GB447561A - Manufacture of azo-dyestuffs - Google Patents

Manufacture of azo-dyestuffs

Info

Publication number
GB447561A
GB447561A GB5852/35A GB585235A GB447561A GB 447561 A GB447561 A GB 447561A GB 5852/35 A GB5852/35 A GB 5852/35A GB 585235 A GB585235 A GB 585235A GB 447561 A GB447561 A GB 447561A
Authority
GB
United Kingdom
Prior art keywords
methyl
methoxy
amino
cyano
oxyethyl
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
GB5852/35A
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 GB447561A publication Critical patent/GB447561A/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

Landscapes

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

Abstract

Azo dyes are made by coupling diazotized 1-amino-2-cyano-4-nitrobenzene or 1-amino-2-cyano-4 : 6-dinitrobenzene with a component of the formula ANRR<1>, where A is a benzene or naphthalene nucleus, which may be substituted, and R and R<1> are hydrogen atoms or alkyl, aryl or aralkyl groups, the coupling conditions being so selected that the group --NRR<1> is the group that causes coupling. Such of the products as contain a hydroxy or a primary or secondary amino group may be acylated or alkylated, if desired. The coupling components include compounds of the formula above in which R or R<1> is (a) a simple alkyl group, such as methyl, ethyl, propyl or butyl, or (b) a halogenalkyl group such as a chloro-, bromoor iodo-ethyl group, or (c) a hydroxyalkyl group, such as an oxyethyl, oxypropyl, oxybutyl or dioxypropyl group, or (d) an etherified or esterified hydroxyalkyl group such as an acetoxyethyl group or an ethylsulphuric acid residue, or (e) an alkylcarboxylic acid residue or a derivative thereof, such as a propionic acid residue, a propionamide or propionic ester residue or a cyanoethyl or sulphocyanoethyl residue; when R or R<1> is an aryl or aralkyl group the aryl nucleus may be substituted. Specified coupling components are aniline, the naphthylamines, N - methoxyethylaniline, N-ethyl - N - methoxyethylaniline, 3 - methyl - N-ethyl - N - methoxyethylaniline, 2 - methoxy - 5-methyl - N - methoxyethylaniline, 2-methoxy - 5-methyl - N - ethyl - N - methoxyethylaniline, 2-methoxy-5-methyl - N - butyl - N - methoxyethylaniline, 2 - methoxy - 5 - methyl - N - di(methoxyethyl)aniline, 2 : 5 - dimethoxy - N - methoxyethylaniline, 2 : 5 - dimethoxy - N - di(methoxyethyl)aniline, N - methoxyethyl - 1 - naphthylamine, N - methoxyethyl - 2 - naphthylamine, N - ethyl - N - oxyethylaniline, N - butyl - N - oxyethylaniline, 3 - methyl - N -ethyl - N - oxyethylaniline, 3-methyl - N - butyl - N - oxyethylaniline, 2 - methoxy - 5 - methyl - N - oxyethylaniline, 2-methoxy -5-methyl-N-ethyl-N-oxyethylaniline, 2-methoxy-5-methyl-N - methoxyethyl-N -oxyethylaniline, 2-methoxy-5-methyl-N-butyl-N-oxyethylaniline, 2 - methoxy - 5 - methyl - N-di(oxyethyl)aniline, 2 : 5 - dimethoxy - N - oxyethylaniline, 2 : 5-dimethoxy-N-ethyl-N-oxyethylaniline, 2 : 5-dimethoxy-N-methoxyethyl-N-oxyethylaniline, 2 : 5-dimethoxy-N -di(oxyethyl)aniline, N-oxyethyl-1-naphthylamine, N-oxyethyl-2-naphthylamine, N-ethyl-N-acetoxyethylaniline, 2 - methoxy - 5 - methyl - N - di-(acetoxyethyl)aniline, 2-methoxy-5-methyl-N-ethyl-N-acetoxyethylaniline, 2 : 5-dimethoxy-N - ethyl - N - acetoxyethylaniline, 2 : 5-dimethoxy - N - di(acetoxyethyl)aniline, 2-methoxy-5-methyl-N-methoxyethyl-N-dioxypropylaniline, 2-methoxy - 5 - methyl - N - oxyethyl - N - dioxypropylaniline, 2 - methoxy - 5 - methyl-N-oxyethyl-N-g -ethoxy-b -oxypropylaniline, 2-methoxy-5-methyl-N-oxyethyl-N-g -methoxy - b - oxypropylaniline, 2-methoxy - 5-methyl - N - butyl - N - g - ethoxy - b - oxypropylaniline, 2-methoxy-5-methyl-N-butyl-N-g -methoxy-b -oxypropylaniline, 2 : 5-dimethoxy-N-methoxyethyl - N - dioxypropylaniline, 2 : 5-dimethoxy - N - oxyethyl - N - dioxypropylaniline, 2 : 5-dimethoxy-N-oxyethyl-N-g -ethoxy-b -oxypropylaniline, 2 : 5-dimethoxy-N-oxyethyl-N-g - methoxy - b - oxypropylaniline, 2 : 