EP1506336B1 - Formulations d'adoucissants silicones destinees au finissage textile - Google Patents

Formulations d'adoucissants silicones destinees au finissage textile Download PDF

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Publication number
EP1506336B1
EP1506336B1 EP20030749889 EP03749889A EP1506336B1 EP 1506336 B1 EP1506336 B1 EP 1506336B1 EP 20030749889 EP20030749889 EP 20030749889 EP 03749889 A EP03749889 A EP 03749889A EP 1506336 B1 EP1506336 B1 EP 1506336B1
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Prior art keywords
alkyl
mono
chain
sum
independently
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English (en)
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EP1506336A2 (fr
Inventor
Winfried Guth
Rainer Idel
Detlev Kierspe
Friedrich Koch
Peter Landenberger
Helmut-Martin Meier
Horst Lange
Roland Wagner
Jürgen Krott
Annette MÖLLER
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Momentive Performance Materials GmbH
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Momentive Performance Materials GmbH
Momentive Performance Materials Inc
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • E—FIXED CONSTRUCTIONS
    • E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
    • E01B—PERMANENT WAY; PERMANENT-WAY TOOLS; MACHINES FOR MAKING RAILWAYS OF ALL KINDS
    • E01B37/00—Making, maintaining, renewing, or taking-up the ballastway or the track, not provided for in a single one of groups E01B27/00 - E01B35/00
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
    • D06M11/11—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
    • D06M11/155—Halides of elements of Groups 2 or 12 of the Periodic System
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
    • D06M11/11—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
    • D06M11/17—Halides of elements of Groups 3 or 13 of the Periodic System
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
    • D06M11/55—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof with sulfur trioxide; with sulfuric acid or thiosulfuric acid or their salts
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/68—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof
    • D06M11/70—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof with oxides of phosphorus; with hypophosphorous, phosphorous or phosphoric acids or their salts
    • D06M11/71—Salts of phosphoric acids
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives thereof
    • D06M15/05—Cellulose or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
    • E—FIXED CONSTRUCTIONS
    • E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
    • E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
    • E01C19/00—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving
    • E01C19/12—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving for distributing granular or liquid materials
    • E01C19/18—Devices for distributing road-metals mixed with binders, e.g. cement, bitumen, without consolidating or ironing effect
    • E01C19/185—Devices for distributing road-metals mixed with binders, e.g. cement, bitumen, without consolidating or ironing effect for both depositing and spreading-out or striking-off the deposited mixture
    • E—FIXED CONSTRUCTIONS
    • E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
    • E01B—PERMANENT WAY; PERMANENT-WAY TOOLS; MACHINES FOR MAKING RAILWAYS OF ALL KINDS
    • E01B21/00—Track superstructure adapted for tramways in paved streets
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31652—Of asbestos
    • Y10T428/31663—As siloxane, silicone or silane

