WO1994009201A1 - Procede de teinture d'un substrat dans un fluide surcritique - Google Patents

Procede de teinture d'un substrat dans un fluide surcritique Download PDF

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Publication number
WO1994009201A1
WO1994009201A1 PCT/DE1993/000943 DE9300943W WO9409201A1 WO 1994009201 A1 WO1994009201 A1 WO 1994009201A1 DE 9300943 W DE9300943 W DE 9300943W WO 9409201 A1 WO9409201 A1 WO 9409201A1
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WO
WIPO (PCT)
Prior art keywords
dye
fluid
additives
additive
free
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/DE1993/000943
Other languages
German (de)
English (en)
Inventor
Kurt Truckenmüller
Gottlob Wörner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Amann and Soehne GmbH and Co KG
Original Assignee
Amann and Soehne GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE4237823A external-priority patent/DE4237823A1/de
Application filed by Amann and Soehne GmbH and Co KG filed Critical Amann and Soehne GmbH and Co KG
Priority to EP93921794A priority Critical patent/EP0615561B1/fr
Priority to DE59302517T priority patent/DE59302517D1/de
Publication of WO1994009201A1 publication Critical patent/WO1994009201A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • D06P1/94—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 solvents which are in the supercritical state
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B19/00—Treatment of textile materials by liquids, gases or vapours, not provided for in groups D06B1/00 - D06B17/00
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B5/00—Forcing liquids, gases or vapours through textile materials to effect treatment, e.g. washing, dyeing, bleaching, sizing impregnating
    • D06B5/12—Forcing liquids, gases or vapours through textile materials to effect treatment, e.g. washing, dyeing, bleaching, sizing impregnating through materials of definite length
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/10—Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
    • D06M23/105—Processes in which the solvent is in a supercritical state
    • 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 method for dyeing a substrate in a supercritical fluid with the features of the preamble of patent claim 1.
  • a method with the features of the preamble of claim 1 is known from DE 39 06 724 AI.
  • textile substrates are dyed in a supercritical fluid, a preferred embodiment of this known method using dyes which consist exclusively of the actual color body and not the usual additives, such as e.g. Adjusting agents, dispersants and / or emulsifiers.
  • the known method has the disadvantage that such dyes, which only contain the powdery color body and in which the aforementioned additives (e.g. adjusting agents, dispersants, emulsifiers) are absent, can only be handled on a laboratory scale.
  • the additives mentioned above prevent the dye powder from being electrostatically charged, for example, so that such an electrostatically charged dye powder adheres everywhere as soon as the corresponding container is opened and thus leads to considerable malfunctions and incorrect production can result in dyeing.
  • the present invention has for its object to provide a method of the type specified that is applicable on an industrial scale without the difficulties mentioned above.
  • the process according to the invention is based on the basic idea that a conventional dye, provided with additives and thus a commercially available dye, is first selected, this conventional dye, however, being subjected to a separation before the substrate is dyed, such that at the separation, the additives and the additive-free dye (color body) are obtained separately.
  • the dye thus freed from the additives, which is the pure coloring body, is taken up in the process according to the invention either directly in the supercritical fluid used for the dyeing or in another liquid, so that it is taken up in the other liquid ⁇ Mene additive-free dye can then be used later for coloring the substrate in the supercritical fluid.
  • Mene additive-free dye can then be used later for coloring the substrate in the supercritical fluid.
  • the substrate to be colored is flowed through or flowed over with the supercritical fluid containing the pure color body.
  • the method according to the invention has a number of advantages.
  • any commercially available dye can be used in the process according to the invention, since the separation between the additives and the dye described above is brought about before the actual coloring, so that the process according to the invention is not limited to a few, at the time additive-free dyes obtainable only on a laboratory scale. Due to the fact that the method according to the invention uses commercially available dyes, the problems which are described at the beginning by way of example in connection with the powdery, additive-free dyes do not arise when using the method according to the invention.
