CN1154382A - 着色的染料组合物 - Google Patents
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Abstract
一种塑料化合物，包括一种高分子材料和有效着色量的一种式其中M是Mg、Ca、Sr、Ba或Mn或其一种或两种的合物、R1和R2是氯或甲基、X是0或1、Y是0或1、并且X和Y之和为1，但须当高分子材料是聚氯乙烯时Y是0的偶氮着色剂。
Description
本发明涉及着色的塑料组合物，新的偶氮着色剂适用于该组合物及其产物。
已发现当将该种偶氮着色剂用于着色的塑料时，具有非常好的高温稳定性。
因此，在一个方面，本发明提供一种塑料组合物，包括一种高分子材料和一种化学式为
的偶氮着色剂，其中M是Mg、Ca、Sr、Ba或Mn或它们中两种或多种的混合物，R1和R2是氯或甲基，X是0或1，Y是0或1，并且X和Y之和为1，但当高分子材料是聚氯乙烯时须Y是0。
在本发明特别优选的组合物中，着色剂是化学式(I)，其中M是Ca、X是1而Y是0，或是其中M是Ca、Y是1和X是0。
R1和R2各自为甲基、X是1和Y是0的式(I)的着色剂被认为是新的。M是Ca、X是0和Y是1的橙色晶型的呈现X射线衍射图象有六条显著的X射线衍射纹，相应的“d”间隔为18.60、5.21、4.20、4.01、3.90和3.66×10-10米的相应的式(I)着色剂也被认为是新的。另外，M是Ca、X是0和Y是1的红色晶型的呈现X射线衍射图象有六条显著的X射线衍射纹，相应的“d”间隔为21.38、13.31、6.60、5.35、4.20和3.35×10-10米的式(I)着色剂也被认为是新的。
式(I)的着色剂可以用镁、钙、锶、钡或锰盐或这些盐中的两种或多种的胺的重氮盐和β-羟基萘酸(BONA)偶合得到的一种重氮染料通过色淀制备，其中，Q是氢、碱金属或铵而X和Y如前所述。
可以用于影响色淀的盐的例子是镁、钙、锶、钡和锰的盐酸盐、硫酸盐、硝酸盐、甲酸盐和乙酸盐及其两种或多种的混合物。这些色淀金属盐可以加入到预制的偶氮染料，即在偶合反应之后，或在偶合之前可以把它们加入到偶合反应混合物里，与β-羟基萘酸偶合成分一起，或更通常地与重氮盐一起加入。
可以用已知的技术进行偶合和色淀反应。在进行偶合反应时，重氮盐的溶液或悬浮液可以加到偶合成分的溶液或悬浮液里，或偶合成分的溶液或悬浮液可以加到重氮盐的溶液或悬浮液里，或重氮盐的溶液或悬浮液与偶合成分的溶液或悬浮液两者可以同时加入到水、水缓冲液或用来实现色淀的金属盐的水溶液里。偶合反应混合物的pH值优选保持在9至12。
在M是Ca、X是0和Y是1的式I着色剂的制备中，当通过把重氮盐的溶液或悬浮液加到偶合成分的溶液或悬浮液中进行偶合反应时，用钙盐色淀生成的染料所得的着色剂是前文所描述的橙色晶型，而当通过把重氮盐的溶液和悬浮液和偶合成分的溶液或悬浮液同时加到水、水缓冲液、或色淀钙盐水溶液中进行偶合反应时，色淀所得的着色剂是前文所描述的红色晶型。
通常用于着色剂的添加剂可以被包括在偶合反应混合物里，或在色淀之前或之后加到偶氮染料里。这种常用的添加剂包括一种或多种促使分散颗粒形成并提高最终产品性能的表面活化剂和一种或多种树脂诸如那些常用于树脂浸润着色剂的树脂以提高着色剂的分散性，这种类型的典型树脂是松香，例如歧化松香。
本发明的着色剂可以当偶合和色淀完成时从反应混合物通过过滤离析出来。过滤的产品可用水洗涤以去除可溶的盐。着色剂可以被干燥和用筛分、球磨、研磨或其它已知方法制成粉。
在优选的实例中，高分子材料是热塑性树脂。它可以是聚烯烃，诸如聚乙烯、聚丙烯或聚异丁烯、聚四氟乙烯，可以是乙烯聚合物，诸如聚氯乙烯或聚乙酸乙烯酯、聚苯乙烯，可以是丙烯酸聚合物，诸如聚甲基丙烯酸甲酯，可以是苯乙烯-丁二烯共聚物、苯乙烯-丙烯腈共聚物、丙烯腈-丁二烯-苯乙烯共聚物，可以是聚酯，诸如聚对苯二甲酸乙二醇酯或聚对苯二甲酸丁二醇酯，可以是聚酰胺、聚酰亚胺、聚碳酸酯、聚苯氧、聚醚-醚酮(PEEK)树脂、聚苯撑硫或聚醚砜。在特别优选的实例中，高分子量材料是聚烯烃，尤其是高密度聚乙烯。
高分子材料的着色可以通过用辊磨机或其它混合或研磨设备将本发明的着色剂一如果要求以母料的形式一混入基质材料里，被着色的材料然后可以由已知的工艺诸如压延、挤出、拉丝、压塑、浇铸或注塑成型制成成型的塑料制品诸如膜、薄片、纤维或其它尤其是三维的成型制品。
着色的高分子材料通常每100重量份着色的材料含有0.001至30重量份、优选0.1至5重量份的着色剂，尽管该量可以根据所要求颜色的深度来变化。
