CN1039040A - 塑料染色的染料 - Google Patents
塑料染色的染料 Download PDFInfo
- Publication number
- CN1039040A CN1039040A CN89104512A CN89104512A CN1039040A CN 1039040 A CN1039040 A CN 1039040A CN 89104512 A CN89104512 A CN 89104512A CN 89104512 A CN89104512 A CN 89104512A CN 1039040 A CN1039040 A CN 1039040A
- Authority
- CN
- China
- Prior art keywords
- group
- formula
- salt
- dyestuff
- acid
- 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.)
- Granted
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
- C09B69/00—Dyes not provided for by a single group of this subclass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- 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
-
- 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
- C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
-
- 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
- Y10S8/924—Polyamide fiber
-
- 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
- Y10S8/928—Polyolefin fiber
-
- 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
- Y10S8/938—Solvent dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polyamides (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
一种由离子性染料与化合物所成的盐,该化合物含有至少一个羧酸或磺酸基,或至少一铵基、环铵基或亚铵基,以及含有至少一脂肪族、环脂族、芳香族或杂芳族基团;或是C2-14二羧酸或氨基C2-12烷基二羧酸。当所述盐应用于合成聚胺材料,可使染色之坚牢度极佳。
Description
本发明涉及与塑料一起使用的改进了湿性牢度的染料。
经已指出,用阴离子染料进行本体染色的合成聚酰胺纤维材料,其湿性牢度很差,特别是洗涤湿性牢度差。它的染料不均匀地流失,进入洗涤液中,引起了消费者的不满。
现已发现一类染料,这类染料特别适于合成聚酰胺的本体染色,特别是加工成纤维材料的聚酰胺,经过染色的聚酰胺的湿性牢度有相当程度的改进。
因此,本发明是提供一种式(Ⅰ)的盐,
F·(A)n (Ⅰ)
式中的F为阴离子或阳离子染料基团;
当F为阴离子染料基团时,A为含有至少一个铵基、环铵基或亚铵基,以及含有至少被一个羰基取代的一个脂肪族、环脂族或芳香族基团,或者一个选自三嗪啶、嘧啶、喹啉唑、喹喔啉、2,3-二氮杂萘或苯并[C]吡咯酮系列的芳香杂环基团所构成的基团,并且其中基团A含至少一个脂族或环状脂族基团,并含有至少一个环铵基;或者
当F为阳离子染料基团时,A为含有至少一个羧酸基或磺酸基,和含有一个脂肪族、环脂族、芳香族或芳香杂环基团所构成的基团,或为C2-14二羧酸或氨基-C2-12烷基羧酸;
n为1、2、3或4;
适合的F基团为阴离子染料基团,如偶氮、蒽醌、酞菁或二噁嗪系列的染料,优先选择的是无磺酸基的金属偶氮染料,特别是铬配位染料。优先选择的阳离子染料的F基团是例如偶氮和三苯甲烷染料基团。
当F为阴离子染料基团时,优先选择的A为含一个或两个铵基和一个C1-12烷基、环己基、哌嗪、三嗪、嘧啶、喹唑啉、喹喔啉、2,3-二氮杂萘、邻苯二甲酰亚胺或苯桥基,其中最优先选择的是苯桥基或三嗪系列。
优先选择的铵基为环铵基,最优先选择的是2,2,6,6-四甲基哌啶或哌嗪基,哌嗪基连于铵氮原子上。
优先选择的n为1或2,最优先选择的是1。
优先选择的A基团包括选自被1至4个式(c)基团取代的苯系列基团,
(式中:当p=0时,c为R1a基,
当p=1时,c为R1b基;
R2=-O-或-NR3-;R3、R4、R5、R6分别为H或C1-2烷基)和2-位和4-位上被式R1a和式R1b取代,6-位被氯原子取代或(适合时)被式R1a基取代的三嗪基。以及2-位和4-位上分别被式
(式中R7为C1-4烷基)基团取代的、6-位上被氯取代的三嗪基。
当A含苯基时,最优先选择的苯基为被式R1a的一、二或三取代的苯基(即游离胺形式)和被式R1b的一或二取代的苯基(即碱式铵形式)。
当F为阳离子基团时,优先选择的A包括与含有1-4个羧酸或磺酸侧链相连接的一个芳族或芳族杂环桥基,或为C2-14二羧酸或氨基C2-12羧酸。
优先选择的酸侧链具有-XYZ结构(式中X=-NH-或-CONH-;Y=C1-14亚烷基或亚苯基;Z=-CO2H或-SO3H。
在本发明说明书中,能够是线形或支链的任何基团即可以是线形或支链的,即亚烷基可以是线形的或支链形的。
本发明的盐可用于塑料的本体染色,例如各种类型的聚酰胺、更适于加工成纤维材料的合成聚酰胺、PVC、聚烯烃、ABS和粘胶。
用这些盐制得的染色产品,其色彩牢固高而且光泽性好,尤其是与其中F未与A基团连接的相应染料相比有相当好的湿性牢度。
