EP0075770A2 - Textile treating composition and its use in finishing textile materials - Google Patents
Textile treating composition and its use in finishing textile materials Download PDFInfo
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- EP0075770A2 EP0075770A2 EP82108390A EP82108390A EP0075770A2 EP 0075770 A2 EP0075770 A2 EP 0075770A2 EP 82108390 A EP82108390 A EP 82108390A EP 82108390 A EP82108390 A EP 82108390A EP 0075770 A2 EP0075770 A2 EP 0075770A2
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Classifications
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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
- 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
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
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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
- 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
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/192—Polycarboxylic acids; Anhydrides, halides or salts 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
- 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
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/368—Hydroxyalkylamines; Derivatives thereof, e.g. Kritchevsky bases
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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
- 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
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
Definitions
- acylated alkanolamines which, for example, in K. Lindner's "Tenside-Textile Aid Wash Raw Materials", 2nd Edition, Volume 1, pp. 904 and 993, and in Schwartz-Perry "Surface Active Agents” 1949, Vol. 1, P. 173, contain amide and / or ester groups, depending on the alkanolamines used.
- Carboxylic acids of natural or synthetic origin are used in their production, e.g. Lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid or their mixtures, e.g. be made from coconut oil, palm kernel oil or tallow, or branched chain acids from oxosynthesis, e.g. Isostearic acid, or its acid chlorides use.
- Lauric acid and behenic acid are preferably used in the form of their technical qualities.
- Suitable amines containing hydroxyl groups include monoethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N- (2-aminoethyl) -ethanolamine, 1-aminopropanol and bis- (2-hydroxypropyl) amine.
- N- (2-Aminoethyl) ethanolamine, monoethanolamine and diethanolamine are preferably used.
- Preferred compounds B are reaction products of technical stearic acid or behenic acid with 3-amino-1-dimethylamino-propane or 3-amino-1-diethylamino-propane, which are quaternized with dimethyl sulfate or dimethyl phosphite.
- the quaternization is carried out by conventional methods without a solvent or in a solvent, and in addition to water or ethyl alcohol, the acylated alkanolamines A. can also be used in molten form, provided that they do not contain a tertiary nitrogen atom.
- Suitable quaternizing agents are: methyl chloride, dimethyl sulfate, dimethyl phosphite or ethylene oxide, in which case the reaction is carried out in sulfuric or phosphoric acid solution.
- the substances of the two groups of substances A and B can also be prepared in a one-pot process by reacting mixtures of the amines mentioned for both groups with fatty acids and then quaternizing the proportion of tertiary amino groups.
- Mono- to tetravalent alcohols having 3-20 C atoms, the alkyl chains of which may be interrupted by oxygen, are preferably used to prepare the carboxylic acid esters C.
- Ethylene oxide adducts of fatty acids, fatty alcohols, fatty amines or alkylphenols can optionally be used to improve solubility.
- the optimal degree of oxyethylation differs from case to case and can be from 3-50 moles of ethylene oxide per mole of starting substance.
- aqueous emulsions of Emul Sion polymerization produced dimethylpolysiloxanes with average molecular weights of 1000 to 100,000 can be used.
- compositions according to the invention can also contain other constituents as are customary in textile auxiliaries. These include protective colloids, perfumes, fungicides or bactericides as well as anti-foaming agents.
- the mixtures according to the invention are converted into water-containing preparations.
- the mixtures are heated above the melting point and, with stirring after the appropriate amount of warm water has been added, are stirred homogeneously.
- liquid stable solutions or emulsions are obtained which preferably contain 10-30% by weight of the textile treatment agents according to the invention.
- the mixtures can be applied to the textile material by known methods in the exhaust process (reel runner, nozzle-dyeing unit), by padding or by spraying. It is a particular advantage that the textile treatment agents according to the invention can be applied with nozzle-dyeing units.
- Textile processing processes such as sewing or tufting, place high demands on the textile material with regard to surface smoothness.
- High needle speeds lead to thermal and mechanical stress on the material to be sewn, which is due to a lack of surfaces smoothness can lead to thread breaks and stitch detonation damage.
- This disadvantage can be avoided by providing the textile material with a smoothing finish.
- emulsions or dispersions of paraffinic hydrocarbons or waxes for this purpose.
- German Offenlegungsschriften 26 21 881, 27 33 493, 28 16 196 and 28 30 173 describe cationic emulsions of paraffin hydrocarbons, cationic surfactants serving as emulsifiers.
- DE-OS 30 03 851 describes dispersions of oxidized waxes, while DE-OS 25 35 768 uses dispersions of polysiloxanes and hydrocarbons or fluorine-containing polymers to achieve high surface smoothness. It is also known to use fatty acid esters as lubricants together with paraffin hydrocarbons.
- the agents according to the invention are excellent plasticizers and smoothing agents for textile materials of all kinds.
- Table 1 shows the molar amounts of the components used for the preparation of the acylated alkanolamines A and the acid numbers as they were obtained after the reaction under reduced pressure and elevated temperature.
- Table 2 shows the molar ratio in which the individual components for the production of the basic fatty acid amides or fatty acid esters were used, which serve as starting products for the production of the quaternary ammonium salts.
- the last line shows the acid numbers obtained when the components reacted at elevated temperature and pressure.
- Table 3 gives an overview of the production of the quaternary ammonium salts used.
- the following components are mixed to produce the textile treatment agents according to the invention:
- the figures given are percentages by weight.
- the components are heated to 80 ° C, stirred and made 20% by adding 80 ° C warm water. After homogeneous stirring, the mixtures are cooled to room temperature with stirring. Liquid, cream-colored formations form which can be easily diluted to the concentration intended for use in practice by adding warm water.
