CN1129008A - 粒状靛白制备物 - Google Patents
粒状靛白制备物 Download PDFInfo
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- CN1129008A CN1129008A CN94193075A CN94193075A CN1129008A CN 1129008 A CN1129008 A CN 1129008A CN 94193075 A CN94193075 A CN 94193075A CN 94193075 A CN94193075 A CN 94193075A CN 1129008 A CN1129008 A CN 1129008A
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- CMSRLFLXFXUENW-UHFFFAOYSA-L disodium;2-(3-oxido-1h-indol-2-yl)-1h-indol-3-olate Chemical compound [Na+].[Na+].N1C2=CC=CC=C2C([O-])=C1C1=C([O-])C2=CC=CC=C2N1 CMSRLFLXFXUENW-UHFFFAOYSA-L 0.000 title abstract description 4
- 238000004043 dyeing Methods 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 7
- 229920002678 cellulose Polymers 0.000 claims abstract description 6
- 239000001913 cellulose Substances 0.000 claims abstract description 6
- 239000004753 textile Substances 0.000 claims abstract description 6
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims description 46
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 43
- 229940097275 indigo Drugs 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 10
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 2
- 238000001694 spray drying Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002351 wastewater Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- COHYTHOBJLSHDF-BUHFOSPRSA-N indigo dye Chemical compound N\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-BUHFOSPRSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 235000013379 molasses Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 thiourea peroxide Chemical class 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 238000003809 water extraction Methods 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0077—Preparations with possibly reduced vat, sulfur or indigo dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
Abstract
本发明涉及含有作为主要成分的靛白和碱金属氢氧化物的粒状靛白制备物，以及此类制备物的生产及其在含纤维素纺织材料的染色方面的应用。
Description
本发明涉及基本上由靛蓝隐色体和碱金属氢氧化物组成的新颖、粒状靛蓝隐色体制备物。
本发明还涉及这类靛蓝隐色体制备物的生产及其在含纤维素纺织材料的染色方面的应用。
靛蓝是一种众所周知的还原染料，用于含纤维素的纺织材料的染色，尤其是用在蓝牛仔布制品用棉经纱的染色。
为了进行染色，首先必须借还原把不溶于水的靛蓝转化成水溶性靛蓝隐色体形式，该形式被待染材料吸收之后，再给氧化变回其有色形式。
在传统的染色过程中，靛蓝是通过向染浴上游的容器中的碱性介质内加入象连二亚硫酸钠和二氧化硫脲等无机还原剂，或者象羟基丙酮之类的有机还原剂而被还原的。染色过程中，由于在空气通道内染浴液面处一定量的靛蓝隐色体与空气接触被氧化，且必须将其再还原，故消耗了其数量与机器形式有关的额外部分的还原剂，这也是为什么还要在染浴内加入少量还原剂的原因。
采用上述还原剂还原靛蓝的一个缺点是染厂废水中，当使用连二亚硫酸钠时，硫酸盐含量高(约3,500-5,000mg/l，按靛蓝染厂排出废水测定)，或者当使用羟基丙酮时，耗氧物含量高(COD约为8,000mg/l，按靛蓝染厂排出废水测定)。另外，还原过程，譬如用连二亚硫酸钠时，需要加入大量的碱。
