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    • 1. 发明授权
    • Water-soluble fibre-reactive phthalocyanine compounds
    • 水溶性纤维反应性酞菁化合物
    • US4576755A
    • 1986-03-18
    • US660266
    • 1984-10-15
    • Peter MischkeHermann Fuchs
    • Peter MischkeHermann Fuchs
    • C09B67/12C09B47/04C09B62/517C09B47/28C09B47/30
    • C09B62/517
    • Water-soluble fiber-reactive phthalocyanine compounds of the general formula (1) ##STR1## in which Pc denotes the radical of metal-free or metal-containing phthalocyanine, with the sulfonic acid or sulfonamide groups being bonded in the 3-positions of the aromatic rings of the phthalocyanine, R.sub.1 and R.sub.2 each denote a hydrogen atom or an alkyl group of 1-6 carbon atoms and which can be substituted by methoxy, ethoxy, propoxy, C.sub.2 H.sub.5 --O--C.sub.2 H.sub.4 --O--, cyano, acetylamino, carboxyl, HO.sub.3 S--, H.sub.2 O.sub.3 P--, phenyl, methylphenyl, methoxyphenyl, dimethylamino, diethylamino, .beta.-hydroxyethylamino, .beta.-hydroxyethoxy, N-phenylureido, N-alkyl.sub.C.sbsb.1.sub.-C.sbsb.4 ureido or N-cycloalkylureido groups or an allyl, 2-methallyl, crotyl or cycloalkyl group, and R.sub.1 and R.sub.2, together with the nitrogen atom, can represent the radical of a heterocyclic saturated or unsaturated ring, or R.sub.1 and R.sub.2 represent a phenyl radical which can be substituted by methyl, ethyl, methoxy, ethoxy, carboxyl or sulfonic acid groups, R.sub.3 denotes a hydrogen atom or an alkyl group of 1 to 4 carbon atoms and which can be substituted by hydroxyl or carboxyl groups, X represents a hydrogen atom or an alkyl or alkoxy group of 1 to 4 carbon atoms, Y represents the vinyl group or the grouping of the formula --CH.sub.2 --CH.sub.2 --Z in which Z denotes an inorganic or organic radical which can be eliminated under alkaline conditions, a represents a number between 0 and 2, b represents a number between 0 and 2 and c represents a number between 1.7 and 2.6, with the proviso that the sum of a, b and c is at most 4, a process for their preparation, and their use for dyeing wool, silk, polyamide fibers, leather or materials containing hydroxyl groups.
    • 通式(1)的水溶性纤维反应性酞菁化合物(1)其中Pc表示无金属或含金属酞菁的基团,磺酸或磺酰胺基团键合在3- 酞菁的芳环的位置R1和R2各自表示氢原子或1-6个碳原子的烷基,可以被甲氧基,乙氧基,丙氧基,C2H5-O-C2H4-O-,氰基, 乙酰氨基,羧基,HO3S-,H2O3P-,苯基,甲基苯基,甲氧基苯基,二甲基氨基,二乙基氨基,β-羟乙基氨基,β-羟基乙氧基,N-苯基脲基,N-烷基C1-C4脲基或N-环烷基脲基或烯丙基2-甲代烯丙基, 巴豆基或环烷基,R 1和R 2与氮原子一起可以表示杂环饱和或不饱和环的基团,或R 1和R 2表示可被甲基,乙基,甲氧基,乙氧基,羧基取代的苯基 或磺酸基,R 3表示氢 原子或1〜4个碳原子的烷基,可以被羟基或羧基取代,X表示氢原子或1〜4个碳原子的烷基或烷氧基,Y表示乙烯基或 式-CH2-CH2-Z,其中Z表示在碱性条件下可以除去的无机或有机基团,a表示0和2之间的数字,b表示0和2之间的数字,c表示1.7和2.6之间的数字 ,条件是a,b和c的总和最多为4,其制备方法及其用于染色羊毛,丝绸,聚酰胺纤维,皮革或含有羟基的材料的使用。
    • 2. 发明授权
    • Water-soluble disazo compounds suitable as fiber-reactive dyestuffs
    • US4430259A
    • 1984-02-07
    • US318112
    • 1981-11-04
    • Peter MischkeHermann FuchsFritz Meininger
    • Peter MischkeHermann FuchsFritz Meininger
    • C09B62/453C09B62/513C09B62/533D06P1/38D06P3/10
    • C09B62/453C09B62/513
