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1. 发明授权

US4515598A Process for dyeing and printing fiber materials containing hydroxy and/or carbonamide groups with reactive dye containing both vinyl sulphonyl and fluoro-triazinyl groups 失效
标题翻译：含有羟基和/或碳酰胺基团的含有乙烯基磺酰基和氟 - 三嗪基的活性染料的纤维材料的染色和印花方法
公开(公告)号：US4515598A
公开(公告)日：1985-05-07
申请号：US550727
申请日：1983-11-10
申请人： Fritz Meininger , Joachim W. Otten, deceased , by Ursula Otten, heir , by Anna G. Rudolph nee Otten, heir
发明人： Fritz Meininger , Joachim W. Otten, deceased , by Ursula Otten, heir , by Anna G. Rudolph nee Otten, heir
IPC分类号： C09B62/503 , C09B62/44 , C09B62/507 , D06P1/38 , D06P1/384 , C09B62/04 , D06P3/66
CPC分类号： C09B62/4403 , D06P1/38 , Y10S8/917 , Y10S8/918 , Y10S8/924
摘要： A process for dyeing or printing fiber materials containing hydroxy and/or carbonamide groups, in which process a fiber-reactive, water-soluble dyestuff of the type defined below is applied to the fiber material and is then fixed on the fiber material at an ordinary or elevated temperature, if appropriate in the presence of agents having an alkaline reaction. This water-soluble dyestuff, which contains at least one sulfonic acid group, contains one or more groupings belonging to the group comprising the formulae (1a), (1b) and (1c)--SO.sub.2 --CH.dbd.CH.sub.2 (1a)--SO.sub.2 --CH.sub.2 --CH.sub.2 --Hal (1b)--SO.sub.2 --CH.sub.2 --CH.sub.2 --A (1c)(in which Hal represents a halogen atom and A represents the acyloxy radical of a monobasic or polybasic acid) and also contains, linked to it, a 6-fluoro-1,3,5-triazin-2-ylamino radical, this monofluorotriazinylamino radical containing, in the 4-position, a substituent which is not an N-phenylamino or N-naphthylamino substituent having a group belonging to the above-mentioned formulae (1) attached to the optionally substituted phenyl radical or optionally substituted naphthyl radical, and is also not an amino substituent containing an azo group. Dyestuffs of this type can belong to a very wide variety of classes of dyestuffs and can be both metal-free dyestuffs and metal complex dyestuffs. With the aid of these dyestuffs and using alkaline agents, this dyeing process produces deep dyeings and prints which have good fastness properties on these fiber materials, even at low temperatures.
摘要翻译：一种用于染色或印刷含有羟基和/或碳酰胺基团的纤维材料的方法，其中将下文定义的纤维反应性水溶性染料施用于纤维材料，然后以普通的方式固定在纤维材料上或升高的温度，如果适当，在具有碱性反应的试剂的存在下。这种含有至少一个磺酸基的水溶性染料含有属于由式（1a），（1b）和（1c）组成的基团的一个或多个基团-SO 2 -CH = CH 2（1a）-SO 2 - CH 2 -CH 2 - Hal（1b）-SO 2 -CH 2 -CH 2 -A（1c）（其中Hal表示卤素原子，A表示一元酸或多元酸的酰氧基），并且还含有6个 - 氟-1,3,5-三嗪-2-基氨基，该单氟三嗪基氨基在4-位含有不是具有属于上述的基团的N-苯基氨基或N-萘基氨基取代基的取代基连接到任选取代的苯基或任选取代的萘基的式（1），并且也不是含有偶氮基的氨基取代基。这种类型的染料可以属于各种各样的染料，并且可以是无金属染料和金属络合染料。借助这些染料和使用碱性剂，这种染色方法即使在低温下也能在这些纤维材料上产生深色染色和印花，这些染色和印花具有良好的坚牢度。

