EP2190959A1 - Verwendung von carbonsäurediestern zur behandlung von textilien und formulierung dafür - Google Patents

Verwendung von carbonsäurediestern zur behandlung von textilien und formulierung dafür

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Publication number
EP2190959A1
EP2190959A1 EP08775148A EP08775148A EP2190959A1 EP 2190959 A1 EP2190959 A1 EP 2190959A1 EP 08775148 A EP08775148 A EP 08775148A EP 08775148 A EP08775148 A EP 08775148A EP 2190959 A1 EP2190959 A1 EP 2190959A1
Authority
EP
European Patent Office
Prior art keywords
formula
dicarboxylic acid
use according
group
surfactant
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP08775148A
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English (en)
French (fr)
Inventor
Jean-Emile Zanetto
Suresh Nair
Serkan Mutoy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhodia Operations SAS
Original Assignee
Rhodia Operations SAS
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
Application filed by Rhodia Operations SAS filed Critical Rhodia Operations SAS
Publication of EP2190959A1 publication Critical patent/EP2190959A1/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/266—Esters or carbonates

Definitions

  • the invention relates to the use of carboxylic acid diesters for the treatment of textiles and a formulation for such use.
  • diesters of dicarboxylic acids also called “dibasic esters”, “Dibasic Esters” in English ”
  • the acid of which is linear, in particular the mixture of succinate, glutarate, and dimethyl adipate.
  • US Pat. No. 4,780,235 describes, for example, the combination of at least one C 1 -C 4 dialkyl ester of an aliphatic dibasic acid with 1 to 80% of n-methyl pyrrolidone (NMP), a thickener, and a molecule.
  • activator such as acetic acid, to remove paint from surfaces of rigid objects (stripping).
  • US Pat. No. 5,613,984 discloses a method of cleaning garments soiled with different kinds of paints, comprising the steps of exposing the soiled garment to a dibasic ester, washing the garment with a detergent comprising a surfactant and a solvent, and then dry it.
  • the dibasic ester is in particular a dibasic ester whose acid is linear, such as the mixture of succinate, glutarate, and dimethyl adipate.
  • US Pat. No. 4,673,524 describes a cleaning composition for removing from the surface of the hands hard-to-remove materials, for example paints or coatings. printing inks.
  • This composition comprises a mixture of succinate, glutarate, and dimethyl adipate, combined with an aliphatic hydrocarbon solvent, and an ethoxylated nonylphenol surfactant, or combined with octophenoxypolyethoxyethanol.
  • WO 96/30453 discloses cleaning or stripping compositions for removing hard-to-remove materials, for example rigid surface paints. These compositions comprise a mixture of succinate, glutarate, and dimethyl adipate, combined with an ether such as anisole, optionally with an aliphatic hydrocarbon solvent, and optionally with an ethoxylated nonylphenol surfactant.
  • EP 743 358 discloses compositions for cleaning textiles comprising a mixture of succinate, glutarate, and dimethyl adipate, and an ethoxylated fatty alcohol surfactant.
  • the present invention satisfies this need by proposing the use of a dicarboxylic acid diester for the treatment of textiles, characterized in that the dicarboxylic acid diester corresponds to formula (I):
  • R 1 and R 2 which are identical or different, represent a linear or branched, cyclic or non-cyclic alkyl, aryl, alkylaryl or arylalkyl group, in C 1 -C 20 ,
  • group A represents a divalent alkylene group connected to C 3 -C 10 .
  • dibasic esters mentioned in the context of this invention are part of these families of solvents releasing small amounts of volatile organic compounds, and not presenting a major risk at the HSE level.
  • a diester of a particular dicarboxylic acid of formula (I) is used, the group A of which is connected.
  • This diester of a dicarboxylic acid may be referred to as a "diester”, “diester used in the invention", or "diester plugged”.
  • branched diester may designate a single branched diester corresponding to formula (I) or a mixture or combination of several branched diesters having the formula (I).
