US3814579A - Process for one-bath dyeing and printing of textile material - Google Patents

Process for one-bath dyeing and printing of textile material Download PDF

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Publication number
US3814579A
US3814579A US00289748A US28974872A US3814579A US 3814579 A US3814579 A US 3814579A US 00289748 A US00289748 A US 00289748A US 28974872 A US28974872 A US 28974872A US 3814579 A US3814579 A US 3814579A
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Prior art keywords
dyeing
dyestuffs
printing
water
fibers
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Expired - Lifetime
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US00289748A
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English (en)
Inventor
F Meininger
P Mischke
W Birke
Der Eltz H Von
F Schon
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Hoechst AG
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Hoechst AG
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Priority claimed from DE19712146762 external-priority patent/DE2146762C3/de
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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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6428—Compounds containing aminoxide groups
    • 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
    • D06P1/667—Organo-phosphorus compounds
    • 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
    • D06P1/922—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 hydrocarbons

Definitions

  • the present invention relates to a process for the onebath dyeing and printing of textile material.
  • This invention now relates to the one-bath dyeing and printing of textile material made from synthetic or natural fibers or blends of such fibers with suitable dyestuffs according to a continuous or semi-continuous padding or printing method, which comprises applying to the material a padding liquor or a printing paste containing an organic solvent, one or more organic dyestuffs, if required a chemical agent for the fixation of these dyestuffs, Water and a phosphine oxide of the general formula 1) and/or an amine oxide of the general formula (2) 0 R1 0 R1 R-i Riq in' which R, R and R each stands for an unbranched or branched alkyl or alkenyl group of 1 to 18 carbon atoms, which may be substituted by hydroxy, cyano or amino groups or by halogen atoms and which may be interrupted by oxygen, sulfur and/or nitrogen atoms and/or by a carbonyloxy, carbamoyl or sulfamoyl group, and the radicals R and R
  • the instant process differs from methods known in this field in that the dyeing media consisting of mixtures of water with organic solvents also contain phosphine oxides and/or amine oxides of .the above-mentioned chemical constitution specified by the formulae given above, which have polyfunctional properties that exert a favorable influence on the dyeing and printing operations of the invention as well as on the dyed products resulting therefrom:
  • the above-cited phosphine oxides and/or amine oxides may be used to prepare dyeing liquors which, depending on the solvent used and on the amounts of product and water employed, provide clear solutions or emulsions or emulsified dispersions of low, medium or high viscosity. Seen from a practical point of view, this effect of the substances both as emulsifiers and as thickeners means that the problems that occur in dyeing because of material and machinery, can be overcome also by an addition of these products.
  • the solubilizing effect of the products also allows the process of the invention to use such dyestuffs in a dissolved form which are usually considered insoluble as well in the organic solvent used as in water.
  • the dye stuff preparation is applied to the textile material, preferably by pad-dyeing, but also by spraying, doctoring and other techniques that assure a continuous operation, for example printing.
  • the pad-dyeing operation is generally performed at room temperature but it may also be carried out at any lower or higher temperature ranging from the freezing point to the boiling point of the solvent mixture used or of the azeotropic mixture that may result therefrom. If, however, high-viscosity dyeing liquors are to be used, for example to prevent migration, the temperature applied should be about room temperature, or a laboratory test should previously be made to determine the maximum temperature at which the thickened emulsion is still stable.
  • the dyeings or prints are subjected to a suitable fixation method which depends on the dyestuffs used.