2. 发明授权

US4622390A Water-soluble disazo compounds containing an amino naphthol-disulfonic acid moiety as a coupling component and fibre-reactive groups 失效
标题翻译：含有氨基萘酚 - 二磺酸部分作为偶联成分的水溶性双偶氮化合物和纤维反应性基团
公开(公告)号：US4622390A
公开(公告)日：1986-11-11
申请号：US774171
申请日：1985-09-09
申请人： Fritz Meininger , Ernst Hoyer , Joachim W. Otten, deceased , by Ursula Otten, heir , by Anna G. Rudolph nee Otten, heir , Rudolf Fass
发明人： Fritz Meininger , Ernst Hoyer , Joachim W. Otten, deceased , by Ursula Otten, heir , by Anna G. Rudolph nee Otten, heir , Rudolf Fass
IPC分类号： C09B62/513 , C09B62/09 , C09B62/44 , D06P1/38 , C09B62/453 , C09B62/533 , D06P1/382
CPC分类号： C09B62/09 , C09B62/4415
摘要： Water-soluble disazo dyestuffs of the formula ##STR1## which contain a 1-amino-8-naphthol-3,6- or -4,6-disulfonic acid moiety as a bivalent coupling component and which contain diazo components with fibre-reactive groups characterized by the inclusion of one or two chloro-triazinyl groups and one or two of the six groups defined by the substituent Z, namely, ##STR2## each of which are connected to the benzene moiety of the diazo component; the chloro-triazinyl group is further substituted by a substituted or unsubstituted phenylamino or substituted or unsubstituted naphthylamino group, a substitutent of which may be one of the six groups defined by the Z substituent; if there is only one chloro-triazinyl group in the compound, then the diazo component is also substituted by one of the Z substituents; these compounds are dyestuffs which exhibit a good fixation degree of the dyestuffs in fabrics.
摘要翻译：含有作为二价偶联组分的1-氨基-8-萘酚-3,6-或-4,6-二磺酸部分并含有具有纤维反应性基团的重氮组分的式“IMAGE”的水溶性双偶氮染料其特征在于包含一个或两个氯 - 三嗪基和由取代基Z限定的六个基团中的一个或两个，即，＆lt; IMAGE＆gt; CH2SO2CH2CH2OSO3H; SO2CHCH2; + TR＆lt; IMAGE＆gt;各自与重氮组分的苯部分相连; 氯代三嗪基进一步被取代或未取代的苯基氨基或取代或未取代的萘基氨基取代，其取代基可以是由Z取代基限定的六个基团之一; 如果化合物中只有一个氯三嗪基，则重氮组分也被Z取代基之一取代; 这些化合物是在织物中表现出良好的染料固着度的染料。

3. 发明授权

US4649193A Water-soluble dyestuffs containing fibre-reactive groups of the vinylsulfone series and the fluoro-s-triazinyl-amino series 失效
标题翻译：含有乙烯基砜系列的纤维反应性基团和氟代-s-三嗪基 - 氨基系列的水溶性染料
公开(公告)号：US4649193A
公开(公告)日：1987-03-10
申请号：US519211
申请日：1983-08-01
申请人： Fritz Meininger , Joachim W. Otten, deceased , by Ursula Otten, heir , by Anna G. Rudolph nee Otten, heir
发明人： Fritz Meininger , Joachim W. Otten, deceased , by Ursula Otten, heir , by Anna G. Rudolph nee Otten, heir
IPC分类号： C09B62/503 , C09B62/44 , D06P1/384 , C09B62/06 , C09B62/085 , C09B62/095 , C09B62/10
CPC分类号： C09B62/4403
摘要： Water-soluble fibre-reactive dyestuffs containing one or two fibre-reactive groups of the vinylsulfone series and one or two fibre-reactive groups of the fluoro-s-triazinyl-amino series. These dyestuffs can be applied on fibre materials containing hydroxy and/or carbonamide groups by known application and fixation techniques for fibre-reactive dyes to yield deep and fast dyeings on these materials.
摘要翻译：含有一个或两个乙烯基砜系列的纤维反应性基团和氟代-s-三嗪基 - 氨基系列的一个或两个纤维反应性基团的水溶性纤维活性染料。这些染料可以通过纤维活性染料的已知应用和固色技术应用于含有羟基和/或碳酰胺基团的纤维材料上，以在这些材料上产生深色和快速的染色。

