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    Method for printing cellulosic fiber materials without an additional fixing process step
    11.
    发明授权
    Method for printing cellulosic fiber materials without an additional fixing process step 失效
    无需附加固定工艺步骤的纤维素纤维材料的印刷方法

    公开(公告)号：US06623533B2

    公开(公告)日：2003-09-23

    申请号：US09899439

    申请日：2001-07-05

    Applicant: Athanassios Tzikas ,  Hans Reichert ,  Herbert Klier

    Inventor： Athanassios Tzikas ,  Hans Reichert ,  Herbert Klier

    IPC: D06P138

    CPC classification number: D06P1/382 ,  C09B62/4401 ,  D06P1/38 ,  D06P3/66 ,  D06P3/663 ,  Y10S8/918

    Abstract: A method of printing cellulosic fiber materials in which the fiber material is brought into contact with reactive dyes of formula: wherein A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore, R1, R2 and R3 are each independently of the others hydrogen or unsubstituted or substituted C1-C4alkyl, X1 and X2 are halogen, B is an organic bridging member, T is a reactive radical of formula: R4 is hydrogen, C1-C4alkyl unsubstituted or substituted by hydroxy, sulfo, sulfato, carboxy or by cyano, or a radical  wherein R5 is as defined hereinbelow, R5 is hydrogen, hydroxy, sulfo, sulfato, carboxy, cyano, halogen, C1-C4alkoxycarbonyl, C1-C4alkanoyloxy, carbamoyl or a group —SO2—Y, R6 is hydrogen or C1-C4alkyl, alk and alk1 are each independently of the other linear or branched C1-C6alkylene, arylene is an unsubstituted or sulfo-, carboxy-, hydroxy-, C1-C4alkyl-, C1-C4alkoxy- or halo-substituted phenylene or naphthylene radical, Y is vinyl or a radical —CH2—CH2—U and U is a leaving group, Y1 is a group —CH(Hal)-CH2(Hal) or —C(Hal)═CH2, wherein Hal is chlorine or bromine, W is a group —SO2—NR6—, —CONR6— or —NR6CO—, wherein R6 is as defined hereinabove, Q is a radical —O— or —NR6—, wherein R6 is as defined hereinabove, n is the number 0 or 1, and V1 and V2 are each independently of the other N, C—H, C—Cl or C—F, and the fixing of the printed fiber material is carried out without an additional fixing process step. The prints obtained are distinguished by brilliant colour shades and good allround properties.

    Abstract translation: 一种印刷纤维素纤维材料的方法，其中纤维材料与下式的活性染料接触：其中A是单偶氮，多偶氮，金属络合物偶氮，蒽醌，酞菁，甲an或二恶嗪发色团的基团，R1，R2和R3 各自独立地为氢或未取代的或取代的C 1 -C 4烷基，X 1和X 2为卤素，B为有机桥连构件，T为下式的反应性基团：R 4为氢，未被取代或被羟基取代的C 1 -C 4烷基，磺基 羧基，氰基，卤素，C 1 -C 4烷氧基羰基，C 1 -C 4烷酰氧基，氨基甲酰基或-SO 2 -Y基，其中R 5为氢，羟基，磺基， R 6是氢或C 1 -C 4烷基，alk和alk 1各自独立地为其它直链或支链C 1 -C 6亚烷基，亚芳基是未取代的或磺基，羧基，羟基，C 1 -C 4烷基 - ，C 1 -C 4烷氧基或卤素 - 取代的亚苯基或亚萘基，Y是乙烯基 基团-CH 2 -CH 2 -U和U是离去基团，Y 1是基团-CH（Hal）-CH 2（Hal）或-C（Hal）= CH 2，其中Hal是氯或溴，W是基团 - SO 2 -NR 6 - ， - CONR 6 - 或-NR 6 CO-，其中R 6如上所定义，Q为-O-或-NR 6 - 基团，其中R 6如上所定义，n为数字0或1，V 1和V 2 各自独立于另一个N，CH，C-Cl或CF，并且印刷的纤维材料的固定在没有额外的定影处理步骤的情况下进行。所获得的印刷品通过明亮的色调和良好的全面性质来区分。

