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US 7,371,831 B2Granted
Azo dyestuffs
AssigneeClariant Finance (BVI) Limited
InventorsMartin Oberholzer, Jürgen Geiwiz
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I) wherein all substituents have the meanings as defined in the Specification, their production and their use.
Claims27
A compound of formula (I)
- wherein
- each A is independently —NH— or —O—,
- B is
- —[—(CH2)1-4—O—(CH2)1-4]4C or
- [—(CH2)1-3—O—(CH2)1-3—O—(CH2)1-3]4C or
- [—(CH2)1-2—O—(CH2)1-2—O—(CH2)1-2—O—(CH2)1-2]4C or
- [(—CH2)1-4]2N(CH2)1-4N[(—CH2)1-4]2
- n′ and n″ are natural numbers and the sum of n′ and n″ is ≧2,
- m is a natural number ≧0,
- CC is a moiety of formula (a)
- wherein
- R1 is H;
- C1-4alkyl;
- C1-4alkyl monosubstituted by hydroxy, halogen, cyano or C1-4alkoxy,
- X1 and X2 independently of each other are halogen;
- an aliphatic, cycloahphatic, aromatic or heterocyclic amino group, said amino group comprising a protonatable nitrogen atom or a quaternary ammonium group, and being an aliphatic, cycloaliphatic, aromatic or heterocyclic mono(C1-4alkyl)-amino group, the C1-4alkyl-group being unsubstituted or monosubstituted by halogen, C1-4alkoxy, C1-4alkyl, phenyl or hydroxy;
- an aliphatic, cycloaliphatic, aromatic or heterocyclic di(C1-4alkyl)-amino group, the C1-4alkyl-groups being independently unsubstituted or monosubstituted by halogen, C1-4alkyl, C1-4alkoxy, phenyl or hydroxy;
- a C5-6cycloalkylamino group, the cycloalkyl group being unsubstituted or substituted by one or two C1-2alkyl groups;
- a phenylamino group, the phenyl ring being unsubstituted or substituted by one or two groups selected from halogen, C1-4alkyl, C1-4alkoxy, hydroxy and phenoxy;
- or a 5- or 6-membered ring containing one or two hetero atoms, in addition to N, O or S, which heterocyclic ring is unsubstituted or substituted by one or two C1-4alkyl groups;
- or a group Z, where Z is independently selected from the group consisting of:
- wherein
- p is 0 or an integer 1, 2 or 3,
- each R9 is independently hydrogen;
- unsubstituted C1-4alkyl or C1-4alkyl monosubstituted by hydroxy, halogen, cyano or C1-4alkoxy,
- each R2 and R3 is independently hydrogen;
- unsubstituted C1-6alkyl;
- C2-6alkyl monosubstituted by hydroxy, amino or cyano;
- phenyl or phenyl-C1-4alkyl, where the phenyl ring of the latter two groups is unsubstituted or substituted by one to three groups selected from chlorine, C1-4alkyl, C1-4alkoxy, unsubstituted C5-6cycloalkyl or C5-6cycloalkyl substituted by one to three C1-4alkyd groups or a pyridinium ring, or
- R2 and R3 together with the nitrogen atom to which they are attached, form a 5- or 6-membered ring containing one to three hetero atoms (in addition to N, one or two further N, O or S), which heterocyclic ring is unsubstituted or substituted by one or two C1-4alkyl groups,
- each R4 and R5 has independently one of significances of R2 and R3, except hydrogen,
- R6 is C1-4alkyd or benzyl with the exception that R6 is not benzyl when R4 and R5 have one of the cyclic significations of R2 and R3, or
- R4, R5 and R6 together with the nitrogen atom to which they are attached, form a pyridinium ring which is unsubstituted or substituted by one or two methyl groups,
- Q1 is C2-8alkylene;
- C3-6alkylene substituted by one or two hydroxy groups;
- C1-6alkylene-1,3- or 1,4-phenylene, or —*NHCOCH2, where * denotes the atom bound to —NR9,
- Q2 is C2-8alkylene;
- C3-6alkylene substituted by one or two hydroxy groups;
- C1-6alkylene-1,3- or -1,4-phenylene or 1,3- or 1,4-phenylene,
- Q3 is C2-8alkylene,
- R7 is hydrogen;
- unsubstituted C1-6alkyl or C1-6alkyl monosubstituted by hydroxy, cyano, chlorine or phenyl,
