US3287349A - 2-hydroxy-3-carboxyamido-benzene-azo-2-hydroxy-5, 6, 7, 8-tetrahydronaphthalene dyestuffs - Google Patents

2-hydroxy-3-carboxyamido-benzene-azo-2-hydroxy-5, 6, 7, 8-tetrahydronaphthalene dyestuffs Download PDF

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Publication number
US3287349A
US3287349A US193323A US19332362A US3287349A US 3287349 A US3287349 A US 3287349A US 193323 A US193323 A US 193323A US 19332362 A US19332362 A US 19332362A US 3287349 A US3287349 A US 3287349A
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Prior art keywords
hydroxy
benzene
dye
dyes
parts
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Expired - Lifetime
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US193323A
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English (en)
Inventor
Gaetani Ermanno
Moiso Ugo
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Aziende Colori Nazionali Affini ACNA SpA
ACNA Chimica Organica SpA
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ACNA Chimica Organica SpA
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Classifications

    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/16—Monoazo compounds containing chromium

Definitions

  • the present invention relates to monoazo dyes which develop brown shades upon subsequent chromation, more particularly by the dyeing and chromation of wool and polyamide fibers in a single neutral or slightly acid bath according to the metachrome process.
  • X is selected from halogen atoms, and N0 groups
  • Y is selected from acylamino groups, halogen-containing acylamino groups and alkoxycarboxyamino groups.
  • Metachrome brown shades have generally been heretofore obtained by the metallization on fibers, of monoazodyes which are the product obtained by coupling the diazo compounds of suitable orthoaminophenols with para-alkyl phenol derivatives, (e.g., para-cresol, paratertiary butylphenol, p-tert.amyl phenol, etc., and preferably tlso with other substitutions, such as, e.g., l-hydroxy- 2-acetamino-4-methyl benzene, 1-hydroxy-2-propionyl amino-4-tertiary-butyl benzene, 1-hydroxy-2-acetamino-4- tert.amyl benzene, etc).
  • para-alkyl phenol derivatives e.g., para-cresol, paratertiary butylphenol, p-tert.amyl phenol, etc.
  • tlso with other substitutions such as, e.g., l-hydroxy
  • An object of the present invention is herefore to provide monoazo dyes, for wool and polyamidic fibers, which are metallizable on the fibers during or after dyeing and have the general formula:
  • Another object of the present invention is to provide textile materials such as fibers, yarns and the like, which are dyed with the instant dyes.
  • the new dyes, obtained according to the present invention are excellent for W001 and polyamidic fibers and are suitable for a dyeing step followed by a chromation treatment.
  • the dyeing and chromation can be carried out in a single bath, which is either neutral or slightly acid, according to the so called metachrome process.
  • the dyes of the present invention possess further advantages. Thus, they possess good fastness to light even under wet conditions and also good fastness to potting treatments, even in comparison with dyes derived from alkylphenols having a higher molecular weight (e.g., p.tert.butyl, p-tertiary amyl) -and even in comparison with dyes possessing further substituents such as l-hydroxy 2 acetamino-4-methylbenzene and 1-hydroxy-2- acetamino-4-tert.butylbenezene.
  • This improved fastness of the present dyes is probably due to the cyclic structure of the alkyl substitution.
  • the dyeing step may be carried out using any suitable conventional procedure.
  • the present invention is described with reference to some of its preferred embodiments. There are, however, obviously many modifications and variations of the instant invention which will be evident to persons skilled in the art.
  • various phenols may be employed as the o-aminophenol, which is coupled with Z-hydroxy-S,6,7,S-tetTahydrQnap-hthalene in order to obtain a dye to be .metallized with a brown shade. It is to be understood that these and other suitable modifications and variations are within the spirit and scope of the present invention.
  • the suspension of diazo-cornpound is neutralized with odiurn carbonate and is introduced at C. into a soluion of 14.9 parts of 2-hydroXy-5,6,7,8-tetrahydronaphhalene in 100 parts of Water containing 4 parts of sodium iydroxide and 17 parts of sodium carbonate.
  • the precipitated dye is sepaated by filtration and is suspended in water slightly alk-' llinized with sodium carbonate. It is then filtered and lried.
  • the monoazodye thus obtained has the following fornula:
  • the dye is a black-brown powder, which is very suit- ;ble for dyeing wool by the known metachrorne process, hus giving a dark-brown shade with very good wet and ight fastness.
  • the dyeing can also be carried out by employing suc- :essive chromation.
  • Example 2 22.5 parts of 1-hydroxy-2-amino-4-nitro-6-propionyltIIliIlO benzene are diazotized by following the procedure )f Example 1.
  • the suspension of d-iazocompound is neuralized with Na CO and is introduced at 0 C. into a olution of 14.9 parts of Z-hydroxy-S,6,7,'8-tetrahydroiaphtha'lene in 40 parts of water, 4 parts of NaOH and 50 parts by volume of pyridine.
  • the coupling occurs very quickly.
  • the dye product )btained after coupling contains about 30% by volume of Jyri-dine.
  • the dye which is isolated and dried, is a brown powder raving the following formula:
  • Example 3 20 parts of 1hydroxy-Z-amino-4-chloro-6-acetaminoaenzene are diazotized and coupled as in Example 1.
  • This dye is also suitable for dyeing followed by successive chromation.
  • Examples 4-7 These examples are conducted by following the procedure of Example 1. In each case, 2-hydroxy-5,6,7,8-tetraihydnonap'hthalene is used as the coupling component. The various other dye components employed and the results obtained are reported in Table I, shown below.
  • 6-propionylamin0benzene better tastness to fulling.
  • a monoazo dye having the formula (j... p X a wherein X is selected from the group consisting of chlorine, and a N0 group, and Y is selected from the group consisting of a caoboxylamino radical containing from 1 to 4 carbon atoms, a canbo-xylarnino radical containing from 1 to 4 carbon atoms and further containing chlorine in the hydnocanbon chain, and an alkoxy-carboxylamino radical containing from 1 to 4 carbon atoms.
  • Y is a carboxylamino radical containing from 1 to 4 canbon atoms.
  • Y is a canboxylamino radical containing from 1 to 4 carbon atoms and further containing chlorine in the hydrocanbon chain.
  • Y is an :alkoxy-oarboxylamino radical containing from 1 to 4 carbon atoms.
  • the monoazo dye which has the formula:
  • the monoazo dye which has the formula:
  • the monoazo dye which has the formula:
  • the monoazo dye which has the formula:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
US193323A 1961-05-12 1962-05-08 2-hydroxy-3-carboxyamido-benzene-azo-2-hydroxy-5, 6, 7, 8-tetrahydronaphthalene dyestuffs Expired - Lifetime US3287349A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT882261 1961-05-12

