US3929408A - Process for dyeing textile materials based on polyamide - Google Patents

Process for dyeing textile materials based on polyamide Download PDF

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Publication number
US3929408A
US3929408A US420975A US42097573A US3929408A US 3929408 A US3929408 A US 3929408A US 420975 A US420975 A US 420975A US 42097573 A US42097573 A US 42097573A US 3929408 A US3929408 A US 3929408A
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bath
dyeing
liter
temperature
accordance
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Georges Ravet
Jean-Bernard Chaux
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Soprosoie
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Soprosoie
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642Compounds containing nitrogen
    • D06P1/649Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6491(Thio)urea or (cyclic) derivatives
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/0096Multicolour dyeing
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/60General 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/60General 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
    • D06P1/607Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6076Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/60General 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
    • D06P1/613Polyethers without nitrogen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/62General 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 low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/621Compounds without nitrogen
    • D06P1/622Sulfonic acids or their salts
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/62General 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 low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/621Compounds without nitrogen
    • D06P1/622Sulfonic acids or their salts
    • D06P1/625Aromatic
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/62General 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 low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/628Compounds containing nitrogen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/96Dyeing characterised by a short bath ratio
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/924Polyamide fiber

Definitions

  • the present invention relates to dyeing of textiles and, more particularly, to a new process for dyeing textile articles made of polyamide in aqueous medium.
  • the invention produces polyamide textile articles having a perfectly homogeneous and uniform dyeing, free from significant stripe defects.
  • the process according to the invention relates very particularly to a substantial improvement of the productivity of the classical dyeing apparatus, for it permits a great increase of the quantity of textile materials to be dyed, a particularly appreciable reduction of the dyeing times and a decrease in the classically used dyeing temperature.
  • French Pat. No. l,l 85,750 discloses a process for dyeing polyamide textile materials at a temperature of at least 100C., in an acidified bath containing one or several suitable dyestuffs, an anionic leveling agent and a cationic weak complexing agent, which does not precipitate in the presence of the anionic components of the bath. This process allows one to obtain homogeneous dyeings, with good fastness, but such process does not ensure complete elimination of the stripe defect.
  • the process according to the present invention involves dyeing polyamide textile materials at suitable temperature and acidity, in an aqueous bath containing, in addition to the suitable dyestuff(s):
  • an organic sulfur-containing compound with a reducing action, which compound prevents a decrease of the mechanical qualities, a yellowing and/or a hardening of the textile material during the treatment;
  • a detergent and dispersing agent which agent avoids the separation or the flocculation of the bath, and promotes a better circulation of the bath through the textile material.
  • the present invention provides a synergistic effect so as to obtain, for the first time, an operation which not only provides an eminently satisfactorily dyed polyamide textile, but a process which is highly efficient from a cost standpoint.
  • the process utilizes a dyeing bath which contains in combination at least two anionic leveling agents, a cationic weak complexing agent, an organic sulfur-containing reducing compound, and a detergent and dispersing agent.
  • the group of anionic leveling agents comprises at least two components which possess the capability of temporarily fixing on the active dye sites of the textile materials, thus preventing the dyestuffs from too quickly taking up the sites which are ultimately meant for them.
  • the first anionic leveling agent B has the formula: R (A), R, in which R and R are sulfonated benzene or naphthalene rings the same or different; A is a radical selected from CH SO or NH; and n is an integer from to 4.
  • a preferred material is sodium or a di-naphthylmethane-B B disulfonate.
  • the second anionic leveling agent B is a salt of an organic acid of the alkyl-aryl-sulfonic type, or else a polyalkylaryl sulfonic acid salt, in which the aryl radical is a benzene or naphthalene ring, the neutralizing ion being selected from the group consisting of an alkali metal, NH ion or an amine, such as for instance ammonium dodecylbenzene sulfonate, or sodium tetrapropylbenzene sulfonate, etc.
  • the cationic weak complexing agent is generally a product resulting from the condensation of ethylene oxide on an aromatic amine or else on a long-chain fatty amine, such as for instance the stearylamine oxyethylated with 8 moles of ethylene oxide. Its function is to temporarily complex the dyestuffs in the dyeing bath, and thus the equilibrium of the complex must be capable of being destroyed by an increase in the bath temperature, and the freed dyestuffs can thus slowly replace the anionic leveling agents on the dye active sites of the textile materials.
  • the sulfur-containing organic compound which is known to be an active reducing agent in the treatments of polyamide textile articles, is preferably thio-urea or a derivative thereof with an N-alkyl substituted, such as N-mono-methyl thio-urea.
  • the sulfur-containing organic compound may be selected from known compounds for this purpose (e.g. French Pat. No. 1,313,937).
  • the detergent and dispersing agent which keeps the dyeing bath in a homogeneous state and makes easier the penetration and the circulation of the bath inside the textile materials during the treatment, is a mixture of C to C 'fatty alcohols,which are oxyethylated and sulfated, such as for instance ethoxylated and sulfated stearylic alcohol.
  • the various before-mentioned agents used in the process of the invention are introduced in the dyeing bath in proportions expressed in weight of dry material per volume unit of bath.
  • the anionic leveling agent belonging to the group B is introduced in a quantity from 0.10 g/liter to 1.50 g/liter of bath in such a way that the said agent is present in the bath in a proportion from 1.5 to 2 percent of the weight of textile materials to be dyed.
  • the proportions of the anionic leveling agent belonging to the group B may vary advantageously from 0.15 g/liter to 2 g/liter, but are preferably chosen from 0.25 g/liter to 0.50 g/liter of bath.
  • the cationic weak complexing agent is used in quantities varying from 0.10 g/liter to 1.50 g/liter of bath.
  • the sulfur-containing organic compound is used in very low quantities, varying from 0.0045 g/liter to 0.06 g/liter of bath, and the detergent and dispersing agent is added to the bath in quantities varying from 0.25 g/liter and l g/liter of bath.
