公开(公告)号：US5350838A

公开(公告)日：1994-09-27

申请号：US14905

申请日：1993-02-08

Applicant: Mark A. Helle ,  Walter Helmling

Inventor： Mark A. Helle ,  Walter Helmling

IPC: C07D251/50 ,  C07D251/54 ,  C07D251/70 ,  C09B41/00 ,  C09B62/44 ,  C09B62/51 ,  C09B67/24

CPC classification number: C09B62/4413 ,  C07D251/50 ,  C07D251/54 ,  C09B41/006

Abstract: A process for preparing monoazo dyes by coupling a aromatic diazonium salt with an amino-4-hydroxy-naphthalene sulfonic acid derivative at a temperature of 40.degree.-85.degree. C. The process of the invention provides a isomerically purer dye.

Abstract translation: 通过在40-85℃的温度下将芳族重氮盐与氨基-4-羟基 - 萘磺酸衍生物偶合来制备单偶氮染料的方法。本发明的方法提供异构纯的染料。

公开(公告)号：US4786728A

公开(公告)日：1988-11-22

申请号：US909010

申请日：1986-09-18

Applicant: Gunther Schwaiger ,  Hartmut Springer ,  Walter Helmling

Inventor： Gunther Schwaiger ,  Hartmut Springer ,  Walter Helmling

IPC: C09B19/00 ,  C07C67/00 ,  C07C313/00 ,  C07C317/14 ,  C07C317/22 ,  C07C317/34 ,  C07C317/36 ,  C07C317/46 ,  C07C317/48 ,  C07C323/65 ,  C07D498/04 ,  C09B62/503 ,  D06P1/384 ,  D06P3/10 ,  D06P3/66 ,  C09B19/02

CPC classification number: C09B62/5033

Abstract: Triphendioxazine compounds with properties of fiber-reactive dyestuffs corresponding to the general formula ##STR1## in which T is an optionally substituted alkyl group with 1 to 6 carbon atoms, excluding a radical of the group Y defined below, it also being possible for the alkyl group to be interrupted by hetero atoms, or is an optionally substituted aryl group,B is an oxygen or sulfur atom or an amino group,W is a divalent, optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic-carbocyclic radical or a benzotriazole radical combined with one of these radicals, it being possible for the aliphatic radicals to be interrupted by hetero groups and/or for aliphatic and aryl radicals to be bonded to one another by a hetero group,R is hydrogen, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 5 carbon atoms, halogen, carboxy or sulfo,X.sup.1 is hydrogen, halogen, cycloalkyl, aralkyloxy, alkoxy, aryloxy, alkyl, aryl, aralkyl, cyano, carboxy, carbalkoxy, arylamino, carbamoyl, which is optionally substituted, alkanoylamino or aroylamino,X.sup.2 can have the meaning of X.sup.1,n represents the number 1 or 2,Y is the vinyl group or an ethyl group which is substituted in the .beta.-position by a substituent which can be eliminated with an alkaliand the molecule (1) contains at least one sulfo or sulfato group.

Abstract translation: 对应于通式（1）的纤维活性染料性质的三苯并二恶嗪化合物，其中T是具有1-6个碳原子的任选取代的烷基，不包括下面定义的基团Y的基团，也是可能的 由于烷基被杂原子中断，或是任选取代的芳基，B是氧或硫原子或氨基，W是二价，任选取代的脂族，脂环族，芳脂族或芳族 - 碳环基或 苯并三唑基与这些基团中的一个结合，脂族基团可以被杂基和/或通过杂基团彼此键合的脂族和芳基自由中断，R是氢，具有1至6个的烷基 碳原子，具有1至5个碳原子的烷氧基，卤素，羧基或磺基，X 1是氢，卤素，环烷基，芳烷氧基，烷氧基，芳氧基，烷基，芳基，芳烷基，氰基，羧基，烷氧基，芳基氨基， 乙酰基，其可以被取代，烷酰基氨基或芳酰基氨基，X 2可以具有X 1的含义，n表示数字1或2，Y是乙烯基或在β-位置被取代基取代的乙基，该取代基可以是 用碱去除，分子（1）含有至少一个磺基或硫酸根基团。

