WO2001008481A1 - Preparations pesticides contenant des polyglycerines ou des derives de polyglycerine - Google Patents

Preparations pesticides contenant des polyglycerines ou des derives de polyglycerine Download PDF

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Publication number
WO2001008481A1
WO2001008481A1 PCT/EP2000/006771 EP0006771W WO0108481A1 WO 2001008481 A1 WO2001008481 A1 WO 2001008481A1 EP 0006771 W EP0006771 W EP 0006771W WO 0108481 A1 WO0108481 A1 WO 0108481A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
crc
alkoxy groups
polyglycerol
optionally substituted
Prior art date
Application number
PCT/EP2000/006771
Other languages
German (de)
English (en)
Inventor
Ralf Zerrer
Gerd Roland Meyer
Franz Xaver Scherl
Original Assignee
Clariant Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE1999136092 external-priority patent/DE19936092A1/de
Priority claimed from DE2000123153 external-priority patent/DE10023153A1/de
Application filed by Clariant Gmbh filed Critical Clariant Gmbh
Publication of WO2001008481A1 publication Critical patent/WO2001008481A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48—Polymers modified by chemical after-treatment
    • 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
    • A01N25/30—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 characterised by the surfactants
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives

Definitions

  • the invention relates to pesticide preparations containing polyglycerols and / or polyglycerol derivatives with improved biological activity of the pesticides (herbicides, insecticides, fungicides, bactericides, molluscids, nematicides and rodenticides).
  • pesticides insecticides, fungicides, bactericides, molluscids, nematicides and rodenticides.
  • Plant protection products are chemical or natural substances that are found in
  • Plant cells, tissues or parasitic organisms enter or damage the plant and / or destroy it.
  • the majority of pesticides are herbicides, followed by insecticides and fungicides.
  • the most important herbicides are chemical substances which act on the transport system of plants, for example by inhibiting photosynthesis, fatty acid biosynthesis or amino acid biosynthesis, and which inhibit nucleation and growth or cause the plant to die.
  • the biological activity of a pesticide can be determined on the basis of the growth of the plant or the damage to the plants by the action of the active compound on the leaf, depending on the action time and the action concentration. In order to optimally develop the pesticidal effect, the pesticide must wet the leaf green and remain there for a sufficient time or penetrate the
  • Active substance can be reached through the leaf surface.
  • a general problem is that only a fraction of the active ingredient develops the desired activity, i.e. applied to harmful plants and grasses and can adhere there long enough to penetrate the plant cells. The vast majority is lost unused.
  • the mostly aqueous pesticide Formulations are added to auxiliaries which improve the wetting ability, the solubility, the emulsifying power or the adsorption behavior of the active substance. Furthermore, additives can facilitate and accelerate the penetration of the active substances through the leaf surface into the plant.
  • WO 98/06259 describes a method for supporting the biological activity of crop protection agents, according to which an aqueous surfactant solution is sprayed onto the plants as a co-formulation with or after the application of the active substance.
  • Aqueous organosilicon and / or organofluorine compounds are used as the wetting agent.
  • the herbicide N-phosphonomethylglycine (glyphosate) oils are added as water-in-oil emulsions in order to improve the contact of the hydrophilic active substance with the lipophilic epidermis of the plants.
  • the disadvantage is the insufficient stability of the emulsions.
  • the action of anionic pesticides can be improved by formulating the anionic active substance together with protonated polyamines or their derivatives as an aqueous colloidal dispersion.
  • a water-soluble salt for example as an alkali metal, ammonium, alkylamine, alkylsulfonium, alkylphosphonium, sulfonylamine or aminoguanidine salt or as a free acid in aqueous formulations, but also in solid form with wetting agents on leaves and grasses, where it affects the plant's transport system and destroys it.
  • the invention relates to pesticide preparations containing polyglycerols and / or polyglycerol derivatives of the formula (I)
  • radicals R 1 , R 2 and R 3 are, independently of one another, the same or different and a radical, or in the case of R 3 optionally a combination of radicals selected from the group
  • Phenyl optionally substituted by 1 to 3 (CC 4 ) alkyl or (-C-C 4 ) alkoxy groups; Naphthyl, optionally by 1 to 3 (-CC 4 ) -alkyl- or (C1-C4) -
  • R a is hydrogen, (CrC 30 ) -alkyl, optionally substituted by 1 to 3 (CrC 4 ) -alkyl or (C- ⁇ -C 4 ) -alkoxy groups, (C 2 -C 30 ) alkenyl, optionally sulfonated and optionally substituted by 1 to 3 (CrC 4 ) alkyl or (-C-C) alkoxy groups, phenyl, optionally by 1 to 3 (dC 4 ) - alkyl or (-C-C 4 ) -Alkoxy groups substituted, naphthyl, optionally substituted by 1 to 3 (CrC) -alkyl or (CrC 4 ) -alkoxy groups, or R a for a group selected from the formulas
  • RR 5 N-CH- (CH 2 ) X R 6 ;
