibition by addition of the compound of the invention.
- the invention also relates to formulations comprising the compound of the invention.
- the formulations may in particular be phytosanitary formulations.
- composition of matter means a composition, more or less complex, comprising several chemical compounds. It can typically be an unpurified or modestly purified reaction product.
- the compound of the invention may in particular be isolated and / or marketed and / or used in the form of a material composition comprising it.
- the compound of the invention in the form of a pure molecule or in the form of a mixture corresponding to formula (I), may be included in a composition of matter.
- solvent is understood in a broad sense, covering in particular the co-solvent functions, crystallization inhibitor, stripper.
- solvent may especially denote a liquid product at the temperature of use, preferably having a melting point of less than or equal to 20 ° C., preferably at 5 ° C., preferably at 0 ° C., which can contribute to making a liquid solid material, or to prevent or retard the solidification or crystallization of material in a liquid medium.
- the compound of the invention has the general formula (I) given above. It is noted that it may be a mixture of several compounds of general formula (I). In other words the compound can be alone or in mixture. In the case of mixtures of several compounds, the number of atoms or of units can be expressed in average numbers. These are average numbers in number. In the case of single compounds, it will generally be integers, as regards the number of carbon atoms.
- the groups R a , R b and R c which are identical or different, are groups chosen from hydrogen and linear or branched alkyl groups.
- the alkyls may in particular be C 1 -C 6 alkyls, preferably C 1 -C 3 alkyls. It may especially be methyl or ethyl groups. According to one particular embodiment, the total number of carbon atoms, excluding groups R 1 , R 2 and R 3, is 4, 5, or 6.
- At least one of the groups selected from R a , R b and R c is different from the hydrogen atom, for example a group selected from linear or branched alkyl groups.
- the alkyls may in particular be C 1 -C 6 alkyls, preferably C 1 -C 3 alkyls. It may especially be methyl or ethyl groups.
- the total number of carbon atoms, excluding groups R 1 , R 2 and R 3, is 4, 5, or 6.
- R c is a methyl group
- R a and R b which are identical or different, can be groups chosen from hydrogen atom and linear or branched alkyl groups.
- the alkyls may in particular be C 1 -C 6 alkyls, preferably C 1 -C 3 alkyls. It may especially be methyl or ethyl groups.
- the total number of carbon atoms, excluding groups R 1 , R 2 and R 3, is 4, 5, or 6.
- R c is a hydrogen atom
- R a is a group chosen from the hydrogen atom and the linear or branched alkyl groups
- R b is a group chosen from linear alkyl groups or branched.
- the alkyls may in particular be C 1 -C 6 alkyls, preferably C 1 -C 3 alkyls. It may especially be methyl or ethyl groups.
- the total number of carbon atoms, excluding groups R 1 , R 2 and R 3, is 4, 5, or 6.
- R a may be a group selected from linear or branched alkyl groups.
- the alkyls may in particular be alkyls having a d-C ⁇ , preferably a C 1 -C 3 alkyl. It may especially be methyl or ethyl groups. According to one particular embodiment, the total number of carbon atoms, excluding groups R 1 , R 2 and R 3, is 4, 5, or 6.
- R b and R c which may be identical or different, may be groups chosen from hydrogen atom and linear or branched alkyl groups.
- the alkyls can in particular be alkyls having dC 6 , preferably dC 3 . It may especially be methyl or ethyl groups. According to one particular embodiment, the total number of carbon atoms, excluding groups R 1 , R 2 and R 3, is 4, 5, or 6.
- R a is a group chosen from linear or branched alkyl groups.
- the alkyls can in particular be alkyls having dC 6 , preferably dC 3 . It may especially be methyl or ethyl groups.
- the total number of carbon atoms, out of groups R 1 , R 2 and R 3, is 4, 5, or 6.
- - R b and R c which are identical or different, are groups chosen from the hydrogen atom and the linear or branched alkyl groups.
- the alkyls can in particular be alkyls having dC 6 , preferably dC 3 . It may especially be methyl or ethyl groups.
- the total number of carbon atoms, excluding groups R 1 , R 2 and R 3, is 4, 5, or 6.
- R a is a methyl group or ethyl.
- This particular embodiment can for example be implemented by transformation from an alkene-nitrile of formula ( I 1 ) of 2-pentenenitrile type (sometimes denoted 2PN). It can be in particular cis-2-pentenenitrile or trans-2-pentenenitrile.
- This particular embodiment can for example be implemented by conversion from an alkene nitrile of formula (I 1 ) of the methyl-2-butenenitrile type (sometimes denoted by 2BN).
- It may be in particular a 2-methyl-2-butenenitrile such as cis-2-methyl-2-butenenitrile or trans-2-methyl-2-butenenitrile, or a 3-methyl-2-butenenitrile such as cis-3-methyl-2-butenenitrile or trans-3-methyl-2-butenenitrile.
- the molar ratio between the first and the second may for example be between 50/50 and 99/1, preferably between 60/40 and 90/10.
- the groups R 2 and R 3 which are identical or different, are groups chosen from a hydrogen atom and hydrocarbon groups comprising an average number of carbon atoms ranging from 1 to 36, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted, R 2 and R 3 may optionally together form a ring comprising the nitrogen atom to which they are bonded, optionally substituted and / or optionally comprising an additional heteroatom. It should be noted that R 2 and R 3 are not simultaneously hydrogen atoms. In other words, the group -CONR 2 R 3 is not a group - CONH 2 .
- R 2 and R 3 may be a -CONHR 2 group in which R 2 is not a hydrogen atom, or a -CONR 2 R 3 group in which R 2 and R 3 are not hydrogen atoms.
