[go: up one dir, main page]

CN1318515C - 基于羟基萘甲酸的双偶氮染料 - Google Patents

基于羟基萘甲酸的双偶氮染料 Download PDF

Info

Publication number
CN1318515C
CN1318515C CNB018155960A CN01815596A CN1318515C CN 1318515 C CN1318515 C CN 1318515C CN B018155960 A CNB018155960 A CN B018155960A CN 01815596 A CN01815596 A CN 01815596A CN 1318515 C CN1318515 C CN 1318515C
Authority
CN
China
Prior art keywords
compounds
paper
disazo
compound
dyes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CNB018155960A
Other languages
English (en)
Other versions
CN1455803A (zh
Inventor
G·－R·施雷特
S·埃贝尔特
K·－H·埃茨巴赫
R·特雷施
R·森斯
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of CN1455803A publication Critical patent/CN1455803A/zh
Application granted granted Critical
Publication of CN1318515C publication Critical patent/CN1318515C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/021—Disazo dyes characterised by two coupling components of the same type
    • C09B35/033—Disazo dyes characterised by two coupling components of the same type in which the coupling component is an arylamide of an o-hydroxy-carboxylic acid or of a beta-keto-carboxylic acid
    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/205—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene
    • C09B35/215—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene of diarylethane or diarylethene
    • 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
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
    • C09B44/06—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing hydroxyl as the only directing group
    • 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
    • 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
    • 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
    • Y10S8/919—Paper
    • 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
    • Y10S8/92—Synthetic fiber dyeing

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Paper (AREA)
  • Coloring (AREA)

Abstract

本发明涉及式(Ia)或(Ib)的双偶氮化合物，其中R1代表氢或甲基；基团X独立地代表-CH2CH2-或-CH2CH2CH2-；R2、R3或R4独立地代表氢或甲基；A代表阴离子；以及n代表A的化合价。本发明还涉及所述双偶氮化合物用于染色，特别是染纸的应用，以及包含该双偶氮化合物的染料。

