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1. 发明授权

US4855411A Water-soluble, monoazo dyes containing a ureido group and two sulfonyl fiber-reactive groups 失效
标题翻译：含有脲基和两个磺酰基纤维反应性基团的水溶性单偶氮染料
公开(公告)号：US4855411A
公开(公告)日：1989-08-08
申请号：US170585
申请日：1988-03-17
申请人： Glenn A. Thompson , Anthony J. Corso , Hans H. Steuernagel
发明人： Glenn A. Thompson , Anthony J. Corso , Hans H. Steuernagel
IPC分类号： C09B62/507
CPC分类号： C09B62/507
摘要： This invention is directed to new water-soluble, monoazo dyes having the following general formula: ##STR1## in which: X and Y are independently selected from the group consisting of: ##STR2## R, R.sub.1, R.sub.2 are independently selected from H, lower alkyl of one to four carbons and sulfonated lower alkyl;A is a phenyl or napthyl radical optionally substituted with halogen, hydroxy, lower alkyl, lower alkoxy, carboxylic acid or sulfonic acid;W is a phenyl or naphthyl radical optionally substituted by carboxylic acid, sulfonic acid, amino, amido, lower alkyl, lower alkoxy, hydroxy or halogen groups;Z is a phenyl radical optionally substituted with halogen, lower alkoxy or lower alkyl groups; andcopper, chromium, cobalt and nickel metallized complexes of said dyestuffs.The dyes of this invention on cellulose textiles have high tinctorial strength, purity of shade, light and wash fastness particularly chlorine wash fastness. They are particularly useful in high temperature dyeing operations and can be prepared into stable aqueous solutions for use in continuous dyeing operations. The dyes of this invention provide a full range of shades and exhibit superior color yield and leveling in chemical pad steaming dyeing. They build strongly with superior fixation and have superior stability in acidic and alkaline environments.
摘要翻译：本发明涉及具有以下通式的新的水溶性单偶氮染料：其中：X和Y独立地选自CHCH2，CH2CH2SSO3H，CH2CH2Br，CH2CH2OCOCH3，CH2CH2OH，CH2CH2OPO3H2 ， + TR CH2CH2NR1R2; R，R 1，R 2独立地选自H，1至4个碳的低级烷基和磺化的低级烷基; A是任选被卤素，羟基，低级烷基，低级烷氧基，羧酸或磺酸取代的苯基或萘基; W是任选被羧酸，磺酸，氨基，酰氨基，低级烷基，低级烷氧基，羟基或卤素基团取代的苯基或萘基; Z是任选被卤素，低级烷氧基或低级烷基取代的苯基; 和所述染料的铜，铬，钴和镍金属化络合物。本发明的染料在纤维素纺织品上具有高着色强度，色度纯度，耐洗色牢度，特别是耐氯洗牢度。它们在高温染色操作中特别有用，并且可以制备成用于连续染色操作的稳定的水溶液。本发明的染料提供全系列的色调并且在化学垫蒸汽染色中表现出优异的色彩产率和流平性。它们以优异的固定作用，并且在酸性和碱性环境中具有优异的稳定性。

2. 发明授权

US4760134A Process for the preparation of the copper complex disazo compounds from disazo compounds containing an O'-alkoxyaniline group by coppering dimethylation at a pH at about 3-6 失效
标题翻译：通过在约3-6的pH下通过铜化二甲基化来制备包含O'-烷氧基苯胺基团的双偶氮化合物的铜络合物双偶氮化合物的方法
公开(公告)号：US4760134A
公开(公告)日：1988-07-26
申请号：US770341
申请日：1985-08-28
申请人： Anthony J. Corso , Fritz Meininger , Hans H. Steuernagel
发明人： Anthony J. Corso , Fritz Meininger , Hans H. Steuernagel
IPC分类号： C09B62/515 , C09B45/08 , C09B45/28
CPC分类号： C09B62/515
摘要： This invention is that of an improved process for preparing 1:1 copper complex disazo compounds which comprises treating a disazo compound of the following general formula (2): ##STR1## wherein: M is hydrogen or the equivalent monovalent or divalent metal andY is the vinyl group or CH.sub.2 --CH.sub.2 --Z wherein Z is a radical that can be eliminated by an alkaline agentwith a copper donor at a temperature from about 70.degree. to about 130.degree. C. and at a pH from about 3 to about 6. The compounds of the process of the invention are used as dyestuffs.
摘要翻译：本发明是制备1：1铜络合物双偶氮化合物的改进方法，其包括处理下列通式（2）的双偶氮化合物：其中：M为氢或相当的一价或二价金属并且Y是乙烯基或CH 2 -CH 2 -Z，其中Z是在约70℃至约130℃的温度下可以由铜供体在碱性试剂中除去的基团，并且在约3至约3至约3 本发明方法的化合物用作染料。

