US3843322A - Dyestuff solution for acrylic fibers - Google Patents

Dyestuff solution for acrylic fibers Download PDF

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Publication number
US3843322A
US3843322A US00100536A US10053670A US3843322A US 3843322 A US3843322 A US 3843322A US 00100536 A US00100536 A US 00100536A US 10053670 A US10053670 A US 10053670A US 3843322 A US3843322 A US 3843322A
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present
complex
solution
solvent
dyestuff
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US00100536A
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English (en)
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C Streck
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GAF Corp
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GAF Corp
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Priority to US00100536A priority Critical patent/US3843322A/en
Priority to FR7145217A priority patent/FR2118924B1/fr
Priority to IT32648/71A priority patent/IT944175B/it
Priority to CA130,591A priority patent/CA964006A/en
Priority to CH1860471A priority patent/CH561817A/xx
Priority to GB5920971A priority patent/GB1361439A/en
Priority to DE19712163427 priority patent/DE2163427A1/de
Priority to BE777024A priority patent/BE777024A/xx
Priority to NL7117602A priority patent/NL7117602A/xx
Priority to CH1860471D priority patent/CH1860471A4/xx
Application granted granted Critical
Publication of US3843322A publication Critical patent/US3843322A/en
Anticipated expiration legal-status Critical
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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
    • D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/928—Solvents other than hydrocarbons
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • 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
    • D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/621—Compounds without nitrogen
    • D06P1/622—Sulfonic acids or their salts
    • D06P1/625—Aromatic
    • 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
    • D06P1/924—Halogenated hydrocarbons
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/70—Material containing nitrile groups
    • D06P3/76—Material containing nitrile groups using basic dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8266—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and nitrile groups
    • 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
    • Y10S8/927—Polyacrylonitrile fiber
    • 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
    • Y10S8/938—Solvent dyes