Description

基于羟基萘甲酸的双偶氮染料
本发明涉及基于羟基萘甲酸的双偶氮染料、包含这些双偶氮染料的着色剂以及该双偶氮染料用于天然和合成材料染色的应用。
双偶氮染料是染料的大宗商品类别，已开发出许许多多此类型染料。
DE 198 15 945 A1公开一种阳离子磺酸染料，其中羟基氨基萘磺酸被偶氮偶合到两个苯基基团上，每个苯基基团带有一个具有季氮的取代基。
DE 1 768 892 A描述一种双偶氮染料，其中两个酰胺连接的羟基萘甲酸基团各自被偶氮偶合到双取代的苯基基团上。
DE 2 246 495 A描述一种基于羟基萘甲酰胺类的双偶氮染料。两个羟基萘甲酰胺基团通过偶氮键连接到芳族，例如，取代的或未取代的下列类型化合物上：
Figure C0181559600041
其中
A是酰氨基、硫脲、亚烷基二酰胺、亚苯基二酰胺、二硫键、偶氮、亚氨基、羰基或磺酰基。
US-A-4,046,502、DE 2 061 964 A和CH 5 554 399公开基于羟基萘甲酰胺类的非离子、单阳离子和二阳离子双偶氮染料。在此类双偶氮染料中，羟基萘甲酰胺基团通过偶氮键连接到下列类型的化合物上：
其中Y是直接键、取代或未取代的亚烷基、-S-、-O-、-NH-CO-NH-或-CH＝CH-。
这些已知类型染料在耐光性和亮度不令人满意。
本发明的目的是提供一种耐光性和亮度俱佳的进一步改进的染料。
我们发现这一目的通过下面式Ia和Ib所代表的化合物令人惊奇地实现了。
据此，本发明提供一种式Ia的双偶氮化合物
Figure C0181559600051
或式Ib的双偶氮化合物
Figure C0181559600052
其中
R1是氢或甲基，
X基团独立地是-CH2CH2-或-CH2CH2CH2-，
R2、R3和R4独立地是氢或甲基，
A是阴离子以及
n对应于A的化合价。
本发明还提供一种着色剂，它含有至少一种式I化合物，以及任选地其他阳离子、非离子或阴离子染料和/或助剂和/或载体。
本发明还提供式I化合物用于天然或合成聚合物材料、纸料、皮革、天然和合成纤维材料的染色、浸轧或印花的应用。
本发明还提供式I双偶氮化合物用于纸、纸材料、纤维素、棉花、皮革、天然纤维、合成纤维、天然纤维材料或者合成纤维材料的染色、浸轧或印花的应用。
本发明的双偶氮化合物是2-羟基萘-3-羧酸(BON酸)的衍生物。
在本发明双偶氮化合物中，X基团可相同或不同；优选它们相同。
类似地，NR2R3和NR2R3R4对可相同或不同；优选它们相同。尤其优选的是完全对称结构的双偶氮化合物。
NR2R3尤其是
Figure C0181559600061
NR2R3R4尤其是
通式Ib的阳离子双偶氮化合物要求Aθ阴离子是电中性的。有用的阴离子包括无机和有机阴离子，例如，氟、氨、溴、碘、硫酸根、硫酸二甲酯(methosulfate)、磷酸根、羧酸或磺酸的阴离子，例如，甲酸根、乙酸根、丙酸根，单-、二-或三氯乙酸根、乳酸根、甲氧基乙酸根、柠檬酸根、琥珀酸根、甲磺酸根、苯磺酸根、2-或4-甲基苯磺酸根或萘磺酸根。
本发明化合物可按照DE 2061964中描述的方法制备。它们优选地这样来制备：通式II的化合物进行重氮化，
Figure C0181559600063
随后，使通式III的化合物的偶氮偶合
继而进行季铵化，或替代地，进行通式IV偶合组分的季铵化
并随后按合适的摩尔比进行偶氮偶合。X、R1、R2和R3在这里各自具有上面提到的含义。
季铵化例如可通过通式IV的化合物与R4-A起反应来实施，其中R4和A各自如上所定义。R4-A的例子是碘甲烷和硫酸二甲酯。
重氮化、偶氮偶合、季铵化和缩合乃是熟知的方法，可按照惯用标准方法实施。
本发明还提供包含本发明化合物的着色剂。它们通常以0.1～20wt％的用量存在，以着色剂总重量为基准。
本发明的双偶氮化合物可单独、彼此混合或与其他阳离子或阴离子化合物一起，以溶液形式或者以粉末或颗粒形式使用，即，它们非常容易混合。加工，例如加工成稳定液体或固体着色剂，可按已知方式实施，例如，通过研磨或造粒或者通过溶解在适当溶剂中，可在助剂，如稳定剂，的存在或不存在条件下完成。
该着色剂优选以水溶液形式存在。它们可包含惯用助剂，例如，润湿剂、增稠剂、水混溶性有机溶剂等。优选的增稠剂是聚合物，如聚丙烯酸、聚丙烯酸衍生物、聚乙烯基胺、聚乙烯基酰胺、聚醋酸乙烯、聚乙烯醇、聚乙烯基吡咯烷酮、聚硅氧烷或它们的共聚物。类似地，乙烯亚胺的、环氧乙烷的或环氧丙烷的低聚物或者它们的衍生物都可使用。
本发明的双偶氮化合物可用于各种各样材料的染色、浸轧和印花，特别是纸和纸材料、纤维素、棉花、皮革、韧皮纤维、大麻、亚麻、剑麻、黄麻、椰纤维或麦稻秸。它们尤其可用于下列材料的的染色、浸轧和印花：丙烯腈聚合物和丙烯腈共聚体纤维和用它们生产的纱线以及纺织品、合成、阴离子改性酰胺和聚酯，范围广泛的混纺织物和合成及天然树脂材料。它们类似地还可用于，例如，油漆或油墨，包括喷墨印刷油墨。
这些化合物优选地可在染色浆粕、施胶或不施胶纸的生产中作为染料。它们同样也可采用浸染方法用来染纸。
染色、浸轧和印花可按照熟知的方法实施。
本发明的双偶氮化合物的显著特点在于容易得到并且适合作为多种多样范围广泛的材料的染料并且染料性能也卓越。
该新染料仅给造纸废水染上最轻微的颜色，或者完全没有，这对于保持水源的清洁特别有利。它们具有高度直染性并且在纸上不造成斑纹(marble)并且对pH值基本上不敏感。尤其对纸的染色，但对其他材料的染色也是以耐光性好为特征。在长期暴露于光照后，色调上发生色彩改变。
染色的纸虽具有良好漂白性，但其耐湿性不仅对水，而且对牛奶、肥皂水、氯化钠溶液、果汁和甜味矿泉水来说都好。由于其耐醇牢度好，它们对酒精类饮料也表现稳定。
尤其在家用以及在可预见到染色纸将以湿态接触其他制品如纺织品的其他用途纸的情况下，耐流出特别重要。造纸工业储备了大量容易漂白的纸和染色纸浆粕，以便它们能够再加工或立即用于其他纸的品种生产。本发明的双偶氮化合物用于这样的目的非常适合。
值得注意的还有，它们具有优良抗迁移、耐热、耐光和耐气候性、洁净的色光和高色强度。
下面的非限定性实例用于说明本发明。
实例1
4.24g(0.02mol)4，4’-二氨基二苄基(＝1，2-二(4-氨基苯基)乙烷)，悬浮在100mL水中并通过加入12mL浓盐酸而溶解。溶液冷却至0℃，并与13.2mL 30％亚硝酸钠溶液混合。在0-5℃经过45min重氮化时间之后，过量亚硝酸盐通过加入约0.2g酰氨基磺酸而分解。如此制备的重氮组分的溶液在30min内滴加到10.9g(0.04mol)2-羟基-3-(3-(N，N-二甲氨基)丙基)萘甲酰胺在300mL水的0℃冷悬浮体中。随后，混合物在5℃搅拌1h。在此期间，pH值用20％氢氧化钠水溶液维持在8～9。随后，pH值通过进一步加入20％氢氧化钠水溶液调节到11，最后过滤离析出染料。干燥后获得13.94g(理论值的89.5％)下式的红色染料：
Figure C0181559600081
从乙酸乙酯/乙醇中重结晶的样品提供以下光谱数据：
UV/VIS谱(9∶1(体积比)甲醇/乙酸)：λmax＝536nm
类似于实例1，制备下列染料：
Figure C0181559600091
这些化合物的耐光性按照DIN ISO 105 B 02与下列各式化合物对比地进行了测定：
结果报告于下表1。
表1：
    化合物     耐光性
    A     1-2
    B     1-2
    C     ＜1
    D     ＜1
可以清楚地看出，本发明化合物A和B令人惊奇地具有比DE2061964的化合物C和D显著好的耐光性。另外，化合物A和B不引起自来水的混浊，不像化合物C和D那样。

