US3334960A - Process for coloring nitrogen-containing fibrous material - Google Patents

Process for coloring nitrogen-containing fibrous material Download PDF

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US3334960A
US3334960A US519521A US51952166A US3334960A US 3334960 A US3334960 A US 3334960A US 519521 A US519521 A US 519521A US 51952166 A US51952166 A US 51952166A US 3334960 A US3334960 A US 3334960A
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parts
acid
ethylene oxide
water
dyestuffs
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Abel Heinz
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BASF Schweiz AG
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Ciba AG
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    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
    • 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
    • D06P1/0028—Dyeing with a coacervate system
    • 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
    • D06P1/60—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 polyethers
    • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
    • 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
    • D06P1/653—Nitrogen-free carboxylic acids or their salts
    • 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
    • D06P1/673—Inorganic compounds
    • D06P1/67316—Acids
    • 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
    • D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/928—Solvents other than hydrocarbons
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/10—Material containing basic nitrogen containing amide groups using reactive dyes
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/70—Material containing nitrile groups
    • D06P3/76—Material containing nitrile groups using basic dyes
    • 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
    • Y10S8/90—Basic emulsifiers for dyeing
    • Y10S8/901—Quaternary ammonium salts
    • 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
    • Y10S8/907—Nonionic emulsifiers for dyeing
    • 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
    • Y10S8/917—Wool or silk
    • 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
    • Y10S8/924—Polyamide fiber