  • the material which has been padded or printed with the dyestuif preparation may be subjected immediately afterwards in moist state to a steaming or pressure-steaming process, optionally using superheated steam or solvent vapor (one-bath pad Wet-steaming process). It is also possible to steam under the conditions mentioned above the pad-dyeings or prints'after an intermediate drying operation at relatively low temperatures of up to a maximum of C. (one-bath pad steam process) or to thermosol them on a tenter frame or a perforated drum drier by sucking dry hot air through them or by means of contact heat (thermofixation process).
  • the favorable conditions of one-bath dyeing are preserved by batching up the textile articles, which have been padded or printed with the dyestuif preparation, and allowing the fibrous material to dwell in moist state on a skein at room temperature or at a moderately elevated temperature of from 30 to 60 C. for 2 to 24 hours, preferably for 4 to 14 hours (one-bath pad-batch or pad short-dwell process).
  • This semi-continuous technique is characterized by a high economy of operation, due to the saving of energy, and does not require expensive intermediate-drying and fixing apparatuses.
  • fixation may be followed by an after-cleaning operation, for which the phosphine oxides and/or amine oxides mentioned may also be used in the aqueous or solvent-containing after-treatment liquor.
  • the process of the present invention is suitable for the continuous or semi-continuous dyeing and printing of various fiber types of synthetic or natural origin, for example of woven or knit fabrics, combed material, cables and nonwovens (fleeces) made of polyester, polyamide, polyurethane, polyacrylonitrile, cellulose-2 /2-acetate, cellulose-triacetate, polyvinyl chloride, polyvinyl alcohol, polypropylene or cellulose fibers or wool or of blended materials of these fibers.
  • organic solvents suitable for the process of the invention there are especially used hydrocarbons and, in particular, halogenated, especially chlorinated, hydrocarbons, particularly perchloroethylene (tetrachloroethylene), trichloroethylene, trichloroethane, tetrachloroethane, methylene chloride, chloroform, carbon tetrachloride, fluorotrichloromethane or trifiuorotrichloroethane.
  • benzene, chlorobenzene, cyclohexane or gasolines as well as mixtures thereof which may boil while forming azeotropic mixtures.
  • the mixing ratio of organic solvent to water in the dyeing liquors and printing pastes ranges from 1-99, preferably 30-98% by volume of organic solvent to 99-1, preferably 702% by volume of water.
  • the phosphine oxides and amine oxides are used, according to the invention, either as such or in mixture with each other in amounts of from 1 to 100 g./l., preferably from 3 to 60 g./l., calculated on the mixture of organic solvent and water.
  • the phosphine oxides or amine oxides mentioned under formulae (1) and (2) or mixtures of these products are first dissolved in an organic solvent, preferably at room temperature.
  • an organic solvent preferably at room temperature.
  • water-insoluble dyestufls for example of the disperse dyestuff type, may also be dissolved in this solution.
  • This dyestuff type comprises not only dyestuifs which have a good solubility in theorganic solvent used without an addition of the adjuvants of the invention but also a large number of dyestuffs which are usually not, or only sparingly, soluble in the organic solvent used but can be solubilized or substantially improved in their solubility using the cited products offormulae (1) and (2).
  • water-soluble dyestufls are dissolved in the water portion of the padding liquor or water-insoluble dye-stuffs are also dispersed therein at a temperature of from room temperature to 0., preferably from 40 to 60 C.
  • This aqueous solution or dispersion is then slowly added while stirring to the solution of the phosphine oxides and/or amine oxides and, where required, of dyestuffs, in an organic solvent.
  • the results are from clear solutions up to low-viscosity and high-viscosity emulsions or emulsified dispersions.
  • the process of the invention is practically suitable for any dyestuff class which can also be applied from an aqueous liquor, for example disperse dyestuffs, vat dye stuffs, reactive dyestuffs, acid dyestuffs, metal complex dyestuffs, chroming dyestuffs, substantive dyestuffs, leuco esters of vat dyestuffs, cationic dyestuffs, developing dye stuffs and the like.
  • EXAMPLE 1 50 g. of decyl-dimethyl-phosphine oxide were dissolved in 810 ml. of perchloroethylene at about 25 C.
  • a second solution of 2.7 g. of the dyestulf fSolubilized Vat Violet 2, C.I.-No. 73386, in ml. of Water was prepared at about 90 C.
  • This second aqueous solution was then slowly added while continuously stirring to the perchloroethylene solution and the mixture was stirred until it had cooled to room temperature, whereupon a rather viscous emulsion was obtained.
