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：US4769446A

公开(公告)日：1988-09-06

申请号：US485682

申请日：1983-04-18

Applicant: Anthony J. Corso ,  Fritz Meininger ,  Thomas S. Phillips

Inventor： Anthony J. Corso ,  Fritz Meininger ,  Thomas S. Phillips

IPC: C09B62/51 ,  D06P1/384 ,  D06P3/10 ,  D06P3/66 ,  D06P1/38

CPC classification number: C09B62/51

Abstract: A water-soluble fiber-reactive red dyestuff is disclosed which, in its free acid form, has the formula ##STR1## wherein X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Z wherein Z is --OH, --Cl, --Br, --OSO.sub.3 H, --SSO.sub.3 H, --OPO.sub.3 H.sub.2, --O.sub.2 CCH.sub.3, --O.sub.2 CCH.sub.2 CH.sub.3 or --N(lower alkyl).sub.2. Liquid compositions of said dyestuff are also disclosed. This dyestuff yields brilliant red shades on cellulosic materials having excellent fastness properties and superior color yield and build up.

Abstract translation: 公开了一种水溶性纤维反应性红色染料，其游离酸形式具有下式：其中X为-CH = CH 2或-CH 2 CH 2 -Z，其中Z为-OH，-Cl，-Br， - OSO 3 H，-SSO 3 H，-OPO 3 H 2，-O 2 CCH 3，-O 2 CCH 2 CH 3或-N（低级烷基）2。 还公开了所述染料的液体组合物。 该染料在纤维素材料上产生辉煌的红色色调，具有优异的坚牢度和优异的色彩收获率并增强。

公开(公告)号：US4725675A

公开(公告)日：1988-02-16

申请号：US558548

申请日：1983-12-05

Applicant: Fritz Meininger ,  Joachim Otten

Inventor： Fritz Meininger ,  Joachim Otten

IPC: C09B62/51 ,  C09B62/44 ,  D06P1/38 ,  C09B62/085 ,  C09B62/45 ,  D06P3/10

CPC classification number: C09B62/4413

Abstract: Water-soluble azo compounds of the formula (1) ##STR1## in which R is hydrogen or alkyl of 1 to 4 carbon atoms, X is alkyl of 1 to 6 carbon atoms substituted by carboxy or sulfo, or is phenyl substituted by 1 or 2 sulfo or carboxy or both, and Z is vinyl, .beta.-thiosulfatoethyl or .beta.-sulfatoethyl and M is hydrogen or the equivalent of a metal, and in which the second sulfo group in the naphthalene is bonded in the m-position or p-position relative to the acylated amino group. The new azo compounds are very valuable dyestuffs having fiber-reactive properties, and give color-fast and deep dyeings and prints on fiber materials made of cellulose or synthetic or natural polyamide fibers.

Abstract translation: 式（1）的水溶性偶氮化合物其中R为氢或1至4个碳原子的烷基，X为被羧基或磺基取代的1至6个碳原子的烷基，或者是 被1或2个磺基或羧基取代的苯基或两者，Z是乙烯基，β-硫代硫代乙基或β-磺基乙基，M是氢或等价金属，其中萘中的第二个磺基键合在m 位或相对于酰化氨基的对位。 新的偶氮化合物是具有纤维反应性质的非常有价值的染料，并且在由纤维素或合成或天然聚酰胺纤维制成的纤维材料上进行着色和深色染色和印花。

公开(公告)号：US4442288A

公开(公告)日：1984-04-10

申请号：US373789

申请日：1982-04-30

Applicant: Fritz Meininger ,  Joachim W. Otten, deceased ,  by Ursla Otten, heir ,  by Anna G. Rudolph, heir

Inventor： Fritz Meininger ,  Joachim W. Otten, deceased ,  by Ursla Otten, heir ,  by Anna G. Rudolph, heir

