公开(公告)号：US4251441A

公开(公告)日：1981-02-17

申请号：US36381

申请日：1979-05-07

Applicant: Heinrich Frolich ,  Klaus Hunger

Inventor： Heinrich Frolich ,  Klaus Hunger

IPC: C08K5/00 ,  C08K5/22 ,  C08K5/23 ,  C08L7/00 ,  C08L21/00 ,  C08L23/00 ,  C08L33/00 ,  C08L33/02 ,  C08L67/00 ,  C08L101/00 ,  C09B29/33 ,  C09B67/22 ,  C09D7/00 ,  C09D7/12 ,  C09D11/00 ,  C09D11/02 ,  C09B29/32 ,  D06P1/18 ,  D06P1/44 ,  D06P1/90

CPC classification number: C09B29/337

Abstract: Mixtures of monoazo compounds which are obtainable by diazotizing 0.75 to 0.85 molar equivalent of 5-nitro-2-amino-anisol and 0.25 to 0.15 molar equivalent of 3-nitro-4-amino-anisol and coupling onto 2-acetoacetylamino-anisol are pigments of high tinctorial strength, transparency, gloss and fastness to light having good rheological properties.

Abstract translation: 通过重氮化0.75-0.85摩尔当量的5-硝基-2-氨基茴香醚和0.25-0.15摩尔当量的3-硝基-4-氨基茴香醚并偶联到2-乙酰乙酰氨基茴香醚上的单偶氮化合物的混合物是颜料 具有高的着色强度，透明度，光泽和耐光性，具有良好的流变性能。

公开(公告)号：US4045428A

公开(公告)日：1977-08-30

申请号：US603914

申请日：1975-08-12

Applicant: Fritz Meininger ,  Klaus Hunger ,  Hartmut Springer

Inventor： Fritz Meininger ,  Klaus Hunger ,  Hartmut Springer

IPC: C09B62/51 ,  C09B62/50 ,  C09B62/74 ,  D06P1/06 ,  D06P1/38

CPC classification number: C09B62/51

Abstract: 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.

Abstract translation: 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。

公开(公告)号：US4005068A

公开(公告)日：1977-01-25

申请号：US476267

申请日：1974-06-04

Applicant: Klaus Hunger ,  Bernhard Mees

Inventor： Klaus Hunger ,  Bernhard Mees

IPC: C08K5/00 ,  C08K5/22 ,  C08L1/00 ,  C08L7/00 ,  C08L21/00 ,  C08L27/00 ,  C08L33/00 ,  C08L33/02 ,  C08L67/00 ,  C08L77/00 ,  C09B35/03 ,  C09B35/34 ,  C09D11/00 ,  C09D11/02 ,  D06P3/00 ,  D06P3/24 ,  D06P3/52

CPC classification number: C09B35/34

Abstract: Novel valuable, water-insoluble disazo pigments of the general formula 1 ##SPC1##Wherein R is hydrogen, methyl, methoxy or halogen, preferably chlorine or bromine, and X also represents hydrogen or halogen, preferably chlorine. The disazo compounds are obtained by bisdiazotizing a 2,7-diaminodiphenylenesulfone and coupling it on an acetoacetylbenzimidazolone. These pigments are suitable for preparing printing inks, color lakes and dispersion paints, for dyeing rubber, plastics and natural or synthetic resins. Furthermore, they are suitable for the printing of pigments on substrates, especially textile fibre materials or other flat articles such as paper.The pigments may be used for other purposes, for example in a finely divided form for dyeing rayon of viscose or cellulose ethers or esters, polyamides, polyurethanes, polyglycolterephthalate or polyacrylonitriles in the spinning mass or for dyeing paper. The pigments may be processed well in the mentioned media. The dyeings have a good color intensity as well as good fastnesses to light and to migration and are resistant to the influence of heat and chemical products, above all solvents.