Publications (1)

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US3287349A true US3287349A (en) 1966-11-22

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Country Status (6)

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US (1) US3287349A (de)
BE (1) BE617544A (de)
CH (1) CH417805A (de)
DE (1) DE1444561A1 (de)
ES (1) ES277263A1 (de)
GB (1) GB964673A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3410841A (en) * 1965-10-28 1968-11-12 Gaf Corp 5, 6, 7, 8-tetra-hydro-2-naphtholazobenzanilide dyestuffs

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE626430C (de) * 1933-12-14 1936-02-26 I G Farbenindustrie Akt Ges Verfahren zur Herstellung von metallhaltigen Azofarbstoffen
US2634263A (en) * 1949-07-21 1953-04-07 Sandoz Ag Monoazo dyestuffs
US2766230A (en) * 1951-08-07 1956-10-09 Ciba Ltd Cobaltiferous azo-dyestuffs
DE1007903B (de) * 1955-12-03 1957-05-09 Bayer Ag Verfahren zur Herstellung von Monoazofarbstoffen bzw. deren Metallkomplexverbindungen
DE1076854B (de) * 1955-06-28 1960-03-03 Gen Aniline & Film Corp Verfahren zur Herstellung von Azofarbstoffen

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE626430C (de) * 1933-12-14 1936-02-26 I G Farbenindustrie Akt Ges Verfahren zur Herstellung von metallhaltigen Azofarbstoffen
US2634263A (en) * 1949-07-21 1953-04-07 Sandoz Ag Monoazo dyestuffs
US2766230A (en) * 1951-08-07 1956-10-09 Ciba Ltd Cobaltiferous azo-dyestuffs
DE1076854B (de) * 1955-06-28 1960-03-03 Gen Aniline & Film Corp Verfahren zur Herstellung von Azofarbstoffen
DE1007903B (de) * 1955-12-03 1957-05-09 Bayer Ag Verfahren zur Herstellung von Monoazofarbstoffen bzw. deren Metallkomplexverbindungen

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3410841A (en) * 1965-10-28 1968-11-12 Gaf Corp 5, 6, 7, 8-tetra-hydro-2-naphtholazobenzanilide dyestuffs

Also Published As

Publication number Publication date
CH417805A (de) 1966-07-31
ES277263A1 (es) 1962-10-16
DE1444561A1 (de) 1968-11-21
GB964673A (en) 1964-07-22
BE617544A (fr) 1962-08-31

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