公开(公告)号：US5256776A

公开(公告)日：1993-10-26

申请号：US936138

申请日：1992-08-27

Applicant: Thomas Beck ,  Werner H. Russ ,  Hartmut Springer ,  Marcus Banfer

Inventor： Thomas Beck ,  Werner H. Russ ,  Hartmut Springer ,  Marcus Banfer

IPC: C07D487/22 ,  C09B62/44 ,  C09B62/517 ,  C09B62/016 ,  D06P1/38 ,  D06P3/10 ,  D06P3/66

CPC classification number: C09B62/517 ,  C09B62/4418

Abstract: Water-soluble phthalocyanine dyestuffs, processes for their preparation and their use Phthalocyanine dyestuffs, in particular copper phthalocyanine and nickel phthalocyanine dyestuffs, which contain one or more groups of the formula define below ##STR1## or one or more carboxy groups, or both groups, and which furthermore can have one or more sulfo groups, customary sulfonamide groups and/or groups of the general formula defined below ##STR2## dye materials containing hydroxy and/or carboxamide groups, in particular fiber materials, such as, for example, cellulose fiber materials, wool and polyamide fibers, in deep-colored, fast, mainly green shades. In the formulae:R.sup.1 and R.sup.2 are both, independently of one another, hydrogen or a lower optionally substituted aliphatic radical, G is lower alkylene, or is phenylene, which can be substituted by lower alkyl, lower alkoxy, halogen, sulfo, carboxy and/or nitro, or the grouping --N(R.sup.1)--G--N(R.sup.2)-- forms the bivalent radical of a saturated heterocyclic ring, W is halogen, lower alkoxy, aryloxy, sulfo, phenylsulfonyl, lower alkylsulfonyl or an optionally substituted amino group, or is a radical of the formula --N(R.sup.3)--A--(Y--Z).sub.m, where R.sup.3, A, Y, Z and m have the meaning given below, A is an aromatic carbocyclic or aromatic heterocyclic radical or an alkylene radical, which can be interrupted by 1 or 2 hetero groups, or is an alkylenephenylene radical or the bivalent radical of a saturated heterocyclic ring containing two N atoms, Y, in the case where A is an aromatic radical, is a direct bond or a carbamoyl-alkylene group or a methylene, ethylene, methylamino or .beta.-cyanoethyl-amino group, or Y is lower alkylene, and in this case A necessarily is a direct bond and m is 2, Z is a fiber-reactive group of the vinylsulfone series, m is the number 1 or 2 and R.sup.3 is hydrogen or lower alkyl.

公开(公告)号：US5055565A

公开(公告)日：1991-10-08

申请号：US570033

申请日：1990-08-20

Applicant: Hartmut Springer ,  Manfred Kuhn ,  Werner H. Russ ,  Ludwig Schlafer

Inventor： Hartmut Springer ,  Manfred Kuhn ,  Werner H. Russ ,  Ludwig Schlafer

IPC: C09B62/513

CPC classification number: C09B62/513

Abstract: Compounds according to the general formula ##STR1## in which: D is phenyl, optionally substituted by sulfo, carboxy, alkyl, alkoxy, alkanoylamino and/or chlorine, at least by sulfo or carboxy, or is a sulfosubstituted naphthyl;E is 1,4-phenylene, substituted by alkyl, alkoxy, alkanoylamino, ureido and/or chlorine, or is 1,4-naphthylene optionally substituted by sulfo;K is 1,4-phenylene, substituted by alkyl, alkoxy, alkanoylamino, ureido and/or chlorine, or is a 1,4-naphthylene optionally substituted by sulfo;A is a direct bond or is methylene or is a bivalent amino, alkylamino or (.beta.-cyanoethyl)-amino group;Y is vinyl or .beta.-chloroethyl.These compounds are fiber-reactive and have dyestuff properties and dye hydroxy--and/or carboxamido-containing material, in particular fiber material such as wool and, in particular cellulose, in strong color-fast shades.

