CN1164550A - 颜料 - Google Patents
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- CN1164550A CN1164550A CN97103166A CN97103166A CN1164550A CN 1164550 A CN1164550 A CN 1164550A CN 97103166 A CN97103166 A CN 97103166A CN 97103166 A CN97103166 A CN 97103166A CN 1164550 A CN1164550 A CN 1164550A
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- 239000000049 pigment Substances 0.000 title claims abstract description 48
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- 238000000034 method Methods 0.000 claims description 20
- 238000005859 coupling reaction Methods 0.000 claims description 15
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- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
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- 150000003512 tertiary amines Chemical class 0.000 claims description 2
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- 239000002023 wood Substances 0.000 description 2
- LHECBTWFKAHFAS-UHFFFAOYSA-N 4-(4-aminophenyl)-6,6-dichlorocyclohexa-1,3-dien-1-amine Chemical compound C1C(Cl)(Cl)C(N)=CC=C1C1=CC=C(N)C=C1 LHECBTWFKAHFAS-UHFFFAOYSA-N 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004258 Ethoxyquin Substances 0.000 description 1
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- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
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- 238000007323 disproportionation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- 229940093500 ethoxyquin Drugs 0.000 description 1
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- 239000012362 glacial acetic acid Substances 0.000 description 1
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- HNMCSUXJLGGQFO-UHFFFAOYSA-N hexaaluminum;hexasodium;tetrathietane;hexasilicate Chemical class [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].S1SSS1.S1SSS1.[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] HNMCSUXJLGGQFO-UHFFFAOYSA-N 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000247 postprecipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
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- 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
- C09B9/00—Esters or ester-salts of leuco compounds of vat dyestuffs
-
- 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
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
-
- 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