- Part of the material was dried at 80 ° C, steamed twice for 10 seconds at 120 ° C and at 23 ° C u. 65% rel. Conditioned moisture.
- Another part of the finished material was steamed twice at 120 ° C for 10 seconds after drying at 80 ° C, then fixed at 170 ° C for a further 20 seconds and then at 23 ° C and 65% rel. Conditioned moisture.
- the fabric sections were then stretched in a stenter under an elongation of 88% and the number of stitch blasting damage over a seam length of 80 cm was determined in the backlight.
- Table 6 shows the determined test data in comparison to an untreated product.
- the product T 2 was used according to the following recipe: cotton interlock, reactive-dyed black.
- Nozzle dyeing apparatus "Surfer”, from ESPA Fleet ratio 1:12 Concentration 4% based on the weight of the goods 20 min at 40 ° C, acetic acid pH 5 After spinning, it was dried at 80-100 ° C and steamed with saturated steam.
Abstract
Textilbehandlungsmittel, die A. 50-80 Gew.-% acylierte Alkanolamine aus gesättigten oder ungesättigten Fettsäuren mit 12-22 C-Atomen und Alkanolaminen die 1 oder 2 Stickstoffatome, 1 - 3 Hydroxylgruppen und 2 - 6 C-Atome enthalten, im Molverhältnis 1:1 bis 3:1, B. 10-30 Gew.-% wasserlösliche, quaternäre Ammoniumsalze der allgemeinen Formel <IMAGE> worin R1 einen Alkyl- oder Alkenylrest mit 14 - 25 C-Atomen, der durch eine Amid- oder Estergruppe unterbrochen ist, R2 einen Rest wie R1 oder einen Alkylrest mit 1-4 C-Atomen, R3 einen Alkylrest mit 1 - 4 C-Atomen, einen Hydroxyethyl- oder Hydroxypropylrest, R4 einen Alkylrest mit 1 - 4 C-Atomen, einen Hydroxyethyl-, Hydroypropyl- oder Benzylrest und X<(-)> ein Anion bedeuten, C. 2-20 Gew.-% Fettsäureester aus gesättigten oder ungesättigten Fettsäuren mit 12-22 C-Atomen oder Dicarbonsäuren mit 4-10 C-Atomen und ein- bis vierwertigen Alkoholen mit 3-20 C-Atomen, D. 0-20 Gew.-% Ethylenoxid-Addukte von Fettsäuren mit 12-22 C-Atomen oder von Fettalkoholen mit 8-18 C-Atomen oder von Alkyl- bzw. Dialkylaminen mit 12-36 C-Atomen oder von Alkylphenolen mit 10-24 C-Atomen mit 3 bis 50 mol Ethylenoxid und E. 0.25 Gew.-% Diorganopolysiloxane mit einer Viskosität von 1000 bis 100 000 cSt. enthalten, sowie Verfahren zum Ausrüsten von natürlichen und synthetischen Textilmaterialien, dadurch gekennzeichnet, daß sie mit diesen Textilbehandlungsmitteln behandelt werden.Textile treatment agents containing A. 50-80% by weight acylated alkanolamines from saturated or unsaturated fatty acids with 12-22 carbon atoms and alkanolamines containing 1 or 2 nitrogen atoms, 1-3 hydroxyl groups and 2-6 carbon atoms, in a molar ratio of 1 : 1 to 3: 1, B. 10-30 wt .-% water-soluble, quaternary ammonium salts of the general formula <IMAGE> in which R1 is an alkyl or alkenyl radical having 14-25 carbon atoms, which is interrupted by an amide or ester group , R2 a radical such as R1 or an alkyl radical with 1-4 C atoms, R3 an alkyl radical with 1-4 C atoms, a hydroxyethyl or hydroxypropyl radical, R4 an alkyl radical with 1-4 C atoms, a hydroxyethyl, hydroypropyl - or benzyl and X <(-)> mean an anion, C. 2-20 wt .-% fatty acid esters from saturated or unsaturated fatty acids with 12-22 C atoms or dicarboxylic acids with 4-10 C atoms and mono- to tetravalent Alcohols with 3-20 C atoms, D. 0-20% by weight ethylene oxide adducts of fatty acids with 12-22 C atoms or of fet talc alcohols with 8-18 C atoms or of alkyl or dialkylamines with 12-36 C atoms or of alkylphenols with 10-24 C atoms with 3 to 50 mol of ethylene oxide and E. 0.25% by weight of diorganopolysiloxanes with a viscosity from 1000 to 100,000 cSt. contain, as well as processes for finishing natural and synthetic textile materials, characterized in that they are treated with these textile treatment agents.
