US3084016A - Process for coloring cellulose textile materials with water-insoluble reactive dyestuffs - Google Patents

Process for coloring cellulose textile materials with water-insoluble reactive dyestuffs Download PDF

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US3084016A
US3084016A US4190A US419060A US3084016A US 3084016 A US3084016 A US 3084016A US 4190 A US4190 A US 4190A US 419060 A US419060 A US 419060A US 3084016 A US3084016 A US 3084016A
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water
textile material
cellulose textile
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insoluble
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US4190A
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Dawson Timothy Leslie
Rattee Ian Durham
Hutchinson Arthur
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves

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  • This invention relates to a coloring process and more particularly it relates to a coloring process for cellulose textile materials.
  • a process for coloring cellulose textile materials which comprises treatingthe cellulose textile material with one or more water-insoluble reactive dyestuffs, as hereinafter defined, and with an acid-binding agent.
  • the one or more water-insoluble reactive dyestuffs may be applied to the cellulose textile material by either a dyeing or a printing process.
  • a process for dyeing cellulose textile materials which comprises dyeing the cellulose textile material with an aqueous dispersion of one or more water-insoluble reactive dyestuifs, as hereinafter defined, in conjunction with a treatment with an acidabinding agent.
  • the treatment with the acid-binding agent may be carried out prior to, simultaneously with or subsequent to the dyeing of the cellulose textile material with the aque ous dispersion of one or more of the water-insoluble reactive dyestufis.
  • acid-binding agents which may be used in this process of the invention there may be mentioned sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium metasilioate, trisodium phosphate, tripotassium phosphate, magnesium oxide and ammonium hydroxide.
  • acid-binding agents for example sodium trichloroacetate and sodium bicarbonate, may be used which liberate an acid-binding agent when subjected to the action of heat or steam.
  • This process of the invention may be conveniently brought about by treating the cellulose textile material with an aqueous solution or suspension of the acid-binding agent and then immersing the so-treated cellulose textile material ina dyebath comprising a dispersion of one or more water-insoluble reactive dyestulfs, as hereinafter defined, at a temperature of between 0 and 100 C., removing the dyed cellulose textile material from the dyebath and if desired subjecting the dyed cellulose textile material to a treatment in a hot aqueous solution of soap.
  • the aqueous dispersion of the water-insoluble reactive dyestutf may be applied by padding to with an aqueous dispersion of one or more water-insoluble reactive dyestuffs, as hereinafter defined, which also contains an acid-binding agent, passing the so-treated cellu- 3,084,016 Patented Apr. 2, 1963 "Fee lose textile material through rollers, then, if desired drying the cellulose textile material at a suitable temperature, for example C., and then subjecting the cellulose textile material to the action of heat or steam.
  • a suitable temperature for example C.
  • the cellulose textile material can be dyed by immersing it in a dyebath comprising an aqueous dispersion of the one or more water-insoluble reactive dyestuffs which also contains an acid-binding agent, at a suitable temperature for example between 0 and C., and thereafter removing the cellulose textile material from the dyebath, if desired subjecting it to a treatment in a hot aqueous solution of soap and finally drying the dyed cellulose textile material.
  • a dyebath comprising an aqueous dispersion of the one or more water-insoluble reactive dyestuffs which also contains an acid-binding agent, at a suitable temperature for example between 0 and C.
  • this process of the invention may be conveniently brought about by applying the aqueous dispersion of the one or more water-insoluble reactive dyestuffs, as hereinafter defined, to the cellulose textile material by a dyeing or a padding method and subsequently immersing the colored cellulose textile material in an aqueous solution or suspension of the acid-binding agent, preferably at a temperature between 50 C. and 100 C., or alternatively the colored cellulose textile material may be padded with an aqueous solution or suspension of the acid-binding agent, the textile material dried and then subjected to the action of heat or steam.
  • the cellulose textile material can be dyed by immersing it in a dyebath comprising an aqueous dispersion of the one or more water-insoluble reactive dyestuffs, preferably at a temperature between 20 and 100 C., and after the cellulose textile material has absorbed some or all of the dyestulf, adding the acid-binding agent and continuing dyeing for a period at thesame or a different temperature.
  • a dyebath comprising an aqueous dispersion of the one or more water-insoluble reactive dyestuffs, preferably at a temperature between 20 and 100 C.
  • the concentration of the acid-binding agent present in the aqueous solution or suspension or in the aqueous dispersion of the dyestuffs is not critical but it is preferred to use between 0.1% and 10% of the acidabinding agent based on the total weight of the aqueous solution or suspension. If desired the aqueous solution or suspension of the acid binding agent may also contain further substances, tor example electrolytes such as sodium chloride and sodium sulphate.
  • the aqueous dispersion of the one or more water-insoluble reactive dyestuffs may also contain substances which are known to assist the application of dyestuffs to textile materials, for example sodium chloride, sodium sulphate, urea, dispersing agents, surface active agents, sodium alginate or an emulsion of an organic liquid, for example trichloroethylene in water.
  • substances which are known to assist the application of dyestuffs to textile materials for example sodium chloride, sodium sulphate, urea, dispersing agents, surface active agents, sodium alginate or an emulsion of an organic liquid, for example trichloroethylene in water.
  • a process for coloring cellulose textile materials which comprises printing the cellulose textile material with a printing paste containing one or more water-insoluble reactive dyestuffs, as hereinafter defined, the printing being carried out in conjunction with a treatment with an acid-binding agent.
  • the acidabinding agent may be applied to the cellulose textile material before applying the printing paste, or the acidbinding agent may be incorporated into the printing paste, or the printing paste may be applied to the cellulose textile material and the printed cellulose textile material subsequently treated with the acid-binding agent.
  • the cellulose textile material may be printed with the printing paste by any of the commonly known methods of applying printing pastes to textile materials, for example by means of roller printing, screen printing, block printing, spray printing or stencil printing.
  • the printing pastes used in this process of the invention may contain the commonly used adjuvants, for example urea, thickening agents, for example methyl cellulose, starch, locust bean gum, sodium alginate, water-in-oil emulsions, oil-in-water emulsionasurface active agents,
  • adjuvants for example urea
  • thickening agents for example methyl cellulose, starch, locust bean gum, sodium alginate, water-in-oil emulsions, oil-in-water emulsionasurface active agents
  • acid-binding agents which may be used in this process of the invention there may be mentioned sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium metasilicate, magnesium oxide and trisodium phosphate.
  • This process of the invention may be conveniently brought about by applying a printing paste containing one or more of the water-insoluble reactive dyestuffs, as hereinafter defined, to a cellulose textile material which has been impregnated with an acid-binding agent and thereafter subjecting the printed cellulose textile material to the action of heat or steam.
  • this process of the invention may be conveniently brought about by applying a printing paste containing one or more of the water-insoluble reactive dyestuffs and containing an acid-binding agent to the cellulose textile material and subsequently subjecting the printed cellulose textile material to the action of heat or steam.
