公开(公告)号：US4898944A

公开(公告)日：1990-02-06

申请号：US263613

申请日：1988-10-27

Applicant: Gunther Schwaiger ,  Hartmut Springer ,  Walter Helmling

Inventor： Gunther Schwaiger ,  Hartmut Springer ,  Walter Helmling

IPC: C09B19/00 ,  C07C67/00 ,  C07C313/00 ,  C07C317/14 ,  C07C317/22 ,  C07C317/34 ,  C07C317/36 ,  C07C317/46 ,  C07C317/48 ,  C07C323/65 ,  C07D498/04 ,  C09B62/503 ,  D06P1/384 ,  D06P3/10 ,  D06P3/66 ,  C07C147/103 ,  C07C147/107 ,  C07C147/12

CPC classification number: C09B62/5033

Abstract: Precursors for the preparation of fiber-reactive triphendioxazine dyestuffs correspond to the general formulas: ##STR1## in which Y' is a vinyl, a beta-hydroxyethyl or an ethyl group which contains in the beta-position a substituent which can be eliminated by an alkali;T is an optionally substituted alkyl (e.g. substituted with hydroxy) with 1-6 carbon atoms, preferably 1 to 4 carbon atoms, excluding a radical of the group Y' defined above, it also being possible for the alkyl group to be interrupted by hetero groups, preferably 1 to 2 hetero groups, selected from groups of the formulae --O--, --S--, --NH-- and --N(R')--, where R' has the meaning given below, or T is an optionally substituted aryl group;B is an oxygen or sulfur atom or an amino group of the formula --NH-- or --N(R')--, in whichR' is an alkyl group with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, such as, in particular, the methyl or ethyl group, which can be substituted;W is a divalent, optionally substituted aliphatic, optionally alkyl-substituted (C.sub.5 -C.sub.10)-cycloaliphatic, optionally alkyl-substituted aliphatic-(C.sub.5 -C.sub.8)-cycloaliphatic, optionally substituted araliphatic or optionally substituted aromatic-carbocyclic radical or a benzotriazole radical combined with one of these radicals, it being possible for the aliphatic radicals in W to be interrupted by hetero groups, preferably 1 to 2 hetero groups, selected from the groups --O--, --S--, --SO.sub.2 --, --CO--, 1,4-piperidino, --NH-- and --N(R.sup.o)--, in which R.sup.o has one of the meanings of R' or is an alkanoyl group with 2 to 5 carbon atoms, such as an acetyl group, and/or it being possible for aliphatic and aryl radicals to be linked to one another by such a hetero group;R' is a hydrogen atom or alkyl with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, such as, in particular, methyl and ethyl of these, alkoxy with 1 to 5 carbon atoms, preferably 1 to 4 carbon atoms, such as, in particular, methoxy and ethoxy of these, halogen, such as fluorine or bromine or, in particular, chlorine, carboxy or sulfo;n is the number 1 to 2, but is preferably 1.

公开(公告)号：US4885385A

公开(公告)日：1989-12-05

申请号：US225545

申请日：1988-07-28

Applicant: Hartmut Springer ,  Walter Helmling ,  Gunther Schwaiger

Inventor： Hartmut Springer ,  Walter Helmling ,  Gunther Schwaiger

IPC: C09B19/00 ,  C07C67/00 ,  C07C313/00 ,  C07C315/04 ,  C07C317/22 ,  C07C317/36 ,  C07C319/20 ,  C07C323/65 ,  C07D498/04 ,  C09B62/503 ,  D06P1/384 ,  D06P3/66