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
- C09B41/005—Special methods of performing the coupling reaction characterised by the coupling medium containing low molecular weight dispersing agents; containing surface active polythylene gylcols
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- 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
- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
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- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract
本发明提供了一种结晶形式的颜料索引颜料黄12的新型多晶型物，该晶型物的X射线衍射图是具有三处突起的X射线衍射曲线，其相应的“d”间隔是11.82、7.71和3.32×10-10米。
Description
本发明涉及C.L.颜料黄12的一种新型多晶型物。
C.L.颜料黄12是通过偶合四氮化3，3′-二氯联苯胺和N-乙酰乙酰苯胺而得到的二芳基化物黄色颜料。
二芳基化物黄是用于油墨制造的大量黄色颜料的基础，而这些颜料在塑料和油漆中用的较少。在化学等级的普通实践和油墨技术的发展过程中已选择三种类型颜料作为油墨工业上极为重要的物质。它们是染料索引颜料黄12、染料索引颜料黄13和染料索引颜料黄14及其衍生物(通过混合偶合而形成的，例如颜料黄174)。虽然已发现混合偶合在控制颜料性质(通过在颜料颗粒的晶形、大小和形状方面影响分子的堆砌来控制)方面具有某些益处，但与铜酞菁或喹吖啶酮化学相同的技术很少，在铜酞菁或喹吖啶酮化学中存在几种很确定的和不同的同组分多晶型物，这些多晶型物中的一些可以大量制备。
就颜料黄12而论，迄今通过偶合四氮化3，3′-二氯联苯胺和N-乙酰乙酰苯胺制备该物质的方法一般得到这样的晶型，该晶型的特征是在粉末X射线衍射图(如图1、曲线图1所示)中布拉革角为10.33和25.39度。
1987年Yoyo的日本专利申请J62-153353描述了通过碱性盐揉搓形成新型的颜料黄12，并确定了该物质的X射线衍射图。其布拉革角为11.5和25.7度，它们相当于“d”间隔分别为7.69和3.47×10-10米。
令人吃惊的是，我们已经确定了颜料黄12的另一个不同的多晶型物，通过其粉末X射线衍射图，可以很容易地将该多晶型物与“通常”的黄12或TOYO所述的多晶型物区别开。根据制备的详细说明，可以得到基本上纯的新型多晶型物或其与“通常”的黄12多晶型物的混合物。
其实本发明的颜料黄12产物具有布拉革角为7.47、11.45和26.76度的三个主峰，它们相应的“d”间隔为11.82、7.71和3.32×10-10米，通常的颜料黄12多晶型物在布拉革角为10.33和25.39度处具有两个主峰，其相应的“d”间隔为8.55和3.50×10-10米。Toyo所描述的多晶型物具有几个大峰，最大的两个在布拉革角为11.5和25.7度处。
由此，本发明提供了结晶形式的颜料黄12，该晶体的X射线衍射图是具有三处突起的X射线衍射曲线，其相应的“d”间隔是11.82、7.71和3.32×10-10米。
该新物质是具有极好的色强度和其他性质的黄色颜料。作为着色剂使用，通过本领域技术人员已知的方法可以将其进一步改进，从而改善其性质。
本发明也提供了制备本发明颜料黄12多晶型物的方法，该方法是在多胺、多醚、或叔或季胺类型表面活性剂的存在下，偶合四氮化3，3-二氯联苯胺和N-乙酰乙酰苯胺。
多胺表面活性剂的例子可以是式I所表示的化合物，但不限于此，其中R是例如烷基或芳烷基，m＞0，n等于2或3。
R-[NH-(CH)n]mNH2 I
多醚表面活性剂的例子可以是式II所表示的化合物，但不限于此，其中R是例如烷基或芳烷基，m＞0，n等于2或3。
R-[O-(CH)n]mOH II
叔和季胺表面活性剂可以是式III和IV所表示的化合物，但不限于此，其中R、R1、R11、R111相同或不同，它们可以是例如烷基、芳烷基或芳基，X是阴离子类。
RR1R11N III
RR1R11R111N+X- IV
为了得到本发明的新多晶型物，在偶合过程中必须存在表面活性剂。可以在偶合结束之前的任何时刻将其加入，例如可以在用酸沉淀偶合组分时加入，或在偶合组分沉淀后直接加入到浆液中。如果在偶合结束后加入表面活性剂，那么产物就是目前已知的颜料黄12多晶型物。
通过选择所用表面活性剂的类型和相对比例，可以制备出基本上纯净的本发明的颜料黄12。例如当偶合反应在式I的化合物(其中R＝十八烷基，m＝3和n＝3，该化合物相对于反应中所形成的颜料黄12的重量比是15％)存在下进行时，那么产物实质上完全是本发明的多晶型物。另外，选择制备条件，可以得到迄今未知的多晶型物与通常的多晶型物的混合物。可以通过所用表面活性剂的类型和相对比例，来控制这两种多晶型物的相对比例。一般来说，表面活性剂相对偶合组分的比例越高，使得迄今未知的多晶型物在颜料黄12产物中的比例越高。