  • 0.9 g. of ammonium sulfate and 0.6 g. of sodium formiate were dissolved in 30 ml. of water at room temperature and the solution was also added while stirring to the emulsion that had been prepared previously.
  • a blended fabric made of 67% of polyester fibers and 33% of cotton was padded with the liquor thus prepared on a padding machine with a squeezing effect of about 90%, calculated on the weight of the dry material, and then dried.
  • the dyestutf was then fixed on the textile material by a dry-heat treatment at 210 C. which took 60 seconds. A red-violet dyeing was obtained on both fiber types of the blended fabric.
  • EXAMPLE 2 Agreen dyeing was obtained by treating a blended fabric made of 55 parts of polyester fibers and 45 parts of wool, under the application conditions of Example 1, with a padding liquor containing, in addition to the same composition of'perchloroethylene, water, ammonium sulfate and sodium formiate' as above, the same amount by weight of the compound Solubilized Vat Green 1, C.I.- No. 59826, as a dyestuif, 36 g. of coco fatty acid-dimethylamine oxide and 3.5 g. of sodium chlorate.
  • the padded material was thermosoled for 1 minute at 185 C.
  • EXAMPLE 3 25 g. of decyl-dimethyl-phosphine oxide were dissolved at room temperature in 820 ml. of perchloroethylene. Moreover, 7 g. of the dyestulf Basic Blue 3, C.I.-No. 51005, were dissolved in 180 ml. of water at about 70 C. After having cooled, the aqueous solution was slowly added while stirring to the perchloroethylene solution, whereupon a viscous emulsion was obtained.
  • a fabric made of polyacrylonitrile fibers was then padded on a padding machine with the dyeing liquor thus prepared. After having been dried, the material was steamed for about 30 minutes under a pressure of about 1 atmosphere gauge for the fixation of the dyestuif. A blue dyeing was obtained.
  • a similar tinctorial result could be obtained using, instead of the afore-mentioned textile material, a fabric made of acid-modified polyester fibers.
  • EXAMPLE 4 4 g. of the 1:2-chromium complex compound of the dyestutf of the formula (a) a fabric made of polyamide-6,6 fibers, (b) a fabric made of wool and (c) a combed material made of polypropylene fibers.
  • the three fiber types were steamed for about 40 minutes at 100-101" C. to fix the dyestuif. In all three cases, grey dyeings were obtained on each of the substrates.
  • EXAMPLE 5 52g. of decyl-dimethyl-phosphine oxide were dissolved at room temperature in 800 ml. of perchloroethylene. Moreover, a solution of 4 g. of the dyestulf Direct Yellow 8, C.I.-No. 13920, in 200 ml. of water was prepared at 80 C. This second solution was then added while stirring to the perchloroethylene solution and the mixture was further stirred for some time, until cooled to room temperature.
  • the viscous emulsion thus obtained was then used to pad (a) a fabric made of cotton, (b) a fabric made of polyamide-6 fibers an (c) a fabric made of cellulose-2 At-acetate fibers fl; I
  • EXAMPLE 7 45 g. of decyl-dimethyl-phosphine oxide were mixed with 7 g. of the dyestutf Disperse Orange 13," C.I.-No. 26080, and the mixture was dissolved at about 25 C. in 770 ml. of perchloroethylene. Moreover, 4 g. of the dyestutf Reactive Blue 19, C.I.-No. 61200, were separately dissolved at about 90 C. in 180 ml. of water. This aqueous solution was then slowly added while stirring to the perchloroethylene solution and the mixture was further stirred until cooled to about 25 C. Subsequently, 50 ml. of an aqueous solution containing 50 g. of sodium bicarbonate per liter were also added to the dyebath.
  • a blended fabric made of 67% of polyester fibers and 33% of cotton was padded on a padding machine with the liquor prepared in this manner, then dried and thermosoled for 1 minute at 210 C.
  • a bicolor dyeing was obtained on the blended fabric: an orange color on the polyester fiber portion and a blue color on the cellulosic fiber portion.
  • EXAMPLE 8 60 g. of decyl-dimethyl-phosphine oxide were dissolved in 920 ml. of benzene at room temperature. To this solution, ml. of an aqueous dyestutf solution containing, per liter, 30 g. of the dyestuff Basic Violet 2, C.I.-No. 42520, were slowly added while stirring.
  • a combed material made of polyacrylonitrile fibers was padded on a paddingmachine with the solution thus obtained, then dried and steamed for 30 minutes at 100- 101 C. A red-violet dyeing was obtained.
  • EXAMPLE 9 55 g. of decyl-dimethyl-phosphine oxide were dissolved at about 25 C. in 985 ml. of perchloroethylene. To this solution, 15 ml. of Water which was heated to about 60 C. and in which 0.5 g. of the dyestulf Basic Blue 3,? C.I.-No. 51005 was dissolved, were slowly added while stirring. f