  • this process of the invention may be conveniently brought about by applying a printing paste containing one or more of the water-insoluble reactive dyestuffs to the cellulose textile material and thereafter immersing the printed textile material in a hot aqueous solution or suspension of the acid-binding agent or alternatively impregnating the printed textile material with an aqueous solution or suspension of the acid-binding agent and subsequently subjecting the printed textile material to the action of heat or steam.
  • the printed textile material may, if desired, be dried, for example at a temperature between 20 and 100 C., before subjecting the printed textile material to the action of heat or steam.
  • a soaping treatment which may be carried out by immersing the colored cellulose textile materials for a short time, for example 15 minutes, in a hot aqueous solution of soap and/ or detergent, and subsequently rinsing the colored cellulose textile material in water before drying it.
  • water-insoluble reactive dyestufi there is meant a disperse or Water-insoluble dyestufi which is free from sulphonic acid and carboxylic acid groups and which contains (a) at least one reactive halogen atom or other reactive atom or group, that is to say a halogen atom or other group which is capable of reacting with the cellulose textile material whereby the dyestulf is attached to the cellulose textile material by a chemical bond and (b) one or more hydroxy groups.
  • water-insoluble reactive dyestutfs examples include waterinsoluble dyestuffs containing, besides the one or more hydroxy groups, at least one 1:3 :S-triazinyl radical carrying one or two chlorine or bromine atoms directly attached to the triazine ring, or at least one pyrimidyl radical carrying one, two or three chlorine or bromine atoms directly attached to the pyrimidine ring, or at least one 'y-halogeno-fi-hydroxypropylamino group, or at least one di-(y-halogeno-fi-hydroxypropyl)amino group, or at least one B-halogenoalkylsulphamyl group, or at least one ,9- halogenoethoxy group, or at least one ,B-halogenothioethane group, or at least one 'y-halogen-p-hydroxypropylsulphamyl group, or at least one chloracylamino group, or at least one
  • the water-insoluble dyestuffs of these classes may be for example nitro dyestuffs or dyestuffs of the azo, which may be monoazo or polyazo, anthraquinone or phthalocyanine series which are free from sulphonic and carboxylic acid groups and which may contain one or more coordinately bound metal atoms for example copper, chromium, nickel and cobalt.
  • alkyl preferably denotes a lower alkyl radical containing from 1 to 6 carbon atoms
  • ary preferably denotes a monocyclic aryl radical.
  • Water-insoluble dyestuffs containing a dichloro 01' dibromo-l :3 :S-triazinyl radical may be obtained by reacting one molecular proportion of a water-insoluble dyestufi containing a primary amino or secondary amino group with one molecular proportion of cyanuric chloride or cyanuric bromide.
  • Water-insoluble dyestuffs containing a monochloro or monobromo-1:3:5-triazinyl radical may be obtained by reacting one molecular proportion of a Water-insoluble dyestulf containing a primary amino or secondary amino group with one molecular proportion of "a triazine of the formula:
  • X is a chlorine or bromine atom and Y stands for an alkyl, aryl or amino group or for an organic radical containing a nitrogen, oxygen or sulphur atom through which it is linked to the triazine ring.
  • Water-insoluble dyestuffs containing a pyrimidyl radical carrying one or two chlorine or bromine atoms directly attached to the pyrimidine ring may be obtained by interacting substantially cquimolecular proportions of a water-insoluble dyestuif containing a primary amino or secondary amino group and a pyrimidine containing at least two chlorine or bromine atoms in the 2, 4, or 6 positions of the pyrimidine ring.
  • Water-insoluble dyestuffs containing at least one 7- halogeno-p-hydroxypropylsulphamyl or B-halogenoalkylsulphamyl group may be obtained by treating a waterinsoluble dyestufl? containing at least one sulphonchloride group with a 'y-halogeno-p-hydroxypropylamine or a B- halogenoalkylamine respectively.
  • Water-insoluble dyestufis containing at least one B- halogenoethoxy or p-halogenothioethane group may be obtained by treating a water-insoluble dyestuff containing at least one B-hydroxyethoxy or fl-hydroxythioethane group with a halogenating agent.
  • Water-insoluble dyestuffs containing at least one halogeno-fi-hydroxypropylamino or diOy-halogeno-fl-hydroxypropyl) amino group may be obtained by reacting a water-insoluble dyestufi containing one or more primary amino groups with epichlorohydrin or epibromohydrin and separating the mixture of products so obtained.
  • Water-insoluble dyestufls containing an epoxypropyl group may be obtained by reacting the corresponding dyestuffs containing a 'y-chloro-dhydroxypropyl group with potassium hydroxide.
  • Water-insoluble dyestuffs containing a vinylsulphone group may be obtained by treating with an alkali, for
  • Water-insoluble dyestuffs containing at least one acryloylamino or trichloroacryloylamino group may be obtained by reacting a water-insoluble dyestulf containing at least one primary amino group with acryloyl chloride or trichloroacryloyl chloride respectively.
  • Water-insoluble dyestutfs containing at least one vinyl- -sulphonylamino group may be obtained by reacting a water-insoluble dyestufi containing at least one primary amino group with B-chloroethane sulphonyl chloride when the vinylsulphonylamino group is directly obtained.
  • Water-insoluble azo dyestuffs containing at least one halogenoacyl group or at least one sulphonfluoride group, or at least one halogenoethylsulphonyl group may be obtained by coupling a diazotised amine with a coupling component, the amine and coupling component being free from sulphonic acid and carboxyl-ic acid groups and containing at least one halogenoacyl group, or at least one sulphonfluoride group or at least one halogenoethylsulphonyl group respectively.
  • the starting materials are so chosen that the resulting dyestuffs are free fromsulphonic and carboxylic acid groups and contain at least one 'hydroxy group.
  • suitable water-insoluble reactive dyestuffs which may be used in the process of the invention there may be mentioned Z-hydroxy-S- methyl -4' (4":6 -dichloro 1":3":5" triazin 2"- yla-mino)azobenzene, 2 chloro 4 ethanesulphonyl 4'- N 18 hydroxyethyl N ,8 (4:6" dichloro-1":3":5"- triazin-2" ylamino) ethylaminoazobenzene, 2 -.hydroxy 5 methyl 4' (4:6" dibromo 1":3":5"- triazin 2" ylamino) azobenzene, 2 hydroxy S-methyl- 4' (4" chloro 6" B hydroxyethylamino 1:3:5"- triazin 2" ylamino)azobenzene, 2 hydroxy S-methyl- 4 (4" chloro 6" anil-ino 1":3":
  • cellulose textile materials which may be dyed by the processes of therinvention there may be mentioned textile materials comprising natural and regenerated cellulose for example cotton, viscose rayon and linen.
  • Example 1 7 7 Example 2 n I 100 parts of bleached cotton yarn in hank form are treated in an open dye vessel for 1 /2 hours at a temperature between C. and C. in 3000 parts of water containing 1 part of 2-hydroxy-5-methyl-4'-[4"-chloro-6- di( ,B-hydroxyethyl) amino-l" 3" 5 -triazin-2 ylaminol azobenzene, 150 parts of sodium chloride and 30 parts of sodium metasilicate. T he'yarn is then rinsed in water, boiled in weak soap solution, rinsed again in water. and finally dried. i r
  • the yarn is colored a bright yellow shade which is fast to washing and to light.