    • Water-soluble disazo compounds, which can be used as fiber reactive dyestuffs and correspond to the general formula ##STR1## in which Y is vinyl or --CH.sub.2 --CH.sub.2 --Z, Z being sulfato, phosphato, halogen or hydroxy;D is phenylene or phenylene substituted by 1 or 2 radicals selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, chlorine, bromine, fluorine, carboxy, nitro and sulfo, orD is naphthylene or naphthylene substituted by 1 or 2 radicals selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, chlorine, bromine, fluorine, carboxy and sulfo;E is 1,4-phenylene or 1,4-naphthylene, or 1,4-phenylene or 1,4-naphthylene substituted by 1 or 2 radicals selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, ureido, lower alkanoylamino, chlorine, bromine, carboxy and sulfo;A is ethylene of the formula --CH.sub.2 --CH.sub.2--, or ethyleneoxy of the formula--CH.sub.2 --CH.sub.2 --O--, or propylene of the formula --CH.sub.2 --CH.sub.2 --CH.sub.2 --, or is of the formula ##STR2## wherein X is hydroxy, lower alkanoylamino, halogen, sulfato or phosphato, or is ##STR3## M is hydrogen, a metal or the equivalent of a metal; R.sup.1 is hydrogen, lower alkyl, lower alkenyl or lower alkyl substituted by hydroxy or phenyl or by both, or is alkyl of from 2 to 4 carbon atoms substituted by acetoxy, propionyloxy or phenylsulfonyloxy, or is cyanoalkyl of from 2 to 4 carbon atoms in the alkyl, or is carboxyalkylene, carbonamidoalkylene or carbalkoxyalkylene, the alkyl or aklylene moiety being in each case of from 1 to 4 carbon atoms, or is halogenoethyl or a group of the formula --A--SO.sub.3 M, A and M being as defined above;R.sup.2 is hydrogen, lower alkyl, lower alkoxy, halogen, lower alkanoylamino, ureido or trifluoromethyl; andR.sup.3 is hydrogen, lower alkyl, lower alkoxy or halogen.These disazo compounds can be prepared in a manner which is in itself known by reacting the diazo and coupling components which are evident from the formula (1). They serve as dyestuffs for dyeing and printing fibers which contain hydroxyl and/or cabonamide groups, such as cellulose fibers, wool or synthetic polyamide fibers, or leathers.
    • 3. 发明授权
    • Water-insoluble monoazo-dyestuffs for synthetic fibrous materials
    • 用于合成纤维材料的水不溶性单偶氮染料
    • US4160764A
    • 1979-07-10
    • US894177
    • 1978-04-06
    • Peter MischkeErwin FleckensteinReinhard Mohr
    • Peter MischkeErwin FleckensteinReinhard Mohr
    • C09B29/08C09B31/043C09B29/26C09B31/08
    • C09B29/0834C09B31/043
    • Azo-dyestuff of the formula ##STR1## in which D represents nitrophenylene, ##STR2## DINITRO-PHENYLENE, NITRO-CYANO-PHENYLENE, NITRO-CHLORO-PHENYLENE, NITRO-BROMO-PHENYLENE, TRICHLORO-PHENYLENE, NITRO-DICHLORO-PHENYLENE, DINITRO-CHLORO-PHENYLENE, DINITRO-CYANO-PHENYLENE, NITRO-BROMO-CYANO-PHENYLENE, DINITRO-BROMO-PHENYLENE, PHENYLAZO-PHENYLENE, ##STR3## R represents hydrogen, chlorine, lower alkyl, lower alkoxy, --O--CH.sub.2 --CN, --NH--CO--lower alkyl, --NH--COO lower alkyl or ##STR4## n stands for the integer 1 or 2, X represents cyano, --CO--NH.sub.2 or --COO-lower alkyl, R.sub.1 represents hydrogen, lower alkyl, lower alkylene-OH, lower alkylene-CN, lower alkylene-OCO-lower alkyl or lower alkenyl, and R.sub.2 represents lower alkyl, lower alkylene-O-CO-lower alkyl or lower alkylene-COO-lower alkyl, said dyestuffs being suitable for the dyeing or printing of synthetic fibrous materials, such as fibers of cellulose-di-, -21/2- or -triacetat, polyamides, polyurethanes, polyolefines, polycarbonates and particularly of linear polyesters, the dyeings or prints obtained being distinguished by a very good build up, tinctorial strength and a series of very good fastness properties.