Abstract translation: 具有通式1的新型有价值的水不溶性双偶氮颜料WHEREIN R是氢，甲基，甲氧基或卤素，优选氯或溴，X也代表氢或卤素，优选氯。 双偶氮化合物通过将2,7-二氨基二苯基砜双重重氮化并将其偶联在乙酰乙酰基苯并咪唑酮上获得。 这些颜料适用于制备用于染色橡胶，塑料和天然或合成树脂的印刷油墨，色淀和分散体涂料。 此外，它们适用于在基材上，特别是纺织纤维材料或其他扁平制品如纸上的颜料的印刷。

公开(公告)号：US4987258A

公开(公告)日：1991-01-22

申请号：US17062

申请日：1987-02-20

Applicant: Klaus Hunger ,  Heinrich Frolich ,  Kurt C. Habig

Inventor： Klaus Hunger ,  Heinrich Frolich ,  Kurt C. Habig

Abstract: The invention relates to 4,4'-diaminodiphenyl compounds of the formula I ##STR1## in which X denotes the n-propyl, isopropyl, n-butyl, isobutyl, 1-methylpropyl, n-propoxy, isopropoxy, isobutoxy, 1-methylpropoxy or 2-methoxyethoxy radical and A is 0 or the equivalent of an inorganic acid.The preparation is effected by reducing ortho-X-substituted nitrobenzene and benzidine rearrangement of the resulting hydrazobenzene derivative. The compounds of the formula (I) are suitable for use as components in the preparation of dyes and pigments.

Abstract translation: 本发明涉及式I（I）的4,4'-二氨基二苯基化合物，其中X表示正丙基，异丙基，正丁基，异丁基，1-甲基丙基，正丙氧基，异丙氧基，异丁氧基， 1-甲基丙氧基或2-甲氧基乙氧基，A为0或相当于无机酸。 通过还原邻位取代的硝基苯和所得的肼苯衍生物的联苯胺重排来进行制备。 式（I）的化合物适用于制备染料和颜料的组分。

公开(公告)号：US4906735A

公开(公告)日：1990-03-06

申请号：US366359

申请日：1989-06-15

Applicant: Klaus Hunger

Inventor： Klaus Hunger

IPC: C09B29/33 ,  C09B41/00 ,  C09B67/20

CPC classification number: C09B29/334 ,  C09B41/002

Abstract: An improved process for the manufacture of a monoazo acetoacetylaminobenzimidazolone pigment of the formula ##STR1## by coupling the components in an aqueous medium in the presence of an oxethylation product of an alcohol or alcohol mixture having from 8 to 14 carbon atoms and 3 to 10 mols of ethylene oxide, and heating the aqueous pigment suspension after complete coupling. The pigment thus obtained avoids an after-treatment in anhydrous organic solvents and has good tinctorial strength, high hiding power and good properties with respect to flow and dispersibility.

Abstract translation: 在具有8至14个碳原子和3至10摩尔的醇或醇混合物的氧乙基化产物的存在下，通过将水溶液中的组分偶联，制备式“IMAGE”的单偶氮乙酰乙酰氨基苯并咪唑酮颜料的改进方法 的环氧乙烷，并且在完全偶联后加热水性颜料悬浮液。 由此得到的颜料避免了在无水有机溶剂中的后处理，并且在流动性和分散性方面具有良好的着色强度，高遮盖力和良好的性能。

公开(公告)号：US4686287A

公开(公告)日：1987-08-11

申请号：US719255

申请日：1985-04-03

Applicant: Klaus Hunger

Inventor： Klaus Hunger

IPC: C09B35/03 ,  C08K5/00 ,  C08K5/23 ,  C08K5/3447 ,  C09B35/035 ,  C09B43/08 ,  C09B31/10 ,  C09B67/48 ,  D06P1/44

CPC classification number: C09B35/035 ,  C08K5/0041 ,  C08K5/23 ,  C08K5/3447 ,  C09B43/08

Abstract: Disazo compounds of the formula I ##STR1## in which X and Y are identical or different and denote hydrogen, bromine, chlorine, methyl, methoxy, ethoxy, nitro, trifluoromethyl, carbomethoxy or carboethoxy, A.sup.1 and A.sup.2, independently of each other, represent hydrogen, methyl or ethyl and Z.sup.1 and Z.sup.2 in the 6- or 7-position of the heteroaromatic ring system, independently of each other, represent hydrogen, bromine, chlorine, methyl, methoxy, ethoxy, carbomethoxy, carboethoxy or nitro, are obtained 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.sup.1 and Z.sup.2 analogously to the formula I, and reacting the resulting aminoazo compound after another diazotization with a 5-acetoacetylaminobenzimidazolone which carries the radicals A.sup.2 and Z.sup.2 analogously to the formula I, to give the disazo compound of the formula I. The crude product is subsequently thermally aftertreated at 80.degree. to 200.degree. C.In the case where X, Y or Z.sup.1 does not denote a nitro group, it is possible to use as an alternative to the p-diaminobenzene derivative a corresponding p-aminonitrobenzene derivative. In this case, analogous diazotization and coupling is followed by reduction of the resulting nitroazo compound to the aminoazo compound, which is converted into the compound of the formula I as described above.The symmetrical or asymmetrical disazo compounds of the formula (I) are obtained in a particle size of .ltoreq.0.25 .mu.m and are suitable for use as pigments in printing inks, lakes and emulsion paints, for coloring plastics, rubber, natural and synthetic resins or spinning compositions and for pigment printing on, for example, textile fiber materials and paper. The pigments are tinctorially very strong and have very high solvent, migration, light and weathering fastness properties and a high thermostability.

