公开(公告)号：US4390470A

公开(公告)日：1983-06-28

申请号：US39254

申请日：1979-05-16

Applicant: Heinz Wicki ,  Claude Vogel

Inventor： Heinz Wicki ,  Claude Vogel

IPC: C09B35/46 ,  C09B35/52 ,  C09B35/60 ,  C09B31/30 ,  C09B33/18

CPC classification number: C09B35/52 ,  C09B35/46 ,  C09B35/60 ,  C09B56/04

Abstract: Disclosed are compounds of the formula, ##STR1## wherein the X's are the same and are hydrogen or --SO.sub.3 M,Y is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxy, halogen, --COOM or --SO.sub.3 M,K.sub.1 and K.sub.2 are the same or different and are both radicals of a coupling component,either A.sub.1 is --SO.sub.3 M and one of B.sub.1 and C.sub.1 is --SO.sub.3 M, the other being hydrogen,or A.sub.1 and C.sub.1 are both hydrogen and B.sub.1 is --SO.sub.3 M, andM is hydrogen or a non-chromophoric cation, their production and use in dyeing anionic dyeable substrates, for example, natural and regenerated cellulose, natural and synthetic polyamides, polyurethanes, polypropylene modified to contain basic groups, anodized aluminum, paper and, particularly, leather.

Abstract translation: 公开了下式的化合物，其中X是相同的并且是氢或-SO 3 M，Y是氢，C 1-4烷基，C 1-4烷氧基，羟基，卤素，-COOM或-SO 3 M， K1和K2相同或不同，均为偶联成分的自由基，A1为-SO3M，B1和C1之一为-SO3M，另一个为氢，或A1和C1均为氢，B1为-SO3M， 并且M是氢或非发色阳离子，它们在染色阴离子可染色基质中的生产和用途，例如天然和再生纤维素，天然和合成聚酰胺，聚氨酯，改性成含有碱性基团的聚丙烯，阳极氧化铝，纸，特别是 ，皮革。

公开(公告)号：US4374064A

公开(公告)日：1983-02-15

申请号：US144380

申请日：1980-04-28

Applicant: Heinz Wicki

Inventor： Heinz Wicki

IPC: C09B31/02 ,  C09B45/24 ,  D06P3/32 ,  C09B45/26 ,  C09B45/28 ,  C09B45/30 ,  C09B45/32

CPC classification number: C09B31/025 ,  C09B45/24 ,  D06P3/3213 ,  D06P3/326 ,  Y10T428/23943

Abstract: Compounds of the formula ##STR1## in which A--X-- is the radical of a diazo component,X-- is ortho to the azo group and is a metallizable substituent or a substituent convertible to a metallizable group,Y is --OH or --NH.sub.2,Z is methyl or carboxy,R is hydrogen, halogen, methyl or sulpho,andB is the radical of a coupling component of the heterocyclic, acyclic active methylene or monocyclic benzene series, which coupling component of the monocyclic benzene series contains an amino and/or hydroxy group which groups may be alkylated or acylated, and--N.dbd.N--B is bound to the 3- or 4-position of ring D,which compounds contain at least one water-solubilizing group,and metal complexes thereof, with the proviso that when the compounds are unmetallized, B is other than amonocyclic benzene coupling component radical. The metal complexes are useful as dyes for the dyeing and printing of anionic dyeable.