公开(公告)号：US4782150A

公开(公告)日：1988-11-01

申请号：US84427

申请日：1987-08-11

Applicant: Hartmut Springer ,  Walter Helmling ,  Gunther Schwaiger

Inventor： Hartmut Springer ,  Walter Helmling ,  Gunther Schwaiger

IPC: C09B19/00 ,  C07C67/00 ,  C07C313/00 ,  C07C317/22 ,  C07C317/36 ,  C07C323/25 ,  C07D498/04 ,  C09B62/503 ,  C09B19/02

CPC classification number: C09B62/5033

Abstract: Water-soluble triphendioxazine compounds which have valuable fiber-reactive dyestuff properties and correspond to the general formula (1) and dye materials, in particular cellulose fiber materials, containing carboxamide and/or hydroxy groups in fast shades. ##STR1## in which: B is a group --O--, --S--, --NH-- or --N(R')-- in which R' is alkyl having 1 to 6 carbon atoms;R* is hydrogen or optionally substituted lower alkyl or optionally substituted aryl;W and W.sup.1 independently of one another are each a divalent aliphatic radical or a cycloaliphatic radical which is optionally substituted by lower alkyl or an aliphatic-cycloaliphatic radical which is optionally substituted by lower alkyl, it being possible for the aliphatic radicals to be interrupted by one or more groups --O--, --S--, --SO.sub.2 --, --CO--, 1,4-piperidino, --NH-- and --N(R.sup.o)-- in which R.sup.o has the meaning of R' or is lower alkanoyl;the groupings --B--W.sup.1 --N(R*)-- and --N(R*)--W--B 13 independently of one another each represent the divalent radical of a five-membered or six-membered, saturated heterocyclic structure containing two N atoms, or the groupings --B--W.sup.1 -- and --W--B-- independently of one another each represent the divalent radical of a five-membered or six-membered, saturated heterocyclic structure which contains two N atoms and which is attached by means of one of the two N atoms, via a C.sub.2 -C.sub.4 -alkylene, to the groupings --N(R*)--A or A--N(R*)--, respectively;is benzoyl, naphthoyl, N-phenylcarbamoyl or N-naphthylcarbamoyl in which the phenyl and naphthyl radicals can be substituted, at least one of these being a group which imparts solubility in water;X.sup.1 and X.sup.2 independently of one another are each hydrogen, halogen, lower alkyl, lower alkoxy or optionally substituted aryl;Y is vinyl or a .beta.-substituted ethyl;and the compounds necessarily contain at least two sulfo groups.

Abstract translation: 具有有价值的纤维反应性染料性能并对应于通式（1）的染料和特别是纤维素纤维材料的水溶性三苯并二恶嗪化合物，其特征在于纤维素纤维材料，其具有快速阴影的羧酰胺和/或羟基。 （1）其中：B是-O - ， - S-，-NH-或-N（R'） - 基团，其中R'是具有1至6个碳原子的烷基; R *是氢或任选取代的低级烷基或任选取代的芳基; W和W1彼此独立地是二价脂族基团或脂环族基团，其任选被低级烷基或任选被低级烷基取代的脂族 - 脂环族基团取代，脂族基团可能被一个 或更多的基团-O - ， - S - ， - SO 2 - ， - CO-，1,4-哌啶子基，-NH-和-N（Ro） - ，其中Ro具有R'或低级烷酰基的含义; B-W1-N（R *） - 和-N（R *）-WB 13彼此独立地分别代表含有两个N原子的五元或六元饱和杂环结构的二价基团， 或基团-B-W1-和-WB-彼此独立地各自表示含有两个N原子的五元或六元饱和杂环结构的二价基团，并且其通过二者之一连接 N原子通过C 2 -C 4亚烷基分别连接到-N（R *）-A或AN（R *） - 基团上; 是苯甲酰基，萘甲酰基，N-苯基氨基甲酰基或N-萘基氨基甲酰基，其中苯基和萘基可以被取代，这些中的至少一个是赋予在水中溶解度的基团; X1和X2各自独立地为氢，卤素，低级烷基，低级烷氧基或任选取代的芳基; Y是乙烯基或β-取代的乙基; 并且化合物必然含有至少两个磺基。

