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：US4476052A

公开(公告)日：1984-10-09

申请号：US357287

申请日：1982-03-11

Applicant: Klaus Hunger ,  Joachim Ribka ,  Friedrich Weingarten ,  Wolfgang Rieper

Inventor： Klaus Hunger ,  Joachim Ribka ,  Friedrich Weingarten ,  Wolfgang Rieper

IPC: C09D7/00 ,  C09B29/33 ,  C09B67/10 ,  C09B67/20 ,  C09D7/12 ,  C09B29/32 ,  C09D3/00 ,  C09D11/02

CPC classification number: C09B67/0015

Abstract: Process for the aftertreatment of the azo pigment of the formula ##STR1## C.I. PIGMENT ORANGE 36 wherein the crude pigment obtained after coupling is heated to temperatures from 100.degree. to 150.degree. C. in dry or wet condition in a solvent which is water-immiscible or not indefinitely water-miscible and the pigment is isolated in known manner. The pigment aftertreated in this way shows substantially improved hiding power while the same pigment prepared in the usual way has poor hiding power and can not be used in stoving lacquers.

Abstract translation: 后处理式（Ⅰ）的偶氮颜料的方法 颜料橙36，其中将偶联后获得的粗颜料在干燥或潮湿条件下在100℃至150℃的温度下在与水不混溶的溶剂中或不是无限期地与水混溶的溶剂中加热，并以已知方式分离颜料。 以这种方式处理的颜料显示出显着改善的遮盖力，而以通常方式制备的相同颜料具有差的遮盖力并且不能用于烘烤漆中。

公开(公告)号：US4182708A

公开(公告)日：1980-01-08

申请号：US761071

申请日：1977-01-21

Applicant: Josef Landler ,  Klaus Hunger ,  Erhard Worfel

Inventor： Josef Landler ,  Klaus Hunger ,  Erhard Worfel

IPC: C09B29/00 ,  C09B41/00 ,  C09B29/20 ,  C09B29/32 ,  C09B29/36 ,  C09B29/38

CPC classification number: C09B41/00 ,  C09B29/00

Abstract: Azo pigments are obtained by diazotizing a diazotizable aromatic amine without solubilizing groups in anhydrous dipolar aprotic water-miscible solvents with the stoichiometric amount or a small excess of nitrosylsulfuric acid or nitrosyl chloride, coupling the diazonium compound so obtained with a coupling component and isolating the pigment obtained in usual manner. This process is carried out in homogeneous solution and yields azo pigments the advantageous properties of which cannot be achieved by other methods, for example, the excellent purity, grain softness, narrow range of particle size distribution, excellent dispersibility in plastic materials and color lacquers, high gloss and excellent opacity in color lacquers.

Abstract translation: 偶氮颜料通过重氮化可重氮化的芳族胺而不增溶基团与化学计量量或少量过量亚硝酰基亚磺酰氯或亚硝酰氯的无水偶极非质子水溶性溶剂进行重氮化，将所得重氮化合物与偶联组分偶合并分离出颜料 以通常的方式获得。 该方法在均匀溶液中进行，产生偶氮颜料，其有利性质不能通过其它方法实现，例如，优异的纯度，颗粒柔软度，窄的粒度分布范围，在塑料材料和彩色漆中的优异分散性， 高光泽和优异的不透明度在彩色漆。

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：US4720541A

公开(公告)日：1988-01-19

申请号：US627497

申请日：1984-07-06

Applicant: Wolfgang Rieper ,  Klaus Hunger

Inventor： Wolfgang Rieper ,  Klaus Hunger

IPC: C09B67/10 ,  C09B67/14 ,  C09B35/035 ,  C09D7/12 ,  D06P1/44

CPC classification number: C09B67/0017 ,  C09B67/0015

Abstract: Process for improving the application properties of disazo pigments obtained by coupling bis-diazotized chlorine-substituted 4,4'-diaminobiphenyls with acetoacetylaminobenzenes, which includes adding sulfite ions to the pigment suspension obtained in the coupling and then heating for one half to two hours at 50.degree. to 100.degree. C. The process produces, above all in large scale industrial batches, a product of uniform quality and having acceptable fastness to solvents, overlacquering, migration and bleeding.

