公开(公告)号：US4677200A

公开(公告)日：1987-06-30

申请号：US719256

申请日：1985-04-03

Applicant: Klaus Hunger

Inventor： Klaus Hunger

IPC: C09B29/32 ,  C09B29/33 ,  C09B33/04 ,  C09B43/08 ,  C09B29/01 ,  C09B31/10 ,  D06P1/44

CPC classification number: C09B43/08 ,  C09B29/338 ,  C09B33/04 ,  Y10S534/07

Abstract: The invention relates to aminoazo compounds of the formula I ##STR1## in which X and Y are identical or different and denote hydrogen, chlorine, bromine, methyl, methoxy, ethoxy, nitro, trifluoromethyl, carbomethoxy or carboethoxy, A represents hydrogen, methyl or ethyl, and Z in the 6- or 7-position of the heteroaromatic ring system is hydrogen, chlorine or bromine, methyl, methoxy, ethoxy, carbomethoxy, carboethoxy or nitro.The compounds of the formula I are prepared by coupling a monodiazotized p-diaminobenzene substituted by X and Y analogously to the formula I with a 5-acetoacetylaminobenzimidazolone which carries the radicals A and Z analogously to the formula I. In the case where X, Y or Z does not denote a nitro group, it is possible to use in place of the p-diaminobenzene derivative a p-aminonitrobenzene derivative which is disubstituted by X and Y in the 2- and 5-positions. In this case, the product after diazotization and coupling is initially a nitro compound which can be converted by reduction into the aminoazo compound of the formula I.The aminoazo compounds are used as starting materials for preparing disazo compounds, preferably disazo pigments, through diazotization in conventional manner and coupling onto compounds which are capable of coupling, for example onto 5-acetoacetylaminobenzimidazolones. The disazo pigments are distinguished by high tinctorial strength, excellent fastness to solvents and migration, and high thermostability.

Abstract translation: 本发明涉及式I（I）的氨基偶氮化合物，其中X和Y相同或不同，表示氢，氯，溴，甲基，甲氧基，乙氧基，硝基，三氟甲基，甲酯基或乙氧羰基，A代表氢 ，芳基环系统的6-或7-位中的甲基或乙基，Z是氢，氯或溴，甲基，甲氧基，乙氧基，甲酯基，乙氧羰基或硝基。 式I化合物通过将与X和Y取代的单重氮化的对二氨基苯类似于式I的5-乙酰乙酰氨基苯并咪唑酮偶联而制备，所述5-乙酰乙酰氨基苯并咪唑酮与式I相似地携带基团A和Z。在X，Y 或Z不表示硝基时，可以使用在2-和5-位被X和Y二取代的对氨基硝基苯衍生物代替对二氨基苯衍生物。 在这种情况下，重氮化和偶联后的产物最初是可以通过还原转化为式I的氨基偶氮化合物的硝基化合物。氨基偶氮化合物用作制备双偶氮化合物，优选二偶氮颜料的起始原料，通过重氮化 常规方式和偶合到能够偶联到例如5-乙酰乙酰氨基苯并咪唑酮上的化合物上。 双偶氮颜料的特征在于高着色强度，优异的耐溶剂性和迁移性，以及高的热稳定性。

公开(公告)号：US4589921A

公开(公告)日：1986-05-20

申请号：US743270

申请日：1985-06-10

Applicant: Klaus Hunger ,  Wolfgang Rieper

Inventor： Klaus Hunger ,  Wolfgang Rieper

IPC: C09B67/10 ,  C09B62/01 ,  C09B67/00 ,  C09D11/02

CPC classification number: C09B67/0015

Abstract: The invention relates to a process for improving the application properties of Pigment Yellow 13. The crude pigment is heated in an aqueous suspension to temperatures above 100.degree. C. Pigment Yellow 13 thus obtained is particularly suitable for replacing lead-containing chrome yellow pigments of comparable shade.

Abstract translation: 本发明涉及改善颜料黄13的应用性能的方法。将粗颜料在水性悬浮液中加热至高于100℃的温度。如此获得的颜料黄13特别适用于替代可比较的含铅的铬黄色颜料 阴影

公开(公告)号：US4287122A

公开(公告)日：1981-09-01

申请号：US772268

申请日：1977-02-25

Applicant: Klaus Hunger ,  Ernst Klappert ,  Konrad Lohe

Inventor： Klaus Hunger ,  Ernst Klappert ,  Konrad Lohe

IPC: C08K5/00 ,  C08K5/22 ,  C08K5/23 ,  C08L1/00 ,  C08L7/00 ,  C08L21/00 ,  C08L23/00 ,  C08L27/00 ,  C08L33/00 ,  C08L33/02 ,  C08L67/00 ,  C08L77/00 ,  C08L101/00 ,  C09B29/01 ,  C09B29/20 ,  C09D7/00 ,  C09D7/12 ,  C09D11/00 ,  C09D11/02 ,  D06P1/44 ,  D06P1/90

CPC classification number: C09B29/0003 ,  C08K5/23 ,  C09B29/20

Abstract: Valuable pigments are obtained by diazotizing 1-aminobenzene-2-(carboxylic acid methyl or ethyl ester)-5-(2',3'-dichloro-anilide) and coupling it onto 1-(2'-hydroxy-3'-naphthoylamino)-4-acetamino-benzene. The resulting pigments are then subjected to a thermal aftertreatment. These pigments show a high tinctorial strength, a pure shade, a high fastness to migration, especially to overlacquering, to light and weathering and a high heat stability.