Abstract translation: 其中AX-是重氮组分基团的式“IMAGE”的化合物，X-是偶氮基团的邻位，并且是可金属化的取代基或可转化为可金属化基团的取代基，Y是-OH或-NH 2，Z 是甲基或羧基，R是氢，卤素，甲基或磺基，B是杂环，无环活性亚甲基或单环苯系的偶联组分的基团，单环苯系的偶联组分含有氨基和/或 可以将这些基团烷基化或酰化的羟基和-N = NB与环D的3-或4-位结合，该化合物含有至少一个水溶性基团及其金属络合物，条件是当 该化合物未金属化，B不是单环苯偶合成分基团。 金属络合物可用作染色和印染阴离子可染色染料。

公开(公告)号：US4150942A

公开(公告)日：1979-04-24

申请号：US801397

申请日：1977-05-27

Applicant: Herbert Holliger ,  Heinz Wicki

Inventor： Herbert Holliger ,  Heinz Wicki

IPC: C09B45/24 ,  D06P3/32 ,  C09B45/26 ,  C09B45/30 ,  C09B45/32

CPC classification number: C09B45/24 ,  D06P3/326

Abstract: 1:2 Metal complexes of the formula ##STR1## in which EACH A is, independently, a 1,2-phenylene or 1,2-naphthylene diazo component radical which is unsubstituted or substituted by up to two substituents selected from (C.sub.1-4)alkyl, (C.sub.1-4)alkoxy, halogen, nitro, sulpho and carboxy,Q is a group of the formula --N.dbd.N--B or --NHR.sub.3,each B is, independently, a coupling component radical of the aliphatic series containing an enolic hydroxy group, a coupling component radical of the naphthol series free of amino groups or a coupling component,Each X is, independently, --O-- or --COO--, radical of the benzene series having at least one phenolic hydroxy group and/or a group of the formula --NR.sub.1 R.sub.2, with the proviso that when Q is --NHR.sub.3, B is a radical of the benzene series,R.sub.1 is hydrogen, (C.sub.1-6)alkyl or (C.sub.2-4)hydroxyalkyl,R.sub.2 is hydrogen, (C.sub.1-6)alkyl, phenyl, (C.sub.1-6)alkylphenyl or (C.sub.2-4)hydroxyalkyl,R.sub.3 is R'-CO-, wherein R' is hydrogen or alkyl,M is a 1:2 metal complex forming metal, andY.sup..sym. is hydrogen or an equivalent of a non-chromophoric cation,And mixtures thereof,Which complexes are in free acid or salt form and are useful as dyestuffs for dyeing substrates dyeable with anionic dyes, e.g., natural and regenerated cellulose, paper, polyurethanes, high molecular weight polymers such as polypropylene modified to contain basic groups, natural and synthetic polyamides, anodized aluminum and, particularly, leather.

Abstract translation: 1：2式“IMAGE”的金属络合物，其中每个A独立地是未被取代或被至多两个选自（C 1-4）的取代基取代的1,2-亚苯基或1,2-亚萘基重氮组分基团） ）烷基，（C 1-4）烷氧基，卤素，硝基，磺基和羧基，Q是式-N = NB或-NHR 3的基团，每个B独立地是含有烯烃的脂族系列的偶联组分基团 羟基，不含氨基的萘酚系的偶联组分基团或偶合组分，每个X独立地是-O-或-COO-，具有至少一个酚羟基的苯系自由基和/或 式-NR1R2的基团，条件是当Q为-NHR3时，B为苯系的基团，R1为氢，（C1-6）烷基或（C2-4）羟烷基，R2为氢，（C1 -6）烷基，苯基，（C 1-6）烷基苯基或（C 2-4）羟基烷基，R 3是R'-CO-，其中R'是氢或烷基，M是形成金属的1:2金属络合物，Y （+）是氢 或等同的非发色阳离子及其混合物，其复合物为无级酸或盐形式，并且可用作用于染色可与阴离子染料，EG，天然和再生纤维素，纸，聚氨酯，高分子量重叠的底物的试剂 聚合物如聚丙烯改性成基本组合，天然和合成聚酰胺，阳极氧化铝，特别是皮革。