Definitions

  • fibrous materials containing nitrogen can.be colored, i.e. dyed or printed at 'room higher fatty amines containing, for example 10 to 22 temperature with dyestuffs that are soluble or only disganic carboxylic acid to the preparations.
  • inorganic acids for example phosphoric acid, organic aliphatic monocarboxylic and dicarboxylic acids, above all those of low molecular binations such, for example
  • cationic assistants particularly good results have been obtained with those which owe their solubility in water exclusively to groupings containing a basic nitrogen atom.
  • These compounds are predominantly amine Y salts or quaternary ammonium salts of cyclic or openchain.
  • cetyl trimethyl ammonium bromide cetyl pyridinium' bromide
  • a quaternary salt of the reaction product of stearic acid methylolamide with triethanolamin e ,orfa quaternary salt of bis-lauryltetramethylethylenediamine.
  • com' assistants Particularly suitable cornassistants, the .componentsof such combinations having the structure defined above.
  • The. surface active.coacervating agents may be nonionic or anionic andmust be capable of causing the dye preparation tocoacerv'ate.
  • coacervation describes the deinixing of a, colloidal solution of a hydrophilic colloid to formtwo liquid phases.
  • the phase having a higher contentof colloidin this case the phase containing a larger share of auxiliaryis called the coacervate, whereas the, phase having a lower content of colweight are particularly suitable.
  • good results m are obtained by using monochloroacetic or nitric acid. Likewise good results are achieved with tartaric, propionic,
  • glycollic and lactic acid Particularly good results are obtained with acetic acid and especially with formic acid; these two acids are advantageously used in as concentrated a form as possible.
  • the amount of acid to be added may vary within rather wide limits, for example from 4 to 30% calculated on the weight of the dye preparation, though an amount of the order of 10 to 20% is preferred.
  • a wide variety of fibrous materials containing nitrogen can be dyed or printed by the. present process, including both natural and synthetic materials.
  • natural materials there may be mentioned leathers, pelts (for example sheepskins), hairs, for example human hair, hairs of goats, rabbits or hares, feathers, sisal (which contains proteinic substances embedded in cellulose) and above all wool.
  • Suitable synthetic materials are primarily those from polyaprylonitrile, polyamide (for example condensation products of hexamethylenediamine and adipic acid), polycondensates of w-aminoundecanoic acid especially of e-caprolactam. It will be readily understood that mixtures containing the afore-mentioned materials may likewise be dyed or printed.
  • Thedye preparation must contain at least one surfaceactive ""assistant. These assistants act as levelling, dispersingfor wetting agents, may have coacervating power and may be of the non-ionic or cationic kind or even of the anionic type if they have coacervating power. These surface-active agents may be used either alone or in mixtures with one another.
  • Thenon-ionic assistants are adducts of ethylene oxide withi'compounds containing at least one reactive hydrogeniatom, that is to say with compounds that contain primary or secondary amino groups or hydroxyl groups,
  • the compounds concerned are polyglycol ethers of hydroxy compounds, for example of alkylphenols, such as an octylphenol or nonylphenol, or of higher aliphatic alcohols, such as lauryl, cetyl or octadecyl alcohol, or of loidin this case the phase containing less auxiliaryis called the equilibrium liquid.
  • alkylphenols such as an octylphenol or nonylphenol
  • higher aliphatic alcohols such as lauryl, cetyl or octadecyl alcohol, or of loidin this case the phase containing less auxiliaryis called the equilibrium liquid.
  • the two phases contain the same solvent. It is another. characteristic ofa coacervated system that a small amount of colloid is capable, of taking up a relatively large amount. of solvent, in the present case water.
  • the amount of solvent taken up is, a multiple of the amount of coacer-; vating agent used.
  • the two co-existing liquid phases should be present in the form of an emulsion. If necessary, a rather stable emulsion in which the two phases are well I distributed can be prepared by adding a thickener.
  • auxiliarycapable of satisfying these conditions may belong to a wide variety of compounds. Particularly suitable for the present process are the reaction products obtained from higher fatty acids and hydroxyalkylamines.
  • Ethylene oxide adducts of such reaction products are likewise suitable.
  • Such products can be prepared, without additional use of ethylene. oxide, from higher fatty acids, preferably those-which contain about 12 carbon atoms 1 such as caprylic, stearic, oleic or especially coconut oil fatty acids, and'hydroxyalkyl amines, such as triethanolamine, dihydroxyethylenediamine and preferably diethanol amine.
  • the reaction is so conducted as to produce a molar ratio of hydroxyalkylamine-fatty acid greater than I 1, for example 2:1.
  • Such compounds have been described in US. Patent No. 2,089,212. If ethylene oxide condensation products of these compounds are required, the molecular proportion of fatty acid to ethylene oxide should be 1:2 to 1:15. The sequence in which the three reactants are reacted is immaterial.
