CN1179789A - 单偶氮颜料 - Google Patents

单偶氮颜料 Download PDF

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CN1179789A
CN1179789A CN95197386A CN95197386A CN1179789A CN 1179789 A CN1179789 A CN 1179789A CN 95197386 A CN95197386 A CN 95197386A CN 95197386 A CN95197386 A CN 95197386A CN 1179789 A CN1179789 A CN 1179789A
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salt
compound
azo
methyl isophthalic
following formula
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CN1085234C (zh
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A·P·乔顿
J·梅森
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Lubrizol Corp
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Zeneca Ltd
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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
    • C09B63/00—Lakes
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
    • C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
    • 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
    • C09B63/00—Lakes
    • C09B63/005—Metal lakes of dyes
    • 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
    • C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds
    • 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
    • Y10S534/00—Organic compounds -- part of the class 532-570 series
    • Y10S534/04—Azo compounds which are lakes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Coloring (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Paints Or Removers (AREA)
  • Cosmetics (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

一种式(Ⅰ)的以盐形式的偶氮吡唑啉酮化合物,该化合物用作颜料。

Description

单偶氮颜料
本发明涉及单偶氮颜料，具体而言，本发明涉及偶氮吡唑啉酮系列的橙色颜料。
塑料材料着色颜料的用途是公知的。为了得到橙颜色，人们传统使用无机颜料如镉、铅铬和钼酸盐橙色颜料，但是现在由于环境压力，它们逐渐被停止使用。人们已经建议用有机颜料作为这些无机颜料的替代物，但是，人们发现这些有机颜料在所有主要聚合物类型中，尤其是在它们的热稳定性方面不能完全令人满意。
现在人们发现，某些偶氮吡唑啉酮系列有机颜料当广泛用于塑料材料时，具有良好的热稳定性，光稳定性，和褪色坚牢度特征。
因此，本发明提供了以盐形式的下式的偶氮吡唑啉酮化合物：
式1化合物的盐可以具有多种形式(polyphormism)，在这种情况下，各种多晶型物被认为是在本发明的范围中。
具有很好的热和光稳定性的特别优选的式1化合物是其中萘环的磺酸基是在相对于偶氮键的4-或6-位，以及苯环的磺酸基是在相对于吡唑基的3-或4-位。
