US3278253A - Process for dyeing textile materials in an aqueous bath containing a dyestuff in the presence of a trifunctional triazine - Google Patents

Process for dyeing textile materials in an aqueous bath containing a dyestuff in the presence of a trifunctional triazine Download PDF

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US3278253A
US3278253A US303425A US30342563A US3278253A US 3278253 A US3278253 A US 3278253A US 303425 A US303425 A US 303425A US 30342563 A US30342563 A US 30342563A US 3278253 A US3278253 A US 3278253A
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dyeing
dyestuff
parts
acid
active
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Weckler Gerhard
Schiessler Siegfried
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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
    • D06P1/44—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
    • D06P1/647—Nitrogen-containing carboxylic acids or their salts
    • 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
    • D06P1/60—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 polyethers
    • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
    • 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
    • D06P1/628—Compounds containing nitrogen
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/246—Polyamides; Polyurethanes using polymeric 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
    • Y10S8/924—Polyamide fiber

Definitions

  • This invention relates to improvements in the dyeing of textile materials such as yarns, filaments, fibers and fabrics having a basis of synthetic linear polyamides, as, for example, nylon. More particularly, the present invention relates to an improved process for dyeing yarns, filaments, fibers and fabrics made of, or essentially consisting of, synthetic linear polyamides with acid dyestuffs, complex metal dyestuffs or reactive dyestuffs or mixtures thereof.
  • textile materials made from polyamides can be dyed with various dyestuffs, for example, with acid wool dyestuffs, metal complex dyestuffs or chrome dyestuffs, at temperatures below and above 100 C.
  • various dyestuffs for example, with acid wool dyestuffs, metal complex dyestuffs or chrome dyestuffs, at temperatures below and above 100 C.
  • the dyeings thus produced are not satisfactory, because in most cases it is not possible to level irregularities of the yarn which are mainly caused by variations of the titer and differences in stretching and fixing. These yarn irregularities are distinctly visible after dyeing as streaks, bands or in the form of an unsettled appearance, depending on the type of goods, and they considerably reduce the sales value of the goods.
  • these products are capable of levelling out the streakiness occurring with polyamide fibers when dyeing with acid dyestuffs; in the case of difficult dyeings with acid dyestuff combinations, they exhibit retarding effects which are different for each component of the dyestuff combination, so that dyestuff losses and alterations of shade are caused.
  • the full effect of the mixtures is attained at temperatures above C., so that anti-oxidizers must be used to prevent possible oxidations taking place at these high temperatures.
  • fabric irregularities cannot be levelled out satisfactorily and a strong retardative effect is observed with some dyestuffs.
  • a drawback is also the necessity of exactly adjusting the pH-value of the dyebath for obtaining optimum effects.
  • Another object of this invention is the provision of an aqueous dyebath comprising an acid dyestuff, a complex metal dyestuff, a reactive dyestuff or a mixture thereof and a particularly effective dyeing assistant.
  • Formula I R represents hydrogen or a low molecular alkyl radical
  • A represents an aliphatic, aromatic, araliphatic, or cycloaliphatic radicals
  • n an integer from 1 to 3
  • X represents halogen, preferably chlorine or the group wherein R, A, Z and n have the meanings given above.
  • R, A, Z and n have the meanings given above.
  • compounds of the Formula I there are preferably used compounds in which R represents a hydrogen atom,
  • A represents an alkylene radical having 1-4 carbon atoms