CPC classification number: C09B62/5033

Abstract: Water-soluble triphendioxazine compounds having fiber-reactive dye properties conforming to the general formula ##STR1## where: B is --O-- or --S-- or --NH-- or (C.sub.1 -C.sub.6)-alkylamino;R* is hydrogen or optionally substituted alkyl or aryl;W and W.sup.1 are each a bivalent, aliphatic or optionally alkyl-substituted cycloaliphatic or aliphatic-cycloaliphatic radical, which aliphatic radicals can be interrupted by --O--, --S--, sulfonyl, carbonyl, 1,4-piperidino, amino, alkylamino and/or alkanoylamino groups, orthe grouping --B--W.sup.1 --N(R*) and/or --N(R*)--W--B-- each represent the bivalent radical of a five- or six-membered saturated heterocycle which contains two nitrogen atoms, orthe grouping --B--W.sup.1 -- and/or --W--B-- each represent the bivalent radical of a five- or six=-membered saturated heterocycle which contains two nitrogen atoms and which is bonded by one of the two nitrogen atoms via an alkylene group of 2 to 4 carbon atoms to the grouping --N(R*)--CO--G.sup.1 -- or --G--CO--A--N(R*);G and G.sup.1 are each a direct bond or a (C.sub.1 -C.sub.8)-alkylene or aliphatic-cycloaliphatic or cycloaliphatic radical;M is hydrogen, alkali metal or alkaline earth metal;X.sup.1 and X.sup.2 are each hydrogen, halogen, alkyl, alkoxy, aryloxy or optionally substituted aryl;Y is vinyl or ethyl having an alkali-eliminable substituent in the .beta.-position,and also precursors thereof, conforming to the general formula ##STR2## where Q is the nitro or amino group, B, R* and M have the above meanings, Y' has a meaning of Y or is equal to .beta.-hydroxyethyl and K has the above meaning of G or, if Q is equal to NO.sub.2, is also equal to alkenylene of 2 to 8 carbon atoms or alkdienylene of 4 to 8 carbon atoms.The triphendioxazine compounds serve as dyes for dyeing carboxamido-containing fiber materials, in particular hydroxyl-containing fiber materials, such as cellulose; they produce strong, fast, blue dyeings.

公开(公告)号：US4808193A

公开(公告)日：1989-02-28

申请号：US198991

申请日：1988-05-26

Applicant: Ludwig Schlafer ,  Hartmut Springer ,  Michael Kunze

Inventor： Ludwig Schlafer ,  Hartmut Springer ,  Michael Kunze

IPC: C09B62/44 ,  D06P1/384 ,  C09B35/02 ,  C09B43/40 ,  C09B62/01 ,  D06P1/38

CPC classification number: C09B62/4415 ,  D06P1/384 ,  Y10S8/918

Abstract: Water-soluble compounds having fiber-reactive dye properties of the general formula ##STR1## in which A is an alkylene of 2 to 6 carbon atoms or a phenylene which can be substituted by 1 or 2 substituents, or is a radical of the formula ##STR2## in which W is a direct bond or a bridge member and the R' and R* each denote hydrogen, chlorine, methyl, methoxy, ethoxy, carboxy or sulfo;B is chlorine or fluorine;R is hydrogen, chlorine, an alkyl of 1 to 4 carbon atoms or an alkoxy of 1 to 4 carbon atoms;M is hydrogen or an alkali metal;n stands for the number zero, 1 or 2,K is a radical of the formula ##STR3## in which D is phenylene which can be substituted by chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy or sulfo, or is naphthalene with optionally 1 or 2 sulfo groups,R.sup.1 denotes hydrogen, chlorine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,R.sup.2 is hydrogen or alkyl of 1 to 4 carbon atoms,G is carboxy, methyl or carbalkoxy of 2 to 5 carbon atoms,Y denotes vinyl, .beta.-sulfatoethyl, .beta.-phosphatoethyl, .beta.-thiosulfatoethyl or .beta.-chloroethyl,Z is the .alpha.- or .beta.-bromoacryloyl or .beta.-chloropropionyl or a radical of the formula ##STR4## with B, D and Y of the abovementioned meanings. The novel dyes are suitable for dyeing hydroxyl- and/or carbamoyl-containing material; on hydroxyl-containing material, such as cellulose fibers, they become fixed not only in the alkaline but also in the weakly acid to neutral range, so that they can be used together with disperse dyes for dyeing blend material composed of cellulose and polyester fibers by the dyeing methods for disperse dyes.