- R 2 and R 3 which may be identical or different, may for example be chosen from methyl, ethyl, propyl (n-propyl), isopropyl, n-butyl, isobutyl, n-pentyl, amyl, isoamyl, hexyl and cyclohexyl groups; mixtures and / or combinations.
- R 2 and R 3 may also be such that together they form with the nitrogen atom a morpholine, piperazine or piperidine group.
- R 2 and R 3 can in particular be methyl groups, preferably both.
- the group R 1 is a group typically corresponding to an alcohol R 1 -OH. In one case it may correspond to a simple alcohol R ' 1 -OH. In another case it may correspond to an ethoxylated and / or propoxylated alcohol of formula HO- (AO) n R ' 1 .
- R ' 1 represents the hydrocarbon residue of its optionally ethoxylated and / or propoxylated alcohols.
- the group R ' 1 is a group chosen from hydrocarbon groups comprising an average number of carbon atoms ranging from 1 to 36, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, said aromatic groups possibly comprising a heteroatom in a cycle aromatic.
- the heteroatom of the aromatic group may be an oxygen or nitrogen atom. It is mentioned that the aromatic group can be directly attached or carried by an alkyl group. It is mentioned that cyclic or aromatic groups may be substituted.
- R ' 1 may for example be chosen from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, isoamyl, n-hexyl, cyclohexyl, n-octyl, isooctyl, 2-ethylhexyl, tridecyl groups; , phenyl, benzyl and mixtures thereof.
- R 1 may be a more or less complex mixture, which may correspond to the use of a more or less complex mixture of R 1 -OH alcohols, for example fusel oil.
- R 1 is a group other than n-hexyl and
- R a and / or R b is different from the hydrogen atom.
- R 1 is a group other than n-butyl and R a and / or R b is different from the hydrogen atom.
- R 1 is a group other than ethylhexyl and R a and / or R b is different from the hydrogen atom.
- R 1 is a group other than n-hexyl.
- R 1 is a group other than n-butyl. According to a particular embodiment, R 1 is a group other than ethylhexyl.
- the group R 1 is a cyclic group, preferably a cyclohexyl group.
- the compounds having such a group have following properties and / or properties of miscibility in water of particular interest, especially in the context of phytosanitary formulations.
- the group (AO) represents an ethoxy group of formula -CH 2 -CH 2 -O- or a propoxy group of formula -CHMe-CH 2 -O-, or -CH 2 -CHMe-O-.
- the number n is an average number greater than or equal to 0, ranging for example from 0 to 50. It typically represents a degree of ethoxylation and / or propoxylation. In the case where ethoxy and propoxy groups are present, they can be distributed randomly or sequentially.
- the compound of the invention is preferably such that it has a melting point of less than or equal to 20 ° C., preferably at 5 ° C., preferably at 0 ° C.
- the groups detailed above are preferably such that the compound has this property.
- the compound of the invention can be completely miscible in water.
- the compound of the invention is partially miscible in water.
- the miscibility in water may for example be less than 10% by weight (at 25 ° C), preferably 2%, preferably 1% or 0.1%. It may be greater than 0.001%, preferably 0.01% or 0.1%. It may for example be between 0.01% and 2%, for example between 0.1% and 1%.
- the compounds of the invention have the following good properties, in particular for phytosanitary active agents in phytosanitary formulations with low miscibility in water.
- the groups R a , R b , R c , and / or the group R 1 and / or the groups R 2 and R 3 may be chosen so as to control the miscibility in water.
- the compound of the invention preferably has one of the following formulas:
- the compound may be a mixture of compounds having these formulas. It may be for example the following mixtures:
- the compound of the invention may be included in a composition of matter, comprising products other than the compound alone or in a mixture of formula (I).
- the compound of the invention may represent at least 10% by weight.
- it is the main compound of the composition of matter.
- main compound is meant in the present application, the compound whose content is the highest, even if its content is less than 50% by weight (for example in a mixture of 40% of A, 30% of B and 30% of C, product A is the main compound).
- the compound of the invention is at least 50% by weight of the composition of matter, for example 70 to 95% by weight, and even 75 to 90% by weight.
- the composition of matter may be a reaction product.
- the other products of the composition of matter may in particular be by-products of impurities, unreacted products, or products corresponding to reaction adducts of products included in the starting compounds not leading to compounds of formula (I).
- the compound of the invention may in particular be prepared by transformation from an alkene-nitrile of formula (I 1 )
- R a R b C CR c -CN (I 1 ). It is noted that in all the processes and sequences mentioned below, it is possible to implement optional intermediate separation and / or purification steps, for example to eliminate non-target by-products. By-products may be optionally used to make other products, or may be processed for reintroduction into the process. The process may be followed by filtration and / or purification steps, for example by distillation.
- the addition of the alcohol can be carried out in a known manner, for example in the presence of a base, often in a catalytic amount. This is a type addition
- Michael It can be carried out in a solvent, preferably in a non-aqueous solvent.
- a solvent the alcohol of formula R 1 -
- the conversion of the -CN group can in particular comprise a conversion of the -CN group to -COOH or -COOR 'group where R' is a C 1 -C 4 alkyl, then a conversion of the -COOH or -COOR 'group to the -CONR 2 R group 3 using an amine of formula HNR 2 R 3 .
- the method comprises the following steps: Step 1) is reacted alkene-nitrile of formula (I 1) with an alcohol of formula R 1 -OH to obtain an ether-nitrile of formula (II 1)
- Step 1) typically constitutes a Michael reaction.
