公开(公告)号：US3890257A

公开(公告)日：1975-06-17

申请号：US39857573

申请日：1973-09-19

Applicant: DU PONT

Inventor： JAMES DANIEL SHAW

IPC: C09B44/04 ,  C09B35/04 ,  C09B35/22 ,  C09B35/26

CPC classification number: C09B44/04 ,  Y10S8/929

Abstract: Disclosed herein are biscationic disazo dyes and a process for dyeing nylon therewith at a pH of about 4 to 7. The dyes have good exhaust and buildup on acidmodified BCF nylon fibers as well as good light-fastness and wet fastness on such fibers. The dyes have the formula

WHEREIN X is selected from -CH2-, -C(CH3)2-, -NH-, -O-, -OCH2(CH2)1-2O-, -OCH2CH(OH)CH2O-, -SO2-, -S-, -S-S-, -NHCO-, and -NHCONH-; R1 is selected from H, CH3, C2H5, Cl, and Br; R2 is selected from H, alkyl, alkoxy, Cl, NHCO-alkyl, and NHCOC6H5; R3 is selected from H, alkyl, and alkoxy; Y is selected from

WHEREIN N IS 0 OR 1; Z is H when n is O and Z is OH when n is 1; Q is selected from NR4R5R6, and NHCOCH2NR4R5R6; R4 is selected from alkyl, and hydroxyalkyl; R5 is selected from alkyl, hydroxyalkyl, and cyclohexyl; R6 is selected from H, alkyl and benzyl; R4 and R5, optionally, can form an alicyclic ring, or a heterocyclic ring including the nitrogen atom or, together with R6, can form a pyridinium ring; A is an anion.

Abstract translation: 本文公开了双阳离子双偶氮染料以及在约4至7的pH下染色尼龙的方法。该染料在酸改性的BCF尼龙纤维上具有良好的排气和积聚性，并且在这种纤维上具有良好的耐光牢度和耐湿牢度。 染料具有式WHEREIN X选自-CH 2 - ， - C（CH 3）2 - ， - NH - ， - O - ， - OCH 2（CH 2）1-2 O - ， - OCH 2 CH（OH）CH 2 O-，-SO 2 - ， - S - ， - S - ， - NHCO-和-NHCONH-; R1选自H，CH3，C2H5，Cl和Br; R2选自H，烷基，烷氧基，C1，NHCO-烷基和NHCOC6H5; R3选自H，烷基和烷氧基; Y +选自WHEREIN N IS 0 OR 1; 当n为0时，Z为H，当n为1时，Z为OH; Q +选自NR4R5R6和NHCOCH2NR4R5R6; R4选自烷基和羟基烷基; R5选自烷基，羟基烷基和环己基; R 6选自H，烷基和苄基; R4和R5任选地可以形成脂环族环，或包含氮原子的杂环，或者与R6一起可以形成吡啶鎓环; A < - >是阴离子。

公开(公告)号：US3912708A

公开(公告)日：1975-10-14

申请号：US35691073

申请日：1973-05-03

Applicant: DU PONT

Inventor： JAMES DANIEL SHAW

IPC: C09B44/04 ,  D06P1/66 ,  D06P3/24 ,  D06P3/82 ,  C09B29/08 ,  D06P3/26

CPC classification number: C09B44/04 ,  D06P1/66 ,  D06P3/241 ,  D06P3/242 ,  D06P3/8209

Abstract: Orange to violet biscationic azo dyes having the formula

where R1 alkyl R2 alkyl or hydroxyalkyl R3 alkyl, hydroxyalkyl or benzyl or R2 and R3 together alicyclic ring or R1, R2, and R3 together pyridinium ring R4 H or Cl W 1,4-naphthylene or

R5 and R6 H, alkyl, alkoxy or Cl R7 H, alkyl, alkoxy, Cl, NHCO alkyl or NHCOC6H5 R8 H, Cl, alkyl or alkoxy