Definitions

  • a continuous solvent dyeing process for the solvent dyeing of polyacrylic and similar fibers is provided utilizing a clear, stable solution obtained by complexing basic dyes with linear alkylarylsulfonic acid surfactants in a solvent mixture of a lower alcoholic solvent and an alkalizing agent.
  • the clear solution of the basic dye complexed with linear alkylarylsulfonic acid surfactant is mixed with a lower alkyl water-insoluble chlorinated solvent.
  • This application is directed to a continuous solvent dyeing process for the dyeing of polyacrylic and similar fibers; more particularly, the present invention is directed to such a continuous solvent dyeing process utilizing a solution of a complex of a basic dye with a linear alkylarylsulfonic acid surfactant in a solvent mixture of a lower alcoholic solvent and an alkalizing agent.
  • Acrylic fibers have the common characteristic that such fibers are all hydrophobic.
  • Such hydrophobic polymers are difficult to dye with many of the usual types of commercially available dyestuffs by pad thermofixation, particularly to uniform deep shades.
  • many fabrics made therefrom have only been available in pastel shades.
  • thermofixation process basically comprises a continuous method for dye ing fibers, fabrics, etc. by a brief exposure of such material to high temperatures.
  • temperatures of approximately 375-430 F. for 30 seconds to 3 minutes are conventionally utilized in a T hermosol process to thermofix the dispersed dye in the dyeing of polyester fibers etc.
  • Dispersed dyestuffs can be thermofixed on acrylic fibers, but such dyestuffs cannot be built up to medium and heavy depth, and also, their fastness is generally not sufficient for most uses. While cationic dyestuffs also thermofix on acrylic fibers and in some cases yield good results, there are certain inconveniences present again with the employment of such materials. These include, for example, lack of buildup, incompatibility and sensitivity to other classes of dyes and chemicals that may have to be United States Patent O used to assist the operation or to dye other components of a multifiber blend, and, a heavy staining of the equipmen that is used in the application of cationic dyestuffs on acrylic fibers. Thus, for example, pad rolls, frame clips, etc. become so heavily stained that cleaning between different runs becomes a major and costly operation in the employment of cationic dyestuffs.
  • the preparation of the dyestuff solution in a concentrated form is advantageous so as to minimize shipping costs and to minimize storage facilities.
  • it is frequently very diflicult to provide such concentrated solutions which will be stable under the adverse temperature and time conditions of transportation and storage.
  • the solution changes its form and specking of the dye material frequently occurs. This, of course, is a disadvantage which cannot be tolerated with todays requirements of uniformly-dyed products.
  • acrylic fibers and fabrics can be very effectively dyed in a solvent dyeing process by utilizing a clear, stable solution of a cationic dyestuff complexed with a linear alkylarylsulfonic acid surface-active agent mixed with a lower alkyl water-insoluble chlorinated solvent.
  • the dyeings which can be achieved by the use of such a solvent system are brighter than dyeings obtained with a conventional method of dyeing utilizing an aqueous system.
  • water pollution is eliminated during dyeing since solvent recovery is practical in commercial operations.
  • dyeing time is shorter, damage to the fiber can be minimized and production accordingly increased.
  • the viscose is considerably less stained than when dyed by use of conventional aqueous system.
  • the dyestuff of the present invention is in the form of a clear, stable solution of a basic dye complexed with a linear alkylarylsulfonic acid surface-active agent.
  • a basic dye complexed with a linear alkylarylsulfonic acid surface-active agent in order to produce such complexes that will liquify readily and produce liquids that are sufficiently concentrated and stable to be used in commercial dyeing, it has been found that only linear alkylarylsulfonic acids can be utilized as the anionic portion of the complex.
  • the anionic portion in accordance with the present invention thus comprises a linear alkylarylsulfonic acid surface-active agent and the .same should not be confused with an anionic dyestuff.
  • linear alkylarylsulfonic acid surface active agents utilized in accordance with the present invention are generally C to C alkylarylsulfonic acids wherein the aryl moiety is selected from benzene, diphenyl and naphthyl series.
  • exemplary linear alkylarylsulfonic acids, suitably used in accordance with the present invention include such as:
  • nmonylbenzenesulfonic acid n-dodecylbenzenesulfonic acid n-hexadecylbenzenesulfonic acid n-octadecylbenzenesulfonic acid n-tridecylbenzenesulfonic acid n-nonyldiphenylsulfonic acid n-dodecyldiphenylsulfonic acid n-nonylnaphthalenesulfonic acid.
  • linear alkylarylsulfonic acid surface active agents as well as various others falling within such description are commercially available under various trade names.
  • such linear alkylarylsulfonic acid surface active agents in the form of specific compounds and blends or mixtures thereof as the acid or alkali metal salts of the acid are sold as:
  • Nacconol 98 SA (Allied Chemicals) Calsoft LAS-99 (Allied Chemicals) Conoco C-SSO (Continental Oil Co.) Conoco C-650 (Continental Oil Co.) Dowfax 2A 1 (Dow Chemical Co.) Dowfax 3B 1 (Dow Chemical Co.) Emkal NNS (Emkay Chemical Co.) Gardilene S (Albright and Wilson) Hartofol BD (Hart Products Corp.) Hipochem 40-LA (High Point Chemical Corp.) Nansa HS S (Albright and Wilson) Nansa TDB (Albright and Wilson) Nekal NF (GAF Corp.)
  • Orvas AB Procter and Gamble
  • Petro SWPX Petro SWPX
  • Richonate 40B Richonate 40B
