CN1289610C - 新的甲活性染料 - Google Patents
新的甲活性染料 Download PDFInfo
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- CN1289610C CN1289610C CNB028150023A CN02815002A CN1289610C CN 1289610 C CN1289610 C CN 1289610C CN B028150023 A CNB028150023 A CN B028150023A CN 02815002 A CN02815002 A CN 02815002A CN 1289610 C CN1289610 C CN 1289610C
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- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 title abstract 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 title abstract 2
- 239000000985 reactive dye Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000004043 dyeing Methods 0.000 claims abstract description 23
- 238000007639 printing Methods 0.000 claims abstract description 8
- 239000000758 substrate Substances 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 11
- 239000000976 ink Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 5
- 239000001913 cellulose Substances 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000000975 dye Substances 0.000 abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000000034 method Methods 0.000 description 5
- 238000004061 bleaching Methods 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001354 calcination Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- -1 halogen pyrimidines Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000000176 photostabilization Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- NTSYSQNAPGMSIH-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine Chemical compound FC1=CC(F)=NC(F)=N1 NTSYSQNAPGMSIH-UHFFFAOYSA-N 0.000 description 1
- SIXYIEWSUKAOEN-UHFFFAOYSA-N 3-aminobenzaldehyde Chemical compound NC1=CC=CC(C=O)=C1 SIXYIEWSUKAOEN-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000322338 Loeseliastrum Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 244000071378 Viburnum opulus Species 0.000 description 1
- 235000019013 Viburnum opulus Nutrition 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000011091 sodium acetates Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
- C09B62/24—Azo dyes
- C09B62/242—Dyes containing in the molecule at least one azo group and at least one other chromophore group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及新的通式(I)纤维反应性甲染料,其中的符号分别在权利要求1中定义,它们的制备,它们在染色或印花含羟基或含氮有机基材方面的应用,以及用这些化合物染色或印花的基材。
Description
活性染料
其中
P和P’独立地是H、C1-4烷基、C1-4烷氧基、-SO3H,
Q和Q’独立地是H或-SO3H,
Me为Cu或Ni,
X和Y独立地是卤原子,
m、n、o、r、s和t独立地是0、1或2,
u是0或1,
v是1或2,条件是u和v之和始终小于3。
在优选的化合物中,X和Y各自为氟,o为0或1,r、s和t各自为0,且m和n均为1或2。
尤其优选的化合物符合通式(II)
其中o为0或1。
通式(I)的化合物及其混合物是活性染料;它们可用于染色或印花含羟基或含氮有机基材,且可用于喷墨印刷油墨中,用于印刷纸张和任选预处理过的基材。
