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GB646123A - Process for the manufacture of polymethine dyestuffs - Google Patents

Process for the manufacture of polymethine dyestuffs

Info

Publication number
GB646123A
GB646123A GB11280/46A GB1128046A GB646123A GB 646123 A GB646123 A GB 646123A GB 11280/46 A GB11280/46 A GB 11280/46A GB 1128046 A GB1128046 A GB 1128046A GB 646123 A GB646123 A GB 646123A
Authority
GB
United Kingdom
Prior art keywords
pyrazolone
methyl
phenyl
heating
acid
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
GB11280/46A
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.)
Gevaert Photo Producten NV
Original Assignee
Gevaert Photo Producten NV
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 Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Publication of GB646123A publication Critical patent/GB646123A/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
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0066Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Coloring (AREA)

Abstract

Symmetrical or unsymmetrical dyes of the general formula <FORM:0646123/IV (c)/1> wherein m and n are 1 or 2, Y and Z are the non-metallic atoms to complete carbocyclic or heterocyclic rings, which may have fused-on rings attached thereto, and X is the non-metallic atoms to complete a carbocyclic or heterocyclic ring with any 2 carbon atoms of the polymethine chain, wherein X, Y and Z may form identical or different rings, wherein the remaining H-atoms of the polymethine chain may be replaced by alkyl, aryl, aralkyl, acyl, or carboxyethyl groups, e.g. acetyl, p-iodophenyl, or 2-pyridyl groups, and wherein the hydrogen of the enol group may be replaced by metals (e.g. Na, K, Ca, or Ag), triethylammonium or acetyl, are prepared by the condensation in molecular proportion of carbocyclic or heterocyclic 5- or 6-membered compounds containing a reactive methylene group next to a CO group with compounds of the general formula <FORM:0646123/IV (c)/2> wherein V is O, N-aryl, or (O-alkyl)2 and W is OH, ONa O-alkyl, O-CO-alkyl, O-CO-aryl, halogen, or a substituted amino group or, where Y and Z complete identical rings, by condensing two moles of the first reactant with one mole of a compound of the general formula <FORM:0646123/IV (c)/3> or, where X, T and Z complete identical rings, by condensing three moles of the first reactant with one mole of a compound of the general formula V=CH-W. X may be butylene, o-phenylene, or complete a pyrazole or isoxazole ring. The first reactant may be 1 : 3-indanedione, 3-phenyl-5-isoxazolone, 3-methyl-5-pyrazolone, 1 - phenyl - 3 - methyl - 5 - pyrazolone, 1 : 11 - (diphenylen - 4 : 41) - bis - (3 - methyl-5-pyrazolone), barbituric acid, thiobarbituric acid, rhodanine, phenylrhodanine, pseudothiohydantoin, and derivatives such as sulphonic acids. Compounds of general formula (A) or (B) specified are 4 : 41-methenyl-bis-1-phenyl-3-methyl-5-pyrazolone and its disulphonic acid, bi-indone, methenyl-bis-indanedione, and 1-phenyl - 3 - methyl - 4 - (3 - oxo - 2 - phenyl-hydrindyliene) - pyrazolone - 5. Compounds of general formula (C) specified are hydroxymethylenecyclopentanone, hydroxymethylenecyclohexanone, a 5 - pyrazolone - 4 - aldehyde such as a 1-aryl-3-alkyl-5-pyrazolone-4-aldehyde or compounds wherein the O of the aldehyde group is replaced by =N-aryl or (O-alkyl)2, 2-hydroxythionaphthen-3-aldehyde, hydroxymethylenecamphor, hydroxymethylenedihydroisophorone, 1 : 11-dimethylcyclohexane-3 : 5-dione, ethyl 1 : 3-indanedione-2-carboxylate, benztetronic acid, 1-chlorocyclohexanone-3, 1-benzoyloxy-3-oxo-2-phenylindene, derivatives of homophthaldehyde such as o-formyl-styrylaminosulphonic acid, and the substituted glutaconic