  • R represents a hydrophobic radical
  • X represents a hydrogen atom or an acid solubilizing group
  • n is a whole number not greater than 8.
  • R represents an aliphatic, cycloaliphatic or aliphatic-aromatic radical, preferably a hydrocarbon radical with 10 to 22 carbon atoms.
  • Such radicals are derived from alcohols, such as lauryl, tridecyl, oleyl, octadecyl or hydroabiethyl alcohol, from carboxylic acids such as lauric acid or coconut oil fatty acid, and especially from alkylphenols such as octylphenol or nonylphenol.
  • assistants are obtained when the aforementioned alcohols, acids or alkylphenols are reacted with e.g. l to mols of ethylene oxide, preferably with 1 to 3 mols of ethylene oxide and the resulting reaction product is, if desired or required, etherified with a halogencarboxylic or hydroxycarboxylic acid, for example with chloroacetic acid; or is converted into an acid ester with the aid of an organic dicarboxylic acid such as maleic, malonic or succinic acid, or preferably with an inorganic polybasic acid, such as orthophosphoric acid or especially sulfuric acid.
  • an organic dicarboxylic acid such as maleic, malonic or succinic acid
  • an inorganic polybasic acid such as orthophosphoric acid or especially sulfuric acid.
  • Particularly valuable compounds in this group are those of the formula where m is a whole number, at least 7, p is a number from 1 to 5, preferably from 1, 2 or 3, and Z represents an acid water-solubilizing group, preferably the radical of a polybasic inorganic acid. It is also possible to use mixtures of assistants of the above formulae, especially those in which the ⁇ -CH CH O) radicals are non-uniform so that the average value of n or p no longer represents a whole number, and may be, for example, about 1.5. It is of special advantage to use for the manufacture of the aqueous preparations, instead of the acid ethers or esters, their alkali metal, ammonium or amine salts.
  • the amounts of coacervating agents to be used may vary within wide limits. Since the amount at which coacervation occurs differs according to the auxiliary used, it is not possible to state generally applicable limiting quantities, but it is a definite advantage if the coacervate formed constitutes at least of the total volume of the dye preparation. The amount of coacervate formed can be measured by sedimentation in a measuring cylinder or according to a microscopic method.
  • the dyestuffs to be used in the present process are at least dispersible in water, that means that they are water-soluble or only dispersible in water.
  • These dyestuffs may contain reactive groups capable of entering a covalent bond with the fibrous material or they may be. free from such groups.
  • the dyestuffs may belong to a wide variety of types, for example to the oxazine, triphenylmethane, xanthene, nitro, acridone or phthalocyanine dyestuffs, and above all to the metallized and metal-free monoazo or polyazo dyestuffs or to the anthraquinone dyestuffs.
  • reactive dyestuffs which otherwise may belong to the groups mentioned above-includes dyestuffs that are capable of forming a chemical, that is to say covalent, bond with the material to be dyed or printed.
  • groupings capable of imparting this property to the dyestuff there may be mentioned epoxide groups, ethyleneimino groups, isocyanate groups, isothiocyanate groups, carbamic acid aryl ester groups, the propiolic acid amide grouping, arylamino groups; groupings that contain a mobile substituent and are easy to split with entrainment of the bond electron pair, for example sulfohalide groups, aliphatically bound sulfuric acid ester groups and aliphatically bound sulfonyloxy groups and halogen atoms, more especially an aliphatically bound chlorine atom; above all the vinylacyl groups, such, for example, as the vinylsulfone groups and especially the carboxyvinyl group.
  • These mobile substituents are advantageously in position v or [3 of an aliphatic radical which is bound with the dyestuff molecule directly or through an amino, sulfone or sulfonic acid amide group; in the case of those relevant dyestuffs which contain as mobile substituents halogen atoms, these mobile halogen atoms may also be present in an aliphatic acyl radical, for example in an acetyl radical, or in positions 5 or out? of a propionyl or acryl radical or in a'heterocyclic radical, for example in a pyrimidine, pyridazine or triazine ring.
  • the dyestuffs contain advantageously a grouping of the formula in which X represents a nitrogen bridge and Z a hydrogen atom, a possibly substituted amino group, an etherified hydroxyl or mercapto group or a halogen atom or an alkyl, aryl or aralkyl group and A represents a hydrogen or halogen atom.
  • the halogen atoms are, for example, bromine atoms, or preferably chlorine atoms.
  • dyestuffs containing diphenoxytriazine groups or those which contain a grouping of the formula where R stands for an ortho-arylene radical.
  • Suitable reactive groupings are the following radicals: Trichloropyridazine, dichloroquinoxaline, dichlorobutene, halogenated pyridazone, sulfonyldichloropropylamide, allylsulfone, allylsulfide, 2-halogenobenzthioazole-carbarnide and ,B-sulfatopropionic acid. amide.
