EP0513656A1 - Verfahren zum Färben von mit Silanen modifizierten Fasermaterialien, die Modifizierung von Fasermaterialien mit Silanen - Google Patents

Verfahren zum Färben von mit Silanen modifizierten Fasermaterialien, die Modifizierung von Fasermaterialien mit Silanen Download PDF

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Publication number
EP0513656A1
EP0513656A1 EP92107668A EP92107668A EP0513656A1 EP 0513656 A1 EP0513656 A1 EP 0513656A1 EP 92107668 A EP92107668 A EP 92107668A EP 92107668 A EP92107668 A EP 92107668A EP 0513656 A1 EP0513656 A1 EP 0513656A1
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EP
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Prior art keywords
carbon atoms
alkoxy
substituted
group
general formula
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.)
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EP92107668A
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German (de)
English (en)
French (fr)
Inventor
Andreas Dr. Schrell
Werner Hubert Dr. Russ
Thomas Riehm
Tilo Dr. Vaahs
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Hoechst AG
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Hoechst AG
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Priority claimed from DE19924210270 external-priority patent/DE4210270A1/de
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0513656A1 publication Critical patent/EP0513656A1/de
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/503—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms without bond between a carbon atom and a metal or a boron, silicon, selenium or tellurium atom
    • D06M13/507—Organic silicon compounds without carbon-silicon bond
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
    • D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
    • D06P1/5292—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds containing Si-atoms
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/927—Polyacrylonitrile fiber
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/93—Pretreatment before dyeing

Definitions

  • alkaline agents are particularly necessary to fix the technically important reactive dyes on the fiber.
  • a dyeing process that is low in salt or completely without salt and at the same time only under The use of small amounts of an alkaline agent or can be carried out entirely without such an alkaline auxiliary is therefore particularly advantageous in the dyeing process using fiber-reactive dyes. Because in addition to the fixing process of the fiber-reactive dye in the aqueous, often strongly alkaline dye liquor, hydrolysis reactions of the fiber-reactive dye can also take place, which is why the fixing on the fiber material is not complete.
  • the alkyl and alkoxy substituents are preferably those of 1 to 8 carbon atoms.
  • the use of this fiber material modified with such a silane compound makes it possible to carry out the dyeing process (which also includes printing processes) using low-electrolyte and low-alkali or even electrolyte-free and alkali-free dyeing liquors, which means that the time-consuming post-treatment of the dyeings by rinsing and boiling processes can also be omitted.
  • the present invention therefore relates to a process for dyeing (including printing) textile fiber materials with water-soluble dyes, in particular anionic dyes, which is characterized in that the dyeing is carried out using low-electrolyte or completely electrolyte-free and / or low-alkali or completely alkali-free dye liquors (including printing pastes ) is carried out and a fiber material modified with an abovementioned silane compound is used as the textile material.
  • Fiber materials which are modified according to the invention and can be used according to the invention in dyeing processes are all the synthetic and natural fiber materials mentioned above and modified with such silanes.
  • the present invention therefore also relates to textile fiber materials modified with such silanes.
  • R5 is preferably hydrogen, alkyl of 1 to 3 carbon atoms, such as methyl and ethyl, or cyclohexyl and particularly preferably hydrogen, methyl or ethyl, especially hydrogen.
  • R6 is preferably hydrogen, alkyl of 1 to 4 carbon atoms, in particular methyl and ethyl, phenyl or alkyl of 2 to 4 carbon atoms, which is substituted by methoxy or ethoxy, of which less preferably hydrogen.
  • the group of the formula (4a) preferably represents a secondary amino group, such as in particular the methylamino or ethylamino group.
  • silane compounds which can be used according to the invention are, for example, polymeric silane compounds, such as siloxanes and polyethyleneimines, which are substituted by at least one silane radical, such as, for example, polyethyleneimines composed of 2 to 5 ethyleneimine units, of which 1 to 3 amino groups are represented by a radical of the general formula (7) in which G, R1, R8 and R9 one of the above, particularly preferred, Have meanings which are substituted, G being preferably a radical of the general formulas (6a) to (6f), (6i) and (6j).
  • Polymeric siloxanes are those which are derived from disiloxane or from those having 3 to 5 silicon atoms, the silicon atoms being substituted by the radicals R1, R2 and R9, the radical R2 preferably being bonded to the terminal silicon atoms.