为了获得不同的颜色深浅，除了本发明的着色剂之外，一种或多种填料或其它颜料成分例如白色着色剂、带颜色的着色剂或黑色的着色剂可以加入到高分子材料组合物里。
本发明通过下列实施例详细说明，其中份是重量份。实施例1
向4，6-二氯苯胺-2-磺酸(12.1g)在水中(80ml)的分散体加入47％氢氧化钠水溶液(4.4g)。混合物加热到55℃并搅拌直到获得完全的溶液。通过加冰将溶液冷却到0℃。亚硝酸钠(3.5g)在水中(50ml)的溶液在加入36％盐酸(9.4ml)之后加入。得到的重氮化的淤浆保持温度低于5℃搅拌30分钟。
2-羟基-3-萘甲酸(9.4g)在40℃被溶于水中(200ml)和47％的氢氧化钠(5.3g)水溶液中。通过加冰将溶液冷却到5℃。然后在搅拌下18分钟加入重氮化的淤浆。pH在偶合过程中通过同时加入稀氢氧化钠水溶液保持在10.4-10.6。氯化钙(8.7g)在水中(50ml)的溶液被加入到获得的悬浮液里并持续搅拌40分钟，同时保持温度8-10℃。淤浆然后加热到95℃并保持此温度60分钟。淤浆的pH用稀的氢氧化钠水溶液升高到8.5，在70℃加入Burez 9/18-马来酸改性歧化松香-树脂(2.3g)在水中(80ml)的溶液和47％氢氧化钠水溶液(0.7g)。所得的着色剂淤浆的pH用加入稀的盐酸溶液调节到7.2并通过加冰将溶液温度降到70℃。然后过滤淤浆，用水洗涤所得的滤饼，在70℃干燥，在90℃焙烧。所得的干燥团块被研磨以得到粉末着色剂组合物。实施例2
向2-氨基-4-(三氟甲基)苯磺酸(12.1g)在水中(80ml)的分散体加入47％氢氧化钠水溶液(4.4g)。混合物加热到55℃并搅拌直到获得完全的溶液。通过加冰将溶液冷却到0℃。亚硝酸钠(3.5g)在水中(50ml)的溶液在加入36％盐酸(9.4ml)之后加入。得到的重氮化的淤浆保持温度低于5℃搅拌30分钟。2-羟基-3-萘甲酸(9.6g)在40℃被溶于水中(200ml)和47％的氢氧化钠(5.3g)水溶液中。通过加冰将溶液冷却到5℃。然后在搅拌下16分钟加入重氮化的淤浆。pH在偶合过程中通过同时加入稀氢氧化钠水溶液保持在10.4-10.6。氯化钙(8.7g)在水中(50ml)的溶液被加入到获得的悬浮液里并持续搅拌25分钟，同时保持温度8-10℃。淤浆然后加热到95℃并保持此温度60分钟。淤浆的pH用稀的氢氧化钠水溶液升高到8.5，在70℃加入Burez 9/18(2.2g)在水中(80ml)的溶液和47％氢氧化钠水溶液(0.7g)。所得的着色剂淤浆的pH用加入稀盐酸溶液调节到7.2并通过加冰将溶液温度降低到70℃。然后过滤淤浆，用水洗涤所得的滤饼，在70℃干燥，在90℃焙烧。所得的干燥团块被研磨以得到粉末着色剂组合物。
生成的橙色树脂浸透的着色剂的粉末X射线衍射图象和没有松脂的用类似方法制备的橙色着色剂的粉末X射线衍射图象有六条显著的与18.60、5.21、4.20、4.01、3.90、和3.66×10-10米的“d”间隔对应的X射线衍射线。实施例3
高密度聚乙烯(100份)与实施例1的着色剂(0.132份)和二氧化钛(1份)混合。在双辊磨上研磨混合物，然后注塑。在发生颜色改变之前，与标准样品在200℃加热12秒相比，所得样品在260℃保持5分钟仍稳定。实施例4
重复实施例3，用实施例2的着色剂(0.5份)代替实施例1的着色剂。在发生颜色改变之前，与标准样品在200℃加热12秒相比，所得样品在260℃保持5分钟仍稳定。实施例5
向4，6-二甲基苯胺-2-磺酸(10.0g)在水中(150ml)的分散体加入47％氢氧化钠水溶液(5.1g)。混合物加热到55℃并搅拌直到获得完全的溶液。通过加冰将溶液冷却到0℃。亚硝酸钠(3.5g)在水中(25ml)的溶液在加入36％盐酸(9.7ml)之后加入。得到的重氮化的淤浆保持温度低于5℃搅拌70分钟。在偶合之前，加入固体氯化钙(8.5g)。
2-羟基-3-萘甲酸(9.6g)在40℃被溶于水中(200ml)和47％的氢氧化钠(5.1g)水溶液中 在该溶液中加入Portuguese WW松脂-一种松香性树脂(4.2g)、水(60ml)和47％的氢氧化钠水溶液(1.4g)。通过加冰将所得溶液冷却到6℃。然后在搅拌下60分钟加入重氮化的淤浆。pH在偶合过程中通过同时加入稀氢氧化钠水溶液保持在10.4-10.6。持续搅拌60分钟。淤浆然后加热到90℃并将淤浆的pH用稀的盐酸调到7.2。通过加冰将淤浆温度降低到70℃。然后过滤淤浆，用水洗涤所得的滤饼，并在70℃干燥，在90℃焙烧。所得的干燥团块被研磨以得到粉末着色剂组合物。实施例6