Abstract translation: 根据通式DNN [（4）E（1）] NN + TR 的化合物，其中：D是任选被磺基，羧基，烷基，烷氧基，烷酰基氨基和/或氯取代的苯基，至少通过磺基 或羧基，或是磺基取代的萘基; E是由烷基，烷氧基，烷酰基氨基，脲基和/或氯取代的1,4-亚苯基，或是任选被磺基取代的1,4-亚萘基; K是由烷基，烷氧基，烷酰基氨基，脲基和/或氯取代的1,4-亚苯基，或是任选被磺基取代的1,4-亚萘基; A是直接键或亚甲基或是二价氨基，烷基氨基或（β-氰基乙基） - 氨基; Y是乙烯基或β-氯乙基。 这些化合物是纤维反应性的并且具有染料性质和染料含羟基和/或羧酰氨基的材料，特别是纤维材料如羊毛，特别是纤维素，具有强烈的快速色调。

公开(公告)号：US4975540A

公开(公告)日：1990-12-04

申请号：US300072

申请日：1989-01-19

Applicant: Reinhard Hahnle ,  Hartmut Springer

Inventor： Reinhard Hahnle ,  Hartmut Springer

IPC: C09B62/513 ,  D06P3/10 ,  D06P3/66

CPC classification number: C09B62/513

Abstract: Disazo compounds conforming to the general formula (1) below and suitable for use as fiber-reactive dyes for the dyeing of carboxamido-containing and/or hydroxy-containing materials such as wool and, in particular, cellulose fiber materials, in navy hues having good fastness properties ##STR1## in which M is a hydrogen atom or an alkali metal or alkaline earth metal,D.sup.1 is a phenyl radical which can be substituted by substituents from the group consisting of chlorine, bromine, sulfo, alkyl and alkoxy and additionally by a vinylsulfonyl or .beta.-sulfatoethylsulfonyl group or by a group of the general formula (3) ##STR2## where X is a vinyl or .beta.-sulfatoethyl group; D.sup.2 is a radical of the general formula (4) ##STR3## in which M and X have one of the abovementioned meanings and the amino group --NH-- is bound to the benzene ring in the para-position with respect to the sulfo group --SO.sub.3 M or in the paara-position with respect to the free bond.

Abstract translation: 符合下述通式（1）的双偶氮化合物适合用作染料含羧酰氨基和/或含羟基材料如羊毛，特别是纤维素纤维材料的纤维活性染料， （1）其中M为氢原子或碱金属或碱土金属，D1为可由氯，溴，磺基，烷基和烷氧基中的取代基取代的苯基 另外通过乙烯基磺酰基或β-磺酰基乙基磺酰基或通式（3）的基团，其中X是乙烯基或β-磺基乙基; D 2是通式（4）的基团，其中M和X具有上述含义之一，氨基-NH-与对位中的苯环相对于 磺基-SO 3 M或相对于游离键的paara位置。

公开(公告)号：US4952688A

公开(公告)日：1990-08-28

申请号：US233161

申请日：1988-08-17

Applicant: Hartmut Springer

Inventor： Hartmut Springer

IPC: C07D487/22 ,  C09B62/517 ,  D06P1/384

CPC classification number: C09B62/517

Abstract: Phthalocyanine compounds having fiber-reactive dye properties which dye hydroxyl- and/or carboxamido-containing material, in particular fiber material, such as cellulose fibers, wool and synthetic polyamide fibers, in fast and deep shades and which conform to the general formula (1) ##STR1## where Pc is the radical of copper- or nickel-phthalocyanine whose benzene nuclei can be substituted by chlorine or phenyl,R is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms which can be substituted by a hydroxy, sulfato, cyano or sulfo group,M is a hydrogen atom or one equivalent of a salt-forming metal, preferably a hydrogen atom or an alkali metal,Y is a vinyl group or preferably a .beta.-sulfatoethyl group,R.sup.1 is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms which can be substituted, andR.sup.2 has one of the meanings of R.sup.1 and is identical to R.sup.1 or different from R.sup.1 or --NR.sup.1 R.sup.2 together form a group of the formula (2) ##STR2## where M has the abovementioned meaning,m is the number 1, 2, 3 or 4,a is an integral or fractional number from 1 to 4,b is an integral or fractional number from zero to 3, andc is an integral or fractional number form zero to 3, with the proviso that the sum of (a+b+c) is an integral or fractional number from 2 to 4, the sulfonamide and sulfo groups are each bonded to the carbocyclic aromatic rings of the phthalocyanine in the 3- and/or 4-position.