  • Example 3 parts of spun viscose rayon fabric are treated on a dye jig for 1 /2 hours at a temperature between 80 C. and 90 C. in 1000 parts of water containing 1 part of 2- methyl-4-di-(fi-hydroxyethyl)amino-4' B chloroethylsulphamylazobenzene, 15 parts of sodium chloride and 10 parts of sodium metasilicate.
  • the fabric is then rinsed in water, boiled in weak soap solution, rinsed again in water and finally dried.
  • the fabric is colored a bright orange shade which is fast to washing and to light.
  • Example 4 100 parts of a bleached plain weave cotton fabric are padded with water containing 1.0% of-sodium metasilicate,
  • the cotton fabric is colored a bright blue shade which is fast to washing.
  • the printed cotton fabric is then dried at a temperature of 70 C. and subsequently treated for 30 minutes with steam at atmospheric pressure.
  • the printed cotton fabric is then rinsed in water, treated for minutes in an 0.2% aqueous solution of soap at 100 C., rinsed again in water and finally dried.
  • a bright reddish-blue print is obtained on the cotton fabric possessing excellent fastness to Washing and to rubbing.
  • the emulsion thickening used in the above example was obtained by adding 80 parts of white spirit to a rapidly stirred mixture of 7 /2 parts of an 8% aqueous solution of a modified locust bean gum, 5 parts of a 26.5% aqueous solution of an alkylated phenol/ethylene oxide condensate and 7 /2 parts of a aqueous solution of a fatty alcohol/ ethylene oxide condensate.
  • Example 6 In place of the printing paste used in Example 5 there is used a printing paste comprising Parts 2-methyl-4-di(fl-hydroxyethyl) amino-4-fl-chloroeth ylsulphamylazobenzene 1 Sodium m-nitrobenzenesulphonate 1 Sodium bicarbonate 2 Water 61 5% aqueous sodium alginate solution 35 A bright orange print is obtained on the cotton fabric possessing excellent fastness to washing and to rubbing.
  • Example 7 In place of the printing paste used in Example 5 there is used a printing paste comprising Parts 2 hydroxy-5-methyl-4'-[4-chloro-6"-di(fi-hydroxyethyl)amino 1":3":5 triazin-2"-ylamino]azobenzene 2 Sodium m-nitrobenzenesulphonate 1 Sodium bicarbonate 2 Water Emulsion thickening (obtained as described in Example 5) 70 A bright greenish-yellow print is obtained on the cotton fabric possessing excellent fastness to washing and to rubbing.
  • Example 8 A printing paste comprising Parts 1:4-bis('y-ch1oro [8 hydroxypropylamino)anthraquinone 1 Sodium m-nitrobenzenesulphonate 1 Water I 28 Emulsion thickening (obtained as described in Example 5)--- I 70 is printed on cotton fabric by roller printing. The printed cotton fabric is then dried at a temperature of 70% C. and the dry print padded through an aqueous solution containing 0.5% of sodium hydroxide. The printed cotton fabric is then dried at a temperature of 70% C. and treated for 10 minutes with steam at atmospheric pressure. The printed cotton fabric is then rinsed in water, immersed for 10 minutes in a 0.2% aqueous solution of soap at C., rinsed again in water and finally dried.
  • a bright blue print is obtained on the cotton fabric possessing excellent fastness to washing and to rubbing.
  • Example 9 A printing paste comprising Parts 2 hydroxy-5-methyl-4-(4"-6-dichloro-1":3:5"-
  • the cotton fabric is then printed on a roller printing machine with a printing paste comprising Parts 1:4 bis(7-chloro-fi-hydroxypropylamino) anthraquinone 3 Sodium m-nitrobenzenesulphonate 1 Water 26 Emulsion thickening (obtained as described in Example 5)- 70 and the printed cotton fabric is then dried at a temperature of 70 C. The dried print is then treated for 30 minutes with steam at atmospheric pressure, rinsed in water, immersed for 10 minutes in a 0.2% aqueous solution of soap at 100 C., rinsed again in water and finally dried.
  • a bright reddish-blue print is obtained on the cotton fabric possessing excellent fastness to washing and to rubhing.
  • Example 11 In place of the printing paste used in Example 5 there 1s used a printing paste comprising Parts 1 5 hydroxyethylaminol-('y-chloro-fi-hydroxypropylamino) anthraquinone 1 Sodium m-nitrobenzenesulphonate 1 Sodium carbona 2 Water 61 5% aqueous sodium alignate thickening 35 A bright reddish-blue print is obtained on the cotton fabric possessing excellent fastness to washing and to rubbing.
  • Example 12 In place of the printing paste used in Example there is used a printing paste comprising Parts 1 methylamino-4-('y-chloro-p-hydroxypropylamino) anthraquinone Sodium m-nitrobenzenesulphonate 1 Sodium carbonate 2 Water 26 Emulsion thickeningtobtained as described in Example 5) 70 A bright reddish-blue print is obtained on the cotton fabric possessing excellent fastness to washing and to rubbing.
  • Example 13 100 parts of bleached cotton yarn are immersed in a dyebath comprising 2 parts of 2-hydroxy-5-methyl-4- (4":6"-dichloro 1":3":'5" triazin 2" ylarnino) azobenzene dispersed in 3000' parts of water, which is held at a temperature of between 18 and 20 C. 90 parts of sodium chloride are then added, the yarn agitated in the dyebath for 30 minutes and 15 parts of sodium hydroxide are then added. After agitating for a further hour the cotton yarn is removed from the dyebath, rinsed in cold water, immersed for 15 minutes in a 0.3% aqueous solution of neutral detergent at 100 C., rinsed again in water and finally dried.
  • a dyebath comprising 2 parts of 2-hydroxy-5-methyl-4- (4":6"-dichloro 1":3":'5" triazin 2" ylarnino) azobenzene dispersed in 3000' parts of water, which is held at
  • the cotton yarn is colored a bright yellow shade possessing excellent fastness to washing.
  • Example 14 100 parts of spun viscose rayon fabric are padded at 1 8 C. in aqueous medium containing 1% of 2-hydroxy- 5 methyl-4'-(4:6"-dichloro-1":3:5"-triazin-2"-ylamino) azobenzene, 2% of sodium bicarbonate, 0.2% of a highly sulphonated oil and 0.1% of a fatty alcohol/ ethylene oxide condensate.
  • the fabric is squeezed between rollers until its weight is 200 parts then -it is exposed to steam at 100 C. for 5 minutes.
  • the colored fabric is then rinsed in water, immersed for 15 minutes in a 0.2% aqueous solution of soap, rinsed again in water and finally dried.
  • the viscose rayon fabric is colored a bright yellow shade possessing excellent fastness to washing.
