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US 4,309,221 AGranted
Anthraquinone derivatives
AssigneeBayer Aktiengesellschaft
InventorsRutger Neeff, Meinhard Rolf, Walter Muller
Life of this patent
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Abstract
Anthraquinone derivatives of the formula ##STR1## or of the tautomeric formula ##STR2## in which A denotes an anthraquinone radical which is free from sulphonic acid groups and is optionally further substituted and which preferably consists of at most 5 fused rings, m denotes an integer, preferably 1 or 2, and R.sub.1 denotes a hydroxyl group or a radical of the formula ##STR3## wherein R.sub.2 represents a substituent and n represents 0, 1, 2, 3 or 4, processes for their preparation, their use for pigmenting organic macromolecular substances and the material pigmented in this manner.
Claims10
An anthraquinone pigment of the formula ##STR80## wherein R.sub.1 denotes a hydroxyl group or a radical of the formula ##STR81## wherein R.sub.2 represents halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, unsubstituted carbamoyl, carbamoyl substituted by a member selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, phenyl which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro and benzyl, unsubstituted sulphamoyl, sulphamoyl substituted by a member selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, phenyl which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro and benzyl, acylamino, arylamino, C.sub.1 -C.sub.4 -alkylsulphonylamino, phenylsulphonylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, unsubstituted benzylsulphonylamino or benzylsulphonylamino or benzylsulphonylamino substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, and
- n represents 0, 1, 2, 3, or 4,
- m.sub.1 represents an integer between 1 and 4,
- R.sub.3 denotes hydrogen, halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -alkylamino, benzylamino, cyclohexylamino, C.sub.1 -C.sub.4 -alkylmercapto, phenylmercapto which is optionally substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine, bromine, or nitro, C.sub.1 -C.sub.4 alkyl carbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, phenylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine or nitro, carbamoyl which is optionally monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, benzyl or phenyl, it being possible for phenyl to be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, carboxyl, hydroxyl, C.sub.1 -C.sub.4 -alkylcarbonylamino, benzoylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine, or nitro, C.sub.1 -C.sub.4 -alkylsulphonylamine or phenylsulphonylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro,
- R.sub.4 denotes hydrogen, chlorine or hydroxyl,
- R.sub.5 denotes hydrogen, halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylmercapto, phenylmercapto which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine, or nitro, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyl, benzylamino, cyclohexylamino, phenylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine or nitro, carboxyl, hydroxyl, carbamoyl which is optionally monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, benzyl or phenyl, it being possible for phenyl to be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkyl, carbonylamino, benzoylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 alkoxy, chlorine, bromine, or nitro, C.sub.1 -C.sub.4 alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro and
- R.sub.6 denotes hydrogen, halogen, or hydroxyl.
3 more elements
Anthraquinone pigments of the formula ##STR82## wherein R.sub.1 denotes a hydroxyl group or a radical of the formula ##STR83## wherein R.sub.2 represents a substituent and
- n represents 0, 1, 2, 3, or 4, and
- R.sub.7, R.sub.8, R.sub.9 and R.sub.10 designate hydrogen, chlorine, bromine, carboxyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, carbamoyl, C.sub.1 -C.sub.4 -alkylcarbonylamino, benzoylamino which is optionally substituted by 1 or 2 nitro groups or 1 to 5 chlorine or bromine atoms, C.sub.1 -C.sub.4 -alkylsulphonylamino, phenylsulphonylamino which is optionally substituted by methyl, methoxy or chlorine or a radical of the formula ##STR84## in which R.sub.1 has the meaning indicated above.