- a base preferably in a non-aqueous solvent, for example the alcohol of formula R 1 -OH, typically in a large excess.
- a base it is possible, for example, to use an ammonium hydroxide, an alkali metal, etc.
- Step 2) typically constitutes a conversion of the group -CN into a group - CONR 2 R 3 .
- Step 2) advantageously comprises the following steps: Step 2a): the group -CN is converted into a group -COOH or -COOR 'where R' is a C 1 -C 4 alkyl, step 2b): the -COOH group is converted or -COOR 'in group -CONR 2 R 3 with an amine of formula HNR 2 R 3 , so as to obtain the compound of formula (I).
- step 2) comprises the following steps: 2a ') the -CN group is converted into a -COOH group directly by hydrolysis or by forming a -COOR' group and then hydrolyzing,
- the -COOH group is converted to the -CONR 2 R 3 group directly by reaction with an amine of formula HNR 2 R 3 or by forming a -COCI group and then by reacting with an amine of formula HNR 2 R 3 , to obtain the compound of formula (I).
- step 2) comprises the following steps:
- Stage 2b is a trans-amidification reaction and can be carried out in a known manner, in which 0.8 to 1.2 moles, preferably 0.9, are preferably used. at least 1 mole, preferably about 1 mole, of amine per mole of ester, which can in particular be used with the aid of acidic or basic catalysts, for example using potassium carbonate or
- This step can be carried out in solution, for example in aqueous solution, or in toluene solution, during which step it is possible to gradually eliminate the methanol formed in order to promote the reaction. may be accompanied by removal of the solvent, for example by an azeotrope After removal of the methanol, the removed solvent can be reintroduced into the process.
- Steps 2a ") and 2a'2) are esterification reactions from a nitrile and can be carried out in a known manner, in particular the PINNER reaction can be carried out.
- an alcohol of formula R'OH preferably in excess, This alcohol may constitute the solvent of the reaction.
- Step 2a'1) is a hydrolysis reaction. It can be implemented in a known manner, in particular by acid hydrolysis or basic hydrolysis.
- Step 2b'2) is a known reaction. It can in particular be implemented using thionyl chloride. It is accompanied by formation of hydrochloric acid.
- a base can be used to trap it, for example triethylamine (TEA).
- TAA triethylamine
- This step can be carried out with at least 0.8 molar equivalent of amine, preferably with at least one equivalent. In particular, an excess of from 1.05 to 1, 4 molar equivalents may be used.
- the addition of the alcohol, especially step 1) is preferably carried out using at least 1 molar equivalent of alcohol, relative to the alkene-nitrile. It is possible to use a large excess of alcohol, for example from 2 to 20 equivalents, in particular from 5 to 15. It is possible in particular to use the alcohol as the solvent for the reaction.
- alkene-nitriles As initial nitrile alkene compounds, it is possible in particular to use the alkene-nitriles for which:
- R c H
- R b H
- R a Et.
- It is an alkene nitrile of formula (I 1 ) of 2-pentenenitrile type (sometimes denoted 2PN). It can be in particular cis-2-pentenenitrile or trans-2-pentenenitrile.
- It can be an alkene-nitrile of formula (I 1 ) of type methyl-2-butenenitrile (sometimes noted as 2BN). It may be in particular a 2-methyl-2-butenenitrile such as cis-2-methyl-2-butenenitrile or trans-2-methyl-2-butenenitrile, or a 3-methyl-2-butenenitrile such as cis-3-methyl-2-butenenitrile or trans-3-methyl-2-butenenitrile.
- the molar ratio between the first and the second may for example be between 50/50 and 99/1, preferably between 60/40 and 90/10.
- the compound of the invention may especially be used as a surfactant, solvent, co-solvent and / or crystallization inhibitor, as a plasticizer or as a coalescing agent.
- co-solvent is meant that other solvents may be associated with it.
- the use as a solvent or a co-solvent notably comprises uses for dissolving a compound in a formulation, in a reaction medium, the use for solubilizing totally or partially a product to be eliminated.
- alkoxylated and / or propoxylated compounds are preferred, i.e. where n is not 0 in formula (I).
- the compound of the invention may especially be used, for the functions indicated above or for others, in a phytosanitary formulation, in a cleaning formulation, in a pickling formulation, in a degreasing formulation, in a formulation lubricants or textiles, in a coating formulation, for example in a paint formulation, in a pigment formulation or ink, in a plastic formulation.
- the compound may for example be used as a coalescing agent in an aqueous paint formulation.
- the compound can in particular be used as a resin solvent, for example in the cable coating industry or in the electronics industry, especially as a solvent for PVDF.
- the compound may especially be used as a cleaning and / or pickling solvent in the electronics industry. It can especially be used in lithium batteries. It can especially be used on photoresistant resins, polymers, waxes, fats, oils. The compound can in particular be used for cleaning inks, for example during the production of inks or when printing ink is used.
- the compound may especially be used for cleaning sieves or other tools used in manufacturing processes and / or recycling paper.
- the compound may in particular be used for the cleaning of bitumen or tar sand, for example on coated substrates, on the tools used to apply these materials, on contaminated clothing, on soiled vehicles.
- the compound may especially be used for cleaning flying machines such as airplanes, helicopters, space shuttles.
- the compound may especially be used as a degreasing agent on metal surfaces, for example surfaces of tools, manufactured articles, sheets, molds, in particular steel or aluminum or alloys of these metals.
- the compound can especially be used as a cleaning solvent on hard surfaces or textile surfaces.
- the compound can in particular be used as a solvent for stripping paint or resins, on tool surfaces, for example foundry molds, on surfaces of industrial sites (floors, partitions, etc.).