  • the temperature during dyeing is at least 80C. and at most 130C. However, it is preferably between 85C. and 100C., i.e., at a temperature which remains, practically, considerably lower than the temperature recommended in the processes of the prior art. In addition to the fact that the dyeing temperature is lower, the
  • the acidic conditions of the bath are equally important. It is very easy, thanks to the present process, to adjust the acidity conditions according to the various stages of the increase of the bath temperature the pH is between 7 and 8 when the temperature is lower than C., then it is lowered to between 3 and 7 when the temperature reaches the adequate value for dyeing, that is to say when the temperature is preferably between 80C. and 100C.
  • the process according to the invention is advantageously carried on according to the following mode: After dissolution in water at room temperature of the various above-described agents, according to the preferred proportions, the resultant bath is introduced in the dyeing vat, which has been previously fitted with the textile materials.
  • the bath pH is then adjusted to a neutral or slightly basic value, either by introduction of an organic acid usually used, such as acetic acid, or by an alkaline agent normally used in this field.
  • the treatment of the textile begins at room temperature, then the bath is gradually heated at a rate of temperature increasing preferably between 05C. and 4C. per minute to the desired intermediate temperature, such as 40C. under normal pressure. It is during this first period of time that the temporary fixation of the anionic leveling agents on the dye active sites of the textile materials is carried out.
  • the dyestuffs which have been dissolved in a given quantity of water, are introduced into the bath in which the textile materials are residing.
  • the dyestuffs are then sequestered by the weak cationic complexing agent, which prevents them from ascending onto the textile materials quickly and in an irregular way.
  • the bath ratio can advantageously vary from l/4 to l/50 by volume.
  • the dyestuffs are selected from the conventional group consisting of simple acid dyestuffs and soluble or dispersed metalliferous dyestuffs normally used for dyeing polyamides.
  • the bath is then gradually heated from the intermediate temperature to the dyeing temperature of C.90C., according to a rate varying from 05C. to 4C. per minute, but preferably from 0.8C. to 12C. per minute. This dyeing temperature is then maintained for about 15 minutes.
  • the pH of the dyeing bath is then lowered to a value between 3 and 7 in acidity scale, by introducing any conventionally used acid, preferably an organic acid, in one bath, but preferably in several batches, the introduction time of the acid varying from 15 to 60 minutes according to the type of acidic dyestuffs used.
  • any conventionally used acid preferably an organic acid
  • the circulation of the dyeing bath is maintained for 15 to 60 minutes, then it is cooled and discharged, and the dyed textile materials are then washed.
  • the total duration of dyeing is established according to the degree of dyestuff exhaustion from the bath, this exhaustion being measured by the coloration of a sample taken out of the bath. Likewise the rate of the increase of the bath temperature can be determined with respect to samplings systematically achieved during dyeing, the colorations of which are evaluated by the colorimeter.
  • the process of dyeing according to the invention can be applied to continuous or discontinuous polyamide fibers in various forms such as flock, ribbons, finished clothes, cards, bobbins, hanks, fabrics and so on. It is equally carried out on woven, knitted, and non-woven textile materials, which are rolled on a perforated roller, enabling the circulation of the dyeing bath through such fabrics, or which are placed in bundles either in an apparatus for dyeing with circulation, or in a rotative perforated drum.
  • the process is normally applied to materials containing either all nylon fibers or sufficient nylon fibers with other fibers such that the problem of striping normally occurs.
  • the process for dyeing according to the invention can be effected in any vat commonly used and adapted to the textile materials to be dyed, fitted with the heating and cooling elements necessary for the various operation, as with the apparatus for control and thermal regulation.
  • the known apparatus can be mentioned drum machines, paddle machines, becks for fabrics or yarns, special machines for dyeing of textured jerseys, autoclaves, etc.
  • the dyeing was made in a three-color dyeing, and the used quantity of dyestuff was expressed in weight in relation to the polyamide weight.
  • the dyeing apparatus was an autoclave with a bath circulation by means of a pump.
  • the differential pressure of utilization was 2 bars, measuring the pressure drop during the passage of the dyeing bath through the fabric, and the bath ratio was 1/15 by volume.
  • Dyeing began at C. in the presence of the various agents as indicated below, then the bath was gradually heated 10 minutes to reach 40C; at this temperature the dyestuffs were introduced, and the bath pH was 7. Then the temperature was brought to 90C. after 60 minutes of further heating, kept at this value for 45 minutes, during which the pH of the dyeing bath was COMPARATIVE TEST l-l Tests of dyeing at a temperature lower than C. with only one anionic leveling agent, a cationic weak complexing agent and an organic sulfur-containing compound (leveling agent B and detergent and dispersant agent omitted).
  • the proportions of the various agents in the dyeing bath were the following:
  • first anionic leveling agent sodium dinaphthylmethane disulfonate
  • second anionic leveling agent ammonium dodecylbenzene sulfonate
  • cationic complexing agent stearylamine oxyethylated with 8 0.20 g/liter to moles of ethylene oxide
  • organic sulfur-containing compound thio-urea
  • the warp and weft polyamide 66 fabrics presented an excellent shade, as well as a very satisfactory level of shade, but there were numerous and significant stripes.
  • the warp and weft fabrics made of polyamide 66 showed an excellent shade, a perfect leveling, and the absence of the stripe defect was particularly noticeable.
  • the aqueous bath for dyeing contained the various agents according to the invention in the following proportions:
  • the fabric When it was out of the autoclave, the fabric had an excellent shade and a perfect level absorption and it was free from the main stripe defect.
  • a process for dyeing polyamide textile materials comprising:
  • said first anionic leveling agent is sodium a,a' dinaphthyl methane-6,3 disulfonate; said second anionic leveling agent is ammonium dodecylbenzene sulfonate or sodium tetrapropylbenzene sulfonate.
  • said second anionic leveling agent salt of an alkyl aryl sulfonic or polyalkyl aryl sulfonic acid has a neutralizing ion selected from the group consisting of the alkali metals, ammonium or an amine.
  • said cationic weak complexing agent is a condensation product of ethylene oxide on an aromatic amine or a long chain fatty amine.
  • a process according to claim 4 wherein said weak cationic complexing agent is stearyl amine oxyethylated with 8 moles of ethylene oxide.
  • said detergent and dispersing agent is an ethoxylated and sulfated mixture of fatty alcohols containing 8 to 20 carbon atoms.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US420975A 1972-12-06 1973-12-03 Process for dyeing textile materials based on polyamide Expired - Lifetime US3929408A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7244078A FR2209006B1 (ko) 1972-12-06 1972-12-06

