CN1145905A - 取代的酞菁 - Google Patents
取代的酞菁 Download PDFInfo
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- CN1145905A CN1145905A CN96111095A CN96111095A CN1145905A CN 1145905 A CN1145905 A CN 1145905A CN 96111095 A CN96111095 A CN 96111095A CN 96111095 A CN96111095 A CN 96111095A CN 1145905 A CN1145905 A CN 1145905A
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- phthalocyanine
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- copper
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 238000007639 printing Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- LTTPAKZQRNKKMD-UHFFFAOYSA-N benzylazanide copper(1+) Chemical compound C(C1=CC=CC=C1)N[Cu] LTTPAKZQRNKKMD-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000000049 pigment Substances 0.000 description 14
- 239000000976 ink Substances 0.000 description 13
- -1 heterocyclic radical Chemical class 0.000 description 6
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 description 1
- MVORZMQFXBLMHM-QWRGUYRKSA-N Gly-His-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](NC(=O)CN)CC1=CN=CN1 MVORZMQFXBLMHM-QWRGUYRKSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000013500 data storage Methods 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000001093 holography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- DXYUWQFEDOQSQY-UHFFFAOYSA-N n'-octadecylpropane-1,3-diamine Chemical class CCCCCCCCCCCCCCCCCCNCCCN DXYUWQFEDOQSQY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/22—Obtaining compounds having nitrogen atoms directly bound to the phthalocyanine skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Paints Or Removers (AREA)
Abstract
本发明提供式(1)的酞菁：其中：MPc是式(2)的酞菁核；其中，M，X，R1，R2，a和b如说明书中所述。
Description
本发明涉及在近红外区吸收光波的酞菁颜料。
本发明提供式(1)的酞菁：
式(1)其中：MPc是式(2)的酞菁核；
式(2)其中
M是金属原子，氯-金属基，氧-金属基或氢
X是卤素
R1是一有机基团
R2是H或任意被取代的烷基
a具有平均值15至1
b具有平均值1至15
a+b等于4至16
优选的本发明酞菁在700至1000nm具有最大吸收(λmax)。
酞菁核可以是不合金属的，即M是氢，或M可以是金属，卤素-金属基或氧-金属基。合适的金属，卤素-金属基或氧-金属基是周期表IA，IIA，IIIB，IVB族，第一，第二和第三过渡金属和镧系金属。优选的金属，卤素-金属基和氧-金属基中的金属选自铜，锰，铁，锌和钴，尤其是铜。
在卤素-金属基中合适的卤原子是-Cl，-F，-Br，和-I，优选-Cl，-F和-Br。
在氧-金属基中氧是氧原子或羟基。
优选的是R1选自芳基，杂环基，脂环基和烷基，并可以被一个或多个取代基取代。当R1是芳基或杂环基时，优选地选自单或双环芳基或杂环基。合适的芳基或杂环基的例子有苯基，萘基，吡啶基，喹啉基，噻吩基，呋喃基，噻唑基和苯并噻唑基。当R1是脂环基时，优选地为C4-8-环烷基，更优选环己基。当R1或R2是烷基时，优选地各独立地为C1-10烷基，更优选C1-6烷基，尤其是C1-4烷基。
当由R1代表的有机基团任意被取代时，取代基选自C1-10烷基，优选C1-6烷基，C1-10烷氧基，优选C1-6烷氧基，-CN，-NO2，-CF3，卤素，优选-F，-Cl或Br，-NR3R4，-OR3，-SO2NR3R4-SO2R3，-CONR3R4，-CONR3R4，-COOR3，-COR3其中R3和R4各自独立地选自-H，C1-6-烷基，芳基，优选苯基，和C7-10芳烷基优选苄基。对由R1代表的有机基团特别优选的取代基是C1-6烷基，-OR3；其中R3是C1-6烷基，[NH(CH2)x]y-NH(CH2)nH其中x是2或3，y是0至5，而n为0至24，或-NR3R4其中R3和R4各自独立地为-H，C1-6-烷基，苯基或C7-10芳烷基。