Y N R9R2R3 or NHCOCH2N R9R2R3, where R9 R1 or H m 0 or 1 N 0 OR 1 Z H when n 0 and OH when n 1 A anion AND WHERE ALKYL GROUPS CONTAIN 1-4 CARBON ATOMS, ARE PARTICULARLY WELL SUITED FOR DYEING OF BULK CONTINUOUS FILAMENT (BCF) nylon styling carpet, and have good exhaust and lightfastness on acid-modified nylon and excellent reserve on unmodified nylons, at the preferred dyeing pH range of 6-6.5. The dyes are prepared by coupling p-aminophenacylammonium or p-(paminophenylazo)phenacylammonium salts to N,N-disubstituted anilines containing a pendant tertiary amine or quaternary ammonium group attached to the nitrogen atom.

Abstract translation: 具有下式的橙色至紫色双阳离子偶氮染料R4 | R1R2R3N + CH2CO R8 | -N = NWN = N）mX + 2A | R7其中R1 =烷基R2 =烷基或羟基烷基R3 =烷基，羟基烷基或 苄基或R 2和R 3一起=脂环族环或R1，R2和R3一起=吡啶鎓环R4 = H或ClW = 1,4-亚萘基或R5 | - ，| R5 R5和R6 = H，烷基，烷氧基或C1- R 7 = H，烷基，烷氧基，Cl，NHCO烷基或NHCOC 6 H 5 R 8 = H，Cl，烷基或烷氧基烷基烷基X + = -NN ANGLE或-N ANGLE烷基CH 2 CH（CH 2）n Y + Z n + = N + R 9 R 2 R 3或NHCOCH 2 N + R 9 R R R 3，其中当n = 0时，R 9 = R 1或H m = 0或1 N = 0或1 Z = H，当n = 1时， =阴离子和含有1-4碳原子的碱性基团，特别适用于大量连续纤维（BCF）尼龙造型地毯的染色，在酸改性尼龙上具有良好的排气和耐光性，在未改性尼龙上具有优异的保留性， 在优选的染色pH范围为6-6.5。 通过将对氨基苯甲酰基铵或对 - （对氨基苯基偶氮）苯甲酰甲基铵盐偶联到含有与氮原子连接的叔胺或季铵基团的N，N-二取代的苯胺来制备染料。

公开(公告)号：US3649162A

公开(公告)日：1972-03-14

申请号：US3649162D

申请日：1970-07-27

Applicant: DU PONT

Inventor： JAMES DANIEL SHAW

IPC: C09B44/04

CPC classification number: C09B44/04 ,  Y10S8/924

Abstract: Red to rubine biscationic monoazo dyes having the formula

WHEREIN R1 and R2 H, alkyl or phenyl R3 alkyl or benzyl R4 H, alkyl, alkoxy, Cl, NHCO alkyl or NHCOC6H5 R5 Cl, alkyl or alkoxy
WHEREIN R6 alkyl R7 alkyl or hydroxyalkyl R8 alkyl, hydroxyalkyl or benzyl or R7 and R8 together are piperidino or pyrrolidino R6, R7 and R8 together or pyridinium A is anion and ALKYL ONE TO FOUR CARBON ATOMS ARE USEFUL FOR DYEING NYLON STYLING YARNS, HAVE BRIGHT SHADES WITH GOOD BUILDUP AND LIGHTFASTNESS ON ACID-MODIFIED NYLON WITH NEGLIGIBLE AFFINITY FOR UNMODIFIED NYLONS WHEN DYED THEREON AT A PH of from about 6 to about 6.5.

