US3787179A - Process for the manufacture of insoluble azo dyestuffs on cellulose fibers - Google Patents

Process for the manufacture of insoluble azo dyestuffs on cellulose fibers Download PDF

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Publication number
US3787179A
US3787179A US00206904A US3787179DA US3787179A US 3787179 A US3787179 A US 3787179A US 00206904 A US00206904 A US 00206904A US 3787179D A US3787179D A US 3787179DA US 3787179 A US3787179 A US 3787179A
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United States
Prior art keywords
amino
diazo
cellulose fibers
water
methyl
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Expired - Lifetime
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US00206904A
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English (en)
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R Lowenfeld
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Hoechst AG
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Hoechst AG
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/68—Preparing azo dyes on the material
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/922—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons

Definitions

  • the organic solvent a hydrocarbon which may be halogenated, ar- [56] References Cited omatic or 'cycloaliphatic.
  • the present invention relates to a process for the dyeing .of Cellulose fibers which permits to reduce the water consumption as compared to conventional processes to a large extent and thus to avoid the problems of eliminating the sewage .water.
  • insoluble azo dyestuffs are manufactured in a continuous manner on woven or knitted fabrics or cellulose fibers such that the material to be dyed is first impregnated with the aqueous, alkaline solution of a coupling component, dried and then 'treated with the aqueous, slightly acidic solution of a diazo component.
  • the dyestuff is formed when the material to be dyed passes through the solution of the diazo component or during the subsequent passage three to eight baths continuously with hot, organic solvents.
  • the dyestuff pigments formed on the ceulose fiber should have a limited solubility in the solvents used. In the organic solvents used according to this process, slight amounts of water may also be emulsified if necessary. Finally, the dyeling produced is dried and the solvent recovered.
  • the insoluble azo dyestufi is manufactured from the coupling component and the diazo-amino compound or the antidiazotate of a primary aromatic amine.
  • release of the diazonium compound capable of coupling which is mandatory before the dyestuff coupling may be carried out in the hot solvent, to which an organic acid miscible with the corresponding solvent is added for this purpose.
  • an organic acid miscible with the corresponding solvent is added for this purpose.
  • the material is first passed through aqueous rinsing baths and the dyeing is then treated for being finished with alkaline, aqueous solutions containing detergents at the boiling temperature. Finally, the dyed articles are dried.
  • Insoluble azo dyestuffs may also be manufactured on cellulose fibers in such a manner that in the aqueous, alkaline solution of a coupling component the diazoamino compound of a primary aromatic amine is simultaneously dissolved, both components are applied together to the material by impregnation and the dyestuff formation is achieved by treating the textile material thus impregnated with an acid which is diluted with water, by acidic steaming or by exposing it to the effect of dry heat with or without the addition of acidyielding agents. Then, the dyeing is finished by rinsing and aftertreating in aqueous baths and finally dried.
  • the textile material for example, a fabric web
  • the textile material is impregnated with the aqueous, alkaline solution of a coupling component, dried and passed through the aqueous solution of a diazonium compound capable of coupling which liquor contains alkali-binding agents inthe form of a voltatile, organic acid.
  • the dyeing obtained is then treated in the moist or dried state by means of a passage through bodiment, the coupling component and the diazo component in form of a diazoamino compound capable of being split up or of an anti-diazotate are applied in aqueous, alkaline solution to a fabric web at the same time.
  • the impregnated material is passed in the moist or dried state through three to eight baths with hot, organic solvents, the first bath thereof containing an addition of a volatile, organic acid.
  • the water consumption in the dyeing and finishing of the dyeings according to the invention is reduced to a minimum as compared to the water amounts which are required in the manufacture of corresponding insoluble azo dyestuffs on cellulose fibers according to known processes.
  • coupling components are used which have a slight to medium substantivity towards the textile material.
