GB422843A - Manufacture of azo-dyestuffs and intermediate products - Google Patents

Manufacture of azo-dyestuffs and intermediate products

Info

Publication number
GB422843A
GB422843A GB19412/33A GB1941233A GB422843A GB 422843 A GB422843 A GB 422843A GB 19412/33 A GB19412/33 A GB 19412/33A GB 1941233 A GB1941233 A GB 1941233A GB 422843 A GB422843 A GB 422843A
Authority
GB
United Kingdom
Prior art keywords
amino
acid
methyl
aniline
group
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
GB19412/33A
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 GB422843A publication Critical patent/GB422843A/en
Expired legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • 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
    • 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
    • C09B62/00Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/54Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an epoxy or halohydrin group
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/22General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

Azo dyes are obtained by introducing into any azo-body at least one group of the type <FORM:0422843/IV/1> in which R1=H, alkyl, aralkyl, acidyl or the group --R2--O--R3, R2=an aliphatic hydrocarbon radicle consisting of at least two carbon atoms, and R3=alkyl, aralkyl, alkylene, alkoyl, aralkoyl or aroyl. Alkyl includes derivatives, e.g. C2H4Cl, C2H4NMe2, C2H4SO3H &c. The process consists in: (1) coupling an aromatic diazo compound with a coupling component containing at least one alkyl-, aralkyl- or alkylene-oxyalkylamino group, or an alkoyl-, aralkoyl- or aroyl-oxyalkylamino group; (2) by reaction of a dyestuff containing a primary or secondary amino-group with an ether or an organic ester of an alcohol, which contains at least one group capable of reacting with the --NH2 or ---NHX group of the dyestuff, X meaning alkyl, aralkyl or acidyl; (3) by etherifying or esterifying with an organic acid or dyestuff containing an o -oxyalkylamino group. According to the components chosen they dye wool, silk, cotton, regenerated cellulose, cellulose esters or ethers, paper, lacquers and varnishes and may be used as pigments. The insoluble dyestuffs, which are especially suitable for dyeing cellulose esters and ethers, may be ground with dispersing agents to form dyestuff preparations. In examples, the following dye-stuffs are described: (1)--(6) and (8)--(10) p-nitraniline, 5-nitro-2-anisidine, 2-chlor-4-nitraniline, sulphanilic acid or 2 : 6-dichlor-4-nitraniline --> b - [(ethylphenyl) - amino] - - ethylmethylether or ethyl - (o - acetoxyethyl) - aniline (red to bordeaux-red); (7) 2 : 4-dinitraniline --> b - [(2 - methoxy - 5 - methyl)-phenylamino] - ethylmethylether. Examples of the dyeing process for acetate artificial silk are also given. Samples have been furnished under Sect. 2 (5) of the following dyestuffs: (1) and (2) p-nitraniline or 2-chlor-4-nitraniline --> [di - (o - methyloxyethyl)] - aminobenzene; (3) and (4) p-nitraniline or 2 : 4-dinitraniline --> 5-methyl-2-methoxy-1-[di-(o -methyloxyethyl]-aminobenzene; (5) 6-chlor-2 : 4-dinitraniline ---> 1-methyloxyethylaminonaphthalene. Other components specified are aniline, toluidines, nitranilines, chloranilines or their sulphonic or carboxylic acids, e.g. metanilic acid, nitrochloranilines, anisidines, nitro- and chloro-anisidines, dinitranilines, dinitrochloranilines, o-aminophenol and its derivatives, e.g. o-aminocresols, nitroaminophenols, e.g. 5-nitro-2-aminophenol, chloraminophenols and their sulphonic acids, naphthylamines and their sulphonic acids, aminoazobenzene and its derivatives, e.g. aminoazotoluenes and aminazobenzenesulphonic acids; b - (phenylamino) - ethylmethylether, b - (phenylamino) - diethylether, b - [(methylphenyl) - amino] - ethylmethylether or-diethylether, b - [(ethylphenyl)amino] - diethylether, b - [(5 - methyl) - phenylamino] - ethylmethyl - ether diethylether, b -[(2-methoxy-5-methyl)-phenylamino] - diethylether, b - [(2 : 5 - dimethoxy) - phenylamino] - ethylmethylether or -diethylether, b - [{(2 - methoxy - 5 - methyl or methoxy) - phenylethyl} - amino] - ethyl - methylether or -diethylether, (o -acetoxyethyl)-aniline, (o - acetoxyethyl) methyl- or -ethyl-aniline and (o - acetoxyethyl) - toluidines or anisidines. The following additional combinations (acetate artificial silk dyes) are also specified: aniline or p-nitraniline ---> b -(phenylamino) - ethylmethylether or -diethylether or (o - acetoxyethyl) - aniline, (yellow to orange red); 5-nitro-2-aminophenol, 4 : 6-dinitro-o-anisidine or 2 : 4-dinitraniline ---> b - [(2 - methoxy - 5 - methyl) - phenylamino] - ethylmethylether or b -[(2 : 5 - dimethoxy) - phenylamino] -ethylmethylether (red violet to violet brown). Arylaminoalkylethers are made (1) by condensing the corresponding amine, e.g. aniline, ethylaniline or 1-amino-2-methoxy-5-methyl-benzene with an ether of a polyhydric alcohol which contains at least one non-etherified OH group or with a sulphuric acid ester or dialkyl ether sulphate or arylsulphonic ester thereof, e.g. the p-toluenesulphonic ester of glycolmonomethyl- or ethyl ether (from the glycol ether and p-toluenesulphochloride); (2) by condensing a halogen-ether with the amine; (3) by etherifying the corresponding arylaminoalcohol; (4) by causing an arylaminohalogenalkyl compound to react with an alcoholate; (5) by causing an aryl compound which contains in the nucleus a substituent capable of reacting (e.g. a halogen in o-position to a nitro group), to react with an aminoalkylether. Thus b - [(ethylphenyl) - amino] - ethylmethyl ether is made from ethylaniline and the p-toluenesulpho ester of glycol monomethylether or by etherifying ethyl-(o -oxyethyl)-aniline by means of a methylhalide and sodium; b - [(2 - methoxy - 5 - methyl) - phenylamino] - ethylmethylether may be similarly made from 1-amino-2-methoxy-5-methylbenzene. The di-(o -methyloxyethyl) compounds required in the preparation of the samples are also prepared in the same manner. Esters of arylaminoalcohols with organic acids are made (1) by condensing the corresponding amine with an organic ester of a polyhydric alcohol, which contains at least one non-esterified OH group, or with sulphuric acid esters or arylsulphonic acid esters thereof; (2) by condensing an organic ester of a halogenated alcohol with the amine; (3) by esterifying the corresponding arylaminoalcohol; (4) by causing an arylaminohalogenalkyl to react with the salt of an organic acid; (5) by reaction between an aryl compound which contains in the nucleus a substituent capable of reaction, e.g. a halogen in o-position to a nitro group, and an organic ester of an amino-alcohol. Thus (acet-o -oxyethyl)-ethylaniline is made from o -oxyethyl-aniline and acetic anhydride in presence of sodium acetate. The Specification as open to inspection under Sect. 91 comprises also the condensation of an azo dyestuff which contains a primary or secondary amino group with a hydrogen halide ester, an arylsulphonic acid ester or sulphonic acid ester of a polyhydric alcohol containing at least one esterified group. In the case of the corresponding ethers [cf. (2) above], the following compounds are specified: <FORM:0422843/IV/2> <FORM:0422843/IV/3> or homologues thereof. In respect of o -oxyalkylamino dyestuffs it is stated that these are obtainable by means of compounds such as Cl.CH2CH2OH, Br--[CH2]3 