  • Example 15 In place of the printing paste used in Example 8 there is used a printing paste comprising Parts 2-hydroxy 5-methyl-4'-[4"chloro-6"- dim-hydroxyethyl)amino 1:3:5 triazin 2 ylamino]azobenzene 2 Sodium m-nitrobenzenesulphonate 1
  • Water 27 Emulsion thickening (obtained as described in Example 5) 70 comprises dyeing a cellulose'textile material in a dyebath consisting essentially of an aqueous dispersion of a disperse, water-insoluble dyestuft free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby the dyestuff is attached to the cellulose textile material by a chemical bond, and which bath also contains an acid-binding agent and subjecting said textile material to the action of an elevated temperature to complete the reaction of said dyestuff with said textile material.
  • Process for coloring a cellulose textile material which comprises padding a cellulose textile material through an aqueous dispersion of a disperse, water-insoluble dyestuff free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby the dyestuff is attached to the cellulose textile material by a chemical bond, which dispersion also contains an acid-binding agent, and thereafter subjecting the cellulose textile material to the action of an elevated temperature to complete the reaction of said dyestuff with said textile material.
  • Process for coloring cellulose textile materials which comprises treating the cellulose textile material which has been pre-treated with an aqueous dispersion of a disperse, water-insoluble dyestuff free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby said dyestuff is attached to the cellulose textile material by a chemical bond, with an acid-binding agent, and thereafter subjecting the thus-treated cellulose textile material to the action of an elevated temperature to complete the reaction of said dyestuff with said textile material.
  • Process for coloring cellulose textile materials which comprises dyeing the cellulose textile material in a dyebath consisting essentially of an aqueous dispersion of a disperse, water-insoluble dyestufl free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby the dyest-ulf is attached to the cellulose textile material by a chemical bond, and, after at least a portion of said dyestulf in said dispersion has been absorbed by said textile material, adding an acid-binding agent and continuing dyeing for a further period, and subjecting said textile material to the action of an elevated temperature to complete the reaction of said dyestuif with said textile material.
  • Process for coloring cellulose textile materials which comprises printing a cellulose textile material, which has been treated with an acid-binding agent, with a printing paste containing a disperse, water-insoluble dyestuff free from sulfonic acid and car-b-oxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby the dyestuff is attached to the cellulose textile material by a chemical bond, and thereafter subjecting the cellulose textile material to the action of an elevated temperature to complete the reaction of said dyestuff with said textile material.
  • Process for coloring cellulose textile materials which comprises printing the cellulose textile material with a printing paste containing an acid-binding agent and a disperse, water-insoluble dyestufi free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby the dyestuif is attached to the cellulose textile material by a chemical bond, and thereafter subjecting the cellulose textile material to the action of an elevated temperature to complete the reaction of said dyestutf with said textile material.
  • Process for coloring cellulose textile materials which comprises printing the cellulose textile material with a printing paste containing a disperse, water-insoluble dyestufif free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile
  • a printing paste containing a disperse, water-insoluble dyestufif free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile

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Description

United States Patent 3 084,016 PROCESS FOR COLOIENG CELLULOSE TEXTILE MATERIALS WITH WATER-INSOLUBLE REAC- TIVE DYESTUFFS Timothy Leslie Dawson, Ian Durham Rattee, Irwin Seltzer, and Arthur Hutchinson Wyld, all of Manchester, England, assignors to Imperial Chemical Industries Limited, Millbank, London, England, a corporation of Great Britain No Drawing. Filed Jan. 25, 1960, Ser. No. 4,190 Claims priority, application Great Britain Feb. 10, 1959 9 Claims. (Ci. s-54.2
This invention relates to a coloring process and more particularly it relates to a coloring process for cellulose textile materials.
According to the invention there is provided a process for coloring cellulose textile materials which comprises treatingthe cellulose textile material with one or more water-insoluble reactive dyestuffs, as hereinafter defined, and with an acid-binding agent.
The one or more water-insoluble reactive dyestuffs may be applied to the cellulose textile material by either a dyeing or a printing process.
According to a further feature of the invention there is provided a process for dyeing cellulose textile materials which comprises dyeing the cellulose textile material with an aqueous dispersion of one or more water-insoluble reactive dyestuifs, as hereinafter defined, in conjunction with a treatment with an acidabinding agent.
The treatment with the acid-binding agent may be carried out prior to, simultaneously with or subsequent to the dyeing of the cellulose textile material with the aque ous dispersion of one or more of the water-insoluble reactive dyestufis.
.As examples of acid-binding agents which may be used in this process of the invention there may be mentioned sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium metasilioate, trisodium phosphate, tripotassium phosphate, magnesium oxide and ammonium hydroxide. If desired substances, for example sodium trichloroacetate and sodium bicarbonate, may be used which liberate an acid-binding agent when subjected to the action of heat or steam.
This process of the invention may be conveniently brought about by treating the cellulose textile material with an aqueous solution or suspension of the acid-binding agent and then immersing the so-treated cellulose textile material ina dyebath comprising a dispersion of one or more water-insoluble reactive dyestulfs, as hereinafter defined, at a temperature of between 0 and 100 C., removing the dyed cellulose textile material from the dyebath and if desired subjecting the dyed cellulose textile material to a treatment in a hot aqueous solution of soap.
If desired the cellulose textile material which has been treated with an aqueous solution or suspension of the acid-binding agent may be passed between rollers to remove excess aqueous solution or suspension of the acidbinding agent =and/ or dried before being treated with the aqueous dispersion of the water-insoluble reactive dyestuff.
Alternatively the aqueous dispersion of the water-insoluble reactive dyestutf may be applied by padding to with an aqueous dispersion of one or more water-insoluble reactive dyestuffs, as hereinafter defined, which also contains an acid-binding agent, passing the so-treated cellu- 3,084,016 Patented Apr. 2, 1963 "Fee lose textile material through rollers, then, if desired drying the cellulose textile material at a suitable temperature, for example C., and then subjecting the cellulose textile material to the action of heat or steam.
Alternatively the cellulose textile material can be dyed by immersing it in a dyebath comprising an aqueous dispersion of the one or more water-insoluble reactive dyestuffs which also contains an acid-binding agent, at a suitable temperature for example between 0 and C., and thereafter removing the cellulose textile material from the dyebath, if desired subjecting it to a treatment in a hot aqueous solution of soap and finally drying the dyed cellulose textile material. I
Alternatively this process of the invention may be conveniently brought about by applying the aqueous dispersion of the one or more water-insoluble reactive dyestuffs, as hereinafter defined, to the cellulose textile material by a dyeing or a padding method and subsequently immersing the colored cellulose textile material in an aqueous solution or suspension of the acid-binding agent, preferably at a temperature between 50 C. and 100 C., or alternatively the colored cellulose textile material may be padded with an aqueous solution or suspension of the acid-binding agent, the textile material dried and then subjected to the action of heat or steam.
Alternatively the cellulose textile material can be dyed by immersing it in a dyebath comprising an aqueous dispersion of the one or more water-insoluble reactive dyestuffs, preferably at a temperature between 20 and 100 C., and after the cellulose textile material has absorbed some or all of the dyestulf, adding the acid-binding agent and continuing dyeing for a period at thesame or a different temperature.
The concentration of the acid-binding agent present in the aqueous solution or suspension or in the aqueous dispersion of the dyestuffs is not critical but it is preferred to use between 0.1% and 10% of the acidabinding agent based on the total weight of the aqueous solution or suspension. If desired the aqueous solution or suspension of the acid binding agent may also contain further substances, tor example electrolytes such as sodium chloride and sodium sulphate.