  • alkyl, alkenyl and alkylene radicals mentioned for the above formula radicals can be straight-chain or branched. Within the scope of their given meaning, the individual formula residues can have meanings which are the same or different from one another.
  • Hydrolysable substituents bonded to the silicon atom are, for example, hydrogen atoms, halogen atoms, alkoxy, phenoxy, amino and amide radicals, such as, for example, those which are initially mentioned for the formula radical R 1. Of these, alkoxy radicals are preferred.
  • the present invention also relates to these new silane compounds of the general formula (8), their preparation and, as already stated at the beginning, their use for modifying fiber material.
  • the starting compounds of the general formulas (12a) and (12b) are prepared in a conventional manner by starting from the corresponding hydroxy compound (amino alcohol) and using the metallic alkali metal, such as sodium and especially potassium, in a manner known per se in the implements solvents mentioned above.
  • the reaction takes place at a temperature between 50 and 150 ° C., preferably between 80 and 110 ° C. It is advantageous to choose a solvent with a sufficiently high boiling point so that the alkali metal can be heated above its melting point in order to simplify and accelerate the reaction.
  • Solvents suitable for this purpose are, in particular, aliphatic hydrocarbons with a boiling range from 70 to 150 ° C., such as, for example, heptane and dodecane, and mixtures thereof, furthermore aromatic hydrocarbons, such as, for example, alkyl-substituted benzenes and naphthalenes, such as, in particular, toluene and xylene, and furthermore aliphatic, in particular cycloaliphatic Ether compounds such as tetrahydrofuran.
  • aliphatic hydrocarbons with a boiling range from 70 to 150 ° C. such as, for example, heptane and dodecane, and mixtures thereof
  • aromatic hydrocarbons such as, for example, alkyl-substituted benzenes and naphthalenes, such as, in particular, toluene and xylene
  • aliphatic, in particular cycloaliphatic Ether compounds such as t
  • the compound of the general formula (8) is reacted according to the invention with a compound of the general formula (12a) or (12b), the corresponding alkali metal halide is liberated and precipitates out as a crystalline salt. It is separated off after the reaction, for example by filtration, and the solvent is removed from the batch freed from this by means of fractional distillation and the synthesized silane compound is obtained.
  • silane compounds which can be used according to the invention are: [ ⁇ - ( ⁇ '-aminoethoxy) propyl] trimethoxysilane, [ ⁇ - ( ⁇ '-aminoethylamino) propyl] trimethoxysilane, [ ⁇ - ⁇ '-aminoethoxy) propyl] methyl -diethoxysilane, [ ⁇ - ( ⁇ '-aminoethylamino) propyl] methyldimethoxysilane, 3- or 4-aminophenyltrimethoxysilane, [ ⁇ - (4-aminophenoxy) propyl] trimethoxy -silane, N- [ ⁇ - (trimethoxysilyl) propyl] -N, N-di- ( ⁇ '-aminoethyl) amine, ( ⁇ -aminopropyl) trimethoxysilane, ( ⁇ -aminopropyl) ethoxy- dimethyl silane, ( ⁇ -amin
  • the modification of the textile fiber material takes place according to the invention in such a way that the textile fiber material is preferably mixed with an aqueous solution of the silane compound which contains the silane in a concentration between 0.1 and 20% by weight contains between 5 and 10% by weight.
  • This silane solution can be applied to the textile fiber material by treatment in the aqueous dye liquor itself (analogous to a dye-drawing process) or by padding or spraying. If the fiber material is impregnated with the silane solution by introducing the material into this solution or by padding (padding), the impregnated material is then squeezed off from excess liquor, so that the liquor absorption is between 50 and 120% by weight, preferably between 70 and 100 wt .-%, based on the weight of the fiber material.
  • the impregnation is carried out at a temperature between 10 and 60 ° C, preferably at a temperature between 15 and 30 ° C. If the aqueous silane solution is applied to the fiber material by spraying, the liquid absorption is generally chosen between 10 and 50% by weight.
  • the fiber material impregnated with the silane solution is then dried, the drying usually being carried out simultaneously with the fixing of the silane compound on the fiber material. Drying and fixing are preferably carried out at elevated temperature, for example at a temperature between 100 and 230 ° C., preferably between 100 and 150 ° C. and in particular between 110 and 135 ° C., this treatment by hot air for 2 to 5 minutes or by saturated steam can be done.