5-dimethoxy-N-butyl-N-g -ethoxy-b -oxypropylaniline, 2 : 5-dimethoxy-N-butyl-N-g -methoxyethyl - b - oxypropylaniline, N - butyl - N - g -methoxy - b - oxypropylaniline, 3 - methyl - N-butyl-N-g -methoxy - b - oxypropylaniline, N-butyl - N - g - ethoxy - b - oxypropylaniline, 3-methyl-N-butyl-N-g -ethoxy-b -oxypropylaniline, N -di(oxyethyl)-aniline, 3-methyl- N - di(oxyethyl)-aniline, 3-chloro-N-di(oxyethyl)-aniline, N-di(dioxypropyl)-aniline, 3-chloro-5-methoxy-N - di(oxyethyl)-aniline, 1-amino-5-naphthol, 1 - amino-6-naphthol, 1-amino-7-naphthol, 1-amino-8-naphthol, 2-amino-3-naphthol, 2-amino-4-naphthol, 2-amino-5-naphthol, 2-amino-6-naphthol, 2-amino-7-naphthol, 2-amino-8-naphthol, and alkylaminonaphthols such as 1 - methylamino - 5-naphthol and 1 - oxyethylamino - 5 - naphthol; sulphonic acids and sulphuric esters of these compounds may also be used. The products are red, brown, violet, blue or green dyes applicable to wool, silk, cellulose, and artificial silk, particularly of cellulose esters or ethers such as acetyl- or nitro-cellulose. Thus, dispersions of non-sulphonated dyes, prepared by grinding the dyes in water with a dispersing agent such as a sulphonated residue from the manufacture of benzaldehyde or turpentine oil, may be used for dyeing acetate artificial silk; alternatively, such dispersions may be treated with a further amount of the same or another dispersing agent, such as sulphite cellulose lye, and then dried in vacuo. In the examples: (1) 2-cyano-4-nitraniline is diazotized with a solution of sodium nitrite in concentrated sulphuric acid, and the solution is partly neutralized and coupled with N - ethyl - N-methoxyethylaniline; (2) diazotized 2-cyano-4-nitraniline is coupled with 2-methoxy-5-methyl-N - di(methoxyethyl) - aniline; (3) diazotized 2-cyano-4-nitraniline is coupled with 3-methyl-N - butyl - N - oxyethylaniline; (4) diazotized 2-cyano-4-nitraniline is coupled with 1-amino-5-naphthol; (5) 6-cyano-2 : 4-dinitraniline is diazotized as in example 1 and coupled with 2 - methoxy - 5 - methyl - N - di(methoxyethyl)-aniline or 2-methoxy-5-methyl-N-butyl-N-methoxyethylaniline; (6) diazotized 6-cyano-2 : 4 - dinitraniline is coupled with 2 : 5-dimethoxy - N - di(methoxyethyl) - aniline; (7) diazotized 6-cyano-2 : 4-dinitraniline is coupled with 2-methoxy-5-methyl - N - oxyethyl - N - methoxyethylaniline; (8) diazotized 6-cyano-2 : 4-dinitraniline is coupled with 3-methyl-N-butyl - N - oxyethylaniline; (9) diazotized 2-cyano-4-nitraniline is coupled with 2-amino-8-naphthol-6-sulphonic acid or an N-alkyl or N-aryl derivative thereof to yield blue or violet dyes for wool; (10) the product of example 4 is pasted with a dispersing agent such as turkey red oil, sulphite cellulose lye, or a sulphonated residue from the manufacture of benzaldehyde, and a dyebath for acetate silk is prepared by diluting the paste and adding soap solution; dyeing is then effected at a temperature rising to 85 DEG C. Amines.--The etherified or esterified N-hydroxyalkyl arylamines specified above are obtainable by the methods described in British Specification 422,843 (or French Specification 758,079). 6-Cyano-2 : 4-dinitraniline is obtainable by nitrating 6-cyano-1-methoxybenzene or 6-cyano-4-nitro-1-methoxybenzene, and treating the 6-cyano-2 : 4 - dinitro - 1 - methoxybenzene so obtained with ammonia in methyl alcohol, whereby the methoxy group is replaced by an amino group. The Specification as open to inspection under Sect. 91 refers to the use, as diazo components, of substitution products in general of 1-amino-2-cyano-4-nitro- (or 4 : 6-dinitro-) benzene, and specifies the hydroxy and alkoxy substitution products and also 1-amino-2-cyano-6-chloro-(or bromo- or iodo-)-4-nitrobenzene. This subject-matter does not appear in the Specification as accepted.
GB5852/35A 1934-02-23 1935-02-23 Manufacture of azo-dyestuffs Expired GB447561A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH447561X 1934-02-23