IPC: C09B62/505 ,  C07D251/50 ,  C09B62/44

CPC classification number: C09B62/4409

Abstract: Water-soluble anthraquinone compounds of the formula (1) ##STR1## wherein M is a hydrogen atom or the equivalent of a metal, such as in particular sodium or potassium, R is a hydrogen atom, a halogen atom, the methyl, ethyl, methoxy, ethoxy or carboxy group, and X is the vinyl group, a .beta.-thiosulfatoethyl, .beta.-sulfatoethyl or the .beta.-chloroethyl group. These compounds may be prepared in a manner know by itself by reacting an anthraquinone compound of the formula (2) ##STR2## wherein M is defined as above, with an equimolar quantity of cyanuric chloride and an amine of the formula (4) ##STR3## wherein R and X are defined as above, or by reacting said anthraquinone compound of the formula (2) with a compound of the formula (5) ##STR4## wherein R and X are defined as above. The new compounds of the formula (1) are valuable dyestuffs having fiber-reactive properties. When applied to materials containing hydroxy and/or carbonamide groups, preferably fiber materials, these dyestuffs yield strong and fast dyeings and prints or high tinctorial strength; for example, they are particularly suitable for dyeing (and printing) cellulose fiber materials and wool having an anti-felt or a felt-reducing finish.

Abstract translation: 式（1）的水溶性蒽醌化合物其中M为氢原子或金属当量，特别是钠或钾，R为氢原子，卤素原子，甲基 乙基，甲氧基，乙氧基或羧基，X是乙烯基，β-硫代硫代乙基，β-磺基乙基或β-氯乙基。 这些化合物可以通过使式（2）的蒽醌化合物（2）其中M如上所定义的蒽醌化合物与等摩尔量的氰尿酰氯和式（4）的胺反应而自己已知的方式制备 （4）其中R和X如上定义，或通过使式（2）的所述蒽醌化合物与式（5）化合物反应其中R和X定义为 以上。 式（1）的新化合物是具有纤维反应性质的有价值的染料。 当应用于含有羟基和/或碳酰胺基团的材料时，优选纤维材料，这些染料产生强烈和快速的染色和印花或高着色强度; 例如，它们特别适合用于染色（和印花）纤维素纤维材料和具有抗毛毡或毛毡减少处理的羊毛。

公开(公告)号：US4372892A

公开(公告)日：1983-02-08

申请号：US276807

申请日：1981-06-24

Applicant: Hermann Fuchs ,  Gustav Kapaun ,  Fritz Meininger

Inventor： Hermann Fuchs ,  Gustav Kapaun ,  Fritz Meininger

IPC: C09B62/503 ,  C07C141/00 ,  C07C143/58

CPC classification number: C09B62/503

Abstract: New compounds had been found which correspond to the formula ##STR1## as well as processes for preparing them by sulfonation of 3.beta.-sulfato- or 3-.beta.-hydroxyethylsulfonyl - aminobenzene. The novel compounds are valuable intermediary products for the preparation of azo fibre-reactive dyestuffs which have very good dyeing properties and a high fibre-reactivity yielding dyeings of excellent fastnesses, especially to light and wet processing.

Abstract translation: 已经发现了新的化合物，其对应于式“IMAGE”，以及通过磺化3β-磺基 - 或3-β-羟基乙基磺酰基 - 氨基苯制备它们的方法。 该新型化合物是制备偶氮纤维活性染料的有价值的中间产品，它们具有非常好的染色性能和高纤维反应性的染色，具有优异的牢度，尤其适用于轻和湿加工。

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。

公开(公告)号：US4134887A

公开(公告)日：1979-01-16

申请号：US852043

申请日：1977-11-16

Applicant: Hermann Fuchs ,  Gustav Kapaun ,  Fritz Meininger

Inventor： Hermann Fuchs ,  Gustav Kapaun ,  Fritz Meininger

IPC: C09B62/51 ,  C09B29/08 ,  D06P1/384 ,  D06P3/10 ,  D06P3/66

CPC classification number: C09B62/51

Abstract: Fiber-reactive azo dyestuffs are obtained by diazotizing an amine of the formula ##STR1## in which Z stands for--CH.sub.2 -CH.sub.2 --A or--CH.dbd.CH.sub.2in which A is N,N-dialkylamino with 1 to 4 carbon atoms in each alkyl moiety or is chlorine, bromine, sulfato, thiosulfato, phosphato and acetoxy it with an azo component of the formulaH--B,in which B is ##STR2## wherein R is hydrogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, acetylamino, chlorine or bromine, R.sub.1 is hydrogen or alkyl with 1 to 4 carbon atoms unsubstituted or substituted by hydroxy or cyano, and R.sub.2 is lower alkyl with 1 to 4 carbon atoms unsubstituted or substituted by hydroxy or cyano, or is acetyl or benozyl. The new dyestuffs are especially suitable for dyeing and printing fiber materials, such as silk, wool, synthetic polyamide or polyurethane, and above all, native and regenerative cellulose. They possess a very high fiber reactivity so that they fix on the fiber material very rapidly even at low temperatures and are thus very suitable in continuous dyeing processes.