- the paint stripping formulations may in particular be aqueous-based formulations (the compound being in admixture with water) or solvent-based (the compound then being the solvent or a compound mixed with water).
- the compound may especially be used as a plasticizer in thermoplastic polymer formulations.
- the cleaning and / or degreasing formulations may especially be formulations for household care, operated in homes or in public areas (hotels, offices, factories, etc.). It can be a formulation for the cleaning of hard surfaces such as floors, furnishing surfaces and equipment of kitchens and bathrooms, dishes. These formulations can also be used in the industrial sphere to degrease manufactured products and / or cleaned. Such formulations may in particular be used to clean and / or strip products, tools, molds, clothes or other.
- the compound of the invention may especially be used in phytosanitary formulations comprising a solid active product. More details are given below, where the word "solvent” may refer to the compound of the invention or a composition of matter comprising it, described above.
- the phytosanitary formulation is generally a concentrated phytosanitary formulation comprising an active compound.
- the phytosanitary formulations must allow easy weight dilution by the farmer, in order to obtain a product in which the phytosanitary product is correctly dispersed, for example in the form of a solution, emulsion, suspension, or suspension. emulsion.
- the phytosanitary formulations thus allow the transport of a phytosanitary product in relatively concentrated form, easy packaging and / or easy handling for the end user.
- Different types of phytosanitary formulations can be used depending on the different plant protection products.
- Emulsifiable concentrates Emulsifiable Concentrates “EC”
- EW concentrated emulsions
- ME microemulsions
- WP wettable powders
- WDG Water Dispersible Granules
- the formulations that can be used depend on the physical form of the phytosanitary product (for example solid or liquid), and its physico-chemical properties in the presence of other compounds such as water or solvents.
- the phytosanitary product may be in various physical forms: solution, dispersion of solid particles, dispersion of droplets of the product, droplets of solvent in which the product is dissolved ...
- Phytosanitary formulations generally include compounds to obtain these physical forms. It may for example be surfactants, solvents, mineral carriers, and / or dispersants. Often these compounds do not have an active character, but a character of intermediary for formulation aid.
- the phytosanitary formulations may in particular be in liquid form, or in solid form. In order to prepare phytosanitary formulations of solid active plant protection products, it is known to solubilize the product in a solvent.
- the phytosanitary formulation thus comprises a solution of the product in the solvent.
- the formulation may be in solid form, for example in the form of a wettable powder (WP) in which the solution soaks an inorganic support, for example kaolin and / or silica.
- WP wettable powder
- the formulation may alternatively be in liquid form, for example in the form of an emulsifiable concentrate (EC) having a single clear liquid phase comprising the solvent and the product in solution, capable of forming an emulsion by adding water, without stirring or with a weak agitation. It can also be or in the form of a concentrated emulsion (EW), cloudy, whose phase dispersed in water comprises the solvent and the product in solution in the solvent. It can also be a microemulsion (ME), limpid, whose dispersed phase in water comprises the solvent and the product in solution in the solvent.
- EW concentrated emulsion
- ME microemulsion
- tebuconazole is a particularly effective and widely used fungicide for soybean cultivation in particular.
- Crystals can have negative effects, including clogging the filters of the devices used to spread the diluted composition, clog the spray devices, decrease the overall activity of the formulation, create unnecessary problems of waste streams to remove the crystals, and / or cause a bad distribution of the active product on the agricultural field.
- compositions comprising the solvent have in particular:
- the phytosanitary formulation may furthermore be a concentrated phytosanitary formulation comprising: a) an active plant protection product, b) the solvent c) optionally at least an emulsifying agent, preferably a surfactant, and d) optionally water.
- Active plant protection products especially non-water soluble and solid products are known to those skilled in the art.
- the active plant protection product may in particular be a herbicide, an insecticide, an acaricide, a fungicide, or a rodent killing agent ("rodenticide" in English) for example a rat poison.
- rodenticide rodent killing agent
- suitable active ingredients mention may be made, inter alia, of Amtretryne, Diuron, Linuron, Chlortoluron, Isoproturon, Nicosulfuron, Metamitron, Diazinon, Aclonifen and Atrazine.
- the phytosanitary formulation may comprise an emulsifying agent, typically and preferably a surfactant.
- the emulsifying agents are agents intended to facilitate the emulsification or dispersion after placing the formulation in contact with water, and / or to stabilize (in time and / or in temperature) the emulsion or the dispersion. for example by avoiding sedimentation.
- Surfactants are known compounds, which have a generally relatively low molar mass, for example less than 1000 g / mol.
- the surfactant can be an anionic surfactant in salified or acidic form, preferably polyalkoxylated nonionic, cationic, amphoteric (term also including zwitterionic surfactants). It may be a mixture or combination of these surfactants.
- anionic surfactants mention may be made, without intending to be limited thereto:
- alkylsulphonic acids arylsulphonic acids, optionally substituted with one or more hydrocarbon groups, and whose acid function is partially or totally salified, such as C 8 -C 50 alkylsulphonic acids, more in particular C 8 -C 30 , preferably C 10 -C 22 , benzenesulphonic acids, naphthalenesulphonic acids, substituted with one to three alkyl groups d-C30, preferably C 4 -C 6 , and / or alkenyls C 2 -C 30 , preferably C 4 -C 6 .
- alkylsulfosuccinic acids of which the linear or branched alkyl part, optionally substituted with one or more hydroxylated and / or alkoxylated, linear or branched C 2 -C 4 (preferably ethoxylated, propoxylated, ethopropoxylated) groups; ).