  • Group A is a branched divalent alkylene group.
  • the corresponding acid is the compound of formula HOOC-A-COOH.
  • the group A can in particular be a C 3 , C 4 , C 5 , C 6 , C 7 , C 5 or C 9 group , or a mixture. It is preferably a C 4 group .
  • Group A is preferably chosen from the following groups:
  • the groups R 1 and R 2 which may be identical or different, may especially be chosen from methyl, ethyl, n-propyl, isopropyl, benzyl, phenyl, n-butyl, isobutyl, cyclohexyl, hexyl, n-hexyl and isooctyl groups. -éthylhexyle. They correspond to the alcohols of formulas R '-OH and R 2 -OH, which are identical or different.
  • dimethyl of 2-methylglutaric acid can be used, corresponding to the following formula:
  • the dicarboxylic acid diester is in the form of a mixture of different dicarboxylic acid diesters of formula (I).
  • this mixture of branched diesters may comprise the dicarboxylic acid diesters of formulas (Y), (Y ') and optionally (II) as follows:
  • R'-OOC-A ES -COO-R 2 (I "), optionally R'-OOC- (CH 2) 4 -COO-R 2 (II) (diester of adipic acid), where:
  • AMG is a group of formula -CH (CHs) -CH 2 -CH 2 -,
  • AES is a group of formula -CH (C 2 Hs) -CH 2 -.
  • the groups R 1 and R 2 can in particular be methyl, ethyl or isobutyl groups.
  • a mixture of branched diesters comprising: from 70 to 95% by weight of the dicarboxylic acid diester of formula (V), preferably methyl diester,
  • the diester used in the invention can be obtained by any known method leading to diesters, in particular by reaction of an alcohol corresponding to the groups R 1 and R 2 with a dicarboxylic acid corresponding to group A or a di (acyl chloride ) of formula ClOC-A-COCl or a corresponding dinitrile of formula NC-A-CN.
  • a dicarboxylic acid corresponding to group A or a di (acyl chloride ) of formula ClOC-A-COCl or a corresponding dinitrile of formula NC-A-CN a dicarboxylic acid diesters
  • the same type of reaction can be carried out from a corresponding mixture of dicarboxylic acids or acyl chlorides or dinitriles.
  • the diester (s) connected in a mixture can in particular be obtained from a mixture of dinitrile compounds, in particular produced and recovered in the process for the manufacture of adiponitrile by double hydrocyanation of butadiene.
  • This process widely used in industry to produce the vast majority of adiponitrile consumed worldwide, is described in numerous patents and publications.
  • the hydrocyanation reaction of butadiene leads mainly to the formation of linear dinitriles but also to a formation of branched dinitriles, the two main ones are methylglutaronitrile and ethylsuccinonitrile.
  • the branched dinitrile compounds are separated by distillation and recovered, for example, as a top fraction in a distillation column.
  • the mixture of branched dinitrile compounds is converted into diesters to thereby obtain a new solvent.
  • One of the possible processes for converting the dinitrile compounds into diesters corresponds to the implementation of the PINNER reaction, in particular described in French Patent No. 1,488,857. Briefly, this process consists in reacting the dinitrile compounds with an alcohol presence of a strong mineral acid such as sulfuric acid, and then hydrolyzing the products obtained to recover the diesters by distillation.
  • This document also describes a particular embodiment of the process which consists in passing the mixture of dinitrile compounds and the alcohol in a bath of molten salts based on different alkali and ammonium sulphates in order to avoid the formation of ammonium sulphate and to recover ammonia by steam extraction.
  • the diesters used in the invention can also be obtained by a reaction between the dinitrile compounds, water and an alcohol in the gas phase and in the presence of a solid catalyst.
  • the reaction temperature is advantageously greater than the condensation temperature of the diesters formed.
  • an acidic solid catalyst such as, for example, a silica gel, a silica-alumina mixture or boric or phosphoric acids which are supported.