    • 其中D表示硝基亚苯基,偶氮苯基,硝基 - 苯基,硝基 - 苯基,硝基 - 溴 - 苯基,三氯苯基,硝基 - 二氯苯,苯并噻吩, 四甲基氯苯,十一烷基 - 苯乙烯,硝基 - 溴 - 氰基 - 苯乙烯,十一烷基 - 苯乙烯,苯基 - 苯乙烯,<图像> <图像>&lt; IMA&gt;&gt;&gt; R代表氢,氯, 低级烷基,低级烷氧基,-O-CH 2 -CN,-NH-CO-低级烷基,-NH-COO低级烷基或n代表整数1或2,X代表氰基,-CO-NH 2或 - 低级烷基,R 1表示氢,低级烷基,低级亚烷基-OH,低级亚烷基-CN,低级亚烷基-OCO-低级烷基或低级烯基,R 2表示低级烷基,低级亚烷基-O-CO-低级烷基或低级烷基 亚烷基-COO-低级烷基,所述染料适用于合成纤维材料的染色或印刷,例如纤维素二 - ,二 - 或2-三乙酸纤维,聚酰胺,聚氨酯,聚烯烃,聚碳酸酯 特别是线性聚酯,所获得的染色或印花的特征在于非常好的聚集度,着色强度和一系列非常好的坚牢度性质。
    • 5. 发明授权
    • Process for producing concentrated aqueous solutions of anionic azo dyes
    • 阴离子偶氮染料浓缩水溶液的制备方法
    • US5508389A
    • 1996-04-16
    • US30280
    • 1993-03-26
    • Peter MischkeKurt HohmannEckhard SchwabManfred Sittig
    • Peter MischkeKurt HohmannEckhard SchwabManfred Sittig
    • C09B41/00C09B67/26D06P1/384
    • C09B41/003C09B41/001C09B67/0073
    • If highly concentrated aqueous solutions of azo dyes are prepared directly by diazotization and coupling reactions, appreciable difficulties generally result as a consequence of the fact that the diazotization and coupling reactions give rise to viscous phases which lead to stirring problems in the reaction apparatus used, which in turn results in an incomplete synthesis. The novel process for preparing concentrated aqueous dye solutions of an anionic dye in an aqueous medium overcomes this disadvantage by carrying out the diazotization of the aromatic amine diazo component and/or the coupling reaction between the diazonium salt and the coupling component in the presence of an auxiliary which exerts a viscosity-reducing effect on pasty phases. Examples of such auxiliaries are optionally alkyl-substituted naphthalenesulfonic acid-formaldehyde condensation products, ligninsulfonates, polyacrylates and copolymers of maleic anhydride and methacrylic acid or acrylic acid.
    • PCT No.PCT / EP91 / 01830 Sec。 371日期1993年3月26日 102(e)1993年3月26日PCT PCT 1991年9月25日PCT公布。 出版物WO92 / 06140 日期:1992年04月16日。如果通过重氮化和偶联反应直接制备偶氮染料的高度浓缩水溶液,则由于重氮化和偶联反应产生粘度相导致搅拌问题,导致明显的困难 在所用的反应装置中,这又导致不完全的合成。 在水性介质中制备阴离子染料的浓缩染料水溶液的新方法通过在芳族胺重氮组分的重氮化和/或重氮盐和偶联组分之间的偶联反应在 辅助剂对糊状相施加粘度降低作用。 这种助剂的实例是任选烷基取代的萘磺酸 - 甲醛缩合产物,木质素磺酸盐,聚丙烯酸酯和马来酸酐和甲基丙烯酸或丙烯酸的共聚物。
    • 6. 发明授权
    • Process for the reduction of heavy metal ions in excess from aqueous
synthesis solutions of water soluble heavy metal complex dyestuffs
    • 从水溶性重金属络合物染料的水合物溶液中还原过量的重金属离子的方法
    • US4963660A
    • 1990-10-16
    • US238359
    • 1988-08-30
    • Uwe MrotzeckPeter MischkeGunther SchwaigerWerner RussManfred Sittig
    • Uwe MrotzeckPeter MischkeGunther SchwaigerWerner RussManfred Sittig
    • C09B45/01C09B67/54
    • C09B67/0096C09B45/01
    • Free radical heavy metal ions in water-soluble heavy metal complex dyestuffs are removed from the synthesis solution of the heavy metal complex dyestuff by means of a compound or several of the compounds mentioned below:(a) saturated and unsaturated fatty acids having about 8 to 18 carbon atoms and water-soluble salts thereof;(b) the monoesters and diesters of orthophosphoric acid and salts thereof corresponding to the general formula (1a) and (1b) ##STR1## in which R denotes a saturated or unsaturated aliphatic radical having about 8 to 18 carbon atoms and M stands for a hydrogen atom or a salt-forming, water-solubilizing metal;(c) aliphatic sulfonic acids and water-soluble salts thereof corresponding to the general formula (2)R--SO.sub.3 M (2) in which R and M have the abovementioned meanings;(d) aliphatic phosphonic acids and monoesters thereof and also water-soluble salts thereof corresponding to the general formulae (3a) and (3b) ##STR2## in which R and M have the abovementioned meanings; (e) malonic acid and water-soluble salts thereof;(f) trimercapto-s-triazine, 2-aminobenzoic acid, 8-hydroxyquinoline and water-soluble salts of these compounds;(g) water-soluble sulfides, in particular alkali metal sulfides;(h) functionalized water-insoluble polymers which react with metal ions by the ion-exchanger principle or form metal chelate complexes.Using these compounds, the excess heavy metal ions are precipitated out of the synthesis solution or separated off, without the heavy metal ions bound as a complex in the dye being attached.