OH, I--CH2(CHOH)--CH3, Br--[CH2]3--CH (OH)CH3. Dyes containing o -halogenalkylamino groups, e.g. --NH--CH2.CH2Br or --NH--[CH2]3--Br may be treated with an alcoholate or the salt of an organic acid, e.g. sodium formate or acetate. Further components specified are 1 : 8-aminonaphthol sulphonic acids, e.g. H acid or toluene sulphonic acids thereof, aminoazo dyestuffs, e.g. aniline or naphthylamine sulphonic acids ---> aniline, cresidine, a -naphthylamine and its 6- or 7-sulphonic acids and 1-amino-2-methoxynaphthalene; (o -acetoxyethyl)-methyl-toluidines or anisidines, [di(o -ethyloxymethyl)]-aniline, [di-(o - acetoxyethyl)] - aniline, 1 - [(ethyl - oxy - methyl - )amino] - naphthalene, 2 - [(ethyloxy - methyl-)-amino]-naphthalene, <FORM:0422843/IV/4> (obtained by alkylating m-nitraniline and reducing) and the corresponding OH compound (obtained by Sandmeyers reaction). Dyestuffs are also specified in which the group <FORM:0422843/IV/5> is in the diazo component. Aminoazo dyes of the general formula <FORM:0422843/IV/6> e.g. 4 - amino - 4<1> - (ethyl - ethyloxy - methyl)-, 4 - amino - 4<1> - (diethyloxymethyl)-, 4 - amino-4<1>-(o -oxyethyl-ethyl-oxymethyl)-or 4-amino-4<1>-(ethyl-o -acetoxyethyl) - aminoazobenzene, may be diazotized and used for developing cotton which has been prepared with arylides of 2 : 3-oxynaphthoic acid, 2 : 3-oxyanthracene-carboxylic acid, and hydroxycarbazole- or hydroxybenzocarbazolecarboxylic acids; aminoazo compounds of the type <FORM:0422843/IV/7> may also be used. Sulphonated dyestuffs for wool, silk and cotton may be prepared from sulphanilic acid, nitraniline and dehydrothiotoluidine sulphonic acids. 4-Amino-1-[ethyl-ethyloxymethyl] - aminobenzene (obtained by treating [ethyl-ethyloxymethyl]-aminobenzene or [b - (methylphenyl) - amino] - ethylmethyl ether with nitrous acid and reducing) gives blue dyes when diazotized and coupled with periderivatives of naphthalene, e.g. 1 : 8-dioxy-naphthalene or a 1 : 8-aminonaphthol sulphonic acid; if the diazo component contains halogen or SO2--aryl groups, N-acidyl derivatives of 1 : 8-aminonaphthol sulphonic acids may be used as coupling components. Blue dyes are also obtained by hydrolyzing the dyestuffs obtained by coupling N-acidyl derivatives of 4 - diazo - 1 - (mono - ethyloxymethyl) - amino - benzene with 1 : 8-dioxynaphthalene-4- or 3 : 6-disulphonic acid; the acetyl and nitroso compounds are specified as acidyl derivatives. Disazo and polyazo dyes are also specified, e.g. the dyestuff N-(ethyl-methoxyethyl)-aminobenzene \sM benzidine --> H acid \sM p-nitraniline, primary disazo dyes from m-phenylene diamine and aminonaphthol derivatives, and secondary disazo dyes from the aminoazo dye 1-naphthylamine-6-sulphonic acid --> 1 - naphthylamine - 6 - sulphonic acid. In examples, the following dyes are described: (1) 6-chlor-2 : 4-dinitraniline or H acid --> 1-(mono-ethyloxyethyl)aminonaphthalene; (2) 1-methyl-3<1>-amino - 5<1> - sulphonic acid- 4 : 4<1>-diphenylsulphone --> [b -(ethylphenyl)-amino]-ethylmethylether or the product of reaction of p-toluenesulphonic ester and glycol monomethylether with b -naphthylamine; (3) p-cresolester of p-nitraniline-o-sulphonic acid, which is sulphonated in the cresol nucleus --> [b -(ethylphenyl)-amino]-ethylmethylether; (4) cotton is impregnated with the o-anisidide of 2 : 3-oxynaphthoic acid and developed with diazotized 4 - amino - 3 - chloro - 6 - methoxy - 4<1> - [(ethylethyloxymethyl) - amino] - azobenzene or the dyestuff may be produced in substance;
GB19412/33A 1932-07-09 1933-07-08 Manufacture of azo-dyestuffs and intermediate products Expired GB422843A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH422843X 1932-07-09