WHEREIN N O or 1 Z H when n O Z OH when n 1

Abstract translation: 红色至具有式WHEREIN R 1和R 2 = H的烷基或苯基R 3 =烷基或苄基R 4 = H，烷基，烷氧基，Cl，NHCO烷基或NHCOC 6 H 5 R 5 = Cl，烷基或烷氧基的芳基双阳离子单偶氮染料，其中N = O 当n = 1时，当n = OZ = OH时，Z = H，其中R6 =烷基R7 =烷基或羟基烷基R8 =烷基，羟基烷基或苄基或R7和R8一起是哌啶子基或吡咯烷子基R6，R7和R8一起或吡啶鎓A < - >是阴离子，ALKYL =一碳三氧化钛可用于染色尼龙标准纱线，具有良好的建筑和亮度的酸性修饰尼龙的明亮色调，对于未修饰的尼龙，当其在PH约为6至6时，具有可忽略的亲和力 约6.5。

公开(公告)号：US3910876A

公开(公告)日：1975-10-07

申请号：US35690973

申请日：1973-05-03

Applicant: DU PONT

Inventor： JAMES DANIEL SHAW

IPC: C09B44/04 ,  D06P1/66 ,  D06P3/24 ,  D06P3/82 ,  C09B31/02 ,  D06P3/26

CPC classification number: D06P3/8209 ,  C09B44/04 ,  D06P1/66 ,  D06P3/241 ,  D06P3/242

Abstract: Y N R9R2R3 or NHCOCH2N R9R2R3, where R9 R1 or H m 0 or 1 N 0 OR 1 Z H when n 0 and OH when n 1 A anion AND WHERE ALKYL GROUPS CONTAIN 1-4 CARBON ATOMS, ARE PARTICULARLY WELL SUITED FOR DYEING OF BULK CONTINUOUS FILAMENT (BCF) nylon styling carpet, and have good exhaust and lightfastness on acid-modified nylon and excellent reserve on unmodified nylons, at the preferred dyeing pH range of 6-6.5. The dyes are prepared by coupling p-aminophenacylammonium or p-(paminophenylazo)phenacylammonium salts to N,N-disubstituted anilines containing a pendant tertiary amine or quaternary ammonium group attached to the nitrogen atom.
Orange to violet biscationic azo dyes having the formula

where R1 alkyl R2 alkyl or hydroxyalkyl R3 alkyl, hydroxyalkyl or benzyl OR R2 and R3 together alicyclic ring OR R1, R2, and R3 together pyridinium ring R4 H or Cl W 1,4-naphthylene or
R5 and R6 H, alkyl, alkoxy or Cl R7 H, alkyl, alkoxy, Cl, NHCO alkyl or NHCOC6H5 R8 H, Cl, alkyl or alkoxy

Abstract translation: 其中R1 =烷基R2 =烷基或羟基烷基R3 =烷基，羟基烷基或苄基ORR2和R3一起=脂环族环OR = R1，R2和R3一起=吡啶鎓环R4 = H或ClW = 1,4-亚萘基或R5和R6 = H，烷基，烷氧基或C1 R7 = H，烷基，烷氧基，C1，NHCO烷基或NHCOC6H5 R8 = H，Cl，烷基或烷氧基+烷基烷基X + = - NN ANGLE或-N ANGLE烷基CH2CH（CH2）nY + | ZY + = N + R9R2R3或NHCOCH2N + R9R2R3，其中 当n = 0时，R9 = R1或H m = 0或1 N = 0或1 Z = H，当n = 1时，OH是OH，阴离子和含1-4个碳原子的烷基，特别是 染色连续纤维（BCF）尼龙造型地毯，在酸改性尼龙上具有良好的排气和耐光性，在未改性尼龙上具有优良的储备，优选的染色pH范围为6-6.5。 通过将对氨基苯甲酰基铵或对 - （对氨基苯基偶氮）苯甲酰甲基铵盐偶联到含有与氮原子连接的叔胺或季铵基团的N，N-二取代的苯胺来制备染料。