The aqueous dispersion of the one or more water-insoluble reactive dyestuffs may also contain substances which are known to assist the application of dyestuffs to textile materials, for example sodium chloride, sodium sulphate, urea, dispersing agents, surface active agents, sodium alginate or an emulsion of an organic liquid, for example trichloroethylene in water.
According to a still further feature of the invention there is provided a process for coloring cellulose textile materials which comprises printing the cellulose textile material with a printing paste containing one or more water-insoluble reactive dyestuffs, as hereinafter defined, the printing being carried out in conjunction with a treatment with an acid-binding agent.
The acidabinding agent may be applied to the cellulose textile material before applying the printing paste, or the acidbinding agent may be incorporated into the printing paste, or the printing paste may be applied to the cellulose textile material and the printed cellulose textile material subsequently treated with the acid-binding agent.
The cellulose textile material may be printed with the printing paste by any of the commonly known methods of applying printing pastes to textile materials, for example by means of roller printing, screen printing, block printing, spray printing or stencil printing.
The printing pastes used in this process of the invention may contain the commonly used adjuvants, for example urea, thickening agents, for example methyl cellulose, starch, locust bean gum, sodium alginate, water-in-oil emulsions, oil-in-water emulsionasurface active agents,
sodium m-nitrobenzene sulphonate, and organic liquids, for example ethanol.
As examples of acid-binding agents which may be used in this process of the invention there may be mentioned sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium metasilicate, magnesium oxide and trisodium phosphate.
This process of the invention may be conveniently brought about by applying a printing paste containing one or more of the water-insoluble reactive dyestuffs, as hereinafter defined, to a cellulose textile material which has been impregnated with an acid-binding agent and thereafter subjecting the printed cellulose textile material to the action of heat or steam.
Alternatively this process of the invention may be conveniently brought about by applying a printing paste containing one or more of the water-insoluble reactive dyestuffs and containing an acid-binding agent to the cellulose textile material and subsequently subjecting the printed cellulose textile material to the action of heat or steam.
Alternatively this process of the invention may be conveniently brought about by applying a printing paste containing one or more of the water-insoluble reactive dyestuffs to the cellulose textile material and thereafter immersing the printed textile material in a hot aqueous solution or suspension of the acid-binding agent or alternatively impregnating the printed textile material with an aqueous solution or suspension of the acid-binding agent and subsequently subjecting the printed textile material to the action of heat or steam.
After applying the printing paste to the cellulose textile material the printed textile material may, if desired, be dried, for example at a temperature between 20 and 100 C., before subjecting the printed textile material to the action of heat or steam.
At the conclusion of dyeing and/or printing processes it is preferred to subject the so-colored cellulose textile materials to a soaping treatment, which may be carried out by immersing the colored cellulose textile materials for a short time, for example 15 minutes, in a hot aqueous solution of soap and/ or detergent, and subsequently rinsing the colored cellulose textile material in water before drying it.
By the term water-insoluble reactive dyestufi there is meant a disperse or Water-insoluble dyestufi which is free from sulphonic acid and carboxylic acid groups and which contains (a) at least one reactive halogen atom or other reactive atom or group, that is to say a halogen atom or other group which is capable of reacting with the cellulose textile material whereby the dyestulf is attached to the cellulose textile material by a chemical bond and (b) one or more hydroxy groups. Examples of classes of such water-insoluble reactive dyestutfs include waterinsoluble dyestuffs containing, besides the one or more hydroxy groups, at least one 1:3 :S-triazinyl radical carrying one or two chlorine or bromine atoms directly attached to the triazine ring, or at least one pyrimidyl radical carrying one, two or three chlorine or bromine atoms directly attached to the pyrimidine ring, or at least one 'y-halogeno-fi-hydroxypropylamino group, or at least one di-(y-halogeno-fi-hydroxypropyl)amino group, or at least one B-halogenoalkylsulphamyl group, or at least one ,9- halogenoethoxy group, or at least one ,B-halogenothioethane group, or at least one 'y-halogen-p-hydroxypropylsulphamyl group, or at least one chloracylamino group, or at least one halogenoacyl group, or at least one sulphonfluoride group, or at least one vinylsulphonylamino group, or at least one halogenoethylsulphonyl group, or at least one thiocyano group, or at least one alkylor arylsulphonyloxyalkylsulphonyl group, or at least one alkylor arylsulphonyloxyalkylarninosuphonyl group, or at least one alkylor arylsulphonyloxyalkylamino group, or at least one alkylor arylsulphonyloxyalkoxy group, or at least one alkylor arylsulphonyoxyalkylaminocarbonyl group, or at least one acryloylamino or trichloroacryloylamino group, or at least one vinylsulphonyl group, or at least one epoxypropyl group. The water-insoluble dyestuffs of these classes may be for example nitro dyestuffs or dyestuffs of the azo, which may be monoazo or polyazo, anthraquinone or phthalocyanine series which are free from sulphonic and carboxylic acid groups and which may contain one or more coordinately bound metal atoms for example copper, chromium, nickel and cobalt.
In the above groups halogeno denotes chloro or bromo, alkyl preferably denotes a lower alkyl radical containing from 1 to 6 carbon atoms, and ary preferably denotes a monocyclic aryl radical.
Water-insoluble dyestuffs containing a dichloro 01' dibromo-l :3 :S-triazinyl radical may be obtained by reacting one molecular proportion of a water-insoluble dyestufi containing a primary amino or secondary amino group with one molecular proportion of cyanuric chloride or cyanuric bromide. Water-insoluble dyestuffs containing a monochloro or monobromo-1:3:5-triazinyl radical may be obtained by reacting one molecular proportion of a Water-insoluble dyestulf containing a primary amino or secondary amino group with one molecular proportion of "a triazine of the formula:
wherein X is a chlorine or bromine atom and Y stands for an alkyl, aryl or amino group or for an organic radical containing a nitrogen, oxygen or sulphur atom through which it is linked to the triazine ring.
Water-insoluble dyestuffs containing a pyrimidyl radical carrying one or two chlorine or bromine atoms directly attached to the pyrimidine ring may be obtained by interacting substantially cquimolecular proportions of a water-insoluble dyestuif containing a primary amino or secondary amino group and a pyrimidine containing at least two chlorine or bromine atoms in the 2, 4, or 6 positions of the pyrimidine ring. As examples of such pyrimidines there may be mentioned 2:4:6-trichloropyrimidine, 2:4: 5 fi-tetrachloropyrimidine, 2 4-dibromopyrimidine, 2:4-dichloro-6-methylpyrimidine, 2:4-dichlorofi-methoxypyrimidine, 2 4 6-tribromopyrimidine, 2 :4-dichloro-G-phenylpyrimidine, 2:4-dichloro-6 nitropyrirnidine, 2 4-dichloro-S-cyanopyrimidine, 2 :4: G-trichloro-S- cyanopyrimidine, 2:4-dichloro 6 hydroxypyrimidine, 2:4:6-trichloro-S-nitropyrimidine and 2:4dichloro-5-nitro-6-methylpyrimidine.