能形成本发明中的F基团并能反应生成本发明中的盐适合的染料是如《颜色索引》,第三版(1971)(Colour Index,Third Edition,1971)和其补篇中所述及的染料(也请参阅《1987年国际颜色索引》Colour International 1987),它们是在“酸性染料”、“直接染料”和含酸性基或碱性基的“溶剂染料”以及“碱性染料”栏目下的染料;适合的染料还有最新发展的性质相似的各种染料。这些染料在常用溶剂中一般都比普通溶剂染料的溶解度好。例如,它们大多数在乙醇中的溶解度都能达到400克/升。
特别优先选择的组分A(以游离氨基或环氨基形式表示)有:
1.三-(2′,2′,6′,6′-四甲哌啶-4′-基)-1,3,5-三苯甲酸三酰胺
2.2,4-双(2′,2′,6′,6′-四甲哌啶基-4′-氨基)-6-氯三嗪
3.2,4,6-三(2′,2′,6′,6′-四甲哌啶基-4′-氨基)三嗪
4.双(2′,2′,6′,6′-四甲哌啶基-4′-氨羰基对亚苯基)]对苯二甲酸二酰胺
5.双(2′,2′,6′,6′-四甲哌啶-4′-基)对苯二甲酸二酰胺
6.2,4-双(2′,2′,6′,6′-四甲哌啶基-4′-氨基)喹唑啉
7.2,3-双(2′,2′,6′,6′-四甲哌啶基-4′-氨基)喹唑啉
8.1,4-双(2′,2′,6′,6′-四甲哌啶基-4′-氨基)-2,3-二氮杂萘
9.2-氯-4,6-双(2′,2′,6′,6′-四甲哌啶基-4′-氨基)嘧啶
10.2,5-二氯-4,6-双(2′,2′,6′,6′-四甲哌啶基-4′-氨基)嘧啶
11.2-氟-5-氯-4,6-双(2′,2′,6′,6′-四甲哌啶基-4′-氨基)嘧啶
12.2,4,6-三(2′,2′,6′,6′-四甲哌啶基-4′-氨基)嘧啶
13.2,4,6-三(2′,2′,6′,6′-四甲哌啶基-4′-氨基)-5-氯嘧啶
33.(CH3)2C(CONH-R1)2
34.H2N-(CH2)8-CONH-R1
式14-34中的R1为式
(2′,2′,6′,6′-四甲哌啶-4-基)
优先选择的化合物A(以游离酸的形式与碱性染料形成盐)有:
35.H2N-(CH2)8-COOH
37.4-苯甲酰氨基苯甲酸
47.2,4-双-(4′-羧苯基氨基)-6-氯三嗪
49.1,4-双(4′-羧苯基氨基羰基)苯
50.1,3-双(4′-羧苯基氨基羰基)苯
51.1,2-双(4′-羧苯基氨基羰基)苯
52.4-苯基丁酸
53.1,4-丁二酸
54.1,2-乙二酸
阴离子染料之例有:
C.I.酸性兰 25,40,72,106,126,129,227,230,278和296,
C.I.酸性黄59,112,114,127和129,
C.I.酸性红261和404,
C.I.酸性绿40,
C.I.酸性橙82,
C.I.酸性紫66,
C.I.酸性棕28,30和289,
C.I.酸性黑58和115,
C.I.溶剂黄83,
C.I.溶剂红90∶1,和91和92,
C.I.溶剂黑45;
阳离子染料之例有:
C.I.碱性黄13和49,
C.I.碱性橙40,
C.I.碱性绿4,
C.I.碱性红14,22,46和49,
C.I.碱性紫16,
C.I.碱性兰41,54和78。
部分新的组成A-含氨基或亚氨基化合物可用本技术领域中熟知的方法进行生产[由酰氯(例如1,3,5-苯三甲酸三酰氯,实例1)和胺(例如2,2,6,6-四甲基-4-氨基哌啶)形成酰胺,胺与三嗪基卤化物的缩合等]。
式Ⅰ的染料的盐的生产可用任何本技术领域已知的方法。酸性染料随其生产(如钠盐),一般可在适量的无机酸(如盐酸)存在下与碱性组分A反应,而同时形成盐。阳离子染料最好是在略带碱性的介质中,与含酸性基组分A反应。本体染色按已知的方法进行。
聚酰胺的合成是按此类合成材料的任何已知方法进行的,特别是按制备二羧酸和二胺(例如己二酸和己二胺)和内酰胺(例如ω-氨基十一烷酸)缩聚物或聚合物的方法。与式Ⅰ染料混合的聚酰胺融体是用常用的方法成型的,例如在融纺机、注塑机、挤压机或吹膜机中成型。
实例1
组分A的制备(上述各式中的式1)
在催化量(3ml)的二甲基甲酰胺存在下,将42.0g1,3,5-苯三甲酸与144.0ml亚硫酰氯一起于80℃加热5小时,然后蒸出剩余的亚硫酰氯,将形成的1,3,5-苯三甲酸三酰氯溶于500ml二噁烷中。在搅拌下滴加总量为187.2g的2,2,6,6-四甲基-4-氨基哌啶,并不时加入二噁烷(总量为2000ml)使反应混合物(温度不能超过30℃)保持能被搅动。最后将反应混合物沸腾48小时并回流冷却,残渣过滤,用丙酮洗涤,溶于约1000ml的水中,用碱溶液(pH10-11)再沉淀,过滤,残渣用水洗涤和真空干燥(产率72%,89.2g,呈白色粉状,熔点>320℃)。
本发明的染料的盐的制备:
将20.8g式a1的红染料于200ml水中的溶液、0.75ml的3%HCl溶液和0.4g水杨酸加热至40℃历时,在搅拌下将上面得到的三酰胺15.6g于30ml水和2.6ml30%盐酸中的溶液缓慢与之混合,于40℃下再搅拌1小时,滤出沉降物,水洗,真空干燥得到21g深红色式a2产物,熔点大于320℃。
R1=2,2,6,6-四甲哌啶-4-基
应用实例(“份”指重量份)
在鼓式混合器中将100份聚-ε-己内酰胺粉与1份上述实例所制得的染料混合,短时间内粉状物即均匀分散,约10分钟后将混合物于120℃下干燥16小时。置混合物于融纺机,于275-280℃在氮气中停留8分钟,然后拉成纤维。此红色纤维具有优异的耐光、耐洗涤和耐磨性。
将下述染料:
C.I.酸性黄155(实例2)
C.I.酸性紫66(实例3)
C.I.酸性红216(实例4)代替式a1的染料按上述方法进行反应制取本发明的染料(形成盐),将聚-ε-己内酰胺染色,拉成纤维。
用类似实例1的方法将实例1的染料与上述组成A 2-34进行反应形成盐,按上述应用实例拉成纤维。
实例5
将261.5g2,4-双(羧甲基氨基)-6-氯三嗪(上述式46)分散在300ml蒸馏水中,在搅拌下将其加入40gNaOH于300ml蒸馏水的溶液,室温搅拌1小时左右,接着加入697.4g纯C.I.碱性红46染料。混合物在室温下再搅拌1小时。滤出混合物中形成的红色染料并进行干燥。此染料在乙醇中的溶解度大于250g/l。
应用实例2(“份”指重量份,“%”指重量百分数)
在搅拌下将5份实例2的染料盐加入95份含下列组分的硝基纤维素清漆:
用35%异丙醇润湿的硝基纤维素A15(白色片状) 18.8%
聚丙烯酸丁酯,软化树脂(Acronal 4F,BASF产品) 6.3%