当R2代表任意被取代的烷基时，取代基选自-OH，卤素，优选-Cl，-Br，或-F，-CN，-COOC1-6-烷基和苯基。
优选的式(I)化合物中M是Cu，R1是苄基或N-烷基氨基烷基，R2是H，而a+b等于12至16。
更优选的是其中M是Cu，R1是苄基或N-烷基氨基烷基，R2是H，a等于15至8而b等于1至8的化合物。而a+b可为15至16。
特别优选的式(I)化合物是八氯七(苄基氨基)铜酞菁，和十一氯-四(n-硬脂基-3-丙二氨基)铜肽菁。
根据本发明的另一方面，提供制备式(I)酞菁的方法：
式(I)通过式(3)的酞菁：
MPcXc
式3与式(4)化合物反应：
H-NR1R2
式4其中c为4至16例如15至16；而M，Pc，X，R1，和R2如前定义。
该方法通过任意在惰性液体存在下，在升高的温度下加热将式(3)酞菁与式(4)化合物混合而实施。
合适的惰性液体是酰胺如N-甲基吡咯烷酮或二甲基甲酰胺。
该方法优选地在没有惰性液体存在下进行。
该方法优选地在100℃至250℃的温度，更优选地在130℃至200℃的温度，尤其是在150℃至190℃的温度进行。
式(1)的酞菁可通过任何常规手段从反应混合物中分离，例如冷却反应混合物并倒入如乙醇的液体中，并滤出沉淀的产物。产物可通过用如乙醇的液体洗涤，或用如甲苯的液体作洗脱剂从硅胶洗脱而纯化。
式(3)化合物可通过卤化的-1，2-二氰基苯，例如四氯-1，2-二氰基苯，与适当的金属或金属盐在惰性有机液体中和升高的温度下反应制备。
本发明的酞菁可用于从例如激光源吸收电磁辐射，并可用于涂覆光学数据存储盘。
本发明的颜料可以是印墨的成分，该印墨可以被设计用于平板印刷，活版印刷，凹板印刷或网板印刷。该油墨可以含有0.1至20％，优选1至15％重量的颜料。该油墨可含有其它成分如干料和其它颜料。
本发明也包括合有油墨载体和本发明的颜料的油墨。
本发明的油墨可用于保密文件和需要鉴定的其它文件的印刷。在此文本中，用于印刷的基体一般是纸，包括用破布制造的纸，优选纸币级纸，塑面或层压纸，和塑料如，***级的PVC，或塑料纸，例如非纺织的塑料纸。带保密印刷的物品包括钞票，钞票线，货币，旅行支票，债券，证书，邮票，彩票，所有权文件，护照，身份证，***，借物卡，存取卡，罚卡，商标和标签，防信伪标记。
保密文件通常具有不同类型的印刷形式，选自凹板印刷，胶印平板印刷，活版印刷和有时也有照相凹版。本发明的油墨将通常以各种颜色被用于除保密印刷之外的领域。彩虹印刷技术通常被用于保密文件中。本发明的颜料也可被包括于电子照相调色剂，针式或菊花轮打印机墨，和非击打式打印法中。
本发明的颜料也可被包括(不是必须)，在用于纸包括破布制造的纸和塑料纸，钞票线，塑料卡和其它保密文件或需要被鉴别的文件的油墨中，如果需要，与聚合物混合并结合，而不是在油墨中。本发明的颜料如果需要或希望在条型码中，可沉积于单个区域或系列区域中。
本发明颜料可被掺入需要鉴定的文件中，例如，通过将其掺入标记如全息照相标记或在热模压片组成中。一般地，该颜料可在或接近被鉴定文件的表面。
本发明通过下列实施例进一步说明。
实施例1制备八氯七(苄基氨基)铜酞菁
苄胺(25份)和Pigment Green 7(1份)被回流4小时。然后冷却反应混合物，并倒入水中。产生的沉淀通过离心收集，水洗并室温干燥给出具有λmax(CHCl3)714nm的产物。
实施例2制备十一氯四(N-硬脂基-3-丙二氨基)铜酞菁
将N-硬脂基-1，3-二氨基丙烷(11.4份)和Pigment Green 7(1份)回流18小时。反应混合物被冷却并倒入冰乙酸中。离心收集产生的沉淀，用冰乙酸洗涤，直至洗出液变清，然后用水洗并室温干燥给出具λmax(1-甲基萘)723.2nm的产物。
实施例3
实施例1的颜料用三辊磨以10％(重量)的浓度分散到清亮的胶印油墨调墨油中，而印刷品用实验室清样得到。印刷品用UV-VIS-NIR分光光度计分析。最小反射(最大吸收)在720nm的观察到。
实施例4
实施例2的颜料用三辊磨以3％(重量)的浓度分散到清亮的胶印油墨调墨油中，印刷品用实验室清样得到。印刷品用UV-VIS-NIR分光光度计分析。最小反射(最大吸收)在715nm观察到。
Claims (11)
1.式(1)的酞菁：
式(I)其中
MPc是式(2)的酞菁核；
式(2)其中
M是金属原子，氯-金属基，氧-金属基或氢
X是卤原子
R1是一有机基团
R2是H或任意被取代的烷基
a具有平均值15至1
b具有平均值1至15
a+b等于4至16
2.如权利要求1的化合物，其中M是氢，铜，锰，铁，锌，或钴。
3.如权利要求1的化合物，其中M是铜，R1是苄基或N-烷基氨基烷基，而R2为氢。
4.化合物八氯七(苄基氨基)铜酞菁。
5.化合物十一氯四(N-硬脂基-1，3-丙二氨基)铜酞菁。
6.制备式(1)酞菁的方法：
式(I)通式(3)的酞菁：
MPcXc
式3与式(4)化合物反应：
H-NR1R2
式4其中c等于4至16；而M，Pc，X，R1，和R2如权利要求1中定义。
7.如权利要求6的方法，其中反应物在有或没有惰性液体存在下在升高温度时加热。
8.如权利要求7的方法，在100°至250℃进行。
9.一种油墨，含有油墨载体和如权利要求1至5的任一项要求的化合物。
10.如权利要求9的油墨，含有0.1至20％重量的所说的化合物。
11.权利要求9的油墨在保密文件印刷中的用途。
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9514994.4A GB9514994D0 (en) | 1995-07-21 | 1995-07-21 | Substituted phthalocyanines |
| GB9514994.4 | 1995-07-21 | ||
| GB9517421.5 | 1995-08-25 | ||