Definitions

  • the invention relates to novel formulations based on quaternized aminoalkyl silicones or siloxanes, processes for the preparation of these formulations and their use as textile auxiliaries for finishing textile materials.
  • Silicone softeners are widely used for finishing textile materials. Requirements such as storage stability, temperature stability, resistance to whiteners and other anionic textile auxiliaries, resistance to changes in pH and salt addition and against the action of mechanical energy are of central importance for the practical use of the silicone softener emulsions. In particular, the stability against the action of mechanical energy, the shear stability or jet stability, often causes great difficulties for silicone softener emulsions under practical conditions (see R. Zyschka, Melliand Textilberichte 6/2001, 497).
  • Microemulsions basically offer the advantage of thermodynamic stability.
  • the equilibrium phase behavior has been treated depending on the structure of the oil to be emulsified and the surfactant (s).
  • the addition of inorganic salts has also been studied systematically (cf. M. Kahlweit et al., Langmuir 11 [1995], 3382 ; M. Kahlweit et al., Langmuir 11 [1995 ]).
  • the equilibrium phase behavior of microemulsions of low molecular weight silicones has also been investigated ( EP-A 774482 ; H. von Berlepsch et al., Progr. Colloid Polymer Science 111 [1998], 107 ).
  • aminoalkylsiloxane oils are increasingly being replaced by polyether-modified aminoalkylsiloxane oils (cf. EP-A 578144 ).
  • Finely divided microemulsions of aminoalkylsiloxanes are to be accessible in a two-stage process by preparing a concentrate of aminoalkylsiloxane, silicone-insoluble surfactant and a small amount of water, followed by rapid stirring in water ( US-A 4620878 ).
  • aminosiloxane emulsions are to be mechanically stable by the use of water-soluble nonionic emulsifiers.
  • water-soluble nonionic emulsifiers For extreme shear loads, as achieved on modern jet plants, it was found that the in DE-A 3723697 disclosed inventions are not sufficient to prevent precipitation in the jet equipment and on the textiles to be treated.
  • WO 02/10501 should amino-functional organosilicon compounds without using water-soluble nonionic emulsifiers in jet dyeing machines mechanically stable. It was found that the in WO 02/10501 also be insufficient to reliably prevent precipitation on differently pretreated textiles.
  • salts of strong acids for example Al 2 (SO 4 ) 3 ⁇ 18 H 2 O, secure the protonation of cationic dyes in thermal transfer printing pastes, but at the same time impair their stability (cf. US-A 5925701 ).
  • Preferred hydrophilic, non-ionic surface-active compounds (a) are substances which lower the surface tension of water below 45 mN / m.
  • These are ethylene / propylene oxide (EO / PO) modified compounds, optionally unsaturated and / or branched, from the group of fatty alcohols, fatty acids, alcohols, acids, alkylaryl derivatives, fatty amines, glycerides and sorbitan esters in which the number of EO / PO Is between 15 and 150, with the ratio of PO units to EO units being 0.25 or less than 0.25, and where the number of ethylene oxide (EO) units is greater than or equal to the number of carbon atoms in the non-electronic EO is part, and to alkyl polyglycosides, ethylene oxide / propylene oxide copolymers and polyether siloxanes.
  • EO / PO ethylene / propylene oxide
  • formulations according to the invention which contain, as compound (a), the ester of stearic acid and 40 mol of EO.
  • the formulations according to the invention contain at least one nitrogen-quaternized aminoalkylsiloxane compound (silicone quat).
  • Such compounds and their preparation are known, for example from WO 02/10 256 . WO 02/10257 . WO 02/10 259 .
  • DE-A 100 36 522 and DE-A 102 12 470
  • the formulations according to the invention also comprise any desired mixtures of the abovementioned quaternized aminoalkylsiloxane compounds with the corresponding nonquaternized compounds.
  • these non-quaternized compounds in the formula (10), in each case, one of the radicals R 11 or R 12 or R 13 or R 14 is missing from the nitrogen atoms in the main chain
  • inventively preferred quaternized aminoalkylsiloxane compounds are the subject of WO 02/10 259 and there described in general and specific.
  • the addition of the described additives a) can be done in two ways. It is possible, on the one hand, for the additives according to the invention to be introduced directly into the formulations. On the other hand, it may be preferred under practical conditions to first dilute the formulations to application concentration and then to add the additives according to the invention to the prepared liquor.
  • the formulations according to the invention may contain, in addition to the components (a), further surface-active components (f) which permit emulsification or microemulsification.
  • components (f) are customary formulation agents known to the person skilled in the art for the preparation of the silicone (micro) emulsions, which however are not stable against high energy input alone.
  • Preferred such components are f1) to f6): (f1) oxalkylation products obtainable by alkoxylation with ethylene oxide or propylene oxide of condensation products of phenolic OH group-containing aromatics with formaldehyde and NH-functional groups.
  • nonionic or ionically modified compounds from the group of the alkoxylates, alkylolamides, esters, amine oxides and alkyl polyglycosides, in particular reaction products of alkylene oxides with alkylatable compounds, such as fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols, carboxylic acid amides and resin acids.