另外，也已知道可把粉状固体制成含有作为稳定剂的多羟基化合物的糊状靛蓝隐色体制备物，例如含甘油，且尤其是由糖衍生而来的化合物，象糖蜜，混之以碱或锌粉(DE 200 914或235047)。若把这类制备物用于染色，染厂废水的硫酸盐含量的确能有效地降低，但是，结果废水中溶解的有机羟基化合物的含量则很高(用TOC(总有机碳)、COD(化学耗氧量)或BOD(生物耗氧量)来度量)；举例说，含25％(重量)糖蜜的60％(重量)靛蓝隐色体制备物能产生约8,000mg/l的COD。
最后，早些时候的德国专利申请P 43 10 122.4描述了一种染色方法，其中靛蓝是以预还原的形式，即在催化氢化中获得的含水、碱性溶液形式使用的。这样便消除了废水中的有机物质的含量，同时也将硫酸盐的浓度值降低到染色过程中因与空气接触而要求的亚硫酸氢盐的数量。然而，缺点是使用的靛蓝隐色体溶液是氧化敏感的，因而必须在严格排除氧的条件下操作。
本发明的一个目的在于提供一种靛蓝隐色体制备物，它不具有上述缺点而且是有利于染色的。
我们发现，这一目的为基本上由靛蓝隐色体和碱金属氢氧化物组成的粒状靛蓝隐色体制备物所达到。
我们还发现制备此类靛蓝隐色体制备物的方法，包括把靛蓝隐色体的碱性水溶液在充分混合及排除氧的条件下浓缩至干的步骤。
最后，本发明提供此种靛蓝隐色体材备物在含纤维素纺织材料的染色中的应用。
本发明的靛蓝隐色体制备物包含基本成分靛蓝隐色体和碱金属氢氧化物，其摩尔比通常在1∶1-1∶10，较好在1∶1-1∶2之间。
因而，依碱金属氢氧化物的含量不同，靛蓝隐色体以一或二碱金属盐的形式存在。
合适的碱金属氢氧化物的例子具体包括氢氧化钾，而尤其是氢氧化钠。
本发明的靛蓝隐色体制备物的本质性特征是其粒状形式。其颗粒一般绝大多数为球形颗粒，其平均粒径一般在0.1-2mm，较好在0.5-1.5mm之间。
令人惊奇的是，这些颗粒即使在没有稳定剂的条件下也是对氧化稳定的。它们易于维护而且甚至可以短时间露天存放。然而对于长期存放，建议还是采用密封容器。
本发明的靛蓝隐色体制备物生产中尤其具有优越性的是，从催化氢化生产靛蓝隐色体的过程当中得到的水溶液可以在澄清之后(尤其是除掉催化剂之后)，直接用于干燥。
正如普遍已知的，催化氢化本身可以通过，例如以兰尼镍为催化剂、氢压一般在2-4bar以及温度一般在60-90℃之间的条件下将碱性靛蓝糊料(通常靛蓝占10-35％(重量)、氢氧化钠占2-10％(重量)还原来完成。
所得靛蓝隐色体溶液一般地含有靛蓝隐色体10-35，较好15-30，尤其好20-25％(重量)。
在本发明的生产过程中，将靛蓝隐色体溶液在排除氧的条件下浓缩至干，有利地预先用象氮这类保护性气体惰性化，并且充分混合。
干燥所要求的产物温度依是否采用减压而定，而通常介于50-80℃或者70-120℃之间。
干燥过程中，必须保证溶液和固体物料的充分混合。
因此，适合工业应用的设备包括，例如转鼓干燥器、浆式干燥器和强制清洁接触干燥器，其中，干燥较好在减压(约50-500mbar)下进行。必要的话，可以在干燥设备内部或外部进行进一步的粗粉碎。
本发明的过程还可以有利地在喷雾干燥设备中进行，象喷雾塔，且尤其是喷雾流化床，其中水在不断受到热惰性气体，较好氮气的冲击下蒸发。在其内，可以直接获得符合要求粒径的干燥产物。
建议在干燥产物出料之前，先将其冷却到，通常介于20-40℃，以便避免热状态下的再氧化过程。
本发明的方法能提供连续生产粒状形式的靛蓝隐色体制备物的简单方法。通常，干燥产物中未还原靛蓝含量还不足8％(重量)。
本发明的靛蓝隐色体制备物有利地适合于含纤维素的纺织材料的染色。所得到的染色完全符合要求。废水中的硫酸盐含量及染色过程中碱金属氢氧化物的消耗均大大降低；只需要把染色过程中因与空气接触而被氧化的靛蓝隐色体重新还原。
实例
按照本发明的靛蓝隐色体制备物的生产。
实例1
把由20％(重量)靛蓝隐色体、5％(重量)氢氧化钠和75％(重量)的水组成的溶液在30mbar下逐渐地送过氮气-惰性化的，加热到130℃的油浴温度的旋转蒸发器中，并在55rpm的转速之下浓缩至干。随后令其冷却到40℃。经粗粉碎后，该粒料具有1mm的平均粒径。在索格利特萃取器中用水萃取的结果揭示，其水不溶物含量(副产物及未还原靛蓝)为4.4％(重量)
实例2
把含有20％(重量)靛蓝隐色体、5％(重量)氢氧化钠和75％(重量)的水的溶液加入到一只流化气体速度1.2m/秒-1的氮气惰性化的流化床中连续喷雾造粒。进气温度为130℃，而出气温度为90℃，而且该温度也对应于流化床内部的物料温度。生成的粒料被经过一个螺旋出料器排出流化床然后填入一只氮清洗的容器内，使其冷却至室温。
有用级分的粒料具有约1mm的平均粒径。其水不溶物含量为5％(重量)以下。
Claims (6)
1.一种基本上由靛蓝隐色体和碱金属氢氧化物组成的颗粒形式的靛蓝隐色体制备物。
2.如权利要求1要求的靛蓝隐色体制备物，其中靛蓝隐色体与碱金属氢氧化物的摩尔比介于1∶1-1∶10之间。
3.一种制备权利要求1或2的靛蓝隐色体制备物的方法，包括把靛蓝隐色体的碱性水溶液在充分混合及排除氧的条件下浓缩至干。
4.如权利要求3要求的方法，它是在惰性气氛中和/或减压的条件下进行的。
5.如权利要求3或4要求的方法，它是在喷雾干燥设备中进行的。
6.权利要求1或2的靛蓝隐色体制备物在含纤维素纺织材料的染色方面的应用。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4327221A DE4327221A1 (de) | 1993-08-13 | 1993-08-13 | Leukoindigo-Präparation in Granulatform |