公开(公告)号：US4120854A

公开(公告)日：1978-10-17

申请号：US726979

申请日：1976-09-27

Applicant: Heinz Wicki

Inventor： Heinz Wicki

IPC: C09B33/02 ,  C09B33/24 ,  C09B45/24 ,  C09B33/20 ,  C09B45/34

CPC classification number: C09B33/02 ,  C09B33/24 ,  C09B45/24

Abstract: Compounds of the formula ##STR1## in which R.sub.1 is hydrogen or nitro,Each of R.sub.2 and R.sub.3, independently, is --OH or --NH.sub.2,R.sub.4 is hydrogen, nitro or (C.sub.1-4) alkyl,R.sub.5 is hydrogen, nitro or (C.sub.1-4) alkoxy,R.sub.6 is hydrogen, (C.sub.1-4) alkyl, (C.sub.1-4) alkoxy, --COOM or --SO.sub.3 M,R.sub.7 is hydrogen or --SO.sub.3 M,R.sub.8 is hydrogen or the radical of a diazo component, andM is a hydrogen ion or a non-chromophoric cation,And mixtures thereof, in metallized form or unmetallized form, which compounds in metallized form are useful as dyes for paper and leather. The dyeings exhibit notable fastness to light, hard water, washing, perspiration, alkali, acid and buffing.

Abstract translation: 其中R 1是氢或硝基，每个R 2和R 3独立地是-OH或-NH 2，R 4是氢，硝基或（C 1-4）烷基，R 5是氢，硝基或（ C 1-4烷氧基，R 6是氢，（C 1-4）烷基，（C 1-4）烷氧基，-COOM或-SO 3 M，R 7是氢或-SO 3 M，R 8是氢或重氮组分的基团，M 是氢离子或非发色阳离子，以及其金属化形式或非成形形式的混合物，金属化形式的化合物作为纸和皮革的染料有用。 染色表现出明显的耐光牢度，硬水，洗涤，出汗，碱，酸和抛光。

公开(公告)号：US4649194A

公开(公告)日：1987-03-10

申请号：US517766

申请日：1983-07-27

Applicant: Heinz Wicki

Inventor： Heinz Wicki

IPC: C09B31/02 ,  C09B45/24 ,  C09B45/00 ,  C09B45/06 ,  C09B45/26 ,  D06P3/32

CPC classification number: C09B31/025 ,  C09B45/24

Abstract: 1:2 Metal complexes of the formula ##STR1## wherein X.sub.1 is --O-- or ##STR2## and X.sub.2 is --O-- or ##STR3## the starred atom being attached A.sub.1 or A.sub.2, respectively, A.sub.1 is a diazo component radical of the benzene series,A.sub.2 is a diazo component radical of the benzene or naphthalene series,W is --CH.sub.3 or --COOH,R is hydrogen or --SO.sub.3 H,each of B.sub.1 and B.sub.2 is independently a coupling component radical or a phenolic hydroxy group-containing coupling component radical at least one phenolic hydroxy group of which is etherified or acylated,M is iron, cobalt or chromium, andn is 1 or 2,which complexes are useful as anionic dyestuffs having olive to brown colors for substrates such as natural and regenerated cellulose, natural and synthetic polyamides, polyurethane and anodized aluminum, especially leather.

Abstract translation: 1：2具有式（IMAGE）的金属络合物，其中X1为-O-或，X2为-O-或分别连接有A1或A2的星形原子，A1为 苯系，A2是苯或萘系的重氮组分基团，W是-CH 3或-COOH，R是氢或-SO 3 H，B1和B2各自独立地是偶联组分基团或含酚羟基的偶联 组分基团其至少一个酚羟基被醚化或酰化，M是铁，钴或铬，n是1或2，该配合物可用作具有橄榄色至棕色的阴离子染料，用于底物如天然和再生纤维素 ，天然和合成聚酰胺，聚氨酯和阳极氧化铝，特别是皮革。