- the phosphate esters chosen more particularly from those comprising at least one saturated, unsaturated or aromatic hydrocarbon group, linear or branched, comprising 8 to 40 carbon atoms, preferably 10 to 30, optionally substituted by at least one alkoxylated (ethoxylated) group, propoxylated, ethopropoxylated).
- they comprise at least one phosphate ester group, mono- or diesterified so that one or two free acid groups or partially or totally salified.
- the preferred phosphate esters are of the mono- and diester type of phosphoric acid and of alkoxylated (ethoxylated and / or propoxylated) mono-, di- or tristyrylphenol, or of alkoxylated (ethoxylated) mono-, di- or trialkylphenol and / or propoxylated), optionally substituted with one to four alkyl groups; phosphoric acid and a C 8 -C 30 alcohol, preferably C 10 -C 22 alkoxylated (ethoxylated or ethopropoxylated); phosphoric acid and a C 8 -C 22 alcohol, preferably C 10 -C 22 , non-alkoxylated.
- sulphate esters obtained from saturated or aromatic alcohols, optionally substituted with one or more alkoxylated groups (ethoxylated, propoxylated, ethopropoxylated), and for which the sulphate functional groups are in the free acid form, or partially or completely neutralized .
- sulfate esters obtained more particularly from saturated or unsaturated C 8 -C 20 alcohols, which may comprise 1 to 8 alkoxylated units (ethoxylated, propoxylated, ethopropoxylated); sulphate esters obtained from polyalkoxylated phenol, substituted with 1 to 3 saturated or unsaturated C 2 -C 30 hydroxycarbon groups, and in which the number of alkoxylated units is between 2 and 40; sulfate esters obtained from polyalkoxylated mono-, di- or tristyrylphenol in which the number of alkoxylated units ranges from 2 to 40.
- the anionic surfactants can be in acid form (they are potentially anionic), or in partially or totally salified form, with a counterion.
- the counterion may be an alkali metal, such as sodium or potassium, an alkaline earth metal, such as calcium, or an ammonium ion of formula N (R) 4 + in which R, which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical optionally substituted by an oxygen atom.
- R which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical optionally substituted by an oxygen atom.
- alkoxylated ethoxylated, propoxylated, ethopropoxylated substituted by at least one alkyl radical C 4 -C 2 O, preferably C 4 -C 2, or substituted by at least one alkylaryl radical in which the alkyl part is Ci -C ⁇ . More particularly, the total number of alkoxylated units is between 2 and 100.
- ethoxylated and / or propoxylated, sulphated and / or phosphated di- or tristyrylphenols mention may be made of ethoxylated di- (1-phenylethyl) phenol, containing 10 oxyethylenated units, ethoxylated di (1-phenylethyl) phenol.
- alcohols or fatty acids C 6 -C 22 which are polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated).
- the number of alkoxylated units is between 1 and 60.
- ethoxylated fatty acid includes both the products obtained by ethoxylation of a fatty acid with ethylene oxide and those obtained by esterification of a fatty acid with a polyethylene glycol. .
- polyalkoxylated triglycerides ethoxylated, propoxylated, ethopropoxylated
- triglycerides from lard, tallow, peanut oil, butter oil, cottonseed oil, linseed oil, olive oil, are suitable.
- the term ethoxylated triglyceride is intended both for the products obtained by ethoxylation of a triglyceride by ethylene oxide and those obtained by ethoxylation of a triglyceride with ethylene oxide. by trans-esterification of a triglyceride with a polyethylene glycol.
- the optionally polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated) esters of sorbitan more particularly the cyclized sorbitol esters of C 10 -C 20 fatty acids such as lauric acid, stearic acid or oleic acid, and comprising a total number of alkoxylated units of between 2 and 50.
- Useful emulsifiers include the following products, all marketed by Rhodia: - Soprophor® TSP / 724: surfactant based on ethopropoxylated tristyrylphonol
- Soprophor® 796/0 surfactant based on ethopropoxylated tristyrylphonol
- Soprophor® BSU surfactant based on ethoxylated tristyrylphonol - Alkamuls® RC: surfactant based on ethoxylated castor oil
- the formulation advantageously comprises at least 4%, preferably at least 5%, preferably at least 8%, by weight of dry matter, of at least one surfactant c).
- the solvent may be combined with an aromatic and / or nonaromatic surfactant.
- the phytosanitary formulation preferably does not include significant amounts of water.
- the water content is less than 50% by weight, preferably less than 25% by weight. It will generally be less than 10% by weight.
- the formulation is preferably a liquid formulation, for example in the form of an emulsifiable concentrate (EC), a concentrated emulsion (EW) or a micoremulsion (ME). In this case, it preferably comprises less than 500 g / l of water, more preferably less than 250 g / l. It will generally be less than 100 g / L.
- the formulations may advantageously comprise: a) from 4 to 60%, preferably from 10 to 50%, of the phytosanitary product, by weight of active ingredient, b) from 10 to 92%, preferably from 20 to 80%, of the solvent by weight, c) from 4 to 60%, preferably from 5 to 50%, preferably from 8 to 25%, by weight of dry matter, of an emulsifier, preferably of a surfactant, d) of 0 at 10% by weight of water.
- solid formulations for example formulations in which a liquid comprising the phytosanitary product solubilized in the solvent, is supported by a mineral and / or dispersed in a solid matrix.
- the formulation can of course include other ingredients (or "other additives") than the active plant protection product, the solvent (s), the emulsifying agent (s) optional (s) and optional water. It may especially comprise viscosity modifiers, defoamers, especially silicone antifoams, anti-rebound agents, anti-leaching agents, inert fillers, in particular mineral fillers, anti-freeze agents, etc.