公开(公告)号：US4816574A

公开(公告)日：1989-03-28

申请号：US76927

申请日：1987-07-23

Applicant: Gunther Schwaiger ,  Hartmut Springer ,  Walter Helmling

Inventor： Gunther Schwaiger ,  Hartmut Springer ,  Walter Helmling

IPC: C07D249/18 ,  C07D498/04 ,  C09B19/02 ,  C09B62/503 ,  D06P1/38 ,  C09B19/00

CPC classification number: C07D498/04 ,  C09B62/5033

Abstract: Water-soluble triphendioxazine compounds which have fiber-reactive properties as dyestuffs, which afford deep and fast dyeings on fiber materials, such as wool and, in particular, cellulose, and which correspond to the formula (1) ##STR1## in which: n is the number 0 or 1;Y is the vinyl group or an ethyl group containing, in .beta.-position, a substituent which can be eliminated by means of an alkali;Q.sup.1 and Q.sup.2 both represent a benzotriazole radical which can also be additionally substituted in the benzene nucleus by alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogen, carboxy or sulfo;B is --O--, --S--, --NH--or --N(R')--wherein R' is optionally substituted alkyl having 1 to 6 carbon atoms;W.sup.1 and W.sup.2 both represent a divalent, optionally substituted aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, araliphatic or aromatic-carbocyclic radical, it being possible for the aliphatic radicals to be interrupted by hetero groups --O--, --S--, --SO.sub.2 --, --CO--, 1,4-piperidino, --NH--and/or --N(R.sup.o)--in which R.sup.o is optionally substituted alkyl having 1 to 6 carbon atoms or alkanoyl having 2 to 5 carbon atoms, and/or for aliphatic and aryl radicals to be attached to one another through such a hetero group;R is hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, halogen, carboxyl or sulfo;E is hydrogen, sulfo, carboxyl, a group --SO.sub.2 --Y as defined above or an optionally substituted sulfonamide group; andX.sup.1 and X.sup.2 are both hydrogen, cycloalkyl, alkoxy, aryloxy, aryl or another substituent;and at least one carboxy, sulfo or sulfato group is present in the molecule (1),and pre-products of those triphendioxazine compounds, of the general formula ##STR2## in which K is an amino or nitro group, Y' is .beta.-hydroxyethyl or defined as for Y, W has one of the meanings of W.sup.1, and E' is hydrogen, sulfo, carboxy or a group of the formula --SO.sub.2 --Y' defined above, or an optionally substituted sulfonamide group, and R, B and R* have the above meanings.

公开(公告)号：US5532362A

公开(公告)日：1996-07-02

申请号：US450965

申请日：1995-05-25

Applicant: Walter Helmling ,  David Brunetti ,  Uwe Reiher

Inventor： Walter Helmling ,  David Brunetti ,  Uwe Reiher

IPC: C07D498/04 ,  C09B62/503

CPC classification number: C07D498/04 ,  C09B62/5033

Abstract: The present invention is directed to a dioxazine dye which provides brilliant reddish blue dyeings possessing superior fastness properties and high tinctorial strength.