  • the fixation can also be done by simply drying the suspended, impregnated material in drying cabinets.
  • the fixing in such a way that the impregnated material is initially packed in a moist state, if appropriate in an airtight manner, at room temperature (15 to 25 ° C.) or slightly elevated temperature (up to 40 ° C.) stored for 24 hours and then carried out the fixation at high temperature as indicated above.
  • the textile fiber material that is modified according to the invention as well as in The modified form used in the dyeing process according to the invention can be present in all processing states, such as yarn, flake, sliver and piece goods (fabric), as well as in the form of mixed fiber materials, such as cotton / polyester fiber materials, such as mixed fabrics.
  • the dyeing of textile fiber materials modified in this way takes place analogously to the known dyeing methods and printing processes for dyeing or printing fiber materials with water-soluble textile dyes, such as anionic dyes, in particular fiber-reactive dyes, and using the temperature ranges and customary amounts of dye known for this purpose, but with the amount of dye according to the invention Exception that for the dye baths, padding liquors and printing pastes of the dyeing process according to the invention, an addition of alkaline compounds, such as are usually used for fixing fiber-reactive dyes, such as sodium carbonate, potassium carbonate, sodium hydroxide solution and water glass, can be largely or completely excluded and furthermore the usual addition of electrolyte salts, which in particular should increase the migration of the dye on the fiber, or not only in geri Narrow dimensions, i.e. up to a maximum of 10 g per liter of dye bath or dye liquor is required.
  • the dyeing process according to the invention is accordingly carried out within a pH range between 4 and 8, preferably between 4.5 and 7, and in particular
  • Dyeing processes which can be used according to the invention are, for example, the various exhaust processes, such as dyeing on the jigger and on the reel runner or dyeing from a long or short liquor, dyeing in jet dyeing machines, dyeing using the pad-cold-dwell method or after a block hot steam fixing process. With the pull-out process you can work in the usual liquor ratio of 1: 3 to 1:20.
  • the dyeing temperature can be between 30 and 90 ° C, preferably it is at a temperature below 60 ° C; As can be seen from the above-mentioned application of the pad-cold residence method according to the invention, dyeing is also advantageous at room temperature (10 to 30 ° C) possible.
  • the customary auxiliaries such as surfactants (wetting agents), urea, thiourea, thiodiethylene glycol, thickeners and leveling aids or auxiliaries which improve the solubility of dyes in the concentrated padding liquors, such as, for example, condensation products from formaldehyde and optionally alkyl-substituted naphthalenesulfonic acids, can be used.
  • surfactants wetting agents
  • urea thiourea
  • thiodiethylene glycol thickeners
  • leveling aids or auxiliaries which improve the solubility of dyes in the concentrated padding liquors
  • auxiliaries which improve the solubility of dyes in the concentrated padding liquors, such as, for example, condensation products from formaldehyde and optionally alkyl-substituted naphthalenesulfonic acids.
  • All water-soluble, preferably anionic dyes which preferably have one or more sulfo and / or carboxy groups and which can optionally contain fiber-reactive groups, are suitable for the dyeing methods according to the invention.
  • fiber-reactive dyes they can belong to the class of azo development dyes, direct dyes, vat dyes and acid dyes, which include, for example, azo dyes, copper complex, cobalt complex and chromium complex azo dyes, copper and nickel phthalocyanine dyes, anthraquinone and copper formazan - And triphendioxazine dyes.
  • azo development dyes direct dyes
  • vat dyes and acid dyes which include, for example, azo dyes, copper complex, cobalt complex and chromium complex azo dyes, copper and nickel phthalocyanine dyes, anthraquinone and copper formazan - And triphendioxazine dyes.
  • azo dyes copper complex, cobalt complex and
  • Fiber-reactive dyes are organic dyes which contain 1, 2, 3 or 4 fiber-reactive radicals from the aliphatic, aromatic or heterocyclic series. Such dyes have been widely described in the literature.
  • the dyes can belong to a wide variety of dye classes, such as the class of monoazo, disazo, polyazo, metal complex azo, such as 1: 1 copper, 1: 2 chromium and 1: 2 cobalt complex monoazo.
  • Fiber-reactive radicals are to be understood here as those which bind to the hydroxyl groups of cellulose, the amino, carboxy, hydroxyl and thiol groups of wool and silk or to the amino and possibly carboxy groups of synthetic polyamides to form a covalent chemical bond able to react.