  • Santomerse ME Syntomerse ME (Monsanto) Soropon SF (GAP Corp.)
  • Sulfrarnic Acid 1298 (Witco Chemical Corp.) Sulframine 40 (Witco Chemical Corp.).
  • the cationic dyes employed in the process of the present invention can be any of the different types of cationic or Bas1c dyes employed in the dyeing of fibers and fabrics and acrylic fibers and fabrics in particular.
  • the following basic dyes, classified by types are suitable for the preparation of the dyestuffs of this invention:
  • Sevron Yellow 3RL Caloozine Acrylic Yellow G.
  • Sevron Violet B Basie Violet 24 Sevron Blue BGL Basic Blue 35. Astrazon Blue CSGL. Basic Blue 45. Astrazon Blue 3RLW Basic Blue 47. Thiazine:
  • Basic Yellow 15 Basic Yellow 26. Basic Yellow 32. Basic Orange 24. Basic Orange 26. Basic Orange 31.
  • Rhodamine 6G 45160 Basic Red 1. Rhodamine G. 45150 Basic Red 8. Rhodamine B 45170 Basic Violet 10. Methine:
  • Genacryl Orange G 48030 Basic Orange 21.
  • Genacryl Orange R. 48040 Basic Orange 22 Genacryl Pink G... 48015 B21510 Red 13.
  • Genaeryl Red 6B ... 48030 Basic Violet 7.
  • the cationic dye employed in the production of the complex be an unstandardized dye.
  • a standardized dye is employed in the formation of the complex, it is generally necessary to allow for the reduced strength of the dye by the addition of larger amounts of dye in connection with the formation of the complex.
  • the cationic dyestuff-linear alkylarylsulfonic acid surfaceactive agent complexes may be produced in accordance with the present invention in situ by mixing the dye and linear alkylarylsulfonic acid surface-active agent in a suitable solvent mix. The temperature of mixing is usually that of room temperature but heating is not necessary as the reaction for complex formation is mildly exothermic.
  • the complex When the complex is prepared in situ as set forth above, the same is generally prepared by mixing one part of the cationic dye with a slight stoichiometric excess of the surface-active agent, up to about 10 parts of surface-active agent being advantageously utilized. It is to be understood, however, that even greater excesses of the linear alkylarylsulfonic acid surface active agent can be employed, but the limitation set forth above is merely one of economics. Thus, the addition of greater amounts of linear alkylsulfonic acid surface active agent does not in any way inhibit the formation of a clear, stable complex but merely supplies additional surface active agent when desired.
  • the complex is generally prepared in situ by mixing the cationic dyestuif and surface active agent in a suitable alcoholic solvent.
  • alcoholic solvent comprises a material such as a lower alcoholic solvent such as a lower alkanol, lower alkylene glycol, or lower alkoxy alkanol.
  • suitable lower alcoholic solvents employed in accordance with the present invention include such as: l
  • the lower alcoholic solvent is generally employed in an amount of from about 5 to 25 %by weight, based upon the total weight of the complex-containing solvent system.
  • the linear alkylarylsulfonic acid be in the free acid form since it is preferable that the pH of the surfactant be within the range of about 3 to 7 when the complex with the basic dyestuif is formed. While the sodium and similar alkali metal and alkaline earth salts are applicable in accordance with the present invention, since such salts are generally at a higher pH of about 7 to 10, it is preferred that such salts be converted to the free acid form prior to preparation of the complex.
  • the final pH of the solution is within the range of 24.5, preferably 6-7.5.
  • the solution is alkalized by the addition of an alkalizing agent in an amount sufficient to adjust the pH of the final solution to the desired range.
  • alkalizing agent any can be used which is capable of adjusting the pH to the desired range.
  • Suitable alkalizing agents include such materials as lower alkylamines and lower alkanolamines; ammonium hydroxide; alkali metal hydroxides, e.g., sodium hydroxide, potassium hydroxide, lithium hydroxide; alkali metal carbonates and bicarbonates, e.g., sodium carbonates, sodium bicarbonate, potassium carbonate, potassium bicarbonate, lithium carbonate, lithium bicarbonate; magnesium oxide, etc.
  • the lower alkylamines and hydroxides are preferred.
  • the lower alkylamines employed in accordance with the present invention include lower alkyl primary, secondary and tertiary amines as Well as primary, secondary and tertiary lower alkanol amines.
  • lower alkyl primary, secondary and tertiary amines as Well as primary, secondary and tertiary lower alkanol amines.
  • such lower alkylamine components of the solvent mix include such as: propylamine, isopropylamine, diisopropyla-mine, triisopropylamine, isobutylamine, monoethanolamine, diethanolamine, triethanolamine, methylaminoethanol, dimethylaminoethanol, butanolamine, pentanolamines, hexanolamines, heptanolamines and the like.
  • These liquid lower alkyl amines are employed in amounts of from 3 to about parts of the total weight of the formulation.
  • Examples of such lower alkyl water-insoluble chlorinated solvents suitably employed in the solvent dyeing process of the present invention include such materials as:
  • the solvent dyeing process in accordance with the present invention other additives may be included in the system such as antifoam agents, booster solvents such as dimethylformamide and the like.
  • the polyacrylic material or polyacrylic material in admixture with other fibers is then padded with the solution.
  • the padding is generally conducted at room temperature and use of such ambient conditions is generally preferred. However, it is also possible to provide the desired dyeing of the polyacrylic material by the use of somewhat higher temperatures up to about 140 F.