Description
Gegenstand der Erfindung sind Textilbehandlungsmittel, die
- A. 50 - 80 Gew.-% acylierte Alkanolamine aus gesättigten oder ungesättigten Fettsäuren mit 12-22 C-Atomen und Alkanolaminen, die 1 oder 2 Stickstoffatome, 1-3 Hydroxylgruppen und 2-6 C-Atome enthalten, im Molverhältnis 1:1 bis 3:1,
- B. 10 - 30 Gew.-% wasserlösliche quaternäre Ammoniumsalze der allgemeinen Formel:
- R1 einen Alkyl- oder Alkenylrest mit 14-25 C-Atomen, der durch eine Amid- oder Estergruppe unterbrochen ist,
- R2 einen Rest wie R1 oder einen Alkylrest mit 1-4 C-Atomen, R3 einen Alkylrest mit 1-4 C-Atomen, einen Hydroxyethyl- oder Hydroxypropyl-Rest,
- R4 einen Alkylrest mit 1-4 C-Atomen, einen Hydroxyethyl-, Hydroxypropyl- oder Benzylrest und
- X(-) ein Anion bedeuten,
- C. 2 - 20 Gew.-% Fettsäureester aus gesättigten oder ungesättigten Fettsäuren mit 12-22 C-Atomen oder Dicarbonsäuren mit 4 bis 10 C-Atomen und ein- bis vierwertigen Alkoholen mit 3-20 C-Atomen,
- D. 0 - 20 Gew.-% Ethylenoxid-Addukte von Fettsäuren mit 12 - 22 C-Atomen oder von Fettalkoholen mit 8-18 C-Atomen oder von Alkyl- bzw. Dialkylaminen mit 12-36 C-Atomen oder von Alkylphenolen mit 10-24 C-Atomen mit 3 bis 50 mol Ethylenoxid und
- E. 0-25 Gew.-% Diorganppolysiloxane mit einer Viskosität von 1000 bis 100 000 cSt enthalten, und Verfahren zum Ausrüsten von synthetischen oder natürlichen Textilmaterialien oder ihre Mischungen mit diesen.Mitteln.
- A. 50-80% by weight acylated alkanolamines from saturated or unsaturated fatty acids with 12-22 carbon atoms and alkanolamines containing 1 or 2 nitrogen atoms, 1-3 hydroxyl groups and 2-6 carbon atoms in a molar ratio of 1: 1 up to 3: 1,
- B. 10-30% by weight of water-soluble quaternary ammonium salts of the general formula:
- R 1 is an alkyl or alkenyl radical with 14-25 C atoms which is interrupted by an amide or ester group,
- R 2 is a radical such as R 1 or an alkyl radical with 1-4 C atoms, R 3 is an alkyl radical with 1-4 C atoms, a hydroxyethyl or hydroxypropyl radical,
- R 4 is an alkyl radical with 1-4 C atoms, a hydroxyethyl, hydroxypropyl or benzyl radical and
- X (-) represent an anion,
- C. 2-20% by weight of fatty acid esters from saturated or unsaturated fatty acids with 12-22 carbon atoms or dicarboxylic acids with 4 to 10 carbon atoms and mono- to tetravalent alcohols with 3-20 carbon atoms,
- D. 0-20% by weight of ethylene oxide adducts of fatty acids with 12-22 C atoms or of fatty alcohols with 8-18 C atoms or of alkyl or dialkylamines with 12-36 C atoms or of alkylphenols with 10 -24 C atoms with 3 to 50 mol ethylene oxide and
- E. 0-25 wt .-% Diorgan p polysiloxanes with a viscosity of 1000 to 100 000 cSt contain, and methods for finishing synthetic or natural textile materials or their mixtures with these.
Die acylierten Alkanolamine, A., die beispielsweise bei K. Lindner "Tenside-Textilhilfsmittel-Waschrohstoffe", 2. Auflage, Band 1, S. 904 und 993, und bei Schwartz-Perry "Surface Active Agents"1949, Bd. 1, S. 173, beschrieben sind, enthalten je nach verwendeten Alkanolaminen Amid- und/oder Estergruppen.The acylated alkanolamines, A., which, for example, in K. Lindner's "Tenside-Textile Aid Wash Raw Materials", 2nd Edition, Volume 1, pp. 904 and 993, and in Schwartz-Perry "Surface Active Agents" 1949, Vol. 1, P. 173, contain amide and / or ester groups, depending on the alkanolamines used.
Zu ihrer Herstellung finden Carbonsäuren natürlicher oder synthetischer Herkunft Verwendung z.B. Laurinsäure, Myristinsäure, Palmitinsäure, Stearinsäure, Behensäure, ölsäure oder ihre Gemische, wie sie z.B. aus Kokosöl, Palmkernöl oder Talg hergestellt werden, oder verzweigtkettige Säuren aus der Oxosynthese, z.B. Isostearinsäure, oder deren Säurechloride Verwendung. Bevorzugt finden Stearinsäure und Behensäure in Form ihrer technischen Qualitäten Verwendung.Carboxylic acids of natural or synthetic origin are used in their production, e.g. Lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid or their mixtures, e.g. be made from coconut oil, palm kernel oil or tallow, or branched chain acids from oxosynthesis, e.g. Isostearic acid, or its acid chlorides use. Stearic acid and behenic acid are preferably used in the form of their technical qualities.
Zu den geeigneten hydroxylgruppenhaltigen Aminen zählen Monoethanolamin, Diethanolamin, Triethanolamin, N-Methyldiethanolamin, N-(2-Aminoethyl)-ethanolamin, 1-Aminopropanol und Bis-(2-hydroxy-propyl)-amin. Bevorzugt verwendet werden N-(2-Aminoethyl)-ethanolamin, Monoethanolamin und Diethanolamin.Suitable amines containing hydroxyl groups include monoethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N- (2-aminoethyl) -ethanolamine, 1-aminopropanol and bis- (2-hydroxypropyl) amine. N- (2-Aminoethyl) ethanolamine, monoethanolamine and diethanolamine are preferably used.
Die wasserlöslichen quaternären Ammoniumsalze B. enthalten als hydrophoben Rest mindestens eine Alkylkette, die durch eine Amid- oder Estergruppe unterbrochen ist. Zu ihrer Herstellung werden nach bekannten Methoden, die z.B. bei Schwartz-Perry "Surface Active Agents", 1949, Bd. 1, S. 118 und bei Jüg'ermann" Cationic Surfactants" 1970, S. 29, beschrieben sind, Mono-, Di- oder Triamine, die eine tertiäre Aminogruppe und eine oder zwei primäre Aminogruppen und eine oder zwei Hydroxylgruppen enthalten, mit den unter A. genannten Säuren acyliert.