    Reactive colorants, mixtures of reactive colorants and production and use thereof
    12.
    发明授权
    Reactive colorants, mixtures of reactive colorants and production and use thereof 失效
    反应性着色剂，反应性着色剂的混合物及其生产和用途

    公开(公告)号：US06537332B1

    公开(公告)日：2003-03-25

    申请号：US09744487

    申请日：2001-01-24

    Applicant: Athanassios Tzikas ,  Herbert Klier

    Inventor： Athanassios Tzikas ,  Herbert Klier

    IPC: C09B62475

    CPC classification number: C09B62/513 ,  C09B62/09 ,  C09B62/4415 ,  C09B62/453 ,  C09B62/475 ,  Y10S8/918 ,  Y10S8/924

    Abstract: Dyes of formula (1) wherein R1 and R2 are each independently of the other hydrogen or C1-C4alkyl, and D1 and D2 are each independently of the other a radical of formula (2)  wherein (R3)0-3 denotes from 0 to 3 identical or different substituents selected from the group halogen, C1-C4alkyl, C1-C4alkoxy, carboxy, nitro and sulfo, and X1 is a radical of formula (3a), (3b), (3c), (3d), (3e) or (3f) —SO2—Z  (3a), —NH—CO—(CH2)m—SO2—Z  (3b), —CONH—(CH2)n—SO2—Z  (3c), —NH—CO—CH(Hal)-CH2-Hal  (3d), —NH—CO—C(Hal)=CH2  (3e) or  wherein Y is halogen, T independently thereof has a meaning given for Y or is a non-fiber-reactive substituent or is a fiber-reactive radical of formula (4a), (4b), (4c), (4d) or (4e) —NH—(CH2)2-3—SO2—Z  (4a), —NH—(CH2)2-3—O—(CH2)2-3—SO2—Z  (4b),  wherein Z is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, Z′ is a group —CH(Hal)-CH2-Hal or —C(Hal)=CH2, m and n are each independently of the other the number 2, 3 or 4, and Hal is halogen, are suitable for dyeing a wide variety of fiber materials, especially cellulosic fiber materials, and yield dyeings having good allround properties.

    Abstract translation: 式（1）的染料其中R 1和R 2各自独立地为氢或C 1 -C 4烷基，D 1和D 2各自独立地为式（2）的基团，其中（R3）0-3表示0-3相同 或选自卤素，C 1 -C 4烷基，C 1 -C 4烷氧基，羧基，硝基和磺基的不同取代基，X 1为式（3a），（3b），（3c），（3d），（3e）或（ 3f）或其中Y是卤素，T独立地具有对Y给出的含义或者是非纤维反应性取代基，或者是式（4a），（4b），（4c），（4d）或 （4e）其中Z是乙烯基或基团-CH 2 -CH 2 -U，U是在碱性条件下可除去的基团，Z'是基团-CH（Hal）-CH 2 - Hal或-C（Hal）= CH 2，m和 n各自独立于另一个数字2,3或4，并且Hal是卤素，适用于染色各种纤维材料，特别是纤维素纤维材料，并且产生具有良好全面性能的染色。

    Reactive dyes, processes for their preparation and their use
    13.
    发明授权
    Reactive dyes, processes for their preparation and their use 失效
    活性染料，其制备方法及其用途