  • reactive dyestuffs that are derived from azo dyestuffs and contain as the reactive group at least one acrylamide or a-halogenoacrylamide group, that is to say an ethylenically unsaturated group, or a group convertible thereinto, for example an azfl-dihalogenopropionyl group.
  • Preferred azo dyestuffs are those which contain sulfonic acid groups and have affinity for wool, for example from an acetic acid or sulfuric acid bath.
  • acid azo-chromium complex dyestuffs containing one atomic production of chromium for every dyestuff molecule.
  • metallized dyestuffs are suitable but also those which are subjected to metallization only in the course of the dyeing process.
  • particularly valuable results have been obtained with ortho: orthd-dihydroxyazo dyestuffs and with dyestuffs containing ortho-hydroxycarboxy groupings which are conventionally formed in acid dyeba-ths with metal donors, more especially potassium bichromate, at an elevated temperature.
  • azo metal complexes containing one atomic proportion of metal for every two dyestuff molecules in the case where coacervating surfaceactive assistants are used.
  • suitable metal atoms in this connection are chromium and cobalt.
  • These 1:2- metal complexes may be free from the afore-mentioned acid water-solubilizing groups and contain in their place alkylsulfone or sulfonamide groups.
  • the present process is suitable for coloring fibrous ma terials containing nitrogen at room temperature.
  • the impregnation with the aqueous preparation can be carried out on a padder, or the fibrous material can be printed, preferably by the slubbing printing method. Best results have been obtained in vigoureux printing.
  • room temperature signifies the temperature in the room concerned or a temperature that varies only insignificantly therefrom and it is immaterial whether this temperature is high or low. It is taken to be on an average about 20 C.; if it is higher, the storing period is correspondingly shorter, when it is lower, the storing period is correspondingly extended.
  • the minimum storing period is 1-0 minutes, but it can be advantageously extended, for example up to 24 to 48 hours, especially in the case of medium strong to dark shades.
  • the material is washed in order to remove any acid residues from the dyed or printed material.
  • the washing operation may be performed with hot or preferably cold washing liquors which, for the purpose of neutralizing the excess acid, contain an alkali metal compound, such, for example, as sodium carbonate or sodium hydroxide or preferably ammonia.
  • the dye preparations may contain thickening agents, provided they are compatible with acids.
  • thickening agents there are suitable, above all, starch ethers, carboxyalkyl celluloses, especially carboxymethyl cellulose, etherified carbubic acids or compounds having similar effects.
  • a solution promoter that is to say, as is commonly known, a substance that renders compounds that are practically insoluble in a certain solvent soluble in that particular solvent.
  • a solution promoter that is to say, as is commonly known, a substance that renders compounds that are practically insoluble in a certain solvent soluble in that particular solvent.
  • compounds there are preferably used in the present process derivatives of ethyleneglycol.
  • Particularly suitable for this purpose are polyethyleneglycols of widely varying molecular weights and monomeric glycols etherified with lower alcohols (for example those containing 1 to 4 carbon atoms), more especially ethyleneglycol monoethyl ether.
  • Example 1 Pure wool gabardine piecegoods are impregnated in the triangular interspace between the rollers of a horizontal padder with the following preparation and then squeezed to a weight increase of 70%:
  • the Wool gabardine piecegoods can be replaced by slubbings, loose wool, human hair, feathers, wool felts, ladies dress materials or other woollen fabrics of any quality and state of processing.
  • the storing time can be reduced down to 3 hours or extended up to 24 hours.
  • the skin is dyed a full yellow shade.
  • Chrome-tanned leather can be dyed in a similar manner.
  • Example 6 A fabric of which the fibers consist predominantly of a copolymer of acrylonitrile and vinyl acetate is impregnated on a two-roller padder and then expressed to a weight increase of about 70%.
  • the padding liquor consists of:
  • Example 8 A mixed fabric consisting of equal parts of wool and polyamide fibers (obtained by polycondensation of adipic acid and hexamethylene diamine) is impregnated on a two-roller padder With a liquor of the following composition: 7
  • the mixed fabric is dyed a tone-in-tone orangered.
  • Example 9 A fabric of real silk is impregnated on a padder and expressed to a weight increase of 70%.
  • the padding liquor has the following composition:
  • HOaS 803B 5 parts of a reaction product of '100 parts of commercial oleylamine and 113 parts of ethylene oxide 2 parts of an adduct of 8 mols of ethylene oxide with 1 mol of para-tertiary octylphenol.
  • 300 parts of a 5% aqueous thickening of etherified carubic acids 200 parts of formic acid 483 parts of water '15
  • the padding liquor used consists of:
  • the padded felt is reeled, wrapped airtight in a polyethylene film and stored for 48 hours at room tempera ture. After having been so stored the felt is thoroughly rinsed with cold water on a full-width washing machine and then dried. The resulting strong brown shade has good properties of fastness.
