公开(公告)号：US07456316B2

公开(公告)日：2008-11-25

申请号：US10508714

申请日：2003-03-13

Applicant: Urs Lauk ,  Patric Nowack

Inventor： Urs Lauk ,  Patric Nowack

IPC: C07C211/00

CPC classification number: C09B1/5145 ,  C08K5/0041 ,  C09B1/32 ,  C09B1/60 ,  G02B5/22

Abstract: The present invention relates to a compound of formula (I) wherein R1 is a radical of formula (II) R2 is —NH2 or a radical of formula (II), R3 and R4 are each independently of the other hydrogen, hydroxy, —NH2 or a radical of formula (II), R5 is hydrogen, halogen or —X—(CH2)n—Y, wherein X is a direct bond, —O— or —S—, Y is —OH or —OSO3H and n is a number from 0 to 6, with the proviso that at least one of the radicals R3, R4 and R5 is not hydrogen, to a process for the preparation thereof and to the use thereof in a method of producing mass-coloured plastics or polymeric colour particles.

Abstract translation: 本发明涉及式（I）化合物，其中R 1是式（II）的基团R 2是-NH 2 N 或式（II）的基团，R 3和R 4各自独立地为氢，羟基，-NH 2或另一个 式（II）的基团，R 5是氢，卤素或-X-（CH 2）n）-N，其中X是 直接键，-O-或-S-，Y是-OH或-OSO 3 H，n是0至6的数，条件是至少一个基团R _{3，R 4和R 5不是氢，其制备方法及其在生产大量着色的方法中的用途 塑料或聚合物色颗粒。}

公开(公告)号：US20070220688A1

公开(公告)日：2007-09-27

申请号：US10572233

申请日：2004-09-17

Applicant: Man-joon Han ,  Soon-hyun Park ,  Jwung-rhok Kim ,  Urs Lauk

Inventor： Man-joon Han ,  Soon-hyun Park ,  Jwung-rhok Kim ,  Urs Lauk

IPC: D06P5/00 ,  C07C51/235 ,  C07D265/30 ,  C07D307/20 ,  C07D307/77 ,  C07D309/10

CPC classification number: C07C51/093 ,  C07C51/29 ,  C07D295/155 ,  C07D295/24 ,  C07D307/12 ,  C07D307/16 ,  C07D309/04 ,  C07D309/06 ,  C07D333/44 ,  C07D493/04 ,  D06P5/00 ,  C07C59/64 ,  C07C59/68

Abstract: The present invention provides α-hydroxy benzeneacetic acid derivatives of the formula as defined in the specification which is a precursor indispensable for synthesis of compounds having two 5-membered lactone rings fused to central cyclohexa-1,4-diene nucleus, and a process of easily preparing the same. According to the preparation process of the present invention, the α-hydroxy benzeneacetic acid derivative can be readily prepared at high purity and yield without using toxic materials or producing toxic by-products. Some novel compounds, synthesized by using such a x-hydroxy benzeneacetic acid derivative, have excellent fastness properties, dye fixing rate and leveling property to general synthetic fiber materials such as polyester fibers and their blends with other fibers, especially to micro fibers, and also can be used as a coloring agent for plastic resins, color tonors, color filters, etc.

Abstract translation: 本发明提供了本说明书中定义的式 - 羟基苯乙酸衍生物，其是合成具有与中心环己1,4-二烯核心融合的两个5元内酯环的化合物不可缺少的前体，以及 容易准备相同。 根据本发明的制备方法，α-羟基苯乙酸衍生物可以在不使用有毒物质或产生有毒副产物的情况下以高纯度和高产率容易地制备。 通过使用这种x-羟基苯乙酸衍生物合成的一些新型化合物对于一般的合成纤维材料如聚酯纤维及其与其它纤维，特别是微纤维的共混物具有优异的牢度性能，染色定影率和流平性，以及 可用作塑料树脂，彩色调色剂，滤色片等的着色剂。

