公开(公告)号：US4150046A

公开(公告)日：1979-04-17

申请号：US875886

申请日：1978-02-07

Applicant: Klaus Hunger ,  Edwin Baier

Inventor： Klaus Hunger ,  Edwin Baier

IPC: C07F1/00 ,  C09B55/00 ,  C07F1/08

CPC classification number: C09B55/002 ,  C07F1/005

Abstract: Compounds of the formula ##STR1## in which X is hydrogen, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro, trifluoromethyl or a group of the formula--COOY,wherein Y is hydrogen or alkyl of 1 to 5 carbon atoms, R.sup.1 and R.sup.2 are hydrogen or one of the substituents R.sup.1 and R.sup.2 is hydrogen and the other is --COOY, with the proviso that at least one of the substituents X, R.sup.1 and R.sup.2 is --COOY and that R.sup.2 is hydrogen or carboalkoxy of 2 to 6 carbon atoms if X is hydrogen,Are obtained by coppering the corresponding bishydroxy or phenol-anisole-compounds, are valuable pigments having clear and brilliant tints, a high heat-fastness and a high fastness to migration, especially overlacquering, to light and to weathering.

Abstract translation: 其中X为氢，氯，溴，1至4个碳原子的烷基，1至4个碳原子的烷氧基，硝基，三氟甲基或式-COOY基团，其中Y为氢 或1至5个碳原子的烷基，R 1和R 2是氢或取代基R 1和R 2之一是氢，另一个是-COOY，条件是至少一个取代基X，R 1和R 2是-COOY和 如果X是氢，则R2是氢或2至6个碳原子的烷氧基，通过加入相应的双羟基或酚 - 酚化合物得到，是具有清除和无定形倾向的有价值的颜料，高热量和高熔点 移动，特别是过度的，光照和天气的。

公开(公告)号：US4074053A

公开(公告)日：1978-02-14

申请号：US670997

申请日：1976-03-26

Applicant: Klaus Hunger ,  Theodor Papenfuhs

Inventor： Klaus Hunger ,  Theodor Papenfuhs

IPC: C09B55/00 ,  C07D235/26

CPC classification number: C09B55/00

Abstract: Aldehydes of a 2-hydroxy-naphthalene-3-carboxylic acid arylide of the general formula ##STR1## IN WHICH X represents a hydrogen, chlorine or bromine atom, and Ar represents a naphthyl group, a benzimidazolone, chlorobenzimidazolone, quinazolone, quinoxaline, phthalimide, phthalazine group or a phenyl group which may carry 1 to 3 lower alkyl, lower alkoxy, lower alkylsulfonyl, lower carboalkoxy, halogen, trifluoromethyl, nitro, cyano, lower alkanoylamino, benzoylamino, carboxamido or sulfoamido groups, and a process for their preparation wherein the corresponding 2-hydroxy-naphthalene-3-carboxylic acid arylide is reacted in a lower aliphatic carboxylic acid with hexamethylene tetramine and a mineral acid.These aldehydes are valuable intermediate products for the synthesis of optical brighteners, pharmaceuticals and, in particular, of azamethine pigments which are obtained by condensation of these aldehydes with suitable amines. The pigments thus obtained are distinguished by good fastness properties and are especially suitable for the printing of paper and the coloring of lacquers, varnishes and plastics.

Abstract translation: 其中X表示氢，氯或溴原子，且Ar表示萘基，苯并咪唑烷酮，氯苯并咪唑酮，喹唑啉酮，喹喔啉，邻苯二甲酰亚胺的2-羟基 - 萘-3-羧酸芳基化合物的醛 ，可以带有1-3个低级烷基，低级烷氧基，低级烷基磺酰基，低级烷氧羰基，卤素，三氟甲基，硝基，氰基，低级烷酰基氨基，苯甲酰氨基，甲酰胺基或磺酰氨基的苯肼基或苯基，及其制备方法 相应的2-羟基 - 萘-3-羧酸芳基化物在低级脂族羧酸与六亚甲基四胺和无机酸反应。

公开(公告)号：US4033980A

公开(公告)日：1977-07-05

申请号：US281790

申请日：1972-08-18

Applicant: Fritz Meininger ,  Klaus Hunger ,  Hartmut Springer

Inventor： Fritz Meininger ,  Klaus Hunger ,  Hartmut Springer

IPC: C09B47/26 ,  C09B62/457 ,  C09B47/04

CPC classification number: C09B62/457 ,  C09B47/26

Abstract: 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.

