US3873265A - Vat or reactive dyes or mixtures thereof and acrylamide or methylene bis acrylamide in alkaline crosslinking and dyeing - Google Patents

Vat or reactive dyes or mixtures thereof and acrylamide or methylene bis acrylamide in alkaline crosslinking and dyeing Download PDF

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US3873265A
US3873265A US328941A US32894173A US3873265A US 3873265 A US3873265 A US 3873265A US 328941 A US328941 A US 328941A US 32894173 A US32894173 A US 32894173A US 3873265 A US3873265 A US 3873265A
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reactive
acrylamide
acid
dyestuff
vat
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US328941A
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Rolf Kleber
Otto Smerz
Gunther Trapp
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Hoechst AG
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Hoechst AG
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    • 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
    • D06P1/0056—Dyeing with polymeric dyes involving building the polymeric dyes on the fibres
    • D06P1/0064—Dyeing with polymeric dyes involving building the polymeric dyes on the fibres by using reactive polyfunctional compounds, e.g. crosslinkers
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/41—Amides derived from unsaturated carboxylic acids, e.g. acrylamide
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/41—Amides derived from unsaturated carboxylic acids, e.g. acrylamide
    • D06M13/412—N-methylolacrylamides
    • 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
    • D06P1/22—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 vat dyestuffs including indigo
    • 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
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495—Compounds containing carbonamide -RCON= (R=H or 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
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/605—Natural or regenerated cellulose dyeing with polymeric dyes; building polymeric dyes on fibre
    • D06P3/6066—Natural or regenerated cellulose dyeing with polymeric dyes; building polymeric dyes on fibre by using reactive polyfunctional compounds, e.g. crosslinkers
    • 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
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/66—Natural or regenerated cellulose using reactive 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
    • D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8238—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye
    • D06P3/8247—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye using dispersed and vat, sulfur or indigo 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
    • D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8238—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye
    • D06P3/8252—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye using dispersed and reactive dyes
    • 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