式1的偶氮吡唑啉酮化合物的盐可以是金属盐，例如碱金属，碱土金属或重金属盐，或者是含氮碱盐，例如伯、仲或叔胺或季铵盐，特别有用的颜料是钡，锶，锰，镁，钠和，尤其是钙盐。
本发明特别优选的化合物具有下式：
Figure A9519738600051
其中萘环的磺酸盐基是在相对于偶氮基的4-或6-位。
本发明偶氮吡唑啉酮化合物可以通过如下方法制备：将下式的萘胺磺酸重氮化：
Figure A9519738600052
和将得到的重氮化合物与下式的磺化3-甲基-1-苯基吡唑啉5-酮偶合：
和将得到的单偶氮化合物转化成所需的盐形式。
重氮化和偶合反应可以以适合于所使用的化合物类型的常规方式进行。
用于制备本发明化合物的优选的萘胺磺酸是1-萘胺-4-磺酸和1-萘胺-6-磺酸，而优选的偶合成分是3-甲基-1-(4’-磺基苯基)吡唑啉-5-酮和，尤其是3-甲基-1-(3’-磺基苯基)吡唑啉-5-酮。
通常以钠盐形式制备式1化合物，然后通常以水溶液形式加入所需数量的水溶性碱土金属或重金属盐将钠盐转化成，例如，碱土金属或重金属沉淀色料。
在合成式1化合物和/或沉淀颜料过程中，可以选择性地使用表面活性剂和/或有机溶剂。
本发明化合物可以经过常规的研磨操作和/或热处理以便得到所需颗粒度和/或结晶结构的产物，它们是可以以常规方式使用的橙色颜料。具体地说，它们可以单独使用或与其他染料结合使用，用于塑料，例如聚氯乙烯，聚烯烃，聚苯乙烯和ABS的着色，并且它们具有良好的性能。本发明化合物还具有表面涂覆颜料的价值。
下面的实施例用于说明本发明，但不是限制本发明。
实施例1
在置于冰浴中的容器中将1-萘胺-6-磺酸(4.46克)，去离子水(50毫升)和盐酸(5.1毫升)一起搅拌，接着加入足够的48％氢氧化钠溶液以形成对于亮黄试纸显碱性的溶液。然后将溶液冷却至0-5℃，再加入5.1毫升盐酸。一次性加入在去离子水(5毫升)中的亚硝酸钠(1.56克)溶液，将混合物在0-5℃搅拌30分钟。然后通过加入数毫升10％氨基磺酸溶液除去过量的亚硝酸盐。
将3-甲基-1-(3’-磺基苯基)吡唑啉-5-酮(5.4克)加入去离子水(50毫升)中，通过加入48％氢氧化钠溶液调节pH至6.5。然后将溶液在0-5℃搅拌，用10分钟加入如上面描述得到的重氮悬浮液，同时通过加入48％氢氧化钠溶液保持pH在6.5。然后在室温下将偶合混合物搅拌过夜。
然后将反应混合物加热至90℃，一次性加入氯化钙溶液(32克氯化钙在40毫升水中)，将混合物在90℃再搅拌3小时。然后将混合物热过滤，产物用去离子水(1000毫升)洗涤以除去氯化物，干燥得到7.3克橙色固体。
实施例2
在置于冰浴中的容器中将1-萘胺-4-磺酸钠盐(6.14克)，去离子水(50毫升)和盐酸(5.1毫升)一起搅拌，接着加入足够的48％氢氧化钠溶液以形成对于亮黄试纸显碱性的溶液。然后将溶液冷却至0-5℃，再加入5.1毫升盐酸。一次性加入在去离子水(5毫升)中的亚硝酸钠(1.56克)溶液，将混合物在0-5℃搅拌30分钟。然后通过加入数毫升10％氨基磺酸溶液除去过量的亚硝酸盐。
将3-甲基-1-(3’-磺基苯基)吡唑啉-5-酮(6.08克)加入去离子水(50毫升)中，通过加入48％氢氧化钠溶液调节pH至6.5。然后将溶液在0-5℃搅拌，用10分钟加入如上面描述得到的重氮悬浮液，同时通过加入48％氢氧化钠溶液保持pH在6.5。然后在室温下将偶合混合物搅拌过夜。
然后将反应混合物加热至90℃，一次性加入氯化钙溶液(32克氯化钙在40毫升水中)，将混合物在90℃再搅拌3小时。然后将混合物热过滤，产物用去离子水(1000毫升)洗涤以除去氯化物，干燥得到8.4克橙色固体。
实施例3
在置于冰浴中的容器中将1-萘胺-4-磺酸(5.74克)，去离子水(50毫升)和盐酸(5.1毫升)一起搅拌，接着加入足够的48％氢氧化钠溶液以形成对于亮黄pH试纸显碱性的溶液。然后将溶液冷却至0-5℃，再加入5.1毫升盐酸。一次性加入在去离子水(5毫升)中的亚硝酸钠(1.56克)溶液，将混合物在0-5℃搅拌30分钟。然后通过加入数毫升10％氨基磺酸溶液除去过量的亚硝酸盐。
将3-甲基-1-(4’-磺基苯基)吡唑啉-5-酮(5.6克)加入去离子水(50毫升)中，通过加入48％氢氧化钠溶液调节pH至6.5。然后将溶液在0-5℃搅拌，用10分钟加入如上面描述得到的重氮悬浮液，同时通过加入48％氢氧化钠溶液保持pH在6.5。然后在室温下将偶合混合物搅拌过夜。
然后将反应混合物加热至90℃，一次性加入氯化钙溶液(32克氯化钙在40毫升水中)，将混合物在90℃再搅拌3小时。然后将混合物热过滤，产物用去离子水(1000毫升)洗涤以除去氯化物，干燥得到3.4克橙色固体。

Claims (9)

