公开(公告)号：US3957751A

公开(公告)日：1976-05-18

申请号：US322374

申请日：1973-01-10

Applicant: August Bauer ,  Ernst Hoyer

Inventor： August Bauer ,  Ernst Hoyer

IPC: C09B62/006 ,  C09B62/008 ,  C09B29/32 ,  C09B29/36

CPC classification number: C09B62/0086

Abstract: Water-soluble monoazo-dyestuff of the formula ##EQU1## in which W is --CN or --CO--NH.sub.2, A is (.beta.-sulfatoethylsulfonyl)-phenylene, (.beta.-sulfatoethylsulfonyl)-di(lower) alkyl-phenylene, (.beta.-sulfatoethylsulfonyl)-lower alkyl-lower alkoxy-phenylene, (.beta.-sulfatoethylsulfonyl)-lower alkoxy-phenylene, (.beta.-sulfatoethylsulfonyl)-monosulfo-naphthylene, monosulfo-di(lower) alkoxy-phenylene, monosulfo-lower alkoxy-lower alkyl-phenylene, disulfo-phenylene or disulfo-naphthylene, and B is disulfo-phenylene, monosulfo-di(lower) alkoxy-phenylene, monosulfo-lower alkxoy-lower-alkyl-phenylene, disulfo-lower alkoxy-phenylene, disulfo-naphthylene, trisulfo-naphthylene, (.beta.-sulfatoethylsulfonyl)-lower alkoxy-lower alkyl-phenylene, (.beta.-sulfatoethylsulfonyl)-lower alkoxy-phenylene, (.beta.-sulfatoethylsulfonyl)-naphthylene, ##SPC1##

公开(公告)号：US4485041A

公开(公告)日：1984-11-27

申请号：US234966

申请日：1981-02-17

Applicant: Ernst Hoyer ,  Fritz Meininger ,  Rudolf Fass

Inventor： Ernst Hoyer ,  Fritz Meininger ,  Rudolf Fass

IPC: C09B62/513 ,  C09B62/44 ,  C09B62/515 ,  D06P3/10 ,  D06P3/66 ,  C09B62/09 ,  C09B62/095 ,  C09B62/533 ,  C09B62/535

CPC classification number: C09B62/4411

Abstract: The novel water-soluble disazo dyestuffs consist of two monoazo dyestuff moieties each containing as diazo component an amine of the benzene or naphthalene series and as coupling component an amino-naphthol-mono- or disulfonic acid. The two moieties are bonded to each other via a triazine radical which carries a halogen atom, and is bound to the amino groups of the coupling components and the diazo components contain a fiber-reactive radical of the vinyl sulfone series. To produce the dyestuffs 2 mols of the diazo compound carrying the fiber-reactive radical of the vinyl sulfone series is coupled with 1 mol of a bivalent coupling component consisting of 2 radicals of the aminonaphthol bound to the triazine ring via the amino groups, or two monoazo dyestuffs each synthesized from the aforesaid diazo component and an aminonaphthol-disulfonic acid coupling component are reacted with a 1,3,5-trihalogeno-triazine. The metal-free dyestuffs can be transformed into the corresponding heavy metal complex dyestuffs, preferably copper, cobalt and chromium complex dyestuffs, by treatment with an agent donating a heavy metal cation. The novel dyestuffs are excellently suitable for dyeing and printing fiber material of natural and regenerated cellulose and natural, regenerated and synthetic polyamides. They are distinguished by clear shades, high tinctorial strength, a very good uptake from a long liquor and a good color-build up. The dyeings obtained therewith have a high fastness to processing and in use.

