US3442600A - Dyeing and printing fibers of natural and synthetic polyamides - Google Patents

Dyeing and printing fibers of natural and synthetic polyamides Download PDF

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Publication number
US3442600A
US3442600A US533243A US3442600DA US3442600A US 3442600 A US3442600 A US 3442600A US 533243 A US533243 A US 533243A US 3442600D A US3442600D A US 3442600DA US 3442600 A US3442600 A US 3442600A
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parts
carbon atoms
mole
weight
dye
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US533243A
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Inventor
Manfred Daeuble
Klaus Dieck
Hans Heinrich
Heinz-Guenther Witsch
Dietmar Theilig
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BASF SE
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BASF SE
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Classifications

    • 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
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
    • 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

  • the present invention relates to a process for dyeing and printing fibers of natural and synthetic polyamides with anionic dyes.
  • polyamide fibers fibers of natural or synthetic polyamides (hereinafter called polyamide fibers), particularly those of wool, can be dyed or printed by applying to material containing these fibers an aqueous solution of an anionic dye at a temperature below that at which the dye will go onto the fibers and then finishing off the dyeing or print by steaming and/or introducing it into a hot acid liquor.
  • This method has serious disadvantages; for example it gives uneven dyeings.
  • Another object of the invention is to achieve uniform dyeings and prints by such a method in continuous operation.
  • Yet another object of the invention is to dye or print woolen fibers without damage.
  • polyamide fibers can be dyed and printed particularly advantageously by applying an aqueous solution which contains (a) at least one anionic dye and (b) at least one anion-active assistant to the fibers at a temperature which is lower than the absorption temperature of all the dyes present and finishing off the dyeing or the print by steaming and/ or introduction into a hot acid liquid (i.e.
  • the said aqueous dye solution also contains (0) at least one adduct of 2 to 8, preferably 3 to 6, moles of ethylene oxide to 1 mole of a linear or preferably branched primary, secondary or tertiary alcohol having six to eighteen, preferably six to fifteen, carbon atoms or an adduct of 2 to 6, preferably 2 to 4, moles of ethylene oxide to 1 mole of an alkylphenol having six to fifteen carbon atoms in the alkyl radical and (d) at least one adduct of 1 to 2 moles of ethylene oxide to 1 mole of a hydroxy compound of the benzene or naphthalene series which may? bear further low molecular weight nonionic radicals on the aromatic nucleus.
  • the anionic dyes to be used according to this invention may belong to any class of dyes, such as the azo, anthraquinone, phthalocyanine or nitro dyes. They may be for example 1:1 or 1:2 metal-complex dyes free from or containing sulfonic groups, chrome dyes which may be used together with agents yielding chromium, such as potassium dichromate, chromium fluoride or chromium acetate, or reactive dyes.
  • 'Anionic dyes in the present specification are defined as dyes which are described in the Colour Index (Second edition, 1956) as Acid Dyes, Mordant Dyes and Reactive Dyes.
  • Anion-active assistants are commonly used as additives in dyeing with anionic dyes.
  • Preferred agents of this type are water-soluble salts of sulfonic acids or sulfuric acid hemiesters which contain a hydrophobic grouping in the molecule, especially their salts with alkali metals, ammonium and particularly organic bases.
  • anion-active assistants are the water-soluble salts of aminobenzenesulfonic acids which bear hydrophobic radicals as substituents on the nitrogen, and of sulfosuccinic alkyl esters. It has proved to be particularly suitable to use at least 5 parts by weight of anion-active assistant (b) to each 1000 parts by weight of dye liquor or print paste. In other respects it is advantageous to adapt the amount of anion-active assistant to the amount of agent (c). If the latter is easily soluble in water or easily dispersable therein, a weight ratio of agent (b) to agent (c) of 0.25:1 to 05:1 is sufiicient.
  • the said ratio is advantageously increased, the upper limit being about 2:1. It is in fact possible to raise the amount of anionic agent even further but it is recommended, in the interests of economical operation not to use more than 60 parts by weight of agent (b) to 1000 parts by weight of liquor or paste.