Publications (1)

Publication Number Publication Date
GB447561A true GB447561A (en) 1936-05-21

Family

ID=4515374

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5852/35A Expired GB447561A (en) 1934-02-23 1935-02-23 Manufacture of azo-dyestuffs

Country Status (1)

Country Link
GB (1) GB447561A (en)

Similar Documents

Publication Publication Date Title
US2194927A (en) Azo compound
US2283220A (en) Azo compounds and material colored therewith
GB447561A (en) Manufacture of azo-dyestuffs
US2563091A (en) Dyes
US2217693A (en) Azo compound and process for coloring therewith
US2077322A (en) Process for the manufacture of azo dyestuffs for esters of cellulose and azo dyestuffs obtained therefrom
GB422843A (en) Manufacture of azo-dyestuffs and intermediate products
US2221911A (en) Azo compounds and material colored therewith
US2227977A (en) Azo compounds and material colored therewith
US2231707A (en) Azo compounds and material colored therewith
US2420008A (en) Disazo dyes containing higher acylamino group
GB587467A (en) Manufacture of new azo-dyestuffs
US2412312A (en) Cellulose acetate dyed with monoazo dyes
GB434126A (en) New monoazo dyestuffs
US2286304A (en) Azo dye
US2392180A (en) Azo derivatives of amino diphenylamines
US2289293A (en) Manufacture of azo dyes
US2091367A (en) Azo dyestuffs and their production
GB455643A (en) Manufacture and application of new azo dyestuffs
US2057685A (en) Azo dyestuffs and their production
GB565951A (en) New monoazo pigments
GB462233A (en) Manufacture of azo-dyestuffs
GB456343A (en) Process for the manufacture of water-insoluble azo-dyestuffs
GB434243A (en) Improvements in the manufacture and production of azo dyestuffs
GB593567A (en) Azo dyes