Abstract translation: 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。

公开(公告)号：US3966704A

公开(公告)日：1976-06-29

申请号：US409813

申请日：1973-10-26

Applicant: Fritz Meininger ,  Klaus Hunger ,  Hartmut Springer

Inventor： Fritz Meininger ,  Klaus Hunger ,  Hartmut Springer

IPC: C09B62/515 ,  C09B45/18 ,  C09B45/32 ,  D06P3/60

CPC classification number: C09B62/515

Abstract: New valuable metal complex compounds, preferably copper, nickel, chromium or cobalt complex compounds, of monoazo dyestuffs which in the metal-free form and in form of the free acid correspond to the general formula (1) ##SPC1##In which one A stands for the group of the formula (2)HO -- R -- N = -- (2)wherein HO--R-- represents the radical of a coupling component of the series of the acetoacetic acid arylamide, barbituric acid, pyrazolone or of naphthalene, the hydroxyl group of which is in a vicinal position with regard to the azo group, and the other A stands for a hydroxyl group, X for a vinyl group or for a group having the formula --CH.sub.2 --CH.sub.2 --Z, wherein Z represents the hydroxyl group or an organic or inorganic radical capable of being split off by an alkaline agent, n represents the number 1 or 2 and m a number of from 1 to 3, and processes to prepare them, said dyestuffs being suitable for the dyeing and printing of different materials, such as wool, silk, poly amide fiber materials or leather, especially of cellulose-containing materials such as cotton, regenerated cellulose and linen, yielding intense dyeings and prints of high tinctorial strength which exhibit good to very good fastnesses to light, wet processing, washing, perspiration, steaming, ironing and rubbing and are resistant to chemical solvents.

Abstract translation: 新的有价值的金属配合物化合物，优选铜，镍，铬或钴配位化合物，以无金属形式和游离酸形式的单偶氮染料对应于通式（1）。其中A代表基团 （2）HO-R-N = - （2）其中HO-R-表示一系列乙酰乙酸芳基酰胺，巴比妥酸，吡唑啉酮或萘的偶联组分的基团，其羟基 相对于偶氮基而言位于相邻位置，另一个A表示羟基，X表示乙烯基或具有式-CH 2 -CH 2 -Z的基团，其中Z表示羟基或有机基团 或能够被碱性试剂分解的无机基团，n表示数字1或2，马克数1〜3，制备方法，所述染料适用于不同材料的染色和印刷，例如 羊毛，丝绸，聚酰胺纤维材料或皮革 特别是含纤维素的材料如棉花，再生纤维素和亚麻，产生强烈的着色力和高着色强度的印花，表现出良好的非常好的耐光牢度，湿法加工，洗涤，出汗，蒸，熨烫和摩擦。 化学溶剂。

公开(公告)号：US4696675A

公开(公告)日：1987-09-29

申请号：US845623

申请日：1986-03-27

Applicant: Hasso Hertel ,  Klaus Hunger ,  Heinrich Frolich

Inventor： Hasso Hertel ,  Klaus Hunger ,  Heinrich Frolich

IPC: D06P1/12 ,  C09B35/14 ,  D06P3/68 ,  C09B35/02

CPC classification number: D06P3/68 ,  C09B35/14 ,  Y10S8/918

Abstract: Using the method of azoic dyeing, fast blue dyeings are obtained when the bis-diazotable diazo component used is a compound of the general formula (1) ##STR1## in which R is a straight-chain or branched alkyl group of 3 to 5 carbon atoms or a (C.sub.1 -C.sub.3)-alkoxy-(C.sub.2 -C.sub.4)-alkyl group having straight-chain and/or branched alkyl groups of in total 3 to 5 carbon atoms, and the coupling component used is a compound conforming to the general formula (2) ##STR2## in which Z stands for a hydrogen atom or a halogen atom or an alkoxy group of 1 to 4 carbon atoms and Aryl denotes a phenyl radical or a 1-naphthyl radical which can be substituted by 1, 2 or 3 substituents from the group consisting of halogen, nitro, alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, and the coupling reaction and dye formation on the fiber are carried out at a pH value between 4 and 10.

Abstract translation: 使用偶氮染色方法，当所用的双重氮偶氮重氮组分是通式（1）的化合物时，得到了快速的蓝色染色，其中R是3或3的直链或支链烷基 至5个碳原子或具有总共3至5个碳原子的具有直链和/或支链烷基的（C1-C3） - 烷氧基 - （C2-C4） - 烷基，所用的偶合组分是符合化合物 （2）其中Z表示氢原子或卤素原子或1〜4个碳原子的烷氧基，通式（2）表示苯基或1-萘基，可以是 被1,2或3个由卤素，硝基，1至4个碳原子的烷基和1至4个碳原子的烷氧基取代的取代基取代，纤维上的偶联反应和染料形成在pH值 在4到10之间。

公开(公告)号：US4504416A

公开(公告)日：1985-03-12

申请号：US256085

申请日：1981-04-21

Applicant: Klaus Hunger ,  Manfred Pesenacker

Inventor： Klaus Hunger ,  Manfred Pesenacker

IPC: C09B29/01 ,  C09B29/32 ,  C09B29/33

CPC classification number: C09B29/338 ,  C09B29/0003

Abstract: When diazotizing a p-amino-benzoic acid anilide, the anilide nucleus of which is substituted in its paraposition by carbamoyl, acetamino or chloro and coupling it onto 5-acetoacetylamino-benzimidazolone-(2) monoazo pigments are obtained having a high fastness to light, solvents, overlacquering and bleeding and a very high heat resistance.