  • Starting materials for products of the type specified under (c) may be alkylphenols, preferably p-alkylphenols, which contain a linear or branched alkyl radical having six to fifteen, preferably eight to ten, carbon atoms; they may also bear on the benzene nucleus low molecular weight alkyl radicals, such as methyl, ethyl, and propyl radicals, but monoalkyl phenols are preferred.
  • Other starting materials are linear or branched aliphatic alcohols which contain six to eighteen, preferably six to fifteen, carbon atoms.
  • Examples of these are: p-n-hexylphenol, p-n-octylphenol, p-i-nonylphenol, o-n-decylphenol, m-ndodecylphenol, n-hexanol, 2-ethylhexanol, isooctanol,
  • nonanols decanols, dodecanols, hexadecanols and octadecanols.
  • Mixtures of such starting materials such as are obtained by syntheses or by derivation from natural raw materials, are also suitable.
  • Branched-chain alcohols such as are obtainable for example from oligomers of propylene or butylene, such as trimeric propylene, tetrameric propylene, diisobutylene or triisobutylene, by oxo synthesis and hydrogenation, are particularly advantageous as start ing materials.
  • the agent (c) is used preferably in an amount of to 30 parts by weight to each 1000 parts by weight of dye liquor or print paste. Larger amounts may be used, but the economy of the process may suffer.
  • the adducts specified under (d) and derived from 1 to 2 moles of ethylene oxide and 1 mole of a hydroxy compound of the benzene or naphthalene series are monophenyl ethers or mononaphthyl ethers of ethylene glycol or diethylene glycol. They may bear as further low molecular weight nonionic radicals, particularly halogen atoms, preferably chlorine atoms, hydroxyl groups, low molecular weight aryl groups, in particular phenyl groups, alkyl groups having up to five carbon atoms and/or alkoxy groups having up to five carbon atoms, on the aromatic nucleus.
  • Examples are the reaction products of 1 to 2 moles of ethylene oxide with 1 mole of hydroxybenzene, 1-hydroxy-2-methylbenzene, 1-hydroxy-4-methylbenzene, 1 hydroxy 4 phenylbenzene, 1-hydroxy-2-methoxybenzene, l-hydroxynaphthalene, 2-hydroxynaphthalene, 1,2- dihydroxybenzene, 1,3-dihydroxybenzene, 1,4-dihydroxybenzene and 1,S-dihydroxynaphthalene. It is particularly advantageous to use the adduct of 1 mole of ethylene oxide to l-hydroxy-Z-chlorobenzene and to l-hydroxy-4- chlorobenzene.
  • the component (d) may be added to the liquor or paste preferably in an amount of 5 to 40 parts by weight with reference to 1000 parts by weight of liquor or paste. Whereas the efficacy of the agent gradually subsides below the preferred range, it is not deleterious to use larger amounts. The limits are determined by economic considerations.
  • the liquor or paste may also contain the conventional additives, as for example acids, such as acetic acid, swelling agents, such as benzyl alcohol, solubilizers, such as low molecular weight alcohols, glycols and butyrolactone, antifoaming agents, such as high molecular weight aliphatic alcohols, and thickeners. It is preferable, however, to use liquors which do not contain a thickener.
  • acids such as acetic acid
  • swelling agents such as benzyl alcohol
  • solubilizers such as low molecular weight alcohols, glycols and butyrolactone
  • antifoaming agents such as high molecular weight aliphatic alcohols
  • thickeners such as high molecular weight aliphatic alcohols
  • the mixture of assistants may be salted out by the addition of the agents supplying metal, for example chromium fluoride or chromium acetate; this causes separation into two layers and ineffectiveness of the system.
  • the agents supplying metal for example chromium fluoride or chromium acetate
  • chelate-forming agents as for example a-cyanocyclopentanone, p-diketo compounds or p-keto esters, such as acetylacetone, a-acetylbutrolactone, pentanone-Z-carboxylic esters or acetoacetic esters.
  • the complex-forming metal is thus bound and loses the property of salting out the assistant system from the solution. It is not necessary to bind the metal ions completely, but about 1 mole of the chelating agent to 1 mole of the metal salt used, for example chromium fluoride, is sufficient. It should however be taken into consideration that hydrogen ions are liberated by the chelate formation and contribute to the acidity of the liquor. Less acid is therefore required.
  • the salting-out action of the agents supplying metal on the assistant mixture may surprisingly also be suppressed 4 by using the dye, which is to react with the metal to form the complex, in dispersed form, the usual dye dispersing agents, such as alkali metal salts of ligninsulfonic acids or naphthalenesulfonic acid-formaldehyde reaction products, being coemployed.
  • the dye which is to react with the metal to form the complex, in dispersed form