  • the compounds of the present invention permit dyeing at temperatures of up to 130 C. without the addition of protective agents and without incurring the risk of damaging the fibres. By application of this high temperature, in many cases the yield and the levelness are rather improved.
  • Another advantage in the use of the assistants of the present invention is that dull shades on polyamide textiles are obtained, since in practice the luster of the dyed goods has always been objected to.
  • the assistants having the Formula I can be prepared, for example, by reacting amines of the formula NH'A' '(Z)n with cyanuric chloride preferably in an aqueous medium, at a reaction temperature ranging from to 100 C., while neutralizing the hydrogen chloride liberated.
  • neutralizing agents there may be preferably used mineral acid-binding agents, for example, alkali metal hydroxides, carbonates or hydrogen carbonates, and alkaline earth metal hydroxides, carbonates or hydrogen carbonates.
  • the 2,4,6 s triazine tri aminobenzene fi hydroxyethylsulfone sulfuric acid esters can also be prepared by reacting cyanuric chloride with aminobenzenefl-hydroxyethylsulfone in the melt or in a higher-boiling organic solvent, for example, xylene and subsequent esterification of the trihydroxy compound formed with concentrated sulfuric acid.
  • the addition products of alkylene oxide to alkylamines or polyalkylene polyamines prefearably the compounds obtained by the addition of 2-30 mols of ethylene oxide to 1 mol of an alkylamine having at least one alkyl radical with 8-18 carbon atoms or of a substituted alkylamine, for example, a compound of the formula in which R stands for alkyl radical having 8-18 carbon atoms, or 1 mol of a polyalkylene polyamine such as ethylene diamine, diethylene triamine or hexamethylene diamine; condensation products of melamine, formaldehyde and one compound obtained by the addition of prefer-ably 8-80 mols of ethylene oxide to 1 mol of triethanolamine, or the products obtained by acid condensation of formaldehyde and addition products of alkylene oxide, preferably of 8-50 mols of ethylene oxide
  • the ratio of the anion-active to the cation-active compound used if desired or required can vary within wide limits.
  • the anionactive compounds encompassed by the Formula I may be used with good results alone.
  • the ratio of the individual components may be adjusted to the prevailing circumstances of each individual case.
  • the components can be used in equal amounts, but it generally proved advantageous to use an excess of anionactive compound. It is preferred to use a ratio of 3 parts by weight of anion-active compound to 1 part by weight of cation-active compound.
  • a non-ionic surface-active compound for example, the product obtained by the addition of 20-40 mols of ethylene oxide to 1 mol of an alkyl phenol having an alkyl radical with about 8-12 carbon atoms.
  • the dyeing conditions such as the dyebath temperature, the pH of the dyebath, the proportion of dyestuff in the dyebath and the liquor ratio, may be varied as desired.
  • the dyebath is preferably heated to a temperature of at least to C.; mostly, the dyeing is carried out at the normal boiling point of the dyebath. Augmentation of the dyeing temperature to about l20130 C. is possible, but is in most cases not necessary to obtain streakless dyeings with good depth of shade.
  • the dyebath should have an acid pH.
  • the pH value may range between about 3 and 6, preferably between 3 and 4.
  • the small quantity of 0.5-3 percent by weight of the anion-active dyeing assistant or of the mixture of anion-active and cation-active substances according to the invention which gives good results even with deep shades, is a considerable advantage.
  • a quantity of only 0.5-2 percent by weight, referred to the weight of the goods will already be sufiicient.
  • anionactive compounds of the Formula I such as contain the group SO CH CH -OSO Y (Y having the meaning given in Formula I and rinsing the goods after dyeing for 1 to 20 minutes at temperatures in the range of 60 and 90 C. with an aqueous alkaline bath in the presence of a high molecular compound containing at least 3 hydroxyl groups.
  • aqueous alkaline bath in the presence of a high molecular compound containing at least 3 hydroxyl groups.