公开(公告)号：US3904358A

公开(公告)日：1975-09-09

申请号：US35690873

申请日：1973-05-16

Applicant: DU PONT

Inventor： JAMES DANIEL SHAW

IPC: C09B44/04 ,  D06P1/66 ,  D06P3/24 ,  D06P3/82 ,  D06P1/06

CPC classification number: C09B44/04 ,  D06P1/66 ,  D06P3/241 ,  D06P3/242 ,  D06P3/8209 ,  Y10S8/922 ,  Y10S8/929

Abstract: Orange to violet biscationic azo dyes having the formula

WHERE R1 alkyl R2 alkyl or hydroxyalkyl R3 alkyl, hydroxyalkyl or benzyl OR R2 and R3 together alicyclic ring OR R1, R2, and R3 together pyridinium ring R4 H or Cl W 1,4-naphthylene or

R5 and R6 H, alkyl, alkoxy or Cl R7 H, alkyl, alkoxy, Cl, NHCO alkyl or NHCOC6H5 R8 H, Cl, alkyl or alkoxy

Y N R9R2R3 or NHCOCH2N R9R2R3, where R9 R1 or H m 0 or 1 N 0 OR 1 Z H when n O and OH when n 1 A anion AND WHERE ALKYL GROUPS CONTAIN 1-4 CARBON ATOMS, ARE PARTICULARLY WELL SUITED FOR DYEING OF BULK CONTINUOUS FILAMENT (BCF) nylon styling carpet, and have good exhaust and lightfastness on acid-modified nylon and excellent reserve on unmodified nylons, at the preferred dyeing pH range of 6-6.5. The dyes are prepared by coupling p-aminophenacylammonium or p-(paminophenylazo)phenacylammonium salts to N,N-disubstituted anilines containing a pendant tertiary amine or quaternary ammonium group attached to the nitrogen atom.

Abstract translation: 橙色至紫色双阳离子偶氮染料，具有下式：其中R1 =烷基R2 =烷基或羟烷基R3 =烷基，羟烷基或苄基OR R2和R3一起=脂环族OR R1，R2和R3一起=吡啶鎓环R4 = H或ClW = 1,4-亚萘基或R 5和R 6 = H，烷基，烷氧基或Cl R 7 = H，烷基，烷氧基，Cl，NHCO烷基或NHCOC 6 H 5 R 8 = H，Cl，烷基或烷氧基Y + = N + R9R2R3或NHCOCH2N + R9R2R3，其中当n = 0时，R9 = R1或Hm = 0或1N = 0或1Z = H，当n = 1时，A =阴离子和碱金属基团含有1- 4碳酸钙，特别适合用于大量连续纤维（BCF）尼龙造型地毯的染色，在酸改性尼龙上具有良好的排气和耐光性，在未改性尼龙上具有优异的储备，优选的染色pH范围为6- 6.5。 通过将对氨基苯甲酰基铵或对 - （对氨基苯基偶氮）苯甲酰甲基铵盐偶联到含有与氮原子连接的叔胺或季铵基团的N，N-二取代的苯胺来制备染料。

公开(公告)号：US3646072A

公开(公告)日：1972-02-29

申请号：US3646072D

申请日：1970-07-27

Applicant: DU PONT

Inventor： JAMES DANIEL SHAW

IPC: C09B1/50 ,  C09B1/515

CPC classification number: C09B1/501 ,  C09B1/515

Abstract: ACID MODIFIED BULK CONTINUOUS FILAMENT NYLON FIBERS CAN BE DYED IN TURQUOISE SHADES WITH BISCATIONIC ANTHRAQUINONE DYES PREPARED BY QUARTERNIZING THE BISCONDENSATION PRODUCT OF AN N,N-DISUBSTITUTED C2-4 ALKYLENEDIAMINE AND 1,4,5,8-TETRAHYDROXYANTHRAQUINONE. THE BISCATIONIC DYES HAVE EXCELLENT RESERVE ON UNMODIFIED NYLON FIBERS AND FIBERS SO DYED HAVE SUFFICIENT LIGHT FASTNESS FOR USE IN NYLON STYLING CARPETING.