二苯基辛基磷酸酯,软化剂(Santicizer 141,Monsanto产品3.3%
甲氧基丙醇(Dowanol PM,Dow Chemicals产品) 10.0%
乙氧基丙醇 10.0%
乙醇 41.6%
乙酸乙酯 10.0%
将其置于滚动机构上过夜,使其完全溶解。
制取两种铝箔:
a)未涂硝基纤维素清漆
b)涂以无色硝基纤维素清漆,涂覆25μm流动的湿清漆混合物膜,于130℃干燥5小时。
以干膜的透明度评估染料盐的稠度;使用透明胶纸(scotch tape)试验测定对未涂清漆和事先涂有清漆的铝箔的粘合强度。试验证明两种性质均属理想。
Claims (12)
1、一种式(Ⅰ)的盐
F·(A)n(Ⅰ)
式中的F为阴离子或阳离子染料基团;
当F为阴离子染料基团时,A为含有至少一个铵基、环铵基或亚铵基,及含有至少被一个羰基取代的一个脂肪族、环脂族或芳香族基团,或者选自三嗪、嘧啶、喹唑啉、喹喔啉、2,3-二氮杂萘或苯并[C]吡咯酮系列的芳香杂环基团所构成的基团,并且其中基团A含至少含一个脂肪族或环状脂肪族基团,并含有至少一个环铵基;或者
当F为阳离子染料基团时,A为含至少一个羧酸基或磺酸基,和含有一个脂肪族、环脂族、单芳香族或芳香杂环基团所构成的基团,或为C2-14二羧酸或氨基-C2-12烷基羧酸;
n为1,2,3或4;
2、权利要求1的式(Ⅰ)的盐,其中F为阴离子染料基团,A为含有一个或两个铵基以及含有C1-12烷基、环己基、哌嗪、三嗪、嘧啶、喹唑啉、喹喔啉、2,3-二氮杂萘、邻苯二甲酰亚胺或苯桥基的基团,n为1或2。
3、权利要求1或2的式(Ⅰ)的盐,其中F为阴离子染料基团,A为含有一个或两个铵基和含有三嗪或苯系列桥基的基团,n为1。
4、上述任一项权利要求的式(Ⅰ)的盐,其中F为偶氮、蒽醌、酞菁或二噁嗪系列的阴离子染料基团。
5、上述权利要求中任一项所述的式(Ⅰ)的盐,其中F为无磺酸基的金属偶氮阴离子染料基团。
7、上述权利要求任一项所述的式(Ⅰ)的盐,其中F为阴离子染料基团,A为含有一个2,2,6,6-四甲哌啶鎓和一、二或三个2,2,6,6-四甲哌啶基的基团,二者均连接于4-位上。
8、权利要求1的式(Ⅰ)盐,其中F为偶氮或三苯甲烷系列的阳离子染料基团,A为含有与1-4个羧酸或磺酸侧链相连接的芳族或芳族杂环桥基的基团,或为-C2-14二羧酸或氨基C2-12羧酸。
9、按权利要求1-6的式(Ⅰ)的盐的制备方法,该方法包括:
a)在无机酸的存在下将游离酸或盐形式的阴离子染料与一碱性组分相反应;或
b)在碱存在下游离碱或盐形式的阳离子染料与一酸性组分进行反应。
10、合成聚酰胺的染色方法,该方法包括将权利要求1-8中任一项所述的式(Ⅰ)的或其混合物用作本体染色剂或溶剂染色剂。
11、关于任一实例1-5或式1-54上述的新化学中间体。
12、按权利要求1的盐,基本上按此所述并参照任一实例1-5或式1-54。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP3821981 | 1988-06-30 | ||
DE3821981 | 1988-06-30 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN94120032A Division CN1111700A (zh) | 1988-06-30 | 1994-12-29 | 合成聚酰胺的染色方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1039040A true CN1039040A (zh) | 1990-01-24 |
CN1029853C CN1029853C (zh) | 1995-09-27 |
Family
ID=6357547
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN89104512A Expired - Fee Related CN1029853C (zh) | 1988-06-30 | 1989-06-28 | 塑料染色的染料的制备方法 |
CN94120032A Pending CN1111700A (zh) | 1988-06-30 | 1994-12-29 | 合成聚酰胺的染色方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN94120032A Pending CN1111700A (zh) | 1988-06-30 | 1994-12-29 | 合成聚酰胺的染色方法 |
Country Status (22)
Country | Link |
---|---|
US (2) | US5037448A (zh) |
JP (1) | JP2833023B2 (zh) |
KR (1) | KR970002216B1 (zh) |
CN (2) | CN1029853C (zh) |
BE (1) | BE1004045A3 (zh) |
BG (1) | BG60938B2 (zh) |
BR (1) | BR8903212A (zh) |
CH (1) | CH677797A5 (zh) |
CZ (1) | CZ286276B6 (zh) |
DE (1) | DE3920029C2 (zh) |
EG (1) | EG19243A (zh) |
ES (1) | ES2013945A6 (zh) |
FR (1) | FR2633631B1 (zh) |
GB (1) | GB2220418B (zh) |
HK (1) | HK176895A (zh) |
IN (1) | IN175068B (zh) |
IT (1) | IT1232154B (zh) |
NL (1) | NL8901645A (zh) |
RO (1) | RO107414B1 (zh) |
RU (1) | RU2061007C1 (zh) |
SK (1) | SK396889A3 (zh) |
TR (1) | TR25927A (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1101431C (zh) * | 2000-12-25 | 2003-02-12 | 河北省鹿泉市星宇化工总厂 | 碱性紫11:1的制备方法 |