公开(公告)号：US07026459B2

公开(公告)日：2006-04-11

申请号：US10508713

申请日：2003-03-13

Applicant: Romeo Dreier ,  Urs Lauk

Inventor： Romeo Dreier ,  Urs Lauk

IPC: C09B29/42 ,  C08K5/3432 ,  G02B5/22 ,  G03F7/00

CPC classification number: C08K5/0041 ,  C09B29/3639 ,  G02B5/22

Abstract: The present invention relates to an azo dye of formula (I) wherein R1 and R2 are each independently of the other —NH—(CH2CH2)—OH, —NH—CH2—CHOH—CH2—OH, —NH—(CH2CH2)—S—(CH2CH2)—OH, —NH—(CH2CH2)—NH—(CH2CH2)—OH, NH—CH2CH2—CON(CH2CH2OH)2, R3 is —CN or —CONH2, R4 is methyl or trifluoromethyl, R5 is —CF3, —COOC2H5, R6 is hydrogen or chlorine and R7 is hydrogen, chlorine, bromine or —NO2, to a process for the preparation thereof and to the use thereof in a method of producing mass-coloured plastics or polymeric colour particles

Abstract translation: 本发明涉及式（I）的偶氮染料，其中R 1和R 2各自独立地为其它的-NH-（CH 2） CH 2 -CH 2 -CH 2，-NH-CH 2 -CHOH-CH 2 -OH，-NH-（CH 2 CH 2） 2 CH 2）-S-（CH 2 CH 2 CH 2）-OH，-NH-（CH 2） NH 2 - （CH 2 CH 2） - OH，NH-CH 2 2 CH 2 CO 2（CH 2 CH 2 CH 2）2 CH 2，R 3 是-CN或-CONH 2，R 4是甲基或三氟甲基，R 5是-CF 3， ，-COOC 2 H 5，R 6是氢或氯，R 7是氢，氯，溴 或-NO 2 2，其制备方法及其在制备大量着色的塑料或聚合物着色颗粒的方法中的用途

公开(公告)号：US07005507B2

公开(公告)日：2006-02-28

申请号：US10470039

申请日：2002-01-18

Applicant: Yvonne Pichler ,  Urs Lauk

Inventor： Yvonne Pichler ,  Urs Lauk

IPC: C09B29/42 ,  D06P1/18

CPC classification number: C09B67/0051 ,  C09B29/0059 ,  C09B29/3639 ,  Y10S8/92

Abstract: The present invention relates to an azo dye of formula (1), wherein R1 is the radical of a diazo component of the benzene, naphthalene, diphenyl, azobenzene, thiophene, benzothiazole, thiadiazole, indazole, benzatriazole, pyrazole, anthraquinone, naphtholic acid imide, chromone, phthalimide or diphenylene oxide series, R2 is an unsubstitued or substitued aryl radical or an unsubstituted or substituted aralkyl radical and R3 is an unsubstituted or substituted aryl radical or an unsubstituted or substituted aralkyl radical, with the proviso that one of the substituents R2 and R3 is an unsubstituted or substituted aryl radical and the other is an unsubstituted or substituted aralkyl radical, 2-hydroxy-2-phenylethyl being expected as a substituted aralkyl radical, to mixtures comprising at least two structually different azo dyes of formula (1) and to the use of those azo dyes and dye mixtures in the dyeing or printing of semi-synthetic or synthetic hydrophobic fibre materials.