Water-insoluble dyestuffs containing at least one 7- halogeno-p-hydroxypropylsulphamyl or B-halogenoalkylsulphamyl group may be obtained by treating a waterinsoluble dyestufl? containing at least one sulphonchloride group with a 'y-halogeno-p-hydroxypropylamine or a B- halogenoalkylamine respectively.
Water-insoluble dyestufis containing at least one B- halogenoethoxy or p-halogenothioethane group may be obtained by treating a water-insoluble dyestuff containing at least one B-hydroxyethoxy or fl-hydroxythioethane group with a halogenating agent.
Water-insoluble dyestuffs containing at least one halogeno-fi-hydroxypropylamino or diOy-halogeno-fl-hydroxypropyl) amino group may be obtained by reacting a water-insoluble dyestufi containing one or more primary amino groups with epichlorohydrin or epibromohydrin and separating the mixture of products so obtained.
Water-insoluble dyestufls containing an epoxypropyl group may be obtained by reacting the corresponding dyestuffs containing a 'y-chloro-dhydroxypropyl group with potassium hydroxide.
Water-insoluble dyestuffs containing a vinylsulphone group may be obtained by treating with an alkali, for
example potassium hydroxide, the corresponding dyehydroxyalkoxy or hydroxyalkylaminocar-bonyl group respectivel with an alkylor arylsulphonhalide respectively. Water-insoluble dyestuffs containing at least one acryloylamino or trichloroacryloylamino group may be obtained by reacting a water-insoluble dyestulf containing at least one primary amino group with acryloyl chloride or trichloroacryloyl chloride respectively.
Water-insoluble dyestutfs containing at least one vinyl- -sulphonylamino group may be obtained by reacting a water-insoluble dyestufi containing at least one primary amino group with B-chloroethane sulphonyl chloride when the vinylsulphonylamino group is directly obtained.
Water-insoluble azo dyestuffs containing at least one halogenoacyl group or at least one sulphonfluoride group, or at least one halogenoethylsulphonyl group may be obtained by coupling a diazotised amine with a coupling component, the amine and coupling component being free from sulphonic acid and carboxyl-ic acid groups and containing at least one halogenoacyl group, or at least one sulphonfluoride group or at least one halogenoethylsulphonyl group respectively.
In all the above methods for preparing the waterinsoluble dyestuffs used in the processes of the invention the starting materials are so chosen that the resulting dyestuffs are free fromsulphonic and carboxylic acid groups and contain at least one 'hydroxy group.
As specific examples of suitable water-insoluble reactive dyestuffs which may be used in the process of the invention there may be mentioned Z-hydroxy-S- methyl -4' (4":6 -dichloro 1":3":5" triazin 2"- yla-mino)azobenzene, 2 chloro 4 ethanesulphonyl 4'- N 18 hydroxyethyl N ,8 (4:6" dichloro-1":3":5"- triazin-2" ylamino) ethylaminoazobenzene, 2 -.hydroxy 5 methyl 4' (4:6" dibromo 1":3":5"- triazin 2" ylamino) azobenzene, 2 hydroxy S-methyl- 4' (4" chloro 6" B hydroxyethylamino 1:3:5"- triazin 2" ylamino)azobenzene, 2 hydroxy S-methyl- 4 (4" chloro 6" anil-ino 1":3":5 triazin 2"- ylamino)azobenzer1e, 2 hydroxy 5 methyl 4' (4"- chloro 6" amino l":3":5" triazin 2" ylamino)- azobenzene, 2 chloro 4 ethanesulphonyl 4' N 8- hydroxyethyl N 8 (4" chloro 6" hydroxy- 1:3:5"-triazin-2" ylamino) ethylaminoazobenzene, 2- hydroxy 5 methyl 4 (4" bromo 6" NzN di- (;3 hydroXyethyDamino 1:3:5 triazin 2"- ylamino)azobenzene, 2 hydroxy 5 methyl 4 (4"- chloro 6" phenyl 1":3":5" triazin 2" ylamino)- azobenzene, 1 4' (4" chloro 6" hydroxy-1":3:5"- triazin 2" ylamino)anilinoanthraquinone, 4' (4"- chloro 6" hydroxytriazin 2" ylamino) 2:4 dinitrodiphenylamine, 3 (4 chloro 6" hydroxyl":3":5" triazin 2" ylamino) 2 nitro 4 trifluoromethyldiphenylarnine, 2 hydroxy 5 methyl 4'- (4:6" dichloropyrimidine 2" ylamino)azobenzene, 4 nitro 4 N:N di('y chloro B hydroxypropyl)- amino azobenzene, 1:4 bis(- chloro e hydroxypropylamino)anthraquinone, 4 ,B-chloroethylsulphamyh phenylazo 4 B hydroxyethylaminonaphthalene, 4 chloroethylsulphamyl 2 methyl 5' N ethyl N flhydroxyethylaminoazobenzene, 2 chloro 4 B chloroethylsulphamyl 2' methyl 5' di(beta hydroxyethyD- aminoazobenzene, 1 13 hydroxyethyl 4 [3 chloroethylamino anthraquinone,- 1:4 (4":65- dichloro- 1":3,":5 triazin 2 ylamino)phenylazo 2 naphthol, 1 amino 2 fi bromoethoxy 4 hydroxyanthraquinone, 1 amino 4 hydroxy 2 5 (5' chloroethoxy) ethoxy-anthnaquinone and 1- amino-4-hydroxy-2- pflabromoethoxy) ethoxyanthraquinone.
As examples of cellulose textile materials which may be dyed by the processes of therinvention there may be mentioned textile materials comprising natural and regenerated cellulose for example cotton, viscose rayon and linen.
By the processes of the invention there are obtained on cellulose textile materials level colorations in a wide range of bright shades which have excellent fastness to wet treatments suchas washing, to rubbing and to acids, and the colorations so obtained have much better fast-ness to Wet treatments than the colorations similarly obtained from the corresponding dyestuffs which do not contain a hydroxy group or groups.
The invention is illustrated but not limited by the following examples in which the parts and percentages are by weight:
Example 1 7 7 Example 2 n I 100 parts of bleached cotton yarn in hank form are treated in an open dye vessel for 1 /2 hours at a temperature between C. and C. in 3000 parts of water containing 1 part of 2-hydroxy-5-methyl-4'-[4"-chloro-6- di( ,B-hydroxyethyl) amino-l" 3" 5 -triazin-2 ylaminol azobenzene, 150 parts of sodium chloride and 30 parts of sodium metasilicate. T he'yarn is then rinsed in water, boiled in weak soap solution, rinsed again in water. and finally dried. i r
The yarn is colored a bright yellow shade which is fast to washing and to light.
Example 3 parts of spun viscose rayon fabric are treated on a dye jig for 1 /2 hours at a temperature between 80 C. and 90 C. in 1000 parts of water containing 1 part of 2- methyl-4-di-(fi-hydroxyethyl)amino-4' B chloroethylsulphamylazobenzene, 15 parts of sodium chloride and 10 parts of sodium metasilicate. The fabric is then rinsed in water, boiled in weak soap solution, rinsed again in water and finally dried.