  • macroporous aluminas such as those described in European Patent EP 0 805 801.
  • the reaction temperature is between 200 and 450 ° C., preferably between 230 and 350 ° C.
  • the reaction can be carried out under any pressure, advantageously between 0.1 and 20 bar. At the outlet of the reactor, the vapors are rapidly cooled to a temperature of less than or equal to 150 ° C. From the mixture obtained, ammonia is distilled off, followed by excess water and alcohol.
  • the diesters of the invention can also be obtained by reaction between the dinitrile compounds and a mineral base to obtain acid salts, then neutralization of these salts with an acid followed by esterification with an alcohol.
  • diesters can be purified according to the purification methods conventionally used in the technical field of the preparation of organic compounds and in particular by distillation in one or more columns.
  • the mixture may comprise other compounds than the diester of the invention. It may in particular comprise by-products of an esterification reaction, and / or products derived from byproducts of a prior reaction.
  • the connected diester can be used pure, without any other additives.
  • the plugged diester can be combined, in a liquid formulation, with at least one surfactant, preferably a nonionic surfactant.
  • the surfactant is different from a polyalkoxylated terpene nonionic surfactant.
  • the surfactant may be a customary surfactant, as exemplified in McCutcheon's Emulsifiers & Detergents, North American & International Edition, 2004 Annuals.
  • the surfactant is a polyalkoxylated terpene nonionic surfactant.
  • said polyalkoxylated terpene nonionic surfactant is a polyethoxylated and / or polypropoxylated terpene, preferably polyethoxylated and polypropoxylated, the ethoxy and propoxy units being distributed in random form or in sequential form.
  • said polyalkoxylated terpene nonionic surfactant has the following formula (III):
  • X represents -CH2-C (R3) (R4) -O- or -O-CH (R'3) -CH (R'4) -O- in which:
  • R 5 R 5 R 'and R' identical or different, represent hydrogen or a hydrocarbon radical, saturated or unsaturated, linear, branched or cyclic, C 1 -C 22 "preferably C 1 -C 6;
  • R5 and R6 which may be identical or different, represent hydrogen or a hydrocarbon radical, saturated or unsaturated, linear, branched or cyclic, in Cj-C22 > with the proviso that at least one of the radicals R 5 OR R 6 is different hydrogen;
  • R7 represents hydrogen, a hydrocarbon radical, saturated or unsaturated, linear, branched or cyclic, aromatic or non-aromatic, Ci-C22 > optionally substituted for example by an OH group; n, p, q and are integers or not, greater than or equal to 0, n + p + q> 1, preferably from 2 to 200, preferably from 5 to 50. Preferably, n, p and q are chosen so that:
  • - n is an integer or not, between 2 and 10 inclusive;
  • p is an integer or not between 3 and 20 inclusive;
  • q is an integer or not between 0 and 30 inclusive.
  • a first type of compound is defined by the formula (III) wherein X is equal to
  • the radical Z is chosen from the radicals of formulas c) to g). It should be noted that the radical Z is more particularly attached to the rest of the chain via any one of the carbon atoms 1 to 6, the carbon atoms 1, 5 and 6 being preferred.
  • radical Z may be substituted on at least one of its carbon atoms by two C 1 -C 6 alkyl radicals, preferably two methyl radicals.
  • the carbon 7 is substituted by these two alkyl radicals, more precisely two methyls.
  • One of the preferred compounds used in the present invention therefore consists of a compound whose radical Z corresponds to one of those appearing in FIG. C) to g), and more preferably, the radicals d) and e ); the radical Z being substituted by two methyl radicals, located on carbon 7.
  • radical Z corresponds to formulas d) or e), attached to the rest of the chain by carbon 5 or 1, and bearing two methyl substituents on carbon 7.
  • R3, R4 5 identical or different, represent hydrogen or a methyl radical.
  • R3, R4, represent a hydrogen atom.