Abstract translation: 本发明涉及式（1）的偶氮染料，其中R 1是苯，萘，二苯基，偶氮苯，噻吩，苯并噻唑，噻二唑，吲唑，苯并三唑的重氮组分的基团 吡唑，蒽醌，萘甲酰亚胺，色酮，邻苯二甲酰亚胺或二苯醚系列，R 2是未取代的或取代的芳基或未取代或取代的芳烷基，R 3' 是未取代或取代的芳基或未取代或取代的芳烷基，条件是取代基R 2和R 3中的一个是未取代或取代的芳基， 另一个是未取代或取代的芳烷基，预期为取代的芳烷基的2-羟基-2-苯乙基与包含至少两种结构不同的式（1）的偶氮染料的混合物和使用那些偶氮染料和染料 半合成染色或印刷中的混合物 c或合成疏水纤维材料。

公开(公告)号：US5554734A

公开(公告)日：1996-09-10

申请号：US460176

申请日：1995-06-02

Applicant: Urs Lauk

Inventor： Urs Lauk

IPC: C09B33/16 ,  C09B43/16 ,  C09B56/04 ,  C09B62/08 ,  D06P3/66 ,  D06P3/87

CPC classification number: C09B43/16 ,  C09B56/04 ,  C09B62/082

Abstract: Azo dyes of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 alkyl,R.sub.5 and R.sub.6 are each independently of the other hydrogen, halogen, or unsubstituted or hydroxy-substituted C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; C.sub.2 -C.sub.4 alkanoylamino which is unsubstituted or substituted in the alkyl moiety by hydroxy or C.sub.1 -C.sub.4 alkoxy, or ureido which is unsubstituted or substituted in the amino end group by one or two C.sub.1 -C.sub.4 alkyl groups,Y.sub.1 and Y.sub.2 are each independently of the other amino, N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxy, sulfo, carboxy or C.sub.1 -C.sub.4 alkoxy; C.sub.5 -C.sub.7 cycloalkylamino which is unsubstituted or substituted in the. cycloalkyl ring by C.sub.1 -C.sub.4 alkyl; phenylamino or N-C.sub.1 -C.sub.4 alkyl-N-phenylamino which are each unsubstituted or substituted in the phenyl ring by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, carboxy, sulfo or halogen; or morpholino or piperidin-1-yl, andA.sub.1 and A.sub.2 are each independently of the other unsubstituted or substituted phenyl or naphthyl, are direct dyes for different substrates, especially cellulosic fibre materials. They are high-temperature stable and are therefore particularly suitable for dyeing polyester/cotton blends with a disperse dye for the polyester fibres under the conditions for dyeing polyester fibres in a single-step, one-bath process.

Abstract translation: 式（1）的偶氮染料其中R1，R2，R3和R4各自独立地为氢或未取代或取代的C1-C4烷基，R5和R6各自独立地为氢，卤素或未取代或羟基 取代的C 1 -C 4烷基或C 1 -C 4烷氧基; 在烷基部分未被取代或被羟基或C 1 -C 4烷氧基取代的C 2 -C 4烷酰基氨基或在氨基端基中被一个或两个C 1 -C 4烷基取代的脲基，Y 1和Y 2各自独立地为其它氨基 未被取代或在烷基部分被羟基，磺基，羧基或C 1 -C 4烷氧基取代的N-单或N，N-二-C 1 -C 4烷基氨基; 未取代或未取代的C 5 -C 7环烷基氨基。 C1-C4烷基的环烷基环; 苯基氨基或N-C 1 -C 4烷基-N-苯基氨基，其各自未被取代或在苯环中被C1-C4烷基，C1-C4烷氧基，羧基，磺基或卤素取代; 或吗啉代或哌啶-1-基，而A1和A2各自独立地为其它未取代或取代的苯基或萘基，是用于不同底物，特别是纤维素纤维材料的直接染料。 它们是高温稳定的，因此特别适用于在单步一浴工艺中在用于染色聚酯纤维的条件下用聚酯纤维的分散染料染色聚酯/棉混纺织物。

公开(公告)号：US5328995A

公开(公告)日：1994-07-12

申请号：US9427

申请日：1993-01-27

Applicant: Rudolf Schaulin ,  Urs Lauk

Inventor： Rudolf Schaulin ,  Urs Lauk

IPC: C07D251/18 ,  C07C245/08 ,  C07D251/12 ,  C07D251/48 ,  C07D251/50 ,  C07D251/52 ,  C07D251/70 ,  C09B33/06 ,  C09B33/08 ,  C09B43/11 ,  C09B43/16 ,  C09B62/04 ,  C09B62/09 ,  C09D11/00 ,  D06P1/18 ,  D06P1/382 ,  D06P3/24 ,  D06P3/62 ,  D06P3/66 ,  D06P3/82 ,  D06P3/04