  • a first embodiment of the method according to the invention provides that the additive-free dye is isolated after the additives have been separated off and the isolated dye is taken up directly in the other liquid to form a liquid-formed, additive-free dye, so that here too no additive-free dye powder is used as the end product occurs and thus the problems mentioned at the outset (dusting, electrostatic charging) do not occur in this embodiment of the method according to the invention.
  • the process according to the invention is used to select the other liquid in which the additive-free dye is taken up, ie preferably dissolved or dispersed.
  • Other liquids for additive-free dyes are, for example, water, acetone, alcohols (CL to C 4 alcohols) and / or chlorinated hydrocarbons, each in isolation or in a mixture, acetone, acetone-water mixtures (mixture ratio V : V about 9: 1) or ha- logenated hydrocarbons (chlorobenzene, methylene chloride) are used.
  • Disperse dyes there is also the possibility of making a slurry in water here and then breaking the dispersion that forms, for example by a sudden change in temperature and / or pH, so that additive-free dye agglomerates are formed from the disperse dye, which are then appropriately separated, for example by filtration and / or by centrifugation.
  • the additive-free dye isolated in this way is either taken up directly in the supercritical fluid used for the dyeing or the liquid-formed, additive-free dye is prepared by adding one of the abovementioned liquids, which is then storable and is used at a later time for dyeing .
  • the additives can just as well be removed from aqueous solutions of water-soluble dyes, such as reactive dyes, acid dyes or substantive dyes, by salting out the additive-free dye (dye body) by adding salts and the salted-out dye body directly in the abovementioned liquids records, so that a storable, liquid-form dye can later be used in the dyeing.
  • water-soluble dyes such as reactive dyes, acid dyes or substantive dyes
  • a particularly suitable embodiment of the process according to the invention provides that the additives are separated from the additive-free dye by extracting the conventional dye which contains the additives becomes.
  • the conventional dye used in each case the chemical structure of the additives contained therein and the chemical structure of the colored body, the selection of the fluid used for the extraction is based on this extraction.
  • the fluid can be selected in the extraction in such a way that either the additives or the additive-free dye (dye body) is dissolved out of the conventional dye, which then has the consequence that either the additives are in the extract and the dye body remains as the extraction residue or the coloring body is dissolved in the extract and the additives are in the extraction residue.
  • a first embodiment of the method according to the invention provides that a fluid is selected during the extraction which dissolves the additives from the conventional dye used.
  • the pure color body is obtained as an extraction residue, this method being particularly useful if the separated, additive-free dye is taken up immediately after the extraction for coloring the substrate in the supercritical fluid used for this purpose.
  • a preferred development of the previously described embodiment variant of the method according to the invention provides that the additives are extracted from the conventional dye with such a fluid that is subsequently used to dye the substrate.
  • This process variant of the process according to the invention then has the additional advantage that, owing to the identity of the fluids, the storage of further fluids can be dispensed with. Residues of the fluid used in the extraction of the additives, which may remain in the extraction residue then obtained after the extraction of the conventional dye, that is to say in the additive-free dye, may also remain, and the subsequent coloring do not bother.
  • it is not absolutely essential that the extraction with the fluid is carried out in the supercritical state, as will be required later for the dyeing of the substrate.
  • the extraction of the additives with the fluid in the non-supercritical state can also be carried out here, since a number of additives are readily soluble in a non-supercritical fluid, whereas the additive-free dye only becomes soluble in the same fluid in the supercritical state. This allows a particularly effective and rapid separation of the conventional dye into additives and additive-free dye, which is then obtained as a residue while the additives are in the fluid used.
  • such adsorbents or absorbents are used which contain the additives contained in the fluid, such as, for example, adjusting agents, oils, dispersants, emulsifiers or the like. , easy and unproblematic to remove, the preferred adsorbent or absorbent being silica gel, diatomaceous earth, aluminum oxide and / or activated carbon.
  • Another embodiment variant of the method according to the invention is based on the fact that a fluid is selected for the extraction which does not dissolve the additives from the conventional dye, as described above, but rather the additive-free dye.
  • the additive-free dye is obtained in the extract, so that such a dye can be isolated particularly easily and taken up in another liquid or stored directly as a liquid-formed, additive-free dye, so that such a liquid and additive-free dye no problems during later dyeing, for example no unwanted dusting.
