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1. 发明授权

US4778911A Process for preparation of 3-(acyl)amino-4-alkoxy-phenyl-.beta.-hydroxyethyl-sulfone (sulfonates) 失效
标题翻译：制备3-（酰基）氨基-4-烷氧基 - 苯基-β-羟基乙基砜（磺酸盐）的方法
公开(公告)号：US4778911A
公开(公告)日：1988-10-18
申请号：US065678
申请日：1987-06-18
申请人： Peter Hess , Folker Kohlhaas , Theodor Papenfuhs
发明人： Peter Hess , Folker Kohlhaas , Theodor Papenfuhs
IPC分类号： C07C315/00 , C07C67/00 , C07C313/00 , C07C315/04 , C07C317/36 , C07C317/40 , C07C141/16 , C07C103/127 , C07C103/22
CPC分类号： C07C315/00
摘要： A process for the preparation of 3-(acyl)amino-4-alkoxy-phenyl-.beta.-hydroxyethyl-sulfone (sulfates) of the formula (1) ##STR1## in which R.sub.1 is alkyl having 1-4 carbon atoms and R.sub.2 is hydrogen or one of the groupings ##STR2## with the proviso that n=1 if R.sub.2 =H and n=0 if R.sub.2 =acyl, by converting 2-alkoxyacylanilines of the formula (2) ##STR3## in which R.sub.1 and R.sub.2 have the meanings given, in a known manner to the corresponding sulfochlorides substituted in the p-position relative to the alkoxy group, reducing the sulfochlorides with an alkali metal sulfite or ammonium sulfite in an aqueous medium at pH 7.0-8.5 and at -5 to +40.degree. C. to give the corresponding sulfinates, alkoxylating the latter with ethylene oxide in an aqueous medium at pH 6.0-8.5 and 40.degree.-80.degree. C. to give the 3-acylamino-4-alkoxyphenyl-.beta.-hydroxyethyl-sulfones of the formula (1) (with R.sub.2 =acyl and n=0) and, if appropriate, esterifying the latter, with deacylation, with concentrated sulfuric acid at 70.degree.-150.degree. C. to give the compounds of the said formula (1) (with R.sub.2 H and n=1).
摘要翻译：制备式（1）的3-（酰基）氨基-4-烷氧基 - 苯基-β-羟基乙基砜（硫酸盐）的方法其中R1是具有1-4个碳原子的烷基并且R2是氢或分组 + TR ，条件是如果R2 = H，n = 1，如果R2 =酰基，则n = 0，通过将2-烷氧基苯甲酰苯胺式（2）其中R 1和R 2具有已知方式给予在相对于烷氧基的p位取代的对应的磺基氯的含义，用碱金属亚硫酸盐或铵还原磺酰氯亚硫酸盐在pH 7.0-8.5和-5至+ 40℃的水性介质中，得到相应的亚硫酸盐，将其与环氧乙烷在pH 6.0-8.5和40 -80℃的水性介质中烷氧基化成得到式（1）的3-酰基氨基-4-烷氧基苯基-β-羟乙基砜（R2 =酰基和n = 0），并且如果合适的话，将后者酯化，用去酰基化，浓缩硫酸在70-150℃，得到所述式（1）的化合物（其中R2H和n = 1）。

2. 发明授权

US4992589A Substituted phenyl hydroxyethyl sulfones, and process for their preparation 失效
标题翻译：取代的苯基羟乙基砜，及其制备方法
公开(公告)号：US4992589A
公开(公告)日：1991-02-12
申请号：US231655
申请日：1988-08-10
申请人： Hermann Fuchs , Theodor Papenfuhs , Werner Brodt , Folker Kohlhaas
发明人： Hermann Fuchs , Theodor Papenfuhs , Werner Brodt , Folker Kohlhaas
IPC分类号： C07D295/096 , C07D295/13 , C07D295/135 , C09B62/503
CPC分类号： C07D295/096 , C07D295/13 , C07D295/135 , C09B62/503
摘要： Compounds of the formula (1) ##STR1## in which X denotes a sulfur atom or the group ##STR2## in which R denotes a hydrogen atom, an alkylene-C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 - or alkyl-C.sub.1 -C.sub.6 - group, each of which can be substituted by hydroxyl, sulfo, carboxyl or cyano groups, R.sub.1 denotes a hydrogen atom or an alkyl-C.sub.1 -C.sub.6 -group which can be substituted by --SO.sub.3 M or COOM groups (where M denotes an H, Li, Na, K or Ca atom), hydroxyl, amino, methylamino, acetylamino, alkyl-C.sub.1 -C.sub.4 -sulfonylamino, methoxy, ethoxy, .beta.-hydroxyethylsulfonyl, phenyl, monosulfophenyl, disulfophenyl, or 4-[.beta.-hydroxyethylsulfonyl]-2-sulfophenyl groups, or represents a phenyl or naphthyl group, each of which can be substituted by --SO.sub.3 M or COOM groups (where M denotes an H, Li, Na, K or Ca atom), alkyl-C.sub.1 -C.sub.4 -, alkoxy-C.sub.1 -C.sub.4 -, amino, methylamino, alkyl-C.sub.1 -C.sub.4 -sulfonylamino or acetylamino groups, and R.sub.2 is hydrogen or oxygen, and process for their preparation by reacting compounds of the formula (2) ##STR3## in which Y denotes a chlorine or bromine atom, with a compound of the formula (3)H--X--R.sub.1 (1)in which X and R.sub.1 have the stated meanings, at between 20.degree. and 90.degree. C. in a solvent which is suitable in respect of the reactants of the formulae (2) and (3) and in the presence of an acid-binding agent to give compounds of the formula (4) ##STR4## in which X and R.sub.1 have the stated meanings, and if desired using these compounds in a manner known per se to compounds of the formula (1) where R.sub.2 =H.
摘要翻译：式（1）的化合物其中X表示硫原子或基团“IMAGE”，其中R表示氢原子，亚烷基-C 1 -C 4 - 烷氧基-C 1 -C 6 - 或烷基 - C1-C6-基团，它们各自可被羟基，磺基，羧基或氰基取代，R1表示氢原子或可被-SO3M或COOM基团取代的烷基-C1-C6-基团（其中M表示 H，Li，Na，K或Ca原子），羟基，氨基，甲基氨基，乙酰氨基，烷基-C 1 -C 4 - 磺酰基氨基，甲氧基，乙氧基，β-羟基乙基磺酰基，苯基，单磺基苯基，二磺基苯基或4- ] - 表示可以被-SO 3 M或COOM基团取代的苯基或萘基（其中M表示H，Li，Na，K或Ca原子），烷基-C 1 -C 4 - ，烷氧基-C 1 -C 4 - ，氨基，甲基氨基，烷基-C 1 -C 4 - 磺酰基氨基或乙酰基氨基，R 2是氢或氧，并且通过使式（2）化合物（2）其中Y表示与其中X和R 1具有所述含义的式（3）化合物HX-R1（1）在20至90℃之间的溶剂中，在适合于式（2）和（3）的反应物和酸结合剂的存在下反应得到式（4）化合物其中X和R 1具有所述含义，如果需要，使用这些化合物本身已知于式（1）的化合物，其中R 2 = H。