    • 通过化合物或下列几种化合物,从重金属络合物染料的合成溶液中除去水溶性重金属络合物染料中的自由基重金属离子:(a)饱和和不饱和脂肪酸,其具有约8〜 18个碳原子及其水溶性盐; (b)对应于通式(1a)和(1b)的正磷酸及其盐的单酯和二酯及其盐,其中R表示具有约8至18个碳原子的饱和或不饱和脂肪族基团,M代表 氢原子或成盐的水溶性金属; (c)对应于通式(2)R-SO 3 M(2)的脂族磺酸及其水溶性盐,其中R和M具有上述含义; (d)脂肪族膦酸及其单酯,以及对应于通式(3a)和(3b)的化合物的水溶性盐,其中R和M具有上述含义; (e)丙二酸及其水溶性盐; (f)这些化合物的三聚巯基-s-三嗪,2-氨基苯甲酸,8-羟基喹啉和水溶性盐; (g)水溶性硫化物,特别是碱金属硫化物; (h)通过离子交换原理与金属离子反应的官能化水不溶性聚合物,或形成金属螯合物。 使用这些化合物,过量的重金属离子从合成溶液中沉淀出来或分离出来,而不附着染料中重金属离子作为络合物结合。
    • 7. 发明授权
    • Water-soluble monoazo compounds containing a N-(sulfoalkyl)-aniline
coupling component and a fiber-reactive group of the vinylsulfonyl
series in the phenyl or benzothiazole diazo component, suitable as
fiber-reactive dyestuffs
    • US4652634A
    • 1987-03-24
    • US819988
    • 1986-01-15
    • Peter MischkeHermann Fuchs
    • Peter MischkeHermann Fuchs
    • C09B62/45C09B62/453C09B62/51C09B62/513C09B62/527C09B62/53D06P1/384D06P3/60
    • C09B62/513C09B62/45C09B62/453C09B62/51
    • A water-soluble azo compund of formula ##STR1## in which Y is vinyl or --CH.sub.2 --CH.sub.2 --Z in which Z is chlorine, bromine, fluorine, lower alkanoyloxy, benzoyloxy, sulfobenzoyloxy, benzenesulfonyloxy, toluenesulfonyloxy, lower alkylsulfonylamino, arylsulfonylamino, phenoxy, dialkylamino, each alkyl being of from 1 to 4 carbon atoms, thiosulfato, phosphato or sulfato;n is the number zero or 1;D is phenylene unsubstituted or substituted by one or two substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, lower alkanoylamino, chlorine, bromine, fluorine and carboxy; by one nitro substituent; by one sulfo substituent; by one substituent of the formula Y--SO.sub.2 --(CH.sub.2).sub.n -- in which n is 1; by a plurality of substituents selected from the group consisting of said one or two substituents, said one nitro substituent, said one sulfo substituent and said one substituent of the formula Y--SO.sub.2 --(CH.sub.2).sub.n --; ornaphthylene substituted or mono- or disubstituted by sulfo; orthe benzothiazol-2-yl radical in which the group Y--SO.sub.2 --(CH.sub.2).sub.n -- is bonded to its carbocyclic ring, or said radical in which the benzene ring is additionally substituted by lower alkyl, lower alkoxy, hydroxy, lower alkanoylamino, nitro, chlorine, bromine or sulfo; R.sup.1 is hydrogen, lower alkyl, lower alkenyl, lower alkyl substituted by phenyl or hydroxy or by both, lower alkyl substituted by phenyl which is substituted by substituents selected from the group consisting of methyl, methoxy and chlorine, or by said substituted phenyl and hydroxy, or is alkyl of from 2 to 4 carbon atoms substituted by acetoxy, propionyloxy or phenylsulfonyloxy or by cyano, or is alkyl of from 1 to 4 carbon atoms substituted by carboxy or carbonamido or carbalkoxy of from 1 to 4 carbon atoms in the alkyl moiety, or is halogenoalkyl of 2 or 3 carbon atoms or is lower halogenoalkenyl, or is a group of the formula --A--SO.sub.3 M;A is ethylene, or propylene of the formula ##STR2## in which X is hydroxy, acetoxy, propionyloxy or phenylsulfonyloxy or is a halogen;R.sup.2 is hydrogen, lower alkyl, lower akloxy unsubstituted or substituted by hydroxy, acetoxy, carboxy, carbamoyl, cyano or halogen, or is halogen or trifluormethyl;R.sup.3 is hydrogen, lower alkyl, lower alkoxy unsubstituted or substituted by hydroxy, acetoxy, carboxy, carbamoyl, cyano or halogen, or is halogen;M is hydrogen or an alkali metal.The new azo compounds are suitable as dyestuffs, in particular for dyeing or printing fibers which contain hydroxy groups or carbonamide groups, or leathers.