4. 发明授权

US4442288A Anthraquinone compounds 失效
标题翻译：蒽醌化合物
公开(公告)号：US4442288A
公开(公告)日：1984-04-10
申请号：US373789
申请日：1982-04-30
申请人： Fritz Meininger , Joachim W. Otten, deceased , by Ursla Otten, heir , by Anna G. Rudolph, heir
发明人： Fritz Meininger , Joachim W. Otten, deceased , by Ursla Otten, heir , by Anna G. Rudolph, heir
IPC分类号： C09B62/505 , C07D251/50 , C09B62/44
CPC分类号： C09B62/4409
摘要： 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.
摘要翻译：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。

5. 发明授权

US4045428A Water-soluble reactive naphthylazonaphthyl dyestuffs 失效
标题翻译：水溶性活性萘基萘基染料
公开(公告)号：US4045428A
公开(公告)日：1977-08-30
申请号：US603914
申请日：1975-08-12
申请人： Fritz Meininger , Klaus Hunger , Hartmut Springer
发明人： Fritz Meininger , Klaus Hunger , Hartmut Springer
IPC分类号： C09B62/51 , C09B62/50 , C09B62/74 , D06P1/06 , D06P1/38
CPC分类号： C09B62/51
摘要： A water-soluble monoazo-dyestuff of the formula (1) ##STR1## in which X represents --CH=CH.sub.2 or --CH.sub.2 --CH.sub.2 --Z, the radical Z stands for hydroxyl, sulfato, chlorine, bromine, lower alkyl-sulfonyloxy, lower alkyl-sulfonylamino, phenyl-sulfonyloxy, lower alkyl-phenyl-sulfonyloxy, phenyl-sulfonylamino, lower alkyloyloxy, monosulfobenzoyloxy, phenoxy, di-(lower alkyl)-amino, tri-(lower alkyl)-ammonium, thiosulfato or phosphato, and A is a radical of a coupling component of the aminobenzene, hydroxybenzene amino-naphthalene, hydroxynaphthalene, N-naphthyl- or N-phenyl-amino-pyrazole, N-naphthyl- or N-phenyl-pyrazolone or of the acetoacetanilide series, the coupling component containing at least one water-solubilizing group, and a process for preparing these dyestuffs which are very suitable for the dyeing and printing of native and synthetic carbonamide-groups containing and native, regenerated or synthetic hydroxy-groups containing material, and yield, especially on cellulose fibrous materials in the presence of alkaline agents dyeings and prints of good to very good fastnesses to light and to wet-processing and of good stability to alkalis. The novel dyestuffs also have a very good color-build-up and yield dyeings and prints of high tinetorial strength.
摘要翻译：式（1）（1）＆lt; IMAGE＆gt;的水溶性单偶氮染料，其中X表示-CH = CH 2或-CH 2 -CH 2 -Z，基团Z代表羟基，硫酸根合，氯，溴，低级烷基 - 磺酰氧基，低级烷基 - 磺酰基氨基，苯基 - 磺酰氧基，低级烷基 - 苯基 - 磺酰氧基，苯基 - 磺酰基氨基，低级烷氧基，单磺酰基苯甲酰氧基，苯氧基，二 - （低级烷基） - 氨基，三 - （低级烷基） - 铵，磷酸盐和A是氨基苯，羟基苯氨基萘，羟基萘，N-萘基或N-苯基 - 氨基 - 吡唑，N-萘基或N-苯基 - 吡唑啉酮或乙酰乙酰苯胺系列的偶联组分的基团，含有至少一种水溶性基团的偶联组分和这些染料的制备方法非常适用于染色和印刷含天然和合成的含碳酰胺基团和天然的，再生的或合成的含羟基的材料，以及产率，特别是纤维素纤维材料在碱性染料和印刷品存在下，具有良好至非常好的耐光牢度和湿法加工性能以及对碱的稳定性。新颖的染料也具有非常好的色素积累和产生高的色谱强度的染色和印花。