3. 发明授权

US4191703A Process for the manufacture of sulfuric acid semi-ester compounds 失效
标题翻译：制备硫酸半酯化合物的方法
公开(公告)号：US4191703A
公开(公告)日：1980-03-04
申请号：US913538
申请日：1978-06-08
申请人： Hans H. Steuernagel , Ernst Hoyer
发明人： Hans H. Steuernagel , Ernst Hoyer
IPC分类号： C07D263/58 , C09B62/507 , C07C141/18
CPC分类号： C07D263/58 , C09B62/507
摘要： 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.
摘要翻译：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。

4. 发明授权

US4906738A Water-soluble phenyl- or naphthyl-azo-carboxypyrazolone compounds, containing a fiber-reactive group with a chloratriazinyl moiety and a group of the vinylsulfone series in the pyrazolone coupling component, suitable as dyestuffs 失效
公开(公告)号：US4906738A
公开(公告)日：1990-03-06
申请号：US722759
申请日：1985-04-15
申请人： Folker Kohlhaas , Fritz Meininger , Hans H. Steuernagel
发明人： Folker Kohlhaas , Fritz Meininger , Hans H. Steuernagel
IPC分类号： C09B62/51 , C09B62/44 , D06P1/382 , D06P1/384
CPC分类号： C09B62/4413
摘要： Water-soluble monoazo compounds of the general formula (1) ##STR1## in which D is a phenyl radical or naphthyl radical, either of which is substituted and mandatorily contains at least one group which imparts solubility in water and D is substituted, for example by 1, 2 or 3 substituents which can be selected from the set consisting of 1 sulfamoyl, 1 carbamoyl, 1 trifluoromethyl, 1 benzothiazol-2-yl, 1 sulfobenzothiazol-2-yl, 1 methylbenzothiazol-2-yl, 1 methylsulfobenzothiazol-2-yl, 1 styryl, 1 nitrostyryl, 1 sulfostyryl and 1 nitrosulfostyryl group and, preferably, three sulfo groups, two carboxy groups, two alkyl groups of 1-4 C atoms, two alkoxy groups of 1-4 C atoms, 1 bromine atom and two chlorine atoms and one or two groups of the formula --SO.sub.2 --Z with Z of the meaning below, and the group --SO.sub.2 --Z can also be bonded to one of the substituents and Z represents the .beta.-hydroxyethyl group or, preferably a group Y of the meaning indicated below, M is a hydrogen atom or an equivalent of a monovalent, divalent or trivalent metal of the main groups of the periodic system, R is the methyl group, a carboxy group or a carboalkoxy group of 2 to 5 C atoms, R.sup.1 is a hydrogen atom or an alkyl group of 1 to 4 C atoms, R.sup.2 is a hydrogen atom, an alkyl group of 1-4 C atoms, an alkoxy group of 1-4 C atoms or a chlorine atom, R.sup.3 is a hydrogen atom, and alkyl group of 1-4 C atoms or an alkoxy group of 1-4 C atoms, Y is the vinyl group or an ethyl group which contains a radical in .beta.-position which can be eliminated as an anion under alkaline conditions, such as, for example, a .beta.-sulfatoethyl group, and Hal is a chlorine or fluorine atom.The new monoazo compounds are prepared analogously to known procedures from the components (the diazo component D-NH.sub.2, the pyrazolone coupling component with an aminosulfophenyl radical in the 1-position, cyanuric chloride or cyanuric fluoride, and an aniline compound containing the group --SO.sub.2 --Y) evident from the formula (1). They have very good fiber-reactive dyestuff properties and produce, for example, on cellulose fiber materials deep and fast dyeings and prints.