  • RR 5 is N- (CH 2 ) y - or HO- (CH 2 ) y -, where n is a number from 4 to 40, preferably 5 to 20, in particular 5 to 20;
  • R 4 and R 5 which may be the same or different, for hydrogen, (C 1 -C 8) alkyl, (C 2 -C 30 ) alkenyl, optionally sulfonated, or for a group of the formula - (AO) zH;
  • R 6 is hydrogen, -CONH 2 , -COOH, -SCH 3 or -NH 2 ;
  • R 7 for (d-do-alkylene), (C 2 -C 30 ) alkenyl, optionally sulfonated;
  • X + is Na + , K + , Ca 2+ or N (R 8 ) 4 + , where R 8 is H or (CrC ⁇ o) alkyl
  • Pesticide preparations according to the invention are also to be regarded as those which contain polyglycerol mixtures, polyglycerol / polyglycerol derivative mixtures and / or polyglycerol derivative mixtures.
  • polyglycerol derivatives it should also be understood to mean polyglycerols.
  • the adjuvant polyglycerol derivative used according to the invention shows an improvement in the compatibility and the contact ability of the hydrophilic active substance with the lipophilic epidermis Plants.
  • a good wetting and absorption capacity of the pesticide formulation according to the invention supports the biological activity of the active ingredient in the plants.
  • Polyglycerol derivatives are obtained by polycondensation of glycerol under alkaline conditions, if appropriate in the presence of alcohols, and subsequent reaction with fatty acids, fatty acid alkyl esters or also fatty acid chlorides or fatty acid anhydrides, or by reaction with amino acids, lactams or lactones after ring opening.
  • glycerin and possibly fatty alcohol are heated to 200 - 280 ° C.
  • the polyglycerol derivative is formed within 24 to 72 hours.
  • the hydroxyl number (OH number) of such a reaction mixture is 825-846 mg KOH / g.
  • the pH can be adjusted to 3-5 and by adding fatty acids, such as e.g. Coconut fatty acid, fatty acid alkyl esters or also fatty acid chlorides or fatty acid anhydrides or amino acids, lactams or lactones, the polyglycerol derivative are esterified.
  • fatty acids such as e.g. Coconut fatty acid, fatty acid alkyl esters or also fatty acid chlorides or fatty acid anhydrides or amino acids, lactams or lactones, the polyglycerol derivative are esterified.
  • the reaction is complete after 4-8 h.
  • the reaction is controlled by determining the residual acid number, which should be ⁇ 1 after the reaction has ended. After the reaction mixture has cooled to 60-100.degree. C., the mixture is diluted to an active substance content of 40-70% with demineralized water and a pH of 6-7 is established by adding alkali metal hydroxide.
  • the polyglycerol derivatives used according to the invention are mixtures of compounds of the above-mentioned formula with different values for n, including unreacted glycerol.
  • the R 3 radicals are incorporated into the polyglycerol derivatives (sulfation, phosphation, amination, etc.) by the standard methods known to those skilled in the art.
  • the polyglycerol derivatives are suitable as adjuvants in pesticide formulations for improving the biological activity of herbicides, insecticides, fungicides, acaricides, bactericides, molluscids, nematicides and rodenticides.
  • the polyglycerol derivatives are suitable as adjuvants in pesticide formulations for improving the biological activity of herbicides, insecticides, fungicides, acaricides, bactericides, molluscids, nematicides and rodenticides.
  • the polyglycerol derivatives are suitable as adjuvants in pesticide formulations for
  • Suitable herbicides are, without restricting the invention to these, in particular glyphosates, their salts and / or derivatives, but also acifluorfen, asulam, benazolin, bentazone, bilanafos, bromacil, bromoxynil, chloramben, clopyralide, 2,4-D, 2,4 -DB, Dalapon, Dicamba, Dichlorprop, Diclofop, Endothall, Fenac, Fenoxaprop, Flamprop, Fluazifop, Flumiclorac, Fluoroglycofen, Fornesafen, Fosamine, Glufosinate, Haloxyfop, Imazapic, Imazamethabenz, Imazamox, MazyrpCP, Imazamethazz , Mecoprop, Methylarsonic acid / MSMA, Naptalam, Picloram, Quinclorac, Quizalofop, 2,3,6-TBA and TCA
  • the preparations according to the invention can contain the polyglycerol derivatives in almost any amount.
  • the following preparations are preferred:
  • Formulations as "tank mix” and “ready to use compositions” contain 0.001 to 10% by weight, preferably 0.05 to 2% by weight of pesticide and 0.01% by weight to 10% by weight .-%, preferably 0.1% to 2%, particularly preferably 0.2% to 1% polyglycerol derivative.
  • the weight ratio of polyglycerol derivative to pesticide can be between 1:10 to 500: 1, in particular 1: 4 to 4: 1.
  • Concentrate formulations which are diluted before use can contain the pesticide in the amounts by weight of 5 to 60%, preferably 20 to 40% and the polyglycerol derivative in amounts of 3% by weight to 50% by weight.
  • the weight ratio of polyglycerol derivative to pesticide can be between 1:20 to 1: 1, preferably 1:10 to 1: 2.
  • the formulations according to the invention can be prepared in solid form as powders, pellets, tablets or granules, which are dissolved in water before use.
  • Solid preparations can the pesticide in the weight of 20% to 80%, preferably from 50% to 75%, particularly preferably from 60% to 70% and the polyglycerol derivative in weight amounts of 5% to 50%, preferably 10% to 30%.
  • the formulations according to the invention can furthermore contain the customary thickeners, anti-gel agents, freezing agents, solvents, dispersants, emulsifiers, preservatives, further adjuvants, binders, anti-foaming agents, thinners, disintegrants and wetting agents.