公开(公告)号：US4139527A

公开(公告)日：1979-02-13

申请号：US389660

申请日：1973-08-21

Applicant: Fritz Meininger ,  Klaus Hunger ,  Hartmut Springer

Inventor： Fritz Meininger ,  Klaus Hunger ,  Hartmut Springer

IPC: C09B62/45 ,  C09B62/74 ,  C09B62/46

CPC classification number: C09B62/45

Abstract: A water-soluble monoazo-dyestuff having in form of the free acid the formula ##STR1## WHEREIN A represents as a radical of a diazo component phenyl; phenyl substituted by lower alkyl, lower alkylsulfonyl, lower alkoxy, carboxyl, trifluoromethyl, cyano, fluorine, chlorine, bromine, sulfonamido and carbonamido; naphthyl, nitronaphthylene, ##STR2## X represents hydrogen; phenyl; nitrophenylene or naphthyl, R represents as a bridging member --SO.sub.2 --, --CO--, --S--, --CO--NH--, --NH--CO--, --SO.sub.2 --NH--, --NH--SO.sub.2 --, --CH.sub.2 --, --NH-- or --N(lower alkyl)--; B represents as the radical of a coupling component N,N-di(lower alkyl)amino-phenylene, N,N-di (lower alkyl)amino-chloro-phenylene; hydroxyquinoline; diphenylamine; hydroxynaphthylene; hydroxynaphthylene substituted by acetylamino, benzoylamino or ##STR3## aminonaphthylene; ##STR4## substituted on the benzene nucleus by lower alkyl, lower alkoxy, chlorine and bromine; Z represents hydrogen, --COOH or --SO.sub.3 H, Y represents a direct linkage or one of the groupings --CH.sub.2 --, --CH.sub.2 13 CH.sub.2 --, --NH-- or --N(lower alkyl)--, the said groupings --Y--SO.sub.2 --CH.sub.2 --CH.sub.2 --O--PO.sub.3 H.sub.2 and Z being linked to A, B or X, n stands for an integer from 1 to 3 and m stands for an integer from 1 to 5, said dyestuffs being suitable for the dyeing or printing of leather or fibrous materials consisting of native or regenerated cellulose, wool, silk or polyamides, the dyeings and prints obtained on said materials being distinguished by deep tints and very good fastness properties to light and wetting.

Abstract translation: 具有游离酸形式的水溶性单偶氮染料，其中A表示为重氮组分苯基的基团; 低级烷基，低级烷基磺酰基，低级烷氧基，羧基，三氟甲基，氰基，氟，氯，溴，亚磺酰氨基和碳酰氨基取代的苯基; 萘基，亚硝基萘，X表示氢; 苯基; 硝基亚苯基或萘基，R表示作为桥连构件-SO 2 - ， - CO - ， - S - ， - CO-NH-，-NH-CO-，-SO 2 -NH-，-NH-SO 2 - ， - -NH-或-N（低级烷基） - ; B表示作为偶联成分N，N-二（低级烷基）氨基亚苯基，N，N-二（低级烷基）氨基 - 氯 - 亚苯基的基团。 羟基喹啉; 二苯胺; 羟基萘 由乙酰氨基，苯甲酰氨基或氨基亚萘基取代的羟基萘; 在苯核上由低级烷基，低级烷氧基，氯和溴取代的“IMAGE” Z表示氢，-COOH或-SO 3 H，Y表示直接键或-CH 2 - ， - CH 2 13 CH 2 - ， - NH-或-N（低级烷基） - 之一，所述基团-Y-SO 2 -CH 2 -CH2-O-PO3H2和Z与A，B或X连接，n代表1至3的整数，m代表1至5的整数，所述染料适用于皮革或纤维的染色或印花 由天然或再生纤维素，羊毛，丝绸或聚酰胺组成的材料，所述材料上获得的染色和印刷品通过深色调区分，并且对光和润湿具有非常好的牢度性能。

