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：US4088441A

公开(公告)日：1978-05-09

申请号：US713589

申请日：1976-08-11

Applicant: Fritz Meininger ,  Walter Noll ,  Arno Spange

Inventor： Fritz Meininger ,  Walter Noll ,  Arno Spange

IPC: C09B67/24 ,  D06P1/48 ,  D06P1/62 ,  D06P3/66 ,  D06P1/38

CPC classification number: D06P3/66 ,  C09B67/0072 ,  D06P1/48 ,  D06P1/621

Abstract: 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.

Abstract translation: 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。

公开(公告)号：US4000966A

公开(公告)日：1977-01-04

申请号：US407205

申请日：1973-10-17

Applicant: Fritz Meininger ,  Ludwig Schlafer ,  Maria Kallay

Inventor： Fritz Meininger ,  Ludwig Schlafer ,  Maria Kallay

IPC: C09B62/515 ,  D06P3/66 ,  D06P3/00

CPC classification number: D06P3/666 ,  C09B62/515 ,  D06P3/66 ,  Y10S8/918

Abstract: 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.

公开(公告)号：US4906738A

公开(公告)日：1990-03-06

申请号：US722759

申请日：1985-04-15

Applicant: Folker Kohlhaas ,  Fritz Meininger ,  Hans H. Steuernagel

Inventor： Folker Kohlhaas ,  Fritz Meininger ,  Hans H. Steuernagel

IPC: C09B62/51 ,  C09B62/44 ,  D06P1/382 ,  D06P1/384

CPC classification number: C09B62/4413

Abstract: 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.

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：US4229171A

公开(公告)日：1980-10-21

申请号：US948907

申请日：1978-10-05

Applicant: Fritz Meininger

Inventor： Fritz Meininger

IPC: C09B62/517 ,  C09B47/26 ,  C09B62/443 ,  C09B67/12 ,  C09B67/22 ,  D06P1/38 ,  D06P3/32 ,  C09B62/66 ,  C09B62/68 ,  C09B62/74 ,  C09B62/76

CPC classification number: C09B67/0041 ,  C09B47/26 ,  C09B62/443 ,  C09B67/0045 ,  Y10S534/01

Abstract: A fiber-reactive dyestuff mixture is obtained by reacting a phthalocyanine sulfochloride with an aromatic amine having a fiber-reactive group selected from vinyl sulfonyl, .beta.-sulfatoethyl-sulfonyl and .beta.-hydroxyethyl-sulfonyl groups, diazotizing unreacted amine in the resulting mixture and reacting the diazo compound in the mixture with a conventional coupling component to form a mixture of phthalocyanine and azo dyestuffs.

Abstract translation: 通过使酞菁磺酰氯与具有选自乙烯基磺酰基，β-磺基乙基磺酰基和β-羟基乙基磺酰基的纤维反应性基团的芳族胺反应，在所得混合物中重氮化未反应的胺，使反应产生的混合物反应，得到纤维活性染料混合物， 该混合物中的重氮化合物与常规的偶联组分形成酞菁和偶氮染料的混合物。

公开(公告)号：US4074967A

公开(公告)日：1978-02-21

申请号：US526389

申请日：1974-11-22

Applicant: Hermann Fuchs ,  Gustav Kapaun ,  Fritz Meininger

Inventor： Hermann Fuchs ,  Gustav Kapaun ,  Fritz Meininger

IPC: D06P3/04 ,  C09B11/26 ,  C09B67/24 ,  D06P3/06 ,  D06P3/26 ,  D06P3/32 ,  C09B11/00 ,  D06P3/24

CPC classification number: D06P3/32 ,  C09B11/26 ,  C09B67/0072 ,  D06P3/06 ,  Y10S8/917 ,  Y10S8/924

Abstract: A highly water-soluble composition for the dyeing or printing of native or synthetic polyamide fibres consisting essentially of (a) 10 to 99 parts by weight of at least one dyestuff ##STR1## IN WHICH X represents hydroxy, methyl, ethyl, methoxy or ethoxy, and Y represents hydrogen or methyl, and (b) 0.5 to 90 parts by weight of an auxiliary agent of the group consisting of a polyglycol of an average molecular weight from 3000 to 20 000, a polyglycolether (containing 15 to 30 ether groups) of a fatty alcohol of 8 to 20 carbon atoms, an alkali metal salt of a dialkylnaphthalene sulfonic acid (alkyl C.sub.1 -C.sub.6), a methyltauride of a saturated or unsatruated fatty acid of 8 to 20 carbon atoms, and an isethionate of a saturated or unsaturated fatty acid of 8 to 20 cabron atoms, and mixtures thereof, said composition being also suitable for the dyeing or printing of the said polyamide fibres in deep shades.

