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US 4,367,173 AGranted
Azo pigments containing pyrazoloquinazolone radicals
AssigneeBASF SE
InventorHartmut Kanter
Life of this patent
Estimating the term…
Abstract
Azo compounds of the formula: ##STR1## wherein D is a radical of the formula: ##STR2## where Y.sup.1 is acylamino, hydrogen, chlorine, bromine, nitro, cyano, carboxylic acid or ester, trifluoromethyl, alkoxy, methylsulfonyl, and substituted or substituted carbamyl or sulfamyl, phenylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, oxodiazolyl, quinazolonyl phthalazinonyl, phenylazo, naphthylazo, or pyridylazo, Y.sup.2 is hydrogen, chlorine or bromine, Y.sup.4 is hydrogen or chlorine, and wherein D is free from complex forming hydroxy or carboxy; R is hydrogen, phenyl, naphthyl or pyridyl and X is alkyl or a carboxylic acid alkyl ester, or is phenyl, naphthyl or pyridyl, or acylamino, can be used as pigments for coloring surface coatings, printing inks or plastics.
Claims5
An azo compound of the formula ##STR341## wherein D is a radical of the formula ##STR342## where Y.sup.1 is acylamino selected from the group consisting of NHCOCH.sub.3, NHCOC.sub.2 H.sub.5, NHCOC.sub.3 H.sub.7, NHCOC6H.sub.5, NHCOC.sub.6 H.sub.4 Cl, NHCOC.sub.6 H.sub.3 Cl.sub.2, NHCOC.sub.6 H.sub.4 Br.sub.1, NCOC.sub.6 H.sub.4 OCH.sub.3, NHCOC.sub.10 H.sub.7, NHCONHC.sub.6 H.sub.5, ##STR343## Y.sup.1 is hydrogen;
- chlorine;
- bromine, nitro;
- cyano, a carboxylic acid ester having an ester radical selected from the group consisting of C.sub.1 -C.sub.6 alkyl or alkoxy-alkyl, phenyl and benzyl;
- trifluoromethyl;
- alkoxy;
- methylsulfonyl;
- quinazolonyl;
- phthalazinonyl;
- phenylazo;
- naphthylazo;
- pyrodiylazo;
- or unsubstituted or substituted carbamyl or sulfamyl wherein the substituent radicals are selected from the group consisting of NH.sub.2, NHCH.sub.3, NHC.sub.2 H.sub.5, NHC.sub.3 H.sub.7, NHC.sub.4 H.sub.9, ##STR344## NHCH.sub.2 C.sub.6 H.sub.5, NHC.sub.6 H.sub.4 Cl, NHC.sub.6 H.sub.3 Cl.sub.2, NHC.sub.6 H.sub.2 Cl.sub.3, NHC.sub.6 H.sub.4 Br, NHC.sub.6 H.sub.4 OCH.sub.3, NHC.sub.6 H.sub.4 OC.sub.2 H.sub.5, NHC.sub.6 H.sub.3 ClOCH.sub.3, NHC.sub.6 H.sub.4 NHCOCH.sub.3, NHC.sub.6 H.sub.4 NHCOC.sub.6 H.sub.5, NHNHCOC.sub.6 H.sub.5, NHNHCOC.sub.6 H.sub.4 Cl, NHNHCOC6H.sub.4 CH.sub.3, NHC.sub.6 H.sub.3 ClCH.sub.3, NHC.sub.6 H.sub.2 Cl.sub.2 OCH.sub.3 and NHC.sub.6 H.sub.2 Cl.sub.2 CH.sub.3 ;
- Y.sup.2 is hydrogen, chlorine, bromine, nitro, cyano, a carboxylic acid ester having an ester radical selected from the group consisting of C.sub.1 -C.sub.6 alkyl or alkoxy-alkyl, phenyl and benzyl;
- or Y.sup.2 is oxdiazolyl,
- Y.sup.3 is hydrogen, chlorine or bromine;
- Y.sup.4 is hydrogen or chlorine;
- and wherein D is free from complex-forming hydroxy or carboxy;
- R is hydrogen;
- X is alkyl, or a carboxylic acid alkyl ester having an alkyl ester radical selected from the group consisting of C.sub.1 -C.sub.6 alkyl or alkoxyalkyl, phenyl and benzyl;
- or X is phenyl, naphthyl or pyridyl which are unsubstituted or substituted by chlorine, bromine, nitro, methyl, methoxy or ethoxy;
- or X is acylamino selected from the group consisting of NHCOCH.sub.3, NHOCOC.sub.2 H.sub.5, NHCOC.sub.3 H.sub.7, NHCOC.sub.6 H.sub.5, NHCOC.sub.6 H.sub.4 Cl, NHCOC.sub.6 H.sub.3 Cl.sub.2, NHCOC.sub.6 H.sub.4 Br, NHCOC.sub.6 H.sub.4 OCH.sub.3, NHCOC.sub.10 H.sub.7, NHCOHN.sub.2, NHCONHC.sub.6 H.sub.5, ##STR345## and the ring A is substituted or unsubstituted, with the proviso that said ring A is free from SO.sub.3 H groups.