Abstract translation: 具有纤维反应性染料性质的酞菁化合物，其染色含有羟基和/或羧酰氨基的材料，特别是纤维素纤维，如纤维素纤维，羊毛和合成聚酰胺纤维，具有快速和深色调，并符合通式（1 （1）其中Pc是铜或镍 - 酞菁的基团，其苯原子可以被氯或苯基取代，R是氢原子或可被1-4个碳原子取代的1-4个碳原子的烷基 羟基，硫酸根，氰基或磺基，M是氢原子或一当量的成盐金属，优选氢原子或碱金属，Y是乙烯基或优选β-磺基乙基，R1是 氢原子或可被取代的具有1至4个碳原子的烷基，并且R 2具有R 1的含义之一并且与R 1相同或不同于R 1或-NR 1 R 2一起形成式（2）的基团 IMAGE>（2）其中M具有上述含义，mi 数字1，2，3或4，a是从1到4的整数或小数，b是零到3的整数或小数，c是0到3的整数或分数， 条件是（a + b + c）的总和为2至4的整数或分数，磺酰胺和磺基各自键合在3-和/或4-位的酞菁的碳环芳环上。

公开(公告)号：US4898933A

公开(公告)日：1990-02-06

申请号：US348276

申请日：1989-05-05

Applicant: Ludwig Schlafer ,  Hartmut Springer ,  Reinhard Hahnle

Inventor： Ludwig Schlafer ,  Hartmut Springer ,  Reinhard Hahnle

IPC: C09B62/44

CPC classification number: C09B62/4415

Abstract: Water-soluble azo compounds having useful fiber-reactive dye properties conforming to the general formula ##STR1## in which: A is phenylene which may be substituted by lower alkoxy, lower alkyl, chlorine, sulfo and carboxy, or is a radical of the formula ##STR2## in which W is a direct bond or a radical of the formula --CH.dbd.CH-- or --NH--CO--NH-- and R* denotes hydrogen, nitro, sulfo, carboxy, methyl, ethyl, methoxy or ethoxy;n is the number zero or 1;B is a radical of the formula ##STR3## where R is equal to carboxy or carbamoyl; M is hydrogen or an alkali metal;K is a radical of the formula ##STR4## in which D is phenylene which may be substituted by chlorine, bromine, lower alkyl, lower alkoxy, carboxy and sulfo, or unsubstituted or sulfo substituted naphthylene;R.sup.1 is hydrogen, chlorine, lower alkyl or lower alkoxy;R.sup.2 is hydrogen or lower alkyl;G is carboxy, methyl or lower carbalkoxy;Y is vinyl, .beta.-sulfatoethyl or .beta.-chloroethyl;m is the number zero or 1;Z is .alpha.- or .beta.-bromacryloyl or .beta.-chloropropionyl, .beta.-chloroethylsulfonylbenzoyl or (.beta.-chloroethylsulfonylmethyl)-benzoyl or a radical of the formula ##STR5## where D and Y have the abovementioned meaning and Hal is equal to chlorine or fluorine.The compounds (1) produce fast dyeings on carboxamido- and/or hydroxy-containing materials, in particular cellulose fibers. On cellulose, fast dyeings are also obtained in a weakly acid to neutral medium, for example together with disperse dyes for dyeing a polyester fiber portion.

Abstract translation: 具有符合通式的有用的纤维反应性染料性质的水溶性偶氮化合物，其中：A是可被低级烷氧基，低级烷基，氯，磺基和羧基取代的亚苯基，或者是式 其中W是直接键或式-CH = CH-或-NH-CO-NH-的基团，R *表示氢，硝基，磺基，羧基，甲基，乙基，甲氧基或乙氧基; n是数字0或1; B是下式的基团：其中R等于羧基或氨基甲酰基; M是氢或碱金属; K是下式的基团：其中D是可被氯，溴，低级烷基，低级烷氧基，羧基和磺基取代的亚苯基，或未被取代的 或磺基取代的亚萘基; R1是氢，氯，低级烷基或低级烷氧基; R2是氢或低级烷基; G是羧基，甲基或低级烷氧羰基; Y是乙烯基，β-磺基乙基或β-氯乙基; m是数字0或1; Z是α-或β-溴丙烯酰或β-氯丙酰基，β-氯乙基磺酰基苯甲酰基或（β-氯乙基磺酰基甲基） - 苯甲酰基或式（IMAGE）的基团，其中D和Y具有上述含义，Hal等于氯或氟。 化合物（1）在甲酰氨基和/或羟基的材料，特别是纤维素纤维上产生快速染色。 在纤维素上，也可以在弱酸性至中性介质中获得快速染色，例如与用于染色聚酯纤维部分的分散染料一起使用。