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US3929408A true US3929408A (en) 1975-12-30

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US420975A Expired - Lifetime US3929408A (en) 1972-12-06 1973-12-03 Process for dyeing textile materials based on polyamide

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US (1) US3929408A (ko)
CH (2) CH560800A (ko)
FR (1) FR2209006B1 (ko)
GB (1) GB1446888A (ko)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4444563A (en) * 1981-09-07 1984-04-24 Ciba-Geigy Corporation Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials
US4631066A (en) * 1983-07-26 1986-12-23 Teijin Limited Method for improving light-resistance of aromatic polyamide fibers
US5427589A (en) * 1993-03-03 1995-06-27 Springs Industries, Inc. Method for dyeing fibrous materials
US5437690A (en) * 1994-05-25 1995-08-01 Springs Industries, Inc. Method for dyeing fibrous materials and dye assistant relating to the same
CN104404796A (zh) * 2014-11-15 2015-03-11 安徽宏祥丝绸织造有限公司 一种蚕丝染色方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2633615C3 (de) * 1976-07-27 1981-08-13 Bayer Ag, 5090 Leverkusen Verfahren zum Färben von synthetischen Polyamid-Fasermaterialien

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3232695A (en) * 1966-02-01 Process for dyetng materials based on polyamedes and composithons therefor
US3478376A (en) * 1965-10-16 1969-11-18 Basf Ag Dyeing and printing synthetic polyamide fibres

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1313937A (fr) * 1961-11-22 1963-01-04 Rhodiaceta Nouveau procédé de coloration des articles à base de polyamides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3232695A (en) * 1966-02-01 Process for dyetng materials based on polyamedes and composithons therefor
US3478376A (en) * 1965-10-16 1969-11-18 Basf Ag Dyeing and printing synthetic polyamide fibres

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4444563A (en) * 1981-09-07 1984-04-24 Ciba-Geigy Corporation Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials
US4631066A (en) * 1983-07-26 1986-12-23 Teijin Limited Method for improving light-resistance of aromatic polyamide fibers
US5427589A (en) * 1993-03-03 1995-06-27 Springs Industries, Inc. Method for dyeing fibrous materials
US5437690A (en) * 1994-05-25 1995-08-01 Springs Industries, Inc. Method for dyeing fibrous materials and dye assistant relating to the same
CN104404796A (zh) * 2014-11-15 2015-03-11 安徽宏祥丝绸织造有限公司 一种蚕丝染色方法

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Publication number Publication date
DE2360632A1 (de) 1974-07-04
CH560800A (ko) 1975-04-15
GB1446888A (en) 1976-08-18
DE2360632B2 (de) 1976-04-22
FR2209006A1 (ko) 1974-06-28
FR2209006B1 (ko) 1976-08-20
CH1663973A4 (ko) 1974-08-30

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