GB595181A - Manufacture of new azo-dyestuffs - Google Patents

Manufacture of new azo-dyestuffs

Info

Publication number
GB595181A
GB595181A GB15996/43A GB1599643A GB595181A GB 595181 A GB595181 A GB 595181A GB 15996/43 A GB15996/43 A GB 15996/43A GB 1599643 A GB1599643 A GB 1599643A GB 595181 A GB595181 A GB 595181A
Authority
GB
United Kingdom
Prior art keywords
amino
acid
mols
aminoazo
mol
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
Application number
GB15996/43A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Gesellschaft fuer Chemische Industrie in Basel CIBA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Publication of GB595181A publication Critical patent/GB595181A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/12Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

Azo-stilbene dyestuffs, of the general formula <FORM:0595181/IV/1> wherein three of the symbols x represent residues of aminoazo dyestuffs of the general formula NH2-y-R1-N = N-R2, wherein R1 and R2 represent aromatic nuclei of the benzene series, the NH2-ygroup and the -N = N- linkage being in p-relationship and R2 containing a hydroxy group in o-position to a carboxyl group, and y represents a direct linkage between NH2 and R1 or a grouping of the formula <FORM:0595181/IV/2> (one Z representing the linkage connecting this grouping to the NH2 group, and the other representing hydrogen, whilst the NH- group is attached to R1), and the fourth x represents the residue of any desired aminoazo dyestuff, are manufactured by condensing (1) 2 mols. of a 1 : 3 : 5 - trihalogen - triazine (e.g. cyanine bromide or, preferably, chloride) with 1 mol. of 4 : 41 - diaminostilbene - 2 : 21 - disulphonic acid, and the product with 3 mols. of the same or different aminoazo dyestuffs of the general formula above and 1 mol. of any aminoazo dyestuff, or (2) 1 mol. of a 1 : 3 : 5-trihalogen-triazine with 2 mols. of the same or different aminoazo dyestuffs of the general formula above, a further mol. of a 1 : 3 : 5-trihalogen-triazine with 1 mol. of an aminoazo dyesteuff of the general formula above and 1 mol. of any aminoazo dyestuff, and the products with 1 mol. of 4 : 41-diaminostilbene-2 : 21-disulphonic acid, or (3) 2 mols. of a 1 : 3 : 5-trihalogen-triazine with 2 mols. of the same or different aminoazo dyestuffs of the general formula above and then with 1 mol. of 4 : 41-diaminostilbene-2 : 21-disulphonic acid, and the product with 1 mol. of an aminoazo dyestuff of the general formula above and 1 mol. of any aminoazo dyestuff, or (4) 2 mols. of a 1 : 3 : 5-trihalogen-triazine with 1 mol. of an aminoazo dyestuff of the general formula above and 1 mol. of any aminoazo dyestuff and then with 1 mol. of 4 : 41-diaminostilbene-2 : 21-disulphonic acid, and the product with 2 mols. of the same or different aminoazo-dyestuffs of the general formula above. The products yield mainly yellow dyeings, which may be after-treated with agents yielding metal, especially copper, or also, for example, chromium, cobalt or nickel, particularly on natural or regenerated cellulose fibres, e.g. cotton, ramie, flax or viscose or cuprammonium artificial silk, which may be matted if desired, or mixtures of these materials with animal fibres such as wool or silk, e.g. a mixture of wool and viscose staple fibre, the dyeing of these mixed materials being advantageously conducted in a neutral bath in the presence of sodium or potassium chromate, or, if desired, in conjunction with acid or mordant wool dyestuffs. In examples: (1) 2 mols. of cyanuric chloride are condensed with 1 mol. of the disodium salt of 4 : 41-diaminostilbene-2 : 21 disulphonic acid and the product is condensed with 4 mols. of the sodium salt of 41-amino-1 : 11-azobenzene-4-hydroxy-3-carboxylic acid; (2) cotton is dyed with the product of (1) from a bath containing sodium carbonate and sodium sulphate, and is after-treated with a solution of copper sulphate and tartaric acid neutralized with caustic soda, yielding a greenish yellow shade. A table gives the properties of further dyestuffs containing as the residues represented by x in the general formula: (a) 4 residues of 4-amino-41-hydroxy-51-methyl-1 : 11 - azobenzene - 31 - carboxylic acid; (b) 4 residues of 4 - amino - 3 - methyl - 6 - methoxy - 41 - hydroxy - 1 : 11-azobenzene-31-carboxylic acid; (c) 3 residues of 4-amino-41-hydroxy-1 : 11-azobenzene-31-carboxylic acid and one of 4-(411-amino) -benzoylamino-2-methyl-5-methoxy-41-hydroxy - 1 : 11 - azobenzene - 31 - carboxylic - 5 - sulphonic acid; (d) 2 residues each of the aminoazo dyestuffs of (c); (e) 3 residues of 4 - amino - 41 - hydroxy - 1 : 11 - azobenzene - 31 - carboxylic acid and one of (5-aminobenzoic acid)-(2-azo-41)-(31-methyl-51-pyrazolone); (f) 3 residues of 4-amino-41-hydroxy-1 : 11-azobenzene-31-carboxylic acid and one of (5-aminobenzoic acid)-(2-azo-11)-(21-hydroxy-31-naphthoic acid); (h) 3 residues of 4-amino-41-hydroxy - 1 : 11-azobenzene-31-carboxylic acid and one of 4-amino-1 : 11-azobenzene-41-sulphonic acid. Additional aminoazo dyestuffs NH2-y-R1-N = N-R2 specified are: 41-amino - 21- and -31 - methyl-, 41 - amino - 51 - methoxy-21-methyl- and 41-amino-21- and -31-methoxy - 1 : 11 - azobenzene - 4 - hydroxy - 3 - carboxylic acid, 41-amino-21-methoxy-1 : 11-azobenzene - 4 - hydroxy - 3 - carboxylic - 5 - sulphonic acid, 41 - (311- and 411 - amino) - benzoylamino-, 41 - (411 - amino) - benzoylamino - 21 - methyl - 51 - methoxy-, 41 - (411 - amino) - benzoylamino - 31 - methoxy-, 41 - (411 - amino) - benzoylamino - 21 - methyl- and 41 - (311 - amino) - benzoylamino - 21 : 51-dimethyl-1 : 11-azobenzene-4-hydroxy-5-carboxylic acid, 41 - (311- and 411 - amino) - benzoylamino-, 41-(411-amino) - benzoylamino - 31-methoxy-, 41-(311-amino)-benzoylamino-31-methyl- and 41-(311-amino) -benzoylamino-21-acetylamino-51-methoxy - 1 : 11-azobenzene-4-hydroxy - 3 - sulpho - 5 - carboxylic acid, and 41 - (411 - amino) - benzoylamino - 21 - methyl - 51 - methoxy - 1 : 11 - azobenzene - 2 - hydroxy - 3 - carboxy-5-sulphonic acid. The aminoazo dyestuffs corresponding to the fourth residue x may be additionally the various aminoazobenzene- and aminoazotoluene-sulphonic acids, also products containing naphthalene nuclei, heterocyclic nuclei or aliphatic residues, e.g. 1-amino-4-hydroxybenzene - 3 - carboxylic acid --> a -naphthylamine, 2 - aminonaphthalene - 4 : 8 - disulphonic acid --> m-toluidine, or the reduced reaction product of diazotized 1-amino-4-nitrobenzene-2-carboxylic acid with the anilide or o-anisidide of 2 : 3-hydroxynaphthoic acid or with a compound containing a reactive methylene group, such as 1-phenyl-3-methyl-5-pyrazolone, barbituric acid or the anilide or o-anisidide of acetoacetoacetic acid. Samples have been furnished under Sect. 2 (5) of dyestuffs prepared as follows: (I) 2 mols. of cyanuric chloride are condensed with 2 mols. of the disodium salt of 4-amino-41-hydroxy-1 : 11-azobenzene - 31 - carboxylic acid - 51 - sulphonic acid, then with a further 2 mols. of the same compound, and the product is condensed with 1 mol. of the disodium salt of 4 : 41-diaminostilbene-2 : 21-disulphonic acid; (II) 2 mols. of cyanuric chloride are condensed with 2 mols. of the aminoazo compound of I, then with 1 mol. of the stilbene compound, and the product is condensed with a further 2 mols. of the aminoazo compound; (III) 1 mol. of the disodium salt of 4 : 41-diaminostilbene-2 : 21-disulphonic acid is condensed with 2 mols. of cyanuric chloride and the product is condensed with 2 mols. of the aminoazo compound of (I) and then with a further 2 mols. of the same compound. The Specification as open to inspection under Sect. 91 comprises also an alternative process in which there is used, instead of at least one of the aminoazo dyestuffs corresponding to the residues x in the general formula of the products, a suitable diazo component, and the product is diazotized and coupled with the appropriate coupling component; e.g. the amine may be of the general formula NH2-y-R1-v (wherein v represents an amino group, or a group converted thereto after the condensation, in p-position to the NH2-ygroup) and the coupling component an o-hydroxycarboxylic acid of the benzene series. This subject-matter does not appear in the Specification as accepted.
GB15996/43A 1942-09-29 1943-09-29 Manufacture of new azo-dyestuffs Expired GB595181A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH595181X 1942-09-29