Abstract translation: 新型水溶性双偶氮染料由两种单偶氮染料组成，每个单偶氮染料部分均含有作为重氮组分的苯或萘系的胺，作为偶联组分为氨基萘酚单或二磺酸。 两个部分通过携带卤素原子的三嗪基彼此键合，并且与偶合组分的氨基结合，重氮组分含有乙烯基砜系列的纤维反应性基团。 为了生产染料，携带乙烯基砜系列的纤维反应性基团的重氮化合物的2摩尔与1摩尔由通过氨基结合到三嗪环的氨基萘酚的2个基团组成的二价偶联组分偶联，或两个 将由上述重氮组分和氨基萘酚 - 二磺酸偶合组分合成的单偶氮染料与1,3,5-三卤代三嗪反应。 通过用赋予重金属阳离子的试剂处理，无金属染料可以转化成相应的重金属络合物染料，优选铜，钴和铬复合染料。 新型染料非常适用于天然和再生纤维素以及天然，再生和合成聚酰胺的染色和印花纤维材料。 它们的特征是清晰的色调，高着色强度，从长酒中很好的摄取和良好的颜色搭配。 由此获得的染色具有高的加工牢度和使用性。

公开(公告)号：US4378312A

公开(公告)日：1983-03-29

申请号：US219499

申请日：1980-12-23

Applicant: Ernst Hoyer ,  Fritz Meininger ,  Rudolf Fass

Inventor： Ernst Hoyer ,  Fritz Meininger ,  Rudolf Fass

IPC: C09B62/44 ,  C09B62/513 ,  C09B62/515 ,  D06P3/66 ,  C09B33/02 ,  C09B33/06

CPC classification number: C09B62/4411 ,  C09B62/513 ,  Y10S534/01

Abstract: Water-soluble compounds and their salts suitable as dyestuffs of the formula ##STR1## in which D is a benzene or naphthalene nucleus, R.sub.1 and R.sub.2 are, inter alia, hydrogen, halogen, lower alkyl, lower alkoxy and sulfo, R.sub.1 being in ortho-position to the azo group, X is a fiber-reactive radical of the vinyl sulfone series, K.sub.1 and K.sub.2 are radicals of coupling components of the acetoacetarylide and pyrozolone series and K.sub.2 additionally denotes a radical of the sulfonaphthol series, the coupling components being bound to the triazine ring via amino groups, Y is a halogen atom, a sulfo group, a thio ether or oxygen ether radical, or a primary, secondary or tertiary amino group, A is an aliphatic, aliphatic-heterocyclic, aliphatic-aromatic or aromatic bridge member and n is zero or one. The novel compounds are prepared, for example, by reacting 2 mols of the diazo component with the fiber-reactive radical of the vinyl sulfone series with 1 mol of a bivalent coupling component containing the two radicals K.sub.1 and K.sub.2 linked to each other by the triazine ring, or 2 triazine radicals linked with each other by bridge member A; or by reacting one mol each of a monoazo compound consisting of the said diazo component with the fiber reactive radical and a coupling component K.sub.1 or K.sub.2 with a corresponding triazine radical additionally carrying a halogen atom capable of reacting with the amino group. The metal-free compounds can be transformed into the corresponding heavy metal complex, preferably copper, cobalt and chromium complex compounds, by treatment with an agent donating a heavy metal cation. The novel compounds are excellently suitable for dyeing and printing fiber material of natural and regenerated cellulose and natural, regenerated and synthetic polyamides. They are distinguished by high tinctorial strength, a very good uptake from a long liquor, a good color-build up. The dyeings and prints obtained therewith have a high fastness to processing and in use.