优选的基材包括含有天然或合成聚酰胺,特别是天然或再生的纤维素,例如棉、丝粘胶或短纤维粘胶的皮革和纤维材料。最优选的基材是包含棉的纺织材料。
通式(I)的化合物可根据活性染料常用的任何染色或印花方法,用于染色液或印浆中。优选通过采用30-60℃,优选50-60℃的温度区间的浸染法染色。
本发明的化合物可用作单一染料,或借助它们良好的相容性,作为与具有可比的染色性能,例如总坚牢度、吸尽提浸值(exhaust value)等的相同或其他类的其他活性染料的结合成分。所得的拼色染色与用单一染料染色的坚牢度一致。
通式(I)的化合物提供良好的吸尽提浸值和固色值。未固着的染料部分很容易洗掉。所得的染色和印花表现出良好的耐光性。它们还具有良好的湿牢度性能,例如耐冲洗、耐水、耐海水和耐汗性,并对诸如氯化水、次氯酸盐漂白液、过氧化物漂白液以及含过硼酸盐洗涤剂具有良好的耐氧化性能。
本发明还提供这种新化合物的合成方法。
通式(III)的氨基化合物
与2,4,6-三卤嘧啶反应,形成通式(I)的活性染料。
因此本发明进一步提供通过用以上定义的化合物、它们的盐或其混合物染色或印花,对含羟基或含氮的有机基材染花或印花的方法。
本发明进一步提供用上述染色或印花方法染色或印花后的含羟基的或含氮的有机基材。
本发明还进一步提供已用这种化合物染色或印花的基材,特别是纤维素、聚酰胺和动物纤维,优选是棉。
同样提供了已用含有这种化合物、它们的盐或混合物的喷墨印刷油墨印刷的纸张和任选进行过预处理的含有纤维素、聚酰胺或动物纤维的基材。
以下实施例说明本发明。份为重量份,温度指摄氏度。
实施例1
将通过由重氮化的3-氨基苯甲醛偶合在苯胺ω-甲烷磺酸上制备的32份通式(1a)的偶氮染料
加入250份水中。然后加入23份通式(1b)的化合物。
将这样获得的滤饼在500份水中制浆并加热到50℃,此时经10小时加入14份2,4,6-三氟嘧啶。加入期间用碳酸钠保持pH值为约7。反应结束后进行盐析和过滤。这样提供了含墨绿色盐的粉末形式的60份通式(1e)的化合物,该化合物将棉布染成鲜艳的蓝绿色。
实施例2
重复实施例1的合成,不同的是化合物(1b)用通式(2b)的化合物代替
得到通式(2c)的铜甲
体系
实施例3
重复实施例1的合成,不同的是通式(1a)的单偶氮染料用40份通式(3a)的化合物代替
得到69份通式(3c)的染料
实施例4
以下将说明所述染料的可能用法。
应用方案A
将10份棉织物(已漂白)在40℃下放入300份软化水中含有0.3份实施例1的染料和15份芒硝(煅烧的)的染色浴中。在40℃下放置30分钟后,以0.2、0.6、1.2和最后4份的量每隔10分钟加入共6份的碳酸钠(已煅烧),同时保持温度在40℃。然后在40℃下继续染色1小时。随后在流动的冷水中洗涤染色材料,然后在流动热水中洗涤3分钟。在0.25份马赛皂存在下,在500份软化水中以沸腾状态用15分钟洗净染色。在流水中洗涤(3分钟热水)后,将织物离心甩干,并在烘箱中在约70℃下干燥。这样提供具有良好耐坚牢度,尤其是表现出良好的耐光性和湿牢度并对氧化影响稳定的绿色染色棉。
应用方案B
在300份软化水中含有10份芒硝(已煅烧)的染色浴中放入10份棉材料(已漂白)。在加入0.5份实施例1的染料前,在10分钟内将浴液加热到40℃。在40℃下再放置30分钟后,加入3份碳酸钠(已煅烧),然后在40℃下再继续染色45分钟。
类似方案A,用流动冷水和热水先后洗涤染色材料,并在沸腾状态下洗去染色。洗涤并干燥后留下具有方案A提到的性能的绿色染色棉。
实施例2到4的染料或实施例1到4的染料混合物也可类似方案A和B用于染色。所得染色具有良好的坚牢度性能。
应用方案C
将由以下组成的印浆用常规印花方法印染到棉质材料上。
40份实施例1的染料
100份脲
350份水
500份4%的藻酸钠增稠剂
10份碳酸氢钠
-
共1000份
将印花材料在102-104℃下熏蒸4-8分钟,然后用冷、热水洗涤。随后将固着棉质材料以沸腾状态洗净(类似于方案A)并干燥。所得蓝绿色印刷品表现出良好的总坚牢性。
实施例2到4的染料或实施例1到4的染料混合物也可类似方案C用于印花棉布。在所有情况下都得到具有良好坚牢性的蓝绿色印花品。
使用方案D
将2.5份实施例1的染料搅拌溶解在20份二甘醇与77.5份水在25℃下的混合物中。该溶液可直接用作印刷油墨,用喷墨印刷装置进行印刷。
Claims (7)
2、根据权利要求1的化合物,其符合通式(II)
其中o为0或1。
4、权利要求1的通式(I)的化合物、以及它们的盐或其混合物在染色含羟基或含氮的有机基材中的用途。
5、根据权利要求4的通式(I)的化合物的用途,其用于染色纤维素、聚酰胺和动物纤维。
6、权利要求1的通式(I)的化合物、以及它们的盐或其混合物在喷墨印刷油墨中用于印刷纸张和任选进行过预处理的含有纤维素、聚酰胺或动物纤维的基材的用途。
7、用权利要求1的通式(I)的化合物染色或印花的含有纤维素、聚酰胺或动物纤维的基材。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1423/01 | 2001-07-31 | ||
CH14232001 | 2001-07-31 | ||
CH1423/2001 | 2001-07-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1537148A CN1537148A (zh) | 2004-10-13 |
CN1289610C true CN1289610C (zh) | 2006-12-13 |
Family
ID=4565465
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB028150023A Expired - Fee Related CN1289610C (zh) | 2001-07-31 | 2002-07-29 | 新的甲活性染料 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7015314B2 (zh) |
EP (1) | EP1414911A1 (zh) |