Abstract translation: 通过将双重重氮化的氯取代的4,4'-二氨基联苯与乙酰乙酰氨基苯偶联而获得的双偶氮颜料的应用性能的改进方法，其包括将亚硫酸根离子加入到偶联中得到的颜料悬浮液中，然后加热半小时至两小时 50℃至100℃。该工艺首先在大规模工业批次中生产质量均匀且具有可接受的溶剂牢度，超标，迁移和渗出的产品。

公开(公告)号：US4665163A

公开(公告)日：1987-05-12

申请号：US507711

申请日：1983-06-23

Applicant: Klaus Hunger ,  Heinrich Frolich ,  Hans-Joachim Lenz

Inventor： Klaus Hunger ,  Heinrich Frolich ,  Hans-Joachim Lenz

IPC: C09B35/033 ,  C09B35/10 ,  C09B41/00 ,  C09B35/035 ,  C09B67/20 ,  C09D11/02

CPC classification number: C09B35/105

Abstract: Diaryl pigments having an excellent stability to heat are obtained by carrying out the coupling of bis-diazotized 3,3'-dichloro-4,4'-diaminobiphenyl with acetoacetanilides in the presence of an added quantity of acetoacetanilides which are monosubstituted or disubstituted in the 3-position or 4-position of the nucleus. As a result of their good heat stability, these pigments are particularly suitable for pigmenting plastics having processing temperatures above 200.degree. C.

Abstract translation: 通过在添加量的乙酰乙酰苯胺的存在下进行双重重氮化的3,3'-二氯-4,4'-二氨基联苯与乙酰乙酰苯胺的偶合获得具有优异的耐热稳定性的二芳基颜料，所述乙​​酰乙酰替苯胺在 核的3位或4位。 由于其良好的热稳定性，这些颜料特别适用于加工温度高于200℃的着色塑料。

公开(公告)号：US4607096A

公开(公告)日：1986-08-19

申请号：US439270

申请日：1982-11-04

Applicant: Josef Landler ,  Klaus Hunger ,  Erhard Worfel

Inventor： Josef Landler ,  Klaus Hunger ,  Erhard Worfel

IPC: C09B29/20 ,  C09B29/00 ,  C09B41/00 ,  C09B46/00 ,  C09B67/00 ,  C09B67/20

CPC classification number: C09B41/002 ,  C09B29/00

Abstract: Azo pigments are obtained by diazotizing a diazotizable aromatic amine without solubilizing groups in anhydrous dipolar aprotic water-miscible solvents with the stoichiometric amount or a small excess of nitrosylsulfuric acid or nitrosyl chloride, coupling the diazonium compound so obtained with a coupling component and isolating the pigment obtained in usual manner. This process is carried out in homogeneous solution and yields azo pigments the advantageous properties of which cannot be achieved by other methods, for example, the excellent purity, grain softness, narrow range of particle size distribution, excellent dispersibility in plastic materials and color lacquers, high gloss and excellent opacity in color lacquers.

Abstract translation: 偶氮颜料通过重氮化可重氮化的芳族胺而不增溶基团与化学计量量或少量过量亚硝酰基亚磺酰氯或亚硝酰氯的无水偶极非质子水溶性溶剂进行重氮化，将所得重氮化合物与偶联组分偶联并分离出颜料 以通常的方式获得。 该方法在均匀溶液中进行，产生偶氮颜料，其有利性质不能通过其它方法实现，例如，优异的纯度，颗粒柔软度，窄的粒度分布范围，在塑料材料和彩色漆中的优异分散性， 高光泽和优异的不透明度在彩色漆。

公开(公告)号：US4555568A

公开(公告)日：1985-11-26

申请号：US162074

申请日：1980-06-23

Applicant: Klaus Hunger

Inventor： Klaus Hunger

IPC: C09B29/20 ,  C09B29/01 ,  C09B29/15 ,  D06P1/44 ,  D06P3/24

CPC classification number: C09B29/20

Abstract: When diazotizing lower alkyl esters of 3-nitro-4-aminobenzoic acid and coupling them onto 5-(2'-hydroxy-3'-naphthoylamino)-benzimidazolone-(2) which may be substituted in 6'-position by chlorine or bromine, in 1-position by methyl or ethyl and in the benzo-nucleus by chlorine, bromine, methyl, ethyl, methoxy or ethoxy, and such as further illustrated by a representative formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, X is hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, Y is hydrogen, methyl or ethyl, and Z is hydrogen, chlorine or bromine. Colorants are obtained which are especially useful for pigmenting plastics, spinning masses, printing inks, varnishes and paints. The dyeings obtained therewith are fast to light, weathering, solvents and migration, especially fast to overvarnishing and bleeding.

Abstract translation: 当重氮化3-硝基-4-氨基苯甲酸的低级烷基酯并将其偶联到5-（2'-羟基-3'-萘甲酰基氨基） - 苯并咪唑酮 - （2）时，其可以在6'位被氯或溴取代 在甲基或乙基的1-位，在苯并 - 核中由氯，溴，甲基，乙基，甲氧基或乙氧基取代，并且如通过其代表性的式I进一步说明的，其中R是1至4个碳的烷基 原子，X是氢，氯，溴，甲基，乙基，甲氧基或乙氧基，Y是氢，甲基或乙基，Z是氢，氯或溴。 得到着色剂，其对于着色塑料，纺丝团，印刷油墨，清漆和油漆特别有用。 由此获得的染色具有耐光，耐候性，溶剂和迁移性，特别是快速渗透和渗色。