  • ethylene oxide from the class of reaction products of ethylene oxide with saturated and / or unsaturated fatty alcohols having 6 to 25 carbon atoms (commercially available, for example in the form of Renex® Produlct Zoo) or alkylphenols having 4 to 12 carbon atoms in the alkyl radical or saturated and / or unsaturated fatty amines having 14 to 20 carbon atoms or saturated and / or unsaturated fatty acids having 14 to 22 carbon atoms or esterification and / or arylation products prepared from natural or modified, optionally hydrogenated castor oil, optionally by esterification with Dicarboxylic acids are linked to recurring structural units.
  • ionic or nonionic compounds from the group of the reaction products of alkylene oxide with sorbitan ester [Tween, ICI], alkoxylated acetylenediols and glycol, alkoxylated phenols, in particular phenol / styrene-polyglycol ethers.
  • ionic or nonionic polymeric surfactants from the group of homopolymers and copolymers, graft copolymers and graft copolymers, and also random and linear block copolymers.
  • anionic surfactants such as alkyl sulfates, ether sulfates, ether carboxylates, phosphate esters, sulfosuccinate amides, paraffin sulfonates, olefin sulfonates, sarcosinates, isothionates and taurates f6) amphoteric surfactants such as betaines and ampholytes, especially glycinates, propionates and imidazolines.
  • Particularly preferred formulation components (f) are alkoxylated fatty alcohols, branched fatty alcohols and fatty acids having 4 to 14 alkoxy units, very particularly preferred formulation components (f) are alkoxylated fatty alcohols, branched fatty alcohols having 6 to 12 alkoxy units, especially formulations containing the ether of tridecyl alcohol with 12 mol EO containing tridecyl alcohol ether with 6 moles of EO.
  • the formulation ingredients are generally added in conventional amounts of the formulation of the invention.
  • the components (f) are preferably added in amounts of 1 to 200% by weight, preferably 10 to 80% by weight, particularly preferably 10 to 50% by weight, based on the quaternized aminoalkylsiloxane.
  • the formulations may also contain further auxiliaries in the amounts customary for these auxiliaries.
  • Usual aids within the meaning of the invention include leveling agents, wetting agents, gloss finishes, fiber-protecting agents, slip-resistance agents and other auxiliaries according to the prior art.
  • leveling agents wetting agents, gloss finishes, fiber-protecting agents, slip-resistance agents and other auxiliaries according to the prior art.
  • buffer systems can be incorporated to set an optimum pH during the equipment.
  • the quaternized aminoalkylsiloxane compounds can be mixed with the components (a), if appropriate with the addition of further abovementioned constituents, preferably in the temperature range from 20 to 90.degree. C., more preferably from 25 to 70.degree more preferably at 30 to 60 ° C.
  • the quaternized aminoalkylsiloxanes are preferably added to the compound (a); the quaternized aminoalkylsiloxane (silicone quat) is particularly preferably initially introduced, and the emulsion formation is completed by addition of the compound (a) and optionally further additives.
  • the formulations according to the invention are outstandingly suitable as fabric softeners in the finishing of textile fabrics, in particular those of cotton, keratin fibers, preferably wool, silk or synthetic fibers or For example, very good for the equipment of textile fabrics made of blends of cotton with polyester, polyamide, polyacrylonitrile, wool or silk. Excellent results are equally obtained in the finishing of textile fabrics of synthetic fibers, in particular of polyester, polyamide, polypropylene or mixtures thereof
  • Textile fabrics are preferably understood to mean woven fabrics, knitted fabrics, knitted fabrics and nonwovens.
  • the equipment is generally carried out by the continuous process (pad-type or lisseuse process) or by the exhaustion process (jet process).
  • the formulations according to the invention by one of these finishing processes, it has proven to be advantageous to comply with the following technological parameters:
  • Formulation 1 Formulation 2
  • Formulation 3 Formulation 3
  • 430g SQ 430g SQ 430g SQ 258g Renex® 36 125g Renex® 36 125g Renex® 36 44.5g Renex® 30
  • 44.5g Renex® 30 44.5g Renex® 30 10g of acetic acid 10g of acetic acid 10g of acetic acid 7.5g sodium acetate 7.5g sodium acetate 7.5g sodium acetate 245g dist. water 245g dist. water 245g dist. water 79.5g 2-propanol 79.5g 2-propanol 87.5g Crodet S40 59g Crodet® S40
  • Experiment 1 describes the unacceptable result of a non-inventive experiment according to the prior art. A doubling of the amount of surfactant of both Renex types does not lead to a prevention of precipitation (Experiment 2, not according to the invention).
  • Experiment 3 shows that by incorporating hydrophilic surface-active compounds directly into the formulation according to the invention precipitation is reliably prevented. This also applies to a partial subsequent addition according to the invention (Experiment 4) or complete addition according to the invention (Experiment 5) to this hydrophilic surface-active compound.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Architecture (AREA)
  • Civil Engineering (AREA)
  • Structural Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)