  • Example 12 Pure woollen ladies dress material is impregnated on a two-roll padder with the following preparation and then squeezed to a weight increase of 80% parts of the dyestuff of the formula 40 parts of a reaction product from 1 mol of coconut oil fatty acid and 2 mols of diethanolamine 100 parts of a 5% aqueous thickener of etherified carubic acids 2 parts of a silicone based anti-foaming agent 200 parts of formic acid of 85% strength, and
  • a sheepskin can be dyed, and in this case the impregnation is advantageously performed by brushing. In otherwise identical manner a perfect dyeing results which may require a slight after-tanning depending on the tanning method original used.
  • Example 13 A so-called stretch fabric for ski clothes, whose weft consists of wool and the warp of crimped continuous polyamide filaments from a hexamethylenediamine adipate condensate, is impregnated on a 3-rol1 padder with the following preparation and then squeezed to a weight increase of 100%:
  • the dyestuif of the formula SOaH 40 parts of a 63% solution of the diethanolamine salt of coconut oil fatty acid, coconut oil fatty acid-polyethyleneglycol ester with 6-8 mols of ethylene oxide sodium tetralinsulphonate in aqueous isopropanol 100 parts of a 5% aqueous thickener from etherified carubic acids 2 parts of a silicone based anti-foaming agent 200 parts of formic acid of 85 strength and 648 parts of water.
  • the padded material is reeled, wrapped airtight in a rubber blanket and stored for 24 hours at room temperature.
  • the fabric is then rinsed in cold water, washed for 20 minutes in a cold bath containing in 1000 parts of, 5 water 1 part of ammonia and 0.5 part of the reaction product of 1 mol of coconut oil fatty acid with 2 mols of diethanolamine and finally once more rinsed.
  • a deep blue tone-in-tone dyeing is obtained.
  • Example 14 A carpet having a jute backing and a pile of textured polyarnide from e-caprolactam is impregnated by immersing it twice on a 3-roll padder in the following preparation:
  • the carpet is then thoroughly rinsedin cold water and washed for 15 minutes in a bath maintained at 30 C. which contains for every 1000 parts of water 1 part of sodium carbonate and 1 part of heptadecenyl benzimidazole sulphonate.
  • the carpet is once more rinsed and then dried. It is dyed a strong yellow shade, while the jute backing is only faintly dyed.
  • a process for coloring fibrous materials containing nitrogen at room temperature with dyestuffs that are at least dispersible in water in the presence of at least one surfactant selected from the group consisting of nonionic ethylene oxide condensation products,cationic compounds containing a quaternary nitrogen atom and nonionic and anionic coacervating agent the improvement which comprises bringing the material to be colored into contact with an aqueous preparation consisting substantially of 4 to 30%, calculated on the total weight of the preparation and 100% strength acid, of an aliphatic carboxylic acid with at most 5 carbon atoms then storing the material so treated for at least minutes during which time the material is prevented from drying whereupon it is finished off by being washed.
  • aqueous preparation containing a combination of two non-ionic surfactants one of which is a condensation product of ethylene oxide with a fatty amine containing 10 to 22 carbon atoms and the other is a condensation product of ethylene oxide with an aryl phenol containing 6 to 12 carbon atoms in the alkyl radical.
  • a process for coloring according to claim 1 the improvement which comprises applying to wool an aqueous preparation of a coacervated two-phase system wherein the two-phase system is formed by a coacervating surfactant selected from the group consisting of a reaction product of a higher fatty acid with hydroxyalkyl amines and a compound of the formula wherein R is a hydrophobic radical, X represents a member selected from the group consisting of hydrogen and an acid solubilizing group and n is a whole number from 1 to 8 and contains at least one dyestufl? selected from the group consisting of a water-soluble 1:1-metal complex azo dyestufi and a water-soluble metal-free acid wool dyestutf.
  • a coacervating surfactant selected from the group consisting of a reaction product of a higher fatty acid with hydroxyalkyl amines and a compound of the formula wherein R is a hydrophobic radical, X represents a member selected from the
  • a process for coloring comprising applying to wool an aqueous preparation of a coacervated two-phase system wherein the two-phase system is formed by a coacervating surfactant selected from the group consisting of a reaction product of a higher fatty acid with hydroxyalkyl amines and a compound of the formula wherein R is a hydrophobic radical, X represents a member selected from the group consisting of hydrogen and an acid solubilizing group and n is a whole number from 1 to 8 and contains at least one water-soluble 1:2-meta1 complex azo dyestufi.
  • a coacervating surfactant selected from the group consisting of a reaction product of a higher fatty acid with hydroxyalkyl amines and a compound of the formula wherein R is a hydrophobic radical, X represents a member selected from the group consisting of hydrogen and an acid solubilizing group and n is a whole number from 1 to 8 and contains at least one water-soluble 1:2-meta1