6. 发明授权

US4485041A Water-soluble metal free or copper triazino-bis-[hydroxy-naphthylamino]-disazo dyestuffs containing fiber reactive groups, and a process for dyeing or printing cellulose fibers 失效
标题翻译：含有纤维反应性基团的水溶性无金属或铜三嗪基 - 双 - [羟基 - 萘基氨基] - 二偶氮染料，以及染色或印刷纤维素纤维的方法
公开(公告)号：US4485041A
公开(公告)日：1984-11-27
申请号：US234966
申请日：1981-02-17
申请人： Ernst Hoyer , Fritz Meininger , Rudolf Fass
发明人： Ernst Hoyer , Fritz Meininger , Rudolf Fass
IPC分类号： C09B62/513 , C09B62/44 , C09B62/515 , D06P3/10 , D06P3/66 , C09B62/09 , C09B62/095 , C09B62/533 , C09B62/535
CPC分类号： C09B62/4411
摘要： 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.
摘要翻译：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。

7. 发明授权

US4378312A Water-soluble azo dyestuffs 失效
公开(公告)号：US4378312A
公开(公告)日：1983-03-29
申请号：US219499
申请日：1980-12-23
申请人： Ernst Hoyer , Fritz Meininger , Rudolf Fass
发明人： Ernst Hoyer , Fritz Meininger , Rudolf Fass
IPC分类号： C09B62/44 , C09B62/513 , C09B62/515 , D06P3/66 , C09B33/02 , C09B33/06
CPC分类号： C09B62/4411 , C09B62/513 , Y10S534/01
摘要： 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.

8. 发明授权

US4088441A Dyestuff composition for the dyeing or printing of cellulose fiber materials 失效
标题翻译：用于染色或印花纤维素纤维材料的染料组合物
公开(公告)号：US4088441A
公开(公告)日：1978-05-09
申请号：US713589
申请日：1976-08-11
申请人： Fritz Meininger , Walter Noll , Arno Spange
发明人： Fritz Meininger , Walter Noll , Arno Spange
IPC分类号： C09B67/24 , D06P1/48 , D06P1/62 , D06P3/66 , D06P1/38
CPC分类号： D06P3/66 , C09B67/0072 , D06P1/48 , D06P1/621
摘要： A dyestuff composition for the dyeing or printing of natural or regenerated cellulose fiber materials, consisting of 20 to 70 percent by weight of C.I. Reactive Blue 19 (sodium salt), anthraquinone-2-sulfonic acid (sodium salt), a condensation product of naphthalene-sulfonic acid with formaldehyde (sodium salt), a condensed phosphate (sodium salt), preferably sodiumhexametaphosphate or penta-sodiumtriphosphate, and a dust preventing agent.
摘要翻译：一种用于染色或印刷天然或再生纤维素纤维材料的染料组合物，由20至70重量％的C.I. 活性蓝19（钠盐），蒽醌-2-磺酸（钠盐），萘磺酸与甲醛（钠盐）的缩合产物，缩合磷酸盐（钠盐），优选六偏磷酸钠或五 - 三磷酸钠的缩合产物，以及防尘剂。