  • the arylides of the B-hydroxy-naphthoic acid for example 2,3-hydroxynaphthoic acid anilide, l-( 2 3"-hydroxy-naphthoyl-amino)-2-methoxy-benzene, 1-(2',
  • 6-methoxy-2,3-hydroxy-naphthoic acid for example, 6-methoxy-2,3-hydroxy-naphthoic acetoacetyl-amino compounds, for example, 4,4-bisacetoacetylamino-3.3'-dimethyl-diphenyl; or
  • chloroanilines chlorotoluidines, anisidines, chloroanisidines, trifluoromethyl-anilines, nitroanilines, ni trotoluidines, nitroanisidines, aminophenyl-sulfonic acid amides, aminophenyl-carboxylic acid amides, aminodiphenyl ethers, aminoazobenzenes, N- substituted phenylene diamines, diamino-diphenyls or amino-anthraquinones.
  • Suitable alkalis used for the dissolution of the coupling component are aqueous sodium hydroxide solution, aqueous potassium hydroxide solution or strong organic bases, for example, ethyl-diethanol-amine.
  • aqueous sodium hydroxide solution aqueous potassium hydroxide solution or strong organic bases, for example, ethyl-diethanol-amine.
  • protective colloides in the alkaline impregnation bath there may be used albumen condensation products, sulfonated castor oils, condensation products of naphthalene sulfonic acids with formaldehyde or condensation products from oleic acid with N-methyl-taurine.
  • diazonium compounds As acidic agents in the aqueous solutions of diazonium compounds or as acidic additive to organic solvents to set free the diazonium compounds capable of coupling from the diazoamino compounds or antidiazotates which can be used in accordance with the invention, there are mentioned volatile, organic acids, for example, acetic acid, formic acid or propionic acid.
  • organic solvents there may be used in the present invention, in pure form, in mixture with one another, or in emulsion by the addition of up to 6% of water:
  • halogenated hydrocarbons for example, trichloroethylene, perchloroethylene, tetrachloroethane, methylene chloride, or trifluorotrichloroethane; aromatic hydrocarbons, for example, benzene or xylene; and aliphatic or cycloaliphatic hydrocarbons, for example, Tetralin.
  • Composition of Solution A Fifteen g of l-(2.3-hydroxy-naphthoyl-amino)-2- methoxybenzene were dissolved by boiling in a mixture of 15 cc. of sodium hydroxide solution (of 32.5%) and l l of soft water. and 3 g of a condensation product form naphthalene sulfonic acid and formaldehyde were added to this solution.
  • N Composition of Solution B 13.5 g of the sulfate of 1-amino-2,5-dichlorobenzene were diazotized by pouring over 27 cc. of hydrochloric acid (of 32%), 27 cc of water and ice as well as an aqueous solution of 10 g of sodium nitrite, the clear diazo solution was then introduced in a bath of l l of cold water which contained 2 g of a condensation product from 1 mol of octadecyl alcohol with 10 mols of ethylene oxide, 34 g of crystallized sodium acetate and 15 cc. of acetic acid (of The following Table 1 shows further combinations of coupling components and diazo components by means of which also intense dyeings of good fastness properties may be manufactured according to the process of this inveniton.
  • EXAMPLE 1 A cottom fabric was continuously passed through the Solution A heated to 60-90C and having the composition indicated hereinafter, and was squeezed between rolls to yield a liquor absorption of 80%, calculated on l-amino-3-chlorobenzene l-amino-2-methoxy-4-nitrobenzene l-amino-2-methyl-3-chlorobenzene l-amind-2-methyl-5-chlorobenzene l-amino-2-methoxy-4-nitrobenzene 4-amino-2',3-dimethyll l '-azobenzene 4-amino-4'-methoxydiphenyl amine l-arnin0-2,4-dimethoxy-4-benzoyl-aminobenzene 4,4'-diamino-3,3-dimethoxy-diphenyl the weight of the dry material.
  • THe padded fabric was then dried by means of hot air at l00-l20C, passed through the cold Solution B having the composition hereinafter described and was again squeezed between rolls to yield a liquor absorption of 80%. Subsequently, the padding was exposed to the action of air at room temperature for 30-60 seconds and then passed through two to five perchloroethylene baths at a tem'peraclaret brown yellow red black garnet blue blue blue dium cyanamide, dissolved by pouring over hot water of 70C.
  • the material was squeezed between rolls to yield a liquid absorption of 80%, calculated on the weight of the dry material, dried and passed through a bath of trichloroethylene heated to 80C which contained 3 cc./l of acetic acid (of 100%). Thematerial should be exposed to the efiect of the acetic solvent bath for at least seconds. In two to five subsequent baths of trichloroethylene heated to 60 to 80C the dyeing obtained was rinsed and finished. An intense red dyeing was obtained. Finally, the dyed fabric was dried and the solvent was recovered.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US00206904A 1970-12-12 1971-12-10 Process for the manufacture of insoluble azo dyestuffs on cellulose fibers Expired - Lifetime US3787179A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19702061357 DE2061357A1 (de) 1970-12-12 1970-12-12 Verfahren zur Erzeugung von unlöslichen Azofarbstoffen auf Cellulosefasern