公开(公告)号：US4370145A

公开(公告)日：1983-01-25

申请号：US324871

申请日：1981-11-25

Applicant: Gunther Schwaiger ,  Ernst Hoyer

Inventor： Gunther Schwaiger ,  Ernst Hoyer

IPC: C09B62/503 ,  C09B62/50 ,  C09B50/00

CPC classification number: C09B62/5036

Abstract: New copper-complex formazan compounds of the general formula: ##STR1## in which A is a phenylene or naphthylene radical which can be substituted by halogen, nitro, lower alkyl, lower alkoxy, lower alkylsulfonyl, phenylsulfonyl and optionally alkylated sulfonamide groups and can also be substituted by the radical Z, defined below, B is a straight-chain or branched-chain alkyl group or alkenyl group, which can be substituted by an optionally substituted phenyl radical, or is a phenyl or naphthyl radical, which can be substituted by halogen, lower alkyl, lower alkoxy and lower carbalkoxy, or is the radical or a furan, thiophene, pyrrole, imidazole, indole, pyrazole, pyridine, pyrimidine, quinoline or benzimidazole, it being possible for B likewise to be substituted by the group Z, defined below, Z denotes a group which confers solubility in water, such as the carboxyl group or sulfo group, one to three of which are bonded to A and/or B, Cu is a copper atom, X denotes an oxygen atom or a carbonyloxy group and is bonded to A in the ortho-position relative to the nitrogen atom, Y represents the vinyl or .beta.-thiosulfatoethyl group and M denotes a hydrogen atom or the equivalent of a metal. The new copper-complex formazan compounds can be prepared in a manner which is in itself customary, for example by reacting an aromatic hydrazone compound of the general formula: ##STR2## in which A, B, X and Z have the abovementioned meaning, with the diazonium compound of an aromatic amine of the general formula: ##STR3## in which M and Y have the abovementioned meaning, and with an agent which donates copper. The new copper-complex formazan compounds have valuable dyestuff properties and are particularly suitable as fiber-reactive dye-stuffs for dyeing, for example, cellulose fiber materials, wool and synthetic polyamide fibers, on which they give strong reddish-tinged to greenish-tinged blue or clear blue dyeings with good fastness to light and wet processing.

公开(公告)号：US4191703A

公开(公告)日：1980-03-04

申请号：US913538

申请日：1978-06-08

Applicant: Hans H. Steuernagel ,  Ernst Hoyer

Inventor： Hans H. Steuernagel ,  Ernst Hoyer

IPC: C07D263/58 ,  C09B62/507 ,  C07C141/18

CPC classification number: C07D263/58 ,  C09B62/507

Abstract: An improved and novel process has been found for the esterification of amino-benzoxazolone compounds containing a .beta.-hydroxyethylsulfonyl group, by means of sulfuric acid or sulfur trioxide, with simultaneous or subsequent hydrolytic cleavage of the oxazolone ring, wherein the esterification and optional hydrolytic ring cleavage are performed in a machine which is operating with a kneading action and effect, using per mol of .beta.-hydroxyethylsulfonyl compound 1 to 20 times the equivalent molar amount of concentrated sulfuric acid, oleum or sulfur trioxide. This novel process has the great advantage that great amounts of sulfuric acid are saved which would contaminate the waste-water, also in form of sodium sulfate formed after the required neutralization. Furthermore, the .beta.-sulfatoethylsulfonyl compounds formed as end-products in the esterification process are obtained in higher yields, in a higher esterification rate and in a higher purity. They may be obtained in form of a powder or plastic mass, which is conveniently transportable and storable, and can advantageously be used, if ring cleavage had taken place, without intermediate isolation of the pure sulfato compound itself, directly for the preparation of azo dyestuffs which are low in content of inert salts and possess a high tinctorial strength and purity.

Abstract translation: 已经发现，通过硫酸或三氧化硫酯化含有β-羟基乙基磺酰基的氨基 - 苯并恶唑酮化合物与恶唑酮环的同时或随后的水解裂解，其中酯化和任选的水解环 在使用每摩尔β-羟乙基磺酰化合物1至20倍等效摩尔浓度的浓硫酸，发烟硫酸或三氧化硫的混合作用和效果的机器中进行裂解。 这种新方法具有很大的优点，可以节省大量的硫酸，这将在所需中和后形成的硫酸钠形式污染废水。 此外，在酯化过程中作为最终产物形成的β-磺酰基乙基磺酰基化合物以更高的产率，更高的酯化速率和更高的纯度获得。 它们可以以粉末或塑料块的形式获得，其方便地可运输和储存，并且可以有利地使用，如果发生环切割而没有中间分离纯的硫酸酯化合物本身直接用于制备偶氮染料 其惰性盐含量低，着色强度和纯度高。

公开(公告)号：US4336190A

公开(公告)日：1982-06-22

申请号：US204915

申请日：1980-11-07

Applicant: Gunther Schwaiger ,  Ernst Hoyer

Inventor： Gunther Schwaiger ,  Ernst Hoyer

IPC: C09B62/503 ,  D06P1/384 ,  C09B50/00

CPC classification number: C09B62/5036 ,  Y10S8/918

Abstract: This invention relates to novel copper complex formazan compounds of the formula ##STR1## in which M is hydrogen or the equivalent of a metal and R is hydrogen or chlorine. The invention also relates to a process for their manufacture. The compounds can be used as dyestuffs, in particular fiber reactive dyestuffs for dyeing cellulose fiber materials, wool, or synthetic polyamide fiber materials for example, on which they exhibit intense blue dyeings having good fastness properties.