重复实施例3，用实施例5的着色剂(0.1份)代替实施例1的着色剂。在发生颜色改变之前，与标准样品在200℃加热12秒相比，所得样品在280℃保持5分钟仍稳定。实施例7
向2-氨基-4-(三氟甲基)苯磺酸(24.1g)在水中(250ml)的分散体加入47％氢氧化钠水溶液(10.0g)。混合物加热到45℃并搅拌直到获得完全的溶液。然后加入36％的盐酸(22.9g)。通过加冰将溶液冷却到0℃并加入亚硝酸钠(6.9g)在水中(25ml)的溶液。得到的重氮化的淤浆保持温度低于5℃搅拌30分钟。就在偶合之前，加入氯化钙(18.4g)在水中(100ml)的溶液。2-羟基-3-萘甲酸(18.8g)在35℃被溶于水中(250ml)和47％的氢氧化钠水溶液中(10.0g)。在该溶液中加入Portuguese松脂--一种松香性树脂(4.3g)、水(60ml)和47％的氢氧化钠水溶液(1.4g)。通过加冰将所得溶液冷却到5℃。然后在搅拌下(55分钟)把重氮化的淤浆和2-羟基-3-萘甲酸/树脂溶液在5℃同时加入到有水(100ml)的容器里。pH在偶合时通过同时加入稀释的氢氧化钠水溶液保持在10.4-10.6。通过定期加入冰将温度保持在低于5℃。持续搅拌30分钟。淤浆然后加热到90℃将将淤浆的pH用稀释的盐酸调到7.2。通过加冰将溶液温度降低到70℃。然后过滤淤浆，用水洗涤所得的滤饼，在70℃干燥，在90℃焙烧。所得的干燥团块被研磨以得到粉末着色剂组合物。
生成的红色树脂浸润的着色剂的粉末X射线衍射图象和没有树脂的用类似方法制备的红色着色剂的粉末X射线衍射图象有六条显著的与21.38、13.31、6.60、5.35、4.20和3.35×10-10米的“d”间隔对应的X射线衍射线。实施例8
重复实施例3，用实施例7的着色剂(0.1份)代替实施例1的着色剂。在发生颜色改变之前，与标准样品在200℃加热12秒相比，所得样品在280℃保持5分钟仍稳定。
Claims (15)
1.一种塑料组合物，包括一种高分子材料和有效着色剂量的一种式的偶氮着色剂，其中M是Mg、Ca、Sr、Ba或Mn或它们中两种或多种的混合物，R1和R2是氯或甲基，X是0或1，Y是0或1，并且X和Y之和为1，但当高分子材料是聚氯乙烯时须Y是0。
2.按权利要求1所述的组合物，其中M是Ca、X是1，Y是0。
3.按权利要求1所述的组合物，其中M是Ca、Y是1，X是0。
4.按权利要求1、2或3中所述的组合物，其中着色剂是树脂浸润型的。
5.按权利要求1-4中任一项所述的组合物，其中高分子材料是一种热塑树脂。
6.按权利要求5所述的组合物，其中热塑树脂是聚烯烃。
7.按权利要求6所述的组合物，其中热塑树脂是高密度聚乙烯。
8.如权利要求1所规定的式(I)的偶氮着色剂，R1和R2分别是甲基，X是1，Y是0。
9.如权利要求1所规定的式(I)的偶氮着色剂，M是Ca，X是0，Y是1，它呈现X射线衍射图象有六条显著的与18.60、5.21、4.20、4.01、3.90和3.66×10-10米的“d”间隔对应的X射线衍射纹的晶型。
10.如权利要求1所规定的式(I)的偶氮着色剂，M是Ca、X是0，Y是1，呈现X射线衍射图象有六条显著的与21.38、13.31、6.60、5.35、4.20和3.35×10-10的“d”间隔对应的X射线衍射纹的晶型。
11.按权利要求8、9或10的所述的着色剂，是树脂浸润型的。
12.用于制备按权利要求8所述的着色剂的方法，包括用镁、钙、锶、钡或锰盐或其两种或多种的混合物，与下式的胺的一种重氮盐与β-羟基萘酸偶合所得的一种重氮染料进行色淀，其中Q是氢、碱金属或铵，R1和R2分别是甲基，X是1而Y是0。
13.按权利要求12所述的方法，其中盐是镁、钙、锶、钡或锰的盐酸盐、硫酸盐、硝酸盐、甲酸盐或乙酸盐或其两种或多种的混合物。
14.按权利要求9所述的制备着色剂的方法，其包括把下式的一种胺的一种重氮盐与β-羟基萘酸以下述方式偶合：把该重氮盐的一种溶液或悬浮液加入到偶合成分的溶液或悬浮液中，并用一种钙盐色淀生成的染料，这里，Q是氢、一种碱金属或铵，R1和R2分别是甲基，X是0，Y是1。
15.按权利要求10所述的制备着色剂的方法，其包括把下式
