GB584731A - Manufacture of new azo-dyestuffs - Google Patents

Manufacture of new azo-dyestuffs

Info

Publication number
GB584731A
GB584731A GB12822/43A GB1282243A GB584731A GB 584731 A GB584731 A GB 584731A GB 12822/43 A GB12822/43 A GB 12822/43A GB 1282243 A GB1282243 A GB 1282243A GB 584731 A GB584731 A GB 584731A
Authority
GB
United Kingdom
Prior art keywords
methyl
oxyethyl
acid
aniline
cooh
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
GB12822/43A
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 GB584731A publication Critical patent/GB584731A/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
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/06Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08Amino benzenes

Landscapes

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

Abstract

Monoazo dyestuffs are made by coupling a diazo compound of a 3:5-dinitrophenylamine, free from hydroxy groups in the benzene nucleus, with a phenylamine capable of coupling in the 4-position with respect to the amino group. When no groups imparting solubility in water are present the dyestuffs can be used for dying cellulose esters or ethers and tentiles made of superpolyamides or superpolyurethanes and for colouring lacquers, varnishes and artificial masses. When a group imparting solubility is present they may be used for dyeing animal fibres in addition to the above. The diazo compounds of the following are specified:-3:5-dinitro-aniline and 4-methyl-, 2-methyl-, and 4-methoxy- and 4-ethoxy-, 3:5-dinitro-aniline. The following coupling components are specified:-aniline, 2- and 3-methyl-, 2- and 3- methoxy-, 3-acetylamine-and 3-methyl-6-methoxy-aniline, N-dimethyl, N-diethyl-, N-methyl-N-ethyl-, N-oxyethyl-, N-methoxyethyl-N-ethyl-, N-ethoxyethyl-N-ethyl-, M-dioxyethyl-, N-oxyethyl-3-methyl-N-dioxyethyl-3-methyl-, N-ethyl-N-oxyethyl-3-methyl-, N-dioxyethyl-3-methyl-6-methoxy-, N-n-butyl-N-oxyethyl-3-methyl-, <FORM:0584731/IV/1> N-methyl-3-methyl-, N-methyl-N-b :g -dioxypropyl-, N-oxyethyl-N-chloroethyl-, N-di-(acetonyethyl)- and N-n-propyl-N-methoxyethyl-3-methyl-aniline. Other coupling components are those containing, as a group imparting solubility in water, an externally-bound sulphonic acid, sulphuric acid ester or carboxylic acid group, such as the esters with polybasic acids of N-alkylanilines containing a hydroxyl group in the alkyl residue, e.g. N-methyl-N-oxyethyl-3-methyl-aniline sulphuric acid ester and the esters with organic dicarboxylic acids or sulpho-carboxylic acids as described in Specifications 517,918, 545,283 and 565,697, specifically N - oxyethyl - N - CH2.CH2.O.OOC.CH:CH.COOH-, N-methyl-N-CH2.CH2.O.SO3H-2 : 5.-dimethoxy-, N-methyl- or -n-propyl-N-CH2.CH2.O.OC.CHCl.SO3H-, N-oxyethyl-N-CH2.CH2.O.OC.COOH-3-methyl-, N-oxyethyl-N-CH2.CH2.SO3H-, N-ethyl-N-CH2.CH2.O.OC.C6H4.COOH-3-methyl- <FORM:0584731/IV/2> N-CH2CH2.O.OC.CH : CH.COOH-3-methyl-, N-methyl-N-CH2.CH2.COOH-, and N-methyl-N-CH2.CH2.O.SO3H-aniline. Dyestuffs free from these ester groups may be esterified with sulphuric acid or a polycarboxylic or sulphocarboxylic acid or a reactive derivative thereof, e.g. by oxalic acid, maleic acid, maleic anhydride, succinic anhydride, sulphuric acid or sulphochloracetic acid. In the examples the following additional coupling components are specified:-oxalic, maleic and chlorsulphoacetic acid esters of N-methyl-N-oxyethylaniline; chlorsulphoacetic acid ester of dioxyethylaniline. The coupling components may be used in the form of their 2-methane sulphonic acids. In Example 5 cellulose acetate yarn is dyed yellow in a dispersion containing the dyestuff 3:5-dinitroaniline --> aniline, a dispersing agent such as Turkey red oil, sulphite cellulose waste liquor or sulphonation products of the residues from the manufacture of benzaldehyde, soap and water. The chlorosulphoacetic esters of N-methyl-N-oxyethylaniline and N-dioxyethylaminobenzene are obtainable by heating the respective hydroxyethyl compounds with chlorosulphoacetic acid in solvent naphtha. The Specification as open to inspection under Sect. 91 comprises the use, as diazo component, of any 3:5-dinitrophenylamine, and specifies additionally 1-amino-4-chloro-3 : 5-dinitrobenzene. This subject-matter does not appear in the Specification as accepted.
GB12822/43A 1942-08-10 1943-08-09 Manufacture of new azo-dyestuffs Expired GB584731A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH584731X 1942-08-10

Publications (1)

Publication Number Publication Date
GB584731A true GB584731A (en) 1947-01-22

Family

ID=4521736

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12822/43A Expired GB584731A (en) 1942-08-10 1943-08-09 Manufacture of new azo-dyestuffs

Country Status (1)

Country Link
GB (1) GB584731A (en)

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