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    • 1. 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.
    • 2. 发明授权
    • Dyestuff preparations for dyeing and printing natural and synthetic
polyamide fibre materials
    • 用于染色和印花天然和合成聚酰胺纤维材料的染料制剂
    • US4074967A
    • 1978-02-21
    • US526389
    • 1974-11-22
    • Hermann FuchsGustav KapaunFritz Meininger
    • Hermann FuchsGustav KapaunFritz Meininger
    • D06P3/04C09B11/26C09B67/24D06P3/06D06P3/26D06P3/32C09B11/00D06P3/24
    • D06P3/32C09B11/26C09B67/0072D06P3/06Y10S8/917Y10S8/924
    • A highly water-soluble composition for the dyeing or printing of native or synthetic polyamide fibres consisting essentially of (a) 10 to 99 parts by weight of at least one dyestuff ##STR1## IN WHICH X represents hydroxy, methyl, ethyl, methoxy or ethoxy, and Y represents hydrogen or methyl, and (b) 0.5 to 90 parts by weight of an auxiliary agent of the group consisting of a polyglycol of an average molecular weight from 3000 to 20 000, a polyglycolether (containing 15 to 30 ether groups) of a fatty alcohol of 8 to 20 carbon atoms, an alkali metal salt of a dialkylnaphthalene sulfonic acid (alkyl C.sub.1 -C.sub.6), a methyltauride of a saturated or unsatruated fatty acid of 8 to 20 carbon atoms, and an isethionate of a saturated or unsaturated fatty acid of 8 to 20 cabron atoms, and mixtures thereof, said composition being also suitable for the dyeing or printing of the said polyamide fibres in deep shades.
    • 用于染色或印刷天然或合成聚酰胺纤维的高度水溶性组合物,其基本上由(a)10至99重量份的至少一种染料组成,其中X表示羟基,甲基,乙基,甲氧基或乙氧基 ,Y表示氢或甲基,(b)0.5〜90重量份的平均分子量为3000〜20000的聚乙二醇的辅助剂,聚乙二醇醚(含有15〜30个醚基) 的碳原子数为8〜20的脂肪醇,二烷基萘磺酸(烷基C1-C6)的碱金属盐,碳原子数为8〜20的饱和或不饱和脂肪酸的甲基牛磺酸和饱和或不饱和脂肪酸的羟乙基磺酸盐, 8至20个卡培酮原子的不饱和脂肪酸及其混合物,所述组合物也适用于以深色调染色或印刷所述聚酰胺纤维。
    • 3. 发明授权
    • Monoazo reactive dyestuffs
    • 单偶氮活性染料
    • US4036825A
    • 1977-07-19
    • US730428
    • 1976-10-07
    • Hermann FuchsFritz Meininger
    • Hermann FuchsFritz Meininger
    • C09B62/51C09B29/06C09B29/26C09B29/30C09B29/38
    • C09B62/51
    • Fiber-reactive monoazo dyestuffs which, in form of free acids, correspond to the general formula ##STR1## in which Z represents one of the groupings--CH.sub.2 --CH.sub.2 --OSO.sub.3 Hor--CH=CH.sub.2a stands for benzene, naphthalene or pyrazole unsubstituted or substituted by alkyl, alkoxy or by a phenyl group which is unsubstituted or may be substituted by alkyl, alkoxy, hydroxy, cyano, nitro, sulfonic acid, sulfonic acid amide, carboxylic acid amide, chlorine, bromine, carboxylic acid, acetylamino, benzoylamino, trifluoromethyl, carbalkoxy, B-sulfatoethylsulfonyl or vinylsulfonyl, and wherein, if A represents a benzene or naphthalene radical the azo group and the amino group of the formula --NR.sub.1 R.sub.2 standing in ortho or para position to each other, and if A is pyrazole, the group --NR.sub.1 R.sub.2 is standing in 5-position and the azo group in 4-position of the pyrazole, R.sub.1 and R.sub.2 are different or the same and each stand for hydrogen or alkyl which may be substituted by chlorine, hydroxy, cyano, alkanoyloxy, benzoyloxy, nitrobenzoyloxy, chlorobenzoyloxy, phenyl or phenyl substituted by alkyl, alkoxy, alkyl-sulfone, sulfonic acid, sulfonic acid amide, carboxylic acid amide, nitro, trifluoromethyl, chlorine or bromine, which are suitable for the dyeing and printing of native and regenerated cellulose fibers, but especially advantageous for dyeing or printing fibers or fabrics of nitrogen - containing fibers of native or synthetic origin.