Abstract translation: 具有通式的纤维反应性染料性质的水溶性化合物，其中A是2至6个碳原子的亚烷基或可被1或2个取代基取代的亚苯基，或者是式 IMAGE>其中W是直接键或桥连构件，R'和R *各自表示氢，氯，甲基，甲氧基，乙氧基，羧基或磺基; B是氯或氟; R是氢，氯，1至4个碳原子的烷基或1至4个碳原子的烷氧基; M是氢或碱金属; n表示数字零，1或2，K是式为其中D为可被氯，溴，烷基取代的亚苯基的式 + TR 的基团， 1-4个碳原子的烷氧基，1至4个碳原子的烷氧基，羧基或磺基，或具有任选1或2个磺基的萘，R 1表示氢，氯，1至4个碳原子的烷基或1至4个碳原子的烷氧基，R 2 是氢或1至4个碳原子的烷基，G是2至5个碳原子的羧基，甲基或烷氧基，Y表示乙烯基，β-磺基乙基，β-磷酰乙基，β-硫代硫代乙基或β-氯乙基，Z是α- 或β-溴丙烯酰或β-氯丙酰基或具有上述含义的B，D和Y的式（IMAGE）基团。 新型染料适用于染色羟基和/或氨基甲酰基的材料; 在含羟基的材料如纤维素纤维上，它们不仅在碱性中而且在弱酸至中性范围内变得固定，因此它们可以与分散染料一起用于染色由纤维素和聚酯纤维组成的共混材料 分散染料的染色方法。

公开(公告)号：US4785098A

公开(公告)日：1988-11-15

申请号：US756770

申请日：1985-07-18

Applicant: Hermann Fuchs ,  Hartmut Springer ,  Gunther Schwaiger

Inventor： Hermann Fuchs ,  Hartmut Springer ,  Gunther Schwaiger

IPC: C09B19/02 ,  C09B62/503 ,  C09B19/00

CPC classification number: C09B62/5033

Abstract: Triphendioxazine compounds, which are suitable as fiber-reactive dyestuffs, of the general formula (1) ##STR1## in which R.sup.1 and R.sup.2 are each a hydrogen atom, an optionally substituted alkyl group with 1 to 8 carbon atoms, the substituents being, for example, sulfo, sulfato, carboxy and optionally substituted alkylamino and dialkylamino groups, or a cycloalkyl group which can optionally be substituted by methyl and/or amino, alkanoylamino or benzoylamino, or an optionally substituted phenyl radical, the substituents of which are, for example, sulfo, carboxy, halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, nitro and .beta.-sulfatoethylsulfonyl, or a naphthyl radical which can be substituted by 1, 2 or 3 sulfo groups and/or a fiber-reactive group of the vinylsulfone series, or in which R.sup.1 and R.sup.2, together with the nitrogen atom, can form a heterocyclic radical, and in which the benzene nuclei A can be substituted by 1 or 2 substituents from the group comprising alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 5 carbon atoms, halogen, carboxyl and sulfo, the two radicals X.sup.1 and X.sup.2 are identical to one another or different from one another and are a hydrogen atom, a halogen atom, a cycloalkyl group, an aralkoxy group, an alkoxy group, an aryloxy group, an alkyl group, an aryl group, an aralkyl group or a cyano, carboxy, carbalkoxy, mono- or di-alkylcarbamoyl, arylarylcarbamoyl, alkanoylamino or aroylamino group, and Y represents the vinyl group or ethyl group which contains, in the .beta.-position, a substituent which can be eliminated by an alkali, or is the .beta.-hydroxyethyl group, and M represents a hydrogen atom or an alkali metal or the equivalent of an alkaline earth metal, and the compound (1) contains at least one sulfo or sulfato group.The compounds (1) are used for dyeing material containing hydroxy and/or carboxamide groups, in particular fiber material, such as cellulose fiber material and wool, on which they give deep blue dyeings.