  • the material that has been dyed is dried and cured at a temperautre of from about 375 to 430 F. for a period of from about seconds to 3 minutes. The dried and cured material is then finished in conventional manner or by special solvent methods, depending on the material and the finish desired.
  • the use of the solvent dyeing system and process of the present invention results in brighter colors on acrylics than can be obtained on such materials with the normal dyeing methods employing aqueous systems. Moreover, when the dyeing is conducted with respect to a polyacrylic-viscose fabric, the viscose is considerably less stained when utilizing the solvent system and dyeing process of the present invention than when the mixed fabric is dyed with an aqueous system.
  • Other advantages are present, however, with the use of the solvent system and process of the present invention. Thus, for example, wetting of the fiber is faster so that there is less swelling of the fiber, and therefore, less mechanical deformation. Additionally, since the solvent can be easily recovered in the system, effluent problems from dye plants are reduced and the recoverability of the solvent provides an economic advantage over previously utilized systems when equated with the cost of full anti-pollution measures.
  • the resulting solution was clear when diluted with water, and was stable under prolonged storage conditions, i.e., did not haze or form a precipitate.
  • Genacryl Blue 3G (0.1. Basic Blue 3; 0.1. 51005)
  • Genacryl Red GB (0.1. Basic Violet 7; 0.1. 35
  • Genacryl Orange G (0.1. Basic Orange 21; 0.1. 19
  • the Orion was dyed in bright dyeings with little or no stain on the viscose. This is in contrast with Orlon-viscose dyed in the same manner from an aqueous bath wherein the viscose was heavily stained and the Orlon dyeings were not as bright.
  • Example 2 was made into a solution in the manner of Example 1, and was then made into a solvent mix and dyed in the manner of Examples 23-27.
  • the Orlon was dyed a bright red with very little stain on the viscose.
  • Example 1 The solution of Example 1 was admixed with perchloroethylene in the following amounts:
  • Example 1 The solution of Example 1 was made into a solvent mix employing the following:
  • 1,2-dichloroethylene gal.).. 'lzichloroethylene (gaL) 1,2-diehloroethane (gaL) 1,1,2,2-tetraehloroethane (gal) Tetraehloromethane (gaL) 1,2 dichlor0peopane (gaL)
  • Example No: Surface active agent 45 n-Hexadecylbenzenesulfonic acid. 46 n-Octadeeylbenzenesulfonic acid. 47 n-Nonyldiphenylsulfonic acid.
  • EXAMPLE 50 Polyacrylonitrile was pad-dyed in the same manner as Examples 23 to 27 and gave excellent dyeings.
  • Assistant A from Example 49
  • Assistant B from Example 49
  • Solvent dyeings were made in the same manner as Examples 23-27, giving excellent dyeings.
  • the present invention comprises an improved method of dyeing acrylic and mixed acrylic fibers and fabrics as well as a solvent system therefor.
  • the method of the present invention comprises contacting the fibers and fabrics with a solvent system comprising a lower alkyl water-insoluble chlorinated solvent and from 0.1 to 20 parts per 100 parts of said chlorinated solvent of a complex of a cationic dyestuif and a linear alkylarylsulfonic acid surface active agent dissolved in a lower alcoholic solvent, together with an alkalizing agent and Water in an amount sufficient to form a clear, stable solution of the complex.
  • such method of dyeing acrylic and mixed acrylic fibers and fabrics generally comprises contacting the fibers and fabrics with such a system at a temperature of from about room temperature up to the boiling point of the solvent system.
  • the solvent system and process of the present invention have eliminated the generally used aqueous systerns which, while allowing effective dyeing, cannot produce the degree of brightness associated with the present invention.
  • dyeings obtained by the use of the solvent system of the present invention are brighter than colors obtained in the normal method of dyeing utilizing an aqueous system and in the case of dyeing a mixed polyacrylic-viscose fabric, the viscose is considerably less stained than when dyed with an aqueous system.
  • the present invention comprises a distinct improvement over those conventional aqueous systems of the prior art and provides an additional benefit in reducing a source of water pollution by dye plant efiiuent.
  • a lower alcoholic solvent present in an amount Within the range of from about to about 25% by weight based on the total weight of said complex and said alcoholic solvent;
  • the resulting clear, stable dyestulf solution is capable of producing a greater degree of brightness than conventional aqueous dyestulf solutions, the short dyeing time required with said dyestulf solution minimizing damage to the fiber being dyed and permitting increased dyed fiber production.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US00100536A 1970-12-21 1970-12-21 Dyestuff solution for acrylic fibers Expired - Lifetime US3843322A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US00100536A US3843322A (en) 1970-12-21 1970-12-21 Dyestuff solution for acrylic fibers
FR7145217A FR2118924B1 (enrdf_load_stackoverflow) 1970-12-21 1971-12-16
CA130,591A CA964006A (en) 1970-12-21 1971-12-20 Continuous solvent dyeing process and dye complex for use therein
IT32648/71A IT944175B (it) 1970-12-21 1971-12-20 Processo continuo di tintura con solventi e complesso colorante da usare in esso
CH1860471A CH561817A (enrdf_load_stackoverflow) 1970-12-21 1971-12-21
GB5920971A GB1361439A (en) 1970-12-21 1971-12-21 Solvent dyeing process
DE19712163427 DE2163427A1 (de) 1970-12-21 1971-12-21 Verfahren zum Färben von acrylischen Fasern
BE777024A BE777024A (fr) 1970-12-21 1971-12-21 Procede continu de teinture au solvant, et complexe de colorantdestine a etre utilise dans ce procede
NL7117602A NL7117602A (enrdf_load_stackoverflow) 1970-12-21 1971-12-21
CH1860471D CH1860471A4 (enrdf_load_stackoverflow) 1970-12-21 1971-12-21