Claims (15)

  1. Formulations contenant au moins un aminoalkylsiloxane quaternisé et au moins un composé constitué de la série
    a) des composés tensioactifs hydrophiles non ionogènes,
    caractérisées en ce que les composés tensioactifs hydrophiles non ionogènes (a) sont des composés modifiés avec de l'oxyde d'éthylène/de l'oxyde de propylène (EO/PO), le cas échéant insaturés et/ou ramifiés, choisis dans le groupe des alcools gras, des acides gras, des alcools, des acides, des dérivés d'alkylaryle, des amines grasses, des glycérides et des esters de sorbitane contenant entre 15 et 150 unités d'EO/PO, le rapport EO /PO étant égal ou inférieur à 0,25 et le nombre d'unités d'oxyde d'éthylène (partie EO) étant supérieur ou égal au nombre d'atomes de carbone contenus dans la partie non-EO, et en ce qu'ils sont des alkylpolyglycosides, des copolymères d'oxyde d'éthylène/d'oxyde de propylène et des polyéthersiloxanes,
    et caractérisées, de plus, pour l'aminoalkylsiloxane quaternisé, en ce qu'il s'agit de polymères de polysiloxane linéaires ou cycliques contenant des unités structurales répétitives des formules (10) et (11)
    Figure imgb0132
    Figure imgb0133
     dans lesquelles
    X désigne un radical hydrocarboné divalent ayant au moins 4 atomes de carbone, qui peut présenter un groupement hydroxyle et qui, de préférence, en présente un et qui peut être interrompu par un atome d'oxygène, et où les groupements X contenus dans les unités répétitives peuvent être identiques ou différents.
    Y désigne un radical hydrocarboné divalent ayant au moins 2 atomes de carbone, qui peut présenter un groupement hydroxyle et qui peut être interrompu par un ou plusieurs atomes d'oxygène ou d'azote,
    R11, R12, R13 et R14 sont identiques ou différents et désignent des radicaux alkyle ayant 1 à 4 atomes de carbone ou des radicaux benzyle, ou les radicaux R1 et R3 ou R2 et R4 peuvent être respectivement parmi les composants d'un radical alkylène capable de former des ponts,
    R16 désigne l'hydrogène (H) ou un radical alkyle ayant 1 à 20 atomes de carbone, qui peut être substitué par l'oxygène,
    M désigne la structure -B-O-(EOx)v(POx)w-B-, dans laquelle
    EOx est une unité oxyde d'éthylène et POx est une unité oxyde de propylène,
    B désigne un alkylène en C2 à C6 linéaire ou ramifié,
    v valant 0 à 200,
    w valant 0 à 200,
    v + w valant ≥ 1,
    n valant 2 à 1000, les valeurs n des unités répétitives pouvant être identiques ou différentes,
    A- désigne un anion inorganique ou organique.
  2. Formulations selon la revendication 1, caractérisées en ce que le composé (a) est un composé correspondant aux formules (1) à (9) suivantes :

            R1-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E     (1),

    Figure imgb0134

            R2-NH-[CH2CH(CH3)O]r-[CH2CH2O]q-E     (3),

    Figure imgb0135
    Figure imgb0136
    Figure imgb0137

            R2-NH-CH(CH3)CH2-[OCH2CH(CH3)]m-[OCH2CH2]q-O-E     (6),

            R2-NH-CH(CH3)CH2-[OCH2CH(CH3)]m7-[OCH2CH2]q-[OCH2CH(CH3)]m8-NH-R2     (7),

            E-O-[CH2CH2O]3-[CH2CH(CH3)O]1-E     (8),

    ou
    Figure imgb0138
     dans lesquelles
    E désigne un radical R1, l'hydrogène, un alkyle en C1-C18 linéaire ou ramifié, saturé ou mono- ou polyinsaturé, qui est substitué, le cas échéant, une ou plusieurs fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, ou désigne un cycloalkyle en C5-C10, qui est substitué, le cas échéant, une ou plusieurs fois par un groupement alkyle en C1-C4, -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle,
    R1 désigne un alkyle en C8-C40 linéaire ou ramifié, saturé ou insaturé, dont la chaîne alkyle est interrompue, le cas échéant, une ou plusieurs fois par des atomes d'oxygène et/ou d'azote et qui est substitué, le cas échéant, une ou plusieurs fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, amino, mono- ou di(alkyl en C1-C4)amino, ou désigne un cycloalkyle en C5-C10, dont la chaîne alkyle est interrompue, le cas échéant, une ou plusieurs fois par des atomes d'oxygène et/ou d'azote et qui est substitué, le cas échéant, une ou plusieurs fois par un groupement alkyle en C1-C4, -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, amino, mono- ou di(alkyle en C1-C4)amino,
    R2 désigne un alkyle en C8-C40 linéaire ou ramifié, saturé ou mono- ou polyinsaturé, qui est substitué, le cas échéant, une ou plusieurs fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle,
    R3 désigne un alkyle en C1-C26 linéaire ou ramifié ou un aryle en C6-C10,
    R4 désigne R3 ou un radical correspondant aux formules suivantes :

