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Publication numberUS3278253 A
Publication typeGrant
Publication dateOct 11, 1966
Filing dateAug 20, 1963
Priority dateAug 22, 1962
Also published asDE1290519B
Publication numberUS 3278253 A, US 3278253A, US-A-3278253, US3278253 A, US3278253A
InventorsWeckler Gerhard, Schiessler Siegfried
Original AssigneeHoechst Ag
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Process for dyeing textile materials in an aqueous bath containing a dyestuff in the presence of a trifunctional triazine
US 3278253 A
Abstract  available in
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Description  (OCR text may contain errors)

United States Patent 3,278,253 PROCESS FOR DYEING TEXTILE MATERIALS IN AN AQUEOUS BATH CONTAINING A DYESTUFF IN THE PRESENCE OF A TRIFUNCTIONAL TRI- AZINIE Gerhard Weckler and Siegfried Schiessler, Frankfurt am Main, Germany, assignors to Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius & Briining, Frankfurt am Main, Germany, a corporation of Germany No Drawing. Filed Aug. 20, 1963, Ser. No. 303,425 Claims priority, application Germany, Aug. 22, 1962, F 37,646 9 Claims. (Cl. 8-17) 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.

It is well known in the art that 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. However, 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.

To by-pass these drawbacks, it has been proposed, in addition to selecting a suitable dyestuff, to retard'the dyeing process and to carry it out in the presence of swelling agents in order to augment the penetration into the fiber, and thus to prevent blocking effects. As swelling agent-s, there have been used, for example, phenols and chlorinated, aromatic substances. These products, however, involve a number of disadvantages. They are, in most cases, not simple to use and they are effective only in high concentrations. In addition, they are partly strongly absorbed by the fibers so that they can be removed later on with difficulty only and may then cause damage to the fibers. Although they reduce streakiness, they do not totally remove the streaks.

Furthermore, attempts have also been made to produce level dyeings through control of the substantivity of the dyestuff by shifting the pH-value of the dyebath during dyeing by the addition of a potentially acid dyeing assistant to the bath. However, this process does not remove or level streakiness of the fabric dyed.

Furthermore, it is known to use surface-active agents in the dyeing of polyamide fibers. Attempts have been made to produce level dyeings by adding cation-active dyeing assistants to the dyebath which are capable of forming complexes with acid wool dyestuffs, and to retard their penetration into the fiber. This process, too, does not yield satisfactory results, because the cation-active products tend to precipitate the acid dyestuffs. Even the addition of non-ionic dispersing agents to the dyebath does not remove the difficulties and does not offer the required reliability. Furthermore, there has been described the use of anion-active products which are added to the dyebath and which are to compete with the dyestuff for the free linking positions of the fibers. However, these products possess either such strong aflinity for the polyamide fiber that all linking positions of the fiber are occupied by the dyeing assistant and that the dyebaths cannot be ex- 3,278,253- Patented Oct. 11, 1966 hausted, or they are well able to retard the penetration of the acid dyestuff into the polyamide fiber in the case of light dyeings, but do not satisfactorily level out the streakmess.

Furthermore, products are described in the literature which are a combination of special, anion-active substances with complex-forming, weakly cation-active surface-active compounds such as polyvinyl pyrrolidone, or hydroxyethylated aminophenols.

In many cases 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. In the dyeing of polyamide fibers with complex metal dyestuffs and reactive dyestuffs, 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.

It is an object of this invention to provide an improved process for the more complete dyeing of textile materials having a basis of a synthetic linear polyamide with a dyestuff for said material. 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. Other objects of this invention will be apparent from the following detailed description and claims:

We have found that streak-free dyeings on textile materials having a basis of a synthetic linear polyamide with acid dyestuffs as well as with complex metal dyestuffs and reactive dyestuffs are obtained, when carrying out the dyeing in the presence of a colorless compound of the formula (I) if desired or required, together with a weakly cation-active, complex-forming agent.

In the above Formula I R represents hydrogen or a low molecular alkyl radical,

A represents an aliphatic, aromatic, araliphatic, or cycloaliphatic radicals,

Z represents an anion-active group such, for example, as SO Y, -OSO -,Y, -COOY, -SO CH CH OSO Y (Y=hydrogen or a salt forming cation, preferably an alkali metal cation),

n represents 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. As 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,

a phenylene radical, a naphthalene radical or a phenylene or naphthalene radical substituted by one or several nitro groups, amino groups, low molecular alkyl or alkoxy radicals, and/or halogen, and Z, n and X have the meanings given above.

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.

As 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.

As amines of the general formula there may be used:

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.

As complex-forming, weakly cation-active products which may be used, if required or desired, together with the compounds of the Formula I, there enter into consideration, for example, 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 to 1 mol of a mixture of a simple aromatic amine such, for example, as aniline and a phenol, and, if required or desired, a low molecular alkanolamine, especially triethanolamine. Furthermore, there may be used the quaternization products of the above-specified compounds, for example, those obtained by the reaction with dimethyl sulfate.