Abstract translation: 通过重氮化1-氨基苯-2-（羧酸甲酯或乙酯）-5-（2'，3'-二氯苯胺）并将其偶联至1-（2'-羟基-3'-萘甲酰氨基 ）-4-乙酰氨基 - 苯。 然后将所得颜料进行热后处理。 这些颜料显示出高的着色强度，纯色调，高耐迁移牢度，特别是对于覆盖光，耐候性和高热稳定性。

公开(公告)号：US4195020A

公开(公告)日：1980-03-25

申请号：US15603

申请日：1979-02-23

Applicant: Klaus Hunger ,  Joachim Ribka

Inventor： Klaus Hunger ,  Joachim Ribka

IPC: C08K5/00 ,  C08K5/22 ,  C08L33/00 ,  C08L33/02 ,  C09B29/33 ,  C09D7/00 ,  C09D7/12 ,  C09B29/36

CPC classification number: C09B29/338

Abstract: A pigment of the formula ##STR1## wherein R.sub.1 is hydrogen, chlorine or methyl and R.sub.2 is hydrogen or methyl. These pigments have a high color strength, fastness to overvarnishing, fastness to migration and fastness to light and weathering. They can be used in all fields in which pigments are used as coloring material, especially for the coloring of lacquers with metal-effect.

Abstract translation: 式IMA的颜料，其中R 1是氢，氯或甲基，R 2是氢或甲基。 这些颜料具有高的着色力，耐擦洗性，耐迁移性和耐光性和耐候性。 它们可用于所有使用颜料作为着色材料的领域，特别是用于具有金属效果的漆的着色。

公开(公告)号：US4169830A

公开(公告)日：1979-10-02

申请号：US850464

申请日：1977-11-10

Applicant: Klaus Hunger

Inventor： Klaus Hunger

IPC: C08K5/00 ,  C08K5/22 ,  C08K5/23 ,  C09B35/28 ,  C09D7/00 ,  C09D7/12 ,  C09D11/00 ,  C09D11/02 ,  C09B33/12 ,  D06P1/04 ,  D06P1/44

CPC classification number: C09B35/28

Abstract: Disazo compounds, obtained by diazotizing 4,4'-diaminobenzanilide and coupling it to one or more acetoacetyl benzimidazolones, are valuable pigments of good dispersibility, tinctorial strength, fastness to light, weathering, solvents and migration.

Abstract translation: 通过重氮化4,4'-二氨基苯甲酰苯胺并将其偶联到一种或多种乙酰乙酰基苯并咪唑酮上获得的双偶氮化合物是具有良好分散性，着色强度，耐光性，耐候性，溶剂和迁移性的有价值的颜料。

公开(公告)号：US4096157A

公开(公告)日：1978-06-20

申请号：US725837

申请日：1976-09-23

Applicant: Klaus Hunger

Inventor： Klaus Hunger

IPC: C09B55/00 ,  C07F1/08

CPC classification number: C09B55/002

Abstract: Azamethines which are obtainable by condensation of a 1-formyl-2-hydroxy-3-naphthoic acid arylamide with an orthohydroxy- or ortho-methoxy aniline form metal complexes with zinc, cadmium, cobalt, nickel or copper. These complexes are useful as pigments.

Abstract translation: 可以通过1-甲酰基-2-羟基-3-萘甲酸芳基酰胺与邻羟基或邻甲氧基苯胺缩合得到的氮杂环丁烷与锌，镉，钴，镍或铜形成金属络合物。 这些配合物可用作颜料。

公开(公告)号：US4082741A

公开(公告)日：1978-04-04

申请号：US751072

申请日：1976-12-16

Applicant: Klaus Hunger ,  Dieter Weber

Inventor： Klaus Hunger ,  Dieter Weber

IPC: C08K5/00 ,  C08K5/22 ,  C08L7/00 ,  C08L21/00 ,  C08L33/00 ,  C08L33/02 ,  C08L67/00 ,  C08L77/00 ,  C09B35/34 ,  C09D7/00 ,  C09D7/12 ,  C09B33/12 ,  C09B33/14 ,  D06P1/44 ,  D06P1/52

CPC classification number: C09B35/34

Abstract: The compounds obtained by bis-diazotizing 3,8-diamino-phenanthridone-(10) and coupling it onto one or a mixture of enolizable ketomethylene coupling components having no solubilizing groups are pigments of high tinctorial strength and fastness to migration, heat, light and chemicals.

公开(公告)号：US3947516A

公开(公告)日：1976-03-30

申请号：US489538

申请日：1974-07-18

Applicant: Klaus Hunger ,  Theodor Papenfuhs

Inventor： Klaus Hunger ,  Theodor Papenfuhs

IPC: C07D209/48 ,  C07C67/00 ,  C07C231/00 ,  C07C231/12 ,  C07C235/66 ,  C07C255/60 ,  C07C311/46 ,  C07C313/00 ,  C07C315/04 ,  C07C317/40 ,  C07D235/02 ,  C07D235/26 ,  C07D237/30 ,  C07D239/72 ,  C07D241/40 ,  C09B55/00 ,  C07C103/26

CPC classification number: C09B55/00

Abstract: Aldehydes of a 2-hydroxy-naphthalene-3-carboxylic acid arylide of the general formula ##SPC1##In which X represents a hydrogen, chlorine or bromine atom, and Ar represents a naphthyl group, a benzimidazolone, chlorobenzimidazoline, 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 sulfonamido groups and a process for their preparation wherein the corresponding 2-hydroxynaphthalene-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: 通式为I的2-羟基 - 萘-3-羧酸芳基化物的醛，其中X表示氢，氯或溴原子，Ar表示萘基，苯并咪唑啉酮，氯代苯并咪唑啉，喹唑酮，喹喔啉，邻苯二甲酰亚胺，酞嗪基 或可以带有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，苯甲酰基氨基，甲酰氨基或亚磺酰氨基的苯基和其制备方法， 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：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。