公开(公告)号：US4740592A

公开(公告)日：1988-04-26

申请号：US913485

申请日：1986-09-30

Applicant: Hartmut Springer ,  Michael Kunze ,  Marcos Segal ,  Werner H. Russ

Inventor： Hartmut Springer ,  Michael Kunze ,  Marcos Segal ,  Werner H. Russ

IPC: C07D251/52 ,  C07D251/70 ,  C09B62/51 ,  D06P1/384 ,  D06P3/10 ,  D06P3/66 ,  C09B62/507

CPC classification number: C09B62/51

Abstract: Water soluble azo compounds having fiber-reactive dye properties conforming to the formula ##STR1## in which D denotes a benzene or naphthalene ring;R.sup.1 denotes hydrogen, alkyl, alkoxy, sulfo or carboxy;R.sup.2 denotes hydrogen, alkyl, alkoxy, sulfo, carboxy, substituted or unsubstituted aryl, hydroxy, nitro or halogen;R denotes hydrogen or substituted or unsubstituted alkyl;A denotes hydroxy, substituted or unsubstituted alkoxy or aryloxy, thio, substituted or unsubstituted alkylthioether or arylthioether or an optionally monosubstituted or disubstituted amino group having substituents from the aliphatic and aromatic and the acylamide series;B hydroxy, optionally substituted alkoxy or aryloxy, thio, optionally substituted alkylthioether or arylthioether or an optionally monosubstituted or disubstituted amino group having substituents from the aliphatic and aromatic and the acylamide series;M denotes hydrogen, alkali or alkaline earth;m denotes the number 1 or 2;n denotes the number 0 or 1;p denotes the number 0, 1 or 2;Y denotes .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl, vinyl or .beta.-sulfatoethyl; the group --SO.sub.2 --Y is bonded to A or D or to both; or in which:A is chlorine or bromine,B is an optionally monosubstituted or disubstituted amino group having substituents from the aliphatic and aromatic and the acylamide series,m denotes the number 1 and the group --SO.sub.2 Y is bonded to D andD, R.sup.1, R.sup.2, R, M, n, p and Y have the above meanings.The new azo compounds dye fiber materials, such as wool and in particular cellulose, in strong and fast shades.

Abstract translation: 具有符合式（1）＆lt; IMAGE＆gt;的式（1）的具有纤维反应性染料性质的水溶性偶氮化合物，其中D表示苯或萘环; R1表示氢，烷基，烷氧基，磺基或羧基; R 2表示氢，烷基，烷氧基，磺基，羧基，取代或未取代的芳基，羟基，硝基或卤素; R表示氢或取代或未取代的烷基; A表示羟基，取代或未取代的烷氧基或芳氧基，硫代，取代或未取代的烷基硫醚或芳基硫醚或任选具有脂族和芳族和酰基酰胺系列取代基的单取代或二取代的氨基; B羟基，任选取代的烷氧基或芳氧基，硫代，任选取代的烷基硫醚或芳硫醚或具有脂族和芳族和酰基酰胺系列取代基的任选单取代或二取代的氨基; M表示氢，碱或碱土; m表示数字1或2; n表示数字0或1; p表示数字0,1或2; Y表示β-硫代硫代乙基，β-磷酰乙基，β-氯乙基，乙烯基或β-磺基乙基; 基团-SO 2 -Y键合到A或D或两者; 或其中：A为氯或溴，B为任选具有脂族和芳族和酰基酰胺系列取代基的单取代或二取代的氨基，m表示数1，基团-SO 2 Y与D键合，D， R2，R，M，n，p和Y具有上述含义。 新的偶氮化合物染料纤维材料，如羊毛，特别是纤维素，具有强烈和快速的色调。

