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 PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- benzene
- dye
- dyes
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT882261 | 1961-05-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3287349A true US3287349A (en) | 1966-11-22 |
Family
ID=11127311
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US193323A Expired - Lifetime US3287349A (en) | 1961-05-12 | 1962-05-08 | 2-hydroxy-3-carboxyamido-benzene-azo-2-hydroxy-5, 6, 7, 8-tetrahydronaphthalene dyestuffs |
Country Status (6)
Country | Link |
---|---|
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)
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)
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 |
-
1962
- 1962-05-08 US US193323A patent/US3287349A/en not_active Expired - Lifetime
- 1962-05-09 CH CH556762A patent/CH417805A/de unknown
- 1962-05-11 GB GB18253/62A patent/GB964673A/en not_active Expired
- 1962-05-11 DE DE19621444561 patent/DE1444561A1/de active Pending
- 1962-05-11 BE BE617544A patent/BE617544A/fr unknown
- 1962-05-11 ES ES277263A patent/ES277263A1/es not_active Expired
Patent Citations (5)
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)
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 |
GB964673A (en) | 1964-07-22 |
DE1444561A1 (de) | 1968-11-21 |
BE617544A (fr) | 1962-08-31 |
ES277263A1 (es) | 1962-10-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2004250A (en) | Azo-dyestuffs, and process of making same | |
US3287349A (en) | 2-hydroxy-3-carboxyamido-benzene-azo-2-hydroxy-5, 6, 7, 8-tetrahydronaphthalene dyestuffs | |
US2314023A (en) | Substantive azo dyestuffs and process of making same | |
US2204230A (en) | Azo dyes | |
US2638403A (en) | Dyeing of nylon with sulfonamide azo dyes | |
US2135964A (en) | Azo dyestuffs and fiber dyed therewith | |
US1921337A (en) | Copper-containing azodyestuff | |
US3527746A (en) | Monoazo heterocyclic containing triazine dyestuffs | |
US3086977A (en) | Basic anthraquinone dyestuffs | |
US1835393A (en) | New monoazodyestuffs | |
US2564243A (en) | Azo dyestuffs | |
US1851121A (en) | Substantive azo dyestuffs | |
US2243617A (en) | Azo dyestuffs and process of making same | |
US2554443A (en) | Azo safranine leather dyestuffs | |
US2228416A (en) | Azo dyes | |
US3324106A (en) | 1-phenyl-5-pyrazolone-3-carbonamide disazo dyestuffs | |
US3362781A (en) | 7-(2', 5'-dichlorophenylazo)-6-methyl-8-hydroxy-quinoline dyeing of metallized polyolefin fibers | |
US2209749A (en) | Water-insoluble azo dyestuffs | |
US2346922A (en) | Metallizable azo dye | |
US2044891A (en) | Substantive azodyestuffs and process of making same | |
US1887289A (en) | Manufacture of strongly basic azodyestuffs | |
US2030991A (en) | Azo dyes and methods for their preparation | |
US3577405A (en) | Water-soluble,yellow mono-azo dyes with active methylene coupler | |
US2041829A (en) | Azo-dyestuffs | |
US1854846A (en) | Monoazo-dyestuffs and their manufacture |