  • xanthan gum As a thickener, xanthan gum and / or cellulose, for example
  • Carboxy, methyl, ethyl or propyl cellulose in amounts by weight of 0.01 to 5% based on the finished agent can be used.
  • solvents are suitable as solvents
  • Monopropylene glycol animal and mineral oils.
  • Nonionic, amphoteric, cationic and anionic surfactants are suitable as dispersants and emulsifiers.
  • Organic acids and their esters for example ascorbic acid, ascorbic palmitate, sorbate, benzoic acid, methyl- and propyl-4-, can be used as preservatives.
  • Suitable defoamers are e.g. Polysilicone.
  • Other adjuvants can e.g. Alcohol ethoxylates, alkyl polysaccharides,
  • Alk (en) ylsuccinic anhydride Alk (en) ylsuccinic anhydride.
  • the mixing ratio of these adjuvants to the polyglycerol derivative can be in the range from 1:10 to 10: 1.
  • polyvinyl pyrrolidone polyvinyl alcohol
  • carboxymethyl cellulose for example sucrose, sorbitol, or starch are suitable as binders.
  • Carbon black, tallow, kaolin, aluminum, calcium or magnesium stearate, sodium tripolyphosphate, sodium tetraborate, sodium sulphate, silicates and sodium benzoate are suitable as thinners, absorbers or carriers.
  • Cellulose for example carboxymethyl cellulose, polyvinylpyrrolidone, sodium or potassium acetate, carbonates, bicarbonates, sesquicarbonates, act as disintegrants.
  • Alcohol ethoxylates / propoxylates can be used as wetting agents.
  • a great technical advantage of the pesticide preparations according to the invention is their high salt stability, in particular that of the pesticide polyglyceryl alkyl ester preparations; in an aqueous medium even with a high pesticide concentration.
  • formulations according to the invention can be used in accordance with the customary methods.
  • Aqueous concentrates and solid formulations are diluted with the appropriate amount of water before application.
  • Pesticide amounts in the range of 0.1 to 5 kg, preferably 0.3 to 2.5 kg, are applied per hectare.
  • the proportion of the adjuvant polyglycerol derivative according to the invention is in the range from 0.1 to 3.0 kg / ha.
  • the volume of the pesticide formulation created for spraying is in the range from 50 to 1000 l / ha.
  • the invention also relates to a method for increasing the biological activity of pesticides, which is characterized in that the pesticides are used in the form of pesticide preparations containing polyglycerols and / or polyglycerol derivatives according to formula (I).
  • the method is preferably suitable for herbicides, in particular for glyphosates, their salts and / or derivatives.
  • Glyphosate N-phosphonomethylglycine
  • alkali metal ammonium
  • alkylamine alkylsulfonium
  • alkylphosphonium alkylphosphonium
  • aminoguanidine salt aminoguanidine
  • the aqueous composition according to the invention has a pH of 4 to 8, preferably 6 to 7.
  • polyglycerol 500 g are introduced with stirring and, while simultaneously introducing nitrogen at 80 ° C., the pH is adjusted to 5 with 5% phosphoric acid (aqueous). The pH is measured in a 1% aqueous solution. Then 87.4 g of coconut fatty acid (Cs) are added and one Nitrogen throughput heated from 0.1 m / h to 230 ° C. After reaching an acid number of ⁇ 0.5 mg KOH / g in about 5 to 12 hours at 230 ° C, the experiment is ended.
  • the other polyglycerol esters are prepared from polyglycerol and other fatty acids analogously to the above regulation. The key figures of the polyglycerol esters produced are listed in Table 2.
  • Table 3 Composition of the polyglycerol esters I - VI of the formula (II): Test formulations are prepared, each containing 200 g, 300 g and 500 g of glyphosate and 600 g of the polyglycerol esters I-VI in 300 l of water. The weights are based on 100% active ingredient and 100% adjuvant.
  • a formulation amount corresponding to the ratio of 300 l / ha is applied in a greenhouse to the plant species Abutilon theophrasti (ABUTH), Sesbania exaltata (SEBEX), Pharbitis purpurea (PHBPU), Galium aparine (GALAP), Amaranthus retroflexus (AMARE), Echinochloa crus (ECHCG) and after 21 days at 20 ° C the plant growth was assessed on a scale. 0% of the measurement scale stands for no effect, 100% for a complete death of all plant species mentioned above.
  • the influence of the polyglycerol esters (adjuvants) I - VI on the herbicidal action of glyphosate is shown in Table 4.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Wood Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Préparations pesticides contenant des polyglycérines et/ou des dérivés de polyglycérine de formule (I) en tant qu'adjuvant. Dans ladite formule, R?1, R2 et R3¿ représentent hydrogène ou les radicaux cités dans le descriptif et n représente des valeurs entre 4 et 40. Lesdites préparations sont de préférence des préparations herbicides.
PCT/EP2000/006771 1999-07-30 2000-07-15 Preparations pesticides contenant des polyglycerines ou des derives de polyglycerine WO2001008481A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE1999136092 DE19936092A1 (de) 1999-07-30 1999-07-30 Polyglycerinester enthaltende Pestizidzubereitungen
DE19936092.8 1999-07-30
DE2000123153 DE10023153A1 (de) 2000-05-12 2000-05-12 Pestizidzubereitungen enthaltend Polyglycerine oder Polyglycerinderivate
DE10023153.5 2000-05-12