Abstract translation: 本发明涉及式为“IMAGE”的新型铜络合物甲an化合物，其中M为氢或相当于金属，R为氢或氯。 本发明还涉及其制造方法。 这些化合物可以用作染料，特别是用于染色纤维素纤维材料，羊毛或合成聚酰胺纤维材料的纤维活性染料，例如，它们表现出具有良好牢度性质的强烈蓝色染色。

公开(公告)号：US4242258A

公开(公告)日：1980-12-30

申请号：US13308

申请日：1979-02-21

Applicant: Walter Noll ,  Fritz Meininger ,  Ernst Hoyer

Inventor： Walter Noll ,  Fritz Meininger ,  Ernst Hoyer

IPC: C09B62/513 ,  D06P3/66 ,  C09B31/30 ,  C09B33/00 ,  C09B35/00

CPC classification number: C09B62/513

Abstract: Water-soluble dyestuffs are described which in the acid form possess the formula ##STR1## wherein D is a benzene or naphthalene nucleus, R.sub.1 is linked to D in ortho-position to the azo group and means hydrogen, halogen, lower alkoxy, lower alkyl, carboxy or sulfo, R.sub.2 is hydrogen, halogen, lower alkyl, lower alkoxy or sulfo and X is the vinyl group or a sulfato-, chloro- or thiosulfatoethyl group, A is a bridging member preferably selected from the diphenylene, diphenylsulfone and diphenylamine series, Z and Z.sup.1 each represent a hydroxy or amino group with the proviso that each Z and each Z.sup.1 have the same meaning. These novel dyestuffs are prepared by diazotization and coupling of the corresponding diazo and coupling components in usual manner known in the art. The novel dyestuffs possess a very valuable fiber-reactivity and are suitable for dyeing natural and regenerated cellulose or natural, regenerated or synthetic polyamide fiber materials. They can easily be applied and fixed by application methods usual and known in the art, and yield on these fiber materials dyeings and prints which possess good fastnesses, especially fastnesses to light, to washing, to perspiration and to cross-dyeing. Their fixation degree on the fiber material and correspondingly their tinctorial strength are outstanding.

Abstract translation: 描述了水溶性染料，其酸形式具有下式：其中D是苯或萘核，R1在与偶氮基的邻位连接到D，并且是指氢，卤素， 低级烷氧基，低级烷基，羧基或磺基，R 2为氢，卤素，低级烷基，低级烷氧基或磺基，X为乙烯基或硫酸酯基，氯代或硫代硫代乙基，A为优选选自二亚苯基 ，二苯基砜和二苯胺系列，Z和Z1各自表示羟基或氨基，条件是每个Z和每个Z1具有相同的含义。 这些新颖的染料通过本领域已知的通常方式的重氮化和相应的重氮和偶合组分的偶联来制备。 新型染料具有非常有价值的纤维反应性，适用于染色天然和再生纤维素或天然，再生或合成聚酰胺纤维材料。 它们可以通过本领域通常和已知的应用方法容易地施加和固定，并且对这些具有良好牢度，特别是耐光性，耐洗涤，出汗和交叉染色的纤维材料染色和印花产率。 它们对纤维材料的固着度和相应的着色力都非常出色。