- the formulations may comprise additives, known as other additives, that do not fall within the definition of products a), b), or c), such as:
- solvents generally in small amounts, that is to say, less than the solvent of the solvent system being present in the smallest amount.
- Another solvent is not meant to be part of the solvent system.
- solvents of the family of phosphates, phosphonates or phosphine oxides such as TEBP, TBP, TEPO, DBBP.
- Mention may also be made of alkyldimethyleamides in which the alkyl is C 6 -C 8 , in particular those sold under the trademark Genagen.
- Ester lactates especially those marketed under the trademark Purasolv, are also mentioned.
- Mention is also made of methyl esters of fatty acids, in particular those marketed under the trade name Phytorobe.
- Diacid diesters (“DiBasic Esters”) are also mentioned, in particular those marketed by Rhodia under the trade names Rhodiasolv RPDE and Rhodiasolv DIB. Also mentioned are hydrocarbon cuts, cyclic amides such as NMP, lactones. The bis (dialkylamides) described in WO 2008/074837 are also mentioned.
- crystallization inhibitors can be solvents mentioned above. It may also be fatty acids or non-polyalkoxylated fatty alcohols. For example, mention is made of the product Alkamuls® OL700 marketed by Rhodia.
- the concentrated phytosanitary formulation is intended to be spread over a cultivated field or to be cultivated, for example a soybean field, most often after dilution in water, to obtain a diluted composition.
- Dilution is generally carried out by the farmer, directly in a tank ("tank-mix"), for example in the tank of a device for spreading the composition.
- tank-mix a tank
- the operator adds other phytosanitary products, for example fungicides, herbicides, pesticides, insecticides, fertilizers.
- the formulation can be used to prepare a composition diluted in the water of the active plant protection product, by mixing at least one part by weight of concentrated formulation with at least 10 parts of water, preferably less than 1000 parts. Dilution rates and quantities to apply on the field usually depend on the phytosanitary product and the desired dose to treat the field; this can be determined by the farmer.
- stage 3 product (3-isopentyloxy pentanoic acid) with a purity of 98%.
- the triethylammonium chloride formed is removed by filtration and washed with twice 300 ml of toluene.
- the toluene phases are combined and the toluene is removed by evaporation.
- the product is then washed with an aqueous solution of sodium hydrogencarbonate to pH 7-8 and extracted with ethyl acetate.
- the ethyl acetate is removed by evaporation and the product purified by fractional distillation (boiling point: 105 ° C / 100 Pa).
- Example 2 Preparation of CH 2 CH 2 CH (OMe) - (CH 3 VCONM 3
- the procedure is as for Example 1, replacing the isoamyl alcohol with methanol.
- the synthetic route is as follows:
- Stage 1 product (3-cyclohexanoxy pentanenitrile) are obtained with a purity higher than 90%.
- the organic phase is treated with 120 g of cyclohexane and concentrated under partial vacuum (pressure ⁇ 21 mbar / mass temperature ⁇ 50 ° C.).
- Reaction mass obtained 729 g of a pale yellow solution. It is composed of 93% CH3-CH 2 -CH (OCyclo) - (CH 2 ) -CONMe2
- formulations of various phytosanitary active agents, of the emulsifiable concentrated type (EC), are prepared.
- the formulations include:
- active ingredient in quantity by weight (of active material) indicated in the table below, 10% by weight of surfactant Alkamuls RC, marketed by Rhodia
- Examples 4 are comparative examples in which the product Rhodiasolv® ADMA10, Rhodia (Asia-Pacific zone) is used as solvent: Alkydimethylamide solvent.
- a crystal of the active ingredient is introduced into the formulation having spent 7 days at 0 ° C. for nucleation, and the formulation is again placed for 7 days at 0 ° C. appearance of the formulation and the presence of crystals is optionally identified.
- Geronol® TBE-724 (surfactant, Rhodia) 150 g / L
- Emulsification (Cipac test, at 1% concentration at 30 ° C., after 24 hours
- Emulsification (Cipac test, at 1% concentration at 30 ° C., after 4 hours
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0907679-4A BRPI0907679B1 (pt) | 2008-04-30 | 2009-04-30 | "composition, process for preparing a compound and using compound" |
EA201071253A EA201071253A1 (ru) | 2008-04-30 | 2009-04-30 | Соединения типа простой эфир/амид, способ получения и применение |
EP09738225.3A EP2280936B1 (fr) | 2008-04-30 | 2009-04-30 | Composes de type ether-amide, procede de preparation et utilisations |
JP2011506726A JP2011518867A (ja) | 2008-04-30 | 2009-04-30 | エーテルアミド型化合物、その製造方法及び使用 |
US12/990,293 US8969621B2 (en) | 2008-04-30 | 2009-04-30 | Ether-amide compounds and preparation and uses thereof |
CA2723004A CA2723004A1 (fr) | 2008-04-30 | 2009-04-30 | Composes de type ether-amide, procede de preparation et utilisations |