The fabric is colored a bright orange shade which is fast to washing and to light.
Example 4 100 parts of a bleached plain weave cotton fabric are padded with water containing 1.0% of-sodium metasilicate,
0.2% of a highly sulphonated oil, 1.0% of 1:4-biS('ychloro-fl-hydroxypropylamino)anthraquinone and 0. 1 of a fatty alcohol/ethylene oxide condensate and the fabric is then squeezed between rollers until its weight is 200 parts. The fabric is then rolled up andaged at a temperaturebetween 80 C. and 90 C. for 2 hours. The fabric is then rinsed in water, scoured for 15 minutes in a boiling i 0.3% aqueous solution of a neutral detergent, rinsed again in water and finally dried.
The cotton fabric is colored a bright blue shade which is fast to washing.
is printed on cotton fabric by roller printing. The printed cotton fabric is then dried at a temperature of 70 C. and subsequently treated for 30 minutes with steam at atmospheric pressure. The printed cotton fabric is then rinsed in water, treated for minutes in an 0.2% aqueous solution of soap at 100 C., rinsed again in water and finally dried.
A bright reddish-blue print is obtained on the cotton fabric possessing excellent fastness to Washing and to rubbing.
I The emulsion thickening used in the above example was obtained by adding 80 parts of white spirit to a rapidly stirred mixture of 7 /2 parts of an 8% aqueous solution of a modified locust bean gum, 5 parts of a 26.5% aqueous solution of an alkylated phenol/ethylene oxide condensate and 7 /2 parts of a aqueous solution of a fatty alcohol/ ethylene oxide condensate.
Example 6 In place of the printing paste used in Example 5 there is used a printing paste comprising Parts 2-methyl-4-di(fl-hydroxyethyl) amino-4-fl-chloroeth ylsulphamylazobenzene 1 Sodium m-nitrobenzenesulphonate 1 Sodium bicarbonate 2 Water 61 5% aqueous sodium alginate solution 35 A bright orange print is obtained on the cotton fabric possessing excellent fastness to washing and to rubbing.
Example 7 In place of the printing paste used in Example 5 there is used a printing paste comprising Parts 2 hydroxy-5-methyl-4'-[4-chloro-6"-di(fi-hydroxyethyl)amino 1":3":5 triazin-2"-ylamino]azobenzene 2 Sodium m-nitrobenzenesulphonate 1 Sodium bicarbonate 2 Water Emulsion thickening (obtained as described in Example 5) 70 A bright greenish-yellow print is obtained on the cotton fabric possessing excellent fastness to washing and to rubbing.
Example 8 A printing paste comprising Parts 1:4-bis('y-ch1oro [8 hydroxypropylamino)anthraquinone 1 Sodium m-nitrobenzenesulphonate 1 Water I 28 Emulsion thickening (obtained as described in Example 5)--- I 70 is printed on cotton fabric by roller printing. The printed cotton fabric is then dried at a temperature of 70% C. and the dry print padded through an aqueous solution containing 0.5% of sodium hydroxide. The printed cotton fabric is then dried at a temperature of 70% C. and treated for 10 minutes with steam at atmospheric pressure. The printed cotton fabric is then rinsed in water, immersed for 10 minutes in a 0.2% aqueous solution of soap at C., rinsed again in water and finally dried.
A bright blue print is obtained on the cotton fabric possessing excellent fastness to washing and to rubbing.
Example 9 A printing paste comprising Parts 2 hydroxy-5-methyl-4-(4"-6-dichloro-1":3:5"-
triazin-2-ylamino)azobenzene 1 Sodium m-nitrobenzenesulphonate 1 Water 28 Emulsion thickening (obtained as described in Example 5)---- 70 Example 10 Cotton fabric is impregnated with an 0.5% aqueous solution of sodium hydroxide, squeezed between rollers,
.until the weight of solution retained by the fabric is equal to the original Weight of the fabric and finally dried. The cotton fabric is then printed on a roller printing machine with a printing paste comprising Parts 1:4 bis(7-chloro-fi-hydroxypropylamino) anthraquinone 3 Sodium m-nitrobenzenesulphonate 1 Water 26 Emulsion thickening (obtained as described in Example 5)- 70 and the printed cotton fabric is then dried at a temperature of 70 C. The dried print is then treated for 30 minutes with steam at atmospheric pressure, rinsed in water, immersed for 10 minutes in a 0.2% aqueous solution of soap at 100 C., rinsed again in water and finally dried.
A bright reddish-blue print is obtained on the cotton fabric possessing excellent fastness to washing and to rubhing.
Example 11 In place of the printing paste used in Example 5 there 1s used a printing paste comprising Parts 1 5 hydroxyethylaminol-('y-chloro-fi-hydroxypropylamino) anthraquinone 1 Sodium m-nitrobenzenesulphonate 1 Sodium carbona 2 Water 61 5% aqueous sodium alignate thickening 35 A bright reddish-blue print is obtained on the cotton fabric possessing excellent fastness to washing and to rubbing.
Example 12 In place of the printing paste used in Example there is used a printing paste comprising Parts 1 methylamino-4-('y-chloro-p-hydroxypropylamino) anthraquinone Sodium m-nitrobenzenesulphonate 1 Sodium carbonate 2 Water 26 Emulsion thickeningtobtained as described in Example 5) 70 A bright reddish-blue print is obtained on the cotton fabric possessing excellent fastness to washing and to rubbing.
Example 13 100 parts of bleached cotton yarn are immersed in a dyebath comprising 2 parts of 2-hydroxy-5-methyl-4- (4":6"-dichloro 1":3":'5" triazin 2" ylarnino) azobenzene dispersed in 3000' parts of water, which is held at a temperature of between 18 and 20 C. 90 parts of sodium chloride are then added, the yarn agitated in the dyebath for 30 minutes and 15 parts of sodium hydroxide are then added. After agitating for a further hour the cotton yarn is removed from the dyebath, rinsed in cold water, immersed for 15 minutes in a 0.3% aqueous solution of neutral detergent at 100 C., rinsed again in water and finally dried.
The cotton yarn is colored a bright yellow shade possessing excellent fastness to washing.
In place of the 90 parts of sodium chloride used in the above example there may be used 90 parts of sodium sulphate when a similar result is obtained.
Example 14 100 parts of spun viscose rayon fabric are padded at 1 8 C. in aqueous medium containing 1% of 2-hydroxy- 5 methyl-4'-(4:6"-dichloro-1":3:5"-triazin-2"-ylamino) azobenzene, 2% of sodium bicarbonate, 0.2% of a highly sulphonated oil and 0.1% of a fatty alcohol/ ethylene oxide condensate. The fabric is squeezed between rollers until its weight is 200 parts then -it is exposed to steam at 100 C. for 5 minutes. The colored fabric is then rinsed in water, immersed for 15 minutes in a 0.2% aqueous solution of soap, rinsed again in water and finally dried.
The viscose rayon fabric is colored a bright yellow shade possessing excellent fastness to washing.