的胺的一种重氮盐与β-羟基萘酸以下述方式偶合：把该重氮盐的一种溶液或悬浮液和偶合成分的一种溶液或悬浮液同时加入到水中、一种水缓冲溶液中或一种色淀钙盐的水溶液中，并且，这里该重氮盐溶液或悬浮液与偶合剂溶液或悬浮液是同时加入到水中或一种水缓冲液中，并用一种钙盐色淀生成的染料，这里，Q是氢、一种碱金属或铵，R1和R2分别是甲基，X是0而Y是1。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9520493.9A GB9520493D0 (en) | 1995-10-07 | 1995-10-07 | Pigments |
| GB9520493.9 | 1995-10-07 |
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| Publication Number | Publication Date |
|---|---|
| CN1154382A true CN1154382A (zh) | 1997-07-16 |
| CN1070887C CN1070887C (zh) | 2001-09-12 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN96121171A Expired - Fee Related CN1070887C (zh) | 1995-10-07 | 1996-10-05 | 着色的染料组合物 |
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| US (1) | US5837761A (zh) |
| EP (1) | EP0767219B1 (zh) |
| JP (1) | JPH09132674A (zh) |
| KR (1) | KR100420904B1 (zh) |
| CN (1) | CN1070887C (zh) |
| AT (1) | ATE198343T1 (zh) |
| AU (1) | AU714649B2 (zh) |
| BR (1) | BR9605003A (zh) |
| CA (1) | CA2187147C (zh) |
| CZ (1) | CZ291973B6 (zh) |
| DE (1) | DE69611338T2 (zh) |
| DK (1) | DK0767219T3 (zh) |
| ES (1) | ES2153540T3 (zh) |
| GB (1) | GB9520493D0 (zh) |
| IL (1) | IL119369A (zh) |
| NO (1) | NO310924B1 (zh) |
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| PL (1) | PL316378A1 (zh) |
| PT (1) | PT767219E (zh) |
| RU (1) | RU2181734C2 (zh) |
| SG (1) | SG49979A1 (zh) |
| ZA (1) | ZA968368B (zh) |
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| KR100359469B1 (ko) * | 2000-02-18 | 2002-11-07 | 주식회사 폴리코 | 폴리올레핀 부직포의 날염처리방법 |
| ATE301166T1 (de) | 2000-09-21 | 2005-08-15 | Ciba Sc Holding Ag | Tinte enthaltend eine orange azolackpigmentzusammensetzung |
| KR100590853B1 (ko) * | 2004-03-12 | 2006-06-19 | 오리엔트 가가쿠 고교 가부시키가이샤 | 레이저광 투과성 조성물 및 레이저 용착 방법 |
| US20080127497A1 (en) * | 2005-10-31 | 2008-06-05 | Dennis Moss | Blade assembly |
| US8631583B2 (en) | 2005-10-31 | 2014-01-21 | Dennis Moss | Bagel slicer |