CN1101430C (zh) * | 2000-12-25 | 2003-02-12 | 河北省鹿泉市星宇化工总厂 | 碱性红1:1的制备方法 |
CN110343242A (zh) * | 2019-07-04 | 2019-10-18 | 岭南师范学院 | 一种光致变色的超支化偶氮聚酰胺及其制备方法 |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3920029C2 (de) * | 1988-06-30 | 1999-05-20 | Clariant Finance Bvi Ltd | Farbstoffe zum Färben von Kunststoffen |
US5510467A (en) * | 1989-01-03 | 1996-04-23 | Sandoz Ltd. | Salts of metal-free anionic phenylazopyrazolone dyes having cations containing sterically hindered amine groups |
US5493022A (en) * | 1989-10-03 | 1996-02-20 | Sandoz Ltd. | Brightener and light stabilizer salts |
DE4030520B4 (de) * | 1989-10-03 | 2004-12-23 | Clariant Finance (Bvi) Ltd. | Pigmentfarbstoffe |
CH684194A5 (de) * | 1991-01-26 | 1994-07-29 | Sandoz Ag | Pigmente in Form von intermolekularen Salzen von zwitterionischen Farbstoffen. |
FR2706475B1 (fr) * | 1993-06-16 | 1997-08-29 | Sandoz Sa | Teinture dans la masse de polymères synthétiques. |
US5804396A (en) * | 1994-10-12 | 1998-09-08 | Sugen, Inc. | Assay for agents active in proliferative disorders |
US5837815A (en) * | 1994-12-15 | 1998-11-17 | Sugen, Inc. | PYK2 related polypeptide products |
US5837524A (en) * | 1994-12-15 | 1998-11-17 | Sugen, Inc. | PYK2 related polynucleotide products |
JP3845128B2 (ja) * | 1995-06-07 | 2006-11-15 | パイロットインキ株式会社 | 温度依存性色彩記憶性樹脂組成物及びこれを用いた積層体 |
EP0832073B1 (en) * | 1995-06-07 | 2002-01-16 | Sugen, Inc. | Quinazolines and pharmaceutical compositions |
US7119174B2 (en) * | 1995-12-18 | 2006-10-10 | Sugen, Inc. | Diagnosis and treatment of AUR1 and/or AUR2 related disorders |
US6716575B2 (en) | 1995-12-18 | 2004-04-06 | Sugen, Inc. | Diagnosis and treatment of AUR1 and/or AUR2 related disorders |
BE1010331A3 (nl) * | 1996-06-06 | 1998-06-02 | Dsm Nv | Zuur aanverfbare vezel. |
US5851238A (en) * | 1996-07-31 | 1998-12-22 | Basf Corporation | Photochemically stabilized polyamide compositions |
US20020048782A1 (en) * | 1996-12-11 | 2002-04-25 | Sima Lev | Pyk2 related products and methods |
US6818440B2 (en) * | 1997-04-28 | 2004-11-16 | Sugen, Inc. | Diagnosis and treatment of alk-7 related disorders |
US6136433A (en) | 1997-05-01 | 2000-10-24 | Basf Corporation | Spinning and stability of solution-dyed nylon fibers |
US6228641B1 (en) | 1997-05-20 | 2001-05-08 | Sugen, Inc. | Diagnosis and treatment of PTP04 related disorders |
US7115710B2 (en) * | 1997-06-11 | 2006-10-03 | Sugen, Inc. | Diagnosis and treatment of PTP related disorders |
US6342593B1 (en) | 1997-06-11 | 2002-01-29 | Sugen, Inc. | Diagnosis and treatment of ALP related disorders |
US6388063B1 (en) * | 1997-06-18 | 2002-05-14 | Sugen, Inc. | Diagnosis and treatment of SAD related disorders |