    公开(公告)号：US06323327B1

    公开(公告)日：2001-11-27

    申请号：US09704354

    申请日：2000-11-02

    Applicant: Athanassios Tzikas ,  Rolf Deitz ,  Herbert Klier

    Inventor： Athanassios Tzikas ,  Rolf Deitz ,  Herbert Klier

    IPC: C09B62513

    CPC classification number: C09B62/513 ,  C09B62/4415 ,  Y10S8/918

    Abstract: Reactive dyes of formula (1) wherein b is the number 1 or 2, A is the radical of formula (2) or (3) D1 is a radical off formula  or the radical of an azo dye when b is the number 1 or the radical of an aromatic tetraazo component when b is the number 2, D2 is the radical of a diazo component, of the benzene or naphthalene series, R1 and R2 are each independently of the other hydrogen or C1-C4alkyl, (R3)0-2 denotes from 0 to 2 substituents selected from the group C1-C4alkyl, C1-C4alkoxy, halogen and sulfo, X1 is fluorine or chlorine, Y is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, l is the number 2, 3, 4, 5 or 6, and m and n are each independently of the other the number 0 or 1, wherein when A is a radical of formula (3) and D1 is the radical of an azo dye, at least one of the radicals D1 and D2 contains a fibre-reactive radical of formula (2) with the proviso that A is a radical of formula (2) when D1 is the radical of an aromatic tetraazo component, and A is a radical of formula (3) when D1 is a radical of formula (4), are especially suitable for dyeing cotton and wool and yield dyeings having good all round properties.

    Abstract translation: 式（1）的活性染料其中b为数1或2，A为式（2）或（3）的基团，当b为数1或基团时，D1为自由基式或偶氮染料基团 的芳香族四偶氮组分，当b为数2时，D 2为苯或萘系的重氮组分的基团，R 1和R 2各自独立地为氢或C 1 -C 4烷基，（R 3）0-2表示 0-2个选自C1-C4烷基，C1-C4烷氧基，卤素和磺基的取代基，X1是氟或氯，Y是乙烯基或基团-CH2-CH2-U，U是在碱性条件下可除去的基团，l 是2,3,4,5或6号，m和n分别独立为数字0或1，其中当A是式（3）的基团且D1是偶氮染料的基团时，至少 自由基D1和D2之一含有式（2）的纤维反应性基团，条件是当D1是芳族四偶氮组分的基团时，A是式（2）的基团，A是 当D1是式（4）的基团时，式（3）的基团特别适用于染色棉和羊毛并产生具有良好全面性能的染色。

    Fibre-reactive azo dyes, their preparation and their use
    15.
    发明授权
    Fibre-reactive azo dyes, their preparation and their use 有权
    纤维反应偶氮染料，其制备及其用途

    公开(公告)号：US08562694B2

    公开(公告)日：2013-10-22

    申请号：US13384350

    申请日：2010-06-30

    Applicant: Athanassios Tzikas ,  Herbert Klier ,  Georg Roentgen

    Inventor： Athanassios Tzikas ,  Herbert Klier ,  Georg Roentgen

    IPC: C09B62/006

    CPC classification number: C09B62/4415 ,  C09D11/328

    Abstract: Reactive dyes of the formula (1) wherein B is an aliphatic bridging member, G is a sulfo naphthalene group or a sulfo benzene group of the formula (2a) or a pyridone radical of the formula (2b), R1, R2, R3 and R4 are each independently of the others hydrogen or unsubstituted or substituted C1-C4alkyl, (R5)h denotes h identical or different substituents selected from the group sulfo, C1-C4alkyl and C1-C4alkoxy, R6 is hydrogen, sulfo, halogen, carboxy, C1-C4alkyl, C1-C4alkoxy or a fiber-reactive group Z1 of the formula —SO2—Y (3a), —NH—CO—(CH2)1—SO2—Y (3b), —CONH—(CH2)m—SO2—Y (3c), —NH—CO—CH(Hal)-CH2-Hal (3d) or —NH—CO—C(Hal)=CH2 (3e), R7 is amino, C1-C4alkyl or a fiber-reactive group Z2 of the formula —NH—(CH2)n—SO2—Y (3a), (R8)j denotes j identical or different substituents selected from the group sulfo, C2-C4alkanoylamino, ureido, C1-C4alkyl and C1-C4alkoxy, R9 is hydrogen, C1-C4alkyl or C1-C4alkoxy, R10 is hydrogen or C1-C4alkyl, R11 is hydrogen, cyano, carbamoyl or sulfomethyl, and R12 is hydrogen, C1-C4alkyl, or phenyl which is unsubstituted or substituted by C1-C4alkyl, C1-C4alkoxy, C2-C4alkanoylamino, ureido, halogen or sulfo, X1 and X2 are halogen, Hal is chlorine or bromine, h and j are each independently of the other a number 0, 1 or 2; k is a number 1, 2 or 3; I, m and n are each independently of the other a number 2, 3 or 4, and Y is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, with the proviso that the dye of formula (1) contains at least one fiber-reactive group Z1 or Z2 are suitable for dyeing cellulosic or amide-group-containing fiber materials.