CPC classification number: C09B43/11 ,  C09B43/16 ,  C09B62/043 ,  C09B62/09

Abstract: The compounds of the formula ##STR1## where the substituents are as defined in claim 1, are direct dyes for various substrates, in particular cellulosic fibre materials. They are high temperature resistant and therefore are particularly highly suitable for the one-bath, single-stage dyeing of polyester/cotton blend fabrics with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.

Abstract translation: 取代基如权利要求1中所定义的式（IMA）（1）的化合物是用于各种底物，特别是纤维素纤维材料的直接染料。 它们耐高温，因此特别适用于在聚酯纤维的染色条件下，聚酯/棉混纺织物与聚酯纤维分散染料的单浴，单​​级染色。

公开(公告)号：US5223000A

公开(公告)日：1993-06-29

申请号：US784200

申请日：1991-10-28

Applicant: Urs Lauk

Inventor： Urs Lauk

IPC: C07D519/00 ,  C07D498/04 ,  C09B19/00 ,  C09B19/02 ,  C09B62/503 ,  C09B67/22 ,  D06P1/38 ,  D06P3/62 ,  D06P3/66 ,  D06P3/82

CPC classification number: C07D498/04 ,  C09B19/02 ,  C09B67/0034 ,  D06P3/62 ,  D06P3/66 ,  D06P3/8223 ,  Y10S8/917 ,  Y10S8/918 ,  Y10S8/922 ,  Y10S8/924

Abstract: Mixtures of different oligomer compounds of formula (1) are suitable for use as direct dyes for dyeing and printing a wide range of materials, especially cellulose fibers, to give dyeings and prints of good all-round fastness properties: ##STR1## wherein R.sub.1 is hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or aralkyl, R independently has the meaning of R.sub.1 or is an unsubstituted or substituted heteroaryl radical or a radical of formula ##STR2## wherein R.sub.4 is unsubstituted or substituted alkyl, cycloalkyl, aryl, aralkyl or heteroaryl, A is an unsubstituted or substituted alkylene, cycloalkylene, arylene or aralkylene radical, X is --O--, --S-- or --N(R.sub.5)--, wherein R.sub.5 is hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or aralkyl, or wherein the group ##STR3## is an unsubstituted or substituted heterocyclic radical, Y is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, sulfo, carboxy, carbamoyl, N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylcarbamoyl, N-phenyl- or N,N-diphenylcarbamoyl, sulfamoyl, N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylsulfamoyl or N-phenyl- or N,N-diphenylsulfamoyl, Z is hydroxy or unsubstituted or substituted alkyl, aryl or aralkyl, R.sub.2 and R.sub.3 are each independently of the other hydrogen, halogen, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, unsubstituted or substituted phenyl, benzyl, benzoylamino or phenoxy, sulfo, carboxy, carbamoyl, phenylcarbamoyl or C.sub.2 -C.sub.5 alkanoylamino, B is a bivalent organic linking group, m is an integer from 1 to 6 and n and p are each independently of the other 0 or 1, with the proviso that the different compounds of formula (1) of the mixture of oligomers differ solely in the value of m.