Abstract translation: 本发明涉及一种二恶嗪染料，其提供具有优异坚牢性和高着色强度的亮蓝色染色。

公开(公告)号：US4851527A

公开(公告)日：1989-07-25

申请号：US901285

申请日：1986-08-27

Applicant: Hartmut Springer ,  Gunther Schwaiger ,  Walter Helmling

Inventor： Hartmut Springer ,  Gunther Schwaiger ,  Walter Helmling

IPC: C07D265/38 ,  C09B62/503 ,  D06P3/10 ,  D06P3/66

CPC classification number: C09B62/5033

Abstract: Water-soluble triphendioxazine compounds of the formula ##STR1## having at least one sulfato or sulfo group, in which R is a hydrogen atom, a water-solubilizing group, an alkyl group having 1 to 6 carbon atoms which is substituted by an acidic group, or an optionally substituted sulfonamide group,B is an oxygen or sulfur atom or a group of the formula --NH--or --N(R')--, where R' equals optionally substituted alkyl, cycloalkyl which is optionally substituted by certain substituents, or optionally substituted phenyl, or naphthyl which is optionally substituted by sulfo and/or a --SO.sub.2 --Y' group,B.sup.1 has one of the meanings stated for B and is identical to B or different from B,W is a bivalent aliphatic, araliphatic or aromatic radical which may be interrupted by 1 or 2 hetero groups from the series comprising groups of the formulae --O--, --NH--and --N(R')--, where R' has the above meaning,W.sup.1 has one of the meanings stated for W and is identical to W or different from W,T is a hydrogen atom or sulfo, sulfato, phosphato or carboxy,T.sup.1 has one of the meanings stated for T and is identical to T or different from T and T.sup.1 is necessarily a water-solubilizing group when R denotes hydrogen,R.sup.3 R.sup.4, identical or different, are each hydrogen, alkyl, alkoxy, halogen, carboxy or sulfo,X.sup.1 is hydrogen, halogen, cycloalkyl, arylkyloxy, alkoxy, aryloxy, alkyl, aryl, aralkyl, cyano, carboxyl, carbalkoxy, N-alkyl-substituted carbamoyl or N-aryl-substituted carbamoyl, alkanoylamino or optionally substituted aroylamino,X.sup.2 has one of the meanings stated for X.sup.1 and is identical to X.sup.1 or different from X.sup.1,Y is vinyl or ethyl which is substituted in the .beta. position by a substituent which can be eliminated by means of an alkali,Y' has one of the meanings stated for Y and is identical to Y or different from Y.These new compounds have fiber-reactive dyestuff properties and are particularly suitable for dyeing cellulose fiber materials so that they are fast.

公开(公告)号：US4785099A

公开(公告)日：1988-11-15

申请号：US943643

申请日：1986-12-17

Applicant: Hartmut Springer ,  Gunther Schwaiger ,  Walter Helmling

Inventor： Hartmut Springer ,  Gunther Schwaiger ,  Walter Helmling

IPC: C09B62/04 ,  C09B62/44 ,  C09B62/443 ,  C09B62/503 ,  D06P1/38 ,  D06P3/66 ,  C07D265/38 ,  C09B19/02

CPC classification number: C09B62/046 ,  C09B62/4405 ,  C09B62/443

Abstract: Water-soluble triphendioxazine compounds having fiber-reactive dye properties and the general formula (1) ##STR1## in which the meanings are: T is a substituted or unsubstituted alkyl of 1 to 6 carbon atoms, except an ethyl which is substituted in the .beta.-position by an alkalinically eliminatable substituent, which alkyl can be interrupted by --O--, --S--, --NH-- and --N(R')-- where R' is equal to substituted or unsubstituted alkyl of 1 to 6 carbon atoms, or is substituted or unsubstituted aryl,B is --O--, --S--, --NH-- or --N(R")-- where R" is equal to substituted or unsubstituted alkyl,W is a bridge member orW and B together form a direct bond,R is hydrogen or a substituent,R* is hydrogen or a substituent or R* and W, if W contains an amino group, or a portion of W form together with the nitrogen atoms the radical of a heterocycle,A is a non-heterocyclic fiber-reactive group or a 2-halogeno-s-triazin-6-yl radical which is substituted in the 4-position by halogen or a substituted or unsubstituted amino group which can also contain a fiber-reactive group, or by a heterocyclic radical or by a further such halogenotriazinyl radical bonded via an amino radical as bridge member,X.sup.1 and X.sup.2 are each hydrogen, halogen, cycloalkyl, aralkoxy, alkoxy, aryloxy, alkyl, aryl, aralkyl, cyano, carboxy, carbalkoxy, arylamino, carbamoyl and alkylmono- or -disubstituted carbamoyl or arylcarbamoyl, alkanoylamino or aroylamino, which aryl radicals can in each case be substituted;of the sulfo and sulfate groups the molecule mandatorily contains at least one of these groups,furthermore precursors of the formulae ##STR2## with B* equal to --NH-- or --N(R")-- and R, R*, W and T of the abovementioned meanings.The triphendioxazine compounds serve for dyeing chiefly wool and synthetic polyamide fibers and in particular cellulose fibers by means of application and fixing methods which are customary for fiber-reactive dyes.