- R8 is unsubstituted C1-6alkyl or C1-6alkyl monosubstituted by hydroxy, cyano or chlorine, and Anθ is a non-chromophoric anion,
- Y is direct bond, —CO— or —CO—NH—*, wherein the asterisk signifies the bond to the benzene ring and
- o is 0 or 1 or
- CC is a moiety of formula (b)
- wherein
- D is a basic group —NR1-Q4-NR2R3 or a cationic group —NR1-Q4-N+R4R5R6, in which R1, R2, R3, R4, R5 and R6 have the same meanings as above and
- Q4 is C2-6alkylene, which may be interrupted by —O—, —S— or —N(R1)—;
- C2-3alkylene substituted by one or two hydroxy groups;
- or —*NHCOCH2—, where * denotes the atom bound to the —NR1-radical,
- or CC is a moiety of formula (c1) or (c2)
- wherein
- each R10 independently of each other is H;
- C1-4alkyl;
- C5-6cycloalkyl;
- phenyl, benzyl or phenylethyl,
- each R10′ independently of each other is H;
- —OH or C1-4alkyl
- each T1 independently of each other is H;
- —CN;
- —COOR15;
- CONR16R17;
- SO2NR16R17;
- G is H;
- —R11NHR12 or —R11NR13R14, wherein
- R11 is C1-6alkylene or C2-6alkenylene,
- R12 and R13 independently of each other are H;
- unsubstituted C1-6alkyl;
- C2-6alkyl substituted by OH, CN or halogen;
- phenyl-C1-3 alkyl, wherein the phenyl radical is optionally substituted from 1 to 3 times, by a substituent selected from the group consisting of;
- chlorine, C1-4alkyl or C1-4alkoxy;
- unsubstituted C5-6cycloalkyl and C5-6cycloalkyl substituted from 1 to 3 times by C1-4alkyl groups,
- R14 is any of the meanings of R12 or R13 or hydrogen,
- R15 is a C1-6alkyl radical or phenyl-C1-3alkyl radical,
- R16 and R17 independently of each other are H or a C1-4alkyl radical,
- R18 independently of each other signifies H;
- a C1-4alkyl radical;
- —NR16R17—(CH2)2-4—NR16R17 or —CONR16R17,
- R19 is a C1-4alkyl radical or a hydroxy-C1-4alkyl radical,
- R20 is —S— or —O—,
- R21 is hydrogen or a C1-4alkyl radical and
- An− is a non-chromophoric anion,
- with the provisos that
- (i) the sum of n′, n″ and m is smaller as or equal to the valencies of B,
- (ii) when the sum of n′ and n″=2 then m is ≧1,
- (iii) when the sum of n′ and n″=3 and A=NH then m is ≧1
- and their salts and mixtures thereof.
85 more elements
A compound according to formula (II)
- wherein
- B is
- —[—(CH2)1-4—O—(CH2)1-4]4C or
- [—(CH2)1-3—O—CH2)1-3—O—(CH2)1-3]4C or
- [—(CH2)1-2—O—(CH2)1-2—O—(CH2)1-2—O—(CH2)1-2]4C or
- [(—CH2)1-4]2N(CH2)1-4N[(—CH2)1-4]2
- A is independently —NH— or —O—
- m and n are natural numbers
- with the provisos that
- (i) the sum of n and m is smaller as or equal to the valencies of B,
- (ii) when n=2 then m is ≧1,
- (iii) when n=3 and A=NH then m is ≧1,
- and their salts and/or mixtures thereof.
10 more elements
A compound of formula (Ia)
- wherein
- CC is a moiety of formula (a1) or (c2),
- wherein
- R10 is H;
- —CH3 or —CH2CH3,
- T1 is H;
- —CN;
- —CONH2;
- —CONHCH3;
- R10′ is H;
- —CH3 or —OH,
- G is H or —(CH2)2-4NR13R14,
- wherein R13 and R14 are independently from each other H;
- —CH3 or —CH2CH3, or
- wherein
- each R1 is independently from each other H;
- —CH3, —CH2CH3 or substituted C1-4alkyl,
- X1 and X2 are independently from each other halogen or —NR2R3
- wherein R2 and R3 are independently from each other H;
- C1-4alkyl;
- —C2-4alkylene-NH2— or —C2-4alkylene-OH—,
- Y is a direct bond;
- wherein the asterisk is the bond to the benzene ring and
- o is 0 or 1
- n″ is 1, 2, 3 or 4, with the provisos that
- when n″ is 1 then B″ is C(CH2OH)3
- when n″ is 2 then B″ is C(CH2OH)2
- when n″ is 3 then B″ is C(CH2OH)
- when n″ is 4 then B″ is
- C;
- [—(CH2)1-4—O—(CH2)1-4]4C;
- [—(CH2)1-3—O—(CH2)1-3—O—(CH2)1-3]4C;
- [—(CH2)1-2—O—(CH2)1-2—O—(CH2)1-2—O—(CH2)1-2]4C or [(—CH2)1-4]2N(CH2)1-4N[(—CH2)1-4]2.
30 more elements
Dependencies are inferred from the claim text.