Abstract translation: 当苯胺酰胺重氮化后，其酰胺基核被氨基甲酰基，乙酰氨基或氯代替，并将其偶联到5-乙酰乙酰氨基 - 苯并咪唑酮 - （2）单偶氮颜料上，具有高耐光牢度 溶剂，覆盖和渗出以及非常高的耐热性。

公开(公告)号：US4405793A

公开(公告)日：1983-09-20

申请号：US8394

申请日：1979-02-01

Applicant: Otto Fuchs ,  Klaus Hunger ,  Dieter Weber ,  Reinhard Zunker

Inventor： Otto Fuchs ,  Klaus Hunger ,  Dieter Weber ,  Reinhard Zunker

IPC: C07D271/10 ,  C07C243/38 ,  C07D271/107 ,  C09B35/34 ,  C08K5/23

CPC classification number: C07D271/107 ,  C07C243/38 ,  C09B35/34

Abstract: 2,5-Bis-(4'-aminophenyl)-1,3,4-oxadiazoles which are chlorinated in the phenyl nuclei are obtained by condensing hydrazine or a hydrazine yielding agent with equal or different chlorinated benzoic acids or acylating acid derivatives having in para-position to the acid group an amino group or a group capable of being transformed into the amino group, and, thereafter, effecting ring closure of the so-obtained bis-hydrazide to yield the oxadiazole. The products are bis-diazo components, especially for pigments having a very high tinctorial strength, clear and pure shades, a good fastness to light, to heat and to solvents.

Abstract translation: 在苯基核中氯化的2,5-双 - （4'-氨基苯基）-1,3,4-恶二唑通过将肼或肼产生试剂与相同或不同的氯化苯甲酸或酰化酸衍生物缩合而获得， 酸基的对位是氨基或能够转化成氨基的基团，然后使所得双酰肼进行闭环以产生恶二唑。 该产品是双重重氮组分，特别是对于具有非常高的着色强度，透明和纯净的色调，良好的耐光牢度，耐热性和溶剂性的颜料。

公开(公告)号：US4370269A

公开(公告)日：1983-01-25

申请号：US666312

申请日：1976-03-12

Applicant: Friedrich W. Weingarten ,  Klaus Hunger ,  Ernst Klappert

Inventor： Friedrich W. Weingarten ,  Klaus Hunger ,  Ernst Klappert

IPC: C09B29/33 ,  C09B29/01 ,  C09B29/32 ,  D06P1/44

CPC classification number: C09B29/338

Abstract: The compound of the formula: ##STR1## is a valuable pigment of high fastness properties and high covering power.

Abstract translation: 下式的化合物：是高坚牢性和高覆盖力的有价值的颜料。

公开(公告)号：US4368155A

公开(公告)日：1983-01-11

申请号：US259965

申请日：1981-05-04

Applicant: Klaus Hunger ,  Manfred Pesenacker

Inventor： Klaus Hunger ,  Manfred Pesenacker

IPC: C09B29/01 ,  C09B29/32 ,  C09B29/33 ,  D06P1/44

CPC classification number: C09B29/338 ,  C09B29/0003

Abstract: When diazotizing a benzanilide of the formula ##STR1## wherein R is methoxy and X is carbamoyl or acetamino and coupling it onto 5-acetoacetylaminobenzimidazolone-(2), a monoazo pigment is obtained having the formula ##STR2## wherein R is methoxy and X is carbamoyl or acetamino. The monoazo pigments are effective for coloring plastics and lacquers and exhibit a very good fastness to light, solvents, over-lacquering, bleeding and have a high heat resistance.

Abstract translation: 当其中R为甲氧基并且X为氨基甲酰基或乙酰氨基并将其偶联至5-乙酰乙酰氨基苯并咪唑酮 - （2）的式“IMAGE”的苯甲酰苯胺重氮化时，得到具有式“IMAGE”的单偶氮颜料，其中R为甲氧基且X为 氨基甲酰基或乙酰氨基。 单偶氮颜料对于着色塑料和漆是有效的，并表现出非常好的耐光牢度，溶剂，超漆，渗色性和耐热性。

公开(公告)号：US4302389A

公开(公告)日：1981-11-24

申请号：US086126

申请日：1979-10-18

Applicant: Klaus Hunger ,  Manfred Pesenacker

Inventor： Klaus Hunger ,  Manfred Pesenacker

IPC: C09B29/01 ,  C09B29/32 ,  C09B29/33 ,  D06P1/44

CPC classification number: C09B29/338 ,  C09B29/0003

Abstract: When diazotizing a p-amino-benzoic acid anilide, the anilide nucleus of which is substituted in its para-position by carbamoyl, acetamino or chloro and coupling it onto 5-acetoacetylamino-benzimidazolone-(2) monoazo pigments are obtained having a high fastness to light, solvents, overlacquering and bleeding and a very high heat resistance.

Abstract translation: 当苯胺酰胺在其对位被氨基甲酰基，乙酰氨基或氯取代时，将其苯胺酰胺核重氮化，并将其偶联到5-乙酰乙酰氨基 - 苯并咪唑酮 - （2）单偶氮颜料上，得到具有高坚牢度 光，溶剂，叠加和渗出以及非常高的耐热性。