公开(公告)号：US4409142A

公开(公告)日：1983-10-11

申请号：US253684

申请日：1981-04-13

Applicant: Heinz Wicki

Inventor： Heinz Wicki

IPC: C09B31/02 ,  C09B45/24 ,  D06P3/32 ,  C09B31/06 ,  C09B31/10 ,  C09B31/14

CPC classification number: C09B31/025 ,  C09B45/24 ,  D06P3/3213 ,  D06P3/326 ,  Y10T428/23943

Abstract: Compounds of the formula ##STR1## in which A-X- is the radical of a diazo component,X- is ortho to the azo group and is a metallizable substituent or a substituent convertible to a metallizable group,Y is --OH or --NH.sub.2,Z is methyl or carboxy,R is hydrogen, halo, methyl or sulfo, andB is the radical of a coupling component of the heterocyclic, non-cyclic active methylene or monocyclic benzene series, which coupling component of the monocyclic benzene series contains an amino and/or hydroxy group, which group(s) may be alkylated or acylated, and --N.dbd.N--B is bound to the 3- or 4-position of ring D, which comounds contain at least one water-solubilizing group, and metal complexes thereof, with the proviso that when the compounds are unmetallized, B is other than a monocyclic benzene coupling component radical. The metal complexes are useful as dyes for the dyeing and printing of anionic dyeable substrates such as natural and regenerated cellulose, natural and synthetic polyamides, polypropylene modified to contain basic groups, polyurethanes, anodized aluminum, sized paper and leather.

Abstract translation: 其中AX-是重氮组分基团的式“IMAGE”的化合物，X-是偶氮基团的邻位，并且是可金属化的取代基或可转化为可金属化基团的取代基，Y是-OH或-NH 2，Z 是甲基或羧基，R是氢，卤素，甲基或磺基，B是杂环，非环状活性亚甲基或单环苯系的偶联成分的基团，单环苯系的偶联成分含有氨基和 /或羟基，该基团可以被烷基化或酰化，并且-N = NB与环D的3-或4-位结合，所述环D含有至少一个水溶性基团，及其金属络合物 ，条件是当化合物未金属化时，B不是单环苯偶联组分基团。 金属络合物可用作染色和印染阴离子可染色基质如天然和再生纤维素，天然和合成聚酰胺，改性成含有碱性基团的聚丙烯，聚氨酯，阳极氧化铝，大小纸和皮革的染料。

公开(公告)号：US4358287A

公开(公告)日：1982-11-09

申请号：US253683

申请日：1981-04-13

Applicant: Heinz Wicki ,  Claude Vogel

Inventor： Heinz Wicki ,  Claude Vogel

IPC: C09B45/24 ,  C09B45/00 ,  C09B45/26

CPC classification number: C09B45/24

Abstract: 1:2 Metal complexes of the formula ##STR1## in which each of X.sub.1 and X.sub.2, independently, is --COO-- or --O--,each of B.sub.1 and B.sub.2, independently, is a radical of a coupling component of the benzene or oxyquinoline series,M is a metal capable of forming a 1:2 complex and,each of ##STR2## independently, is the radical of a diazo component of the benzene series, with the proviso that at most one of such diazo component radicals contains a single sulpho group,and mixtures thereof with one or more of the corresponding symmetrical 1:2 metal complexes,which complexes and mixtures of complexes are in free acid or salt form and are useful as anionic dyes for dyeing and printing substrates such as natural and regenerated cellulose, natural and synthetic polyamides, polyurethanes and polymers modified to contain basic groups, especially leather.