- R1 steht bevorzugt für den Rest
- R5 einen Alkyl- oder Alkenylrest mit 12 bis 22 C-Atomen,
- R6 Ethylen oder Propylen und
- Y NH oder O bedeuten.
- X(-) steht vorzugsweise für Chlorid, Bromid, Sulfat, Phosphat, Methosulfat oder Dimethylphosphit.
- R 1 preferably represents the rest
- R 5 is an alkyl or alkenyl radical having 12 to 22 carbon atoms,
- R 6 ethylene or propylene and
- Y is NH or O.
- X (-) preferably represents chloride, bromide, sulfate, phosphate, methosulfate or dimethyl phosphite.
Geeignete Amine für die Herstellung von B sind z.B.;
- 3-Amino-1-dimethylamino-propan, 3-Amino-l-diethylamino-propan, Methyl-bis-(3-amino-propyl)-amin, Bis-(2-methylamino-ethyl)-methylamin, 2-Dimethylamino-ethanol, Methyl-bis-(2-hydroxy-ethyl)-amin oder 3-Dimethyl- amino-1-propanol.
- 3-amino-1-dimethylamino-propane, 3-amino-1-diethylamino-propane, methyl-bis- (3-amino-propyl) -amine, bis- (2-methylamino-ethyl) -methylamine, 2-dimethylamino- ethanol, methyl bis (2-hydroxyethyl) amine or 3-dimethylamino-1-propanol.
Bevorzugte Verbindungen B. sind Umsetzungsprodukte von technischer Stearinsäure oder Behensäure mit 3-Amino-1-dimethylamino-propan oder 3-Amino-1-diethylamino-propan, die mit Dimethylsulfat oder Dimethylphosphit quaterniert werden.Preferred compounds B. are reaction products of technical stearic acid or behenic acid with 3-amino-1-dimethylamino-propane or 3-amino-1-diethylamino-propane, which are quaternized with dimethyl sulfate or dimethyl phosphite.
Die Quaternierung geschieht nach üblichen Methoden ohne Lösungsmittel oder in einem Lösungsmittel, wobei neben Wasser oder Ethylalkohol auch die acylierten Alkanolamine A. in geschmolzener Form dienen können, sofern sie kein tertiäres Stickstoffatom enthalten.The quaternization is carried out by conventional methods without a solvent or in a solvent, and in addition to water or ethyl alcohol, the acylated alkanolamines A. can also be used in molten form, provided that they do not contain a tertiary nitrogen atom.
Als Quaternierungsmittel sind geeignet: Methylchlorid, Dimethylsulfat, Dimethylphosphit oder Ethylenoxid, wobei im letzteren Falle die Reaktion in schwefelsaurer oder phosphorsaurer Lösung vorgenommen wird.Suitable quaternizing agents are: methyl chloride, dimethyl sulfate, dimethyl phosphite or ethylene oxide, in which case the reaction is carried out in sulfuric or phosphoric acid solution.
Die Substanzen der beiden Stoffgruppen A und B lassen sich auch in einem Eintopf-Verfahren dadurch herstellen, daß man Gemische der für beide Gruppen genannten Amine mit Fettsäuren umsetzt und anschließend dem Anteil an tertiären Aminogruppen entsprechend quaterniert.The substances of the two groups of substances A and B can also be prepared in a one-pot process by reacting mixtures of the amines mentioned for both groups with fatty acids and then quaternizing the proportion of tertiary amino groups.
Zur Herstellung der Carbonsäureester C werden bevorzugt ein- bis vierwertige Alkohole mit 3-20 C-Atomen verwendet, deren Alkylketten durch Sauerstoff unterbrochen sein können.Mono- to tetravalent alcohols having 3-20 C atoms, the alkyl chains of which may be interrupted by oxygen, are preferably used to prepare the carboxylic acid esters C.
Als Beispiele für die Ester C seien genannt:
- Butylstearat, 2-Ethyl-hexyl-stearat, Octadecylstearat, Isotridecylstearat, 2-Ethyl-hexyl-oleat, Di-2-ethyl-hexyl- sebacat, Pentaethylen-glykol-dilaurat, Trimethylolpropantrilaurat und Pentaerythrit-tetrapelargonat.
- Butyl stearate, 2-ethyl hexyl stearate, octadecyl stearate, isotridecyl stearate, 2-ethyl hexyl oleate, di-2-ethyl hexyl sebacate, pentaethylene glycol dilaurate, trimethylol propane trilaurate and pentaerythritol tetrapelargonate.
Zur Verbesserung der Löslichkeit können gegebenenfalls Ethylenoxid-Addukte von Fettsäuren, Fettalkolen, Fettaminen oder Alkylphenolen eingesetzt werden. Der optimale Oxethylierungsgrad ist von Fall zu Fall verschieden und kann von 3-50 mol Ethylenoxid pro mol Ausgangssubstanz betragen.Ethylene oxide adducts of fatty acids, fatty alcohols, fatty amines or alkylphenols can optionally be used to improve solubility. The optimal degree of oxyethylation differs from case to case and can be from 3-50 moles of ethylene oxide per mole of starting substance.
Bei Bedarf können wäßrige Emulsionen von durch Emulsionspolymerisation hergestellten Dimethylpolysiloxanen mit mittleren Molekulargewichten von 1000 bis 100 000 verwendet werden.If necessary, aqueous emulsions of Emul Sion polymerization produced dimethylpolysiloxanes with average molecular weights of 1000 to 100,000 can be used.