GB9800935D0 (en) | 1998-01-17 | 1998-03-11 | Clariant Int Ltd | Improvements in or relating to organic compounds |
CA2318403A1 (en) | 1998-01-21 | 1999-07-29 | Sugen, Inc. | Human orthologues of wart |
CA2369172A1 (en) * | 1998-04-14 | 1999-10-21 | Sugen, Inc. | Ste20-related protein kinases |
US6861442B1 (en) * | 1998-12-30 | 2005-03-01 | Sugen, Inc. | PYK2 and inflammation |
US7364866B2 (en) * | 1999-10-22 | 2008-04-29 | Pharmacia & Upjohn Company | Drosophila G protein coupled receptors, nucleic acids, and methods related to the same |
CA2388599A1 (en) * | 1999-10-22 | 2001-05-03 | Pharmacia & Upjohn Company | Drosophila g protein coupled receptors, nucleic acids, and methods related to the same |
US20030162223A1 (en) * | 1999-10-22 | 2003-08-28 | Lowery David E. | Drosophila G protein coupled receptors, nucleic acids, and methods related to the same |
US20030082534A1 (en) * | 1999-11-16 | 2003-05-01 | Peter Lind | Novel G protein-coupled receptors |
CA2388865A1 (en) * | 1999-11-16 | 2001-05-25 | Pharmacia & Upjohn Company | Novel g protein-coupled receptors |
US20050069976A1 (en) * | 2001-02-14 | 2005-03-31 | Peter Lind | Protein-coupled receptor |
DE602007010458D1 (de) | 2006-06-23 | 2010-12-23 | Basf Se | Reversible thermochrome zusammensetzungen |
US20110008347A1 (en) * | 2006-12-01 | 2011-01-13 | Agency For Science ,Technology And Research | Cancer-related protein kinases |
EP1932834B1 (en) * | 2006-12-11 | 2011-04-27 | The Genetics Company, Inc. | Aromatic 1,4-DI-Carboxylamides and their use |
CN110408055A (zh) * | 2019-08-13 | 2019-11-05 | 深圳市前海幸运色彩科技有限公司 | 一种abs/pc复合基料的染色工艺 |
CN110408054A (zh) * | 2019-08-13 | 2019-11-05 | 深圳市前海幸运色彩科技有限公司 | 一种尼龙基料的染色工艺 |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB215673A (en) * | 1923-11-29 | 1924-05-15 | Alfred Taylor | Improvements in optical instruments |
GB814605A (en) * | 1954-07-26 | 1959-06-10 | Hoechst Ag | Disazo dyestuffs derived from 1-phenyl-5-pyrazolone-3-carboxylic acid |
GB814695A (zh) * | 1956-05-17 | |||
GB882837A (en) * | 1959-06-10 | 1961-11-22 | Ici Ltd | New solvent dyes comprising salts of cationic dyestuffs |
DE1260652B (de) * | 1960-08-09 | 1968-02-08 | Basf Ag | Verfahren zur Herstellung von Ammoniumsalzen von Metallkomplexfarbstoffen |
NL294522A (zh) * | 1962-03-29 | |||
DE1263947B (de) * | 1962-04-13 | 1968-03-21 | Basf Ag | Verfahren zur Herstellung von Ammoniumsalzen sulfonsaeuregruppenhaltiger Chromkomplexfarbstoffe |
DE1195887B (de) * | 1962-10-04 | 1965-07-01 | Bruno V Zychlinski Dr Ing | Verfahren zur Herstellung von Farbstoffen |
US3467482A (en) * | 1965-02-25 | 1969-09-16 | Du Pont | Process for imparting improved dyelightfastness to basic dyeable polyester structures |