Definitions

  • ABSTRACT A process for the simultaneous dyeing and creaseproof finishing of textile material consisting of cellulose fibers or blends of cellulose fibers and polyester fibers by impregnating the textile material with an aqueous bath containing a reactive or vat dyestuff or a disperse dyestuff and a reactive or vat dyestuff, N- methylol-acrylamide or N,N-dimethylol-methyl-bisacrylamide or an ether thereof with an alkanol containing 1 to 3 carbon atoms as well as an acid catalyst, dry heating the material to condense the N-methylol group of the synthetic resin and optionally fixing the disperse dyestuff at the same time,
  • Belgian Pat. No. 616,368 proposes simultaneously to apply crease-proofing products, hardening catalysts and vinylsulfone or sulfonamide dyes giving an alkaline reaction onto the textile material consisting entirely or predominantly of natural or regenerated cellulose.
  • the creaseproofing agent is fixed and the dye which is not sensitive to acids is fixed in a second step under alkaline conditions.
  • the textile material is treated with aqueous solutions containing a resinifying component, an acid yielding agent and dyes having a halogen atom or another reactive group and being therefore capable of reacting with the synthetic resin or the fiber in an acid medium at an elevated temperature.
  • This ambivalent cross-linking reaction imparts, in addition to excellent dry-state crease-proof'effects, also outstanding wet-state crease-proof'effects.
  • a textile material cross-linked with ambivalent agents shows drip and spin-dry effects, i.e. a self-smoothing capacity that cannot be achieved by the conventional dry cross-linking reaction.
  • drip and spin-dry effects i.e. a self-smoothing capacity that cannot be achieved by the conventional dry cross-linking reaction.
  • This invention therefore provides a process for the simultaneous dyeing and high-grade finishing of textile materials consisting of cellulose fibers or of blends of cellulose fibers and polyester fibers by a joint fixation of dyes and synthetic resin precondensates on textiles, which process comprises exposing the textile material, that has been impregnated with an aqueous bath containing an ambivalent cross-linking agent and an acid catalyst and a reactive or vat dyestuff as well as, where required a disperse dyestuff, and optionally dried at a temperature below the reaction temperature of the N- methylol groups of the cross-linking agent, to dry heat in a first fixation step to bring about acid condensation of the N-methylol groups of the cross-linking agent and, where required, simultaneously fixing the disperse dyestuff and subsequently fixing, in a second fixation step, the reactive or vat dyestuff at the same time with the ambivalent cross-linking agent in an alkaline medium, and finally carrying out the after-treatment of the textile
  • the condensation of the N-methylol groups and the simultaneous fixation of the disperse dyestuffs are brought about by means of dry heat during the first fixation step and the alkaline cross-linking reaction of the ambiva lent resin and the simultaneous development of the vat dyestuff or the fixation of the reactive dyestuff are performed in an alkaline medium during the second fixation step under the usual conditions.
  • the fast ness properties i.e. the fastness to light, rubbing and washing, of the dyeings are substantially better than those obtained when a normal crease-proofing agent, for example, of the type of an N-methylol-ethyleneurea, N-methylol-glyoxal-urea or other cross-linking agents, is used.
  • this novel process for the dyeing with reactive or vat dyes on cellulose fiber material can dispense with a pad-dyeing operation
  • Condensation performed by exposing the material at open width to dry heat for half a minute to minutes at a temperature of from about 140 to 240C, preferably from 150 to 160C.
  • the alkaline wet treatment may preferably be carried out according to the so-called cold-dwell method at room temperature, ie at about 10 to 30C, over a period of about 2 to 100 hours, using about 8 to 150 g/l of sodium or potassium hydroxide.
  • the vat dyes are preferably de veloped under steaming conditions also in the presence of an alkali metal hydroxide solution for about 10 seconds to 30 minutes at elevated temperatures of up to about C. In both cases, the cross-linking of the ambivalent creaseproofing agent is brought about simultaneously.
  • the material is finally washed, where required oxi dized, soaped and dried.
  • Optimum results can, for example, be obtained in a continuous method in an open-width washing machine having at least 7 compartments according to the following method:
  • Soaping at the boil using for example 0.5 g/l of an exyethylated castor oil and 2 g/l of acid sodium hexametaphosphate.
  • oxyethylated castor oil there are preferably used a reaction product of about 32 mols of ethylene oxide with 1 mol of castor oil or, instead, butane-diol(1,4)- pentadecaglycol ether-dioleyl ester or similar products having slightly differing ethylene oxide portions.
  • This stepwise after-treatment allows not only optimum dyeings to be obtained without any deterioration of the drystate and wet-state crease-proof behavior, but also the usual fastness properties, for example fastness to wet processing, washing and perspiration, correspond, to a large extent, to the standards of dyeings on blended fabrics which have no high-grade finish.
  • the process of the invention can be carried out without restriction with all mixtures of disperse and reactive or vat dyes.
  • the material is provided with a good selfsmoothing capacity which is very important, for example for blended fabrics of polyester fibers and cotton (drip-dry effect of about 4.5 according to Monsanto) and which cannot be achieved by a pure dry cross linking operation.
  • the feel of the goods is substantially softer and more pleasant than achieved by known methods.
  • the combination of ambivalent cross-linking, joint fixation with disperse, reactive or vat dyes is optimum as far the economy ofthe dyeing and finishing operations is concerned.