  • reactive vinylsulfone groups in the anion-active dyeing assistant which cause cross-linking with the added compounds containing hydroxy groups.
  • This fastnessimproving treatment can also be carried out by padding with alkalies and compounds containing hydroxyl groups the dyeings produced on polyamide fabrics in the presence of compounds of the Formula I containing the group -SO CH CH -OSO Y and then further treating the fabric as usual on the stenter at temperatures in the range of 90 and 180 C. for a period from 30 seconds to 10 minutes.
  • alkalies for the aftertreatment there may be used in particular alkali metal hydroxides, alkali metal carbonates and alkali metal bicarbonates, as well as alkali metal salts of organic acids which pass over into hydroxides or carbonates at elevated temperatures.
  • alkali metal hydroxides sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and the corresponding bicarbonates, sodium acetate, potassium acetate as well as the sodium or potassium salt of trichloroacetic acid.
  • the alkalies are generally used in amounts from about 0.3 to 10 percent by weight, preferably 0.3 to 5 percent by weight, referred to the weight of the goods.
  • the quantity should be so chosen as to give a pH of at least 8. If compounds are used, which pass into alkalies at elevated temperatures, for example, the sodium salt of trichloroacetic acid, one can work under neutral or weakly acid conditions.
  • polyvinyl alcohols having K-values from about to 100 (according to Fickentscher, Cellulosechemie, tome 13, page 58 (1932)), polyvinyl alcohols which can be either fully hydrolyzed or partly hydrolyzed and have a residual acetyl content of 090% as well as polyvinyl acetals containing hydroxyl groups, i.e.
  • partly acetalized polyvinyl alcohols for example, acetalized with formaldehyde, acetaldehyde, benzaldehyde or other aliphatic or aromatic aldehydes, with an acetalization degree of 099% and K-values from 10 to 100.
  • copolymers of monomeric vinyl compounds such as vinyl chloride, acrylic acid esters, methacrylic acid esters, acrylonitrile, styrene, etc. with vinyl esters such as vinyl formiate, vinyl acetate, vinyl propionate, etc., into which hydroxyl groups have been introduced by partial hydrolysis.
  • the proportion of vinyl ester groups in the mentioned copolymers can vary between 0.5 and 99%, the degree of hydrolyzation of the vinyl ester component can vary from about 10 to 100%.
  • suitable resins or partially hydrolyzed graft polymers of vinyl esters with polyethylene glycols for example, those obtained according to the German specifications 1,081,229 and 1,094,457.
  • hydroxyl-containing compounds of natural origin there may be used inter alia carbohydrates such as starches (wheat starch, rice starch, potato starch, etc.) tragacanth, tannine, locust bean flour as well as locust bean flours that are partially etherified with lower, monoor dihydric aliphatic alcohols having 14 carbon atoms, modified star-ch preparations for example, British rubber, sugar, and sugar alcohols, furthermore cellulose esterified with lower carboxylic acids or lower alcohols having 14 carbon atoms or etherified cellulose, for example, methyl cellulose, carboxymethyl cellulose, etc.
  • carbohydrates such as starches (wheat starch, rice starch, potato starch, etc.) tragacanth, tannine, locust bean flour as well as locust bean flours that are partially etherified with lower, monoor dihydric aliphatic alcohols having 14 carbon atoms, modified star-ch preparations for example, British rubber, sugar, and sugar alcohols, furthermore cellulose ester
  • Example 1 100 parts of a polyamide fabric consisting in warp and beam of endless filaments, normally dyeing 'with streaks only, are dyed in a closed dyeing apparatus for 1 hour at 100 C. with 2 parts of an acid wool dyestuff strongly responding to yarn irregularities and having the general formula 1000 parts of water, after having brought the dyebath to the above temperature in the course of 40-50 minutes. After rinsing and drying, there is obtained a streakless, fast, grey dyeing.
  • An improved fastness can be obtained, when treating the goods in the first rinsing bath with 2 parts of sodium trichloroacetate, or 2 parts of sodium bicarbonate alone or together with 2 parts of tannine, for 20 minutes at 60-80 C.