The ratio of the anion-active to the cation-active compound used if desired or required, can vary within wide limits. Thus, as has already been mentioned, the anionactive compounds encompassed by the Formula I may be used with good results alone. When mixtures of the mentioned anion-active and cation-active compounds are used, 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.

For stabilization, there may be added to the mixtures of anion-active and cation-active compounds, if desired or required, about 0.5-2% of 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. Thus 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.

In comparison with the quantity used of other known assistants, 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. In many cases, a quantity of only 0.5-2 percent by weight, referred to the weight of the goods, will already be sufiicient.

When using the compounds or mixtures according to the present invention, streakless, level dyeings on polyamide fibrous materials will be obtained. Changes of the depth of shade and of the shade itself do not occur or only in a practically insignificant degree. The drawbacks of the known processes are thereby obviated.

Furthermore, when using the products in the dyeing of polyamide fibers with acid wool dyestuffs, good wetting and rubbing fastnesses are obtained. Especially good results will in this case be obtained when using as 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. During this treatment in the alkaline medium, there form 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.

As 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. There are mentioned by way of example: 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.

As higher molecular compounds of synthetic origin, with alcoholic hydroxyl groups, there enter into consideration for example, 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. Furthermore, 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%. Furthermore, there are also 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.

As 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.

The following examples illustrate the invention, but they are not intended to limit it thereto:

Example 1 I 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.

Equally good results are obtained when carrying out the process with 2 parts of a sodium hydroxide solution (32.5%) at 20 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.

In each case, dull colored goods having a convenient handle are obtained.

Example 2 parts of the fabric described in Example 1 are dyed as described in Example 1 with a dyebath having the following composition:

3 parts of the acid wool dyestufi of the constitution Example 3 100 parts of the polyamide fabric which can be dyed with streaks only and which is described in Example 1,

3 parts of 2,4,6-tri- (1-aminobenzene-3potassium sulfonate)-s-triazine, 1 part of the condensation product from 6 mols of formaldehyde, 1 mol of melamine and 1 mol of the product of the addition of 30 mols of ethylene oxide to 1 mol of triethanolamine, prepared by condensation in an acid medium, and subsequently quaternized with dimethyl sulfate, 0.75 part of the product of the addition of 30 mols of ethylene oxide to 1 mol of nonyl phenol (30% strength), 3 parts of acetic acid (30% strength), 1000 parts of water, in a closed dyeing apparatus, while bringing the bath to the above temperature of 100 C. in the course of 1 hour, dyeing for 45 minutes at this temperature and finally dyeing for 15 minutes at 120 C.

After rinsing and drying, there is obtained a streakless, orange dyeing having good fastness properties.

Instead of the above described cation-active product, there can be used with the same success 1 part of a compound obtained by heating 213 g. of the product of the addition of 616 g. (14 mols) of ethylene oxide to 93 g. (1 mol) aniline with 28.2 g. of phenol and 60 cc. of formaldehyde solution of 30% strength in the presence of 40 cc. of sulfuric acid of 64% strength, while stirring and in the course of 50 minutes, to 100105 C., adjusting the pH-value of the solution to 9 by adding sodium hydroxide solution, and methylating the condensation prodnot at 5060 C. by adding 91 g. of dimethyl sulfate, whereupon 291 g. of the quaternary condensation product are obtained in the form of a solution.

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:

2 parts of the reactive dyestuff of the constitution 3 parts of 2,4,6 tri- (1 aminobenzene-3-potassium sulfonate)-s-triazine, 1 part of the condensation product from 12 mols of ethylene oxide and 1 mol of stearylamine (30% 2 parts of acetic acid (30% strength), 1000 parts of water.

After rinsing and drying, there is obtained a streakfree fast yellow dyeing corresponding in depth of shade and shade to an untreated dyeing.

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.

1.6 parts of 2,4,6-tri-(1-aminobenzene-3-potassium sulfonate)-s-triazine, 0.5 part of the condensation product of 12 mols of ethylene oxide and stearyl amine (30%), 3 parts of acetic acid (30% strength), and 1000 parts of water for 1 hour at 100 C., rinsed and dried.

There is obtained a red, streakfree and level dyeing corresponding to an untreated dyeing with regard to depth of shade and shade.

Instead of 1.6 parts of 2,4,6-tri-(1-aminobenZene-3- potassium sulfonate)-s-triazine, there may also be used 1.6 parts of 2,4,6-tri-(l-aminobenzene 2 sodium sulfonate)-s-triazine.

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:

1000 parts of water, 3 parts of 2,4,6-tri-( l-naphthylamino- 3,6-disulfonic acid)-s-triazine, 1 part of the compound CHzC1o 1 (R meaning soya bean oil), 0.25 part of a nonyl phenol oxethylated with 20 mols of ethylene oxide, and 3 parts of ace i a id (30% strength).

9 To the dyebath are then added through a sieve 3 parts of the complex chrome 2:1 dyestutr of 2 molecules of the following composition as aqueous solution, the Whole is heated within 30 minutes to 100 C. and dyeing is carried out for 60 minutes at this temperature.

The dyed goods are then rinsed and dried. There is obtained a level grey dyeing.