  • the usual dye dispersing agents such as alkali metal salts of ligninsulfonic acids or naphthalenesulfonic acid-formaldehyde reaction products
  • finely divided dyes may be used brings with it the further advantage that even in the case of sparingly soluble chrome dyes, a colloidal solution may be obtained by scattering into warm water and this, after adding the assistants according to this invention and chromium salts, may be used immediately, whereas when dyes which are not finely divided are used, the suspension has to be boiled before the assistants and chromium salts are added and the remaining additives cannot be added until cooling has taken place.
  • the dye liquor to the material to be dyed may be carried out by printing, coating or spraying. It is preferable, however, to use the padding method.
  • the printing methods the vigoureux printing of tops has proved to be especially suitable.
  • the temperature is kept below that at which all the dyes present would be absorbed.
  • the absorption temperature is that at which the dye migrates from the aqueous dye solution to the material being dyed to an appreciable extent within the usual times of treatment; as used in the specification, the term absorption temperature means the temperature at which half of the dye originally present in the dye solution will migrate onto the material to be dyed within half an hour. It is advantageous to bring the dye liquor onto the material to be dyed at a temperature which is as much as possible below the absorption temperature; it has proved to be particularly suitable to use temperatures in the neighborhood of room temperature, i.e. at about 10 to 40 C.
  • Fixing of the dye may be carried out in the conventional way by treatment with steam at about to C.
  • Another known measure for fixing the dye is treatment in a hot acid liquor. It is advantageous to introduce the material impregnated with the dye liquor into the acid liquor at a temperature of 80 to 98 C. It has proved to be particularly suitable to subject the material to be dyed first to a short steam treatment in order that the dye may be partly fixed and then to complete fixation of the dye in the hot acid liquor.
  • Acids which are suitable for the acid liquor are inorganic and organic acids and also acid salts, examples being sulfuric acid, phosphoric acid, hydrochloric acid, formic acid, acetic acid, sodium hydrogen sulfate, potassium hydrogen sulfate and ammonium chloride.
  • the acids or acid salts are advantageously used in such an amount that the acid liquor has a pH value of 3 to 4.
  • Organic acids are preferred, particularly formic acid. In some cases it is useful to add water-soluble salts, preferably calcium salts, to the acid liquor.
  • the material may be washed, rinsed and dried in the usual way.
  • the process according to this invention may be carried out batchwise or continuously.
  • the process aucording to the invention is distinguished by the fact that the steps of the process can be varied to a great extent; moreover the possibility of working in the absence of thickeners is particularly valuable.
  • Thickeners may soil the apparatus used, for example the steamer, to such a degree that when the dye is changed it is necessary to carry out a cleaning of the apparatus lasting several hours.
  • a simple spraying out of the apparatus with water is suflicient to clean it.
  • polyamide fibers which may be dyed or printed according to the invention are wool and other animal hair, silk, protein fibers and synthetic polyamide fibers, such as those from e-caprolactam, from adipic acid and hexamethylene diamine and from w-aminoundecanic acid. They may be dyed or printed according to the invention alone as mixtures with each other or as mixtures with other fibers.
  • the present process is very well suited for dyeing tufted carpets of synthetic polyamide fibers. Whereas it has not been possible by prior art methods to dye these carpets continuously in a satisfactory manner, this is possible without difficulty by the process according to this invention; satisfactory dyeings are obtained even with 1:2 metalcomplex dyes, which tend to give very streaky dyeings on tufted goods.
  • Oxalkylatable compounds suitable as starting materials for these adducts are particularly aliphatic alcohols having ten to twenty carbon atoms, alkylphenols having ten to twenty carbon atoms, saturatedand unsaturated fatty acids having ten to twenty carbon atoms, their glycerides and their reaction products with alkanolamines and primary and secondary alkylamines having ten to twenty carbon atoms.
  • adducts examples include: the adduct of 40 moles of ethylene oxide to 1 mole of castor oil or to 1 mole of the reaction product of a fatty acid, such as oleic acid or stearic acid, with diethanolamine. Addition of 2 to 4 parts by weight of these products to 1000 parts by weight of an impregnating liquor is usually sufiicient.