Abstract translation: 用于染色或印刷天然或合成聚酰胺纤维的高度水溶性组合物，其基本上由（a）10至99重量份的至少一种染料组成，其中X表示羟基，甲基，乙基，甲氧基或乙氧基 ，Y表示氢或甲基，（b）0.5〜90重量份的平均分子量为3000〜20000的聚乙二醇的辅助剂，聚乙二醇醚（含有15〜30个醚基） 的碳原子数为8〜20的脂肪醇，二烷基萘磺酸（烷基C1-C6）的碱金属盐，碳原子数为8〜20的饱和或不饱和脂肪酸的甲基牛磺酸和饱和或不饱和脂肪酸的羟乙基磺酸盐， 8至20个卡培酮原子的不饱和脂肪酸及其混合物，所述组合物也适用于以深色调染色或印刷所述聚酰胺纤维。

公开(公告)号：US4036825A

公开(公告)日：1977-07-19

申请号：US730428

申请日：1976-10-07

Applicant: Hermann Fuchs ,  Fritz Meininger

Inventor： Hermann Fuchs ,  Fritz Meininger

IPC: C09B62/51 ,  C09B29/06 ,  C09B29/26 ,  C09B29/30 ,  C09B29/38

CPC classification number: C09B62/51

Abstract: Fiber-reactive monoazo dyestuffs which, in form of free acids, correspond to the general formula ##STR1## in which Z represents one of the groupings--CH.sub.2 --CH.sub.2 --OSO.sub.3 Hor--CH=CH.sub.2a stands for benzene, naphthalene or pyrazole unsubstituted or substituted by alkyl, alkoxy or by a phenyl group which is unsubstituted or may be substituted by alkyl, alkoxy, hydroxy, cyano, nitro, sulfonic acid, sulfonic acid amide, carboxylic acid amide, chlorine, bromine, carboxylic acid, acetylamino, benzoylamino, trifluoromethyl, carbalkoxy, B-sulfatoethylsulfonyl or vinylsulfonyl, and wherein, if A represents a benzene or naphthalene radical the azo group and the amino group of the formula --NR.sub.1 R.sub.2 standing in ortho or para position to each other, and if A is pyrazole, the group --NR.sub.1 R.sub.2 is standing in 5-position and the azo group in 4-position of the pyrazole, R.sub.1 and R.sub.2 are different or the same and each stand for hydrogen or alkyl which may be substituted by chlorine, hydroxy, cyano, alkanoyloxy, benzoyloxy, nitrobenzoyloxy, chlorobenzoyloxy, phenyl or phenyl substituted by alkyl, alkoxy, alkyl-sulfone, sulfonic acid, sulfonic acid amide, carboxylic acid amide, nitro, trifluoromethyl, chlorine or bromine, which are suitable for the dyeing and printing of native and regenerated cellulose fibers, but especially advantageous for dyeing or printing fibers or fabrics of nitrogen - containing fibers of native or synthetic origin.

Abstract translation: 以游离酸形式存在的纤维反应性单偶氮染料对应于通式“IMAGE”，其中Z代表一组-CH 2 -CH 2 OSO 3 H或-CH = CH 2 A代表未取代的苯，萘或吡唑， 羟基，氰基，硝基，磺酸，磺酸酰胺，羧酸酰胺，氯，溴，羧酸，乙酰氨基，苯甲酰基氨基，苯甲酰氨基， 三氟甲基，烷氧羰基，B-硫酸基乙基磺酰基或乙烯基磺酰基，并且其中如果A表示苯或萘基，则偶氮基和式-NR1R2的氨基彼此相邻或对位，如果A是吡唑，则 基团-NR1R2位于5位，吡唑R 1和R 2的4位的偶氮基不同或相同，各代表氢或可被氯，羟基，氰基，烷酰氧基，苯甲酰氧基取代的烷基 ，n 苯甲酰氧基，氯苯甲酰氧基，苯基或被烷基，烷氧基，烷基砜，磺酸，磺酸酰胺，羧酸酰胺，硝基，三氟甲基，氯或溴取代的苯基，适用于天然和再生纤维素纤维的染色和印花 ，但对于染色或印刷天然或合成来源的含氮纤维的纤维或织物特别有利。