CN200980121327.1A CN102056893B (zh) | 2008-04-30 | 2009-04-30 | 醚-酰胺型化合物、制备方法及用途 |
AU2009242087A AU2009242087B2 (en) | 2008-04-30 | 2009-04-30 | Ether-amide type compounds, preparation method and uses |
US14/468,516 US9371273B2 (en) | 2008-04-30 | 2014-08-26 | Ether-amide compounds and preparation and uses thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0802433 | 2008-04-30 | ||
FR0802433A FR2930774B1 (fr) | 2008-04-30 | 2008-04-30 | Composes de type ether-amide, procede de preparation et utilisation |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/990,293 A-371-Of-International US8969621B2 (en) | 2008-04-30 | 2009-04-30 | Ether-amide compounds and preparation and uses thereof |
US14/468,516 Continuation US9371273B2 (en) | 2008-04-30 | 2014-08-26 | Ether-amide compounds and preparation and uses thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009133181A1 true WO2009133181A1 (fr) | 2009-11-05 |
Family
ID=40111110
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2009/055287 WO2009133181A1 (fr) | 2008-04-30 | 2009-04-30 | Composes de type ether-amide, procede de preparation et utilisations |
Country Status (13)
Country | Link |
---|---|
US (2) | US8969621B2 (fr) |
EP (1) | EP2280936B1 (fr) |
JP (1) | JP2011518867A (fr) |
KR (1) | KR20100135867A (fr) |
CN (1) | CN102056893B (fr) |
AR (1) | AR073931A1 (fr) |
AU (1) | AU2009242087B2 (fr) |
BR (1) | BRPI0907679B1 (fr) |
CA (1) | CA2723004A1 (fr) |
EA (1) | EA201071253A1 (fr) |
FR (1) | FR2930774B1 (fr) |
TW (1) | TW200951105A (fr) |
WO (1) | WO2009133181A1 (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011012562A3 (fr) * | 2009-07-31 | 2011-10-20 | Basf Se | Composition liquide contenant un pesticide, un tensioactif non ionique et un amide propionique |
EP2390289A1 (fr) * | 2010-05-26 | 2011-11-30 | Seiko Epson Corporation | Composition d'encre non aqueuse pour impression par jet d'encre et procédé d'impression par jet d'encre |
WO2014016389A1 (fr) * | 2012-07-26 | 2014-01-30 | Rhodia Operations | Compositions phytosanitaires comprenant un composé éther-amide |
US8840233B2 (en) | 2010-09-03 | 2014-09-23 | Seiko Epson Corporation | Ink jet recording-targeted non-aqueous ink composition, ink set, and ink jet recording method |
US8936358B2 (en) | 2010-05-26 | 2015-01-20 | Seiko Epson Corporation | Ink composition for ink jet textile printing and ink jet textile printing process |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2930774B1 (fr) * | 2008-04-30 | 2010-09-17 | Rhodia Operations | Composes de type ether-amide, procede de preparation et utilisation |
EP2846935B1 (fr) * | 2012-05-10 | 2017-07-26 | Basf Se | Alcools alcoxylés et leur utilisation dans des formulations de nettoyage de surfaces dures |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2704280A (en) * | 1951-05-29 | 1955-03-15 | Colgate Palmolive Co | Long-chain aliphatic ether-amides in detergent compositions |
JP2005047885A (ja) * | 2003-07-17 | 2005-02-24 | Idemitsu Kosan Co Ltd | β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法 |
JP2008031112A (ja) * | 2006-07-31 | 2008-02-14 | Idemitsu Kosan Co Ltd | アルコキシ−n−イソプロピル−プロピオンアミド及びそれを用いた溶剤又は洗浄剤 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2719176A (en) * | 1953-02-05 | 1955-09-27 | Eastman Kodak Co | Continuous method of making n-substituted amides |
ES251290A1 (es) * | 1958-08-21 | 1960-04-01 | Parke Davis & Co | Un procedimiento para la producciën de alcohilaminas arilsustituidas |
US3904635A (en) * | 1969-02-04 | 1975-09-09 | Asahi Chemical Ind | Method for preparing n-alkyl-' ,' -unsaturated amide |
JPS52286A (en) * | 1975-05-27 | 1977-01-05 | Kyorin Pharmaceut Co Ltd | Method of preparing 1-(3-phenylpropyl)-4-acylpiperazine derivatives |
CH629939A5 (de) * | 1977-03-29 | 1982-05-28 | Ciba Geigy Ag | Mikrobizides mittel. |
DE3109783A1 (de) * | 1981-03-13 | 1982-10-07 | Sanol Schwarz-Monheim Gmbh, 4019 Monheim | Mit wasser zu einer etwa isotonischen nitroglycerinloesung aufloesbare zubereitung und derartige nitroglycerinloesung |
JPH02124858A (ja) * | 1987-08-28 | 1990-05-14 | Mitsui Toatsu Chem Inc | 不飽和カルボン酸アミドの製造方法 |
JPH0245456A (ja) * | 1988-08-05 | 1990-02-15 | Mitsui Toatsu Chem Inc | 不飽和カルボン酸アミドの製造方法 |
JPH082850B2 (ja) * | 1988-09-20 | 1996-01-17 | 三井東圧化学株式会社 | 不飽和カルボン酸アミドの製造方法 |
JP2598488B2 (ja) * | 1988-09-26 | 1997-04-09 | 三井東圧化学株式会社 | 不飽和カルボン酸アミドの製造方法 |
JPWO2006075373A1 (ja) * | 2005-01-13 | 2008-06-12 | 出光興産株式会社 | β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法 |
FR2930774B1 (fr) * | 2008-04-30 | 2010-09-17 | Rhodia Operations | Composes de type ether-amide, procede de preparation et utilisation |
FR2951447B1 (fr) * | 2009-10-19 | 2012-10-19 | Rhodia Operations | Composes de type ether-amide et utilisattions |
-
2008
- 2008-04-30 FR FR0802433A patent/FR2930774B1/fr not_active Expired - Fee Related
-
2009
- 2009-04-30 TW TW098114504A patent/TW200951105A/zh unknown
- 2009-04-30 CN CN200980121327.1A patent/CN102056893B/zh active Active