  • radicals R5 and R6 which are identical or different, represent hydrogen or a hydrocarbon radical, saturated or non-saturated, linear, branched or cyclic C 1 -C 22 provided that at least one of R 5 OR R 6 is different from hydrogen.
  • said radicals represent hydrogen or a C1-C6 alkyl radical, preferably the methyl radical or the ethyl radical, with the proviso that at least one of these two radicals is different from hydrogen.
  • one of the radicals represents hydrogen and the other a methyl radical.
  • R7 represents hydrogen, a hydrocarbon radical, saturated or unsaturated, linear, branched or cyclic, aromatic or otherwise, optionally substituted for example by an OH group, Ci-C22-
  • R 7 is a hydrocarbon radical
  • the latter is more particularly a C 1 -C 6 alkyl radical, or an alkylphenyl radical, optionally substituted by a halogen (such as chlorine for example).
  • R7 is a hydrogen atom.
  • n 3.
  • p is more particularly between 6.2 and 7, inclusive.
  • p is between 6.3 and 7, inclusive.
  • n is between 4 and 5, terminals included.
  • the value of p is preferably between 7 inclusive and 10 excluded, preferably between 8 inclusive and 10 excluded.
  • q is equal to 0. If q is other than 0, then q is preferably between 5 and 25 inclusive.
  • a second type of compound is defined by the formula (III) in which X represents
  • radical Z corresponds to radical c), the bicyclic compound having no double bond.
  • radical Z is more particularly attached to the rest of the chain via any of the carbon 1 to 6.
  • the carbon atoms 1, 3, 4 or 6 are more particularly retained .
  • radical Z may be substituted on at least one of its carbon atoms by two C1-C ⁇ alkyl radicals, preferably two methyl radicals.
  • the carbon 7 is substituted by these two alkyl radicals, more precisely two methyls.
  • the radical Z bears on one of the carbon atoms 2 or 5, a C 1 -C 4 alkyl substituent, preferably a methyl radical.
  • radicals R'3 and R'4 identical or different, represent hydrogen or a hydrocarbon radical, saturated or unsaturated, linear, branched or cyclic Ci-C22> with the proviso that one of them is different from hydrogen.
  • said radicals represent hydrogen or a C 1 -C 20 alkyl radical, preferably the methyl radical.
  • the compounds of formula (III) can be prepared by reacting:
  • the reaction may further be carried out in the presence of a catalyst.
  • Suitable catalysts include strong bases such as alkali metal, alkaline earth metal or quaternary ammonium hydroxides of the following type:
  • R which may be identical or different, represent hydrogen or a C 1 -C 6 alkyl radical, preferably methyl or ethyl.
  • the hydroxides of sodium, potassium and tetramethylammonium are suitable for carrying out this reaction.
  • catalysts chosen from alkali metal or alkaline earth metal alkoxides, for example sodium or potassium methylate, ethylate or tertiobutylate. It should be noted that it is also possible to use, as a catalyst, primary, secondary or tertiary amines, preferably aliphatic amines, these amines may include other functions such as ether functions. Examples of catalyst of this type include N 5 N- dimethyllaurylamine.
  • the amount is more particularly between 0.5 and 40 mg, based on the weight of the final product. It is conceivable to carry out this reaction in the presence of an acid of
  • Lewis such as BF3 (gaseous or in solution in an ether), SnCl4, SbCl3.
  • the amount of acid catalyst varies more particularly between 0.1 and 10 mmol per mole of reagent (IVa) or (IVb).
  • the contacting is carried out at a temperature sufficient to allow the completion of the reaction.
  • the temperature is greater than 100 0 C, more particularly between 120 and 25O 0 C, and preferably between 150 and 200 0 C.
  • the reaction is carried out under an inert atmosphere under the reaction conditions, such as nitrogen, or a rare gas such as argon or carbon monoxide. Nitrogen is preferred.
  • the reaction can be carried out under atmospheric pressure, under reduced pressure or slight suppression. Usually, it is preferred to work under a pressure of between 1 and 4 bar.