A process for the preparation of an anthraquinone derivative which comprises condensing an aminoanthraquinone of the formula
- A--NH.sub.2).sub.m
- in which
- A represents the radical ##STR85## wherein R.sub.3 denotes hydrogen, halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino, benzylamino, cyclohexylamino, C.sub.1 -C.sub.4 -alkylmercapto, phenylmercapto which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxya, fluorine, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine or nitro, carbamoyl which is optionally monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, benzyl or phenyl optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, carboxyl, hydroxyl, C.sub.1 -C.sub.4 -alkylcarbonylamino, benzoylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro,
- R.sub.4 denotes hydrogen, chlorine or hydroxyl,
- R.sub.5 denotes hydrogen, halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylmercapto, phenylmercapto which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkoxy carbonyl, C.sub.1 -C.sub.4 -alkylcarbonyl, benzylamino, cyclohexylamino, phenylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine, or nitro, carboxyl, hydroxyl, carbamoyl which is optionally monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, benzyl or phenyl, it being possible for m to be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkyl, carbonylamino, benzoylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine, or nitro,
- R.sub.6 denotes hydrogen, halogen, or hydroxyl,
- m denotes an integer with 4-alkoxymethylene-3-oxy-3,4-dihydro-2-naphthoic acid or 4-alkoxy methylene-3-oxy-3,4-dihydro-2-naphthoic acid arylides of the formula ##STR86## wherein R represents a C.sub.1 -C.sub.4 -alkyl group and
- R.sub.1 denotes a hydroxyl group or a radical of the formula ##STR87## wherein R.sub.2 represents a substituent and
- n represents 0, 1, 2, 3, or 4,
- in an organic reaction medium at 100.degree.-220.degree. C.
7 more elements
A process for the preparation of an anthraquinone derivative which comprises condensing a formiminoester of an amino-anthraquinone of the formula
- A--N.dbd.CH--OR).sub.m
- wherein
- A is represented by the formula ##STR88## wherein R.sub.3 denotes hydrogen, halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino, benzylamino, cyclohexylamino, C.sub.1 -C.sub.4 -alkylmercapto, phenylmercapto which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, or nitro, carbamoyl which is optionally monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, benzyl or phenyl, it being possible for phenyl to be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, carboxyl, hydroxyl, C.sub.1 -C.sub.4 -alkylcarbonylamino, benzoylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro,
- R.sub.4 denotes hydrogen, chlorine or hydroxyl,
- R.sub.5 denotes hydrogen, halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylmercapto, phenylmercapto which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkoxy carbonyl, C.sub.1 -C.sub.4 -alkylcarbonyl, benzylamino, cyclohexylamino, phenylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine or nitro, carboxyl, hydroxyl, carbamoyl which is optionally monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, benzyl or phenyl, it being possible for m to be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkyl, carbonylamino, benzoylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine, or nitro,
- R.sub.6 denotes hydrogen, halogen, or hydroxyl,
- m=an integer,
- R denotes a C.sub.1 -C.sub.4 alkyl group,
- with a 3-hydroxy-2-naphthoic acid or 3-hydroxy-2-nitrophthoic acid arylide of the formula ##STR89## wherein R.sub.1 denotes a hydroxyl group or radical of the formula ##STR90## wherein R.sub.2 represents a substituent and
- n represents 0, 1, 2, 3, or 4,
- in an organic reaction medium at 100.degree.-220.degree. C.
8 more elements
A process for the preparation of an anthraquinone pigment which comprises condensing a formimidine of an aminoanthraquinone of the formula
- A--N.dbd.CH--N(R).sub.2 ].sub.m
- wherein
- A denotes an anthraquinone moiety of the formula ##STR91## wherein R.sub.3 denotes hydrogen, halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino, benzylamino, cyclohexylamino, C.sub.1 -C.sub.4 -alkylmercapto, phenylmercapto which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine or nitro, carbamoyl which is optionally monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, benzyl or phenyl, it being possible for phenyl to be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, carboxyl, hydroxyl, C.sub.1 -C.sub.4 -alkylcarbonylamino, benzoylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro,
- R.sub.4 denotes hydrogen, chlorine or hydroxyl,
- R.sub.5 denotes hydrogen, halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylmercapto, phenylmercapto which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkoxy carbonyl, C.sub.1 -C.sub.4 -alkylcarbonyl, benzylamino, cyclohexylamino, phenylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine or nitro, carboxyl, hydroxyl, carbamoyl which is optionally monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, benzyl or phenyl, it being possible for m to be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkyl, carbonylamino, benzoylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine or nitro, C.sub.1 -C.sub.4 -alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, fluorine, chlorine, bromine, or nitro,
- R.sub.6 denotes hydrogen, halogen, or hydroxyl,
- m is an integer and
- R is an C.sub.1 -C.sub.4 alkyl group
- with 3-hydroxy-2-naphthoic acid or a 3-hydroxy-2-naphthoic acid arylide of the formula ##STR92## wherein R.sub.1 denotes a hydroxyl group or a radical of the formula ##STR93## wherein R.sub.2 represents a substituent and
- n represents 0, 1, 2, 3, or 4,
- in an organic reaction medium at 100.degree.-220.degree. C.
8 more elements
Dependencies are inferred from the claim text.