Abstract translation: 1：2式“IMAGE”的金属配合物，其中X1和X2各自独立地为-COO-或-O-，B1和B2各自独立地为苯或羟基喹啉的偶联成分的基团 系列中，M是能够形成1:2络合物的金属，独立地，每个“IMAGE”是苯系的重氮组分的基团，条件是至多一个这样的重氮组分基团包含单个 磺基和它们与一种或多种对应的对称的1:2金属络合物的混合物，其络合物和络合物的混合物为游离酸或盐形式，并且可用作染色和印刷底物如阴离子和再生纤维素的阴离子染料 ，天然和合成聚酰胺，聚氨酯和改性成含有碱性基团的聚合物，特别是皮革。

公开(公告)号：US4169832A

公开(公告)日：1979-10-02

申请号：US885627

申请日：1978-03-13

Applicant: Heinz Wicki ,  Claude Vogel

Inventor： Heinz Wicki ,  Claude Vogel

IPC: C09B35/46 ,  C09B35/52 ,  C09B33/10 ,  C09B33/12 ,  C09B33/16 ,  C09B33/18

CPC classification number: C09B35/46 ,  C09B35/52

Abstract: Disclosed are compounds of the formula, ##STR1## wherein THE X's are the same and are hydrogen or --SO.sub.3 M,Y is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxy, halogen, --COOM or --SO.sub.3 M,K.sub.1 and K.sub.2 are the same or different and are both radicals of a coupling component,Either A.sub.1 is --SO.sub.3 M and one of B.sub.1 and C.sub.1 is --SO.sub.3 M, the other being hydrogen,Or A.sub.1 and C.sub.1 are both hydrogen and B.sub.1 is --SO.sub.3 M, andM is hydrogen or a non-chromophoric cation, their production and use in dyeing anionic dyeable substrates, for example, natural and regenerated cellulose, natural and synthetic polyamides, polyurethanes, polypropylene modified to contain basic groups, anodized aluminum, paper and, particularly, leather. The dyes are well-soluble in water, possess good resistance to acid, have relatively high substantivity especially to paper and leather and give good penetration dyeings with leather.Compounds of the formula ##STR2## wherein Q is --NH.sub.2, --NO.sub.2, acylamino or K.sub.3 --N.dbd.N--,wherein K.sub.3 is a coupling component radical free of diazotizable amino groups,Q is --NH.sub.2, --NO.sub.2, acylamino or --N.dbd.N--K.sub.4,wherein K.sub.4 is a coupling component radical free of diazotizable amino groups, with the proviso that when Q is K.sub.3 --N.dbd.N--, Q' is amino, nitro or acylamino, andA.sub.1, b.sub.1, c.sub.1, each X and Y are as defined above, are useful as intermediates in the synthesis of the polyazo compounds.

Abstract translation: 公开了下式的化合物，其中X是相同的并且是氢或-SO 3 M，Y是氢，C 1-4烷基，C 1-4烷氧基，羟基，卤素，-COOM或-SO

公开(公告)号：US4097476A

公开(公告)日：1978-06-27

申请号：US585663

申请日：1975-06-10

Applicant: Heinz Wicki

Inventor： Heinz Wicki

IPC: C09B35/46 ,  D21H21/28 ,  C09B31/24 ,  D06P1/06 ,  D06P3/32

CPC classification number: C09B35/461

Abstract: Disclosed are compounds of the formula, ##STR1## in which X is hydrogen, chlorine, C.sub.1-4 alkyl or alkoxy, --SO.sub.3 M or --CO.sub.2 M, one of the Y's is hydrogen, the other --SO.sub.3 M, A is a mono- or di-sulphonaphthyl radical which is optionally further substituted, or ##STR2## in which R is hydrogen, hydroxy or C.sub.1-4 alkyl or alkoxy, B is a radical or a coupling component (b.sub.1) to (b.sub.10), ##STR3## WHERE R.sub.1 is --NH.sub.2, anilino or toluidino, R.sub.2 is --NH.sub.2 or --OH, and Either R.sub.3 is hydrogen, or When R.sub.1 and R.sub.2 both are --NH.sub.2, R.sub.3 is hydrogen, --SO.sub.3 M or C.sub.1-4 alkyl; ##STR4## WHERE R.sub.4 is hydrogen or C.sub.1-4 alkyl; ##STR5## WHERE R.sub.5 is hydrogen or --CO.sub.2 M; ##STR6## WHERE ONE OF THE Y.sub.1 's is hydrogen, the other --SO.sub.3 M; ##STR7## WHERE R.sub.6 is phenyl or C.sub.1-4 alkylphenyl; ##STR8## where R.sub.7 is --OH or --NH.sub.2, R.sub.8 is hydrogen, phenyl or sulphophenyl, and R.sub.9 is C.sub.1-4 alkyl or --CO.sub.2 M, and the M's independently, signify hydrogen or a non-chromophoric cation, their production and use for dyeing and printing anionic dyeable substrates, e.g., natural and regenerated cellulose, natural and synthetic polyamides, polyurethanes and basically modified polypropylene and particularly leather, paper and anodized aluminum. The obtained dyeings have shades ranging from deep green or blue to black. The dyeings on paper exhibit notable fastness to water and water-spotting while the dyeings on leather are level and exhibit good fastness to perspiration, dry cleaning, water, water-spotting and buffing and resistance to migration onto polyvinyl chloride.

