Patent ID: 6626990
Filing Date: 2003-09-30
Classification: C09B

Abstract:
A process for producing a quinacridone pigment according to formula B or a solid solution thereof,comprising oxidizing a salt of a corresponding 6,13-dihydroquinacridone of formula A or a mixture of two or more 6,13-dihydroquinacridones of formula A â€ƒin which X and Y are independently 1 or 2 substituents selected from the group consisting of H, F, Cl, C1-C4 alkyl and C1-C4 alkoxy, in the presence of at least one (hetero)aromatic hydroxyl containing compound that does not contain a pigment moiety and an oxidizing agents, wherein the (hetero)aromatic hydroxyl-containing compound is a compound of formula I whereink is 1 or 2 andwhen k=1, G is hydrogen or â€”OR25 E1 and E2 in dependently of one another, are a group of the formula Ia or Ib whereinâ€ƒR25 is hydrogen; C1-C18alkyl; C1-C18alkyl which is substituted by OH, halogen, â€”COOH, â€”COOR29, â€”CONH2, â€”CONHR30, â€”CON(R30)(R31), â€”NH2, NHR30, â€”N(R30)(R31), â€”NHCOR32, â€”CN, COR32, â€”OCOR32, phenoxy and/or C1-C18alkyl-, C1-C18alkoxy- or halo-substituted phenoxy; C3-C50alkyl which is interrupted by â€”Oâ€” and can be substituted by OH; C3-C6alkenyl; glycidyl; C5-C12cycloalkyl; C5-C12cycloalkyl substituted by OH, C1-C4alkyl or â€”OCOR32; C7-C11phenylalkyl which is unsubstituted or substituted by OH, Cl, C1-C18alkoxy or C1-C18alkyl; â€”COR32 or â€”SO2â€”R33; or a radical of one of the formulae whereinâ€ƒT is hydrogen; C1-C8alkyl; C2-C8alkyl which is substituted by one or more hydroxyl groups or by one or more acyloxy groups; oxyl; hydroxyl; â€”CH2CN; C1-C18alkoxy; C5-C12cycloalkoxy; C3-C6alkenyl; C7-C9phenylalkyl; C7-C9phenylalkyl which is substituted once, twice or three times in the phenyl ring by C1-C4alkyl; or is aliphatic C1-C8alkanoyl; R24 is hydrogen; C1-C24alkyl or C5-C12cycloalkyl; or is C1-C24alkyl or C5-C12cycloalkyl which is substituted by 1 to 9 halogen atoms, OH, OR25, halogen, â€”COOH, â€”COOR29, â€”CONH2, â€”CONHR30, â€”CON(R30)(R31), â€”NH2, NHR30, â€”N(R30)(R31), â€”NHCOR32, â€”CN, COR32, â€”OCOR32, â€”CN, â€”NO2, â€”SR32, â€”SOR32, â€”SO2R32, â€”P(O)(OR25)2, a morpholinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, piperazinyl or N-methylpiperazinyl group or by combinations thereof; or is C5-C12cycloalkyl or C1-C24alkyl which is interrupted by 1 to 6 phenylene, â€”Oâ€”, â€”NR29â€”, â€”CONR29â€”, â€”COOâ€”, â€”OCOâ€”, â€”CH(R33)â€”, â€”C(R33)2â€” or â€”COâ€” groups or combinations thereof; or R24 is C2-C24alkenyl; halogen; â€”SR32, SOR32; SO2R32; â€”SO3H; or SO3M; R26, R27 and R28, independently of one another, are H, C1-C12alkyl; C2-C6alkenyl; C1-C18alkoxy; C5-C12cycloalkoxy; C2-C18alkenoxy; halogen; â€”Câ‰¡N; C1-C4haloalkyl; C7-C11phenylalkyl; COOR29; CONH2; â€”CONHR30; â€”CON(R30)(R31); sulfo; C2-C18acylamino; OCOR32; phenyloxy; or phenyloxy, which is substituted by C1-C18alkyl, C1-C18alkoxy or halogen; R29 is C1-C18alkyl; C3-C18alkenyl; C3-C50alkyl which is interrupted by O, NH, NR or S and/or is substituted by OH; glycidyl; C5-C12cycloalkyl; C1-C4alkylcyclohexyl; phenyl; C7-C14alkylphenyl; C6-C15bicycloalkyl; C6-C15bicycloalkenyl; C6-C15tricycloalkyl; C6-C14bicycloalkylalkyl; or C7-C11phenylalkyl; R30 and R31, independently of one another are C1-C12alkyl; C3-C12alkoxyalkyl; C2-C18alkanoyl; C4-C16dialkylaminoalkyl or C5-C12cycloalkyl; or R30 and R31 together are C3-C9alkylene or -oxaalkylene or -azaalkylene; R32 is C1-C18alkyl; C1-C12alkoxy; C2-C18alkenyl; C7-C11phenylalkyl; C7-C11phenylalkoxy; C6-C12cycloalkyl; C6-C12cycloalkoxy; phenoxy or phenyl; or is C3-C50alkyl which is interrupted by â€”Oâ€” and can be substituted by OH; R33 is C1-C18alkyl; C2-C18alkenyl; C6-C12cycloalkyl; provided at least one G is an â€”OR25 group; when k=2, E1 and E2 are a group of the formula Ia; G is C2-C16alkylene, C4-C12alkenylene, xylylene, C3-C20alkylene which is interrupted by O and/or substituted by OH, or a group of the formula â€”CH2CH(OH)CH2Oâ€”R34â€”OCH2CH(OH)CH2â€”, â€”COâ€”R35â€”COâ€”, â€”COâ€”NHâ€”R36â€”NHâ€”COâ€”, â€”(CH2)jâ€”COOâ€”G20â€”OOCâ€”(CH2)jâ€”, in which j is a number from the range from 1 to 3, or â€ƒR34 is C2-C10alkylene; C4-C50alkylene which is interrupted by O, phenylene, or a group -phenylene-E-phenylene-, in which E is â€”Oâ€”, â€”Sâ€”, â€”SO2â€”, â€”CH2â€”, â€”COâ€”, or â€”C(CH3)2â€”; R35 is C2-C10alkylene, C2-C10oxaalkylene, C2-C10thiaalkylene, C6-C12arylene or C2-C6alkenylene; R36 is C2-C10alkylene, phenylene, tolylene, diphenylenemethane or a group of the formula â€ƒM is alkali metal.