GB843644A - Improvements in or relating to new water-insoluble styryl dyestuffs - Google Patents

Improvements in or relating to new water-insoluble styryl dyestuffs

Info

Publication number
GB843644A
GB843644A GB22704/57A GB2270457A GB843644A GB 843644 A GB843644 A GB 843644A GB 22704/57 A GB22704/57 A GB 22704/57A GB 2270457 A GB2270457 A GB 2270457A GB 843644 A GB843644 A GB 843644A
Authority
GB
United Kingdom
Prior art keywords
radical
hydrogen
ethyl
carbon atoms
trimethylindoleninium
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
GB22704/57A
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Publication of GB843644A publication Critical patent/GB843644A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
    • C09B23/146—(Benzo)thiazolstyrylamino dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B39/00—Other azo dyes prepared by diazotising and coupling

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Coloring (AREA)
  • Artificial Filaments (AREA)

Abstract

Cellulose esters and synthetic polymers are spun-dyed with a water-insoluble dyestuff of the formula: <FORM:0843644/IV(a)/1> where A is cyano, carbalkoxy, carbalkoxyalkoxy or a phenyl-diphenylyl, naphthyl- or tetrahydronaphthyl-monosulphonyl radical, the sulphonyl group being attached to the aromatic ring thereof, or a 1 : 3 :3-trimethylindoleninium radical linked in the 2-position when n is 1, or a diphenylene - or naphthylene-disulphonyl radical when n is 2, x is hydrogen, methyl, ethyl, methoxy or ethoxy, y is hydrogen, methyl, ethyl, methoxy, or ethoxy, or when A is 1 : 3 :3-trimethylindoleninium also halogen or trifluoromethyl, R1 and R2 are alkylene radicals of 1 to 4 and 2 to 4 carbon atoms respectively, R3 is an aliphatic, cycloaliphatic or aromatic radical free from water-solubilizing groups, one V is oxygen and the other V is -NH-, M is hydrogen, alkyl of not more than 5 carbon atoms, cyanomethyl, tri- or bi-fluoromethyl, carboalkoxy or the R3-V-CO-V- radical when A is a 1 : 3 : 3-trimethylindoleniuium radical, or, when A has another meaning, hydrogen, alkyl or alkoxy of not more than 5 carbon atoms or R3-V-CO-V-, T is hydrogen when A is 1 : 3 : 3-trimethylindoleninium or cyano when A has another meaning, and n is 1 or 2. In examples, solutions of (2) and (164) cellulose acetate in acetone-methanol, (153) cellulose triacetate in methylene chloride-ethanol, (154) polyethylene in xylene, (155) polyvinyl chloride in cyclohexanone-ethylhexanone, (156) postchlorinated polyvinylchloride in acetone and diethyl sulphide, (157) a copolymer of vinyl chloride and acrylontrile in acetone, and (158) and (159) polyacrylonitrile in dimethylformanide are mixed with dyestuff solutions and spun; in other examples (160) Rilson, (161) nylon, and (162) the condensate of terephthalic acid and glycol or of the dimethyl ester and glycol are mixed with the dyestuff and melted and spun: example 163 also illustrates the spin-dyeing of polyethylene and polystyrene. Specification 843,645 is referred to.ALSO:1 - [N-ethyl-N-beta-(phenylcarbamyloxy) -ethyl]-amino-3-methyl-4-benzaldehyde is made by heating 1-[N-ethyl-N-beta-(phenylcarbamyloxy) -ethyl]-amino-3-methyl-benzene with phosphorous oxychloride and N:N-dimethylformamide and the reaction mass poured into water. Specification 843,645 is referred to.ALSO:The invention comprises water-insoluble styryl dyestuffs of the formula: <FORM:0843644/IV (c)/1> where A is cyano, carbalkoxy, carbalkoxyalkoxy, or a phenyl-, diphenylyl-, naphthyl- or tetrahydronaphthyl - monosulphonyl radical which may be substituted by halogen or alkyl groups of less than 6 carbon atoms, the sulphonyl group being attached to the aromatic ring of the tetrahydronaphthyl radical, or a 1 : 3 : 3-trimethylindoleninium radical linked in the 2-position and further substituted if desired, when n is 1, or a diphenylene- or naphthylene-disulphonyl radical which may be substituted, when n is 2, x is hydrogen, methyl, ethyl, methoxy or ethoxy, y is hydrogen, methyl, ethyl, methoxy or ethoxy or, when A is 1 : 3 : 3-trimethylindoleninium, also halogen or trifluoromethyl, R1 is an alkylene radical of 1 to 4 carbon atoms, R2 is an alkylene radical of 2 to 4 carbon atoms, R3 is an aliphatic, cycloaliphatic or aromatic radical which is free from water-solubilizing groups and may be further substituted, one V is oxygen and the other V is the -NH- group, M is hydrogen, alkyl or alkoxy of not more than 5 carbon atoms, cyanomethyl, difluoromethyl, trifluoromethyl, carbalkoxy, or the R3-V-CO-V- radical, when A is a 1 : 3 : 3-trimethylindoleninium radical, or, when A has another meaning, hydrogen, alkyl or alkoxy of not more than 5 carbon atoms or R3-V-CO-V-, T is hydrogen when A is 1 : 3 : 3-trimethylindoleninium or cyano when A has another meaning, and n is 1 or 2. The dyestuffs are made by reacting 1 mole of an appropriate aldehyde of the formula: <FORM:0843644/IV (c)/2> with one mole of malonic acid dinitrile or of an alkyl ester or alkoxyalkyl ester of cyanoacetic acid or a phenylsulphonyl or diphenylylsulphonyl or tetrahydronaphthylmonosulphonyl or naphthylmonosulphonyl acetonitrile or a 1 : 3 : 3 -trimethyl-2-methylene-indolenine, or 2 moles of the above aldehyde with one mole of a naphthylenedisulphonyl or diphenylenedisulphonyl acetonitrile. Many examples are given. The dyestuffs dye or spin-dye cellulose esters, synthetic polymers, oils and lacquer media. Specification 843,645 is referred to.
GB22704/57A 1956-07-18 1957-07-17 Improvements in or relating to new water-insoluble styryl dyestuffs Expired GB843644A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH843644X 1956-07-18