Die erfindungsgemäßen Zusammensetzungen können darüber hinaus noch andere Bestandteile enthalten, wie sie bei Textilhilfsmitteln üblich sind. Dazu zählen Schutzkolloide, Parfums, Fungizide oder Bakterizide sowie Schaumdämpfungsmittel.The compositions according to the invention can also contain other constituents as are customary in textile auxiliaries. These include protective colloids, perfumes, fungicides or bactericides as well as anti-foaming agents.
Zur besseren Handhabung in der Praxis werden die erfindungsgemäßen Gemische in wasserhaltige Zubereitungen übergeführt. Dazu werden die Mischungen über den Schmelzpunkt erwärmt und unter Rühren nach Zugabe der entsprechenden Menge warmen Wassers homogen verrührt. Nach dem Abkühlen auf Raumtemperatur erhält man flüssige stabile Lösungen oder Emulsionen, die vorzugsweise 10-30 Gew.-% der erfindungsgemäßen Textilbehandlungsmittel enthalten.For better handling in practice, the mixtures according to the invention are converted into water-containing preparations. For this purpose, the mixtures are heated above the melting point and, with stirring after the appropriate amount of warm water has been added, are stirred homogeneously. After cooling to room temperature, liquid stable solutions or emulsions are obtained which preferably contain 10-30% by weight of the textile treatment agents according to the invention.
Das Aufbringen der Mischungen auf das Textilmaterial kann nach bekannten Methoden im Ausziehverfahren (Haspelkufe, Düsen-Färbe-Aggregat), durch Foulardieren oder durch Sprühen erfolgen. Dabei gilt als besonderer Vorteil, daß sich die erfindungsgemäßen Textilbehandlungsmittel mit Düsen-Färbe-Aggregaten aufbringen lassen.The mixtures can be applied to the textile material by known methods in the exhaust process (reel runner, nozzle-dyeing unit), by padding or by spraying. It is a particular advantage that the textile treatment agents according to the invention can be applied with nozzle-dyeing units.
Textile Verarbeitungsprozesse, wie das Vernähen oder Tuften, stellen an das Textilmaterial hohe Anforderungen hinsichtlich der Oberflächenglätte. Hohe Nadelgeschwindigkeiten führen zu thermischen und mechanischen Belastungen des Nähgutes, die bei mangelnder Oberflächenglätte zu Fadenbrüchen und Maschensprengschäden führen können. Dieser Nachteil kann dadurch umgangen werden, daß das Textilmaterial mit einer glättenden Avivage versehen wird. Es ist bekannt, zu diesem Zweck Emulsionen oder Dispersionen von Paraffinkohlenwasserstoffen oder von Wachsen zu verwenden. So beschreiben z.B. die deutschen Offenlegungsschriften 26 21 881, 27 33 493, 28 16 196 und 28 30 173 kationische Emulsionen von Paraffinkohlenwasserstoffen, wobei kationische Tenside als Emulgatoren dienen. Die DE-OS 30 03 851 beschreibt Dispersionen von oxidierten Wachsen, während die DE-OS 25 35 768 Dispersionen von Polysiloxanen und Kohlenwasserstoffen oder fluorhaltigen Polymeren zur Erzielung hoher Oberflächenglätten verwendet. Auch ist bekannt, zusammen mit Paraffinkohlenwasserstoffen Fettsäureester als Gleitmittel zu verwenden.Textile processing processes, such as sewing or tufting, place high demands on the textile material with regard to surface smoothness. High needle speeds lead to thermal and mechanical stress on the material to be sewn, which is due to a lack of surfaces smoothness can lead to thread breaks and stitch detonation damage. This disadvantage can be avoided by providing the textile material with a smoothing finish. It is known to use emulsions or dispersions of paraffinic hydrocarbons or waxes for this purpose. For example, German Offenlegungsschriften 26 21 881, 27 33 493, 28 16 196 and 28 30 173 describe cationic emulsions of paraffin hydrocarbons, cationic surfactants serving as emulsifiers. DE-OS 30 03 851 describes dispersions of oxidized waxes, while DE-OS 25 35 768 uses dispersions of polysiloxanes and hydrocarbons or fluorine-containing polymers to achieve high surface smoothness. It is also known to use fatty acid esters as lubricants together with paraffin hydrocarbons.
Während diese Emulsionen dem Textilmaterial eine hohe Oberflächenglätte verleihen, resultiert in den meisten Fällen ein Warengriff, der die zusätzliche Verwendung eines Textilweichmachers erfordert. Daneben haben diese Emulsionen oder Dispersionen häufig den Nachteil, daß sie für den Einsatz auf Düsen-Färbe-Apparaten, auch "Jet-Anlagen" genannt, die mit kurzen Flotten arbeiten, nicht geeignet sind, weil die verfahrensbedingten hohen Scherkräfte die Emulsionen zerstören. Dadurch kommt es zu Aufrahmungen und Fleckenbildung sowie zu ungleicher Avivageverteilung auf dem Textilmaterial. Die vorliegende Erfindung stellt nur Avivagemittel zur Verfügung, die dem Textilmaterial neben hoher Oberflächenglätte einen ansprechenden Griff verleihen und eine solche Flottenstabilität aufweisen, daß sie auch auf Düsen-Färbe-Apparaten einsetzbar sind.While these emulsions give the textile material a high surface smoothness, in most cases there is a handle which requires the additional use of a textile softener. In addition, these emulsions or dispersions often have the disadvantage that they are not suitable for use on jet dyeing apparatus, also called "jet systems", which work with short liquors, because the high shear forces caused by the process destroy the emulsions. This leads to creaming and staining, as well as uneven finish distribution on the textile material. The present invention only provides finishing agents which unite the textile material in addition to high surface smoothness give an appealing handle and have such a stability that they can also be used on jet dyeing machines.