  • the invention is illustrated by the following examples.
  • the parts are parts by weight.
  • EXAMPLE 1 30 parts of finely divided dye C.I. No. 15,675 is dissolved in 500 parts of water, then 20 parts of the triethanolamine salt of p-n-decylbenzenesulfonic acid, parts of the adduct of 6 moles of ethylene oxide to 1 mole of isodecanol, 10 parts of p-chlorophenyl monoethylene glycol ether (i.e. the adduct of 1 mole of ethylene'oxide to 1 mole of 1 hydroxy-4-chlorobenzene) and 15 parts of glacial acetic acid are added and the whole is made up to 1000 parts with water.
  • the triethanolamine salt of p-n-decylbenzenesulfonic acid parts of the adduct of 6 moles of ethylene oxide to 1 mole of isodecanol
  • 10 parts of p-chlorophenyl monoethylene glycol ether i.e. the adduct of 1 mole of ethylene'oxid
  • This padding liquor is used to impregnate wool tops at a temperature of 30 to 35 C.; the tops are then squeezed out to a liquor retention of about 110%.
  • the material is then steamed at 100 to 102 C. with saturated steam for fifteen minutes and then washed in warm water at about 40 to 45 C.
  • EXAMPLE 2 35 parts of the finely divided dye C.I, No. 15,710 is dissolved in 600 parts of water and then parts of the diethanolamine salt of p-n-dodecylbenzene sulfonic acid, 20 parts of the adduct of 4 moles of ethylene oxide to 1 mole of isononanol, 10 parts of p-chlorophenyl monoethylene glycol ether, parts of chromium fluoride and 20 parts of glacial acetic acid are added and the whole is made up to 1000 parts with water.
  • Wool tops are impregnated with this padding liquor, squeezed out and steamed in an atmosphere of saturated steam for forty-five minutes at 100 to 102 C. After the dyed material has been washed with water, a black dyeing is obtained which is fast to rubbing and exhibits no streaks.
  • Deep black dyeings which are fast to rubbing are similarly obtained by using the following compounds instead of the adduct of 4 moles of ethylene oxide to 1 mole of isononanoli (a) 15 parts of an adduct of 2 moles of ethylene oxide to 1 mole of p-isononylphenol;
  • EXAMPLE 3 30 parts of finely divided dye C.I. No. 15,675 is dissolved in 500 parts of water and then 20 parts of the sodium salt of the sulfuric acid hemiester of oleyl alcohol, 20 parts of the adduct of 4 moles of ethylene oxide to 1 mole of isononanol, 10 parts of p-chlorophenyl monoethylene glycol ether and 15 parts of glacial acetic acid are added and the whole is made up to 1000 parts with water. Wool tops are impregnated with this padding liquor, squeezed out and steamed for fifteen minutes at to 102 C. in an atmosphere of saturated steam.
  • a deep bluish red dyeing is obtained which is fast to rubbing and does not exhibit any streaks is obtained after washing.
  • EXAMPLE 4 20 parts of the finely divided dye C.I. No. 12,715 is dissolved in 500 parts of water and then 10 parts of triethanolammonium n-decylbenzene sulfonate, 12 parts of the adduct of 4 moles of ethylene oxide to 1 mole of isononanol,-5 parts of p-chlorophenyl monoethylene glycol ether, 10 parts of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil and 5 parts of glacial acetic acid are added and the whole is made up to 1000 parts with water.
  • Textured nylon-6 fibers tufted onto a jute fabric, are impregnated with the said solution, squeezed out with a. padding machine and steamed for twenty minutes at 100 to 102 C. in an atmosphere of saturated steam.
  • EXAMPLE 20 parts of dye C.I. No. 61,135 is dissolved in 500 parts of water and then 20 parts of the triethanolamine salt of n-decylbenzenesulfonic acid, 20 parts of the adduct of 6 moles of ethylene oxide to 1 mole of isodecanol, parts of p-chlorophenylmonoethylene glycol ether and 10 parts of glacial acetic acid are added and the whole is made up to 1000 parts with water.
  • a wool tufted carpet which has not yet been coated 1s impregnated with the said solution and squeezed out on a padding machine. It is then steamed for twenty minutes at 100 to 102 C. with saturated steam and washed with water. A greenish blue tufted material is obtained which exhibits very good levelness and penetration of the dye.
  • a process as claimed in claim 1 in which 2 to 4 parts by weight of an adduct of 10 to 80 moles of ethylene oxide to 1 mole of an aliphatic alcohol having ten to twenty carbon atoms, an alkylphenol having ten to twenty carbon atoms, a fatty acid having ten to twenty carbon atoms or a glyceride thereof or a reaction product thereof with an alkanolamine or an alkylamine having ten to twenty carbon atoms, is added to 1000 parts by weight of dye solution 4.
  • a process as claimed in claim 1 in which at least one adduct of 2 to 4 moles of ethylene oxide to 1 mole of an alkylphenol having eight to ten carbon atoms in the alkyl radical is used as component (0).