dialdehydes obtained by condensing chlorosulphonic acid or 2 : 4-dinitro-chlorobenzene with pyridine derivatives substituted by side-rings, such as cinchomeronic anhydride and cinchomeronimidine. Compounds of the general formula V=CH-W specified are diphenylformamidine, diphenylacetamidine, and ethyl orthoformate. Compounds readily splitting off the compound V=CH-W, e.g. 1-phenyl-2 : 3-dimethyl-5-pyrazolone - 4 - aldehyde, 2 - hydroxynaphthyl-1 - aldehyde, and a - methylindole - b - aldehyde may be used. Indanedione derivatives may be replaced by perinaphthindanedione, 8 - phenyl - perinaphtindanedione - 7 : 9, or derivatives obtained from naphthalic anhydride or nitronaphthalic anhydride and p-nitro-phenyleneacetic acid. Dimalonylperylene may be used as starting material. Dyes may be obtained from the pyrazolone from dehydrothiotoluidine monosulphonic acid and 1-phenyl-3 - methyl - 5 - pyrazolone - 4 - carboxylic acid, and dyes containing three 1 : 11-(di-phenylene-4 : 41) - bis - (3 - methyl - 5 - pyrazolone)-nuclei may be formed. In examples, dyes are obtained (1) by heating a methanol solution of KOH, 1 - phenyl - 3 - methyl - 5 - pyrazolone, and 4 : 41 - methenyl - bis - (1 - phenyl - 3-methyl - 5 - pyrazolone), the purple-red enol dye obtained being convertible into an orange-red ketone dye by acidification; (2) as (1) using 1 - p - sulphophenyl - 3 - methyl - 5-pyrazolone; (3) by acetylating the enol dye of (1) by heating with acetic anhydride and dry sodium acetate; (4) by heating a methanol solution of 1 - phenyl - 3 - methyl - 5 - pyrazolone, 4 : 41 - methenyl - bis - 1 - p - sulphophenyl - 3 - methyl - 5 - pyrazolone, and aqueous ammonia; (5) as (4) using NaOH in place of aqueous ammonia to give a pentamethine dye; (6) by heating a methanol solution of the ammonium salt of 1-p-sulphophenyl - 3 - methyl - 5 - pyrazolone and sodium hydroxymethylenecyclohexanone; (7) as (6) using hydroxymethylenecamphor; (8) by heating a methanol solution of 1-phenyl-3-methyl-5-pyrazolone, 1 : 1 - dimethylcyclohexane-3 : 5-dione, and triethylamine; (9) by heating together 1 - phenyl - 3 - methyl - 5 - pyrazolone and sodium 1 : 3 - indanedione - 2 - carboxylate; (10) by reacting together in warm water the sodium salts of 1 : 3-indanedione-2-carboxylic acid and 1-p-sulphophenyl-3-methyl-5-pyrazolone, and heating with a further quantity of the latter salt; (11) by heating an ethanol solution of diphenylformamidine, 1-phenyl - 3 - methyl - 5 - pyrazolone, and KOH (a mixture of ether and alcohol as solvent gives the intermediate product 4 : 41-methenyl-bis-(1 - phenyl - 3 - methyl - 5 - pyrazolone); and (12) by heating a methanol solution of phenylisoxazole, diphenylformamidine, and KOH. Specifications 506,385, [Group XX], and 515,998, [Group IV], are referred to. The Specification as open to inspection under Sect. 91 comprises also the subject-matter of Specification 646,125, [Group XX]. This subject-matter does not appear in the Specification as accepted.
GB11280/46A 1941-05-22 1946-04-12 Process for the manufacture of polymethine dyestuffs Expired GB646123A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE646123X 1941-05-22

Publications (1)

Publication Number Publication Date
GB646123A true GB646123A (en) 1950-11-15

Family

ID=6580822

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11280/46A Expired GB646123A (en) 1941-05-22 1946-04-12 Process for the manufacture of polymethine dyestuffs

Country Status (4)

Country Link
BE (1) BE445645A (en)
ES (1) ES157456A1 (en)
FR (1) FR882213A (en)
GB (1) GB646123A (en)

Also Published As

Publication number Publication date
BE445645A (en)
FR882213A (en) 1943-05-21
ES157456A1 (en) 1943-03-01

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