überraschend wurde gefunden, daß die erfindungsgemäßen Mittel ohne Verwendung von Paraffinen oder Wachsen ausgezeichnete Weichmacher und Glättemittel für Textilmaterialien jeder Art darstellen.Surprisingly, it was found that the agents according to the invention, without the use of paraffins or waxes, are excellent plasticizers and smoothing agents for textile materials of all kinds.
Tabelle 1 zeigt die Molmengen der eingesetzten Komponenten zur Herstellung der acylierten Alkanolamine A und die Säurezahlen, wie sie nach der Umsetzung bei vermindertem Druck und erhöhter Temperatur erhalten wurden.
Tabelle 2 zeigt, in welchem Molverhältnis die einzelnen Komponenten zur Herstellung der basischen Fettsäureamide bzw. Fettsäureester umgesetzt wurden, die als Ausgangsprodukte für die Herstellung der quaternären Ammoniumsalze dienen. Die letzte Zeile gibt die Säurezahlen wieder, die bei der Reaktion der Komponenten bei erhöhter Temperatur und vermindertem Druck erhalten wurden.
Tabelle 3 gibt eine Übersicht über die Herstellung der verwendeten quaternären Ammoniumsalze.
Beispiele dafür, daß man die acylierten Alkanolamine in geschmolzenem Zustand als Lösungsmittel für die Quaternierung verwenden kann, zeigt Tabelle 4.
Die angegebenen Zahlen sind Gewichtsprozente. Die Quaternierungen wurden so durchgeführt, daß pro Mol tert. Stickstoffgruppe ein Mol Quaternierungsmittel eingesetzt wurde. Die Umsetzungen wurden in der Schmelze bei 90-100°C durchgeführt.The figures given are percentages by weight. The quaternizations were carried out so that tert per mol. Nitrogen group was used a mole of quaternizing agent. The reactions were carried out in the melt at 90-100 ° C.
Zur Herstellung der erfindungsgemäßen Textilbehandlungsmittel werden folgende Komponenten gemischt:
- 1) : Rilanit STS-RR, Fa. Henkel, Düsseldorf1): Rilanit STS-R R , from Henkel, Düsseldorf
- 2) : Emery 2485 R Fa. Unilever - Emery, Gouda, Holland2): Emery 2485 R from Unilever - Emery, Gouda, Holland
- 3) : Rilanit ITS R, Fa. Henkel, Düsseldorf3): Rilanit ITS R , Henkel, Düsseldorf
- 4) : Rilanit EHS R, Fa. Henkel, Düsseldorf4): Rilanit EHS R , Henkel, Düsseldorf
Die Vernähbarkeit wurde mit der folgenden Versuchsreinrichtung geprüft:
- In einem Düsen-Färbe-Apparat, Marke "Labor-Jumbo-Jet" der Firma Mathis, wurde Baumwoll-Interlock, mit Leva- fix(R)-Farbstoffen reaktiv gefärbt im Farbton schwarz, nach dem Spülen 20 min lang mit den Produkten T 1 bis T 8 der Tabelle 5 im Flottenverhältnis 1 : 10 bei 40°C, essigsauer bei pH 5, behandelt. Die Konzentration der Behandlungsmittel lag bei 4 %, bezogen auf das eingesetzte Warengewicht.
- In a nozzle-dyeing apparatus, brand "Labor-Jumbo-Jet" from Mathis, cotton interlock, reactively dyed with Levafix (R) dyes in the color black, was rinsed for 20 minutes with the products T 1 to T 8 of Table 5 in a liquor ratio 1:10 at 40 ° C, acetic acid at pH 5, treated. The concentration of the treatment agents was 4%, based on the weight of the goods.
Bei allen 8 Versuchen verlief die Ausrüstung problemlos ohne störende Schaumbildung oder Abscheidungen aus der Flotte.In all 8 trials, the equipment ran smoothly without disruptive foaming or separations from the fleet.
Ein Teil des Materials wurde bei 80°C getrocknet, zweimal 10 sec. lang bei 120°C gedämpft und bei 23°C u. 65 % rel. Feuchte konditioniert.Part of the material was dried at 80 ° C, steamed twice for 10 seconds at 120 ° C and at 23 ° C u. 65% rel. Conditioned moisture.
Ein anderer Teil des ausgerüsteten Materials wurde nach dem Trocknen bei 80°C zweimal 10 sec. lang bei 120°C gedämpft, anschließend noch 20 sec. lang bei 170°C fixiert und dann bei 23°C und 65 % rel. Feuchte konditioniert.Another part of the finished material was steamed twice at 120 ° C for 10 seconds after drying at 80 ° C, then fixed at 170 ° C for a further 20 seconds and then at 23 ° C and 65% rel. Conditioned moisture.
Für den Nähtest wurden Stoffabschnitte von 35 x 80 cm in doppelter Lage mit einer Industrie-Nähmaschine der Fa. Singer, Typ Centurion 121 D 200 B unter Verwendung einer Nadel der Stärke 90 bei 4800 Stichen/min. ohne Nähfäden vernäht.For the sewing test, fabric sections of 35 x 80 cm were double-layered with an industrial sewing machine from Singer, type Centurion 121 D 200 B, using a size 90 needle at 4800 stitches / min. sewn without sewing threads.