Publications (1)

Publication Number Publication Date
GB422843A true GB422843A (en) 1935-01-08

Family

ID=4514753

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19412/33A Expired GB422843A (en) 1932-07-09 1933-07-08 Manufacture of azo-dyestuffs and intermediate products

Country Status (1)

Country Link
GB (1) GB422843A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1061927B (en) * 1956-07-18 1959-07-23 Sandoz Ag Process for the preparation of water-insoluble azo dyes
DE1065112B (en) * 1955-07-13 1959-09-10 Sandoz Ag Process for the preparation of water-insoluble monoazo dyes
DE1069114B (en) * 1959-11-19 Badiscbe Anilin- &- Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein Dyeing and printing of structures made from triacetyl cellulose
FR2051806A1 (en) * 1969-07-17 1971-04-09 Sandoz Sa
JPS6041650A (en) * 1983-07-09 1985-03-05 チバ―ガイギー アクチエンゲゼルシヤフト Novel azobenzene compound and negative photoresist composition containing same
CN106543027A (en) * 2016-10-26 2017-03-29 安徽工程大学 A kind of preparation method of amino anthraquinones structural compounds diazol, the modification dyeing of fibroin albumen

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1069114B (en) * 1959-11-19 Badiscbe Anilin- &- Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein Dyeing and printing of structures made from triacetyl cellulose
DE1065112B (en) * 1955-07-13 1959-09-10 Sandoz Ag Process for the preparation of water-insoluble monoazo dyes
DE1061927B (en) * 1956-07-18 1959-07-23 Sandoz Ag Process for the preparation of water-insoluble azo dyes
FR2051806A1 (en) * 1969-07-17 1971-04-09 Sandoz Sa
JPS6041650A (en) * 1983-07-09 1985-03-05 チバ―ガイギー アクチエンゲゼルシヤフト Novel azobenzene compound and negative photoresist composition containing same
EP0134446A1 (en) * 1983-07-09 1985-03-20 MERCK PATENT GmbH Negative photoresist formulations with radiation-absorbing additives
US4762767A (en) * 1983-07-09 1988-08-09 Merck Patent Gesellschaft Mit Beschrankter Haftung Negatively operating photoresist composition, with radiation-absorbing additives
JPH0723960B2 (en) 1983-07-09 1995-03-15 チバ―ガイギー アクチエンゲゼルシヤフト Negative acting photoresist composition containing azobenzene compound
CN106543027A (en) * 2016-10-26 2017-03-29 安徽工程大学 A kind of preparation method of amino anthraquinones structural compounds diazol, the modification dyeing of fibroin albumen

Similar Documents

Publication Publication Date Title
GB209723A (en) Manufacture of new azo-dyestuffs
US2194927A (en) Azo compound
GB422843A (en) Manufacture of azo-dyestuffs and intermediate products
US2034668A (en) Azo dyestuffs
US2045323A (en) Azo-dyestuffs
US1947027A (en) Azo dyes
US3331829A (en) Disazo dyestuffs insoluble in water
GB779487A (en) Manufacture of polyazo-dyestuffs
US1716098A (en) Trisazo dye and process of producing the same
US2289293A (en) Manufacture of azo dyes
US2191801A (en) Polyazo dye compounds
GB453437A (en) Improvements in the manufacture and production of azo dyestuffs
GB462233A (en) Manufacture of azo-dyestuffs
US2167142A (en) Azo dyes
US2155685A (en) Azo dyes
US2055377A (en) Mono-azodyestuffs
GB593567A (en) Azo dyes
US2420008A (en) Disazo dyes containing higher acylamino group
GB513109A (en) A manufacture of azo-dyestuffs and intermediate products
GB434126A (en) New monoazo dyestuffs
GB501855A (en) Manufacture of azo-dyestuffs
US2024368A (en) Monoazo dyes and their production
GB536159A (en) Manufacture of brown polyazo dyestuffs, especially suitable for dyeing leather
GB491793A (en) Improvements in the manufacture and production of azo dyestuffs
US2047574A (en) Azo-dyestuffs and process of making same