  • a fabric made of acid-modified polyester 'fibers was padded on a padding machine with the solution thus prepared, and was dried.
  • the dyestuff was fixed by means of a dry-heat treatment at 210 C. within 1 minute. A light blue dyeing was obtained.
  • a fabric made of"67% of polyester fibers and 33 of cotton was padded on a padding machine with the liquor obtained, dried and thermosoledfor 1 minute at 215 C. A yellow dyeing was obtained on the two components of the blended fabric.
  • a fabric made of polyamide-6 fibers was padded on a padding machine with the emulsion thus obtained, dried and steamed for about 20 minutes at a pressure of about 1 atmosphere gauge. A red dyeing was obtained.
  • EXAMPLE 12 30 g. of decyl-dimethyl-phosphine oxide were dissolved at room temperature in 750 ml. of perchloroethylene. Moreover, a solution of g. of the dyestuif Reactive Yellow 17, C.I.-No. 18852, in 200 ml. of water was prepared at about 80 C. This aqueous dyestulf solution was then slowly added While stirring to the perchloroethylene solution and the mixture was further stirred until cooled to 25 C. Subsequently, 50 ml. of a 4% sodium hydroxide solution were also added to the dyebath.
  • a cotton fabric was then padded on a padding machine with the liquor thus prepared and the moisture excess was squeezed 01f.
  • the padded material was then batched up, wrapped with a plastic foil and allowed to dwell at this state for 4 hours at room temperature, in order to fix the dyestuif.
  • an after-washing operation usual for dyeings produced with reactive dyestuffs, using non-ionic detergents a yellow dyeing on cotton was obtained.
  • a process for the one-bath dyeing and printing of textile material made of synthetic or natural fibers or mixtures of such fibers, with appropriate dyestuffs according to a continuous 'or semi-continuous pad-dyeing or printing method which comprises applying to the material a padding liquor or a printing paste containing an organic solvent, one or more organic dyestuffs, if required a chemical agent for the fixation of these dyestulfs, water and a phosphine oxide of the general formula (1) or an amine oxide of the general formula (2) 2 R1 g/Rl R-P R-N in which R, R and R each is unbranched or branched alkyl or alkenyl of 1 to 18 carbon atoms, which may be substituted by hydroxy, cyano or amino or halogen and which may be interrupted by oxygen, sulfur and/ or nitrogen and/ or by carbonyloxy, carbamoyl or sulfamoyl, and the radicals R and R may constitute together with the central phosphorus or nitrogen
  • phosphine oxides areselected from the group consisting of octyl-dimethyl-phosphine oxide, octyl-diethyl-phosphine oxide, decyl-riimethyl-phosphine oxide, decyl-methylbutyl-phosphine oxide, dodecyl-dimethyl-phosphine oxide,
  • dodecyl-diethyl-phosphine oxide 'y-palmitic acid-amidemethyl-dimethyl-phosphine oxide, -palmitic' acid-amido propyl dimethyl phosphine oxide,hexyl-methyl-butylphosphine oxide and mixtures thereof.
  • amine oxides are selected from the group consisting of octyldimethyl-amine oxide, N dodecyl piperidine- N-oxide, tetra-decyl dimethyl amine oxide, coco-fatty 'acid-di methyl-amine oxide, oleoyl-arnidomethyl-dimethyl-amine oxide or hexadecylbis-(fl-hydroxy-ethyD-amine oxide and mixtures thereof.
  • said or ganic solvent is an optionally halogenated aliphatic or aromatic hydrocarbon.
  • organicv solvent is selected from the group consisting of trichloroethylene, tetrachloroethylene (perchloroethylene), trichloroethane, cloroform, carbon tetrachloride, fluorotrichloromethane and triiluoro-trichloroethane.
  • the organic dyestuif is selected from the group consisting of a disperse dyestuif, a vat dyestuff, a reactive dyestulf, an acid dyestufi, a metal complex dyestuff, a chroming dyestuif, a substantive dyestuff, a leuco-ester of a vat dyestuif, a cationic dyestutf and a developing dyestuff.
  • the organic dyestuif is selected from the group consisting of a disperse dyestuif, a vat dyestuff, a reactive dyestulf, an acid dyestufi, a metal complex dyestuff, a chroming dyestuif, a substantive dyestuff, a leuco-ester of a vat dyestuif, a cationic dyestutf and a developing dyestuff.
  • the textile material is selected from the group consisting of awoven or knitted fabric, a combed material, a cable or a non woven article made of polyester, polyamide, polyure thane, polyacrylonitrile, cellulose-2 /2-acetate, cellulose? triacetate, polyvinyl chloride, polyvinyl alcohol, polypropylene, cellulose fibers, wool and blends of such fibrous materials.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US00289748A 1971-09-18 1972-09-15 Process for one-bath dyeing and printing of textile material Expired - Lifetime US3814579A (en)