  • the preparation of reagents (IVa) and (IVb) has been described in WO 96/01245, to which reference may be made.
  • the amounts of the compounds (Vop) and (Voe) are calculated according to the characteristics of the formula (III), more particularly the desired values of n and p. These two compounds are introduced successively, so as to obtain a compound of formula (III) sequence.
  • the reaction mixture is preferably neutralized in order to obtain a pH of between 5 and 8, preferably 6 and 7.
  • the neutralization is made by means of acetic acid, or dihydroxide, carbonate or sodium bicarbonate, depending on the nature of the catalyst involved in the reaction.
  • the compound (III) is such that the radical R.7 is hydrogen.
  • the present invention relates to the use of branched diesters for the treatment of textiles, for example polyester fiber textiles. More particularly, said textile treatment may include cleaning to remove soil on said textile.
  • said stain is a one-component or two-component paint stain, water-based or solvent-based, resin, vegetable-based or mineral-based lubricant, products derived from bitumens and petroleum, mud, greasy material, food residues, etc., especially on a polyester fiber fabric.
  • the soil may be fresh or older.
  • the connected diester is effective regardless of the type of paint to be cleaned such as epoxy paints, polyurethanes, acrylics, alkyds, glycerophthalic, etc.
  • the invention also relates to a liquid formulation, intended to be used in particular for the treatment of textiles, and comprising at least one dicarboxylic acid diester having the formula (I) as defined above, and a surfactant, preferably a nonionic surfactant.
  • the formulation comprises a surfactant which is different from a polyalkoxylated terpene nonionic surfactant.
  • the surfactant may be a conventional surfactant, for example an anionic, nonionic (non-terpene), amphoteric, zwitterionic and / or cationic surfactant, for example given in McCutcheon's Emulsifiers & Detergents, North American & International Edition, 2004 Annuals. .
  • the amount of surfactant preferably of nonionic surfactant, preferably of the polyalkoxylated terpene type, preferably the surfactant corresponding to formula (III), is advantageously between 0.1% and 10%, preferably between 0.1%. and 5%, preferably between 0.5 and 4%, and more preferably between 0.5 and 3%, preferably between 0.5% and 2% or even between 0.5% and 1%, by weight, for example by weight as such or by weight of active material, relative to the total amount of the formulation, preferably relative to the total amount of diester type dicarboxylic acid compounds present in said liquid formulation.
  • the formulation of the invention is surprisingly effective even at low levels of surfactant.
  • the formulation is substantially free of other nonionic surfactants, preferably other surfactants in general.
  • the formulation comprises, as surfactant, a polyalkoxylated terpene nonionic surfactant.
  • said polyalkoxylated terpene nonionic surfactant is a polyethoxylated and / or polypropoxylated terpene, preferably polyethoxylated and polypropoxylated, the ethoxy and propoxy units being distributed in random form or in sequential form.
  • the nonionic surfactant is a polyalkoxylated terpene corresponding to the formula (III) as defined above.
  • the liquid formulation may comprise both a polyalkoxylated terpene nonionic surfactant and another surfactant other than a polyalkoxylated terpene nonionic surfactant, such as the usual surfactants mentioned above.
  • the liquid formulation used may also comprise: a. an antioxidant, b. a corrosion inhibitor, c. a thickening agent, d. a dye, e. a perfume, f. a stabilizer, or g. any combination of the above items.
  • the dicarboxylic acid diester corresponding to formula (I) is not diluted in water and / or other organic solvent.
  • the formulation according to the invention does not comprise abrasive agents.
  • the connected diester alone, as a mixture, or combined with additives in the form of a liquid formulation may be applied to the textile to be treated by any appropriate means.
  • the textile is immersed in the plugged diester or the formulation for the time required, for example 1 hour, at room temperature or in a formulation heated to a temperature of between 30 ° C. and 80 ° C., for example 60 ° C.