            -CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E ,

            -CH2CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E

            -CH2CH2CH2-O-CH2CHOHCH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E

            -Z-[CH2CH2O]q-[CH2CH(CH3)O]r-E

    dans lesquelles
    Z est un radical alkyle ou cycloalkyle linéaire ou ramifié, qui peut être interrompu, respectivement, par un groupe -O- et/ou -CO- et substitué, le cas échéant, par au moins un groupement OH,
    ou aux formules :
    Figure imgb0139
     q valant 15 à 150,
    q1 et q2 valant, indépendamment l'un de l'autre, 0 à 150,
    la somme de q1 + q2 = q,
    q3, q4, q5 et q6 valant, indépendamment l'un de l'autre, 0 à 150,
    la somme de q3 + q4 + q5 + q6 = q,
    r valant 0 à 50,
    r1 et r2 valant, indépendamment l'un de l'autre, 0 à 50,
    la somme de r1 + r2 = r,
    r3, r4, r5 et r6 valant, indépendamment l'un de l'autre, 0 à 50,
    la somme de r3 + r4 + r5 + r6 = r et
    le rapport r:q étant ≤ 0,25,
    m valant 1 à 50,
    m7 et m8 valant, indépendamment l'un de l'autre, 1 à 50,
    où 2 ≤ m7 + m8 et la somme de m7 + m8 = m + 1, et
    le rapport q:m étant ≥ 4,
    s valant 5 à 150,
    t valant 5 à 150,
    où 0,05 ≤ s:t ≤ 20,
    0≤ z1 ≤ 2000,
    0 ≤ z2 ≤ 2000,
    au moins un radical R4 ≠ R3, et
    0,01 ≤ ∑ radicaux alkyle R3:∑ q + r ≤ 1
  3. Formulations selon la revendication 2, dans lesquelles
    E désigne l'hydrogène, un alkyle en C1-C4 linéaire ou ramifié, saturé ou mono- ou polyinsaturé, qui est substitué, le cas échéant, 1 à deux fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, ou désigne un cycloalkyle en C5-C6, qui est substitué le cas échéant, une à plusieurs fois par un groupement alkyle en C1-C4, -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle,
    R1 désigne un alkyle en C10-C36 linéaire ou ramifié, saturé ou mono- ou polyinsaturé, dont la chaîne alkyle est interrompue, le cas échéant, une ou plusieurs fois par des atomes d'oxygène et/ou d'azote et qui est substitué, le cas échéant, une ou plusieurs fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, amino, mono- ou di(alkyle en C1-C4)amino, ou désigne un cycloalkyle en C5-C6, dont la chaîne alkyle est interrompue, le cas échéant, une ou plusieurs fois par des atomes d'oxygène et/ou d'azote et qui est substitué, le cas échéant, une ou plusieurs fois par un groupement alkyle en C1-C4, -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, amino, mono- ou di(alkyle en C1-C4)amino.
    R2 désigne un alkyle en C10-C36 linéaire ou ramifié, saturé ou mono- ou polyinsaturé, qui est substitué, le cas échéant, une ou plusieurs fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle,
    R3 désigne un alkyle en C1-C18 linéaire ou ramifié ou un aryle en C6-C10,
    R4 désigne un radical R3 ou un radical correspondant aux formules suivantes :