公开(公告)号：US4035351A

公开(公告)日：1977-07-12

申请号：US576735

申请日：1975-05-12

Applicant: Ludwig Schlafer ,  Ernst Hoyer

Inventor： Ludwig Schlafer ,  Ernst Hoyer

IPC: C09B62/51 ,  C09B29/06 ,  D06P1/06 ,  D06P3/24 ,  D06P3/66

CPC classification number: C09B62/51

Abstract: Water-soluble monoazo-dyestuff of the formula ##STR1## IN WHICH R is alkoxy from 1 to 4 carbon atoms, alkyl from 1 to 4 carbon atoms, alkyl from 1 to 4 carbon atoms, chlorine or bromine, R' is hydrogen, lower alkoxy from 1 to 4 carbon atoms, lower alkyl from 1 to 4 carbon atoms, chlorine or bromine, and X is --SO.sub.2 --CH = CH.sub.2, --SO.sub.2 --CH.sub.2 --CH.sub.2 --OH, --SO.sub.2 --CH.sub.2 --CH.sub.2 --Cl, --SO.sub.2 --CH.sub.2 --CH.sub.2 --O--SO.sub.3 H, --SO.sub.2 --CH.sub.2 --CH.sub.2 --S--SO.sub.3 H, --SO.sub.2 --CH.sub.2 --CH.sub.2 --O--PO.sub.3 H.sub.2, --SO.sub.2 --CH.sub.2 --CH.sub.2 --N (lower alkyl).sub.2 or [--SO.sub.2 --CH.sub.2 --CH.sub.2 --N (lower alkyl).sub.3 ] .sup.(.sup.+) halide.sup.(.sup.-), said dyestuffs being highly suitable for the dyeing or printing of leather, wool, silk, polyurethane and polyamide fibres, particularly, however, of native or regenerated cellulose fibres in the presence of alkaline agents, the dyeings and prints obtainable on cellulose fibres being distinguished by good to very good fastness properties to light and to wetting.

Abstract translation: 其中R为1至4个碳原子的烷氧基，1至4个碳原子的烷基，1至4个碳原子的烷基，氯或溴，R'为氢，较低级的碳原子的水溶性单偶氮染料 1至4个碳原子的烷氧基，1至4个碳原子的低级烷基，氯或溴，X是-SO 2 -CH = CH 2，-SO 2 -CH 2 -CH 2 -OH，-SO 2 -CH 2 -CH 2 - SO2-CH2-CH2-O-SO3H，-SO2-CH2-CH2-S-SO3H，-SO2-CH2-CH2-O-PO3H2，-SO2-CH2-CH2-N（低级烷基）2或[-SO2- CH 2 -CH 2 -N（低级烷基）3]（+）卤化物（ - ），所述染料高度适用于皮革，羊毛，丝绸，聚氨酯和聚酰胺纤维的染色或印花， 天然的或再生的纤维素纤维在碱性试剂的存在下，可在纤维素纤维上获得的染色和印花的特征在于良好至非常好的耐光牢度和光泽度。

公开(公告)号：US4939243A

公开(公告)日：1990-07-03

申请号：US702687

申请日：1985-02-20

Applicant: Fritz Meininger ,  Ernst Hoyer

Inventor： Fritz Meininger ,  Ernst Hoyer

IPC: C09B62/095 ,  C09B62/44 ,  C09B62/515 ,  D06P1/384 ,  D06P3/24 ,  D06P3/66

CPC classification number: C09B62/4416

Abstract: Water-soluble copper complex disazo compounds with fiber-reactive dyestuff properties of the general formula ##STR1## in which m and n are the number zero or 1;the group --SO.sub.2 Y is bonded in the 5-position to the benzene nucleus if n is zero, or in the 4-position if n is zero or 1;the free azo can be bonded to the 6'-or 7'-position of the central naphthalene nucleus;if m is 1, this sulfo is bonded in the 5'-position if the azo is in the 6'-position, and is bonded in the 6'-position if the azo is in the 7'-position;X is chlorine, bromine, ##STR2## in which R.sup.1 represents optionally substituted alkyl with 1 to 4 carbon atoms, optionally substituted aryl or hydrogen,R.sup.2 is optionally substituted alkyl with 1 to 4 carbon atoms or optionally substituted aryl,R.sup.3 is hydrogen or optionally substituted alkyl with 1 to 4 carbon atoms andR.sup.4 is hydrogen, cycloalkyl which is optionally subsituted by 1 to 3 methyl, optionally substituted alkyl with 1 to 4 carbon atoms or optionally substituted aryl, orR.sup.3 and R.sup.4, as alkylene radicals with 1 to 4 carbon atoms together with the nitrogen atom and optionally an oxygen, sulfur or nitrogen atom as a further hetero-atom, form a heterocyclic six-membered radical;Y is vinyl or of the formula--CH.sub.2 --CH.sub.2 --R in whichR is a radical which can be eliminated under alkaline conditions; andM is hydrogen or the equivalent of a metal.