Publications (1)

Publication Number Publication Date
GB843644A true GB843644A (en) 1960-08-04

Family

ID=4541566

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22704/57A Expired GB843644A (en) 1956-07-18 1957-07-17 Improvements in or relating to new water-insoluble styryl dyestuffs

Country Status (4)

Country Link
CH (2) CH353732A (en)
DE (2) DE1061955B (en)
FR (2) FR1216235A (en)
GB (1) GB843644A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2286861A1 (en) * 1974-10-04 1976-04-30 Sandoz Sa NEW STYRYLIC DYES AND THEIR PREPARATION

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL258146A (en) * 1959-11-21
NL275143A (en) * 1961-02-23
US3247211A (en) * 1963-01-18 1966-04-19 Eastman Kodak Co Cyanomethylidene quinolines
DE1245005B (en) * 1964-01-17 1967-07-20 Bayer Ag Process for the preparation of styryl dyes
NL169605C (en) * 1971-06-25 1982-08-02 Duphar Int Res METHOD FOR PREPARING NEW COLORANTS AND METHOD FOR COLORING MATERIALS AND ARTICLES
CN103590192B (en) * 2013-10-15 2016-01-06 浙江三志纺织有限公司 The coloured nanofiber membrane preparation method of Disperse Blue 2BLN/polyacrylonitrile-radical

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2286861A1 (en) * 1974-10-04 1976-04-30 Sandoz Sa NEW STYRYLIC DYES AND THEIR PREPARATION

Also Published As

Publication number Publication date
DE1067156B (en)
CH358534A (en) 1961-11-30
FR1182373A (en) 1959-06-24
DE1061955B (en) 1959-07-23
CH353732A (en) 1961-04-30
FR1216235A (en) 1960-04-22

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