当得到混合物时，所存在的多晶型物的量至少为颜料黄12总量的10％重量，优选至少为25％重量，更优选至少为50％重量。
为了改善本发明颜料黄12产物作为着色剂的性质，也可以将其进行后处理。后处理的方法对于颜料制造领域的技术人员来说是熟知的。例如在专利号为1，356，253的英国专利中，描述了一些典型的例子。
一种有用的后处理方法是，把偶合结束后得到的含水颜料浆在70-130℃，优选在70-100℃温度范围加热。
更有用的后处理方法是，用有机溶剂处理，例如芳族或脂族烃、氯代烃、醇、酯、醚、腈、硝基化合物或杂环化合物，它们的具体例子是1，2，3，4-四氢化萘、二苄醚、邻二氯苯和癸二酸二丁基酯。
加入阳离子、阴离子、两性或非离子型辅助表面活性剂是也是可以使用的另一种后处理方法。可以使用的阴离子表面活性剂是，例如烷基，芳基、或芳烷基硫酸酯或磺酸酯；烷基、芳基、或芳烷基磷酸酯或膦酸酯、或羧酸。可以使用的阳离子表面活性剂是，例如伯、仲或叔胺、或季胺盐。适用的非离子表面活性剂包括长链醇、醇或胺/环氧乙烷的缩聚物、氧化胺或氧化膦。
可以用脂族伯胺对本发明的颜料黄12进行后处理，该伯胺可以是与偶合反应(为了得到本发明的物质而进行的)过程中所用的胺相同或不同。
此类胺包括例如十八烷基胺、由木松香衍生出来的含氮树脂、N-烷基-亚烷基二胺、多胺例如N-烷基-三丙四胺、四乙五胺或聚乙烯亚胺、或乙氧化二或三胺。
另一个后处理的方法是，用天然或合成树脂树脂化根据本发明的方法所生产的颜料黄。其优选的树脂是可以溶解在碱性溶液中，并且用酸可以将其沉淀在颜料上的树脂。此优选的树脂是例如木松香或化学上被改性的松香，例如通过氢化、岐化、聚合作用、或通过与有机反应物反应使松香改性。在后处理过程中所用树脂的比例可以在宽范围内变化，树脂的量可以是颜料黄12重量的1-60％，更优选25-55％重量。
通过掺入水溶性偶氮染料，可以将本发明的颜料黄12的性质改性，其偶氮染料的量优选为GB1366253中所描述的染料重量的0.1-25％重量范围。
本发明的颜料黄12多晶型物或其与迄今已知的颜料黄12多晶型物的混合物在表面涂料，尤其是印刷油墨的着色，以及塑料的着色中是有用的。
下面通过实施例说明本发明。实施例1-5
通过搅拌把7.5份脂族多胺(见下表)溶于150份水中的11.5份的冰醋酸中。边搅拌边把该溶液缓慢地加入到24.6份N-乙酰乙酰苯胺(它溶解在5.5份氢氧化钠在240份水的溶液中)中。将所得到的混合物与17份预先以常规方式用亚硝酸钠和稀盐酸四氮化的3，3′-二氯联苯胺反应。然后，把偶合的浆液加热到90-95℃，并加入碱将pH值调节到11。把产物过滤、用水洗涤除去可溶盐，然后干燥。
表 1
| 实施例 | 胺 |
| 12345 | N-十八烷基丙二胺N-十八烷基二丙三胺N-十八烷基三丙四胺N-十八烷基四丙五胺N-十八烷基五丙六胺 |
用粉末X射线衍射检验每个实施例中的颜料黄12产物，发现它们实质上是本发明的新多晶型物，如图1中的曲线图2所示。实施例6-8
基本上用实施例1-5中所用的方法制备颜料黄12，但改变反应中所用的胺制品。用粉末X射线衍射方法检验该产物。把本发明颜料黄12多晶型物的纯样品和迄今已知的多晶型物的XRD图比较，可以确定近似的百分组成。
表 2
| 实施例 | 胺 | 胺％* | 本发明的多晶型物％ |
| 678 | N-十八烷基四丙五胺N-十八烷基四丙五胺N-十八烷基四丙五胺 | 1552 | 1007550 |
*胺相对颜料黄12产物的重量比百分数。
Claims (9)
1、一种结晶形式的染料索引颜料黄12，该晶体的X射线衍射图是具有三处突起的X射线衍射曲线，其相应的“d”间隔是11.82、7.71和3.32×10-10米。
2、一种混合物，该混合物含有至少10％权利要求1的颜料黄12与颜料黄12的已知多晶型物。
3、一种混合物，该混合物含有至少25％权利要求1的颜料黄12与颜料黄12的已知多晶型物。
4、一种混合物，该混合物含有至少50％权利要求1的颜料黄12与颜料黄12的已知多晶型物。
5、一种制备权利要求1的颜料黄12的方法，该方法包括在表面活性剂多胺、多醚、或叔胺或季铵化合物的存在下，用N-乙酰乙酰苯胺偶合四氮化3，3′-二氯联苯胺。
6、如权利要求5所述的方法，其中表面活性剂是式I的化合物
R-[NH-(CH)n]mNH2 I其中R是烷基或芳烷基，m＞0，n是2或3。
7、如权利要求5所述的方法，其中表面活性剂是式II化合物
R-[O-(CH)n]mOH II其中R是烷基或芳烷基，m＞0，n是2或3。
8、如权利要求5所要求的方法，其中表面活性剂是式III或IV化合物
RR1R11N III
RR1R11R111N′X- IV
其中R、R1、R11、R111相同或不同，它们每个是烷基、芳烷基或芳基，X-是阴离子。
9、权利要求5-8中任意一项所要求的方法，其中表面活性剂的用量至少是反应中形成的颜料黄12的15％重量。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9603116.6A GB9603116D0 (en) | 1996-02-14 | 1996-02-14 | Pigment |
| GB9603116.6 | 1996-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1164550A true CN1164550A (zh) | 1997-11-12 |
Family
ID=10788750