SE323959B (zh) * | 1965-12-21 | 1970-05-19 | Pharmacia Ab | |
DE1644440A1 (de) * | 1965-12-30 | 1970-10-29 | Basf Ag | Verfahren zur Herstellung von Benzoaten basischer Farbstoffe |
CH524012A (de) * | 1969-02-25 | 1972-01-31 | Ciba Geigy Ag | Verfahren zum kontinuierlichen Färben oder Bedrucken von Textilmaterial aus synthetischen Polyamid |
DE2021899A1 (de) * | 1970-05-05 | 1971-11-25 | Basf Ag | Sulfonsaeuregruppenhaltige Farbstoffe und deren Salze |
US4102639A (en) * | 1970-11-24 | 1978-07-25 | Ciba-Geigy Corporation | Amine salts of reactive dyestuffs |
CH549088A (de) * | 1970-11-24 | 1974-05-15 | Ciba Geigy Ag | Verfahren zur herstellung von aminsalzen von reaktivfarbstoffen. |
GB1433917A (en) * | 1972-07-15 | 1976-04-28 | Sakura Color Prod Corp | Ink composition |
US4028334A (en) * | 1973-04-11 | 1977-06-07 | Ciba-Geigy Corporation | Piperidine derivatives |
JPS5130019A (ja) * | 1974-09-04 | 1976-03-13 | Pentel Kk | Suiseiinkisoseibutsu |
DE2451219C3 (de) * | 1974-10-29 | 1978-06-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung konzentrierter Lösungen von Farbstoffen und Farbstoffzwischenprodukten und Verwendung der Lösungen |
DE2534830A1 (de) * | 1975-08-05 | 1977-02-24 | Bayer Ag | Farbstoffsalze |
EP0000331B1 (de) * | 1977-06-23 | 1983-12-28 | Ciba-Geigy Ag | Verfahren zum Färben linearer Polyamide in der Masse mit Salzen von 1:2 Chromkomplex-monoazofarbstoffen; die damit erzeugten Fasern |
EP0253007A1 (en) * | 1986-07-15 | 1988-01-20 | The B.F. GOODRICH Company | Stabilized polymers, novel stabilizers, and synthesis thereof |
DE3136892A1 (de) * | 1981-09-17 | 1983-03-31 | Basf Ag, 6700 Ludwigshafen | Farbstoffe fuer druckfarben und neue farbstoffe |
GB2156373B (en) * | 1984-03-29 | 1987-10-07 | Ciba Geigy Ag | New bleachable dyes for use in photographic assemblies |
DE3416327A1 (de) * | 1984-05-03 | 1985-11-07 | Basf Ag, 6700 Ludwigshafen | Farbsalze sulfonsaeuregruppenhaltiger polyazofarbstoffe |
JPS6144957A (ja) * | 1984-08-09 | 1986-03-04 | Kao Corp | 塩基性染料錯塩組成物及びこれを用いる染色法 |
DE3434921A1 (de) * | 1984-09-22 | 1986-05-07 | Sandoz-Patent-GmbH, 7850 Lörrach | Heterocyclische monoazoverbindungen |
DE3434920A1 (de) * | 1984-09-22 | 1986-05-07 | Sandoz-Patent-GmbH, 7850 Lörrach | Salze anionischer farbstoffe und konzentrierte loesungen davon |
NL8403612A (nl) * | 1984-11-28 | 1986-06-16 | Philips Nv | Methode voor het vervaardigen van een waterbestendige kleurstoflaag op een substraat alsmede een substraat voorzien van een kleurstoflaag. |
JPS6230958A (ja) * | 1985-07-31 | 1987-02-09 | Fuji Photo Film Co Ltd | 溶液の調製方法およびそれに用いる検体担持体 |