Die Stoffabschnitte wurden dann in einem Spannrahmen unter einer Dehnung von 88 % gespannt und im Gegenlicht die Zahl der Maschensprengschäden über eine Nahtlänge von 80 cm ermittelt.The fabric sections were then stretched in a stenter under an elongation of 88% and the number of stitch blasting damage over a seam length of 80 cm was determined in the backlight.
Tabelle 6 gibt die ermittelten Versuchsdaten im Vergleich zu einer unbehandelten Ware wieder.
Das Produkt T 2 wurde nach folgender Rezeptur eingesetzt: Baumwoll-Interlock, reaktivgefärbt schwarz.
Düsen-Färbe-Apparat: "Surfer", Fa. ESPA
Flottenverhältnis 1 : 12
Konzentration 4 % bezogen auf Warengewicht
20 min bei 40°C, essigsauer pH 5
Nach dem Schleudern wurde bei 80 - 100°C getrocknet und mit Sattdampf gedämpft.The product T 2 was used according to the following recipe: cotton interlock, reactive-dyed black.
Nozzle dyeing apparatus: "Surfer", from ESPA
Fleet ratio 1:12
Concentration 4% based on the weight of the goods
20 min at 40 ° C, acetic acid pH 5
After spinning, it was dried at 80-100 ° C and steamed with saturated steam.
Beim Vernähen unter Praxisbedingungen mit einer Industrie-Nähmaschine, 4500 - 5000 Stiche/min, Nadelstärke 90, wurden keine Maschensprengschäden beobachtet. Die Ware zeigte einen angenehmen, weichen Griff.When sewing under practical conditions with an industrial sewing machine, 4500 - 5000 stitches / min, needle size 90, no stitch explosive damage was observed. The goods showed a pleasant, soft feel.
Das Produkt T 6 wurde nach folgender Rezeptur appliziert:
- Baumwoll-Feinripp, reaktivgefärbt schwarz
- Düsen-Färbe-Apparat: "Jet R 95", Fa. Thieß
- Flottenverhältnis 1 : 10
- Konzentration 4 % bezogen auf Warengewicht
- 20 min bei 40°C, essigsauer pH 5
- Fine cotton rib, reactive-dyed black
- Nozzle dyeing apparatus: "Jet R 95", from Thieß
- Fleet ratio 1:10
- Concentration 4% based on the weight of the goods
- 20 min at 40 ° C, acetic acid pH 5
Nach dem Schleudern und Trocknen bei 80 - 100°C wurde mit Sattdampf von 100-110°C behandelt.After centrifuging and drying at 80-100 ° C, saturated steam at 100-110 ° C was used.
Beim Vernähen unter Praxisbedingungen mit einer Industrie-Nähmaschine, 4500 - 5000 Stiche/min, Nadelstärke 90, war das Material frei von Maschensprengschäden. Die Ware hatte einen angenehmen, weichen Griff.When sewing under practical conditions with an industrial sewing machine, 4500 - 5000 stitches / min, needle size 90, the material was free from stitches. The goods had a pleasant, soft feel.
Claims (5)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813138181 DE3138181A1 (en) | 1981-09-25 | 1981-09-25 | TEXTILE TREATMENT AGENTS AND THEIR USE FOR FINISHING TEXTILE MATERIALS |
| DE3138181 | 1981-09-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0075770A2 true EP0075770A2 (en) | 1983-04-06 |
| EP0075770A3 EP0075770A3 (en) | 1985-01-16 |
| EP0075770B1 EP0075770B1 (en) | 1986-11-12 |
Family
ID=6142590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP82108390A Expired EP0075770B1 (en) | 1981-09-25 | 1982-09-11 | Textile treating composition and its use in finishing textile materials |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4446034A (en) |
| EP (1) | EP0075770B1 (en) |
| JP (1) | JPS5860070A (en) |
| DE (2) | DE3138181A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0848103A2 (en) * | 1996-12-11 | 1998-06-17 | Henkel Kommanditgesellschaft auf Aktien | Treatment agent for textile and keratin fibers |
| EP0861938A2 (en) * | 1997-02-28 | 1998-09-02 | Henkel Kommanditgesellschaft auf Aktien | Composition for finishing of textile- and keratin fibers |
| EP0869168A2 (en) * | 1997-04-05 | 1998-10-07 | Henkel Kommanditgesellschaft auf Aktien | Composition for imparting hydrophilic properties to textiles |
| WO2000037735A1 (en) * | 1998-12-22 | 2000-06-29 | Bayer Aktiengesellschaft | Agents for treating textiles, method for producing them and their use |
| WO2000058547A1 (en) * | 1999-03-29 | 2000-10-05 | Bayer Aktiengesellschaft | Treatment agents for textiles, method of producing same and their use |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60139868A (en) * | 1983-12-24 | 1985-07-24 | ライオン株式会社 | Softener composition |
| GB8400899D0 (en) * | 1984-01-13 | 1984-02-15 | Procter & Gamble | Granular detergent compositions |
| GB2188653A (en) * | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
| GB8817961D0 (en) * | 1988-07-28 | 1988-09-01 | Dow Corning Ltd | Compositions & process for treatment of textiles |
| GB8916307D0 (en) * | 1989-07-17 | 1989-08-31 | Unilever Plc | Fabric softening composition |
| DE4026029A1 (en) * | 1989-09-07 | 1992-02-20 | Sandoz Ag | AQUEOUS AMINOPOLYSILOXAN MICROEMULSIONS, THEIR PRODUCTION AND USE |