  • the fiber-reactive residues can be bound to the dye residue directly or via a bridge member; it is preferably directly or via an optionally monoalkylated amino group, such as, for example, a group of the formula -NH-, -N (CH3) -, -N (C2H5) - or -N (C3H7) -, or via an aliphatic radical, such as one Methylene, ethylene or propylene radical or an alkylene radical of 2 to 8 carbon atoms, which can be interrupted by one or two oxy and / or amino groups, or via a bridge member containing an amino group, such as a phenylamino group, to the Dye residue bound.
  • an optionally monoalkylated amino group such as, for example, a group of the formula -NH-, -N (CH3) -, -N (C2H5) - or -N (C3H7) -, or via an aliphatic radical, such as one Methylene, ethylene or propylene
  • Particularly interesting fiber-reactive radicals are fluorine and chloro-1,3,5-triazine radicals of the formula (13) in which Hal is chlorine or fluorine and Q is an amino, alkylamino, N, N-dialkylamino, cycloalkylamino, N, N-dicycloalkylamino, aralkylamino, arylamino, N-alkyl-N-cyclohexylamino, N- Alkyl-N-arylamino group or an amino group which contains a heterocyclic radical which may have a further fused-on carbocyclic ring, or amino groups in which the amino nitrogen atom is a member of an N-heterocyclic ring which optionally contains further heteroatoms, as well as hydrazino and semicarbazido groups , wherein said alkyl radicals can be straight-chain or branched and low molecular weight and higher molecular weight, preferably those with 1 to 6 carbon atoms.
  • Suitable cycloalkyl, aralkyl and aryl radicals are, in particular, cyclohexyl, benzyl, phenethyl, phenyl and naphthyl radicals; Heterocyclic residues are especially furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole and benzoxazole residues.
  • amino groups in which the amino nitrogen atom is a member of an N-heterocyclic Ring is, preferably residues of six-membered N-heterocyclic compounds into consideration, which may contain nitrogen, oxygen or sulfur as further heteroatoms.
  • alkyl, cycloalkyl, aralkyl and aryl radicals, the heterocyclic radicals and the N-heterocyclic rings can additionally be substituted, for example by halogen, such as fluorine, chlorine and bromine, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C1 -C4-alkyl, C1-C4-alkoxy, acylamino groups such as acetylamino or benzoylamino, ureido, hydroxy, carboxy, sulfomethyl or sulfo.
  • halogen such as fluorine, chlorine and bromine
  • sulfamoyl carbamoyl, C1 -C4-alkyl, C1-C4-alkoxy
  • acylamino groups such as acetylamino or benzoylamino, ureido
  • amino groups are: -NH2, methylamino, ethylamino, propylamino, isopropylamino, butylamino, hexylamino, ⁇ -methoxyethylamino, ⁇ -methoxypropylamino, ⁇ -ethoxyethylamino, N, N-dimethylamino, N, N-diethylamino, ⁇ -chloroethylamino , ⁇ -cyanoethylamino, ⁇ -cyanopropylamino, ⁇ -carboxyethylamino, sulfomethylamino, ⁇ -sulfoethylamino, ⁇ -hydroxyethylamino, N, N-di- ⁇ -hydroxyethylamino, ⁇ -hydroxypropylamino, benzylamino, phenethylamino, cyclohexylamino, phenyla
  • Q can be an amino radical of the general formula -NR20R21, in which R20 is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl or ethyl, and R21 is phenyl which is obtained through a fiber-reactive radical of the vinylsulfone series directly or via a methylamino , Ethylamino, methylene, ethylene or propylene group is substituted and which can also be substituted by 1 or 2 substituents from the group methoxy, ethoxy, methyl, ethyl, chlorine, carboxy and sulfo, or R21 alkyl of 2 to 4 C- Atoms is such as ethyl or n-propyl which is substituted by a fiber reactive group of the vinyl sulfone series, or alkylene phenyl with an alkylene radical of 1 to 4 carbon atoms, the phenyl of which is substituted by a fiber-reactive radical of the vinylsulfone series, or
  • Fiber-reactive groups of the vinyl sulfone series are those of the general formula -SO2-Y, in which Y is vinyl or ethyl which is substituted in the ⁇ -position by an alkali-eliminable substituent, such as, for example, chlorine, sulfato, phosphato, thiosulfato, acetyloxy, sulfobenzoyloxy and dimethylamino.