Abstract translation: 式（1）的不同低聚物化合物的混合物适合用作染色和印刷各种材料，特别是纤维素纤维的直接染料，以提供良好的全面牢度特性的染色和印刷：（1） 其中R 1是氢或未取代的或取代的烷基，环烷基，芳基或芳烷基，R独立地具有R 1的含义，或者是未取代或取代的杂芳基或式的基团，其中R 4是未取代的或取代的烷基， 环烷基，芳烷基或杂芳基，A是未取代或取代的亚烷基，亚环烷基，亚芳基或亚芳基，X是-O - ， - S-或-N（R5） - ，其中R5是氢或未取代的或取代的烷基， 环烷基，芳基或芳烷基，或其中基团为未取代或取代的杂环基，Y为C1-C4烷基，C1-C4烷氧基，卤素，磺基，羧基，氨基甲酰基，N-单或N， C 1 -C 4烷基氨基甲酰基，N-苯基 - 或N，N-二苯基氨基甲酸 氨基磺酰基，N-单或N，N-二-C 1 -C 4烷基氨磺酰基或N-苯基 - 或N，N-二苯基氨磺酰基，Z是羟基或未取代或取代的烷基，芳基或芳烷基，R 2和R 3各自独立地为 另一个氢，卤素，氰基，C1-C4烷基，C1-C4烷氧基，未取代或取代的苯基，苄基，苯甲酰氨基或苯氧基，磺基，羧基，氨基甲酰基，苯基氨基甲酰基或C2-C5烷酰基氨基，B是二价有机连接基团，m是 1至6的整数，n和p各自独立地为0或1，条件是低聚物混合物的不同的式（1）化合物仅在m的值上不同。

公开(公告)号：US20050182247A1

公开(公告)日：2005-08-18

申请号：US10516440

申请日：2003-05-27

Applicant: Athanassios Tzikas ,  Antoine Clement ,  Urs Lauk

Inventor： Athanassios Tzikas ,  Antoine Clement ,  Urs Lauk

IPC: C07D213/36 ,  C09B29/01 ,  C09B35/031 ,  C09B35/039 ,  C09B56/12 ,  C09B69/10 ,  C07D41/02

CPC classification number: C09B35/031 ,  C09B29/0022 ,  C09B35/039 ,  C09B69/106

Abstract: The present invention relates to an azo dye of formula I, II or III: (formula I, II or III); wherein R1 and R2 are each independently of the other one or more divalent groups selected from alkylene, arylene, aralkylene and cycloalkylene, which may be interrupted by —O—, —S—, —NH—, —NR8—, —COO—, —CONH— or —CONR9—, wherein R8 and R9 are alkyl or aryl, X is —O— or —NH—, R3 is —CN or —CONH2, R4 is methyl or trifluoromethyl and R5, R6, R7 and R8 are each independently of the others hydrogen, halogen or —CN, to a process for the preparation thereof and to the use thereof in a method of producing mass-coloured plastics or polymeric colour particles.

Abstract translation: 本发明涉及式I，II或III的偶氮染料：（式I，II或III）; 其中R 1和R 2各自独立地选自亚烷基，亚芳基，亚芳基和亚环烷基的另一个或多个二价基团，其可以被-O-， -S - ， - NH - ， - NR 8 - ， - COO - ， - CONH-或-CONR 9 - ，其中R 8 - R 9是烷基或芳基，X是-O-或-NH-，R 3是-CN或-CONH 2，R R 4是甲基或三氟甲基，R 5，R 6，R 7和R 8， 其各自独立地为氢，卤素或-CN，其制备方法及其在制备大量着色的塑料或聚合物着色颗粒的方法中的用途。

公开(公告)号：US20050150061A1

公开(公告)日：2005-07-14

申请号：US10508714

申请日：2003-03-13

Applicant: Urs Lauk ,  Patric Nowack

Inventor： Urs Lauk ,  Patric Nowack

IPC: G02B5/20 ,  C08J3/22 ,  C08K5/00 ,  C08K5/18 ,  C09B1/32 ,  C09B1/514 ,  C09B1/60 ,  G02B5/22 ,  D06P3/52

CPC classification number: C09B1/5145 ,  C08K5/0041 ,  C09B1/32 ,  C09B1/60 ,  G02B5/22

Abstract: The present invention relates to a compound of formula (I) wherein R1 is a radical of formula (II) R2 is —NH2 or a radical of formula (II), R3 and R4 are each independently of the other hydrogen, hydroxy, —NH2 or a radical of formula (II), R5 is hydrogen, halogen or —X—(CH2)n—Y, wherein X is a direct bond, —O— or —S—, Y is —OH or —OSO3H and n is a number from 0 to 6, with the proviso that at least one of the radicals R3, R4 and R5 is not hydrogen, to a process for the preparation thereof and to the use thereof in a method of producing mass-coloured plastics or polymeric colour particles.