            -CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E ,

    ou

            -CH2CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E

    q valant 20 à 100,
    q1 et q2 valant, indépendamment l'un de l'autre, 20 à 100,
    la somme de q1 + q2 = q,
    q3, q4, q5 et q6 valant, indépendamment l'un de l'autre, 20 à 100,
    la somme de q3 + q4 + q5 + q6 = q,
    r valant 0 à 20,
    r1 et r2 valant, indépendamment l'un de l'autre, 0 à 20,
    la somme de r1 + r2 = r,
    r3, r4, r5 et r6 valant, indépendamment l'un de l'autre, 0 à 20,
    la somme de r3 + r4 + r5 + r6 = r, et
    le rapport r:q étant ≤ 0,25,
    m valant 1 à 7,
    m7 et m8 valant, indépendamment l'un de l'autre, à 1 à 7,
    où 2 ≤ m7 + m8 et la somme de m7 + m8 = m, et
    le rapport q:m est ≥ 4,
    s valant 5 à 100,
    t valant 5 à 100,
    où 0,05 ≤ s:t ≤ 20,
    0 ≤ z1 ≤ 2000,
    0 ≤ z2 ≤ 2000,
    au moins un radical R4 ≠ R3, et
    0,01 ≤ ∑ radicaux alkyle R3:∑ q + r ≤ 0,5.
  4. Formulations selon au moins l'une quelconque des revendications 1 à 3, caractérisées en ce que le composé (a) est un composé correspondant aux formules (1') à (9') suivantes :
    Figure imgb0140
    Figure imgb0141
    Figure imgb0142
    Figure imgb0143
    Figure imgb0144
    Figure imgb0145
    Figure imgb0146
    Figure imgb0147
     ou un polyéther siloxane (9') :
    Figure imgb0148
     dans lesquelles
    les expressions mises entre parenthèses "{" et "}" qui figurent dans les formules (1') à (8') signifient que les unités d'oxyde d'éthylène ou d'oxyde de propylène se trouvant au sein de ces expressions mises entre parenthèses peuvent être disposées en séquences (voir figure ci-dessus) ou de manière aléatoire.
    E désigne un radical R1, de l'hydrogène, un alkyle en C1-C18 linéaire ou ramifié, saturé ou mono- ou polyinsaturé, qui est substitué, le cas échéant, une ou plusieurs fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, ou désigne un cycloalkyle en C5-C10, qui est substitué, le cas échéant, une ou plusieurs fois par un groupement alkyle en C1-C4, -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle,
    R1 désigne un alkyle en C8-C40 linéaire ou ramifié, saturé ou insaturé, dont la chaîne alkyle est interrompue, le cas échéant, une ou plusieurs fois par des atomes d'oxygène et/ou d'azote et qui est substitué, le cas échéant, une ou plusieurs fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, amino, mono- ou di(alkyle en C1-C4)amino, ou désigne un cycloalkyle en C5-C10, dont la chaîne alkyle est interrompue, le cas échéant, une ou plusieurs fois par des atomes d'oxygène et/ou d'azote et qui est substitué, le cas échéant, une ou plusieurs fois par un groupement alkyle en C1-C4, -OH, alcoxy en C1-C4 , alcoxycarbonyle en C1-C4 ou carbonyle, amino, mono- ou di(alkyle en C1-C4)amino, ou désigne un aryle en C6-C10, qui est substitué, le cas échéant, et en particulier par un alkyle en C3-C15,
    R2 désigne un alkyle en C8-C40 linéaire ou ramifié, saturé ou mono- ou polyinsaturé, qui est substitué, le cas échéant, une ou plusieurs fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle,
    R3 désigne un alkyle en C1-C26 ou un aryle en C6-C10, linéaire ou ramifiés.
    R4 désigne R3 ou un radical correspondant aux formules suivantes :
    Figure imgb0149
    Figure imgb0150
    Figure imgb0151
    Figure imgb0152
     Z est un radical alkyle ou cycloalkyle, linéaire ou ramifié, qui peut être interrompu respectivement par -O- et/ou -CO- et substitué, le cas échéant, par au moins un groupement OH,
    ou désigne
    Figure imgb0153
     q valant 15 à 150,
    q1 et q2 valant, indépendamment l'un de l'autre, 0 à 150,
    la somme de q1 + q2 = q,
    q3, q4, q5 et q6 valant, indépendamment l'un de l'autre, à 0 à 150,
    la somme de q3 + q4 + q5 + q6 = q,
    r valant 0 à 50,
    r1 et r2 valant, indépendamment l'un de l'autre, 0 à 50,
    la somme de r1 + r2 = r,
    r3, r4, r5 et r6 valant, indépendamment l'un de l'autre, 0 à 50,
    la somme de r3 + r4 + r5 + r6 = r, et
    le rapport r:q étant ≤ 0,25,
    m valant 1 à 50,
    m7 et m8 valant, indépendamment l'un de l'autre, à 1 à 50,
    où 2 ≤ m7 + m8, et
    le rapport q:m étant ≥ 4,
    s valant 5 à 150, de préférence 15 à 150,
    t valant 0 à 150, de préférence 5 à 150 et en particulier 5 à 20,
    où t:s ≤ 0,25
    0 ≤ z1 ≤ 2000
    0 ≤ z2 ≤ 2000
    au moins un radical R4 ≠ R3, et
    pour la formule (9') s'applique la relation suivante: 0 , 01 ≤ Σ radicaux alkyle R 3 : Σ q ≤ 1.
    Figure imgb0154
  5. Formulations selon la revendication 4, dans lesquelles
    E désigne de l'hydrogène, un alkyle en C1-C4 linéaire ou ramifié, saturé ou mono- ou polyinsaturé, qui est substitué, le cas échéant, 1 à deux fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, ou désigne un cycloalkyle en C5-C6, qui est substitué, le cas échéant, une à plusieurs fois par un groupement alkyle en C1-C4, -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle,
    R1 désigne un alkyle en C10-C36 linéaire ou ramifié, saturé ou insaturé, dont la chaîne alkyle est interrompue, le cas échéant, une ou plusieurs fois par des atomes d'oxygène et/ou d'azote et qui est substitué, le cas échéant, une ou plusieurs fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, amino, mono- ou di(alkyl C1-C4)amino, ou désigne un cycloalkyle en C5-C6, dont la chaîne alkyle est interrompue, le cas échéant, une ou plusieurs fois par des atomes d'oxygène et/ou d'azote et qui est substitué, le cas échéant, une ou plusieurs fois par un groupement alkyle en C1-C4, -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle, amino, mono- ou di(alkylC1-C4)amino, ou désigne un aryle en C6-C10, qui est substitué, le cas échéant, en particulier par un alkyle en C3-C15,
    R2 désigne un alkyle en C10-C36 linéaire ou ramifié, saturé ou mono- ou polyinsaturé, qui est substitué, le cas échéant, une ou plusieurs fois par un groupement -OH, alcoxy en C1-C4, alcoxycarbonyle en C1-C4 ou carbonyle,
    R3 désigne un alkyle en C1-C18 ou un aryle en C6-C10, linéaires ou ramifiés,
    R4 désigne un radical R3 ou un radical correspondant aux formules suivantes :
    Figure imgb0155
     ou
    Figure imgb0156
     q valant 20 à 100,
    q1 et q2 valant, indépendamment l'un de l'autre, 20 à 100,
    la somme de q1 + q2 = q,
    q3, q4, q5 et q6 valant, indépendamment l'un de l'autre, 20 à 100,
    la somme de q3 + q4 + q5 + q6 = q,
    r valant 0 à 20,
    r1 et r2 valant, indépendamment l'un de l'autre, 0 à 20,
    la somme de r1 + r2 = r,
    r3, r4, r5 et r6 valant, indépendamment l'un de l'autre, 0 à 20,
    la somme de r3 + r4 + r5 + r6 étant égale à r, et
    le rapport r:q étant ≤ 0,25,
    m valant 1 à 7,
    m7 et m8 valant, indépendamment l'un de l'autre, 1 à 7,
    où 2 ≤ m7 + m8, et
    le rapport q:m étant ≥ 4,
    s valant 5 à 100, de préférence 15 à 100,
    t valant 5 à 100, de préférence 5 à 20,
    où t:s ≤ 0,25
    0 ≤ z1 ≤ 2000
    0 ≤ z2 ≤ 2000
    au moins un radical R4 ≠ R3,
    et
    pour la formule (9'), s'applique la relation suivante :
    0 , 01 ≤ Σ radicaux alkyle R 3 : Σ q ≤ 0 , 5.
    Figure imgb0157
  6. Formulations selon au moins l'une quelconque des revendications 2 à 3, dans lesquelles

