GB1581268A - Fibre-reactive chlorotriazine disazo dyes - Google Patents

Fibre-reactive chlorotriazine disazo dyes Download PDF

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Publication number
GB1581268A
GB1581268A GB3272177A GB3272177A GB1581268A GB 1581268 A GB1581268 A GB 1581268A GB 3272177 A GB3272177 A GB 3272177A GB 3272177 A GB3272177 A GB 3272177A GB 1581268 A GB1581268 A GB 1581268A
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United Kingdom
Prior art keywords
sulfonic acid
aminonaphthalene
amino
compound
formula
Prior art date
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Expired
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GB3272177A
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BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of GB1581268A publication Critical patent/GB1581268A/en
Expired legal-status Critical Current

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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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/08—Azo dyes
    • C09B62/09—Disazo or polyazo dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Description

(54) FIBER-REACTIVE CHLOROTRIAZINE DISAZO DYES (71) We, BASF AKTIENGESELLSCHAFT, a German Joint Stock Company of 6700 Ludwigshafen, Federal Republic of Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- The present invention provides novel reactive dyes which in the form of the free acids correspond to the formula I
where m is 0, 1 or 2, n is 0, 1 or 2, m+n is 1 or 2, R' is hydrogen, methyl, ethyl, chlorine or bromine, R2 is hydrogen or methyl and R3 is hydrogen, methyl, ethyl, chlorine or bromine.
The compounds of the formula I are useful for dyeing textile material of cellulosic fibers by the conventional processes for reactive dyes. In particular, they may be used in the cold batch process, the exhaust process and in continuous processes. Yellowish brown to brown dyeings having good lightfastness and wet fastness properties, e.g. fastness to water, washing and peroxide, are obtained.
The compounds of the formula I can be manufactured by condensing a compound of the formula II
R1, R2, R3 m and n having the above meanings, with phenyldichlorotriazine.
Compounds of the formula II may be obtained by reacting a diazo compound of an amine of the formula
R1, R2, R3, m and n having the above meanings, with a compound of the formula
The reactions are known in principle and take place in a similar way under comparable conditions.
Compounds of the formula Ia
in which R2 has the above meaning, are of particular importance.
In the Examples which follow, parts and percentages are by weight, unless stated otherwise.
EXAMPLE 1 25 parts of finely pulverized phenyldichlorotriazine and 1 part of a commercial wetting agent are added to a solution of 61.9 parts of the disazo dye from 4 amino - 2,5 - dimethyl - azobenzene - 2',5' - disulfonic acidel aminonaphthalene - 6 - sulfonic acid in 400 parts of H2O at 650C. During the reaction, the pH is kept at from 6.5 to 7.5 by adding 53 parts of 10 percent strength sodium carbonate solution. The condensation is complete after about 6 hours. The dye is then precipitated by adding sodium chloride, filtered off and dried. It dyes cotton in fast yellowish brown hues.
EXAMPLES 2-6 The Table which follows shows further components for the manufacture of azo dyes, from which the corresponding dyes of the invention are obtained by condensing with phenyldichlorotriazine; all these dyes give yellowish brown dyeings on cotton.
Example Diazo Component Coupling Component 2 4-amino-azobenzene-2,4'- I-aminonaphthalene disulfonic acid 7-sulfonic acid 3 4-amino-azobenzene-4'- I-aminonaphthalene sulfonic acid 7-sulfonic acid 4 4-amino-3-methyl-azobenzene- I-aminonaphthalene- 2',5'-disulfonic acid 6-sulfonic acid 5 4-amino-6,4'-dimethyl-azo- I-aminonaphthalene- benzene-2'-sulfonic acid 6-sulfonic acid 6 4-amino-2'-chloro-azobenzene- I-aminonaphthalene- 2,4'-disulfonic acid 6-sulfonic acid WHAT WE CLAIM IS: 1. Reactive dyes which in the form of the free acid correspond to the formula I
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (7)