| RU2524386C1 (ru) * | 2013-02-14 | 2014-07-27 | Закрытое акционерное общество "Комплекс про" | Способ получения экструзионной окрашенной поливинилхлоридной композиции и экструзионная окрашенная поливинилхлоридная композиция строительного назначения |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2225665A (en) * | 1939-09-20 | 1940-12-24 | Du Pont | Azo pigment and coating composition containing the same |
| US2694055A (en) * | 1951-12-10 | 1954-11-09 | Sherwin Williams Co | Metallic azo pigments |
| US2821525A (en) * | 1953-04-07 | 1958-01-28 | American Cyanamid Co | Azo coloring matters |
| CH601389A5 (zh) * | 1975-07-04 | 1978-07-14 | Ciba Geigy Ag | |
| US4115377A (en) * | 1977-01-31 | 1978-09-19 | Hercules Incorporated | Rubine mixed strontium-cadmium salts of 3-chloro-4-methyl-6-sulfophenylazo-hydroxynaphthoic acid |
| DE2834028C2 (de) * | 1978-08-03 | 1987-04-02 | Basf Ag, 6700 Ludwigshafen | Deckende Calziumfarblacke mit hoher Purtonbrillanz und verbesserter Lichtechtheit, Verfahren zu deren Herstellung und deren Verwendung |
| DE3223888A1 (de) * | 1982-06-26 | 1983-12-29 | Hoechst Ag, 6230 Frankfurt | Neue kristallmodifikation von pigment red 53:1 |
-
1995
- 1995-10-07 GB GBGB9520493.9A patent/GB9520493D0/en active Pending
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1996
- 1996-09-26 PT PT96307025T patent/PT767219E/pt unknown
- 1996-09-26 DK DK96307025T patent/DK0767219T3/da active
- 1996-09-26 DE DE69611338T patent/DE69611338T2/de not_active Expired - Fee Related
- 1996-09-26 AT AT96307025T patent/ATE198343T1/de not_active IP Right Cessation
- 1996-09-26 EP EP96307025A patent/EP0767219B1/en not_active Expired - Lifetime
- 1996-09-26 ES ES96307025T patent/ES2153540T3/es not_active Expired - Lifetime
- 1996-09-30 AU AU67941/96A patent/AU714649B2/en not_active Ceased
- 1996-09-30 US US08/723,729 patent/US5837761A/en not_active Expired - Lifetime
- 1996-10-01 SG SG1996010776A patent/SG49979A1/en unknown
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- 1996-10-03 PL PL96316378A patent/PL316378A1/xx unknown