  • a particularly suitable development of the previously described embodiment variant of the method according to the invention in which a fluid is selected for the extraction of the additive-free dye, which dissolves the additive-free dye, provides that an organic solvent is used here as the fluid.
  • the additive-free dye contained in the organic solvent after the extraction can then be stored as a liquid-formed, additive-free dye or isolated by evaporating the organic solvent used, so that the pure color body is solid.
  • This pure, additive-free dye body is then either taken up directly in the supercritical fluid used for dyeing or dissolved and / or dispersed in another liquid for later use to form an additive-free liquid dye.
  • the additive-free dye is also extracted by an organic solvent which dissolves the additive-free dye.
  • the additive-free dye is isolated from the organic solvent by absorbing and / or adsorbing the additive-free dye on an absorber or adsorber.
  • the pure color body absorbed or adsorbed in this way can then be added directly to the supercritical fluid used in the dyeing or the other liquid, the absorber or adsorber being recovered.
  • Another, particularly suitable embodiment of the method according to the invention provides that the extraction of the conventional dye is carried out with a fluid in the supercritical state.
  • this embodiment variant of the method according to the invention has the advantage that the extraction and thus the separation into additives and dye takes place within very short times, which is attributed to the fact that a supercritical fluid, due to its relatively low, corresponds to Gases of comparable viscosity penetrates the conventional dye to be extracted very well, which, depending on the fluid used, leads to an excellent and rapid dissolution of the additives or the additive-free dye.
  • a supercritical fluid has the advantage that it is particularly easy and quick to do so by increasing the temperature, increasing the volume or reducing the pressure into the corresponding one
  • Gas can be transferred so that, depending on the selection of the supercritical fluid used, the extracted, additive-free dye or the additives are obtained in solid or liquid form, while the gaseous fluid can be collected and used again.
  • the selection of the supercritical fluid used for the extraction in the method according to the invention is directed It depends on whether you want to extract the additives or the additive-free dye (color body). If, for example, polar additives, such as ionic dispersing or emulsifying agents, are to be extracted with the supercritical fluid, polar supercritical fluids such as ammonia, fluorochloroalkanes or mixtures of ammonia and / or fluorine Chloroalkanes with non-polar supercritical fluids, such as alkanes, carbon dioxide and / or carbon monoxide.
  • polar additives such as ionic dispersing or emulsifying agents
  • a non-polar, additive-free dye coloring body
  • alkanes in particular ethane, propane or pentane, carbon dioxide and / or carbon monoxide, are used alone or as a mixture as the supercritical extraction fluid.
  • a particularly advantageous development of the procedure described above, in which the conventional dye is extracted with a fluid and preferably a supercritical fluid, provides that a moderator is added to the fluid or the supercritical fluid during the extraction.
  • This moderator allows the dissolving behavior of the fluid or of the supercritical fluid to be matched to the constituent to be extracted (additives or dye free of additives) of the conventional dye, so that particularly fast extraction times result in particular polar compounds, such as preferably water, alcohols and / or salts, come into question.
  • the concentration of these moderators varies between about 1 vol. % and about 10 vol.%, preferably between about 2 vol.% and about 5 vol.%, based on the volume of the fluid used or the supercritical fluid used or the fluid mixture or the supercritical fluid mixture.
  • the dye component (additives or dye free of additives) obtained in the extract can be special are simply isolated so that a temperature increase, pressure reduction and / or volume increase is brought about.
  • the liquid or solid constituents (additives or dye free of additives) contained in the extract then arise, while the supercritical fluid used escapes as a gas, which is collected accordingly and possibly reused.
  • the conventional dye is extracted with other, non-supercritical fluids in the process according to the invention, then it is advisable to use a phase separation, liquid, to separate the dye components present in the extract after the extraction. liquid extraction, to remove ad- and / or absorption and / or filtration, so that the fluid free of additives or of additive-free dye can then be reused for further extraction.
  • the temperature which is used during the extraction in the method according to the invention generally depends on the fluid used in each case.
  • the extraction temperature usually varies between 10 ° C. and 240 ° C., preferably between 30 ° C. and 180 ° C.
