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US4426533A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for producing bismethine isoindolines

Assignee: BASF Corp
•
Filing: 1982-03-29
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Granted: 1984-01-17
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Expires: 2002-03-29
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Abstract

Abstract A process for producing bismethine isoindolines of the formula ##STR1## in which process the condensation of 1 mol of any one of the compounds of the formulae ##STR2## with 2 mols of a cyanomethylene compound of the formula NC-CH 2 -R 1 or NC-CH 2 -R 2 , or with 1 mol of a cyanomethylene compound of the formula NC-CH 2 -R 1 and 1 mol of a cyanomethylene compound of the formula NC-CH 2 -R 2 , wherein the symbols have the meanings defined in the specification, is performed in a polar solvent in the presence of a strong base, and the bismethine isoindoline obtained is isolated from the reaction mixture by hydrolysis. The bismethine isoindolines are suitable for pigmenting high-molecular organic material, particularly lacquers.

Inventors

  • 👤 Alain C. Rochat
  • 👤 Luigi Cassar

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 19:34
CPC Classifications
C; C07; C07D; C07D403/00; C07D403/02; C07D403/06; C07D209/00; C07D209/02; C07D209/44; C07D403/12; C09; C09B; C09B57/00; C09B57/04

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 303 words
A process for producing bismethine isoindolines of the formula ##STR15## wherein T 1 to T 4 are hydrogen or halogen, or one or two of the radicals T 1 to T 4 are alkyl, alkoxy or phenoxy, and R 1 and R 2 independently of one another are each cyano, alkyl- or arylcarbonyloxy, carbamoyl, alkylcarbamoyl, or radicals of the formulae II to IV ##STR16## wherein X 1 is a non-solubilising group, and X 2 and X 3 are hydrogen, halogen, alkyl, alkoxy or alkoxycarbonyl, or together form an --NR'--CO--NR"-- group, in which R' and R" independently of one another are hydrogen or C 1 -C 4 -alkyl, and Y 1 and Y 2 are hydrogen, halogen, alkyl or alkoxy, or together form a fused-on benzene ring, V is oxygen, sulfur, imino or alkylimino having 1 to 4 C atoms, and Z 1 and Z 2 have the meanings of Y 1 and Y 2 , in which process the condensation of 1 mol of a compound of the formula V, VI or VII or of the salts of VI or VII ##STR17## wherein T 1 to T 4 have the meanings defined above, and R 3 and R 4 are identical or different and are C 1 -C 4 -alkyl, or together form the group --CH 2 --CH 2 --, with 2 mols of a cyanomethylene compound of the formula NC--CH.sub.2 --R.sub.1 (VIII) or NC--CH.sub.2 --R.sub.2 (IX), or with 1 mol of a cyanomethylene compound of the formula VIII and 1 mol of a cyanomethylene compound of the formula IX, wherein R 1 and R 2 have the meanings defined above, is performed in a polar solvent in the presence of a strong base, and the bismethine isoindoline obtained is isolated from the reaction mixture by hydrolysis in the presence of an acid.
Claim 2
Dependent Claim 303 words
A process for producing bismethine isoindolines of the formula ##STR15## wherein T 1 to T 4 are hydrogen or halogen, or one or two of the radicals T 1 to T 4 are alkyl, alkoxy or phenoxy, and R 1 and R 2 independently of one another are each cyano, alkyl- or arylcarbonyloxy, carbamoyl, alkylcarbamoyl, or radicals of the formulae II to IV ##STR16## wherein X 1 is a non-solubilising group, and X 2 and X 3 are hydrogen, halogen, alkyl, alkoxy or alkoxycarbonyl, or together form an --NR'--CO--NR"-- group, in which R' and R" independently of one another are hydrogen or C 1 -C 4 -alkyl, and Y 1 and Y 2 are hydrogen, halogen, alkyl or alkoxy, or together form a fused-on benzene ring, V is oxygen, sulfur, imino or alkylimino having 1 to 4 C atoms, and Z 1 and Z 2 have the meanings of Y 1 and Y 2 , in which process the condensation of 1 mol of a compound of the formula V, VI or VII or of the salts of VI or VII ##STR17## wherein T 1 to T 4 have the meanings defined above, and R 3 and R 4 are identical or different and are C 1 -C 4 -alkyl, or together form the group --CH 2 --CH 2 --, with 2 mols of a cyanomethylene compound of the formula NC--CH.sub.2 --R.sub.1 (VIII) or NC--CH.sub.2 --R.sub.2 (IX), or with 1 mol of a cyanomethylene compound of the formula VIII and 1 mol of a cyanomethylene compound of the formula IX, wherein R 1 and R 2 have the meanings defined above, is performed in a polar solvent in the presence of a strong base, and the bismethine isoindoline obtained is isolated from the reaction mixture by hydrolysis in the presence of an acid.
Claim 3
Dependent Claim 38 words
A process according to claim 1, wherein the starting material used is a compound of the formula V, VI or VII in which T 1 to T 4 are hydrogen, and R 3 and R 4 are methyl.
Claim 4
Dependent Claim 27 words
A process according to claim 1, wherein the starting material used is a compound of the formula V in which T 1 to T 4 are hydrogen.
Claim 5
Dependent Claim 102 words
A process according to claim 1, wherein the starting materials used are cyanomethylene compounds of the formulae VIII to IX having the radicals R 1 and R 2 of the formulae II to IV in which X 1 is hydrogen, bromine, chlorine or carbamoyl, or phenylcarbamoyl unsubstituted or substituted by chlorine or methyl, X 2 and X 3 are hydrogen, fluorine, bromine or chlorine, or together form a carbodiimino group, wherein an imino group can be substituted by methyl, and Y 1 , Y 2 , Z 1 and Z 2 are hydrogen, bromine, chlorine, methyl or methoxy, and V is imino.
Claim 6
Dependent Claim 43 words
A process according to claim 1, wherein the starting materials used are cyanomethylene compounds of the formulae VIII to IX having the radicals R 1 and R 2 of the formula II in which X 1 to X 3 are hydrogen or chlorine.
Claim 7
Dependent Claim 21 words
A process according to claim 1, wherein the starting materials used are unsubstituted phthalonitrile and cyanomethylene compounds of the formulae ##STR18##
Claim 8
Dependent Claim 14 words
A process according to claim 1, wherein the polar solvent used is an alcohol.
Claim 9
Dependent Claim 20 words
A process according to claim 1, wherein the strong base used is an alkali hydroxide, alkali carbonate or alkali alcoholate.
Claim 10
Dependent Claim 16 words
A process according to claim 1, wherein the base is used together with a phase-transfer catalyst.
Claim 11
Dependent Claim 20 words
A process according to claim 1, wherein the condensation is performed, through all reaction stages, in the same reaction medium.
Claim 12
Dependent Claim 16 words
A process according to claim 1, wherein an organic acid is used for the hydrolysis reaction.

References Cited (Backward Citations)

GB1113530A Cited
DE1268621B Cited
US3390149A Cited
US3646033A Cited
US3758497A Cited
DE2041999C3 Cited
DE2814526A1 Cited
GB2013230B Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-01-16 1987-07-18 1988-01-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-01-16 1991-07-18 1992-01-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-01-16 1995-07-18 1996-01-17 $7700.00 Window Closed / Lapsed

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