  • the described aftertreatment can be carried out by padding on a foulard and drying the dyed fabric on a stenter for 5 minutes at 140 C.
  • Example 2 parts of the fabric described in Example 1 are dyed as described in Example 1 with a dyebath having the following composition:
  • Example 3 100 parts of the polyamide fabric which can be dyed with streaks only and which is described in Example 1,
  • Example 4 100 parts of the polyamide fabric described in Example 1 which can be dyed with streaks only are dyed under the conditions described in Example 1 with a dyebath having the following composition:
  • Example 5 parts of the fabric of polyamide described in Example 1, which can be dyed with streaks only, are dyed with a combination of acid dyestuffs of 4 parts of the red dyestuff A, 3.6 parts of the yellow dyestuff B, 0.05 part of the blue dyestulf C.
  • Example 6 100 parts of the fabric described in Example 1 are dyed, after singeing, for 10 minutes at 30 0., with a bath having the following composition:
  • the dyed goods are then rinsed and dried. There is obtained a level grey dyeing.
  • the nodules formed by the singeing would be dyed deeper owing to their greater afiinity for the dyestuif than the fabric.
  • Example 7 100 parts of the fabric described in Example 1 are dyed for 15 minutes at 30 C. with a bath having the following composition: 1000 parts of water, 3 parts of 2,4,6-.tri-(1-aminobenzene-2,4-disulfonic aoid)-s-triazine, 1 part of the condensation product of 6 mols of ethylene oxide and 1 mol of laurylamine, and 3 parts of acetic acid (30% strength).
  • R is a member selected from the group consisting of hydrogen and a low molecular alkyl radical
  • A is a member selected from the group consisting of an alkylene radical having 1-4 carbon atoms, a phenylene and naphthylene radical, a substituted phenylene and a substituted naphthylene radical
  • Z is a member selected from the group consisting of SO Y, -OSO Y, COOY, and SO CH CH OSO Y (Y being a member selected from the group consisting of hydrogen and a salt-forming cation) and n is an integer from 1 to 3, as an assistant for levelling the dyeing.
  • Process for dyeing textile materials having a basis of a synthetic linear polyamide which comprises bringing said textile materials into contact with an aqueous dye- 10 bath containing an acid wool dyestuff in the presence of a colorless compound of the formula i Z n-AN(;J ⁇ (IJNAZ n N ⁇ /N C in which R is a member selected from the group consisting of hydrogen and a low molecular alkyl radical, A is a member selected from the group consisting of an alkylene radical having 1-4 carbon atoms, a phenylene and a naphthylene radical, a substituted phenylene and a substituted naphthylene radical, Z represents the group SO CH CH OSO Y (Y being a member selected from the group consisting of hydrogen and a salt-forming cation) and n is an integer from 1 to 3, as an assistant for levelling the dyeing, and rinsing the dyed materials in an aqueous alkaline bath containing a high molecular
  • Process for dyeing textile materials having a basis of a synthetic linear polyamine which comprises bringing said textile materials into contact with an aqueous dyebath containing a dyestuff for said materials in the presence of a colorless compound of the formula RI IAZu in which R is a member selected from the group consisting of hydrogen and a low molecular alkyl radical, A is a member selected from the group consisting of an alkylene radical having 1-4 carbon atoms, a phenylene and a naphthylene radical, a substituted phenylene and a substituted naphthylene radical, Z is a member selected from the group consisting of --SO Y, COOY, and SO CH CH OSO Y (Y being a member selected from the group consisting of hydrogen and a salt-forming cation) and n is an integer from 1 to 3, and a complexforming weakly cation-active product as assistants for levelling the dyeing.
  • R is a member selected from the group consisting of hydrogen and
  • a process as defined in claim 5, wherein the complex-forming Weakly cationic active product is an addition product of 2 to 30 mols of ethylene oxide per mol of an alkylamine having an alkyl radical with 8 to 18 carbon atoms.