18 more elements
An azo compound of the formula:
- ##STR346## wherein D is a radical of the formula:
- ##STR347## where Y.sup.1 is acylamino selected from the group consisting of NHCOCH.sub.3, NHCOC.sub.2 H.sub.5, NHCOC.sub.3 H.sub.7, NHCOC.sub.6 H.sub.5, NHCOC.sub.6 H.sub.4 Cl, NHCOC.sub.6 H.sub.3 Cl.sub.2, NHCOC.sub.6 H.sub.4 Br, NHCOC.sub.6 H.sub.4 OCH.sub.3, NHCOC.sub.10 H.sub.7, NHCONH.sub.2, NHCONHC.sub.6 H.sub.5 ;
- ##STR348## Y.sup.1 is hydrogen;
- chlorine;
- bromine, nitro;
- cyano;
- a carboxylic acid alkyl ester having an alkyl radical selected from the group consisting of C.sub.1 -C.sub.6 alkyl or alkoxy alkyl, phenyl and benzyl;
- trifluoromethyl;
- alkoxy;
- methylsulfonyl;
- phenylcarbonyl;
- naphthylcarbonyol;
- pyridylcarbonyl;
- oxdiazolyl;
- quinazolonyl;
- phthalazinoyl;
- phenylazo;
- naphthylazo;
- pyridylazo;
- or unsbustituted or substituted carbamyl or sulfamyl wherein the substituent radicals are selected from the group consisting of NH.sub.2, NHCH.sub.3, NHC.sub.2 H.sub.5, NHC.sub.3 H.sub.7, NHC.sub.4 H.sub.9, ##STR349## NHCH.sub.2 C.sub.6 H.sub.5, NHC.sub.6 H.sub.4 Cl, NHC.sub.6 H.sub.3 Cl.sub.2, NHC.sub.6 H.sub.2 Cl.sub.3, NHC.sub.6 H.sub.4 Br, NHC.sub.6 H.sub.4 OCH.sub.3, NHC.sub.6 H.sub.4 OC.sub.2 H.sub.5, NHC.sub.6 H.sub.3 ClOCH.sub.3, NHC.sub.6 H.sub.4 NHCOCH.sub.3, NHC.sub.6 H.sub.4 NHCOC.sub.6 H.sub.5, NHNHCOC.sub.6 H.sub.5, NHNHCOC.sub.6 H.sub.4 Cl, NHNHCOC.sub.6 H.sub.4 CH.sub.3, NHC.sub.6 H.sub.3 ClCH.sub.3, NHC.sub.6 H.sub.2 Cl.sub.2 OCH.sub.3 and NHC.sub.6 H.sub.2 Cl.sub.2 CH.sub.3 ;
- Y.sup.2 is hydrogen, chlorine, bromine, nitro, cyano, a carboxylic acid alkyl ester having an alkyl radical selected from the group consisting of C.sub.1 -C.sub.6 alkyl or alkoxy alkyl, phenyl and benzyl;
- or oxidazoly,
- Y.sup.3 is hydrogen, chlorine or bromine;
- Y.sup.4 is hydrogen, chlorine;
- and
- wherein D is free from complex-forming hydroxy or carboxy,
- R is hydrogen;