| DEP4327221.5 | 1993-08-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1129008A true CN1129008A (zh) | 1996-08-14 |
| CN1043653C CN1043653C (zh) | 1999-06-16 |
Family
ID=6495112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94193075A Expired - Fee Related CN1043653C (zh) | 1993-08-13 | 1994-08-09 | 粒状靛蓝隐色体制备物及其在染色方面的应用 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5637116A (zh) |
| EP (1) | EP0712430B1 (zh) |
| JP (1) | JP3694316B2 (zh) |
| CN (1) | CN1043653C (zh) |
| AU (1) | AU679782B2 (zh) |
| BR (1) | BR9407245A (zh) |
| CA (1) | CA2169264A1 (zh) |
| CZ (1) | CZ34396A3 (zh) |
| DE (2) | DE4327221A1 (zh) |
| ES (1) | ES2123822T3 (zh) |
| PL (1) | PL312984A1 (zh) |
| TW (1) | TW272226B (zh) |
| WO (1) | WO1995005421A1 (zh) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516817A (zh) * | 2011-12-28 | 2012-06-27 | 河北化工医药职业技术学院 | 靛白溶液的环保制备方法 |
| CN102046875B (zh) * | 2008-06-09 | 2012-10-17 | 德司达染料德国有限责任公司 | 用靛白泡沫对经纱染色的方法 |
| CN110016816A (zh) * | 2019-03-13 | 2019-07-16 | 广东前进牛仔布有限公司 | 一种靛蓝染色方法 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19502968A1 (de) * | 1995-01-31 | 1996-08-01 | Basf Ag | Leukoküpenfarbstoff-Präparationen in Granulatform |
| DE19624208A1 (de) * | 1996-06-18 | 1998-01-02 | Basf Ag | Leukoküpenfarbstoff-Präparationen in Granulatform |
| DE19831291A1 (de) * | 1998-07-13 | 2000-01-20 | Basf Ag | Konzentrierte Lekoindigolösungen |
| TWI755558B (zh) * | 2017-08-11 | 2022-02-21 | 瑞士商亞齊羅馬Ｉｐ公司 | 製作極低苯胺含量之靛白溶液的方法、及對應之穩定的水性靛白溶液及製備靛藍的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE245623C (zh) * | ||||
| DE200914C (zh) * | ||||
| FR360447A (fr) * | 1905-10-07 | 1906-04-21 | Basf Ag | Production de sels alcalins de l'indigo blanc secs et stables |
| US833654A (en) * | 1906-04-17 | 1906-10-16 | Basf Ag | Alkali salt of indigo white and process of making same. |
| DE235047C (zh) * | 1908-10-14 | |||
| GB190924605A (en) * | 1909-10-26 | 1910-08-25 | Columbia Postal Supply Co | Improvements in Mail Marking Machines. |
| FR417071A (fr) * | 1909-11-10 | 1910-11-05 | Basf Ag | Préparations solides et stables à base d'indigo blanc |
| DE431122C (de) * | 1924-05-22 | 1926-06-29 | Waermespeicher Dr Ruths Ges M | Sicherung fuer mit Speichern versehene Kraftanlagen, insbesondere Dampfturbinen |
| US2088213A (en) * | 1935-03-13 | 1937-07-27 | Nat Aniline & Chem Co Inc | Process for the drying of materials |
| US2159930A (en) * | 1935-08-07 | 1939-05-23 | Dow Chemical Co | Preparation of leuco-indigo |