  • the extraction temperature when using ethane as the extraction fluid is above 35 ° C., while the corresponding pressure is above 50 bar.
  • the extraction temperature is above 100 ° C. and the pressure during the extraction is above 42 bar, while with supercritical pentane at a temperature above 197 ° C.
  • the extraction time in the method according to the invention also depends on the conventional dye to be separated and the fluid used.
  • the extraction time usually varies between 2 minutes and 20 minutes, preferably between 5 minutes and 15 minutes.
  • any conventional dye can be used in the method according to the invention.
  • a disperse dye is selected as the conventional dye, since in the case of disperse dyes it is possible to separate the conventional dye particularly easily into additives and additive-free dyes (color bodies), in particular also by extraction. This is related to the fact that such disperse dyes are generally mixed with ionic dispersants / emulsifiers as additives, while the actual additive-free dye (coloring body) is non-polar.
  • the method according to the invention is also particularly suitable for dyeing textile substrates.
  • Textile substrates which can be dyed with dispersion dyes such as, in particular, textiles which are polyester fibers (polyethylene terephthalate), aliphatic or aromatic polyamide fibers (Kevlar, Nomex, polyamide ⁇ , polyamide ⁇ .6), polyimide fibers, polyalkylene fibers, can preferably be used here. in particular polyethylene fibers or polypropylene fibers, contain or consist of these fibers.
  • textile substrates such as preferably yarns, embroidery threads, sewing threads, fabrics or fabric parts, can be dyed perfectly within a very short time using the process according to the invention.
  • additives in the sense of the present application is understood to mean all substances which are present in a conventional dye and whose chemical composition is different from the actual dye, i.e. the
  • Color bodies differ.
  • adjusting agents, oils, dispersants and emulsifiers are included in this term.
  • dye in the present application includes not only a single dye but also a mixture of dyes, such a mixture of dyes, which generally consists of three to twelve dyes, is usually used in practice for dyeing .
  • the method according to the invention is explained in more detail below using an exemplary embodiment in conjunction with the drawing.
  • the single figure of the drawing shows a schematic view of an apparatus for performing the method according to the invention.
  • the apparatus shown schematically in the drawing has an autoclave 2 for receiving the textile substrate to be dyed, the autoclave 2 being connected via a ring line 6 to a circulation pump 4, so that the supercritical used for dyeing is pump 4 Fluid is conveyed and the supercritical fluid flows against or flows through the textile substrate arranged in the autoclave.
  • a further autoclave 1 is provided in a bypass line 7 to the ring line 6, the further autoclave serving to hold the dye or dye mixture used in the dyeing.
  • An expansion autoclave 3 is located in a further bypass line 8 or 9 to the ring line 6.
  • the apparatus has valves 11 to 18 which are arranged in the corresponding lines 5 to 10.
  • the valve 15 was opened, which caused the supercritical carbon dioxide to expand into the expansion vessel 3. After that, the valve 15 was closed. During the expansion, a milky liquid was obtained at the bottom of the expansion vessel 3 which, in addition to water, contained the additives extracted from the dye. This milky liquid was drained through the valve 18 designed as a lock. After the valve 18 was closed, further supercritical carbon dioxide was fed to the apparatus via the line 5 and the opened valve 17, this supercritical carbon dioxide being brought to a pressure of 190 bar and a temperature of 130 ° C.
  • this supercritical carbon dioxide was first of all via the bypass line 7 and the opened valves 14 and 13 pumped through the further autoclave 1 so that the additive-free dye remaining in the autoclave could be taken up in this supercritical carbon dioxide.
  • the valves 14 and 13 were then closed, with the result that the supercritical carbon dioxide loaded with additive-free dyes is now pumped via the ring line 6 and the opened valves 11 and 12 through the textile substrate arranged in the autoclave 2 was pumped.
  • the carbon dioxide in the reservoir 3 was introduced into the stream of supercritical fluid via the opened valve 16 and the line 9.
  • the supercritical carbon dioxide was discharged through a filter (not shown) and a corresponding drain valve, so that the colored substrate arranged in the autoclave could be removed from the autoclave. It was found here that the textile substrate, which was a 1 kg spool of thread, was uniformly colored.
  • the fastness to rubbing, the fastness to dry heat fixation and the fastness to washing were determined from the coloring. It was found that the corresponding grades were one grade better than the corresponding information provided by the dye manufacturer for an aqueous dyeing with the identical dye.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)