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Coloring (AREA)
US519521A 1962-11-27 1966-01-10 Process for coloring nitrogen-containing fibrous material Expired - Lifetime US3334960A (en)

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CH1391262A CH454082A (de) 1962-11-27 1962-11-27 Verfahren zum Färben und Bedrucken von stickstoffhaltigen Textilmaterialien

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US (1) US3334960A (enrdf_load_stackoverflow)
AT (1) AT249621B (enrdf_load_stackoverflow)
BE (1) BE640414A (enrdf_load_stackoverflow)
CH (1) CH454082A (enrdf_load_stackoverflow)
DE (1) DE1287554B (enrdf_load_stackoverflow)
ES (1) ES293882A1 (enrdf_load_stackoverflow)
FR (1) FR1383151A (enrdf_load_stackoverflow)
GB (1) GB997513A (enrdf_load_stackoverflow)
NL (1) NL300987A (enrdf_load_stackoverflow)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3442600A (en) * 1965-03-18 1969-05-06 Basf Ag Dyeing and printing fibers of natural and synthetic polyamides
US3630662A (en) * 1966-09-19 1971-12-28 Celanese Corp Process of dyeing shaped condensation polymer material in heated two-phase dye liquid
US3630659A (en) * 1967-01-14 1971-12-28 Bayer Ag Process for preventing damage to natural protein-containing fibers
US3765831A (en) * 1970-11-03 1973-10-16 Ugine Kuhlmann Treatment of polypeptide fibres
US3915634A (en) * 1973-04-24 1975-10-28 Pariser Ind Dyeing process
US4065257A (en) * 1972-02-25 1977-12-27 Ciba-Geigy Corporation Inhibition of dye staining during laundering of textile materials
EP0013369A1 (de) * 1978-12-29 1980-07-23 BASF Aktiengesellschaft Verfahren zum Färben von Narbenleder
US4309177A (en) * 1979-12-31 1982-01-05 The Boeing Company Method and solution for the room temperature dyeing of nylon
US4329146A (en) * 1971-11-09 1982-05-11 Ciba-Geigy Corporation Process for the dyeing of fibre material
US4568350A (en) * 1983-04-20 1986-02-04 Ciba-Geigy Corporation Cold pad-batch process for dyeing silk or silk-containing fiber blends with reactive dyes
US4717389A (en) * 1985-06-05 1988-01-05 Sandoz Ltd. Hair-reserving dyeing of wool- and fur-bearing skins
US4717390A (en) * 1985-01-30 1988-01-05 Sandoz Ltd. Method for dyeing leather with water-soluble sulpho group-containing sulphur dyes
EP0243788A3 (de) * 1986-04-26 1991-09-04 Bayer Ag Lederbehandlungsmittel

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CH524405A (de) * 1968-06-05 1972-01-31 Ici Ltd Verfahren zur kontinuierlichen farblichen Bemusterung von bahnförmig geführten textilen Substraten
GB1275739A (en) * 1968-09-04 1972-05-24 Iws Nominee Co Ltd Dyeing process
CH555441A (enrdf_load_stackoverflow) * 1969-03-10 1974-10-31
NL7004182A (enrdf_load_stackoverflow) * 1969-04-01 1970-10-05
DE2424303C3 (de) * 1974-05-18 1983-12-01 Hoechst Ag, 6230 Frankfurt Verfahren zum Färben von Polyamid- Teppichmaterial nach einem Klotz-Kaltverweil-Verfahren
DE2710152C2 (de) * 1977-03-09 1978-11-02 Bayer Ag, 5090 Leverkusen Färben von synthetischen Polyamiden
DE3539475A1 (de) * 1985-11-07 1987-05-14 Hoechst Ag Verfahren zum faerben von wollstueckware