9. 发明授权

US4033980A Phthalocyanine dyestuffs and process for preparing them 失效
标题翻译：酞菁染料及其制备方法
公开(公告)号：US4033980A
公开(公告)日：1977-07-05
申请号：US281790
申请日：1972-08-18
申请人： Fritz Meininger , Klaus Hunger , Hartmut Springer
发明人： Fritz Meininger , Klaus Hunger , Hartmut Springer
IPC分类号： C09B47/26 , C09B62/457 , C09B47/04
CPC分类号： C09B62/457 , C09B47/26
摘要： A water-soluble phthalocyanine dyestuff of the formula ##STR1## IN WHICH Pc represents copper phthalocyanine, nickel phthalocyanine or cobalt phthalocyanine, R.sub.3 represents lower alkyl, B represents --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --NH--, ##STR2## A represents phenylene or phenylene substituted by lower alkyl, lower alkoxy, carboxyl, hydroxyl, sulfo, nitro, chlorine or bromine, or naphthylene, X represents --CH.sub.2 -- or ##STR3## R.sub.1 and R.sub.2 each stand for hydrogen, lower alkyl, hydroxyethyl, sulfoethyl, carboxyethyl, benzyl, phenyl, carboxyphenylene or sulfophenylene, or together with the nitrogen atom piperidyl or morpholyl, n and m each represent 0 or 1, a, b and c each stand for a number from 1 to 4, the sum of a, b and c being at most 6, said dyestuff being suitable for the dyeing or printing of leather or textile materials consisting of native or regenerated cellulose, silk or polyamides, the dyeings and prints obtained on said materials being distinguished by deep tints and very good fastness properties to light and to wetting.
摘要翻译：下式的水溶性酞菁染料Pc表示铜酞菁，镍酞菁或酞菁酞菁，R3表示低级烷基，B表示-CH2-CH2-，-CH2-CH2-NH-， + R A表示被低级烷基，低级烷氧基，羧基，羟基，磺基，硝基，氯或溴取代的亚苯基或亚苯基，或亚萘基，X表示-CH 2 - 或R 1，R 2各自代表氢，低级烷基，羟乙基，磺乙基，羧乙基，苄基，苯基，羧基亚苯基或磺基亚苯基，或与氮原子一起为哌啶基或吗啉基，n和m各自表示0或1，a，b和c各自表示1至4的数， a，b和c的总和最多为6，所述染料适用于由天然或再生纤维素，丝或聚酰胺组成的皮革或纺织材料的染色或印花，所述材料上得到的染色和印刷品由深度色泽和非常好的牢度性能要光亮和润湿。

10. 发明授权

US4000966A Dyeing cellulose with aminonaphthyl azobenzene vinyl type reactive dyes 失效
标题翻译：含氨基苯甲酸乙烯酯类型反应性染料的染色纤维素
公开(公告)号：US4000966A
公开(公告)日：1977-01-04
申请号：US407205
申请日：1973-10-17
申请人： Fritz Meininger , Ludwig Schlafer , Maria Kallay
发明人： Fritz Meininger , Ludwig Schlafer , Maria Kallay
IPC分类号： C09B62/515 , D06P3/66 , D06P3/00
CPC分类号： D06P3/666 , C09B62/515 , D06P3/66 , Y10S8/918
摘要： Process for the manufacture of fast dyeings or prints on fibrous materials containing cellulose wherein metal containing reactive dyestuffs of the general formula ##SPC1##In whichM represents a cobalt or chromium atom,R represents a hydrogen atom, a halogen atom, a nitro, acetyl-amino,amino, or lower alkyl or alkoxy group containing from 1 to 4 carbon atoms,R' represents a hydrogen atom or an alkyl radical containing from 1 to 4 carbon atoms,R" represents a hydrogen atom, an alkyl radical containing from 1 to 4 carbon atoms or a phenyl rest which may be substituted andn is zero or the integer 1 andX represents the vinyl group or the radical of formula --CH.sub.2 --CH.sub.2 --Y in which Y represents a halogen atom, a sulfuric acid ester, thiosulfuric acid ester, phosphoric acid ester, dimethyl amino or diethyl amino group,Are applied onto the said fibrous materials and are fixed at a temperature within the range of from 0.degree. to 200.degree. C, preferably from 15.degree. and 150.degree. C by means of alkaline agents and heating, and in the case X being CH.sub.2 =CH-- the alkaline agent is not necessary, the said dyestuffs giving navy-blue and grey to black-brown printing designs and dyeings of very good fastness properties as to washing and to boiling soda and being distinguished by the constancy of their shade in the various dyeing and printing processes which have previously been proposed.

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