公开(公告)号：US4762916A

公开(公告)日：1988-08-09

申请号：US945491

申请日：1986-12-23

Applicant: Ludwig Schlafer ,  Hartmut Springer ,  Michael Kunze

Inventor： Ludwig Schlafer ,  Hartmut Springer ,  Michael Kunze

IPC: C09B62/47 ,  C07D251/50 ,  C09B62/44 ,  C09B62/475 ,  C09B62/513 ,  D06P1/384 ,  D06P3/66 ,  D06P3/872 ,  C09B62/09 ,  D06P1/382

CPC classification number: D06P1/384 ,  C09B62/4415

Abstract: Water-soluble compounds having fiber-reactive dye properties of the general formula ##STR1## in which A is an alkylene of 2 to 6 carbon atoms or a phenylene which can be substituted by 1 or 2 substituents, or is a radical of the formula ##STR2## in which W is a direct bond or a bridge member and the R' and R* each denote hydrogen, chlorine, methyl, methoxy, ethoxy, carboxy or sulfo;B is chlorine or fluorine;R is hydrogen, chlorine, an alkyl of 1 to 4 carbon atoms or an alkoxy of 1 to 4 carbon atoms;M is hydrogen or an alkali metal;n stands for the number zero, 1 or 2,K is a radical of the formula ##STR3## in which D is phenylene which can be substituted by chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy or sulfo, or is naphthalene with optionally 1 or 2 sulfo groups,R.sup.1 denotes hydrogen, chlorine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,R.sup.2 is hydrogen or alkyl of 1 to 4 carbon atoms,G is carboxy, methyl or carbalkoxy of 2 to 5 carbon atoms,Y denotes vinyl, .beta.-sulfatoethyl, .beta.-phosphatoethyl, .beta.-thiosulfatoethyl or .beta.-chloroethyl,Z is the .alpha.- or .beta.-bromoacryloyl or .beta.-chloropropionyl or a radical of the formula ##STR4## with B, D and Y of the abovementioned meanings. The novel dyes are suitable for dyeing hydroxyl- and/or carbamoyl-containing material; on hydroxyl-containing material, such as cellulose fibers, they become fixed not only in the alkaline but also in the weakly acid to neutral range, so that they can be used together with disperse dyes for dyeing blend material composed of cellullose and polyester fibers by the dyeing methods for disperse dyes.

Abstract translation: 具有通式的纤维反应性染料性质的水溶性化合物，其中A是2至6个碳原子的亚烷基或可被1或2个取代基取代的亚苯基，或者是式 IMAGE>其中W是直接键或桥连构件，R'和R *各自表示氢，氯，甲基，甲氧基，乙氧基，羧基或磺基; B是氯或氟; R是氢，氯，1至4个碳原子的烷基或1至4个碳原子的烷氧基; M是氢或碱金属; n表示数字零，1或2，K是式为其中D为可被氯，溴，烷基取代的亚苯基的式 + TR 的基团， 1-4个碳原子的烷氧基，1至4个碳原子的烷氧基，羧基或磺基，或具有任选1或2个磺基的萘，R 1表示氢，氯，1至4个碳原子的烷基或1至4个碳原子的烷氧基，R 2 是氢或1至4个碳原子的烷基，G是2至5个碳原子的羧基，甲基或烷氧基，Y表示乙烯基，β-磺基乙基，β-磷酰乙基，β-硫代硫代乙基或β-氯乙基，Z是α- 或β-溴丙烯酰或β-氯丙酰基或具有上述含义的B，D和Y的式（IMAGE）基团。 新型染料适用于染色羟基和/或氨基甲酰基的材料; 对于含羟基的材料如纤维素纤维，它们不仅在碱性中而且在弱酸至中性范围内变得固定，从而可以与分散染料一起使用，用于染色由纤维素和聚酯纤维组成的共混材料 分散染料的染色方法。

公开(公告)号：US4745187A

公开(公告)日：1988-05-17

申请号：US8300

申请日：1987-01-29

Applicant: Hartmut Springer

Inventor： Hartmut Springer

IPC: C09B47/24 ,  C09B62/503 ,  C09B62/517 ,  C09B47/08 ,  C09B47/20

CPC classification number: C09B62/517

Abstract: Water-soluble phthalocyanine dyestuffs having vinylsulfonyl or .beta.-substituted ethylsulfonyl groups are prepared by reaction of phthalocyanine sulfonyl chlorides, which may contain sulfo groups, with a primary or secondary amine having vinylsulfonyl or .beta.-substituted ethylsulfonyl groups and, if appropriate, with a second primary or secondary amine of the aliphatic, heterocyclic or aromatic series, in the presence of a pyridinesulfonamide or pyridinecarboxamide.