Claims (4)

1.式Ia或Ib的双偶氮化合物
其中
R1是氢或甲基，
X基团独立地是-CH2CH2-或-CH2CH2CH2-，
R2、R3或R4独立地是氢或甲基，
A是阴离子以及
n对应于A的化合价。
2.权利要求1的双偶氮化合物，具有下式
Figure C018155960003C1
3.一种着色剂，它包含至少一种权利要求1或2的双偶氮化合物，并任选地还包含阳离子或阴离子或非离子染料和/或助剂。
4.权利要求1或2的双偶氮化合物用于纸、纸材料、纤维素、棉花、皮革、天然纤维、合成纤维、天然纤维材料或者合成纤维材料的染色、浸轧或印花的应用。
CNB018155960A 2000-09-14 2001-09-13 基于羟基萘甲酸的双偶氮染料 Expired - Fee Related CN1318515C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10045430A DE10045430A1 (de) 2000-09-14 2000-09-14 Bisazofarbstoffe auf der Basis von Hydroxynaphthalincarbonsäure
DE10045430.5 2000-09-14

Publications (2)

Publication Number Publication Date
CN1455803A CN1455803A (zh) 2003-11-12
CN1318515C true CN1318515C (zh) 2007-05-30

Family

ID=7656158

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB018155960A Expired - Fee Related CN1318515C (zh) 2000-09-14 2001-09-13 基于羟基萘甲酸的双偶氮染料

Country Status (10)

Country Link
US (1) US6933371B2 (zh)
EP (1) EP1317512B1 (zh)
JP (1) JP2004509208A (zh)
KR (1) KR20030040456A (zh)
CN (1) CN1318515C (zh)
AU (1) AU2002213911A1 (zh)
BR (1) BR0113827A (zh)
DE (2) DE10045430A1 (zh)
ES (1) ES2220820T3 (zh)
WO (1) WO2002022742A1 (zh)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4803783B2 (ja) * 2004-06-10 2011-10-26 大王製紙株式会社 未晒ライナーの製造方法
US9756798B2 (en) 2004-11-19 2017-09-12 Patti D. Rubin Burrow filling compressed growing medium
US20060107589A1 (en) 2004-11-19 2006-05-25 Rubin Patti D Compressed growing medium
WO2009058869A1 (en) 2007-10-29 2009-05-07 Oms Investments, Inc. Compressed coconut coir pith granules and methods for the production and use thereof
BR112016005924B8 (pt) 2013-09-18 2022-12-20 Advantec Sensing As Aparelho para determinar um valor de um parâmetro relacionado à permissividade elétrica de meios fluidos ou uma composição de meios fluidos a ser caracterizado em um primeiro recipiente