JP (1) | JP2005523341A (zh) |
KR (1) | KR20040019083A (zh) |
CN (1) | CN1289610C (zh) |
BR (1) | BR0211487B1 (zh) |
MX (1) | MXPA04000878A (zh) |
TW (1) | TW593566B (zh) |
WO (1) | WO2003011979A1 (zh) |
ZA (1) | ZA200309214B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100482249C (zh) * | 2004-02-11 | 2009-04-29 | 吴芳 | 肾康注射液在制备治疗肾病综合征的药物中的应用 |
CN100482248C (zh) * | 2004-02-11 | 2009-04-29 | 吴芳 | 肾康注射液在制备治疗糖尿病肾病的药物中的应用 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11441830B2 (en) | 2018-12-26 | 2022-09-13 | Rebound Technologies, Inc. | Solid production systems, devices, and methods utilizing oleophilic surfaces |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CH499604A (de) * | 1966-04-22 | 1970-11-30 | Ciba Geigy Ag | Verfahren zur Herstellung von faserreaktiven schwermetallhaltigen Formazanazofarbstoffen |
DE4125754A1 (de) | 1991-08-03 | 1993-02-04 | Bayer Ag | Fluorpyrimidin-reaktivfarbstoffe |
DE4241918A1 (zh) * | 1991-12-20 | 1993-06-24 | Sandoz Ag | |
CH690649A5 (de) * | 1995-06-07 | 2000-11-30 | Clariant Finance Bvi Ltd | Phthalocyanin-Reaktivfarbstoffe für Fasern. |
-
2002
- 2002-07-29 US US10/484,564 patent/US7015314B2/en not_active Expired - Fee Related
- 2002-07-29 KR KR10-2004-7001374A patent/KR20040019083A/ko not_active Application Discontinuation
- 2002-07-29 MX MXPA04000878A patent/MXPA04000878A/es active IP Right Grant
- 2002-07-29 BR BRPI0211487-9A patent/BR0211487B1/pt not_active IP Right Cessation
- 2002-07-29 CN CNB028150023A patent/CN1289610C/zh not_active Expired - Fee Related
- 2002-07-29 EP EP02749227A patent/EP1414911A1/en not_active Withdrawn
- 2002-07-29 JP JP2003517159A patent/JP2005523341A/ja active Pending
- 2002-07-29 WO PCT/IB2002/002986 patent/WO2003011979A1/en active Application Filing
- 2002-07-29 TW TW091116879A patent/TW593566B/zh not_active IP Right Cessation
-
2003
- 2003-11-26 ZA ZA200309214A patent/ZA200309214B/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100482249C (zh) * | 2004-02-11 | 2009-04-29 | 吴芳 | 肾康注射液在制备治疗肾病综合征的药物中的应用 |
CN100482248C (zh) * | 2004-02-11 | 2009-04-29 | 吴芳 | 肾康注射液在制备治疗糖尿病肾病的药物中的应用 |
Also Published As
Publication number | Publication date |
---|---|
EP1414911A1 (en) | 2004-05-06 |
BR0211487B1 (pt) | 2012-11-27 |
BR0211487A (pt) | 2004-08-17 |
ZA200309214B (en) | 2004-11-26 |
KR20040019083A (ko) | 2004-03-04 |
US20040167321A1 (en) | 2004-08-26 |
WO2003011979A1 (en) | 2003-02-13 |
CN1537148A (zh) | 2004-10-13 |
JP2005523341A (ja) | 2005-08-04 |
TW593566B (en) | 2004-06-21 |
US7015314B2 (en) | 2006-03-21 |
MXPA04000878A (es) | 2004-06-03 |
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