Abstract translation: 本发明涉及式（I）化合物，其中R 1是式（II）的基团R 2是-NH 2 N 或式（II）的基团，R 3和R 4各自独立地为氢，羟基，-NH 2或另一个 式（II）的基团，R 5是氢，卤素或-X-（CH 2）n）-N，其中X是 直接键，-O-或-S-，Y是-OH或-OSO 3 H，n是0至6的数，条件是至少一个基团R _{3，R 4和R 5不是氢，其制备方法及其在生产大量着色的方法中的用途 塑料或聚合物色颗粒。}

公开(公告)号：US06555664B1

公开(公告)日：2003-04-29

申请号：US09869503

申请日：2001-06-28

Applicant: Urs Lauk ,  Antoine Clément ,  Romeo Dreier ,  Alfons Arquint

Inventor： Urs Lauk ,  Antoine Clément ,  Romeo Dreier ,  Alfons Arquint

IPC: C09B29036

CPC classification number: C09B43/42 ,  C09B29/0033 ,  C09B29/0809 ,  Y10S8/922

Abstract: The present invention relates to dyes of formula wherein R is methyl or butyl, R1 is hydrogen, halogen, cyano or nitro, R2 is halogen or cyano, R3 is hydrogen, halogen, C1-C4alkyl or C1-C4alkoxy, R4 is hydrogen, C1-C4alkyl, halogen, CF3 or —NHCOR7 wherein R7 is C1-C4alkyl, R5 is C1-C6alkyl that is unsubstituted or substituted by hydroxy, cyano, acyloxy,  or by phenoxy, x being a number from 0 to 4 and it being possible for the alkyl chain, from C2 upwards, optionally to be interrupted by one or more oxygen atoms, or is a radical of formula —CH2CH2—O—COR8, of formula  or of formula  and R6 is a radical of formula —CH2CH2—O—COR8 or of formula  R8 and R9 each independently of the other being C1-C4alkyl and R10 being hydrogen or C1-C4alkyl, or, when R is methyl, R5 and R6 are each independently of the other C1-C4alkyl, with the proviso that when R is n-butyl and R5 and/or R6 is/are a radical of formula —CH2CH2—O—COR8, R4 may not be chlorine or acetylamino, and also to the process for the preparation thereof and to the use thereof in dyeing or printing fibre materials, especially polyester-containing textile materials.

Abstract translation: 本发明涉及式Ⅳ的染料是甲基或丁基，R 1是氢，卤素，氰基或硝基，R 2是卤素或氰基，R 3是氢，卤素，C 1 -C 4烷基或C 1 -C 4烷氧基，R 4是氢，C 1 -C 4烷基 ，卤素，CF 3或-NHCOR 7，其中R 7为C 1 -C 4烷基，R 5为未取代或被羟基，氰基，酰氧基或苯氧基取代的C 1 -C 6烷基，x为0至4的数， 链，从C2向上，任选地被一个或多个氧原子中断，或者是式或结构式的基团-CH 2 CH 2 -O-COR 8，并且R 6是式-CH 2 CH 2 -O-COR 8的基团或式 式R 8和R 9各自独立地为C 1 -C 4烷基，R 10为氢或C 1 -C 4烷基，或者当R为甲基时，R 5和R 6各自独立地为C 1 -C 4烷基，条件是当R为n 丁基和R 5和/或R 6是式-CH 2 CH 2 -O-COR 8的基团，R 4可以不是氯或乙酰氨基，也可以是制备物的方法 以及其在染色或印花纤维材料，特别是含聚酯的纺织材料中的应用。