Abstract translation: 公开了下式的化合物，其中X是氢，氯，C 1-4烷基或烷氧基，-SO 3 M或-CO 2 M，Y之一是氢，另一个-SO 3 M，A是单或二 - 其中R是氢，羟基或C 1-4烷基或烷氧基，B是自由基或偶合组分（b1）至（b10），（b1）其中R 1，R 2， 是-NH 2，苯胺基或甲苯酰基，R 2是-NH 2或-OH，并且R 3是氢，或者当R 1和R 2都是-NH 2，R 3是氢，-SO 3 M或C 1-4烷基时; （b2）R4为氢或C1-4烷基; （b3）R5是氢或-CO 2 M; （b4）（b5）（b6）Y1中的一个是氢，另一个-SO 3 M; （b7）（b8）（b9）R6是苯基或C1-4烷基苯基; （b10）其中R7是-OH或-NH2，R8是氢，苯基或磺基苯基，R9是C1-4烷基或-CO2M，M独立地表示氢或非发色阳离子，它们的生产和 用于染色和印刷阴离子可染色基材，例如天然和再生纤维素，天然和合成聚酰胺，聚氨酯和基本上改性的聚丙烯，特别是皮革，纸和阳极氧化铝。 获得的染色有从深绿色或蓝色到黑色的色调。 纸上的染色表现出显着的耐水牢度和耐水斑性，而皮革上的染色水平，表现出良好的出汗牢度，干洗，水分，水斑和抛光以及耐氯迁移性。

公开(公告)号：US3975369A

公开(公告)日：1976-08-17

申请号：US419509

申请日：1973-11-28

Applicant: Heinz Wicki

Inventor： Heinz Wicki

IPC: C09B45/04 ,  C09B45/24 ,  D06P3/32 ,  C09B45/22 ,  C09B45/32 ,  D06P1/10 ,  D06P3/00

CPC classification number: D06P3/3233 ,  C09B45/04 ,  C09B45/24

Abstract: Dyes of the formula ##SPC1##WhereinEach of R, R.sub.1, R.sub.2 and R.sub.3 is independently hydrogen, halo, nitro, unsubstituted or substituted alkyl or alkoxy, carboxy or sulfo,R.sub.4 is a diazo component radical, and Me is a metal atom,Are useful for dyeing and printing of leather. They exhaust well on leathers of low affinity and give level dyeings. The dyeings exhibit good fastness to light, water, washing, perspiration, ironing and formaldehyde.

Abstract translation: R，R 1，R 2和R 3各自独立地为氢，卤素，硝基，未取代或取代的烷基或烷氧基，羧基或磺基，R 4为重氮组分基团，Me为金属原子，ARE有用的 皮革的染色和印花。 它们在低亲和力的皮革上排气良好，并赋予水平的染色。 染色对光，水，洗涤，出汗，熨烫和甲醛表现出良好的牢度。