  • the textile is rinsed once or several times in tap water and then dried in ambient air or in an oven.
  • the textile can undergo, after the washing step in the formulation of the present invention, a second "conventional" washing, ie using a usual washing, before final rinsing with water.
  • the M mixture of dinitrile compounds is composed of:
  • the 100% complement corresponds to the impurities present in this mixture, which are generally not dinitrile compounds.
  • the mixture of dinitrile / methanol compounds is cooled to approximately 10 ° C. before the addition of 84.22 g of 98% by weight sulfuric acid.
  • the reaction medium is heated to reflux and maintained at this temperature for
  • reaction mass is heterogeneous and fluid. After cooling to 60 ° C., 63 g of water are added. The reaction medium is maintained at 65 ° C. for 2 hours.
  • reaction medium becomes biphasic. After removal of the excess methanol by evaporation, the two phases are decanted and analyzed. The recovered organic phase is washed with a saturated aqueous solution of sodium chloride with addition of ammonia to obtain a pH in the region of 7.
  • a second wash is performed with a saturated aqueous solution of sodium chloride.
  • Painted polyester coveralls have been stained with paint for about a month.
  • the stains correspond to the different types of applied paint layers, namely an adhesion primer, a "basecoat” (paint and metallic pigments), and a “clearcoat” (resin without transparent pigment, acting as a protective layer) .
  • the evaluation of the performances of the formulations is carried out using a tergotometer: it is the miniature reproduction of the washing machines of the USA, consisting of 6 stainless steel pots on which pulsed stirrers are fitted with variable stirring. The pots are placed in a thermostatically controlled tank of water.
  • the washing conditions are as follows:
  • an alkaline lye 0.36% of an alkaline lye of 45% +/- 2% of active ingredient comprising 1/3 of NaOH or KOH in pellet, 1/3 of metasilicate or silicate of Na and 1/3 of diphosphate of tetra potassium) + 3% polyalkoxylated terpene surfactant
  • the branched diester obtained according to the synthesis described above is used, combined with 3% by weight of an ethoxylated / propoxylated terpene surfactant Rhodoclean® MSC, marketed by Rhodia.
  • results in Table V show, firstly, that the use of a connected diester associated with a surfactant for cleaning paints on fabrics makes it possible to obtain higher performances than those obtained with a conventional detergent or a non-connected diester. , also associated with a surfactant.
  • results in Table V show that the combination of a branched diester with an ethoxylated-propoxylated terpenic derivative surfactant of formula (III) makes it possible to considerably increase the cleaning performance compared with the connected diester used. alone.
EP08775148A 2007-07-20 2008-07-16 Verwendung von carbonsäurediestern zur behandlung von textilien und formulierung dafür Withdrawn EP2190959A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0756630A FR2918993B1 (fr) 2007-07-20 2007-07-20 Utilisation de diesters d'acide carboxylique pour le traitement de textiles et formulation.
PCT/EP2008/059328 WO2009013207A1 (fr) 2007-07-20 2008-07-16 Utilisation de diesters d'acide carboxylique pour le traitement de textiles et formulation

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EP2190959A1 true EP2190959A1 (de) 2010-06-02

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US (1) US7863232B2 (de)
EP (1) EP2190959A1 (de)
JP (1) JP5232860B2 (de)
CN (1) CN101765654B (de)
BR (1) BRPI0812677A2 (de)
FR (1) FR2918993B1 (de)
WO (1) WO2009013207A1 (de)

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WO2009013207A1 (fr) 2009-01-29
JP5232860B2 (ja) 2013-07-10
US20100240567A1 (en) 2010-09-23
CN101765654B (zh) 2012-05-02
CN101765654A (zh) 2010-06-30
FR2918993B1 (fr) 2012-12-14
FR2918993A1 (fr) 2009-01-23
US7863232B2 (en) 2011-01-04
BRPI0812677A2 (pt) 2014-12-23
JP2010533803A (ja) 2010-10-28

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