    • 8. 发明授权
    • Basic azo amino-phenylene dyestuffs
    • 碱性偶氮氨基亚苯基染料
    • US4028321A
    • 1977-06-07
    • US491175
    • 1974-07-23
    • Erwin FleckensteinPeter Mischke
    • Erwin FleckensteinPeter Mischke
    • C09B27/00C09B44/00C09B44/04C09B44/10C09B29/06C09B29/08C09B29/36C09B43/00
    • C09B44/10C09B44/04
    • A basic dyestuff of the formula ##STR1## wherein R.sub.1 is hydrogen, alkyl of 1 to 5 carbon atoms, hydroxyalkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 carbon atoms in the alkyl moiety or chloroalkyl of 1 to 4 carbon atoms, R'.sub.2 is phenyl or naphthyl or is phenyl or naphthyl substituted by alkyl of 1 to 4 C-atoms and/or alkoxy of 1 to 4 carbon atoms or nitro or cyano and/or chlorine, R.sub.5 is an optionally substituted alkyl or aralkyl radical, R.sub.6 and R.sub.7 being the same or different, each is hydrogen or an alkyl radical or, both together, substituents which complete to form an anellated aromatic ring, Y is a bivalent atom or a bivalent group necessary to complete a 5- or 6-ring, R.sub.10 is hydrogen, fluorine, bromine or chlorine or alkyl of 1 to 4 C-atoms and X.sup..sup.-`is an anion, which are suitable for the dyeing or printing of tannined cellulose fibers, silk, leather or fully synthetic fibers, such as acetate silk, polyamide fibers or acid modified polyamide or polyester fibers, especially of fibers which contain polyacrylonitrile or polyvinylidene cyanide. Their dyeings are in general very intense and have, for example, good fastnesses to light and to wetting processes, to chlorine and perspiration. They are resistant to a large degree to a change of the pH-value of the dyebath and can therefore be used both in a slightly acidic and in a strongly acidic bath. Wool is completely reserved by the dyestuffs under normal dyeing conditions.
    • 其中R 1为氢,1至5个碳原子的烷基,1至4个碳原子的羟基烷基,1至4个碳原子的烷基部分的氰基烷基或1个氯代烷基的基本染料 至4个碳原子,R'2是苯基或萘基,或是被1-4个碳原子的烷基和/或1-4个碳原子的烷氧基或硝基或氰基和/或氯取代的苯基或萘基,R5是任意的 取代的烷基或芳烷基,R 6和R 7相同或不同,各自为氢或烷基,或两者一起为完成形成Anellated芳环的取代基,Y为二价原子或完成 5-或6-环,R 10为氢,氟,溴或氯或1〜4个C原子的烷基,X 1'为阴离子,适用于染色或印花单宁纤维素纤维,丝绸, 皮革或全合成纤维,如醋酸丝,聚酰胺纤维或酸改性聚酰胺或聚酯纤维,特别是 含有聚丙烯腈或聚偏二氰乙烯的纤维。 它们的染色通常非常强烈,并且具有例如良好的耐光牢度和湿润过程,氯和汗水。 它们在很大程度上抵抗染浴的pH值的变化,因此可以在轻微酸性和强酸性浴中使用。 在正常染色条件下,羊毛完全由染料保留。