- 2009-04-30 KR KR1020107024411A patent/KR20100135867A/ko not_active Application Discontinuation
- 2009-04-30 WO PCT/EP2009/055287 patent/WO2009133181A1/fr active Application Filing
- 2009-04-30 BR BRPI0907679-4A patent/BRPI0907679B1/pt not_active IP Right Cessation
- 2009-04-30 US US12/990,293 patent/US8969621B2/en not_active Expired - Fee Related
- 2009-04-30 EP EP09738225.3A patent/EP2280936B1/fr active Active
- 2009-04-30 CA CA2723004A patent/CA2723004A1/fr not_active Abandoned
- 2009-04-30 AU AU2009242087A patent/AU2009242087B2/en not_active Ceased
- 2009-04-30 JP JP2011506726A patent/JP2011518867A/ja not_active Abandoned
- 2009-04-30 AR ARP090101564A patent/AR073931A1/es not_active Application Discontinuation
- 2009-04-30 EA EA201071253A patent/EA201071253A1/ru unknown
-
2014
- 2014-08-26 US US14/468,516 patent/US9371273B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2704280A (en) * | 1951-05-29 | 1955-03-15 | Colgate Palmolive Co | Long-chain aliphatic ether-amides in detergent compositions |
JP2005047885A (ja) * | 2003-07-17 | 2005-02-24 | Idemitsu Kosan Co Ltd | β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法 |
JP2008031112A (ja) * | 2006-07-31 | 2008-02-14 | Idemitsu Kosan Co Ltd | アルコキシ−n−イソプロピル−プロピオンアミド及びそれを用いた溶剤又は洗浄剤 |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011012562A3 (fr) * | 2009-07-31 | 2011-10-20 | Basf Se | Composition liquide contenant un pesticide, un tensioactif non ionique et un amide propionique |
EP2390289A1 (fr) * | 2010-05-26 | 2011-11-30 | Seiko Epson Corporation | Composition d'encre non aqueuse pour impression par jet d'encre et procédé d'impression par jet d'encre |
US8936358B2 (en) | 2010-05-26 | 2015-01-20 | Seiko Epson Corporation | Ink composition for ink jet textile printing and ink jet textile printing process |
US9056992B2 (en) | 2010-05-26 | 2015-06-16 | Seiko Epson Corporation | Nonaqueous ink composition for ink jet recording and ink jet recording method |
US8840233B2 (en) | 2010-09-03 | 2014-09-23 | Seiko Epson Corporation | Ink jet recording-targeted non-aqueous ink composition, ink set, and ink jet recording method |
WO2014016389A1 (fr) * | 2012-07-26 | 2014-01-30 | Rhodia Operations | Compositions phytosanitaires comprenant un composé éther-amide |
FR2993752A1 (fr) * | 2012-07-26 | 2014-01-31 | Rhodia Operations | Compositions phytosanitaires comprenant un compose ether-amide |
Also Published As
Publication number | Publication date |
---|---|
CN102056893B (zh) | 2015-05-20 |
TW200951105A (en) | 2009-12-16 |
JP2011518867A (ja) | 2011-06-30 |
AU2009242087B2 (en) | 2013-01-24 |
FR2930774B1 (fr) | 2010-09-17 |
KR20100135867A (ko) | 2010-12-27 |
FR2930774A1 (fr) | 2009-11-06 |
US20140364648A1 (en) | 2014-12-11 |
BRPI0907679A2 (pt) | 2015-07-14 |
CA2723004A1 (fr) | 2009-11-05 |
US8969621B2 (en) | 2015-03-03 |
EA201071253A1 (ru) | 2011-06-30 |
EP2280936A1 (fr) | 2011-02-09 |
EP2280936B1 (fr) | 2018-08-15 |
US9371273B2 (en) | 2016-06-21 |
US20110263898A1 (en) | 2011-10-27 |
AR073931A1 (es) | 2010-12-15 |
AU2009242087A1 (en) | 2009-11-05 |
BRPI0907679B1 (pt) | 2017-12-12 |
CN102056893A (zh) | 2011-05-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2712318C (fr) | Utilisation d'esteramides a titre de solvants, esteramides en tant que tels et procede de preparation d'esteramides | |
EP2102148B1 (fr) | Nouveaux composes bis(dialkylamides), procede de preparation et utilisations | |
EP2280936B1 (fr) | Composes de type ether-amide, procede de preparation et utilisations | |
EP2547199B1 (fr) | Nouvelles utilisations de composes de type esteramide | |
EP2328862B1 (fr) | Produit comprenant des diamides, procede de preparation et utilisations | |
EP2547651B1 (fr) | Composes de type esteramide, leurs procedes de preparation et leurs utilisations | |
EP2961739A2 (fr) | Derives du furfural a titre de vehicule | |
EP2491008B1 (fr) | Composes de type ether-amide et utilisations | |
FR2926699A1 (fr) | Utilisation d'esteramides, nouveaux esteramides et procede de preparation d'esteramides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200980121327.1 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 09738225 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2009242087 Country of ref document: AU Ref document number: 2009738225 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2723004 Country of ref document: CA Ref document number: 6950/CHENP/2010 Country of ref document: IN |
|
ENP | Entry into the national phase |
Ref document number: 20107024411 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2011506726 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 2009242087 Country of ref document: AU Date of ref document: 20090430 Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 201071253 Country of ref document: EA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12990293 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: PI0907679 Country of ref document: BR Kind code of ref document: A2 Effective date: 20101028 |