Abstract translation: 具有乙烯基磺酰基或β-取代的乙基磺酰基的水溶性酞菁染料通过可能含有磺基的酞菁磺酰氯与具有乙烯基磺酰基或β-取代的乙基磺酰基的伯或仲胺反应制备，并且如果合适的话， 在吡啶磺酰胺或吡啶甲酰胺存在下，脂族，杂环或芳族的伯胺或仲胺。

公开(公告)号：US4397649A

公开(公告)日：1983-08-09

申请号：US296442

申请日：1981-08-26

Applicant: Hartmut Springer

Inventor： Hartmut Springer

IPC: C09B47/24 ,  C09B47/26 ,  D06P1/14

CPC classification number: C09B47/26 ,  Y10S8/917 ,  Y10S8/918 ,  Y10S8/919 ,  Y10S8/924

Abstract: Water-soluble phthalocyanine compounds of the formula ##STR1## and their salts, wherein Pc is the radical of the metal-free phthalocyanine or of a phthalocyanine containing metals, X means a hydrogen atom, R.sup.1 and R.sup.2 are a hydrogen atom each or a lower, optionally substituted alkyl group, R.sup.1 and R.sup.2 being identical or different from one another, or R.sup.1 and R.sup.2 together with nitrogen atom and an alkylene radical or another heteroatom and two lower alkylene radicals form a heterocyclic ring, a stands for an integer or fractional number of from 1 to 4, b stands for an integer or fractional number from 0 to 3 and c stands for an integer or fractional number from 0 to 3, with a, b and c being identical or different from one another, their sum, however, being from 1 to 4. The novel phthalocyanines can be prepared by reaction of phthalocyanine sulfochlorides optionally containing sulfo-groups with cyanamide or the salts thereof, optionally with another amine of the formula HNR.sup.1 R.sup.2 with R.sup.1 and R.sup.2 having the above-mentioned meaning, in an aqueous medium, an organic solvent or a mixture thereof, and in the presence of an acid-binding agent, optionally under simultaneous or subsequent partial hydrolysis of sulfochloride groups to sulfo groups. The new phthalocyanine compounds are suitable as water-soluble dyestuffs for dyeing and printing fiber materials of wool, silk, linear polyamides, leather and materials containing hydroxy groups: they may generally be applied to these materials in a neutral or acidic aqueous medium, and are subsequently, optionally after an intermediate drying, fixed under heat.

Abstract translation: 式“IMAGE”的水溶性酞菁化合物及其盐，其中Pc是无金属酞菁或含有金属的酞菁的基团，X表示氢原子，R1和R2各自为氢原子或低级 ，任选取代的烷基，R 1和R 2彼此相同或不同，或者R 1和R 2与氮原子和亚烷基或另外的杂原子和两个低级亚烷基形成杂环，a代表整数或分数 1至4，b代表0至3的整数或分数，c代表0至3的整数或分数，a，b和c彼此相同或不同，但总和 ，从1到4.新的酞菁可以通过任选地含有磺基的酞菁磺酰氯与氨基氰或其盐任选地与式HNR1R2的另一个胺R 1和R 2 ha反应来制备 在含水介质，有机溶剂或其混合物中，并且在酸结合剂的存在下，任选地将磺酰氯基团同时或随后部分水解成磺基。 新的酞菁化合物适用于羊毛，丝线，线性聚酰胺，皮革和含羟基的材料的染色和印花纤维材料的水溶性染料：它们通常可以在中性或酸性水性介质中施用于这些材料，并且 随后，任选地在中间干燥之后，加热固定。