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  • Textile Engineering (AREA)
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US533243A 1965-03-18 1966-03-10 Dyeing and printing fibers of natural and synthetic polyamides Expired - Lifetime US3442600A (en)

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US (1) US3442600A (enrdf_load_stackoverflow)
AT (1) AT266765B (enrdf_load_stackoverflow)
BE (1) BE678060A (enrdf_load_stackoverflow)
CH (2) CH462102A (enrdf_load_stackoverflow)
DE (1) DE1469624A1 (enrdf_load_stackoverflow)
NL (1) NL6603511A (enrdf_load_stackoverflow)
SE (1) SE313038B (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3963432A (en) * 1972-10-27 1976-06-15 Imperial Chemical Industries Limited Aqueous compositions for use in applying dyestuffs

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3334960A (en) * 1962-11-27 1967-08-08 Ciba Ltd Process for coloring nitrogen-containing fibrous material
US3363972A (en) * 1963-01-25 1968-01-16 Ciba Ltd Process for dyeing and printing natural nitrogen-containing fibrous materials

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3334960A (en) * 1962-11-27 1967-08-08 Ciba Ltd Process for coloring nitrogen-containing fibrous material
US3363972A (en) * 1963-01-25 1968-01-16 Ciba Ltd Process for dyeing and printing natural nitrogen-containing fibrous materials

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3963432A (en) * 1972-10-27 1976-06-15 Imperial Chemical Industries Limited Aqueous compositions for use in applying dyestuffs

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AT266765B (de) 1968-11-25
DE1469624A1 (de) 1968-12-19
BE678060A (enrdf_load_stackoverflow) 1966-09-19
SE313038B (enrdf_load_stackoverflow) 1969-08-04
CH462102A (de) 1968-05-31
NL6603511A (enrdf_load_stackoverflow) 1966-09-19
CH457353A (de) 1968-06-15

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