JPS62177069A (ja) * | 1986-01-31 | 1987-08-03 | Asahi Chem Ind Co Ltd | 新規なフタロシアニン結晶およびこれを用いた電子写真用感光体 |
GB8530456D0 (en) * | 1985-12-11 | 1986-01-22 | Ciba Geigy Ag | Organic electro-conductive compounds |
DE3784362D1 (de) * | 1986-03-10 | 1993-04-08 | Ciba Geigy Ag | Neue aminsalze von azoverbindungen. |
EP0241419B1 (de) * | 1986-04-10 | 1993-05-19 | Sandoz Ag | Piperidylgruppen enthaltende Pigmente |
DE3920029C2 (de) * | 1988-06-30 | 1999-05-20 | Clariant Finance Bvi Ltd | Farbstoffe zum Färben von Kunststoffen |
-
1989
- 1989-06-20 DE DE3920029A patent/DE3920029C2/de not_active Expired - Fee Related
- 1989-06-26 GB GB8914638A patent/GB2220418B/en not_active Expired - Fee Related
- 1989-06-27 BE BE8900701A patent/BE1004045A3/fr not_active IP Right Cessation
- 1989-06-27 FR FR8908666A patent/FR2633631B1/fr not_active Expired - Fee Related
- 1989-06-27 RO RO140472A patent/RO107414B1/ro unknown
- 1989-06-27 CH CH2385/89A patent/CH677797A5/de not_active IP Right Cessation
- 1989-06-28 EG EG31589A patent/EG19243A/xx active
- 1989-06-28 CN CN89104512A patent/CN1029853C/zh not_active Expired - Fee Related
- 1989-06-28 IT IT8948138A patent/IT1232154B/it active
- 1989-06-29 NL NL8901645A patent/NL8901645A/nl active Search and Examination
- 1989-06-29 BR BR898903212A patent/BR8903212A/pt not_active IP Right Cessation
- 1989-06-29 CZ CS19893968A patent/CZ286276B6/cs not_active IP Right Cessation
- 1989-06-29 ES ES8902296A patent/ES2013945A6/es not_active Expired - Lifetime
- 1989-06-29 JP JP1165531A patent/JP2833023B2/ja not_active Expired - Fee Related
- 1989-06-29 TR TR89/0551A patent/TR25927A/xx unknown
- 1989-06-29 SK SK3968-89A patent/SK396889A3/sk unknown
- 1989-06-30 US US07/374,511 patent/US5037448A/en not_active Expired - Fee Related
- 1989-06-30 KR KR1019890009159A patent/KR970002216B1/ko not_active IP Right Cessation
-
1990
- 1990-06-25 IN IN507MA1990 patent/IN175068B/en unknown
-
1991
- 1991-07-26 US US07/736,149 patent/US5316553A/en not_active Expired - Fee Related
- 1991-11-14 RU SU5001990/04A patent/RU2061007C1/ru not_active IP Right Cessation
-
1994
- 1994-02-28 BG BG98621A patent/BG60938B2/bg unknown
- 1994-12-29 CN CN94120032A patent/CN1111700A/zh active Pending
-
1995
- 1995-11-16 HK HK176895A patent/HK176895A/xx not_active IP Right Cessation
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1101431C (zh) * | 2000-12-25 | 2003-02-12 | 河北省鹿泉市星宇化工总厂 | 碱性紫11:1的制备方法 |
CN1101430C (zh) * | 2000-12-25 | 2003-02-12 | 河北省鹿泉市星宇化工总厂 | 碱性红1:1的制备方法 |
CN110343242A (zh) * | 2019-07-04 | 2019-10-18 | 岭南师范学院 | 一种光致变色的超支化偶氮聚酰胺及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
NL8901645A (nl) | 1990-01-16 |
BE1004045A3 (fr) | 1992-09-15 |
IN175068B (zh) | 1995-04-29 |