            E désigne H, CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-,

            CH3CH2CH2CH2- ou CH3C(O)-

    R1 désigne un radical correspondant aux formules suivantes :

            CH3(CH2)n1-

    Figure imgb0158
    Figure imgb0159
    Figure imgb0160
    Figure imgb0161

            CH3(CH2)7CH=CH(CH2)8-

    dans lesquelles
    n1 = 9 à 23,
    n2 = 3 à 23,
    n3 = 0 à 18,
    n4=7à23,
    n5 = 3 à 15,
    R2 désigne un radical correspond aux formules suivantes :
    Figure imgb0162
    Figure imgb0163
    Figure imgb0164
     dans lesquelles
    n6 = 8 à 28,
    R3 désigne un alkyle en C1-C18 ou un aryle en C6-C10,
    R4 désigne un radical R3 ou un radical correspondant aux formules:

            -CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E,

    ou

            -CH2CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E q valant 25 à 60,

    q1 et q2 valant, indépendamment l'un de l'autre, 25 à 60,
    la somme de q1 + q2 = q,
    q3, q4, q5 et q6 valant, indépendamment l'un de l'autre, à 25 à 60,
    la somme de q3 + q4 + q5 + q6 = q,
    r valant 0 à 10,
    r1 et r2 valant, indépendamment l'un de l'autre, 0 à 10,
    la somme de r1 + r2 = r,
    r3, r4, r5 et r6 valant, indépendamment l'un de l'autre, à 0 à 10,
    la somme de r3 + r4 + r5 + r6 = r, et
    le rapport r:q étant ≤ 0,25, et
    pour la formule (9) s'applique la relation suivante : 0 , 01 ≤ Σ radicaux alkyle R 3 : Σ q + r ≤ 0 , 1.
    Figure imgb0165
  7. Formulations selon au moins l'une quelconque des revendications 4 et 5, dans lesquelles

            E désigne H, CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-,

            CH3CH2CH2CH2- ou CH3C(O)-

    R1 désigne un radical correspondant aux formules suivantes :