  • an alkali-eliminable substituent such as, for example, chlorine, sulfato, phosphato, thiosulfato, acetyloxy, sulfobenzoyloxy and dimethylamino.
  • the dyeings of the modified cellulose fiber materials obtainable in the manner according to the invention do not require any further aftertreatment after removal from the dyebath or after the dye has been fixed on the substrate, in particular no complicated aftertreatment process including washing. As a rule, it is sufficient to rinse the colored substrate once or several times with warm or hot and, if appropriate, cold water, if appropriate using a nonionic wetting agent. A final boiling treatment of the dyed substrate with a washing solution to improve the fastness properties is not necessary.
  • these polymeric ethers correspond to a general formula in which s is a number from 1 to 4.
  • Example A To prepare a silane compound according to the invention, the procedure of Example A is followed, but the equivalent amount of ⁇ -chloropropyl-triethoxy-silane is used instead of the ⁇ -chloropropyl-methyl-diethoxy-silane compound.
  • the [ ⁇ - ( ⁇ '-N-methylaminoethoxy) propyl] triethoxysilane of the formula according to the invention is obtained by fractional distillation at a boiling range between 104 and 118 ° C at 5 ⁇ 10 ⁇ 2 mbar.
  • Example A To prepare a silane compound according to the invention, the procedure of Example A is followed, but instead of the ⁇ -chloropropyl-methyl-diethoxy-silane compound, the equivalent amount of ( ⁇ -chloropropyl) - (dimethyl) - (ethoxy) -silane is used a.
  • the compound of the invention [ ⁇ - ( ⁇ '-N-methylaminoethoxy) propyl] - (dimethyl) - (ethoxy) silane of the formula is obtained by fractional distillation at a boiling range between 90 and 105 ° C at 5 ⁇ 10 ⁇ 2 mbar.
  • N-methylaminoethanol 36.7 parts are slowly added to 20.1 parts of potassium in 700 parts by volume of tetrahydrofuran, the exothermic reaction being kept at a temperature between 30 and 40 ° C. by external cooling.
  • the mixture is then heated under reflux until the potassium has reacted completely (about 5 hours) and then 147.7 parts of a mixture (in a ratio of the meta / para isomers of about 70: at a temperature between 20 and 35 ° C. are added: 30) of [3'- and 4'-chloromethyl-phenyl-1- and -2-ethyl] -methyl-diethoxysilane.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
EP92107668A 1991-05-11 1992-05-06 Verfahren zum Färben von mit Silanen modifizierten Fasermaterialien, die Modifizierung von Fasermaterialien mit Silanen Withdrawn EP0513656A1 (de)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
DE4115461 1991-05-11
DE4115461 1991-05-11
DE4208212 1992-03-14
DE4208212 1992-03-14
DE4210270 1992-03-28
DE4210271 1992-03-28
DE4210271 1992-03-28
DE19924210270 DE4210270A1 (de) 1992-03-28 1992-03-28 Aminogruppenhaltige Silanverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Veredlung von Fasermaterial

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EP0513656A1 true EP0513656A1 (de) 1992-11-19

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EP92107668A Withdrawn EP0513656A1 (de) 1991-05-11 1992-05-06 Verfahren zum Färben von mit Silanen modifizierten Fasermaterialien, die Modifizierung von Fasermaterialien mit Silanen

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US (1) US5403361A (enrdf_load_stackoverflow)
EP (1) EP0513656A1 (enrdf_load_stackoverflow)
JP (1) JPH05171577A (enrdf_load_stackoverflow)
KR (1) KR920021799A (enrdf_load_stackoverflow)
CA (1) CA2068267A1 (enrdf_load_stackoverflow)
MX (1) MX9202174A (enrdf_load_stackoverflow)
TW (1) TW223134B (enrdf_load_stackoverflow)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0590397A1 (de) * 1992-09-26 1994-04-06 Hoechst Aktiengesellschaft Verfahren zur Herstellung von Färbungen gemäss der "Ink-Jet"-Drucktechnik auf modifizierten Fasermaterialien mit anionischen Textilfarbstoffen
EP0692559A1 (de) 1994-06-30 1996-01-17 Hoechst Aktiengesellschaft Mit polymeren Aminverbindungen modifizierte synthetische cellulosische Fasern
EP0692558A1 (de) 1994-06-30 1996-01-17 Hoechst Aktiengesellschaft Verfahren zur Herstellung von aminierten Fasern aus Regeneratcellulose