5. 发明授权

US4315865A Process for the production of sulfuric acid semiester compounds by sulfation in a machine employing kneading action 失效
标题翻译：在采用搅拌作用的机器中通过硫酸化生产硫酸半酯化合物的方法
公开(公告)号：US4315865A
公开(公告)日：1982-02-16
申请号：US911136
申请日：1978-05-31
申请人： Ernst Hoyer , Hans H. Steuernagel , Dieter Wagner
发明人： Ernst Hoyer , Hans H. Steuernagel , Dieter Wagner
IPC分类号： C09B43/24 , C09B62/503 , C09B1/30 , C09B45/00 , C09B57/14
CPC分类号： C09B62/503
摘要： Improved process for the sulfatation of the hydroxy group of a .beta.-hydroxy-ethylsulfonyl group present in compounds selected from the dyestuff class which comprises carrying out the reaction in a machine operating with a kneading action and effect and with the use of only 1 to 5 times the equimolar amount of a concentrated sulfuric acid, of oleum or sulfur dioxide itself. The .beta.-sulfatoethylsulfonyl group containing dyestuffs, thus prepared have a high purity and are obtained in a high yield and esterification rate. Above all, the novel process is distinguished by a highly reduced salt and acid content of the waste water.
摘要翻译：存在于选自染料类的化合物中的β-羟基 - 乙基磺酰基的羟基的硫酸化的改进方法包括在具有捏合作用和效果的机器中进行反应，并且仅使用1至5 倍等量的浓硫酸，发烟硫酸或二氧化硫本身。由此制备的含有β-磺酰基乙磺酰基的染料具有高纯度并且以高产率和酯化速率获得。最重要的是，新方法的特点是废水的盐和酸含量高度降低。

6. 发明授权

US4948917A Process for the preparation of beta-chloroethylsulfonylaryl isocyanates 失效
标题翻译：制备β-氯乙基磺酰基芳基异氰酸酯的方法
公开(公告)号：US4948917A
公开(公告)日：1990-08-14
申请号：US479660
申请日：1990-02-14
申请人： Hans H. Steuernagel
发明人： Hans H. Steuernagel
IPC分类号： B01J31/02 , C07B61/00 , C07C315/04 , C07C317/32
CPC分类号： C07C315/04
摘要： Process for the preparation of .beta.-chloroethylsulfonylaryl isocyanates of the formula (1)Cl--H.sub.2 C--H.sub.2 C--O.sub.2 S--A--NCO (1)wherein A is a phenylene radical, which can contain substituents from the series comprising alkyl(C.sub.1 -C.sub.6), alkoxy(C.sub.1 -C.sub.6), chlorine, bromine and nitro, or a naphthylene radical, by allowing at least 2 moles of phosgene to act on 1 mole of .beta.-hydroxyethylsulfonyl-arylamine of the formula (2)HO--H.sub.2 C--H.sub.2 C--O.sub.2 S--A--NH.sub.2 (2)wherein A has the abovementioned meaning, in the presence of a catalyst at temperatures of about 100.degree. to 200.degree. C., if appropriate in an inert solvent.
摘要翻译：制备式（1）C 1 -H 2 C-H 2 C-O 2 S-A-NCO（1）的β-氯乙基磺酰基芳基异氰酸酯的方法其中A是亚苯基，其可以含有包含（C1-C6）烷基，烷氧基（C 1 -C 6），氯，溴和硝基或亚萘基，通过使至少2摩尔的光气作用于式（2）的1摩尔β-羟基乙基磺酰基 - 芳基胺HO-H 2 C-H 2 C- O 2 S-A-NH 2（2）其中A具有上述含义，在催化剂存在下，在约100至200℃的温度下，如果合适，在惰性溶剂中。