公开(公告)号：US4131733A

公开(公告)日：1978-12-26

申请号：US827380

申请日：1977-08-24

Applicant: Klaus Hunger

Inventor： Klaus Hunger

IPC: C07D209/48 ,  C07D235/26 ,  C07D237/32 ,  C07D239/96 ,  C07D241/44 ,  C07D263/58 ,  C09B55/00 ,  C09B17/04

CPC classification number: C07D209/48 ,  C07D235/26 ,  C07D237/32 ,  C07D239/96 ,  C07D241/44 ,  C07D263/58 ,  C09B55/002

Abstract: Condensing of 1-formyl-2-hydroxy-3-naphthalenecarboxylic acid arylamides with ammonia or aromatic amines yields novel azamethines which are useful as coloring matters, especially as pigments.

Abstract translation: 1-甲酰基-2-羟基-3-萘甲酸芳基酰胺与氨或芳族胺的缩合产生可用作着色剂，特别是作为颜料的新型azamethines。

公开(公告)号：US3980635A

公开(公告)日：1976-09-14

申请号：US616250

申请日：1975-09-24

Applicant: Klaus Hunger ,  Joachim Ribka ,  Wolfgang Rieper

Inventor： Klaus Hunger ,  Joachim Ribka ,  Wolfgang Rieper

IPC: C09D7/00 ,  C09B35/03 ,  C09B35/08 ,  C09B35/18 ,  C09B67/10 ,  C09D7/12 ,  C09B43/00

CPC classification number: C09B67/0015 ,  C09B35/18

Abstract: A highly covering disazo pigment having the chemical constitution ##SPC1##Which is characterized by a specific surface of 12 - 30, preferably 15 to 25, m.sup.2 /g, a maximum of the grain size distribution of between 250 and 500 nm and a proportion of these grain sizes in the total distribution of 35 - 65 percent, preferably 45 - 60 percent. This new pigment form is obtained by heating the pigment obtained after coupling with a solvent which is immiscible with water or miscible with water to a limited degree only to temperatures above 100.degree.C.

Abstract translation: 具有化学结构的高度覆盖的双偶氮颜料，其特征在于表面特性为12-30，优选为15至25，M2 / G，250和500nm之间的粒度分布的最大值以及这些颗粒尺寸的比例 总共分配35 - 65％，优先选择45 - 60％。 通过将与水不混溶的溶剂偶联后获得的颜料与水混合获得的新颜料形式通过加热至限于100℃以上的温度而获得。

公开(公告)号：US3974136A

公开(公告)日：1976-08-10

申请号：US434039

申请日：1974-01-17

Applicant: Klaus Hunger ,  Joachim Ribka ,  Wolfgang Rieper

Inventor： Klaus Hunger ,  Joachim Ribka ,  Wolfgang Rieper

IPC: C09D7/00 ,  C09B35/08 ,  C09B35/10 ,  C09B67/10 ,  C09D7/12 ,  C09B43/00

CPC classification number: C09B35/105 ,  C09B67/0015

Abstract: The disazo pigment of the formula ##SPC1##Characterized by a specific surface of 12 - 20, preferably 13 - 18 m.sup.2 /g, a maximum of the distribution of the grain sizes of between 500 and 1000 nm and a proportion of these grain sizes in the total distribution of between 35 and 65 %. This disazo pigment is obtained by isolating the pigment, after coupling, by stirring it out with alkali and, after having filtered it and washed it to neutrality, heating it to temperatures above 100.degree. C in a mixture of water and a solvent which is immiscible with water or miscible with water to a limited degree only.

Abstract translation: 由12 - 20特定表面表征的配方的双偶氮颜料，优选13 - 18 M2 / G，最大分配500和1000 NM之间的颗粒尺寸，以及总分布中这些颗粒尺寸的比例 35％至65％之间。 这种双偶氮颜料是通过在偶联后通过将其与碱反应来分离颜料而获得的，并且在将其过滤并将其洗涤至中性后，将其加热至高于100℃的水和溶剂的混合物中，所述混合物是不混溶的 用水或与水混合在一定程度上。