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US2089212A (en) * 1936-06-08 1937-08-10 Kritchevsky Wolf Hydrotropic fatty material and method of making same
US2999731A (en) * 1958-09-15 1961-09-12 Woodlyn Corp Dyeing of normal wool
US3043650A (en) * 1962-07-10 Process for dyeing cellulose with
US3104931A (en) * 1958-03-11 1963-09-24 Ciba Geigy Corp Process for dyeing wool
US3208990A (en) * 1959-05-06 1965-09-28 Sandoz Ltd Metal-containing reactive azo chloropyrimidine dyestuffs
US3223470A (en) * 1961-05-06 1965-12-14 Hoechst Ag Process for the preparation of dyeings and prints which are fast to wet processing

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE832593C (de) * 1948-03-11 1952-02-25 Ciba A G Verfahren zum Faerben von tierischen Fasern
GB869150A (en) * 1958-10-08 1961-05-31 Ici Ltd New dyeing process

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3043650A (en) * 1962-07-10 Process for dyeing cellulose with
US2089212A (en) * 1936-06-08 1937-08-10 Kritchevsky Wolf Hydrotropic fatty material and method of making same
US3104931A (en) * 1958-03-11 1963-09-24 Ciba Geigy Corp Process for dyeing wool
US2999731A (en) * 1958-09-15 1961-09-12 Woodlyn Corp Dyeing of normal wool
US3208990A (en) * 1959-05-06 1965-09-28 Sandoz Ltd Metal-containing reactive azo chloropyrimidine dyestuffs
US3223470A (en) * 1961-05-06 1965-12-14 Hoechst Ag Process for the preparation of dyeings and prints which are fast to wet processing

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3442600A (en) * 1965-03-18 1969-05-06 Basf Ag Dyeing and printing fibers of natural and synthetic polyamides
US3630662A (en) * 1966-09-19 1971-12-28 Celanese Corp Process of dyeing shaped condensation polymer material in heated two-phase dye liquid
US3630659A (en) * 1967-01-14 1971-12-28 Bayer Ag Process for preventing damage to natural protein-containing fibers
US3765831A (en) * 1970-11-03 1973-10-16 Ugine Kuhlmann Treatment of polypeptide fibres
US4329146A (en) * 1971-11-09 1982-05-11 Ciba-Geigy Corporation Process for the dyeing of fibre material
US4065257A (en) * 1972-02-25 1977-12-27 Ciba-Geigy Corporation Inhibition of dye staining during laundering of textile materials
US3915634A (en) * 1973-04-24 1975-10-28 Pariser Ind Dyeing process
EP0013369A1 (de) * 1978-12-29 1980-07-23 BASF Aktiengesellschaft Verfahren zum Färben von Narbenleder
US4272243A (en) * 1978-12-29 1981-06-09 Basf Aktiengesellschaft Dyeing of grain leather
US4309177A (en) * 1979-12-31 1982-01-05 The Boeing Company Method and solution for the room temperature dyeing of nylon
US4568350A (en) * 1983-04-20 1986-02-04 Ciba-Geigy Corporation Cold pad-batch process for dyeing silk or silk-containing fiber blends with reactive dyes
US4717390A (en) * 1985-01-30 1988-01-05 Sandoz Ltd. Method for dyeing leather with water-soluble sulpho group-containing sulphur dyes
US4717389A (en) * 1985-06-05 1988-01-05 Sandoz Ltd. Hair-reserving dyeing of wool- and fur-bearing skins
EP0243788A3 (de) * 1986-04-26 1991-09-04 Bayer Ag Lederbehandlungsmittel

Also Published As

Publication number Publication date
BE640414A (enrdf_load_stackoverflow) 1964-05-26
DE1287554B (de) 1969-01-23
CH454082A (de) 1968-06-14
NL300987A (enrdf_load_stackoverflow)
AT249621B (de) 1966-09-26
GB997513A (en) 1965-07-07
ES293882A1 (es) 1964-04-01
CH1391262A4 (enrdf_load_stackoverflow) 1965-07-15
FR1383151A (fr) 1964-12-24

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