  • the process of the invention for the joint fixation of ambivalent crease-proofing products and dyes on textile materials can be applied to known cellulosic fibers and blends of polyester fibers and cellulosic fibers.
  • the cellulosic fibers may be natural fibers, such as flax, hemp, linen, cotton, or regenerated fibers, such as viscose, spun rayon or modal fibers.
  • the process of the invention may be operated with dyestuffs chosen from all the known reactive dyestuff systems, for example on the basis of monochlorotriazine, dichlorotriazine, trichloropyrimidine, vinylsulfone, vinylsulfonamide, dichloro-quinoxaline and acrylamide dyestuffs, preferably those reactive dyes which are stable under the conditions of a dry crosslinking reaction initiated by an acid catalyst.
  • dyestuffs chosen from all the known reactive dyestuff systems, for example on the basis of monochlorotriazine, dichlorotriazine, trichloropyrimidine, vinylsulfone, vinylsulfonamide, dichloro-quinoxaline and acrylamide dyestuffs, preferably those reactive dyes which are stable under the conditions of a dry crosslinking reaction initiated by an acid catalyst.
  • vat dyes there may be used dyestuffs of the type of monoand polyazo dyestuffs, of indigo, thio-indigo and the corresponding derivatives, of the anthraquinone dyestuffs having one or more anthraquinone nuclei, of indanthrone, flavanthrone and anthraquinone carbazole, of the acridones, (thio-) oxanthrones, pyranthrones, anthrathrones and anthrinides as well as of the dibenzanthrone and dibenzopyrene quinone.
  • ambivalent cross-linking agents there are used the products known from German Offenlegungsschrift No. 1,940,799 and US. Pat. No. 2,837,51 1, namely N- methylol compounds of acrylamide or of methylenebis-acrylamide or ethers of these methylol compounds with lower alkanols containing 1 to 3 carbon atoms.
  • These ambivalent cross-linking agents are employed in amounts usual for the high-grade finish of textile materials of from about 1 to 25 percent by weight, preferably from 2 to 15 percent by weight, calculated on the textile material to be finished.
  • finishing agents containing N- methylol groups may optionally be used for the process of the invention.
  • finishing agents there are mentioned, above all, methylol compounds of urea or urea derivatives as well as of the cyclic compounds, such as ethylene urea, l,3-propylene urea, melamine and derivatives thereof as well as methylol compounds of monoand dicarbamic acid esters, moreover the ethers of these methylol compounds with lower alkanols.
  • These conventional hardenable finishing agents may be added in amounts of up to about percent by weight, calculated on the amount used of the ambivalent cross-linking agent.
  • the acid catalysts chosen are substances currently used for this purpose in the high-grade finishing practice. They may be strong or medium-strong organic or inorganic acids, for example monochloracetic acid, trichloracetic acid, tartaric acid, citric acid, oxalic acid, glycolic acid, phosphoric acid, hydrochloric acid or sulfuric acid.
  • Compounds having a latent acidity which develop acid underthe conditions of the first fixation step, for example salts of medium-strong or strong acids with ammonia, amines or polyvalent metals, such as ammonium chloride, ammonium sulfate, ammonium phosphate, ethanol-ammonium chloride, magnesium chloride, zinc chloride, zinc nitrate. aluminium chloride, zinc fluorborate and zirconium oxychloride.
  • the acid catalysts are used in the usual amounts which depend especially on the amount of the ambivalent cross-linking agent used and on the other hardenable N-methylol compounds that may also be used. It generally ranges from about 0.3 to 30 percent by weight, preferably from to 25 percent by weight, calculated on the amount of the total of cross-linking agent added.
  • additives such as softeners, polyethylene dispersions, waterrepellants and other normally used products and adjuvents can be used without adversely affecting the coloristic and finish effects.
  • EXAMPLE 1 a A bleached cotton popelin material is padded with an aqueous liquor containing, per liter,
  • the liquor pick-up is 60
  • the fabric is dried at 100 l C in a laboratory-scale jet drier and then heated to 155C for 4 minutes.
  • the fabric is then impregnated on a two-roller padding machine at room temperature and at a liquor pickup of 70 /1 with an aqueous liquor containing, per liter,
  • the goods are wound up, wrapped in a plastic film and stored for 10 to 12 hours at room temperature. Then it is washed with cold water, neutralized by means of acetic acid, rinsed at 70 80C with warm water, soaped at the boil with a liquor containing 2 g/l of wetting agent, and rinsed carefully.
  • the cotton fabric thus treated has a brilliant blue shade and very good fastness properties and optimum wet and dry-state crease angles.
  • the results obtained by testing the crease-proof effects are compiled in Table l.
  • a comparison of the finish obtained according to (a) and (b) shows that the fabrics finished according to (a) with ambivalent cross-linking agents exhibit, in addition to substantially better crease-proof effects, distinctly improved fastness to rubbing in dry and wet state as well as fastness to washing at the boil and perspiration (cf. Table 1).
  • EXAMPLE 2 a A batiste fabric made of a blend of cotton and polyester fibers (50:50), having a weight of 100 g per square meter, is treated with an aqueous padding liquor containing, per liter,
  • the goods are then padded at 20C and at a liquor pickup of 60 with an aqueous solution containing, per liter,
  • the fabric is carefully washed at a transport speed of 20 meters per minute on an open-width washing machine and dried as follows:
  • EXAMPLE 3 A fabric made from mercerized cotton popeline and having a weight of g per squaremeter is treated with an aqueous liquor containing, per liter.
  • a level dyeing having excellent fastness properties and, at the same time, a high se1f-smoothing effect is obtained (cf. Table 1).
  • TABLE 1 10 consisting of N-methylol-acrylamide, N,N- dimethylol-methylene-bis-acrylamide, and others thereof with an alkanol containing 1 to 3 carbon atoms, and an acid catalyst;