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97103166A Pending CN1164550A (zh) | 1996-02-14 | 1997-02-13 | 颜料 |
Country Status (13)
| Country | Link |
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| US (1) | US5716445A (zh) |
| EP (1) | EP0790282B1 (zh) |
| JP (1) | JP4109333B2 (zh) |
| KR (1) | KR100433640B1 (zh) |
| CN (1) | CN1164550A (zh) |
| BR (1) | BR9700954A (zh) |
| CA (1) | CA2197389A1 (zh) |
| CZ (1) | CZ294106B6 (zh) |
| DE (1) | DE69715697T2 (zh) |
| DK (1) | DK0790282T3 (zh) |
| ES (1) | ES2181987T3 (zh) |
| GB (1) | GB9603116D0 (zh) |
| ZA (1) | ZA971211B (zh) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105143353B (zh) * | 2013-04-26 | 2017-03-15 | 东洋油墨Sc控股株式会社 | 双偶氮颜料组合物及其制造方法 |
| CN106590016A (zh) * | 2016-12-06 | 2017-04-26 | 杭州荣彩实业有限公司 | 一种混晶型c.i.颜料黄12的生产方法 |
| CN118460011A (zh) * | 2024-07-12 | 2024-08-09 | 辽宁龙宇新材料有限公司 | 一种高透明度c.i.颜料黄12的制备方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5454612B2 (ja) * | 2000-09-21 | 2014-03-26 | Ｄｉｃ株式会社 | 粗製顔料及び粗製顔料分散体 |
| JP5062460B2 (ja) * | 2000-09-21 | 2012-10-31 | Ｄｉｃ株式会社 | 粗製顔料 |
| KR20030048473A (ko) * | 2000-11-17 | 2003-06-19 | 시바 스페셜티 케미칼스 홀딩 인크. | 안료 형광성 증진 방법 |
| DE10223913A1 (de) * | 2002-05-29 | 2003-12-11 | Bayer Cropscience Ag | Verfahren zur Herstellung spezifischer Kristallmodifikationen polymorpher Substanzen |
| US20060188486A1 (en) * | 2003-10-14 | 2006-08-24 | Medivas, Llc | Wound care polymer compositions and methods for use thereof |
| US8034174B2 (en) * | 2008-04-18 | 2011-10-11 | Sun Chemical Corporation | Diarylide yellow pigments |
| WO2022000130A1 (en) * | 2020-06-28 | 2022-01-06 | Dic Corporation | Pigment composition, printing ink, and method for manufacturing pigment composition |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2261626A (en) * | 1939-10-24 | 1941-11-04 | Du Pont | Azo dyes |
| FR1265673A (fr) * | 1960-08-20 | 1961-06-30 | Hoechst Ag | Procédé de préparation de colorants azoïques insolubles dans l'eau et à grand pouvoir tinctorial |
| DE3104257A1 (de) * | 1981-02-07 | 1983-02-03 | Hoechst Ag, 6000 Frankfurt | Azopigmentpraeparationen, verfahren zu ihrer herstellung und ihre verwendung |
| JPS62153353A (ja) * | 1985-12-27 | 1987-07-08 | Toyo Ink Mfg Co Ltd | 新規なジスアゾ化合物結晶多形 |
| US4927466A (en) * | 1989-07-07 | 1990-05-22 | Basf Corp. | Transparent, high strength organic pigments and process for making same |