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US303425A 1962-08-22 1963-08-20 Process for dyeing textile materials in an aqueous bath containing a dyestuff in the presence of a trifunctional triazine Expired - Lifetime US3278253A (en)

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DEF37646A DE1290519B (de) 1962-08-22 1962-08-22 Verfahren zum streifenfreien Faerben von Textilmaterialien aus Polyamiden

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AT (1) AT252170B (it)
BE (1) BE636485A (it)
CH (1) CH403707A (it)
DE (1) DE1290519B (it)
DK (1) DK108362C (it)
FR (1) FR1367257A (it)
GB (1) GB1060718A (it)
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NO (1) NO120472B (it)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3481903A (en) * 1967-05-15 1969-12-02 Gaetano F D Alelio Chelating compositions comprising products of aldehydes and triazine derivatives
US3519627A (en) * 1968-04-09 1970-07-07 Ashland Oil Inc Carboxyl-containing ethers of amino-triazine/aldehyde condensates
US3615739A (en) * 1963-12-31 1971-10-26 Geigy Chem Corp Floor polishing composition containing substituted {11 -triazines
US3743477A (en) * 1967-07-03 1973-07-03 Sandoz Ltd Process for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes
US3890091A (en) * 1972-09-08 1975-06-17 Hoechst Ag Level dyeing of wool polyimine or polyamine and sulfonated phenylene amino-chlorotriazine treated
US3930795A (en) * 1972-09-08 1976-01-06 Hoechst Aktiengesellschaft Process for the level dyeing of wool
US4132850A (en) * 1977-06-29 1979-01-02 American Cyanamid Company Tri-substituted triazines
US4183929A (en) * 1977-06-29 1980-01-15 American Cyanamid Company Tri-substituted triazines
US4444563A (en) * 1981-09-07 1984-04-24 Ciba-Geigy Corporation Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials
EP0118983A2 (en) * 1983-02-11 1984-09-19 Wool Development International Limited Textile treatment
EP0174794A2 (en) * 1984-09-14 1986-03-19 Wool Development International Limited Textile treatment
EP0175225A2 (de) * 1984-09-15 1986-03-26 Hoechst Aktiengesellschaft Faserreaktive Triazinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung
US4587338A (en) * 1983-09-16 1986-05-06 Hoechst Aktiengesellschaft Perfluoroalkyl esters of anthranilic acids
US4617390A (en) * 1982-02-23 1986-10-14 Basf Aktiengesellschaft S-triazine derivatives
US4695632A (en) * 1976-06-12 1987-09-22 Bayer Aktiengesellschaft Quaternary reactive compounds
US4886882A (en) * 1985-09-07 1989-12-12 Basf Aktiengesellschaft Hydroxyoxaalkylmelamines
US5571444A (en) * 1989-09-11 1996-11-05 Invicta Group Industries Pty Ltd. Textile treatment
WO1997035848A1 (de) * 1996-03-25 1997-10-02 Basf Aktiengesellschaft Triazinderivate als fixiermittel beim färben und als vernetzer
US5792222A (en) * 1996-03-04 1998-08-11 Ciba Specialty Chemicals Corporation Process for dyeing natural or synthetic polyamide fibre materials
US6022378A (en) * 1996-06-21 2000-02-08 Lenzing Aktiengesellschaft Process for the treatment of cellulose fibres and of assemblies made from these fibres

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EP0102926B1 (de) * 1982-09-03 1987-01-07 Ciba-Geigy Ag Färbereihilfsmittel und seine Verwendung beim Färben oder Bedrucken von synthetischen Polyamidfasermaterialien
EP0302013A1 (de) * 1987-07-27 1989-02-01 Ciba-Geigy Ag Verfahren zum Färben von textilen Flächengebilden aus Polyamiden

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US3054699A (en) * 1957-06-12 1962-09-18 Ici Ltd Water-soluble latent curing catalysts for textile treatment resins

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Publication number Priority date Publication date Assignee Title
BE580952A (it) * 1958-07-24

Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
US3054699A (en) * 1957-06-12 1962-09-18 Ici Ltd Water-soluble latent curing catalysts for textile treatment resins