EP0703305A1 (de) 1994-09-23 1996-03-27 Hoechst Aktiengesellschaft Verfahren zur Herstellung von aminierter Regeneratcellulose
US5512061A (en) * 1993-03-02 1996-04-30 Hoechst Aktiengesellschaft Printing and dyeing of textiles (inverse resist printing)
US5865858A (en) * 1994-01-29 1999-02-02 Hoechst Aktiengesellschaft Aminated cellulosic synthetic fibers
WO2018054687A1 (de) * 2016-09-21 2018-03-29 Henkel Ag & Co. Kgaa Verbesserte färbung von textilien mit synthetischen materialien in der waschmaschine durch modifizierte silikone
WO2020119968A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum behandeln von textilien mit siliciumorganischen verbindungen
WO2020119971A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung, einem silikonpolymer und einer farbgebenden verbindung
WO2020119970A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung und einem reaktivfarbstoff und/oder pigment
WO2020119964A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung, einer farbgebenden verbindung und einem filmbildenden, hydrophoben polymer
WO2020119972A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung, einer farbgebenden verbindung und einem silikonöl
WO2020119969A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung, einer farbgebenden verbindung und einem filmbildenden, hydrophilen polymer
WO2020119973A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung, einem oligoalkylsiloxan und einer farbgebenden verbindung

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CN104452351A (zh) * 2014-11-26 2015-03-25 四川省宜宾惠美线业有限责任公司 改性纤维素纤维
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CN104452353A (zh) * 2014-11-26 2015-03-25 四川省宜宾惠美线业有限责任公司 纤维素纤维经改性剂改性的工艺
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EP0590397A1 (de) * 1992-09-26 1994-04-06 Hoechst Aktiengesellschaft Verfahren zur Herstellung von Färbungen gemäss der "Ink-Jet"-Drucktechnik auf modifizierten Fasermaterialien mit anionischen Textilfarbstoffen
US5348557A (en) * 1992-09-26 1994-09-20 Hoechst Aktiengesellschaft Production of dyeings by the inkjet printing technique on modified fiber materials using anionic textile dyes
US5512061A (en) * 1993-03-02 1996-04-30 Hoechst Aktiengesellschaft Printing and dyeing of textiles (inverse resist printing)
US5865858A (en) * 1994-01-29 1999-02-02 Hoechst Aktiengesellschaft Aminated cellulosic synthetic fibers
EP0692559A1 (de) 1994-06-30 1996-01-17 Hoechst Aktiengesellschaft Mit polymeren Aminverbindungen modifizierte synthetische cellulosische Fasern
EP0692558A1 (de) 1994-06-30 1996-01-17 Hoechst Aktiengesellschaft Verfahren zur Herstellung von aminierten Fasern aus Regeneratcellulose
US5529585A (en) * 1994-06-30 1996-06-25 Hoechst Ag Rayon modified with polymeric amine compounds
EP0703305A1 (de) 1994-09-23 1996-03-27 Hoechst Aktiengesellschaft Verfahren zur Herstellung von aminierter Regeneratcellulose
WO2018054687A1 (de) * 2016-09-21 2018-03-29 Henkel Ag & Co. Kgaa Verbesserte färbung von textilien mit synthetischen materialien in der waschmaschine durch modifizierte silikone
WO2020119968A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum behandeln von textilien mit siliciumorganischen verbindungen
WO2020119971A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung, einem silikonpolymer und einer farbgebenden verbindung
WO2020119970A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung und einem reaktivfarbstoff und/oder pigment
WO2020119964A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung, einer farbgebenden verbindung und einem filmbildenden, hydrophoben polymer
WO2020119972A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung, einer farbgebenden verbindung und einem silikonöl
WO2020119969A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung, einer farbgebenden verbindung und einem filmbildenden, hydrophilen polymer
WO2020119973A1 (de) * 2018-12-13 2020-06-18 Henkel Ag & Co. Kgaa Verfahren zum färben von textilien, umfassend die anwendung von einer siliciumorganischen verbindung, einem oligoalkylsiloxan und einer farbgebenden verbindung

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KR920021799A (ko) 1992-12-18
JPH05171577A (ja) 1993-07-09

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