| US5062894A (en) * | 1991-02-12 | 1991-11-05 | Sun Chemical Corporation | Poly (alkylene oxide)-modified diarylide pigment composition |
| EP0545072A3 (en) * | 1991-11-01 | 1993-08-25 | Hoechst Aktiengesellschaft | New crystalline modification of c.i. pigment yellow 16 |
| EP0567918A3 (en) * | 1992-04-25 | 1993-12-08 | Hoechst Ag | Azopigment preparation |
| US5575843A (en) * | 1994-12-16 | 1996-11-19 | Sun Chemical Corporation | Process for improving color value of a pigment |
-
1996
- 1996-02-14 GB GBGB9603116.6A patent/GB9603116D0/en active Pending
-
1997
- 1997-02-07 ES ES97300805T patent/ES2181987T3/es not_active Expired - Lifetime
- 1997-02-07 DK DK97300805T patent/DK0790282T3/da active
- 1997-02-07 DE DE69715697T patent/DE69715697T2/de not_active Expired - Lifetime
- 1997-02-07 EP EP97300805A patent/EP0790282B1/en not_active Expired - Lifetime
- 1997-02-12 CA CA002197389A patent/CA2197389A1/en not_active Abandoned
- 1997-02-12 CZ CZ1997439A patent/CZ294106B6/cs not_active IP Right Cessation
- 1997-02-13 ZA ZA9701211A patent/ZA971211B/xx unknown
- 1997-02-13 KR KR1019970004219A patent/KR100433640B1/ko not_active Expired - Fee Related
- 1997-02-13 CN CN97103166A patent/CN1164550A/zh active Pending
- 1997-02-13 BR BR9700954A patent/BR9700954A/pt not_active IP Right Cessation
- 1997-02-14 JP JP02948597A patent/JP4109333B2/ja not_active Expired - Fee Related
- 1997-02-14 US US08/799,968 patent/US5716445A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105143353B (zh) * | 2013-04-26 | 2017-03-15 | 东洋油墨Sc控股株式会社 | 双偶氮颜料组合物及其制造方法 |
| CN106590016A (zh) * | 2016-12-06 | 2017-04-26 | 杭州荣彩实业有限公司 | 一种混晶型c.i.颜料黄12的生产方法 |
| CN118460011A (zh) * | 2024-07-12 | 2024-08-09 | 辽宁龙宇新材料有限公司 | 一种高透明度c.i.颜料黄12的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DK0790282T3 (da) | 2003-01-20 |
| JPH09324132A (ja) | 1997-12-16 |
| DE69715697D1 (de) | 2002-10-31 |
| CZ43997A3 (cs) | 1998-05-13 |
| ZA971211B (en) | 1997-08-22 |
| KR100433640B1 (ko) | 2005-06-16 |
| GB9603116D0 (en) | 1996-04-10 |
| JP4109333B2 (ja) | 2008-07-02 |
| CA2197389A1 (en) | 1997-08-15 |
| EP0790282A2 (en) | 1997-08-20 |
| EP0790282A3 (en) | 1998-10-21 |
| EP0790282B1 (en) | 2002-09-25 |
| BR9700954A (pt) | 1998-09-01 |
| US5716445A (en) | 1998-02-10 |
| ES2181987T3 (es) | 2003-03-01 |
| CZ294106B6 (cs) | 2004-10-13 |
| KR970061987A (ko) | 1997-09-12 |
| DE69715697T2 (de) | 2003-08-07 |
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