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3615739A (en) * 1963-12-31 1971-10-26 Geigy Chem Corp Floor polishing composition containing substituted {11 -triazines
US3481903A (en) * 1967-05-15 1969-12-02 Gaetano F D Alelio Chelating compositions comprising products of aldehydes and triazine derivatives
US3743477A (en) * 1967-07-03 1973-07-03 Sandoz Ltd Process for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes
US3519627A (en) * 1968-04-09 1970-07-07 Ashland Oil Inc Carboxyl-containing ethers of amino-triazine/aldehyde condensates
US3890091A (en) * 1972-09-08 1975-06-17 Hoechst Ag Level dyeing of wool polyimine or polyamine and sulfonated phenylene amino-chlorotriazine treated
US3930795A (en) * 1972-09-08 1976-01-06 Hoechst Aktiengesellschaft Process for the level dyeing of wool
US4695632A (en) * 1976-06-12 1987-09-22 Bayer Aktiengesellschaft Quaternary reactive compounds
US4132850A (en) * 1977-06-29 1979-01-02 American Cyanamid Company Tri-substituted triazines
US4183929A (en) * 1977-06-29 1980-01-15 American Cyanamid Company Tri-substituted triazines
US4444563A (en) * 1981-09-07 1984-04-24 Ciba-Geigy Corporation Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials
US4617390A (en) * 1982-02-23 1986-10-14 Basf Aktiengesellschaft S-triazine derivatives
EP0118983A2 (en) * 1983-02-11 1984-09-19 Wool Development International Limited Textile treatment
US4563189A (en) * 1983-02-11 1986-01-07 Wool Development International Ltd. Treatment of fibers with arylating agents to enhance disperse dyeability
EP0118983A3 (en) * 1983-02-11 1986-07-16 Wool Development International Limited Textile treatment
US4587338A (en) * 1983-09-16 1986-05-06 Hoechst Aktiengesellschaft Perfluoroalkyl esters of anthranilic acids
EP0174794A2 (en) * 1984-09-14 1986-03-19 Wool Development International Limited Textile treatment
US4950301A (en) * 1984-09-14 1990-08-21 Wool Development International Limited Keratinous textile treatment with arylating compounds containing fibre reactive groups
EP0174794A3 (en) * 1984-09-14 1987-09-16 Wool Development International Limited Textile treatment
EP0175225A2 (de) * 1984-09-15 1986-03-26 Hoechst Aktiengesellschaft Faserreaktive Triazinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0175225A3 (de) * 1984-09-15 1987-04-29 Hoechst Aktiengesellschaft Faserreaktive Triazinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung
US4886882A (en) * 1985-09-07 1989-12-12 Basf Aktiengesellschaft Hydroxyoxaalkylmelamines
US5571444A (en) * 1989-09-11 1996-11-05 Invicta Group Industries Pty Ltd. Textile treatment
US5792222A (en) * 1996-03-04 1998-08-11 Ciba Specialty Chemicals Corporation Process for dyeing natural or synthetic polyamide fibre materials
US5922865A (en) * 1996-03-04 1999-07-13 Ciba Specialty Chemicals Corporation Process for dyeing natural or synthetic polyamide fiber materials
WO1997035848A1 (de) * 1996-03-25 1997-10-02 Basf Aktiengesellschaft Triazinderivate als fixiermittel beim färben und als vernetzer
US6120562A (en) * 1996-03-25 2000-09-19 Basf Aktiengesellschaft Triazine derivatives as fixers in coloring and as cross-linking agents
US6022378A (en) * 1996-06-21 2000-02-08 Lenzing Aktiengesellschaft Process for the treatment of cellulose fibres and of assemblies made from these fibres

Also Published As

Publication number Publication date
NO120472B (it) 1970-10-26
CH1021563A4 (it) 1965-08-31
BE636485A (it)
GB1060718A (en) 1967-03-08
DK108362C (da) 1967-11-27
CH403707A (de) 1966-06-15
DE1290519B (de) 1969-03-13
FR1367257A (fr) 1964-07-17
NL125292C (it)
NL296874A (it)
AT252170B (de) 1967-02-10

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