公开(公告)号：US4394129A

公开(公告)日：1983-07-19

申请号：US296469

申请日：1981-08-26

Applicant: Hartmut Springer

Inventor： Hartmut Springer

IPC: C09B69/00 ,  C09B1/32 ,  C09B1/34 ,  C09B5/14 ,  C09B19/02 ,  C09B29/00 ,  C09B33/153 ,  C09B35/215 ,  C09B47/26 ,  C09B57/12 ,  D06M13/345 ,  D06M13/402 ,  D06M13/438 ,  D06P1/00 ,  D06P1/18 ,  C07C125/08 ,  D06P1/16

CPC classification number: C09B5/14 ,  C09B1/325 ,  C09B1/343 ,  C09B19/02 ,  C09B29/00 ,  C09B33/153 ,  C09B35/215 ,  C09B47/26 ,  C09B57/12 ,  D06M13/345 ,  D06M13/402 ,  D06M13/438 ,  D06P1/0048 ,  Y10S8/917 ,  Y10S8/918 ,  Y10S8/924

Abstract: Fibrous materials of any kind is finished with an organic compound having fiber-finishing properties and containing one or several groups of the formula ##STR1## in which X is sulfonyl or carbonyl and A represents hydrogen or one equivalent of a mono-, bi- or trivalent metal or an ammonium group, is applied onto the fibrous material in the form of an aqueous or organo-aqueous solution or dispersion, and the fibrous material thus treated is then subjected, if necessary, to a heat treatment for the fixation of this organic compound onto the fibrous material. Organic fiber-finishing compounds containing the above-mentioned group may be for example dyestuffs, optical brighteners or compounds increasing the crease resistance.

Abstract translation: 任何类型的纤维材料用具有纤维整理性质的有机化合物完成，并含有一个或几个式（IMAGE）的基团，其中X是磺酰基或羰基，A代表氢或一个当量的单，双或 三价金属或铵基以水溶液或有机水溶液或分散体的形式施加到纤维材料上，然后如果需要，将如此处理的纤维材料进行热处理以固定该有机物 复合到纤维材料上。 含有上述基团的有机纤维整理化合物可以是例如增加抗折皱性的染料，荧光增白剂或化合物。

公开(公告)号：US5128455A

公开(公告)日：1992-07-07

申请号：US454373

申请日：1989-12-21

Applicant: Hartmut Springer ,  Patrick Scheidhauer ,  Karl-Michael Reichert ,  Guther Schwaiger ,  Kurt Hussong

Inventor： Hartmut Springer ,  Patrick Scheidhauer ,  Karl-Michael Reichert ,  Guther Schwaiger ,  Kurt Hussong

IPC: C09B62/44 ,  C09B62/503 ,  D06P3/10 ,  D06P3/66

CPC classification number: C09B62/4403 ,  C09B62/503

Abstract: Water-soluble fiber-reactive dyes which contain one or more groups of the general formula (1) ##STR1## where R.sup..alpha. and R.sup..beta. are each hydrogen or lower alkyl,R is hydrogen or sulfoY is vinyl or ethyl which is substituted in the .beta.-position by a substituent which is eliminatable under alkaline conditions,W is hydroxy, N-morpholino, N-piperidinyl, N-pyrrolidinyl or a group of the general formula (2) ##STR2## where G is hydrogen or alkyl of 1 to 6 carbon atoms andQ is a group of the general formula (2a), (2b), (2c) or (2d) ##STR3##--(CH.sub.2).sub.t --R.sup.a (2b)--(CH.sub.2).sub.t --O--(CH.sub.2).sub.w --R.sup.a (2c)--(CH.sub.2).sub.t --R.sup.2 (2d)whereR.sup.a is a group of the general formula --SO.sub.2 --Y, where Y is as defined above, or sulfo,R.sup.b is hydrogen, alkoxy of 1 to 4 carbon atoms, sulfo, hydroxy, carboxy or chlorine,R.sup.c is hydrogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,t is from 1 to 6 andw is from 1 to 6, orW is a radical of the general formula (2e)--A--(CH.sub.2).sub.r --R.sup.a (2e)whereR.sup.a is as defined above,r is zero, 1 or 2, andA is a radical of the general formula ##STR4##