Publications (1)

Publication Number Publication Date
GB595181A true GB595181A (en) 1947-11-28

Family

ID=4522387

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15996/43A Expired GB595181A (en) 1942-09-29 1943-09-29 Manufacture of new azo-dyestuffs

Country Status (1)

Country Link
GB (1) GB595181A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008142989A1 (en) * 2007-05-11 2008-11-27 Nippon Kayaku Kabushiki Kaisha Water-soluble azo compound or salt thereof, ink composition, and colored material
US7740696B2 (en) 2005-10-25 2010-06-22 Nippon Kayaku Kabushiki Kaisha Water-soluble azo compound, ink composition, and colored article
US7771525B2 (en) 2006-11-01 2010-08-10 Nippon Kayaku Kabushiki Kaisha Water-soluble azo compound or salt thereof, ink composition and colored product
CN107325584A (en) * 2017-07-03 2017-11-07 上海安诺其集团股份有限公司 The disulfonic acid compound of 4,4 ' diaminobenzil 2,2 ', its intermediate, preparation method and application

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7740696B2 (en) 2005-10-25 2010-06-22 Nippon Kayaku Kabushiki Kaisha Water-soluble azo compound, ink composition, and colored article
US7771525B2 (en) 2006-11-01 2010-08-10 Nippon Kayaku Kabushiki Kaisha Water-soluble azo compound or salt thereof, ink composition and colored product
WO2008142989A1 (en) * 2007-05-11 2008-11-27 Nippon Kayaku Kabushiki Kaisha Water-soluble azo compound or salt thereof, ink composition, and colored material
CN107325584A (en) * 2017-07-03 2017-11-07 上海安诺其集团股份有限公司 The disulfonic acid compound of 4,4 ' diaminobenzil 2,2 ', its intermediate, preparation method and application
CN107325584B (en) * 2017-07-03 2019-07-26 浙江名毅新能源股份有限公司 4,4 '-diaminobenzils -2,2 '-disulfonic acid compound, wherein mesosome, preparation method and application

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