Publications (1)

Publication Number Publication Date
WO2001008481A1 true WO2001008481A1 (fr) 2001-02-08

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002089575A1 (fr) * 2001-04-10 2002-11-14 Clariant Gmbh Preparations pesticides renfermant des copolymeres
WO2003000055A1 (fr) * 2001-06-23 2003-01-03 Clariant Gmbh Preparations pesticides contenant des copolymeres
DE10307171A1 (de) * 2003-02-20 2004-09-09 Clariant Gmbh Copolymere enthaltende landwirschaftliche Mittel
EP1344518A3 (fr) * 2002-03-16 2006-05-17 Clariant Produkte (Deutschland) GmbH Compositions cosmétiques et pharmaceutiques contenant des esters de polyglycerol oxyalkylés
EP1905302A1 (fr) * 2006-09-30 2008-04-02 Bayer CropScience AG Suspensions concentrées
US7553495B2 (en) 2003-09-15 2009-06-30 Clariant Produkte (Deutschland) Gmbh Liquid compositions comprising oxyalkylated polyglycerol esters
EP2384624A1 (fr) * 2010-05-08 2011-11-09 Cognis IP Management GmbH Compositions biocides comportant des esters d'oligoglycérol alkoxylés
US8466100B2 (en) 2008-08-15 2013-06-18 The Procter & Gamble Company Benefit compositions comprising polyglycerol esters
US8759255B2 (en) 2009-09-10 2014-06-24 Clariant Finance (Bvi) Limited Pesticide preparations
EP3199589A1 (fr) 2016-01-29 2017-08-02 Evonik Degussa GmbH Ester d'alcoxylate poly glycérol sa fabrication et son utilisation