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Structural Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US328941A 1972-02-07 1973-02-02 Vat or reactive dyes or mixtures thereof and acrylamide or methylene bis acrylamide in alkaline crosslinking and dyeing Expired - Lifetime US3873265A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2205589A DE2205589B2 (de) 1972-02-07 1972-02-07 Verfahren zum gleichzeitigen Färben und Knitterfestausrüsten mit Kunstharzvorkondensaten von cellulosefaserhaltigen Textilien

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US3873265A true US3873265A (en) 1975-03-25

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US (1) US3873265A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CH (1) CH165673A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE2205589B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FR (1) FR2171238B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB1409362A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IT (1) IT978824B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NL (1) NL7301535A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3988108A (en) * 1973-04-09 1976-10-26 Kanebo, Ltd. Process for coloring fibrous structures
US4265631A (en) * 1978-08-02 1981-05-05 Ciba-Geigy Corporation Aqueous dyestuff preparations of water-insoluble or sparingly water-soluble dyes
CN102747569A (zh) * 2012-06-21 2012-10-24 广东德美精细化工股份有限公司 活性染料轧染染色方法
CN104532616A (zh) * 2015-01-07 2015-04-22 广东德美精细化工股份有限公司 提高酸性荧光染料的色牢度的方法
US20240368832A1 (en) * 2021-12-16 2024-11-07 Dow Global Technologies Llc One step dyeing process of a polyester/natural fiber blended fabric

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3232692A (en) * 1966-02-01 Sil\/kultaneously dyekng and resin finishing textiles
US3246946A (en) * 1961-05-09 1966-04-19 Rohm & Haas Method of crease-proofing cellulosic fabrics and fabrics obtained
US3265461A (en) * 1960-11-02 1966-08-09 Basf Ag Dye and hexahydro-1, 3, 5-triacryloyl-s-triazine or derivative thereof composition and dyeing therewith
US3510247A (en) * 1963-08-13 1970-05-05 Stevens & Co Inc J P Modification of cellulosic materials with tertiary bis-acrylamides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3232692A (en) * 1966-02-01 Sil\/kultaneously dyekng and resin finishing textiles
US3265461A (en) * 1960-11-02 1966-08-09 Basf Ag Dye and hexahydro-1, 3, 5-triacryloyl-s-triazine or derivative thereof composition and dyeing therewith
US3246946A (en) * 1961-05-09 1966-04-19 Rohm & Haas Method of crease-proofing cellulosic fabrics and fabrics obtained
US3510247A (en) * 1963-08-13 1970-05-05 Stevens & Co Inc J P Modification of cellulosic materials with tertiary bis-acrylamides

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3988108A (en) * 1973-04-09 1976-10-26 Kanebo, Ltd. Process for coloring fibrous structures
US4265631A (en) * 1978-08-02 1981-05-05 Ciba-Geigy Corporation Aqueous dyestuff preparations of water-insoluble or sparingly water-soluble dyes
CN102747569A (zh) * 2012-06-21 2012-10-24 广东德美精细化工股份有限公司 活性染料轧染染色方法
CN104532616A (zh) * 2015-01-07 2015-04-22 广东德美精细化工股份有限公司 提高酸性荧光染料的色牢度的方法
US20240368832A1 (en) * 2021-12-16 2024-11-07 Dow Global Technologies Llc One step dyeing process of a polyester/natural fiber blended fabric
US12325955B2 (en) * 2021-12-16 2025-06-10 Dow Global Technologies Llc One step dyeing process of a polyester/natural fiber blended fabric

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Publication number Publication date
IT978824B (it) 1974-09-20
FR2171238B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1976-06-11
CH165673A4 (de) 1975-08-15
DE2205589A1 (de) 1973-08-16
FR2171238A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1973-09-21
DE2205589B2 (de) 1975-05-07
NL7301535A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1973-08-09
GB1409362A (en) 1975-10-08

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