Example 15 In place of the printing paste used in Example 8 there is used a printing paste comprising Parts 2-hydroxy 5-methyl-4'-[4"chloro-6"- dim-hydroxyethyl)amino 1:3:5 triazin 2 ylamino]azobenzene 2 Sodium m-nitrobenzenesulphonate 1 Water 27 Emulsion thickening (obtained as described in Example 5) 70 comprises dyeing a cellulose'textile material in a dyebath consisting essentially of an aqueous dispersion of a disperse, water-insoluble dyestuft free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby the dyestuff is attached to the cellulose textile material by a chemical bond, and which bath also contains an acid-binding agent and subjecting said textile material to the action of an elevated temperature to complete the reaction of said dyestuff with said textile material.
4. Process for coloring a cellulose textile material which comprises padding a cellulose textile material through an aqueous dispersion of a disperse, water-insoluble dyestuff free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby the dyestuff is attached to the cellulose textile material by a chemical bond, which dispersion also contains an acid-binding agent, and thereafter subjecting the cellulose textile material to the action of an elevated temperature to complete the reaction of said dyestuff with said textile material.
5. Process for coloring cellulose textile materials which comprises treating the cellulose textile material which has been pre-treated with an aqueous dispersion of a disperse, water-insoluble dyestuff free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby said dyestuff is attached to the cellulose textile material by a chemical bond, with an acid-binding agent, and thereafter subjecting the thus-treated cellulose textile material to the action of an elevated temperature to complete the reaction of said dyestuff with said textile material.
6. Process for coloring cellulose textile materials which comprises dyeing the cellulose textile material in a dyebath consisting essentially of an aqueous dispersion of a disperse, water-insoluble dyestufl free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby the dyest-ulf is attached to the cellulose textile material by a chemical bond, and, after at least a portion of said dyestulf in said dispersion has been absorbed by said textile material, adding an acid-binding agent and continuing dyeing for a further period, and subjecting said textile material to the action of an elevated temperature to complete the reaction of said dyestuif with said textile material.
7. Process for coloring cellulose textile materials which comprises printing a cellulose textile material, which has been treated with an acid-binding agent, with a printing paste containing a disperse, water-insoluble dyestuff free from sulfonic acid and car-b-oxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby the dyestuff is attached to the cellulose textile material by a chemical bond, and thereafter subjecting the cellulose textile material to the action of an elevated temperature to complete the reaction of said dyestuff with said textile material.
8. Process for coloring cellulose textile materials which comprises printing the cellulose textile material with a printing paste containing an acid-binding agent and a disperse, water-insoluble dyestufi free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile material, whereby the dyestuif is attached to the cellulose textile material by a chemical bond, and thereafter subjecting the cellulose textile material to the action of an elevated temperature to complete the reaction of said dyestutf with said textile material.
9. Process for coloring cellulose textile materials which comprises printing the cellulose textile material with a printing paste containing a disperse, water-insoluble dyestufif free from sulfonic acid and carboxylic acid groups and containing a hydroxy substituent and a group which is capable of reacting with said cellulose textile References Cited in the file of this patent UNITED STATES PATENTS 2,741,532 Guthrie Apr. 10, 1956 2,895,785 Alsberg et al. July 21, 1959 2,944,871 Atkinson et al. July 12, 1960 2,978,289 Barker et al. Apr. 4, 1961 2,981,588 Haber Apr. 25, 1961 2,995,412 Kleb Aug. 8, 1961 3,009,920 Jaeger et al. Nov. 21, 1961

Claims (1)

1. PROCESS FOR COLORING CELLULOSE TEXTILE MATERIAL WHICH COMPRISES TREATING THE CELLULOSE TEXTILE MATERIAL WITH A DISPERSE, WATER-INSOLUBLE DYESTUFF FREE FROM SULFONIC ACID ABD CARBOXYLIC ACID GROUPS AND CONTAINING A HYDROXY SUBSTITUENT A GROUP WHICH IS CAPABLE OF REACTING WITH SAID CELLULOSE TEXTILE MATERIAL, WHEREBY THE DYESTUFF IS ATTACHED TO THE CELLULOSE TEXTILE MATERIAL BY A CHEMICAL BOND, AND WITH AN ACID-BINDING AGENT AND SUBJECTING SAID TEXTILE MATERIAL TO THE ACTION OF AN ELEVATED TEMPERATURE TO COMPLETE THE REACTION OF SAID DYESTUFF WITH SAID TEXTILE MATERIAL.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3220793A (en) * 1963-07-25 1965-11-30 Ici Ltd Coloration process
US3261827A (en) * 1961-03-07 1966-07-19 Bayer Ag Organic fiber reactive dyestuffs
US3288551A (en) * 1963-08-08 1966-11-29 Ciba Geigy Corp Process for the coloring of fiber blends of polyester and native or regenerated cellulose

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1619503A1 (en) * 1967-01-10 1970-09-10 Hoechst Ag Process for fixing reactive dyes on textile materials made of native or regenerated cellulose
CN118121892A (en) * 2023-06-29 2024-06-04 烟台大学 Material for chromium removing and ammonia reducing agent for chromium-containing collagen solution

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2741532A (en) * 1956-04-10 Hoasox
US2895785A (en) * 1959-07-21 Naoas
US2944871A (en) * 1957-10-04 1960-07-12 Ici Ltd New colouring process
US2978289A (en) * 1957-08-07 1961-04-04 Ici Ltd Process for coloring cellulose with new triazine dyestuffs
US2981588A (en) * 1959-11-10 1961-04-25 Allied Textile Printers Inc Colored flocked fabrics
US2995412A (en) * 1958-07-08 1961-08-08 Bayer Ag Process for dyeing and printing of textile materials containing hydroxyl groups
US3009920A (en) * 1957-09-25 1961-11-21 Ciba Ltd Epichlorohydrin-containing phthalocyanine dyestuffs

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1041912B (en) * 1954-11-29 1958-10-30 Ici Ltd Process for dyeing or printing cellulosic textile fabrics

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2741532A (en) * 1956-04-10 Hoasox
US2895785A (en) * 1959-07-21 Naoas
US2978289A (en) * 1957-08-07 1961-04-04 Ici Ltd Process for coloring cellulose with new triazine dyestuffs
US3009920A (en) * 1957-09-25 1961-11-21 Ciba Ltd Epichlorohydrin-containing phthalocyanine dyestuffs
US2944871A (en) * 1957-10-04 1960-07-12 Ici Ltd New colouring process
US2995412A (en) * 1958-07-08 1961-08-08 Bayer Ag Process for dyeing and printing of textile materials containing hydroxyl groups
US2981588A (en) * 1959-11-10 1961-04-25 Allied Textile Printers Inc Colored flocked fabrics

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3261827A (en) * 1961-03-07 1966-07-19 Bayer Ag Organic fiber reactive dyestuffs
US3220793A (en) * 1963-07-25 1965-11-30 Ici Ltd Coloration process
US3288551A (en) * 1963-08-08 1966-11-29 Ciba Geigy Corp Process for the coloring of fiber blends of polyester and native or regenerated cellulose

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