            CH3(CH2)n1-

    Figure imgb0166
    Figure imgb0167
    Figure imgb0168
    Figure imgb0169

            CH3(CH2)7CH=CH(CH2)8-

    dans lesquelles
    n1 = 9 à 23,
    n2 = 3 à 23, de préférence 6 à 23
    n3 = 0 à 18, et, de préférence, n2 + n3 ≤ 31, n4=7à23,
    n5 = 3 à 15,
    R2 désigne un radical correspondant aux formules suivantes :
    Figure imgb0170
    Figure imgb0171
    Figure imgb0172
     dans lesquelles
    n6 = 8 à 28,
    R3 désigne un alkyle en C1-C18 ou un aryle en C6-C10,
    R4 désigne un radical R3 ou un radical correspondant aux formules :
    Figure imgb0173
     ou
    Figure imgb0174
     q valant 25 à 60,
    q1 et q2 valant, indépendamment l'un de l'autre, 25 à 60,
    la somme de q1 + q2 = q,
    q3, q4, q5 et q6 valant, indépendamment l'un de l'autre, 25 à 60,
    la somme de q3 + q4 + q5 + q6 = q,
    r valant 0 à 10,
    r1 et r2 valant, indépendamment l'un de l'autre, 0 à 10,
    la somme de r1+ r2 = r,
    r3, r4, r5 et r6 valant, indépendamment l'un de l'autre, à 0 à 10,
    la somme de r3 + r4 + r5 + r6 = r, et
    le rapport r:q étant ≤ 0,25, et
    pour la formule (9') s'applique la relation suivante : 0 , 01 ≤ Σ radicaux alkyle R 3 : Σ q ≤ 0 , 1.
    Figure imgb0175
  8. Formulations selon au moins l'une quelconque des revendications 1 à 7, caractérisées en ce qu'elles contiennent, comme composé (a), de l'ester d'acide stéarique et 40 mol EO.
  9. Formulations selon au moins l'une quelconque des revendications 1 à 8, caractérisées en ce que le rapport quantitatif (Ω) de la quantité de composés tensioactifs hydrophiles non ionogènes (a) aux quantités de composés d'aminoalkylsiloxane quaternisé est de Ω = 0,05 à 10.
  10. Utilisation des formulations selon au moins l'une quelconque des revendications 1 à 9 comme assouplissant de textiles lors de l'apprêt de structures textiles selon le procédé en continu ou par épuisement de bain.
  11. Utilisation selon la revendication 10, pour l'apprêt de structures textiles en coton, en fibres de kératine, de préférence, en laine, en soie, en fibres synthétiques ou dans des mélanges composés des types précités.
  12. Utilisation selon la revendication 10, pour l'apprêt de structures textiles constituées de mélanges de coton avec du polyester, du polyamide, du polyacrylonitrile, de la laine ou de la soie.
  13. Utilisation selon la revendication 10, pour l'apprêt de structures textiles en polyester, en polyamide, en polypropylène ou dans des mélanges des ceux-ci.
  14. Utilisation selon au moins l'une quelconque des revendications 11 à 12, caractérisée en ce que, pour l'apprêt des structures textiles en coton ou dans des mélanges de coton avec du polyester, du polyamide, du polyacrylonitrile, de la laine ou de la soie, prétraitées avec des agents de blanchiment anioniques, on emploie une machine de teinture à jet.
  15. Procédé de fabrication des formulations selon au moins l'une quelconque des revendications 1 à 14, caractérisé en ce que l'on mélange au moins un aminoalkylsiloxane quaternisé, tel qu'il est défini selon la revendication 1, à au moins un composé tensioactif hydrophile non ionogène, tel qu'il est défini selon la revendication 1,
    et, le cas échéant, à d'autres agents auxiliaires et/ou adjuvants dans une plage de température de 20 à 90 °C de préférence.
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US20060100396A1 (en) 2006-05-11
KR101032177B1 (ko) 2011-05-02
EP1506336A2 (fr) 2005-02-16
US7718268B2 (en) 2010-05-18
KR20040111607A (ko) 2004-12-31
AU2003232759A8 (en) 2003-11-11
DE10221521A1 (de) 2003-12-04
WO2003095735A3 (fr) 2004-04-08
JP4381299B2 (ja) 2009-12-09
CN1665981A (zh) 2005-09-07
JP2005533934A (ja) 2005-11-10
CN100368467C (zh) 2008-02-13
ATE508222T1 (de) 2011-05-15
DE50313668D1 (de) 2011-06-16
MXPA04011207A (es) 2005-02-14
WO2003095735A2 (fr) 2003-11-20
AU2003232759A1 (en) 2003-11-11

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