    • 以游离酸形式存在的纤维反应性单偶氮染料对应于通式“IMAGE”,其中Z代表一组-CH 2 -CH 2 OSO 3 H或-CH = CH 2 A代表未取代的苯,萘或吡唑, 羟基,氰基,硝基,磺酸,磺酸酰胺,羧酸酰胺,氯,溴,羧酸,乙酰氨基,苯甲酰基氨基,苯甲酰氨基, 三氟甲基,烷氧羰基,B-硫酸基乙基磺酰基或乙烯基磺酰基,并且其中如果A表示苯或萘基,则偶氮基和式-NR1R2的氨基彼此相邻或对位,如果A是吡唑,则 基团-NR1R2位于5位,吡唑R 1和R 2的4位的偶氮基不同或相同,各代表氢或可被氯,羟基,氰基,烷酰氧基,苯甲酰氧基取代的烷基 ,n 苯甲酰氧基,氯苯甲酰氧基,苯基或被烷基,烷氧基,烷基砜,磺酸,磺酸酰胺,羧酸酰胺,硝基,三氟甲基,氯或溴取代的苯基,适用于天然和再生纤维素纤维的染色和印花 ,但对于染色或印刷天然或合成来源的含氮纤维的纤维或织物特别有利。
    • 6. 发明授权
    • Phenyl-azo-phenyl dyestuffs
    • 苯偶氮苯基染料
    • US4134887A
    • 1979-01-16
    • US852043
    • 1977-11-16
    • Hermann FuchsGustav KapaunFritz Meininger
    • Hermann FuchsGustav KapaunFritz Meininger
    • C09B62/51C09B29/08D06P1/384D06P3/10D06P3/66
    • C09B62/51
    • Fiber-reactive azo dyestuffs are obtained by diazotizing an amine of the formula ##STR1## in which Z stands for--CH.sub.2 -CH.sub.2 --A or--CH.dbd.CH.sub.2in which A is N,N-dialkylamino with 1 to 4 carbon atoms in each alkyl moiety or is chlorine, bromine, sulfato, thiosulfato, phosphato and acetoxy it with an azo component of the formulaH--B,in which B is ##STR2## wherein R is hydrogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, acetylamino, chlorine or bromine, R.sub.1 is hydrogen or alkyl with 1 to 4 carbon atoms unsubstituted or substituted by hydroxy or cyano, and R.sub.2 is lower alkyl with 1 to 4 carbon atoms unsubstituted or substituted by hydroxy or cyano, or is acetyl or benozyl. The new dyestuffs are especially suitable for dyeing and printing fiber materials, such as silk, wool, synthetic polyamide or polyurethane, and above all, native and regenerative cellulose. They possess a very high fiber reactivity so that they fix on the fiber material very rapidly even at low temperatures and are thus very suitable in continuous dyeing processes.
    • 纤维反应性偶氮染料是通过重氮化式为“IMAGE”的胺,其中Z代表-CH 2 -CH 2 -A或-CH = CH 2,其中A是N,每个具有1至4个碳原子的N-二烷基氨基 烷基部分或是氯,溴,硫酸根,硫代硫酸根,磷酸根和乙酰氧基,其与式HB的偶氮成分反应,其中B为其中R为氢,具有1至4个碳原子的烷基,具有1至4个碳原子的烷氧基 碳原子,乙酰氨基,氯或溴,R 1是氢或未被取代或被羟基或氰基取代的具有1至4个碳原子的烷基,R 2是未被取代或被羟基或氰基取代的具有1至4个碳原子的低级烷基,或者是乙酰基 或Benozyl。 新型染料特别适用于丝,羊毛,合成聚酰胺或聚氨酯等染色和印花纤维材料,尤其是天然纤维素和再生纤维素。 它们具有非常高的纤维反应性,使得即使在低温下它们也非常迅速地固定在纤维材料上,因此非常适合于连续染色过程。
    • 8. 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.