Abstract translation: 含有一个或多个通式（1）的基团的水溶性纤维反应性染料其中Rα和Rβ各自为氢或低级烷基，R为氢或磺基Y为乙烯基或乙基， 通过在碱性条件下可消除的取代基在β-位置取代，W是羟基，N-吗啉代，N-哌啶基，N-吡咯烷基或通式（2）的基团其中G （2a），（2b），（2c）或（2d）（2a） - （CH2）t-Ra（2b）的基团， - （CH2）tO-（CH2）w-Ra（2c） - （CH2）t-R2（2d）其中Ra是通式-SO2-Y的基团，其中Y定义如上，或磺基，Rb 是氢，1至4个碳原子的烷氧基，磺基，羟基，羧基或氯，Rc是氢，1至4个碳原子的烷基或1至4个碳原子的烷氧基，t是1至6，w是1 至6，或W为通式（2e）-A-（CH2）r-Ra（2e）的基团，其中Ra如上定义，r 是0，1或2，A是通式为“IMAGE”的基团

公开(公告)号：US5093483A

公开(公告)日：1992-03-03

申请号：US528024

申请日：1990-06-26

Applicant: Hartmut Springer ,  Kurt Hussong

Inventor： Hartmut Springer ,  Kurt Hussong

IPC: D06P1/384 ,  C09B62/51

CPC classification number: C09B62/51

Abstract: Water-soluble monoazo compounds having fiber-reactive dyestuff properties which correspond to the general formula ##STR1## in which M is a hydrogen atom or an alkali metal,D is a group of the general formula (2a), (2b) or (2c) ##STR2## in which R.sup.1 denotes hydrogen, cyano, lower alkyl which is optionally substituted by sulfo, carboxy or sulfato, hydroxy, alkoxy which is optionally subhstituted by sulfo, carboxy, or sulfato, sulfo, carboxy, halogen or denotes a group of the formula (3) ##STR3## in which alk is an alkylene having 2 to 4 carbon atoms,R is sulfo, carboxy, sulfato or phosphato andR.sup.1 is hydrogen, methyl or ethyl,R.sup.2 denotes hydrogen, lower alkoxy, lower alkyl or sulfo,Y is the vinyl group or stands for an ethyl group which contains a subhstituent in the .beta.-position which can be eliminated by alkali,k is the number 1 or 2 andn denotes the number zero or 1.

Abstract translation: 具有纤维反应性染料性质的水溶性单偶氮化合物对应于通式（1）其中M为氢原子或碱金属，D为通式（2a），（2b）的基团， （2c）其中R1表示氢，氰基，任选被磺基，羧基或硫酸根取代的低级烷基，（羟基），任选被取代的烷氧基（2c） 磺基，磺基，羧基，卤素或表示式（3）的基团，其中alk是具有2至4个碳原子的亚烷基，R是磺基，羧基，硫酸酯基或 磷酸酯和R 1是氢，甲基或乙基，R 2表示氢，低级烷氧基，低级烷基或磺基，Y是乙烯基，或代表在β-位上含有取代基的乙基，可以被碱，k 是数字1或2，n表示数字0或1。

公开(公告)号：US5043435A

公开(公告)日：1991-08-27

申请号：US484517

申请日：1990-02-23

Applicant: Hartmut Springer ,  Kurt Hussong

Inventor： Hartmut Springer ,  Kurt Hussong

IPC: C09B62/51

CPC classification number: C09B62/51

Abstract: Diazonium compounds are disclosed which correspond to the formula ##STR1## in which Y' is vinyl, .beta.-hydroxyethyl of an ethyl group having a substituent in the .beta.-position which is eliminated by means of alkali, R is hydrogen, hydroxy, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, carboxy or halogen, n is the number 0, 1 or 2, M is hydrogen or an alkali metal, and An is an anion, and wherein the diazonium group is bound in the meta- or para-position to the nitrogen of the benzotriazole radical.Also disclosed is a process for the preparation of the diazonium compounds. The compounds are useful as diazo components for the preparation of azo compounds by a coupling reaction.