    Abstract translation: 式（1）的反应性染料，其中B是脂族桥连构件，G是式（2a）的磺基萘基或磺基苯基或式（2b）的吡啶酮基，R1，R2，R3和 R 4各自独立地为氢或未取代的或取代的C 1 -C 4烷基，（R 5）h表示相同或不同的选自磺基，C 1 -C 4烷基和C 1 -C 4烷氧基的取代基，R 6是氢，磺基，卤素，羧基， C1-C4烷基，C1-C4烷氧基或式-SO2-Y（3a）的纤维反应性基团Z1，-NH-CO-（CH2）1-SO2-Y（3b），-CONH-（CH2）m- SO2-Y（3c），-NH-CO-CH（Hal）-CH2-Hal（3d）或-NH-CO-C（Hal）= CH2（3e），R7是氨基，C1-C4烷基或纤维 - 式-NH-（CH2）n-SO2-Y（3a），（R8）j的反应性基团Z2表示j个相同或不同的选自磺基，C 2 -C 4烷酰基氨基，脲基，C 1 -C 4烷基和C 1 -C 4烷氧基 R 9是氢，C 1 -C 4烷基或C 1 -C 4烷氧基，R 10是氢或C 1 -C 4烷基，R 11是氢，氰基，氨基甲酰基或磺基甲基，和 R 12是氢，C 1 -C 4烷基或被C 1 -C 4烷基，C 1 -C 4烷氧基，C 2 -C 4烷酰基氨基，脲基，卤素或磺基取代的苯基，X 1和X 2是卤素，Hal是氯或溴，h和j是 每个独立于另一个数字0,1或2; k是数字1,2或3; I，m和n各自独立地为数2，3或4，Y为乙烯基或基团-CH 2 -CH 2 -U，U为在碱性条件下可除去的基团，条件是式 （1）含有至少一种纤维反应性基团Z 1或Z 2适于染色含纤维素或含酰胺基的纤维材料。

    Reactive dyes, a process for their preparation and their use
    16.
    发明授权
    Reactive dyes, a process for their preparation and their use 失效
    活性染料，其制备方法及其用途

    公开(公告)号：US07553340B2

    公开(公告)日：2009-06-30

    申请号：US11667616

    申请日：2005-11-02

    Applicant: Athanassios Tzikas ,  Georg Roentgen ,  Herbert Klier

    Inventor： Athanassios Tzikas ,  Georg Roentgen ,  Herbert Klier

    IPC: C09B67/22 ,  C07C245/00

    CPC classification number: C09B62/4415

    Abstract: Reactive dyes of formula (1) wherein R1 is hydrogen or unsubstituted or substituted C1-C4alkyl, R2 is hydrogen; C1-C4alkyl; C1-C4alkoxy unsubstituted or substituted by sulfato, hydroxy or by C1-C4alkoxy; halogen; carboxy or sulfo, R3 is hydrogen; C1-C4alkyl; C1-C4alkoxy unsubstituted or substituted by sulfato, hydroxy or by C1-C4alkoxy; halogen; nitro; C2-C4alkanoylamino; ureido; carboxy or sulfo, (R4)k denotes k identical or different substituents selected from the group halogen, C1-C4-alkyl, C1-C4alkoxy, carboxy and sulfo, X is halogen and V is a radical of formula (2a), 2(b) wherein R5 is unsubstituted or substituted C1-C4alkyl, (R6)I denotes I identical or different substituents from the group C1-C4alkyl, C1-C4alkoxy and sulfo, and I is the number 0, 1 or 2, Y is vinyl or a —CH2—CH2—U radical and U is a group that is removable under alkaline conditions, Q is a —CH(HaI)-CH2-HaI or —C(HaI)=CH2 group, Hal is halogen and k is the number 0, 1 , 2 or 3, are suitable especially for dyeing cotton and yield dyeings having good allround fastness properties.