- R.sup.1 is hydrogen, fluorine, chlorine, bromine, nitro, C.sub.1 -C.sub.4 alkyl, trifluoromethyl, methoxy, ethoxy, phenyloxy, pyridyloxy, naphthyloxy, carboxy, a carboxylic acid alkyl ester having an alkyl ester radical selected from the group consisting of C.sub.1 -.sub.6 alkyl or alkoxyalkyl, phenyl and benzyl;
- unsubstituted or substituted carbamyl or sulfamyl wherein the substituent radicals are selected from the group consisting of NH.sub.2, NHCH.sub.3, NHC.sub.2 H.sub.5, NHC.sub.3 H.sub.7, NHC.sub.4 H.sub.9, ##STR350## NHCH.sub.2 C.sub.6 H.sub.5, NHC.sub.6 H.sub.4 Cl, NHC.sub.6 H.sub.3 Cl.sub.2, NHC.sub.6 H.sub.2 Cl.sub.3, NHC.sub.6 H.sub.4 Br, NHC.sub.6 H.sub.4 OCH.sub.3, NHC.sub.6 H.sub.4 OC.sub.2 H.sub.5, NHC.sub.6 H.sub.3 ClOCH.sub.3, NHC.sub.6 H.sub.4 NHCOCH.sub.3, NHC.sub.6 H.sub.4 NHCOC.sub.6 H.sub.5, NHNHCOC.sub.6 H.sub.5, NHNHCOC.sub.6 H.sub.4 Cl, NHNHCOC.sub.6 H.sub.4 CH.sub.3, NHC.sub.6 H.sub.3 ClCH.sub.3, NHC.sub.6 H.sub.2 Cl.sub.2 OCH.sub.3 and NHC.sub.6 H.sub.2 Cl.sub.2 CH.sub.3 ;
- a sulfonic acid aryl ester group, arylsulfonyl, cyano, acylamino selected from the group consisting of NHCOCH.sub.3, NHCOC.sub.2 H.sub.5, NHCOC.sub.3 H.sub.7, NHCOC.sub.6 H.sub.5, NHCOC.sub.6 H.sub.4 Cl, NHCOC.sub.6 H.sub.3 Cl.sub.2, NHCOC.sub.6 H.sub.4 Br, NHCOC.sub.6 H.sub.4 OCH.sub.3, NHCOC.sub.10 H.sub.7, NHCONH.sub.2, NHCONHC.sub.6 H.sub.5, ##STR351## or R.sup.1 is phenyl;
- R.sup.2 is hydrogen, chlorine or bromine;
- R.sup.3 and R.sup.4 are hydrogen, chlorine or bromine;
- and
- X is methyl, a carboxylic acid alkyl ester having an alkyl ester radical selected from the group consisting of C.sub.1 -C.sub.6 alkyl or alkoxyalkyl, phenyl, and benzyl;
- or X is phenyl, naphthyl or pyridyl which is unsubstituted or substituted by chlorine, bromine, nitro, methyl, methoxy or ethoxy;
- or X is acylamino selected from the group consisting of NHCOCH.sub.3, NHOCOC.sub.2 H.sub.5, NHCOC.sub.3 H.sub.7, NHCOC.sub.6 H.sub.5, NHCOC.sub.6 H.sub.4 Cl, NHCOC.sub.6 H.sub.3 Cl.sub.2, NHCOC.sub.6 H.sub.4 Br, NHCOC.sub.6 H.sub.4 OCH.sub.3, NHCOC.sub.10 H.sub.7, NHCONH.sub.2, NHCONHC.sub.6 H.sub.5, ##STR352##
33 more elements
Dependencies are inferred from the claim text.