公开(公告)号：US4029644A

公开(公告)日：1977-06-14

申请号：US629677

申请日：1975-11-06

Applicant: Fritz Meininger ,  Ludwig Schlafer

Inventor： Fritz Meininger ,  Ludwig Schlafer

IPC: C09B62/51 ,  C09B29/16

CPC classification number: C09B62/51

Abstract: A water-soluble monoazo-dyestuff of the formula ##STR1## WHEREIN R represents lower alkyl or lower alkoxy, R' represents hydrogen, lower alkyl or lower alkoxy, X represents --SO.sub.2 --CH.sub.2 --CH.sub.2 --OH, --SO.sub.2 --CH.sub.2 --CH.sub.2 --O--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 --S--SO.sub.3 H or --SO.sub.2 --CH.sub.2 --CH.sub.2 --N (lower alkyl).sub.2, and n stands for the integer 1, 2 or 3 said dyestuffs being suitable for the dyeing or printing of nitrogen containing native or synthetic fibrous materials and particularly of native or regenerated cellulose fibres with high tinctorial strength, the dyeings and prints obtained on the cellulose fibres being distinguished by considerable fastness properties to wear, to processing and to use. Padded or printed on cotton and fixed by different methods well known in the art, the novel dyestuffs yield prints or dyeings having the same clear shade that means they possess a very good constancy of shade in the use of different fixation processes. Used in printing processes they yield prints with sharp outlines.

Abstract translation: 下式的水溶性单偶氮染料，其中R表示低级烷基或低级烷氧基，R'表示氢，低级烷基或低级烷氧基，X表示-SO2-CH2-CH2-OH，-SO2-CH2-CH2 -O-SO3H，-SO2-CH2-CH2-O-PO3H2，-SO2-CH2-CH2-S-SO3H或-SO2-CH2-CH2-N（低级烷基）2，n代表整数1,2 或3种所述染料适用于含氮天然或合成纤维材料，特别是具有高着色强度的天然或再生纤维素纤维的染色或印刷，在纤维素纤维上获得的染色和印花的特征在于具有相当大的耐磨性， 加工和使用。 通过本领域众所周知的不同方法将棉花填充或印刷并固定，新颖的染料产生具有相同透明阴影的印花或染色，这意味着它们在使用不同的固定方法时具有非常好的恒定性。 用于印刷过程中，它们以锐利的轮廓产生印刷。

公开(公告)号：US3939140A

公开(公告)日：1976-02-17

申请号：US480206

申请日：1974-06-17

Applicant: Fritz Meininger ,  Hermann Fuchs

Inventor： Fritz Meininger ,  Hermann Fuchs

IPC: C09B45/01 ,  C09B45/16 ,  C09B45/06

CPC classification number: C09B45/01 ,  C09B45/16

Abstract: Process for preparing a dyestuff consisting essentially of only unsymmetrical 1:2-chromium complex azo dyestuffs by heating a mixture of o,o'-dihydroxy azo dyestuffs and o-carboxy-o'-hydroxy azo dyestuffs, both being free from sulfonic acid groups, with chromium-III chloride in an organic solvent at a temperature of 105.degree. to 120.degree.C until the portion of o,o'-dihydroxy azo dyestuff is completely metallized and completing the 1:2-chromium complex formation by adjusting the pH-value to 5.0-6.5, and heating at a temperature of 70.degree. to 90.degree.C.

Abstract translation: 用于制备基本上仅由不对称的1：2-铬络合偶氮染料组成的染料的方法，其通过加热o，o'-二羟基偶氮染料和邻羧基-O'-羟基偶氮染料的混合物，两者不含磺酸基团 用铬-III氯化物在有机溶剂中在105℃至120℃的温度下直至o，o'-二羟基偶氮染料的部分完全金属化，并通过调节pH值达到1:2-铬络合物形成， 值为5.0-6.5，在70〜90℃的温度下加热。