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- 1996-10-04 RU RU96119937/04A patent/RU2181734C2/ru not_active IP Right Cessation
- 1996-10-04 CZ CZ19962914A patent/CZ291973B6/cs not_active IP Right Cessation
- 1996-10-04 NO NO19964207A patent/NO310924B1/no not_active IP Right Cessation
- 1996-10-04 CA CA002187147A patent/CA2187147C/en not_active Expired - Fee Related
- 1996-10-04 BR BR9605003A patent/BR9605003A/pt not_active IP Right Cessation
- 1996-10-05 CN CN96121171A patent/CN1070887C/zh not_active Expired - Fee Related
- 1996-10-05 KR KR1019960044104A patent/KR100420904B1/ko not_active IP Right Cessation
- 1996-10-07 JP JP8264976A patent/JPH09132674A/ja not_active Withdrawn
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Also Published As
| Publication number | Publication date |
|---|---|
| US5837761A (en) | 1998-11-17 |
| EP0767219B1 (en) | 2000-12-27 |
| DE69611338D1 (de) | 2001-02-01 |
| DK0767219T3 (da) | 2001-01-29 |
| DE69611338T2 (de) | 2001-07-19 |
| AU714649B2 (en) | 2000-01-06 |
| KR100420904B1 (ko) | 2005-06-16 |
| ES2153540T3 (es) | 2001-03-01 |
| NZ299501A (en) | 1996-11-26 |
| ATE198343T1 (de) | 2001-01-15 |
| PL316378A1 (en) | 1997-04-14 |
| KR970021215A (ko) | 1997-05-28 |
| CN1070887C (zh) | 2001-09-12 |
| RU2181734C2 (ru) | 2002-04-27 |
| NO964207L (no) | 1997-04-08 |
| JPH09132674A (ja) | 1997-05-20 |
| CA2187147C (en) | 2005-08-16 |
| EP0767219A2 (en) | 1997-04-09 |
| SG49979A1 (en) | 2000-07-18 |
| ZA968368B (en) | 1997-04-07 |
| NO310924B1 (no) | 2001-09-17 |
| IL119369A0 (en) | 1997-01-10 |
| CA2187147A1 (en) | 1997-04-08 |
| GB9520493D0 (en) | 1995-12-13 |
| NO964207D0 (no) | 1996-10-04 |
| CZ291496A3 (en) | 1997-04-16 |
| BR9605003A (pt) | 1998-06-23 |
| CZ291973B6 (cs) | 2003-06-18 |
| EP0767219A3 (en) | 1998-05-06 |
| IL119369A (en) | 2003-02-12 |
| PT767219E (pt) | 2001-05-31 |
| MX9604645A (es) | 1997-09-30 |
| AU6794196A (en) | 1997-04-10 |
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