| EP0274216B1 (en) * | 1986-12-02 | 1995-03-01 | Canon Kabushiki Kaisha | Ink and ink-jet recording process employing the same |
| US4992078A (en) * | 1989-02-23 | 1991-02-12 | Sandoz Ltd. | Sulfur dyes and method of preparing same: membrane process |
| CA2091630A1 (en) * | 1993-03-15 | 1994-09-16 | Todd Gray | Stick for playing a game |
-
1993
- 1993-08-13 DE DE4327221A patent/DE4327221A1/de not_active Withdrawn
-
1994
- 1994-07-27 TW TW083106843A patent/TW272226B/zh not_active IP Right Cessation
- 1994-08-09 WO PCT/EP1994/002637 patent/WO1995005421A1/de active IP Right Grant
- 1994-08-09 ES ES94926168T patent/ES2123822T3/es not_active Expired - Lifetime
- 1994-08-09 JP JP50672895A patent/JP3694316B2/ja not_active Expired - Lifetime
- 1994-08-09 EP EP94926168A patent/EP0712430B1/de not_active Expired - Lifetime
- 1994-08-09 DE DE59407311T patent/DE59407311D1/de not_active Expired - Lifetime
- 1994-08-09 CZ CZ96343A patent/CZ34396A3/cs unknown
- 1994-08-09 PL PL94312984A patent/PL312984A1/xx unknown
- 1994-08-09 CN CN94193075A patent/CN1043653C/zh not_active Expired - Fee Related
- 1994-08-09 BR BR9407245A patent/BR9407245A/pt not_active IP Right Cessation
- 1994-08-09 AU AU76119/94A patent/AU679782B2/en not_active Ceased
- 1994-08-09 CA CA002169264A patent/CA2169264A1/en not_active Abandoned
- 1994-08-09 US US08/592,308 patent/US5637116A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102046875B (zh) * | 2008-06-09 | 2012-10-17 | 德司达染料德国有限责任公司 | 用靛白泡沫对经纱染色的方法 |
| CN102516817A (zh) * | 2011-12-28 | 2012-06-27 | 河北化工医药职业技术学院 | 靛白溶液的环保制备方法 |
| CN102516817B (zh) * | 2011-12-28 | 2013-12-11 | 河北化工医药职业技术学院 | 靛白溶液的环保制备方法 |
| CN110016816A (zh) * | 2019-03-13 | 2019-07-16 | 广东前进牛仔布有限公司 | 一种靛蓝染色方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1995005421A1 (de) | 1995-02-23 |
| AU7611994A (en) | 1995-03-14 |
| CZ34396A3 (en) | 1996-05-15 |
| JPH09504311A (ja) | 1997-04-28 |
| DE59407311D1 (de) | 1998-12-24 |
| US5637116A (en) | 1997-06-10 |
| TW272226B (zh) | 1996-03-11 |
| CA2169264A1 (en) | 1995-02-23 |
| BR9407245A (pt) | 1996-09-24 |
| EP0712430B1 (de) | 1998-11-18 |
| ES2123822T3 (es) | 1999-01-16 |
| AU679782B2 (en) | 1997-07-10 |
| JP3694316B2 (ja) | 2005-09-14 |
| PL312984A1 (en) | 1996-05-27 |
| EP0712430A1 (de) | 1996-05-22 |
| CN1043653C (zh) | 1999-06-16 |
| DE4327221A1 (de) | 1995-02-16 |
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