Abstract translation: 水溶性铜络合物双偶氮化合物，其具有通式 + TR 的纤维反应性染料性质，其中m和n为数字0或1; 如果n为0，则基团-SO 2 Y在5位上键合到苯核，如果n为0或1，则在4位上键合; 游离偶氮可以结合到中心萘核的6'或7'位; 如果m为1，如果偶氮在6'位，则该磺基键合在5'位，如果偶氮位于7'-位，则其键合在6'位; X是氯，溴，其中R 1表示任选取代的具有1至4个碳原子的烷基，任选取代的芳基或氢，R 2是任选取代的具有1至4个碳原子的烷基或任选取代的芳基，R 3是氢或任选地 具有1至4个碳原子的取代烷基，R 4为氢，任选被1至3个甲基，任选取代的具有1至4个碳原子的烷基或任选取代的芳基或R 3和R 4取代的环烷基，其具有1至4个亚烷基 碳原子和氮原子以及任选的氧，硫或氮原子作为另外的杂原子形成杂环六元基; Y是乙烯基或式-CH 2 -CH 2 -R，其中R是在碱性条件下可被除去的基团; M为氢或相当于金属。

公开(公告)号：US4334076A

公开(公告)日：1982-06-08

申请号：US820884

申请日：1977-08-01

Applicant: Hans H. Steuernagel ,  Ernst Hoyer ,  Fritz Meininger

Inventor： Hans H. Steuernagel ,  Ernst Hoyer ,  Fritz Meininger

IPC: C07D231/24 ,  C07D231/26 ,  C07D231/46 ,  C09B62/507 ,  C07C139/00 ,  C07C139/10 ,  C07D231/02 ,  C07D231/34

CPC classification number: C09B62/507 ,  C07D231/24 ,  C07D231/26 ,  C07D231/46

Abstract: An improved and novel process had been found for the esterification of aminophenol, amino-benzanilide and pyrazolone compounds containing a .beta.-hydroxyethylsulfonyl group, by means of sulfuric acid or sulfur trioxide which improvement is characterized by that the esterification is performed in a machine which is operating with a kneading action and effect, using per mol .beta.-hydroxyethylsulfonyl compound 1 to 2.5 times the equivalent molar amount of concentrated sulfuric acid, oleum or sulfur trioxide. This novel process has the great advantage that great amounts of sulfuric acid are saved which could charge the waste water, also in form of sodium sulfate formed after the required neutralization. Furthermore, the .beta.-sulfatoethylsulfonyl compounds formed as end-products in the esterification process are prepared by this novel process in higher yields, in a higher degree of esterification rate and in a higher purity. They are obtained in form of a powder or plastic mass from the kneading machine, which is well transportable and storable, and can advantageously used in the form of this consistency, without intermediate isolation of the pure .beta.-sulfato compound itself, directly for the preparation of azo dyestuffs which are poor of inert salts, possess a high tinctorial strength and purity.

Abstract translation: 已经发现通过硫酸或三氧化硫酯化氨基苯酚，氨基 - 苯甲酰苯胺和含有β-羟基乙基磺酰基的吡唑啉酮化合物的改进和新方法，其改进的特征在于酯化是在机器中进行的， 以混合作用和效果操作，使用每摩尔β-羟乙基磺酰化合物1倍至2.5倍于当量摩尔浓度的浓硫酸，发烟硫酸或三氧化硫。 这种新方法具有很大的优点，可以节省大量的硫酸，这可以在所需中和后形成的硫酸钠形式对废水进行充电。 此外，在酯化过程中形成作为终产物的β-磺基乙基磺酰基化合物通过该新方法以更高的收率，更高的酯化速率和更高的纯度制备。 它们是由捏合机形式的粉末或塑料块形成的，该混合机具有良好的可运输和储存性能，并且可有利地以这种稠度的形式使用，而不用直接用于制备的纯β-硫酸酯化合物本身的中间分离 的惰性盐不良的偶氮染料具有高的着色强度和纯度。