GB840282A - Dyestuffs for the dyeing and printing of polymers or co-polymers of acrylonitrile oras-dicyanethylene - Google Patents

Dyestuffs for the dyeing and printing of polymers or co-polymers of acrylonitrile oras-dicyanethylene

Info

Publication number
GB840282A
GB840282A GB833358A GB833358A GB840282A GB 840282 A GB840282 A GB 840282A GB 833358 A GB833358 A GB 833358A GB 833358 A GB833358 A GB 833358A GB 840282 A GB840282 A GB 840282A
Authority
GB
United Kingdom
Prior art keywords
alkyl
indole
phenyl
indoline
methylene
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
GB833358A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB840282A publication Critical patent/GB840282A/en
Expired legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00General methods for the manufacture of artificial filaments or the like
    • D01F1/02Addition of substances to the spinning solution or to the melt
    • D01F1/06Dyes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/08Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415Five-membered rings
    • C08K5/3417Five-membered rings condensed with carbocyclic rings
    • 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
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10The polymethine chain containing an even number of >CH- groups
    • C09B23/105The polymethine chain containing an even number of >CH- groups two >CH- groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Coloring (AREA)

Abstract

The dimethine dyestuff produced by condensing 1 - methyl - 2 - phenyl - indole - 3 - aldehyde and 5 - methoxy - 1:3:3 - trimethyl - 2 - methylene-indoline is mixed with polyacrylonitrile and dimethyl formamide, and spun in known manner. It is stated that other dyes may be used having the general formula <FORM:0840282/IV(a)/1> wherein A is an alkoxy, hydroxyalkyl or a carboxylic alkyl or hydroxyalkyl ester group, R1 is alkyl, R2 is H or alkyl, X is H or a non-ionic substituent and Y is an anion.ALSO:Methine dyes of the general formula: <FORM:0840282/IV (c)/1> wherein A is an alkoxy, hydroxyalkoxy or a carboxylic alkyl or hydroxyalkyl ester group, R1 is alkyl, R2 is H or alkyl, X is H or a nonionic substituent and Y is an anion, are prepared by condensing in acid medium a 2-phenyl-indole-3-aldehyde with a 5-substituted -1;3;3-trialkyl-2-methylene-indoline, or a 2-phenyl-indole with a 5-substituted -1;3;3-trialkyl-2-formyl-methylene -indoline. Alternatively, a 2-phenyl-indole and a 5-substituted-11, 31, 3-trialkyl -2- methylene indoline may be reacted in the presence of formyl methyl aniline or formyl diphenylamine and a phosphorus halide of oxyhalide. The substituent X may be halogen, alkyl or alkoxy. Examples are given of the condensation of 2-phenyl-indole-3-aldehyde which may have 1-methyl, 1; 5-dimethyl, 1-methyl-5-chloro or 1-methyl-5-methoxy substituents with a 1; 3; 3-trimethyl-2-methylene indoline having in the 5-position a methoxy, ethoxy, hydroxylthoxy, or carboxylic acid methyl, ethyl or hydroxyethyl ester group. In Example 4 2-phenyl-indole is reacted with 5-ethoxy-1; 3; 3-trimethyl-2-formyl-methylene-indoline and in Example 5, 2-phenyl-indole and 5-carbo-methoxy-1; 3; 3-trimethyl-2-methylene-indoline are reacted with formyl methyl aniline in the presence of phosphorus oxychloride. The dyes may be used in neutral or acid medium for dyeing or printing fibres of polymers or co-polymers of acrylonitrile or dicyanethylene, including polyacrylonitrile mixed with wool. The acid baths may contain glacial acetic, oxalic, hydrohalic, sulphuric, formic, phosphoric or p-toluene sulphonic acids. The dyeing baths may also contain Glauber's salt, sodium acetate, sodium chloride, dispersing agents such as soap, cellulose sulphate liquor, fatty alcohol sulphonates, higher alkyl sulphonic acids and condensation products of high molecular weight alcohols and ethylene oxide; or retarders and levelling agents such as the condensation products of high molecular weight alcohols and ethylene oxide, polyglycol ethers of fatty acid amides and condensation products of aromatic sulphonic acids and formaldehyde.
GB833358A 1957-03-28 1958-03-14 Dyestuffs for the dyeing and printing of polymers or co-polymers of acrylonitrile oras-dicyanethylene Expired GB840282A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF22687A DE1044022B (en) 1957-03-28 1957-03-28 Process for coloring and printing polymers or mixed polymers of acrylonitrile or as-dicyanaethylene

Publications (1)

Publication Number Publication Date
GB840282A true GB840282A (en) 1960-07-06

Family

ID=7090535

Family Applications (2)

Application Number Title Priority Date Filing Date
GB833358A Expired GB840282A (en) 1957-03-28 1958-03-14 Dyestuffs for the dyeing and printing of polymers or co-polymers of acrylonitrile oras-dicyanethylene
GB1578058A Expired GB869794A (en) 1957-03-28 1958-05-16 Methine dyestuffs

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB1578058A Expired GB869794A (en) 1957-03-28 1958-05-16 Methine dyestuffs

Country Status (6)

Country Link
BE (2) BE566117A (en)
CH (3) CH394445A (en)
DE (2) DE1044022B (en)
FR (2) FR1205267A (en)
GB (2) GB840282A (en)
NL (2) NL104765C (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE595491A (en) * 1959-09-30
NL126390C (en) * 1962-04-10
DE2822913C2 (en) * 1978-05-26 1982-08-19 Hoechst Ag, 6000 Frankfurt Process for spin dyeing polymers or copolymers of acrylonitrile

Also Published As

Publication number Publication date
GB869794A (en) 1961-06-07
CH5582258A4 (en) 1963-05-31
BE566117A (en) 1958-04-15
FR1205267A (en) 1960-02-02
CH5918358A4 (en) 1965-01-15
CH383529A (en) 1965-01-15
FR1206880A (en) 1960-02-12
DE1044022B (en) 1958-11-20
NL104629C (en) 1963-05-15
CH330463A4 (en) 1965-11-30
BE567902A (en) 1958-06-14
CH368565A (en) 1963-05-31
CH394445A (en) 1965-11-30
NL104765C (en) 1963-05-15
DE1049994B (en)

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