  1. **WARNING** start of CLMS field may overlap end of DESC **.
    R1, R2, R3, m and n having the above meanings, with a compound of the formula
    The reactions are known in principle and take place in a similar way under comparable conditions.
    Compounds of the formula Ia
    in which R2 has the above meaning, are of particular importance.
    In the Examples which follow, parts and percentages are by weight, unless stated otherwise.
    EXAMPLE 1
    25 parts of finely pulverized phenyldichlorotriazine and 1 part of a commercial wetting agent are added to a solution of 61.9 parts of the disazo dye from 4 amino - 2,5 - dimethyl - azobenzene - 2',5' - disulfonic acidel aminonaphthalene - 6 - sulfonic acid in 400 parts of H2O at 650C. During the reaction, the pH is kept at from 6.5 to 7.5 by adding 53 parts of 10 percent strength sodium carbonate solution. The condensation is complete after about 6 hours. The dye is then precipitated by adding sodium chloride, filtered off and dried. It dyes cotton in fast yellowish brown hues.
    EXAMPLES 2-6 The Table which follows shows further components for the manufacture of azo dyes, from which the corresponding dyes of the invention are obtained by condensing with phenyldichlorotriazine; all these dyes give yellowish brown dyeings on cotton.
    Example Diazo Component Coupling Component
    2 4-amino-azobenzene-2,4'- I-aminonaphthalene disulfonic acid 7-sulfonic acid
    3 4-amino-azobenzene-4'- I-aminonaphthalene sulfonic acid 7-sulfonic acid
    4 4-amino-3-methyl-azobenzene- I-aminonaphthalene- 2',5'-disulfonic acid 6-sulfonic acid
    5 4-amino-6,4'-dimethyl-azo- I-aminonaphthalene- benzene-2'-sulfonic acid 6-sulfonic acid
    6 4-amino-2'-chloro-azobenzene- I-aminonaphthalene- 2,4'-disulfonic acid 6-sulfonic acid WHAT WE CLAIM IS: 1. Reactive dyes which in the form of the free acid correspond to the formula I
    where m is 0, 1 or 2, n is 0, 1 or 2, m+n is 1 or 2, R1 is hydrogen, methyl, ethyl, chlorine or bromine, R2 is hydrogen or methyl and R3 is hydrogen, methyl, ethyl, chlorine or bromine.
  2. 2. Compounds as claimed in Claim 1, of the formula Ia
    where R2 has the meaning given in Claim 1.
  3. 3. A compound as claimed in Claim 1 and as hereinbefore individually identified.
  4. 4. A process for the manufacture of a compound as claimed in Claim 1, in which a compound of the formula II
    where R1, R2, R3, m and n have the meanings given in Claim 1, is condensed with phenyldichlorotriazine.
  5. 5. A process as claimed in Claim 4 carried out substantially as described in any one of the foregoing specific Examples.
  6. 6. A compound as claimed in Claim 1 whenever obtained by a process as claimed in Claim 4 or Claim 5.
  7. 7. Cellulosic fibers dyed or printed with a compound as claimed in any one of Claims 1 to 3 or in Claim 6.
GB3272177A 1976-08-05 1977-08-04 Fibre-reactive chlorotriazine disazo dyes Expired GB1581268A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19762635158 DE2635158C3 (en) 1976-08-05 1976-08-05 Disazo reactive dyes, process for their production and their use for dyeing and printing cellulosic fibers

Publications (1)

Publication Number Publication Date
GB1581268A true GB1581268A (en) 1980-12-10

Family

ID=5984753

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3272177A Expired GB1581268A (en) 1976-08-05 1977-08-04 Fibre-reactive chlorotriazine disazo dyes

Country Status (5)

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JP (1) JPS5318631A (en)
DE (1) DE2635158C3 (en)
FR (1) FR2360641A1 (en)
GB (1) GB1581268A (en)
IT (1) IT1086296B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1983000495A1 (en) * 1981-08-07 1983-02-17 Matsuo, Tadashi Reactive disazo compounds and method for dyeing cellulose fibers using same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2917059A1 (en) * 1979-04-27 1980-11-06 Basf Ag METHOD FOR COLORING TEXTILE MATERIAL CONTAINING HYDROXYL GROUPS AND NEW DYES
CN105273437B (en) * 2015-10-20 2017-05-17 湖北华丽染料工业有限公司 Red reactive dye as well as preparation method and application thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1483235A (en) * 1965-07-14 1967-06-02 Ciba Geigy New disazo dyes and process for their preparation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1983000495A1 (en) * 1981-08-07 1983-02-17 Matsuo, Tadashi Reactive disazo compounds and method for dyeing cellulose fibers using same

Also Published As

Publication number Publication date
DE2635158C3 (en) 1980-03-27
JPS5318631A (en) 1978-02-21
DE2635158A1 (en) 1978-02-09
FR2360641B1 (en) 1980-01-04
FR2360641A1 (en) 1978-03-03
IT1086296B (en) 1985-05-28
DE2635158B2 (en) 1979-07-26

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