    Abstract translation: 式（1）的反应性染料，其中R 1是氢或未取代的或取代的C 1 -C 4烷基，R 2是氢; C 1 -C 4烷基; 未被取代或被硫酸酯，羟基或被C 1 -C 4烷氧基取代的C 1 -C 4烷氧基; 卤素; 羧基或磺基，R 3是氢; C 1 -C 4烷基; 未被取代或被硫酸酯，羟基或被C 1 -C 4烷氧基取代的C 1 -C 4烷氧基; 卤素; 硝基 C 2 -C 4烷酰基氨基; 脲基 羧基或磺基，（R4）k表示k个相同或不同的选自卤素，C 1 -C 4 - 烷基，C 1 -C 4烷氧基，羧基和磺基的取代基，X是卤素，V是式（2a），2（ b）其中R 5为未取代的或被取代的C 1 -C 4烷基，（R 6）I表示与C 1 -C 4烷基，C 1 -C 4烷氧基和磺基基团相同或不同的取代基，I为0,1或2，Y为乙烯基或 -CH 2 -CH 2 -U基团，U是在碱性条件下可除去的基团，Q是-CH（H 1）-CH 2 -H a或-C（H 1）= CH 2基团，Hal是卤素，k是数 0,2,2或3，特别适用于染色棉和具有良好耐环牢性的产量染色。

    Mixtures of reactive dyes and their use
    17.
    发明授权
    Mixtures of reactive dyes and their use 失效
    活性染料的混合物及其用途

    公开(公告)号：US06630005B1

    公开(公告)日：2003-10-07

    申请号：US09831039

    申请日：2001-05-03

    Applicant: Athanassios Tzikas ,  Urs Lehmann ,  Herbert Klier

    Inventor： Athanassios Tzikas ,  Urs Lehmann ,  Herbert Klier

    IPC: C09B6200

    CPC classification number: C09B67/0051 ,  D06P1/38 ,  D06P3/66 ,  Y10S8/918

    Abstract: Dye mixtures, which comprise at least one dye of formula (1) together with at least one dye of formula (2), wherein R1, R2, R4 and R5 are each independently of one another hydrogen or unsubstituted or substituted C1-C4alkyl, (R3)0-2 is 0 to 2 identical or different substituents selected from the group consisting of C2-C4halogen alkanoylamino, C1-C4alkyl or C1-C4alkoxy, A1 and A2 are each independently of the other an unsubstituted or substituted phenylene radical or a C1-C8alkylene radical which may be interrupted by oxygen, D is a radical of formula (3) or (4) wherein is (R6)0-2 0 to 2 identical or different substituents selected from the group consisting of halogen, C2-C4alkanoylamino, C1-C4alkyl and C1-C4alkoxy, X1 and X2 are halogen, and Y1 and Y2 are each independently of the other a fiber-reactive radical of formula: —SO2—Z (5a): —CONH—(CH2)m—SO2—Z (5b); —NH—CO—CH(Hal)—CH2—Hal (5c).

    Abstract translation: 包含式（1）的至少一种染料与至​​少一种式（2）的染料的染料混合物，其中R 1，R 2，R 4和R 5各自彼此独立地为氢或未取代或取代的C 1 -C 4烷基（ R3）0-2为0〜2个相同或不同的选自C2-C4卤代烷酰基氨基，C1-C4烷基或C1-C4烷氧基的取代基，A1和A2各自独立地为未取代或取代的苯基或C1 可以被氧中断的-C8亚烷基，D是式（3）或（4）的基团，其中是（R6）0-2-0-2相同或不同的选自卤素，C 2 -C 4烷酰基氨基， C 1 -C 4烷基和C 1 -C 4烷氧基，X 1和X 2是卤素，并且Y 1和Y 2各自独立地为下式：-SO 2 -Z（5a）：-CONH-（CH 2）m -SO 2 - Z（5b）; -NH-CO-CH（Hal）-CH 2 - Hal（5c）。