Abstract

Selon un procédé de teinture d'un substrat dans un fluide surcritique, un colorant exempt d'additifs est absorbé dans un fluide surcritique et on fait passer ledit fluide sur et/ou à travers le substrat à teindre. On sélectionne pour teindre un colorant usuel contenant des additifs, qui est séparé en additifs et en colorant exempt d'additifs avant la teinture du substrat. Le colorant exempt d'additifs ainsi séparé est ensuite directement absorbé par le fluide surcritique utilisé pour teindre ou par un autre liquide.
PCT/DE1993/000943 1992-10-08 1993-10-05 Procede de teinture d'un substrat dans un fluide surcritique Ceased WO1994009201A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP93921794A EP0615561B1 (fr) 1992-10-08 1993-10-05 Procede de teinture d'un substrat dans un fluide surcritique
DE59302517T DE59302517D1 (de) 1992-10-08 1993-10-05 Verfahren zum färben eines substrates in einem überkritischen fluid

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEP4233659.7 1992-10-08
DE4233659 1992-10-08
DEP4237823.0 1992-11-10
DE4237823A DE4237823A1 (de) 1992-10-08 1992-11-10 Verfahren zum Färben eines Substrates in einem überkritischen Fluid

Publications (1)

Publication Number Publication Date
WO1994009201A1 true WO1994009201A1 (fr) 1994-04-28

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PCT/DE1993/000943 Ceased WO1994009201A1 (fr) 1992-10-08 1993-10-05 Procede de teinture d'un substrat dans un fluide surcritique

Country Status (4)

Country Link
EP (1) EP0615561B1 (fr)
AT (1) ATE137821T1 (fr)
ES (1) ES2087770T3 (fr)
WO (1) WO1994009201A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0846803A3 (fr) * 1996-12-04 1998-08-19 Amann & Söhne GmbH & Co. Procédé de teinture de matériaux textiles
US5938794A (en) * 1996-12-04 1999-08-17 Amann & Sohne Gmbh & Co. Method for the dyeing of yarn from a supercritical fluid
US6048369A (en) * 1998-06-03 2000-04-11 North Carolina State University Method of dyeing hydrophobic textile fibers with colorant materials in supercritical fluid carbon dioxide
US6261326B1 (en) 2000-01-13 2001-07-17 North Carolina State University Method for introducing dyes and other chemicals into a textile treatment system
US6676710B2 (en) 2000-10-18 2004-01-13 North Carolina State University Process for treating textile substrates
US10550513B2 (en) 2017-06-22 2020-02-04 Hbi Branded Apparel Enterprises, Llc Fabric treatment compositions and methods

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3906724A1 (de) * 1989-03-03 1990-09-13 Deutsches Textilforschzentrum Faerbeverfahren
WO1993014259A1 (fr) * 1992-01-09 1993-07-22 Jasper Gmbh Procede d'application de substances sur des materiaux fibreux et sur des substrats textiles
WO1993018221A2 (fr) * 1992-03-05 1993-09-16 Jasper Gmbh Procede et dispositif pour traiter des substrats textiles dans des fluides surcritiques

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3906724A1 (de) * 1989-03-03 1990-09-13 Deutsches Textilforschzentrum Faerbeverfahren
WO1993014259A1 (fr) * 1992-01-09 1993-07-22 Jasper Gmbh Procede d'application de substances sur des materiaux fibreux et sur des substrats textiles
WO1993018221A2 (fr) * 1992-03-05 1993-09-16 Jasper Gmbh Procede et dispositif pour traiter des substrats textiles dans des fluides surcritiques

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0846803A3 (fr) * 1996-12-04 1998-08-19 Amann & Söhne GmbH & Co. Procédé de teinture de matériaux textiles
US5938794A (en) * 1996-12-04 1999-08-17 Amann & Sohne Gmbh & Co. Method for the dyeing of yarn from a supercritical fluid
US6048369A (en) * 1998-06-03 2000-04-11 North Carolina State University Method of dyeing hydrophobic textile fibers with colorant materials in supercritical fluid carbon dioxide
US6261326B1 (en) 2000-01-13 2001-07-17 North Carolina State University Method for introducing dyes and other chemicals into a textile treatment system
US6615620B2 (en) 2000-01-13 2003-09-09 North Carolina State University Method for introducing dyes and other chemicals into a textile treatment system
US6676710B2 (en) 2000-10-18 2004-01-13 North Carolina State University Process for treating textile substrates
US10550513B2 (en) 2017-06-22 2020-02-04 Hbi Branded Apparel Enterprises, Llc Fabric treatment compositions and methods

Also Published As

Publication number Publication date
ATE137821T1 (de) 1996-05-15
EP0615561A1 (fr) 1994-09-21
ES2087770T3 (es) 1996-07-16
EP0615561B1 (fr) 1996-05-08

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