Abstract translation: 纤维反应性偶氮染料是通过重氮化式为“IMAGE”的胺，其中Z代表-CH 2 -CH 2 -A或-CH = CH 2，其中A是N，每个具有1至4个碳原子的N-二烷基氨基 烷基部分或是氯，溴，硫酸根，硫代硫酸根，磷酸根和乙酰氧基，其与式HB的偶氮成分反应，其中B为其中R为氢，具有1至4个碳原子的烷基，具有1至4个碳原子的烷氧基 碳原子，乙酰氨基，氯或溴，R 1是氢或未被取代或被羟基或氰基取代的具有1至4个碳原子的烷基，R 2是未被取代或被羟基或氰基取代的具有1至4个碳原子的低级烷基，或者是乙酰基 或Benozyl。 新型染料特别适用于丝，羊毛，合成聚酰胺或聚氨酯等染色和印花纤维材料，尤其是天然纤维素和再生纤维素。 它们具有非常高的纤维反应性，使得即使在低温下它们也非常迅速地固定在纤维材料上，因此非常适合于连续染色过程。

公开(公告)号：US4066638A

公开(公告)日：1978-01-03

申请号：US514994

申请日：1974-10-15

Applicant: Hermann Fuchs ,  Gustav Kapaun ,  Fritz Meininger

Inventor： Hermann Fuchs ,  Gustav Kapaun ,  Fritz Meininger

IPC: C09B62/51 ,  C09B62/74 ,  D06P1/384 ,  D06P3/10 ,  D06P3/66

CPC classification number: C09B62/51

Abstract: Fiber-reactive azo dyestuffs are obtained by diazotizng an amine of the formula ##STR1## in which Z stands for--CH.sub.2 --CH.sub.2 --A or--CH.dbd.CH.sub.2in which A is N,N-dialkylamino with 1 to 4 carbon atoms in each alkyl moiety or is the radical of a mono- or poly-basic acid capable of being split off by an alkaline agent and coupling it with an azo component of the formulaH-B,in which B is aniline, naphthol, naphthylamine, aminonaphthol, pyridone, aminopyridine, 1-phenyl-4-aminopyrazole or 1-phenyl-5-pyrazolone, unsubstituted or substituted on the aromatic and/or heterocyclic moieties by one to four groups selected from alkyl, alkoxy, oxalkyl, cyanoalkyl, aminoalkyl or alkoxyalkyl with 1 to 6 carbon atoms in each alkyl and alkoxy moiety, chlorine and bromine, sulfonic acid, vinylsulfonyl, carboxyl, acylamino and arylamino groups.

公开(公告)号：US3939141A

公开(公告)日：1976-02-17

申请号：US430485

申请日：1974-01-03

Applicant: Fritz Meininger ,  Reinhard Hahnle

Inventor： Fritz Meininger ,  Reinhard Hahnle

IPC: C09B62/515 ,  C09B45/18 ,  C09B62/44 ,  C09B62/74 ,  C09B62/82

CPC classification number: C09B62/515

Abstract: Copper containing monoazo dyestuffs of the general formula ##SPC1##Wherein X is-- SO.sub.2 -- CH.sub.2 -- CH.sub.2 -- Z or-- SO.sub.2 -- CH = CH.sub.2in which Z is hydroxy or an inorganic or organic radical capable of being split off by alkaline agents. The said dyestuffs are easily soluble in water in the form of their alkali metal salts giving blue solutions which may be used for the dyeing or printing of nitrogen containing fibrous materials, materials containing hydroxyl groups or modified polyacrylonitrile fibrous materials, the dyeings obtained on wool or cellulose fibres being distinguished by high tinctorial strength and good fastness properties in general, and in particular to light, to wet processing, to weather, to chlorinated water and to hypochlorite.

Abstract translation: 具有通式的含铜单偶氮染料WHEREIN X是-SO 2 -CH 2 -CH 2 - Z或-SO 2 -CH = CH 2，其中Z是羟基或能够被碱性试剂分解的无机或有机基团。 所述染料以其碱金属盐的形式易溶于水，得到蓝色溶液，其可用于含氮纤维材料，含羟基或改性聚丙烯腈纤维材料的材料的染色或印刷，羊毛或 纤维素纤维通常具有高的着色强度和良好的坚牢度特性，特别是对于湿处理，耐候性，耐氯化水和次氯酸盐的区别。