公开(公告)号：US4237050A

公开(公告)日：1980-12-02

申请号：US44158

申请日：1979-05-31

Applicant: Hartmut Springer

Inventor： Hartmut Springer

IPC: C09B47/26 ,  C09B62/517 ,  C09B47/08

CPC classification number: C09B62/517 ,  C09B47/26

Abstract: A process for the preparation of water-soluble phthalocyanine dyestuffs containing a fiber-reactive group of the vinylsulfone series, by reacting phthalocyanine sulfochlorides, optionally containing sulfo groups, with a primary or secondary amine which contains a fiber-reactive group of the vinylsulfone series, and optionally with a further primary or secondary amine in common manner, wherein according to the invention a pyridine-sulfonic acid or a pyridine-carboxylic acid is used as catalyst instead of the pyridine, as used previously. The use of pyridine-sulfonic acids or pyridine-carboxylic acids--which results in the same good reaction rate and yield as the use of pyridine in the preparation of phthalocyanine dyestuffs--avoids the considerable drawbacks occurring in the preparation on an industrial scale, which drawbacks are caused by the toxic properties and the unpleasant smell of the pyridine.

Abstract translation: 通过将任选含有磺基的酞菁磺基氯与含有乙烯基砜系列的纤维反应性基团的伯或仲胺反应制备含有乙烯基砜系列的纤维反应性基团的水溶性酞菁染料的方法， 和任选地与另外的伯胺或仲胺一起使用，其中根据本发明，吡啶 - 磺酸或吡啶 - 羧酸用作催化剂代替吡啶，如前所述。 使用吡啶 - 磺酸或吡啶 - 羧酸 - 与使用吡啶制备酞菁染料相同的良好的反应速率和产率避免了在工业规模的制备中发生的相当大的缺陷，这些缺点 是由吡啶的毒性和难闻的气味引起的。

公开(公告)号：US4185012A

公开(公告)日：1980-01-22

申请号：US718835

申请日：1976-08-30

Applicant: Fritz Meininger ,  Hartmut Springer

Inventor： Fritz Meininger ,  Hartmut Springer

IPC: C09B62/515 ,  C09B45/26 ,  C09B45/28 ,  C09B45/30 ,  C09B45/36

CPC classification number: C09B62/515

Abstract: Water copper complex disazo dyestuffs of the formula ##STR1## had been found wherein A is phenyl or naphthyl, C is phenylene or phenylene substituted by lower alkyl, C and C' together are naphthylene, B is naphthylene, m is 1, 2, 3, 4, 5 or 6 and Y is --SO.sub.2 --CH.dbd.CH.sub.2 or --SO.sub.2 --CH.sub.2 --CH.sub.2 --Z wherein Z is hydroxy, methylsulfonyloxy, p-tolylsulfonyloxy, acetoxy, dimethylamino, diethylamino, thiosulfato, phosphato or sulfato, which are well suitable for dyeing and printing wool, silk and polyamide fibres from an acidic, neutral or slightly alkaline medium, and they are particularly valuable for dyeing and printing cotton and other natural or regenerated cellulose fibres, yielding dyeings and prints distinguished by high tinctorial strengths and intense shades, such as navy blue, grey, black, brown or red brown, having good fastnesses especially to washing, to chlorinated water to light and to dry-cleaning.

Abstract translation: 已经发现了具有式“IMAGE”的水铜络合物双偶氮染料，其中A是苯基或萘基，C是亚苯基或被低级烷基取代的亚苯基，C和C'一起是亚萘基，B是亚萘基，m是1,2,3 ，4,5或6，Y是-SO 2 -CH = CH 2或-SO 2 -CH 2 -CH 2 -Z其中Z是羟基，甲基磺酰氧基，对甲苯磺酰氧基，乙酰氧基，二甲基氨基，二乙基氨基，硫代硫酸根，磷酸酯或硫酸根， 适用于从酸性，中性或微碱性介质中染色和印花羊毛，丝绸和聚酰胺纤维，并且对于染色和印花棉和其他天然或再生纤维素纤维特别有价值，产生染色和印花，由高着色强度和强度 阴影，如海军蓝，灰，黑，棕或红棕色，具有良好的坚牢度，特别是洗涤，氯化水照明和干洗。