Without the addition of the dyeing assistant, 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).

2 parts of the dyestulf of the formula sO Na 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 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.

2. The process as defined in claim 1, in which 2,4,6- tri-( l-aminobenZene-4-sodium sulfonate)-s-triazine is used as the assistant for levelling the dyeing.

3. 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 compound having at least 3 hydroxyl groups.

4. The process as defined in claim 1, in which the compound of the formula is used as the assistant for levelling the dyeing.

5. 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.

6. 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.

7. The process as defined in claim ll wherein the assistant for levelling the dyeing is 2,4,6-tri-(l-aminobenzene- 3-potassium sulfonate s-triazine.

8. The process as defined in claim 1 wherein the assistant for levelling the dyeing is 2,4,6-tri-(l-naphthylamino- 3,6-disulfonic acid)-s-triazine.

9. The process as defined in claim ll wherein the assistant for levelling the dyeing is 2,4,6-tri-(l-aminobenzene- 2,4-disulfonic acid)-s-triazine.

References Cited by the Examiner UNITED STATES PATENTS 3,054,699 9/1962 Moyse 8-18 NORMAN G. TORCHIN, Primary Examiner.

J. HERBERT, Assistant Examiner.

Patent Citations
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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3481903 *May 15, 1967Dec 2, 1969Alelio Gaetano F DChelating compositions comprising products of aldehydes and triazine derivatives
US3519627 *Apr 9, 1968Jul 7, 1970Ashland Oil IncCarboxyl-containing ethers of amino-triazine/aldehyde condensates
US3615739 *Jul 30, 1969Oct 26, 1971Geigy Chem CorpFloor polishing composition containing substituted {11 -triazines
US3743477 *Jun 24, 1968Jul 3, 1973Sandoz LtdProcess for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes
US3890091 *Sep 6, 1973Jun 17, 1975Hoechst AgLevel dyeing of wool polyimine or polyamine and sulfonated phenylene amino-chlorotriazine treated
US3930795 *Sep 6, 1973Jan 6, 1976Hoechst AktiengesellschaftProcess for the level dyeing of wool
US4132850 *Jun 29, 1977Jan 2, 1979American Cyanamid CompanyTri-substituted triazines
US4183929 *Oct 13, 1978Jan 15, 1980American Cyanamid CompanyTri-substituted triazines
US4444563 *Sep 2, 1982Apr 24, 1984Ciba-Geigy CorporationDyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials
US4563189 *Feb 6, 1984Jan 7, 1986Wool Development International Ltd.Treatment of fibers with arylating agents to enhance disperse dyeability
US4587338 *Sep 13, 1984May 6, 1986Hoechst AktiengesellschaftPerfluoroalkyl esters of anthranilic acids
US4617390 *Jun 4, 1985Oct 14, 1986Basf AktiengesellschaftS-triazine derivatives
US4695632 *Feb 23, 1979Sep 22, 1987Bayer AktiengesellschaftQuaternary reactive compounds
US4886882 *Aug 18, 1986Dec 12, 1989Basf AktiengesellschaftHydroxyoxaalkylmelamines
US4950301 *Dec 22, 1988Aug 21, 1990Wool Development International LimitedKeratinous textile treatment with arylating compounds containing fibre reactive groups
US5571444 *Jan 11, 1996Nov 5, 1996Invicta Group Industries Pty Ltd.Textile treatment
US5792222 *Mar 3, 1997Aug 11, 1998Ciba Specialty Chemicals CorporationProcess for dyeing natural or synthetic polyamide fibre materials
US5922865 *Jun 2, 1998Jul 13, 1999Ciba Specialty Chemicals CorporationProcess for dyeing natural or synthetic polyamide fiber materials
US6022378 *Dec 15, 1998Feb 8, 2000Lenzing AktiengesellschaftProcess for the treatment of cellulose fibres and of assemblies made from these fibres
US6120562 *Mar 10, 1997Sep 19, 2000Basf AktiengesellschaftTriazine derivatives as fixers in coloring and as cross-linking agents
EP0118983A2 *Jan 30, 1984Sep 19, 1984Wool Development International LimitedTextile treatment
EP0174794A2 *Sep 4, 1985Mar 19, 1986Wool Development International LimitedTextile treatment
EP0175225A2 *Sep 6, 1985Mar 26, 1986Hoechst AktiengesellschaftFibre-reactive triazine compounds, process for their preparation and their use
WO1997035848A1 *Mar 10, 1997Oct 2, 1997Basf AktiengesellschaftTriazine derivatives as fixers in colouring and as cross-linking agents
Classifications
U.S. Classification8/493, 544/196, 8/924, 8/680, 544/204, 544/197, 544/211, 544/208, 8/566, 8/685, 544/194
International ClassificationD06P1/62, D06P3/24, D06P1/647, D06P1/607
Cooperative ClassificationD06P1/647, D06P3/246, D06P1/607, D06P1/628, Y10S8/924, D06P3/24
European ClassificationD06P3/24, D06P3/24N, D06P1/647, D06P1/62D, D06P1/607