Publications (1)

Publication Number Publication Date
US3787179A true US3787179A (en) 1974-01-22

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US00206904A Expired - Lifetime US3787179A (en) 1970-12-12 1971-12-10 Process for the manufacture of insoluble azo dyestuffs on cellulose fibers

Country Status (6)

Country Link
US (1) US3787179A (enrdf_load_stackoverflow)
BE (1) BE776540A (enrdf_load_stackoverflow)
CH (2) CH1787971A4 (enrdf_load_stackoverflow)
DE (1) DE2061357A1 (enrdf_load_stackoverflow)
FR (1) FR2118054A1 (enrdf_load_stackoverflow)
GB (1) GB1377210A (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4057389A (en) * 1975-12-20 1977-11-08 Hoechst Aktiengesellschaft Process for the printing with developing dyes
US4094637A (en) * 1974-10-19 1978-06-13 Hoechst Aktiengesellschaft Process for the printing with developing dyes
US4212648A (en) * 1977-09-09 1980-07-15 Hoechst Aktiengesellschaft Process for the printing of cellulose fiber fabrics
US4212646A (en) * 1977-09-09 1980-07-15 Hoechst Aktiengesellschaft Process for the printing of mixed fabrics of polyester and cellulose fibers

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2847532C3 (de) * 1978-11-02 1981-08-06 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von Azofarbstoffen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2173178A (en) * 1936-08-05 1939-09-19 Celanese Corp Dyeing of textile and other materials
US2274751A (en) * 1942-03-03 Materials
US2828180A (en) * 1952-05-31 1958-03-25 Anonima Italiana Colori E Affi Water-in-oil dyestuff emulsions and their application to the dyeing and printing of cloths and fibers

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2274751A (en) * 1942-03-03 Materials
US2173178A (en) * 1936-08-05 1939-09-19 Celanese Corp Dyeing of textile and other materials
US2828180A (en) * 1952-05-31 1958-03-25 Anonima Italiana Colori E Affi Water-in-oil dyestuff emulsions and their application to the dyeing and printing of cloths and fibers

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4094637A (en) * 1974-10-19 1978-06-13 Hoechst Aktiengesellschaft Process for the printing with developing dyes
US4057389A (en) * 1975-12-20 1977-11-08 Hoechst Aktiengesellschaft Process for the printing with developing dyes
US4212648A (en) * 1977-09-09 1980-07-15 Hoechst Aktiengesellschaft Process for the printing of cellulose fiber fabrics
US4212646A (en) * 1977-09-09 1980-07-15 Hoechst Aktiengesellschaft Process for the printing of mixed fabrics of polyester and cellulose fibers

Also Published As

Publication number Publication date
CH554971A (enrdf_load_stackoverflow) 1974-10-15
GB1377210A (en) 1974-12-11
FR2118054A1 (enrdf_load_stackoverflow) 1972-07-28
CH1787971A4 (enrdf_load_stackoverflow) 1974-04-30
BE776540A (fr) 1972-06-12
DE2061357A1 (de) 1972-06-15

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