公开(公告)号：US4139527A

公开(公告)日：1979-02-13

申请号：US389660

申请日：1973-08-21

Applicant: Fritz Meininger ,  Klaus Hunger ,  Hartmut Springer

Inventor： Fritz Meininger ,  Klaus Hunger ,  Hartmut Springer

IPC: C09B62/45 ,  C09B62/74 ,  C09B62/46

CPC classification number: C09B62/45

Abstract: A water-soluble monoazo-dyestuff having in form of the free acid the formula ##STR1## WHEREIN A represents as a radical of a diazo component phenyl; phenyl substituted by lower alkyl, lower alkylsulfonyl, lower alkoxy, carboxyl, trifluoromethyl, cyano, fluorine, chlorine, bromine, sulfonamido and carbonamido; naphthyl, nitronaphthylene, ##STR2## X represents hydrogen; phenyl; nitrophenylene or naphthyl, R represents as a bridging member --SO.sub.2 --, --CO--, --S--, --CO--NH--, --NH--CO--, --SO.sub.2 --NH--, --NH--SO.sub.2 --, --CH.sub.2 --, --NH-- or --N(lower alkyl)--; B represents as the radical of a coupling component N,N-di(lower alkyl)amino-phenylene, N,N-di (lower alkyl)amino-chloro-phenylene; hydroxyquinoline; diphenylamine; hydroxynaphthylene; hydroxynaphthylene substituted by acetylamino, benzoylamino or ##STR3## aminonaphthylene; ##STR4## substituted on the benzene nucleus by lower alkyl, lower alkoxy, chlorine and bromine; Z represents hydrogen, --COOH or --SO.sub.3 H, Y represents a direct linkage or one of the groupings --CH.sub.2 --, --CH.sub.2 13 CH.sub.2 --, --NH-- or --N(lower alkyl)--, the said groupings --Y--SO.sub.2 --CH.sub.2 --CH.sub.2 --O--PO.sub.3 H.sub.2 and Z being linked to A, B or X, n stands for an integer from 1 to 3 and m stands for an integer from 1 to 5, said dyestuffs being suitable for the dyeing or printing of leather or fibrous materials consisting of native or regenerated cellulose, wool, silk or polyamides, the dyeings and prints obtained on said materials being distinguished by deep tints and very good fastness properties to light and wetting.

Abstract translation: 具有游离酸形式的水溶性单偶氮染料，其中A表示为重氮组分苯基的基团; 低级烷基，低级烷基磺酰基，低级烷氧基，羧基，三氟甲基，氰基，氟，氯，溴，亚磺酰氨基和碳酰氨基取代的苯基; 萘基，亚硝基萘，X表示氢; 苯基; 硝基亚苯基或萘基，R表示作为桥连构件-SO 2 - ， - CO - ， - S - ， - CO-NH-，-NH-CO-，-SO 2 -NH-，-NH-SO 2 - ， - -NH-或-N（低级烷基） - ; B表示作为偶联成分N，N-二（低级烷基）氨基亚苯基，N，N-二（低级烷基）氨基 - 氯 - 亚苯基的基团。 羟基喹啉; 二苯胺; 羟基萘 由乙酰氨基，苯甲酰氨基或氨基亚萘基取代的羟基萘; 在苯核上由低级烷基，低级烷氧基，氯和溴取代的“IMAGE” Z表示氢，-COOH或-SO 3 H，Y表示直接键或-CH 2 - ， - CH 2 13 CH 2 - ， - NH-或-N（低级烷基） - 之一，所述基团-Y-SO 2 -CH 2 -CH2-O-PO3H2和Z与A，B或X连接，n代表1至3的整数，m代表1至5的整数，所述染料适用于皮革或纤维的染色或印花 由天然或再生纤维素，羊毛，丝绸或聚酰胺组成的材料，所述材料上获得的染色和印刷品通过深色调区分，并且对光和润湿具有非常好的牢度性能。