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2061964A1 (de) * 1969-12-17 1971-09-02 Sandoz Ag, Basel (Schweiz) Basische Azofarbstoffe, ihre Her stellung und Verwendung
DE2246495A1 (de) * 1971-09-24 1973-03-29 Toms River Chemical Corp Substantive disazofarbstoffe fuer papier

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH489577A (de) * 1967-07-11 1970-04-30 Geigy Ag J R Verfahren zur Herstellung von Disazopigmenten
GB1338250A (en) 1969-12-17 1973-11-21 Sandoz Ltd Basic azo dyes their production and use
CH554399A (de) 1969-12-17 1974-09-30 Sandoz Ag Verfahren zur herstellung sulfonsaeuregruppenfreier basischer azoverbindungen.
US4046502A (en) * 1973-11-23 1977-09-06 Sandoz Ltd. Basic disazo dyes having two 2-hydroxy-3-substituted carbamoylnaphthyl-1-azophenyl groups for dyeing paper
DE19815945A1 (de) 1998-04-09 1999-10-14 Basf Ag Kationische Sulfonsäurefarbstoffe

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2061964A1 (de) * 1969-12-17 1971-09-02 Sandoz Ag, Basel (Schweiz) Basische Azofarbstoffe, ihre Her stellung und Verwendung
DE2246495A1 (de) * 1971-09-24 1973-03-29 Toms River Chemical Corp Substantive disazofarbstoffe fuer papier

Also Published As

Publication number Publication date
AU2002213911A1 (en) 2002-03-26
DE10045430A1 (de) 2002-03-28
US6933371B2 (en) 2005-08-23
US20040010866A1 (en) 2004-01-22
DE50102487D1 (de) 2004-07-08
EP1317512A1 (de) 2003-06-11
WO2002022742A1 (de) 2002-03-21
JP2004509208A (ja) 2004-03-25
BR0113827A (pt) 2003-06-03
CN1455803A (zh) 2003-11-12
EP1317512B1 (de) 2004-06-02
ES2220820T3 (es) 2004-12-16
KR20030040456A (ko) 2003-05-22

Similar Documents

Publication Publication Date Title
SE445836B (sv) Basiska resp katjonaktiva, sulfonsyragrupphaltiga monoazo- eller diazoforeningar samt deras anvendning
US5352334A (en) The use of metal-free sulfo group free basic disazo compounds containing two identical 6-hydroxypyrid-2-one coupling component radicals for producing colored paper
CN1318515C (zh) 基于羟基萘甲酸的双偶氮染料
JP3902672B2 (ja) スルホン酸基を含む塩基性ジスアゾ化合物
US5424404A (en) Biscationic azo dyes and intermediates therefor
US7371831B2 (en) Azo dyestuffs
JPS6232222B2 (zh)
GB2104090A (en) Triazine compounds
US4486348A (en) Cationic triazine azo dyes
US4146558A (en) Azo dyestuff intermediate nitro- or aminobenzenes ring-substituted by a quaternized amine alkyl or amino-alkoxy group
EP0024321B1 (de) Kationische Azofarbstoffe, ihre Herstellung, ihre Verwendung zum Färben von Papier und sie enthaltende Mittel
US4065500A (en) Water-soluble quaternary ammonium azo dyestuffs
US3987022A (en) Yellow to orange disazo cationic dyes containing two heterocyclic quaternary ammonium groups
US6084078A (en) Disazo dyestuffs for dyeing cellulosic materials
CN1325572C (zh) 碱性偶氮化合物
US3839426A (en) Compounds and preparation thereof
US3890257A (en) Yellow to orange disazo cationic dyes containing two quaternary ammonium groups
JP2003500408A (ja) トリフェンジオキサジン化合物
US4517357A (en) Symmetrical bis-(triazinyamino phenyl azo acetoacetanilide) dyestuffs
US6346609B1 (en) Cationic azo-dyes
US6048969A (en) Cationic sulfonic acid dyes
Blus Synthesis and properties of disazo acid dyes
US4517358A (en) Disazo bis-benzthiazolyl compounds
US5286854A (en) Basic azo dyes with a coupling component of the hydroxynaphthalenecarboxylic acid series
US5010190A (en) Cationic compounds

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C14 Grant of patent or utility model
GR01 Patent grant
C17 Cessation of patent right
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20070530

Termination date: 20120913