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Application Number Priority Date Filing Date Title
DE19712146762 DE2146762C3 (de) 1971-09-18 Verfahren zum einbadigen Färben und Bedrucken von Textilmaterialien

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US3814579A true US3814579A (en) 1974-06-04

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US (1) US3814579A (enrdf_load_stackoverflow)
JP (1) JPS4839777A (enrdf_load_stackoverflow)
AT (1) AT336538B (enrdf_load_stackoverflow)
BE (1) BE788959A (enrdf_load_stackoverflow)
CA (1) CA982756A (enrdf_load_stackoverflow)
CH (1) CH1349572A4 (enrdf_load_stackoverflow)
FR (1) FR2153094B1 (enrdf_load_stackoverflow)
GB (1) GB1411639A (enrdf_load_stackoverflow)
IT (1) IT967561B (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3951591A (en) * 1972-10-24 1976-04-20 Hoechst Aktiengesellschaft Process for dyeing synthetic fiber materials
US9718080B1 (en) 2016-05-06 2017-08-01 RADCO Infusion Technologies, LLC Linear substrate infusion compartment
US11098445B2 (en) 2016-05-06 2021-08-24 Anderson Group, Ltd. Continuous linear substrate infusion

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4539161A (en) * 1980-07-25 1985-09-03 Ciba-Geigy Corporation Amine oxide compounds

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3951591A (en) * 1972-10-24 1976-04-20 Hoechst Aktiengesellschaft Process for dyeing synthetic fiber materials
US9718080B1 (en) 2016-05-06 2017-08-01 RADCO Infusion Technologies, LLC Linear substrate infusion compartment
US11033923B2 (en) 2016-05-06 2021-06-15 RADCO Infusion Technologies, LLC Linear substrate processing compartment
US11098445B2 (en) 2016-05-06 2021-08-24 Anderson Group, Ltd. Continuous linear substrate infusion
US11298719B2 (en) 2016-05-06 2022-04-12 Southwire Company, Llc Device for modifying a linear substrate
US11359332B2 (en) 2016-05-06 2022-06-14 Anderson Group, Ltd. Continuous linear substrate infusion
US12097527B2 (en) 2016-05-06 2024-09-24 Southwire Company, Llc Device for modifying a linear substrate
US12103035B2 (en) 2016-05-06 2024-10-01 Southwire Company, Llc Device for modifying a linear substrate

Also Published As

Publication number Publication date
GB1411639A (en) 1975-10-29
AT336538B (de) 1977-05-10
FR2153094B1 (enrdf_load_stackoverflow) 1978-02-10
IT967561B (it) 1974-03-11
FR2153094A1 (enrdf_load_stackoverflow) 1973-04-27
DE2146762A1 (de) 1973-04-05
CH1349572A4 (de) 1975-06-30
ATA792372A (de) 1976-09-15
CA982756A (en) 1976-02-03
DE2146762B2 (de) 1976-05-26
JPS4839777A (enrdf_load_stackoverflow) 1973-06-11
BE788959A (fr) 1973-03-19

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