3. 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.

4. 发明授权

US4492654A Water-soluble azo compounds, a process for their preparation and their use as dyes 失效
标题翻译：水溶性偶氮化合物，其制备方法及其作为染料的用途
公开(公告)号：US4492654A
公开(公告)日：1985-01-08
申请号：US515442
申请日：1983-07-20
申请人： Ernst Hoyer , Folker Kohlhaas , Fritz Meininger
发明人： Ernst Hoyer , Folker Kohlhaas , Fritz Meininger
IPC分类号： C09B33/10 , C09B62/513 , D06P1/384 , D06P3/32 , C09B33/02 , C09B31/02
CPC分类号： C09B62/513
摘要： Disazo compounds corresponding to the general formula (1) ##STR1## as well as their metal salts, in which D.sub.1 denotes the benzene or naphthalene nucleus, which can be further substituted by one or two substituents from the group of fluorine, chlorine, bromine, carboxy, lower alkyl, lower alkoxy and nitro and/or one, two or three sulfo groups, D.sub.2 is the benzene or naphthalene nucleus, which is substituted by the substituent X defined below and, in addition to the group --SO.sub.2 --Y, can be further substituted by one or two substituents from the group of carboxy, lower alkyl and lower alkoxy and/or by one substituent from the group of fluorine, chlorine, bromine and nitro and/or one, two or three sulfo groups, X denotes a fluorine, chlorine or bromine atom, which is necessarily bonded to D.sub.2 in ortho-position to the azo group, Y denotes the vinyl, .beta.-sulfatoethyl, .beta.-chloroethyl, .beta.-thiosulfatoethyl or a .beta.-acyloxyethyl group with the acyl radical of a lower alkanecarboxylic acid or of a benzoic acid or of a benzenesulfonic acid, and a and b each represent the number zero or 1, the sum of (a+b) being equal to 1 or 2. These compounds (1) are very suitable as fiber-reactive dyes for dyeing, for example natural or regenerated cellulose fiber, wool or synthetic polyamide fibers. They give on these materials intense dyeings and prints of good fastness properties, and are distinguished, in particular, by a good stability to copper ions, when used in printing processes.
摘要翻译：对应于通式（1）的双偶氮化合物（1）及其金属盐，其中D1表示苯或萘核，其可以进一步被氟，氯的一个或两个取代基取代，溴，羧基，低级烷基，低级烷氧基和硝基和/或一个，两个或三个磺基，D2是苯或萘核，其被下面定义的取代基X取代，并且除了-SO 2 - Y可以进一步被一个或两个来自羧基，低级烷基和低级烷氧基的取代基和/或由氟，氯，溴和硝基和/或一个，两个或三个磺基组中的一个取代基取代， X表示氟原子，氯原子或溴原子，其与偶氮基的邻位必须与D2结合，Y表示乙烯基，β-磺基乙基，β-氯乙基，β-硫代乙酰基乙基或β-酰氧基乙基，与酰基低级链烷羧酸的自由基或苯甲酸或苯磺酸，a和b各自表示数字0或1，（a + b）之和等于1或2.这些化合物（1）非常适合作为纤维反应性用于染色的染料，例如天然或再生纤维素纤维，羊毛或合成聚酰胺纤维。它们赋予这些材料强烈的染色和良好的牢度性质的印刷品，特别是当用于印刷工艺时，特别是对铜离子具有良好的稳定性。

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