公开(公告)号：US5539109A

公开(公告)日：1996-07-23

申请号：US481420

申请日：1995-07-11

Applicant: Walter Helmling ,  Uwe Reiher

Inventor： Walter Helmling ,  Uwe Reiher

IPC: C07D498/04 ,  C09B62/04 ,  C09B62/44 ,  C09B62/503

CPC classification number: C07D498/04 ,  C09B62/046 ,  C09B62/4405

Abstract: The invention is that of a new triphenodioxazine dye of the formula: ##STR1## wherein: ##STR2## K is independently selected from SO.sub.3 H and COOH; W=a substituted or unsubstituted arylene, alkylene or arylene-alkylene group;Y.sup.1 =Vinyl, .beta.-Sulfatoethyl, .beta.-Thiosulfatoethyl, .beta.-Halogenethyl-group, .beta.-Phosphatoethyl, andX=H.R, R.sub.1 and R.sub.2 are independently selected from hydrogen and substituted or unsubstituted alkyl.T is independently selected from hydrogen, Cl, Br, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkoxy, phenyl or phenoxy; andn is selected from 0, 1 or 2.

Abstract translation: PCT No.PCT / US94 / 03233 Sec。 371日期：1995年7月11日 102（e）日期1995年7月11日PCT 1994年3月24日PCT公布。 出版物WO94 / 21646 日期1994年9月29日本发明是下式的新型三苯二恶嗪染料：其中：K独立地选自SO 3 H和COOH; W =取代或未取代的亚芳基，亚烷基或亚芳基 - 亚烷基; Y1 =乙烯基，β-亚硫酰乙基，β-硫代硫代乙基，β-氢化乙基，β-磷酰乙基，X = H。 R，R 1和R 2独立地选自氢和取代或未取代的烷基。 T独立地选自氢，Cl，Br，C 1至C 6烷基，C 1至C 6烷氧基，苯基或苯氧基; 并且n选自0,1或2。

公开(公告)号：US5003053A

公开(公告)日：1991-03-26

申请号：US497734

申请日：1990-03-19

Applicant: Hartmut Springer ,  Walter Helmling ,  Ludwig Schlafer ,  Werner H. Russ

Inventor： Hartmut Springer ,  Walter Helmling ,  Ludwig Schlafer ,  Werner H. Russ