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US00100536A US3843322A (en) 1970-12-21 1970-12-21 Dyestuff solution for acrylic fibers

Publications (1)

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US3843322A true US3843322A (en) 1974-10-22

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US00100536A Expired - Lifetime US3843322A (en) 1970-12-21 1970-12-21 Dyestuff solution for acrylic fibers

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US (1) US3843322A (enrdf_load_stackoverflow)
BE (1) BE777024A (enrdf_load_stackoverflow)
CA (1) CA964006A (enrdf_load_stackoverflow)
CH (2) CH1860471A4 (enrdf_load_stackoverflow)
DE (1) DE2163427A1 (enrdf_load_stackoverflow)
FR (1) FR2118924B1 (enrdf_load_stackoverflow)
GB (1) GB1361439A (enrdf_load_stackoverflow)
IT (1) IT944175B (enrdf_load_stackoverflow)
NL (1) NL7117602A (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4066395A (en) * 1974-12-02 1978-01-03 Ciba-Geigy Corporation Process for dyeing or printing aromatic polyamide fibres
US4097233A (en) * 1972-12-16 1978-06-27 Nippon Kayaku Co., Ltd. Basic dye composition
US20110027548A1 (en) * 2008-03-28 2011-02-03 Clariant Finance (Bvi) Limited Influencing the Near Infrared Reflectance of Dyed Textile Materials

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1469603A1 (de) * 1964-06-11 1969-08-28 Basf Ag Verfahren zur Trocknung und Fixierung auf Acrylnitrilpolymerisate enthaltendes oder daraus bestehendes Fasergut aufgeklotzter basischer Farbstoffe mit Trockenhitze
GB1248652A (en) * 1968-04-25 1971-10-06 Du Pont Water-insoluble dye salts
US3630663A (en) * 1968-08-30 1971-12-28 Bayer Ag Process for dyeing anionic modified synthetic fibers in dye baths containing an organic nitrogen compound
US3643270A (en) * 1968-12-20 1972-02-22 Bayer Ag Process for dyeing anionic groups containing synthetic fiber materials

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097233A (en) * 1972-12-16 1978-06-27 Nippon Kayaku Co., Ltd. Basic dye composition
US4066395A (en) * 1974-12-02 1978-01-03 Ciba-Geigy Corporation Process for dyeing or printing aromatic polyamide fibres
US20110027548A1 (en) * 2008-03-28 2011-02-03 Clariant Finance (Bvi) Limited Influencing the Near Infrared Reflectance of Dyed Textile Materials

Also Published As

Publication number Publication date
CH561817A (enrdf_load_stackoverflow) 1975-05-15
BE777024A (fr) 1972-06-21
NL7117602A (enrdf_load_stackoverflow) 1972-06-23
CH1860471A4 (enrdf_load_stackoverflow) 1974-11-15
GB1361439A (en) 1974-07-24
IT944175B (it) 1973-04-20
FR2118924A1 (enrdf_load_stackoverflow) 1972-08-04
FR2118924B1 (enrdf_load_stackoverflow) 1976-06-04
CA964006A (en) 1975-03-11
DE2163427A1 (de) 1972-06-22

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