1.一种盐形式的下式的偶氮吡唑啉酮化合物：
2.根据权利要求1的化合物，其中萘环的磺酸基是在相对于偶氮键的4-或6-位，以及苯环的磺酸基是在相对于吡唑基的3-或4-位。
3.根据权利要求1或2的化合物，其中的盐是金属盐或含氮碱盐。
4.根据权利要求3的化合物，其中的盐是钙盐。
5.根据权利要求4的具有下式的化合物：
Figure A9519738600022
其中萘环的磺酸基是在相对于偶氮键的4-或6-位。
6.一种制备如权利要求1定义的偶氮吡唑啉酮化合物的方法，该方法包括将下式的萘胺磺酸重氮化：
和将得到的重氮化合物与下式的磺化3-甲基-1-苯基吡唑啉-5-酮偶合：
Figure A9519738600032
和将得到的单偶氮化合物转化成所需的盐形式。
7.根据权利要求6的方法，其中萘胺磺酸包括1-萘胺-4-磺酸和/或1-萘胺-6-磺酸。
8.根据权利要求6或7的方法，其中磺化3-甲基-1-苯基吡唑啉-5-酮包括3-甲基-1-(4’-磺基苯基)吡唑啉-5-酮和/或3-甲基-1-(3’磺基苯基)吡唑啉-5-酮。
9.如权利要求1中定义的偶氮吡唑啉酮化合物作为颜料的用途。
CN95197386A 1995-01-20 1995-12-05 单偶氮颜料 Expired - Fee Related CN1085234C (zh)

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GBGB9501089.8A GB9501089D0 (en) 1995-01-20 1995-01-20 Monoazo pigments
GB9501089.8 1995-01-20

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CN1085234C CN1085234C (zh) 2002-05-22

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EP (1) EP0804510B1 (zh)
JP (1) JP3963396B2 (zh)
KR (1) KR100406649B1 (zh)
CN (1) CN1085234C (zh)
AT (1) ATE184305T1 (zh)
AU (1) AU694286B2 (zh)
BR (1) BR9510198A (zh)
CZ (1) CZ289337B6 (zh)
DE (1) DE69512087T2 (zh)
ES (1) ES2135780T3 (zh)
GB (2) GB9501089D0 (zh)
HK (1) HK1003269A1 (zh)
MX (1) MX9705357A (zh)
MY (1) MY113229A (zh)
SK (1) SK282191B6 (zh)
TW (1) TW334472B (zh)
WO (1) WO1996022334A1 (zh)
ZA (1) ZA9510624B (zh)

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CN101376748B (zh) * 2007-08-27 2011-09-14 明德国际仓储贸易(上海)有限公司 黄色染料化合物及其之墨水组成物

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US5997628A (en) * 1998-06-08 1999-12-07 Engelhard Corporation Heat stable laked monoazo pigment compositions
US6235100B1 (en) * 1999-06-24 2001-05-22 Engelhard Corporation Metallized azo yellow pigments
US6294012B1 (en) 1999-11-15 2001-09-25 Engelhard Corporation High strength monoazo yellow pigment
US6375733B1 (en) 2000-08-28 2002-04-23 Engelhard Corporation Heat stable monoazo magenta pigment compositions
US7927703B2 (en) 2003-04-11 2011-04-19 3M Innovative Properties Company Adhesive blends, articles, and methods

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US3802836A (en) * 1972-10-30 1974-04-09 Du Pont Aqueous dye baths containing mixtures of acidic dyes for deep-dyeing nylon yarns
DE3543541A1 (de) * 1985-12-10 1987-06-11 Sueddeutsche Kuehler Behr Flaechenwaermetauscher
DE3543512A1 (de) * 1985-12-10 1987-06-11 Bayer Ag Azofarblacke

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101376748B (zh) * 2007-08-27 2011-09-14 明德国际仓储贸易(上海)有限公司 黄色染料化合物及其之墨水组成物

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DE69512087T2 (de) 2000-03-30
WO1996022334A1 (en) 1996-07-25
JP3963396B2 (ja) 2007-08-22
KR100406649B1 (ko) 2004-03-31
US5744590A (en) 1998-04-28
MX9705357A (es) 1997-10-31
GB9524738D0 (en) 1996-02-07
KR19980701510A (ko) 1998-05-15
SK282191B6 (sk) 2001-12-03
EP0804510A1 (en) 1997-11-05
DE69512087D1 (de) 1999-10-14
HK1003269A1 (en) 1998-10-23
GB9501089D0 (en) 1995-03-08
EP0804510B1 (en) 1999-09-08
CN1085234C (zh) 2002-05-22
JPH10512302A (ja) 1998-11-24
ZA9510624B (en) 1996-07-22
BR9510198A (pt) 1997-12-23
ES2135780T3 (es) 1999-11-01
ATE184305T1 (de) 1999-09-15
CZ228497A3 (en) 1997-10-15
MY113229A (en) 2001-12-31
SK98997A3 (en) 1997-11-05
TW334472B (en) 1998-06-21
AU3990395A (en) 1996-08-07
CZ289337B6 (cs) 2002-01-16
AU694286B2 (en) 1998-07-16

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