IPC: C09B62/44

CPC classification number: C09B62/4413

Abstract: Water-soluble monoazo compounds of the general formula (1) which dye in fast, mainly red shades materials which contain carboxamide and/or hydroxy groups, preferably in the form of fibers, in particular cellulose fiber materials. ##STR1## in which: Y is .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl, vinyl or .beta.-sulfatoethyl,M is hydrogen, an alkali metal or an alkaline-earth metal,D is naphthyl which is substituted by sulfo and/or a group of the formula Y--SO.sub.2 --,or is one of the radicals ##STR2## in which M and Y have one of the above meanings, m is the number zero or 1, R.sup.1 is hydrogen, lower alkyl, lower alkoxy or carboxy, and R.sup.2 is hydrogen, lower alkyl, lower alkoxy, sulfo, carboxy, optionally substituted aryl, hydroxy, nitro or halogen,n is the number zero or 1,R is hydrogen or optionally substituted lower alkyl,R* is hydrogen or optionally substituted lower alkyl,X is fluorine or chlorine,B is a group of the formula ##STR3## in which R.sup.3 is hydrogen or optionally substituted lower alkyl or aryl, R.sup.4 is hydrogen, optionally substituted alkyl having 1 to 8 carbon atoms or cycloalkyl having 5 to 8 carbon atoms and optionally having 1 to 3 methyl groups and/or one amino, lower alkanoylamino or benzoylamino group as substituents, or is the phenyl radical which may be substituted by sulfo, carboxy, halogen, lower alkyl, lower alkoxy, nitro, a group of the formula --SO.sub.2 --Y' (where Y' has one of the meanings of Y or is .beta.-hydroxyethyl), lower alkylamino, lower dialkylamino, lower alkanoylamino and/or benzoylamino, or is naphthyl radical, which may be substituted by sulfo and/or a group of the formula --SO.sub.2 --Y', and R.sup.5 has one of the meanings specified for R.sup.4, or R.sup.4 and R.sup.5, together with the nitrogen atom and one, two or three lower alkylene radicals and, if appropriate, one or two further heteroatoms, form a lower heterocyclic radical.

公开(公告)号：US4898944A

公开(公告)日：1990-02-06

申请号：US263613

申请日：1988-10-27

Applicant: Gunther Schwaiger ,  Hartmut Springer ,  Walter Helmling

Inventor： Gunther Schwaiger ,  Hartmut Springer ,  Walter Helmling

IPC: C09B19/00 ,  C07C67/00 ,  C07C313/00 ,  C07C317/14 ,  C07C317/22 ,  C07C317/34 ,  C07C317/36 ,  C07C317/46 ,  C07C317/48 ,  C07C323/65 ,  C07D498/04 ,  C09B62/503 ,  D06P1/384 ,  D06P3/10 ,  D06P3/66 ,  C07C147/103 ,  C07C147/107 ,  C07C147/12

CPC classification number: C09B62/5033

Abstract: Precursors for the preparation of fiber-reactive triphendioxazine dyestuffs correspond to the general formulas: ##STR1## in which Y' is a vinyl, a beta-hydroxyethyl or an ethyl group which contains in the beta-position a substituent which can be eliminated by an alkali;T is an optionally substituted alkyl (e.g. substituted with hydroxy) with 1-6 carbon atoms, preferably 1 to 4 carbon atoms, excluding a radical of the group Y' defined above, it also being possible for the alkyl group to be interrupted by hetero groups, preferably 1 to 2 hetero groups, selected from groups of the formulae --O--, --S--, --NH-- and --N(R')--, where R' has the meaning given below, or T is an optionally substituted aryl group;B is an oxygen or sulfur atom or an amino group of the formula --NH-- or --N(R')--, in whichR' is an alkyl group with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, such as, in particular, the methyl or ethyl group, which can be substituted;W is a divalent, optionally substituted aliphatic, optionally alkyl-substituted (C.sub.5 -C.sub.10)-cycloaliphatic, optionally alkyl-substituted aliphatic-(C.sub.5 -C.sub.8)-cycloaliphatic, optionally substituted araliphatic or optionally substituted aromatic-carbocyclic radical or a benzotriazole radical combined with one of these radicals, it being possible for the aliphatic radicals in W to be interrupted by hetero groups, preferably 1 to 2 hetero groups, selected from the groups --O--, --S--, --SO.sub.2 --, --CO--, 1,4-piperidino, --NH-- and --N(R.sup.o)--, in which R.sup.o has one of the meanings of R' or is an alkanoyl group with 2 to 5 carbon atoms, such as an acetyl group, and/or it being possible for aliphatic and aryl radicals to be linked to one another by such a hetero group;R' is a hydrogen atom or alkyl with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, such as, in particular, methyl and ethyl of these, alkoxy with 1 to 5 carbon atoms, preferably 1 to 4 carbon atoms, such as, in particular, methoxy and ethoxy of these, halogen, such as fluorine or bromine or, in particular, chlorine, carboxy or sulfo;n is the number 1 to 2, but is preferably 1.