    • 9. 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。
    • 10. 发明授权
    • Water-soluble disazo compounds and new bis-(aminophenoxy)-ethane
compounds having fiber-reactive groups as the tetrazo components, and
use of the disazo compounds as dyestuffs
    • 具有纤维反应性基团作为双偶氮组分的水溶性双偶氮化合物和新的双 - (氨基苯氧基) - 乙烷化合物,以及使用双偶氮化合物作为染料
    • US4534908A
    • 1985-08-13
    • US535431
    • 1983-09-26
    • Hermann FuchsKlaus Filzinger
    • Hermann FuchsKlaus Filzinger
    • C09B62/01C09B62/44C09B62/513D06P3/10D06P3/66C07C141/16C07C93/14
    • C09B62/4401C09B62/513
    • Water-soluble disazo compounds of the formula (1) ##STR1## and diamino compounds serving as starting compounds (tetrazo components), of the formula (4) ##STR2## in which the formulae moieties occurring twice, namely Z, K and X, in each case have a meaning identical to one another and the groups Z are bonded to the two benzene nuclei in each case in the ortho- or in each case in the para-position relative to the ethylenedioxy substituent, and the azo groups or amino groups and the groups Z in the benzene nuclei are in each case bonded in the meta-position relative to one another and K is the radical of a coupling component containing a sulfato, carboxy or sulfo group, X denotes a hydrogen atom or a fiber-reactive group and Z is a group of the formula --SO.sub.2 --CH.dbd.CH.sub.2 or --SO.sub.2 --CH.sub.2 --CH.sub.2 --Y in which Y denotes a radical which can be eliminated in aqueous medium under alkaline or acidic conditions or the hydroxy group.Disazo compounds of the formula (1) can be used as dyestuffs having fiber-reactive properties for dyeing, for example, cellulose fiber material and wool and be prepared by tetrazotizing diamines of the formula (4) and coupling with coupling components evident from the formula (1).Diamino compounds of the formula (4) are obtained by acetylating a 1,2-di-(o- or p-aminophenoxy)-ethane, chlorosulfonating this bis-acetylamino compound and reducing the sulfonyl chloride groups to sulfinic acid groups, which are then oxyethylated to give .beta.-hydroxyethylsulfonyl groups, which, after deacetylation of acetylamino groups, can be converted in a manner which is in itself known into one of the abovementioned groups Z, for example into the .beta.-sulfatoethylsulfonyl group by means of a sulfating agent.
    • 式(1)的水溶性双偶氮化合物(1)和作为起始化合物的二氨基化合物(双偶氮组分),式(4)的化合物(4)其中式部分发生两次,即 Z,K和X各自具有彼此相同的含义,并且基团Z在每种情况下在邻 - 或每种情况下都相对于亚乙二氧基取代基的对位键合到两个苯核上,并且 苯核中的偶氮基或氨基和基团Z各自以相对于彼此的间位键合,K是含有硫酸基,羧基或磺基的偶合成分的基团,X表示氢 原子或纤维反应性基团,Z是式-SO 2 -CH = CH 2或-SO 2 -CH 2 -CH 2 -Y的基团,其中Y表示可在碱性或酸性条件下在水性介质中除去的基团,或 羟基。 式(1)的双偶氮化合物可用作具有染色的纤维反应性的染料,例如纤维素纤维材料和羊毛,并且可通过将式(4)的二胺四唑化合并与式 (1)。 式(4)的二氨基化合物通过乙酰化1,2-二 - (邻 - 或对氨基苯氧基) - 乙烷,氯磺化该双乙酰氨基化合物并将磺酰氯基团还原为亚磺酸基团而获得,然后将其 乙氧基化得到β-羟基乙基磺酰基,其在乙酰氨基脱乙酰后可以以本身已知为上述基团Z之一的方式转化,例如通过硫酸化转化成β-磺基乙基磺酰基 代理商