| US5059442A (en) * | 1989-09-19 | 1991-10-22 | Nabisco Brands, Inc. | Primary amide esters as low calorie fat mimetics |
| US5234720A (en) * | 1990-01-18 | 1993-08-10 | Eastman Kodak Company | Process of preparing lubricant-impregnated fibers |
| JPH0759793B2 (en) * | 1990-08-22 | 1995-06-28 | 花王株式会社 | Softening agent |
| JPH0759792B2 (en) * | 1990-08-22 | 1995-06-28 | 花王株式会社 | Softening agent |
| US5944852A (en) * | 1996-10-23 | 1999-08-31 | Solutia Inc. | Dyeing process |
| US5830240A (en) * | 1996-10-23 | 1998-11-03 | Solutia Inc. | Fibers and textile materials having enhanced dyeability and finish compositions used thereon |
| US5780401A (en) * | 1997-03-14 | 1998-07-14 | The Lubrizol Corporation | Non-flating slip-enhancing additives for coatings |
| KR100351235B1 (en) * | 1999-12-15 | 2002-09-09 | 주식회사 아이씨켐 | A composition for treating synthetic fiber |
| JP6178720B2 (en) * | 2013-12-25 | 2017-08-09 | 花王株式会社 | Liquid softener composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR742700A (en) * | 1930-09-29 | 1933-03-13 | ||
| FR1281984A (en) * | 1959-11-25 | 1962-01-19 | Bayer Ag | Improvements to means for preventing electrostatic charging of synthetic high polymers |
| US3451927A (en) * | 1964-07-08 | 1969-06-24 | Lever Brothers Ltd | Fabric conditioner |
| US3652419A (en) * | 1968-03-06 | 1972-03-28 | Witco Chemical Corp | Antistatic fiber lubricant |
| US3868270A (en) * | 1972-12-04 | 1975-02-25 | Du Pont | Fibers with finish containing organic phosphates and sulphates |
| EP0013780A1 (en) * | 1979-01-11 | 1980-08-06 | THE PROCTER & GAMBLE COMPANY | Concentrated fabric softening composition |
| EP0018039A1 (en) * | 1979-04-21 | 1980-10-29 | THE PROCTER & GAMBLE COMPANY | Fabric softening composition |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE154712C (en) * | ||||
| US3223545A (en) * | 1962-10-08 | 1965-12-14 | Phillips Petroleum Co | Dialkanol amide antistatic composition for polyolefins |
| JPS6014146B2 (en) * | 1977-01-29 | 1985-04-11 | ライオン株式会社 | fiber softening composition |
| GR67665B (en) * | 1979-05-21 | 1981-09-02 | Unilever Nv |
-
1981
- 1981-09-25 DE DE19813138181 patent/DE3138181A1/en not_active Withdrawn
-
1982
- 1982-09-08 US US06/415,866 patent/US4446034A/en not_active Expired - Lifetime
- 1982-09-11 EP EP82108390A patent/EP0075770B1/en not_active Expired
- 1982-09-11 DE DE8282108390T patent/DE3274270D1/en not_active Expired
- 1982-09-21 JP JP57163276A patent/JPS5860070A/en active Granted
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR742700A (en) * | 1930-09-29 | 1933-03-13 | ||
| FR1281984A (en) * | 1959-11-25 | 1962-01-19 | Bayer Ag | Improvements to means for preventing electrostatic charging of synthetic high polymers |
| US3451927A (en) * | 1964-07-08 | 1969-06-24 | Lever Brothers Ltd | Fabric conditioner |
| US3652419A (en) * | 1968-03-06 | 1972-03-28 | Witco Chemical Corp | Antistatic fiber lubricant |
| US3868270A (en) * | 1972-12-04 | 1975-02-25 | Du Pont | Fibers with finish containing organic phosphates and sulphates |
| EP0013780A1 (en) * | 1979-01-11 | 1980-08-06 | THE PROCTER & GAMBLE COMPANY | Concentrated fabric softening composition |
| EP0018039A1 (en) * | 1979-04-21 | 1980-10-29 | THE PROCTER & GAMBLE COMPANY | Fabric softening composition |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0848103A2 (en) * | 1996-12-11 | 1998-06-17 | Henkel Kommanditgesellschaft auf Aktien | Treatment agent for textile and keratin fibers |
| EP0848103A3 (en) * | 1996-12-11 | 1999-01-20 | Henkel Kommanditgesellschaft auf Aktien | Treatment agent for textile and keratin fibers |
| EP0861938A2 (en) * | 1997-02-28 | 1998-09-02 | Henkel Kommanditgesellschaft auf Aktien | Composition for finishing of textile- and keratin fibers |
| EP0861938A3 (en) * | 1997-02-28 | 1999-01-20 | Henkel Kommanditgesellschaft auf Aktien | Composition for finishing of textile- and keratin fibers |
| EP0869168A2 (en) * | 1997-04-05 | 1998-10-07 | Henkel Kommanditgesellschaft auf Aktien | Composition for imparting hydrophilic properties to textiles |
| EP0869168A3 (en) * | 1997-04-05 | 1999-01-20 | Henkel Kommanditgesellschaft auf Aktien | Composition for imparting hydrophilic properties to textiles |
| WO2000037735A1 (en) * | 1998-12-22 | 2000-06-29 | Bayer Aktiengesellschaft | Agents for treating textiles, method for producing them and their use |
| WO2000058547A1 (en) * | 1999-03-29 | 2000-10-05 | Bayer Aktiengesellschaft | Treatment agents for textiles, method of producing same and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0075770A3 (en) | 1985-01-16 |
| JPS5860070A (en) | 1983-04-09 |
| DE3138181A1 (en) | 1983-04-14 |
| EP0075770B1 (en) | 1986-11-12 |
| JPS6323314B2 (en) | 1988-05-16 |
| US4446034A (en) | 1984-05-01 |
| DE3274270D1 (en) | 1987-01-02 |
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