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Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002089575A1 (fr) * 2001-04-10 2002-11-14 Clariant Gmbh Preparations pesticides renfermant des copolymeres
US7407667B2 (en) 2001-04-10 2008-08-05 Clariant Produkte (Deutschland) Gmbh Pesticidal preparations comprising copolymers
KR100862876B1 (ko) * 2001-04-10 2008-10-15 클라리안트 프로두크테 (도이칠란트) 게엠베하 공중합체를 포함하는 농약 제제
WO2003000055A1 (fr) * 2001-06-23 2003-01-03 Clariant Gmbh Preparations pesticides contenant des copolymeres
KR100862878B1 (ko) * 2001-06-23 2008-10-15 클라리안트 프로두크테 (도이칠란트) 게엠베하 공중합체를 함유하는 농약 제제
EP1344518A3 (fr) * 2002-03-16 2006-05-17 Clariant Produkte (Deutschland) GmbH Compositions cosmétiques et pharmaceutiques contenant des esters de polyglycerol oxyalkylés
US7709011B2 (en) 2002-03-16 2010-05-04 Clariant Produkte (Deutschland) Gmbh Cosmetic or pharmaceutical preparations comprising an oxalkylated polyglycerol ester
DE10307171B4 (de) * 2003-02-20 2009-04-16 Clariant Produkte (Deutschland) Gmbh Copolymere enthaltende landwirschaftliche Mittel
DE10307171A1 (de) * 2003-02-20 2004-09-09 Clariant Gmbh Copolymere enthaltende landwirschaftliche Mittel
JP2006518349A (ja) * 2003-02-20 2006-08-10 クラリアント・プロドゥクテ・（ドイチュラント）・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング コポリマー含有農薬組成物
US7553495B2 (en) 2003-09-15 2009-06-30 Clariant Produkte (Deutschland) Gmbh Liquid compositions comprising oxyalkylated polyglycerol esters
WO2008037375A2 (fr) * 2006-09-30 2008-04-03 Bayer Cropscience Ag Concentrés de suspension
EP1905302A1 (fr) * 2006-09-30 2008-04-02 Bayer CropScience AG Suspensions concentrées
US7977278B2 (en) 2006-09-30 2011-07-12 Bayer Cropscience Ag Suspension concentrates
WO2008037375A3 (fr) * 2006-09-30 2008-05-29 Bayer Cropscience Ag Concentrés de suspension
KR101444198B1 (ko) 2006-09-30 2014-10-02 바이엘 크롭사이언스 아게 현탁 농축물
US8466100B2 (en) 2008-08-15 2013-06-18 The Procter & Gamble Company Benefit compositions comprising polyglycerol esters
US8759255B2 (en) 2009-09-10 2014-06-24 Clariant Finance (Bvi) Limited Pesticide preparations
EP2384624A1 (fr) * 2010-05-08 2011-11-09 Cognis IP Management GmbH Compositions biocides comportant des esters d'oligoglycérol alkoxylés
CN102970866A (zh) * 2010-05-08 2013-03-13 考格尼斯知识产权管理有限责任公司 包含烷氧基化低聚甘油酯的生物杀伤剂组合物
WO2011141093A1 (fr) * 2010-05-08 2011-11-17 Cognis Ip Management Gmbh Compositions biocides contenant des esters d'oligoglycérine alcoxylés
US8980867B2 (en) 2010-05-08 2015-03-17 Cognis Ip Management Gmbh Biocide compositions comprising alkoxylated oligoglycerol esters
CN102970866B (zh) * 2010-05-08 2015-10-07 考格尼斯知识产权管理有限责任公司 包含烷氧基化低聚甘油酯的生物杀伤剂组合物
EP3199589A1 (fr) 2016-01-29 2017-08-02 Evonik Degussa GmbH Ester d'alcoxylate poly glycérol sa fabrication et son utilisation
US10370493B2 (en) 2016-01-29 2019-08-06 Evonik Degussa Gmbh Polyglycerol alkoxylate esters and preparation and use thereof

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