公开(公告)号：US4987221A

公开(公告)日：1991-01-22

申请号：US844858

申请日：1986-03-27

Applicant: Hasso Hertel ,  Klaus Hunger ,  Heinrich Frolich

Inventor： Hasso Hertel ,  Klaus Hunger ,  Heinrich Frolich

IPC: C09B35/02 ,  C07C67/00 ,  C07C241/00 ,  C07C245/20 ,  C09B35/08 ,  D06P1/12

CPC classification number: C09B35/08 ,  D06P1/12

Abstract: Bisdiazonium salts of the formula (1) ##STR1## in which R denotes a linear or branched alkyl or alkoxyalkyl radical having 3-5 carbon atoms and X.sup.- represents the radical of a strong acid or of a zinc chloride double salt, and a process for their preparation by diazotizing a 4,4'-diamino-3,3'-dialkoxybiphenyl of the formula (2) ##STR2## in which R has the meaning mentioned, in an aqueous, strong, non-oxidizing inorganic or organic acid at temperatures from about -10.degree. C. to about +40.degree. C. by means of an alkali metal nitrite, and precipitating the resulting bisdiazonium salts by adding an alkali metal chloride, bisulfate, monosulfonate of 1,5-naphthalenedisulfonic acid or tetrafluoroborate or zinc chloride.These salts are useful in dyeing and printing textile fiber materials by the methods of the ice color technique, using suitable coupling components; they are also useful for preparing photographic tracings by the methods of reprography.

Abstract translation: 式（1）的Biaziazonium盐其中R表示具有3-5个碳原子的直链或支链烷基或烷氧基烷基，X表示强酸或氯化锌双盐的自由基， （2）的4,4'-二氨基-3,3'-二烷氧基联苯的制备方法，其中R具有上述含义，在水，强，非 - 通过碱金属亚硝酸盐在约-10℃至约+ 40℃的温度下氧化无机或有机酸，并通过加入1,5-二甲基苯磺酸的碱金属氯化物，硫酸氢盐，单磺酸盐沉淀所得的双重氮盐， 萘二磺酸或四氟硼酸盐或氯化锌。 这些盐可用于通过使用合适的偶联组分的冰色技术的方法对纺织纤维材料进行染色和印花; 它们也可用于通过复制方法制备照相追踪。

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：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：US4150019A

公开(公告)日：1979-04-17

申请号：US396521

申请日：1973-09-12

Applicant: Heinrich Frolich ,  Joachim Ribka

Inventor： Heinrich Frolich ,  Joachim Ribka

IPC: C09B29/02 ,  C09B29/32 ,  C09B67/00 ,  D06P1/08 ,  C09B29/36 ,  D06P1/04 ,  D21H1/46

CPC classification number: C09B67/00 ,  C09B29/02 ,  C09B29/32 ,  D06P1/08

Abstract: Water insoluble yellow monoazo dyestuffs of the general formula 1 ##STR1## in which R.sub.1 represents alkyl, cycloalkyl or aralkyl, X represents a carboxylic acid ester or a carboxylic acid amide, and Y.sub.1 and Y.sub.2 represent hydrogen, chlorine or bromine, alkyl or alkoxy, and method for their preparation. The dyestuffs are valuable pigments, which may be used for dyeing lacquers, lacquer forming agents, natural or synthetic resins and polymers and for printing textile fibrous materials or paper. They are distinguished by good rheological properties and they are fast to light, weather and migration. Moreover, they are resistant to heat and show color intensity and pure shades.

Abstract translation: 通式1的水不溶性黄色单偶氮染料，其中R1代表烷基，环烷基或芳烷基，X代表羧酸酯或羧酸酰胺，Y1和Y2代表氢，氯或溴，烷基或烷氧基 ，及其制备方法。 染料是有价值的颜料，可用于染色漆，成漆剂，天然或合成树脂和聚合物，以及印刷纺织纤维材料或纸张。 它们具有良好的流变特性，具有光照，天气和迁移快等特点。 此外，它们具有耐热性和显色性和纯色调。

公开(公告)号：US5128454A

公开(公告)日：1992-07-07

申请号：US482692

申请日：1990-02-21

Applicant: Heinrich Frolich

Inventor： Heinrich Frolich

IPC: C09B67/48 ,  C09B63/00 ,  C09B67/00 ,  C09B67/10 ,  C09B67/20 ,  C09C3/08 ,  D21H21/28

CPC classification number: C09B67/0029 ,  C09B67/0015 ,  Y10S534/04

Abstract: The invention relates to a novel crystallographic modification (.beta.-modification) of the pigment of the formula I ##STR1## The .beta.-modification shows reflections in the Cu-K.sub..alpha. radiation X-ray diffraction spectrum at the following diffraction angles 2.theta. (accuracy .+-.0.2.degree.): at 21.95.degree. a maximum of high intensity, at 5.40.degree., 7.30.degree., 10.85.degree., 14.50.degree. and 27.60.degree. maxima of medium intensity and at 10.05.degree., 12.80.degree., 16.40.degree., 17.95.degree., 24.65.degree. and 25.80.degree. maxima of low intensity.The .beta.-modification is obtainable by coupling diazotized N-(3-amino-4-methylbenzoyl)-sulfanilic acid in an aqueous medium in the presence or absence of an organic solvent onto alkali-dissolved 2-hydroxy-4'-methoxy-3-naphthanilide and laking the coupling product by adding a calcium salt, at least one cation-active surfactant having been added at the latest prior to laking, and heating an aqueous suspension of the laked azo dye at a temperature of 130.degree. to 180.degree. C.The .beta.-modification is suitable for pigmenting printing inks, surface coatings, plastic compositions, filaments and paper, in particular for pigmenting polystyrene, copolymers based on polystyrene, polyolefins, copolymers of polyolefins and polyvinyl chloride.

Abstract translation: 本发明涉及式I的颜料的新型晶体学修饰（β-改性）（I）图像β修饰显示了以下Cu-Kα辐射X射线衍射光谱中的反射 衍射角2θ（精度+/- 0.2°）：在21.95°时，最大高强度，中等强度的5.40°，7.30°，10.85°，14.50°和27.60°，最大值为10.05°，12.80°，16.40° DEG，17.95°，24.65°和25.80°最大值。 在有机溶剂存在或不存在下，将重氮化的N-（3-氨基-4-甲基苯甲酰基） - 磺胺酸在水性介质中偶联到碱溶解的2-羟基-4'-甲氧基-3 - 萘磺酸盐，并且通过加入钙盐，至少一种最近在浸渍之前加入的阳离子活性表面活性剂并在130-180℃的温度下加热沉淀的偶氮染料的水悬浮液， 该β-改性适用于着色印刷油墨，表面涂料，塑料组合物，长丝和纸张，特别是用于着色聚苯乙烯，基于聚苯乙烯的共聚物，聚烯烃，聚烯烃和聚氯乙烯的共聚物。

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：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。