| GBGB9517421.5A GB9517421D0 (en) | 1995-08-25 | 1995-08-25 | Substituted phthalocyanines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1145905A true CN1145905A (zh) | 1997-03-26 |
Family
ID=26307440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96111095A Pending CN1145905A (zh) | 1995-07-21 | 1996-07-20 | 取代的酞菁 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0757084A1 (zh) |
| JP (1) | JPH0952894A (zh) |
| KR (1) | KR970010770A (zh) |
| CN (1) | CN1145905A (zh) |
| AU (1) | AU712884B2 (zh) |
| CA (1) | CA2181661A1 (zh) |
| CZ (1) | CZ214896A3 (zh) |
| MX (1) | MX9602888A (zh) |
| SK (1) | SK93796A3 (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7053285B2 (ja) * | 2018-01-25 | 2022-04-12 | 株式会社日本触媒 | フタロシアニン化合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB471435A (en) * | 1936-03-05 | 1937-09-06 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of dyestuffs |
| ATE51402T1 (de) * | 1984-03-21 | 1990-04-15 | Ici Plc | Infrarot-absorber. |
| JPS63170462A (ja) * | 1986-08-25 | 1988-07-14 | Nippon Shokubai Kagaku Kogyo Co Ltd | フタロシアニン化合物 |
| JPH0730300B2 (ja) * | 1988-04-01 | 1995-04-05 | 三井東圧化学株式会社 | アルキルフタロシアニン近赤外線吸収剤及びそれを用いた表示・記録材料 |
| EP0523959B1 (en) * | 1991-07-15 | 1999-10-13 | Nippon Shokubai Co., Ltd. | Novel phthalocyanine compounds, production method thereof, and near infrared ray absorption materials containing the same |
| EP0607031B1 (en) * | 1993-01-13 | 1999-10-06 | Nippon Shokubai Co., Ltd. | Heat radiation-shielding material |
| GB9315692D0 (en) * | 1993-07-29 | 1993-09-15 | Zeneca Ltd | Phthalocyanines |
-
1996
- 1996-07-10 EP EP96305094A patent/EP0757084A1/en not_active Withdrawn
- 1996-07-18 SK SK937-96A patent/SK93796A3/sk unknown
- 1996-07-19 MX MX9602888A patent/MX9602888A/es unknown
- 1996-07-19 CA CA002181661A patent/CA2181661A1/en not_active Abandoned
- 1996-07-19 JP JP8189828A patent/JPH0952894A/ja active Pending
- 1996-07-19 CZ CZ962148A patent/CZ214896A3/cs unknown
- 1996-07-20 KR KR1019960029498A patent/KR970010770A/ko not_active Application Discontinuation
- 1996-07-20 CN CN96111095A patent/CN1145905A/zh active Pending
- 1996-07-31 AU AU60606/96A patent/AU712884B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA2181661A1 (en) | 1997-01-22 |
| MX9602888A (es) | 1997-06-28 |
| JPH0952894A (ja) | 1997-02-25 |
| KR970010770A (ko) | 1997-03-27 |
| SK93796A3 (en) | 1998-06-03 |
| AU6060696A (en) | 1997-01-30 |
| AU712884B2 (en) | 1999-11-18 |
| CZ214896A3 (en) | 1997-02-12 |
| EP0757084A1 (en) | 1997-02-05 |
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