7. 发明授权

US4334076A Process for the preparation of sulfuric acid semiester ethylsulfonyl compounds of aminophenols, aminobenzanilides or phenylpyrazolones by esterification with sulfuric acid and/or sulfur trioxide in a kneader 失效
标题翻译：在捏合机中用硫酸和/或三氧化硫酯化制备氨基苯酚，氨基苯甲酰苯胺或苯基吡唑啉的硫酸半酯乙基磺酰基化合物的方法
公开(公告)号：US4334076A
公开(公告)日：1982-06-08
申请号：US820884
申请日：1977-08-01
申请人： Hans H. Steuernagel , Ernst Hoyer , Fritz Meininger
发明人： Hans H. Steuernagel , Ernst Hoyer , Fritz Meininger
IPC分类号： C07D231/24 , C07D231/26 , C07D231/46 , C09B62/507 , C07C139/00 , C07C139/10 , C07D231/02 , C07D231/34
CPC分类号： C09B62/507 , C07D231/24 , C07D231/26 , C07D231/46
摘要： 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.
摘要翻译：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。

8. 发明授权

US4252529A Copper, cobalt or chromium complex monoazo compounds, processes for their manufacture, their use as dyestuffs and fiber materials dyed with these dyestuffs 失效
标题翻译：铜，钴或铬复合单偶氮化合物，其制造方法，用作染料和用这些染料染色的纤维材料
公开(公告)号：US4252529A
公开(公告)日：1981-02-24
申请号：US143190
申请日：1980-04-24
申请人： Hans H. Steuernagel
发明人： Hans H. Steuernagel
IPC分类号： C09B45/14 , C09B62/515 , D06P3/10 , D06P3/66 , C07C107/08
CPC分类号： C09B45/14 , C09B62/515
摘要： Water-soluble copper, cobalt and chromium complex monoazo compounds of which the metal-free monoazo compound contains as diazo component an aminophenol or aminonaphthol compound subtituted by a fiber-reactive radical of the vinyl sulfone series, the aminophenol possibly being substituted by a lower alkyl, lower alkoxy, nitro, sulfonic acid group, or a chlorine or bromine atom and the naphthol possibly being substituted by a sulfo group, and as coupling component a 6-sulfonaphthol(8) which may be substituted by a sulfo group in the adjacent aromatic nucleus and must be substituted by the monoamide radical of succinic acid, glutaric acid or adipic acid.They are prepared by diazotization of the corresponding aniline and naphthylamine compounds containing, in o-position to the amino group, a hydrogen atom, a hydroxy group or a lower alkoxy group, with subsequent coupling with the above coupling component and transformation into the metal complex compounds by an agent donating copper, cobalt or chromium, optionally in the presence of an oxidant. The coupling components can be prepared by reacting the corresponding aminonaphthol mono- or disulfonic acids with a dihalide or anhydride of succinic acid, glutaric acid or adipic acid.The metal complex compounds have outstanding dyestuff properties. They have a good solubility in water and are especially suitable for dyeing fiber materials of natural and regenerated cellulose, of natural, regenerated or synthetic polyamides of polyurethanes as well as leather. The dyeings display very good fastness to light and to wet processing, a high color strength and portions of the dyestuff which have not been fixed on the fiber can be washed off easily.
摘要翻译：水溶性铜，钴和铬络合物单偶氮化合物，其中无金属单偶氮化合物含有作为重氮组分的氨基苯酚或氨基萘酚化合物，其由乙烯基砜系列的纤维反应性基团取代，氨基苯酚可能被低级烷基，低级烷氧基，硝基，磺酸基或氯或溴原子，萘酚可以被磺基取代，作为偶联成分，可以在相邻芳香中被磺基取代的6-磺基萘酚（8）核并且必须被琥珀酸，戊二酸或己二酸的单酰胺基取代。它们是通过对相应的苯胺和萘胺化合物的重氮化制备的，其中在氨基的邻位置含有氢原子，羟基或低级烷氧基，随后与上述偶合组分偶合并转化成金属络合物任选地在氧化剂存在下，通过提供铜，钴或铬的试剂的化合物。偶联组分可以通过使相应的氨基萘酚单 - 或二磺酸与琥珀酸，戊二酸或己二酸的二卤化物或酸酐反应来制备。金属络合物具有优异的染料性能。它们在水中具有良好的溶解性，特别适用于天然和再生纤维素，天然，再生或合成的聚氨酯聚酰胺以及皮革的纤维材料的染色。染色显示出非常良好的耐光牢度和湿法加工性，高色强度和未固定在纤维上的部分染料可以容易地洗掉。

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