    MIXTURES OF REACTIVE DYES AND THEIR USE IN A METHOD FOR TRICHROMATIC DYEING OR PRINTING
    20.
    发明申请
    MIXTURES OF REACTIVE DYES AND THEIR USE IN A METHOD FOR TRICHROMATIC DYEING OR PRINTING 有权
    反应性染料的混合物及其在三色染色或印刷方法中的应用

    公开(公告)号：US20100077555A1

    公开(公告)日：2010-04-01

    申请号：US12513464

    申请日：2007-10-30

    Applicant: Georg Roentgen ,  Athanassios Tzikas ,  Hubert Jean Luc Christnacher

    Inventor： Georg Roentgen ,  Athanassios Tzikas ,  Hubert Jean Luc Christnacher

    IPC: C09B62/095 ,  C09B62/012

    CPC classification number: C09B62/4407 ,  C09B62/4413 ,  C09B62/4415 ,  C09B67/005 ,  C09B67/0059

    Abstract: Dye mixtures, comprising at least one dye of formula and at least one dye from the group of formulae wherein Q1 is C1-C4alkyl, halogen or a radical —SO2—Z, Q2 and Q3 are each independently of the other C1-C4alkoxy, Q4 is C1-C4alkoxy, C1-C4alkyl, halogen or sulfo, Q5 is C1-C4alkoxy, C1-C4alkyl, C1-C4alkanoylamino, ureido, halogen or sulfo, R1, R2 and R3 are each independently of the others hydrogen or unsubstituted or substituted C1-C4alkyl, k and q are each independently of the other the number 0 or 1, n and p are each independently of the other the number 0, 1 or 2, m is the number 0, 1, 2 or 3, t is the number 1, 2 or 3, X1, X2 and X3 are each independently of the others halogen, 3-carboxypyridin-1-yl, 3-carbamoylpyridin-1-yl or a non-fibre-reactive substituent, and T1, T2 and T3 are each independently of the others a non-fibre-reactive substituent or a fibre-reactive radical of formula wherein (R4)0-2 denotes from 0 to 2 identical or different substituents from the group halogen, C1-C4alkyl, C1-C4alkoxy and sulfo, Z is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, Q is a group —CH(Hal)-CH2-Hal or —C(Hal)=CH2, and Hal is halogen, are suitable especially for the dichromatic or trichromatic dyeing or printing of cellulosic fibre materials and yield dyeings or prints having good reproducibility and good all-round fastness properties.

    Abstract translation: 染料混合物，其包含至少一种下式的染料和至少一种下式基团的染料，其中Q 1是C 1 -C 4烷基，卤素或基团-SO 2 -Z，Q 2和Q 3各自独立地为C 1 -C 4烷氧基，Q 4 C1-C4烷氧基，C1-C4烷基，卤素或磺基，Q5是C1-C4烷氧基，C1-C4烷基，C1-C4烷酰基氨基，脲基，卤素或磺基，R1，R2和R3各自独立地是氢或未取代的或取代的C1 -C 1-4烷基，k和q各自独立于数字0或1中的另一个，n和p各自独立于数字0,1或2中的另一个，m是数字0,1,2或3，t是 1,2或3个，X1，X2和X3各自独立地为卤素，3-羧基吡啶-1-基，3-氨基甲酰基吡啶-1-基或非纤维反应性取代基，T1，T2和T3 各自独立地为非纤维反应性取代基或具有下式的纤维反应性基团其中（R4）0-2表示0至2个相同或不同的取代基，基团卤素 ，C 1 -C 4烷基，C 1 -C 4烷氧基和磺基，Z是乙烯基或基团-CH 2 -CH 2 -U，U是在碱性条件下可除去的基团，Q是基团-CH（Hal）-CH 2 - Hal或-C（ Hal）= CH2，Hal是卤素，特别适用于纤维素纤维材料的二色或三色染色或印花，并且具有良好的再现性和良好的全面牢固性的产量染色或印花。

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