DE3920029C2 (de) | 1999-05-20 |
ES2013945A6 (es) | 1990-06-01 |
KR970002216B1 (ko) | 1997-02-25 |
JP2833023B2 (ja) | 1998-12-09 |
CZ396889A3 (cs) | 1999-12-15 |
EG19243A (en) | 1994-11-30 |
US5037448A (en) | 1991-08-06 |
BG60938B2 (bg) | 1996-06-28 |
CH677797A5 (zh) | 1991-06-28 |
US5316553A (en) | 1994-05-31 |
GB8914638D0 (en) | 1989-08-16 |
CZ286276B6 (cs) | 2000-03-15 |
JPH0270765A (ja) | 1990-03-09 |
IT1232154B (it) | 1992-01-25 |
CN1029853C (zh) | 1995-09-27 |
BR8903212A (pt) | 1990-02-13 |
GB2220418B (en) | 1993-01-27 |
SK280710B6 (sk) | 2000-06-12 |
CN1111700A (zh) | 1995-11-15 |
RO107414B1 (ro) | 1993-11-30 |
KR900000429A (ko) | 1990-01-30 |
HK176895A (en) | 1995-11-24 |
FR2633631B1 (fr) | 1995-01-20 |
TR25927A (tr) | 1993-09-17 |
DE3920029A1 (de) | 1990-02-08 |
FR2633631A1 (fr) | 1990-01-05 |
GB2220418A (en) | 1990-01-10 |
SK396889A3 (en) | 2000-06-12 |
RU2061007C1 (ru) | 1996-05-27 |
IT8948138A0 (it) | 1989-06-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1029853C (zh) | 塑料染色的染料的制备方法 | |
CN1297611C (zh) | 二萘嵌苯颜料组合物 | |
DE2360876A1 (de) | Kationische farbstoffe | |
DE2359791C3 (de) | Isoindolinonpigmente und deren Verwendung | |
CN1667051A (zh) | 一种分散染料混合物 | |
CN1104512C (zh) | 溶液染色的尼龙纤维及其制备方法 | |
JP4410321B2 (ja) | 新規なジケトピロロピロール組成物 | |
CN1192063C (zh) | 高强度单偶氮黄色颜料 | |
CN1113251A (zh) | 具有高色度的二酮基吡咯并吡咯颜料 | |
CN1942528A (zh) | 染色方法 | |
DE2357830A1 (de) | Metall-chelat-pigmente | |
CN1057526C (zh) | 二酮基吡咯并吡咯颜料的新的结晶变体 | |
CN1309152A (zh) | 三元颜料组合物 | |
CN1156488A (zh) | 聚酰胺的荧光增白方法 | |
DE2031202A1 (de) | Hydrazonfarbstoffe | |
DE1170569B (de) | Verfahren zur Herstellung von Farbstoffen | |
CA1066292A (en) | Mixed complexes of methine dyes | |
CN1541259A (zh) | 荧光二酮基吡咯并吡咯类似物 | |
CN1509304A (zh) | 由聚酰胺和2,6-二胺基吡啶衍生物制得的体系及其生产方法 | |
CN1407025A (zh) | 苯乙烯基染料的制备 | |
DE2040652B2 (de) | Methinfarbstoffe | |
CN1379778A (zh) | 制备嘧啶并[5,4-g]蝶啶衍生物的方法 | |
CN1761650A (zh) | 化合物,其制备方法及其作为染料和颜料的应用 | |
CN1099777A (zh) | 盐形式染料 | |
JP2006524729A (ja) | 新規な複素環式化合物、それらの調製方法及び染料及び顔料としてのそれらの使用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C53 | Correction of patent of invention or patent application | ||
CB02 | Change of applicant information |
Address after: The British Isles of Great Britain Applicant after: Krairi Anter Finanace (BVI) Co., Ltd. Address before: Basel, Switzerland Applicant before: Sandoz Ltd. |
|
COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: SANDOZ CO., LTD. TO: CLERIDES ANTROBUS FINANCE(BVI)LTD. |
|
C15 | Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993) | ||
OR01 | Other related matters | ||
C19 | Lapse of patent right due to non-payment of the annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |