CN100408640C - 蒽醌染料 - Google Patents
蒽醌染料 Download PDFInfo
- Publication number
- CN100408640C CN100408640C CNB038066092A CN03806609A CN100408640C CN 100408640 C CN100408640 C CN 100408640C CN B038066092 A CNB038066092 A CN B038066092A CN 03806609 A CN03806609 A CN 03806609A CN 100408640 C CN100408640 C CN 100408640C
- Authority
- CN
- China
- Prior art keywords
- formula
- compound
- sub
- group
- hydrogen
- 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
Links
- 239000001000 anthraquinone dye Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000004033 plastic Substances 0.000 claims abstract description 11
- 229920003023 plastic Polymers 0.000 claims abstract description 11
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 230000019612 pigmentation Effects 0.000 claims description 9
- 239000011368 organic material Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 238000012644 addition polymerization Methods 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 239000002245 particle Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 19
- -1 (methyl) acryl Chemical group 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004902 Softening Agent Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000000176 photostabilization Effects 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 description 1
- DMPCQDXYSIJPPL-UHFFFAOYSA-N 1-amino-2-chloro-4-[4-(2-hydroxyethyl)anilino]anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(Cl)C=C1NC1=CC=C(CCO)C=C1 DMPCQDXYSIJPPL-UHFFFAOYSA-N 0.000 description 1
- QQOBTPNGSQEDAS-UHFFFAOYSA-N 1-amino-2-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Cl)=C2N QQOBTPNGSQEDAS-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- GJSWNAQTLFQZCJ-UHFFFAOYSA-N 5-chloro-1,4-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C(O)=CC=C2O GJSWNAQTLFQZCJ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000549 coloured material Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
- C09B1/5145—N-aryl derivatives only amino and hydroxy groups
-
- 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
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- C09B1/60—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aliphatic, cycloaliphatic or araliphatic radicals
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Optical Filters (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Luminescent Compositions (AREA)
- Pyrane Compounds (AREA)
Abstract
本发明涉及式(I)化合物，式中R1是式(II)基团，R2是-NH2或式(II)基团，R3和R4彼此独立地是氢、羟基、-NH2或式(II)基团，R5是氢、卤素或-X-(CH2)n-Y，式中X是直连键、-O-或-S-、Y是-OH或-OSO3H，n是一个0～6的数，先决条件是基团R3、R4和R5中至少一个不是氢，涉及其制备工艺，还涉及其在本体着色塑料或聚合物彩色微粒生产方法中的用途。
Description
技术领域
本发明涉及新型蒽醌染料、涉及其制备方法、还涉及其在本体着色塑料或聚合物彩色微粒的生产方法中的用途。
背景技术
染料，尤其蒽醌系列染料，已知可用于本体着色塑料。例如，在美国专利5,367,039中描述了1，4，5，8-四取代的、有可以与乙烯基单体共聚的(甲基)丙烯酰基、因而适用于着色乙烯基聚合物生产的蒽醌。
然而，迄今为止使用的染料，就耐光性和尤其热稳定性而言，并不符合这些最高要求。
因此，目前需要能产生着色力高并显示出耐光性、尤其高温耐光性的着色而且有良好的全面坚牢度性能的新型热稳定染料。
令人惊讶的是，现已发现，按照本发明的染料实质上满足上述基准。
发明内容
因此，本发明涉及式(I)化合物
式中，R1是一个式(II)基团
R2是-NH2或一个式(II)基团，
R3和R4彼此独立地是氢、羟基、-NH2-或一个式(II)基团，
R5是氢、卤素或-X-(CH2)n-Y，
式中X是一个直连键、-O-或-S-，Y是-OH或-OSO3H，且n是0～6的数，
先决条件是基团R3、R4和R5中至少一个不是氢。
式(I)中的R1较好是一个式(II)基团，其中X是一个直连键且n是数2。
也较好的是式(I)化合物，其中R1是一个其Y为-OH的式(II)基团。
特别好的是式(I)化合物，其中R1是一个其X为直连键、n为数2且Y为-OH的式(II)基团。
在式(I)中，R2较好有与R1相同的含义或者是NH2。
式(I)中的R3和R4较好是氢或羟基。
式(I)中的R5较好是氢、氯或-S-(CH2)2-OH。
特别好的按照本发明化合物是式(Ia)～(Ic)化合物
式(I)化合物是可按照本身已知的方法从市售起始化合物得到的。
适用的起始化合物包括例如可以与适当苯胺反应的二氯蒽醌衍生物。
也可以在一种酸介质中在锌和硼酸的存在下使白醌茜与苯胺反应来生成式(I)化合物。
因此，本发明涉及式中基团R2～R4之一是式(II)基团的以上式(I)化合物的制备方法，该方法包含使式(IIIa)、(IIIb)或(IIIc)化合物
式中R2～R5同以上定义，
与式(IV)化合物反应
式中X、Y和n同以上定义。
本发明进一步涉及式中基团R2～R4之一是-NH2的式(I)化合物的制备方法，该方法包含使式(Va)、(Vb)或(Vc)
式中R2～R5同以上定义，
与式(IV)化合物反应
式中X、Y和n同以上定义。
式(IIIa)～(IIIc)和(Va)～(Vc)的蒽醌衍生物以及式(IV)的苯胺可以用本身已知的方法制备。
按照本发明的式(I)化合物尤其适用于本体着色塑料或聚合物彩色微粒的生产。
本发明也涉及本体着色塑料或聚合物彩色微粒的生产方法，该方法包含使一种高分子量有机材料和着色有效量的至少一种式(I)化合物混合。
高分子量有机物质使用式(I)染料着色是诸如通过使用辊炼机、混合装置或研磨装置使这样一种染料与这样的基材混合进行的，从而使该染料溶解或精细地分布于高分子量材料中。然后，混合了染料的高分子量有机材料按照本身已知的方法例如压延、压缩成形、挤塑、涂布、纺丝、灌塑或注塑成形进行加工，其结果，该着色材料获得了其最终形式。该染料的混合也可以在临实施实际加工步骤前进行，例如，同时连续地直接向挤塑机的进料区中进料一种固体例如粉状染料和颗粒状或粉状高分子量有机材料，适当时也可以进料其它组分例如添加剂，这些成分就在临加工前混合。然而，一般地说，较好的是事先将染料混入高分子量有机材料中，因为可以得到更均匀着色的基材。
为了生产非刚性成形物品或为了减少其脆性，往往理想的是在成形之前将所谓增塑剂掺入该高分子量配混物中。例如，作为增塑剂，可以使用磷酸、邻苯二甲酸或癸二酸的酯类。在按照本发明的方法中，该增塑剂可以在该着色剂掺入前或后掺入该聚合物中。为了达到不同的色相，除式(I)染料外，也可以以所希望的数量向该高分子量有机物质中加入其它颜料或其它着色剂，任选地与进一步的添加剂例如填料或催干剂一起加入。
较好的是，尤其呈纤维形式的热塑性塑料的着色。可以按照本发明着色的较好高分子量有机材料非常普遍地是介电常数≥2.5的聚合物、尤其聚酯、聚碳酸酯(PC)、聚苯乙烯(PS)、聚甲基丙烯酸甲酯(PMMA)、聚酰胺、聚乙烯、聚丙烯、苯乙烯/丙烯腈(SAN)或丙烯腈/丁二烯/苯乙烯(ABS)。聚酯和聚酰胺是特别好的。更特别好的是线型芳香族聚酯，后者可以通过对苯二甲酸和二醇尤其乙二醇的缩聚得到，或者是对苯二甲酸与1，4-二(羟甲基)环己烷的缩合产物，例如聚对苯二甲酸乙二醇酯(PET)或聚对苯二甲酸丁二醇酯(PBT)；以及聚碳酸酯，例如从α，α-二甲基-4，4-二羟基二苯甲烷和光气得到的那些，或者聚氯乙烯系聚合物，以及聚酰胺系聚合物例如聚酰胺6或聚酰胺6，6。
由于按照本发明的式(I)化合物含有至少2个NH基，因而，使该染料与单体混合并将其以共聚单体形式直接结合到聚合物骨架中是可能的，先决条件是该单体含有能与NH基的活泼氢原子反应的反应性基团。这样的单体的实例包括环氧化物(环氧树脂)、异氰酸酯(聚氨酯)和羧酰氯(聚酰胺，聚酯)。
因此，本发明也涉及本体着色塑料或聚合物彩色微粒的生产方法，包含使含有至少一个NH反应性基团而且能发生聚合、加聚或缩聚反应的至少一种单体的混合物与至少一种式(I)化合物反应。
按照本发明的染料赋予以上提到的材料、尤其聚酯材料以具有良好实用坚牢度性能、尤其非常良好高温耐光性的高着色力的均匀色相。
按照本发明的染料还可以用于任何种类的涂布应用。
按照本发明的染料也可以容易地与其它染料一起用来产生调合的色相。
按照本发明的式(I)蒽醌染料还适合作为着色剂用于生产滤色器、尤其400～700nm范围内的可见光滤色器，以用于液晶显示器(LCD)或电荷复合器件(CCD)。
依次向一种适用基材例如无定形硅上施用红色、蓝色和绿色着色剂的滤色器生产在GB-A 2 182 165中有描述。该滤色器可以诸如使用包含按照本发明的蒽醌染料的墨、尤其印刷墨涂布，或者可以诸如通过使按照本发明的蒽醌染料与化学上、热力上或光解上可构造的高分子量材料共混来产生。进一步的生产可以诸如类似于EP-A 654 711那样进行，即施用到一种基材例如LCD上，随后光构造和显影。描述滤光器生产的其它文献包括US-A 5 624 467、Displays 14 12，115(1993)和WO 98/45756。
使用按照本发明的蒽醌染料为液晶显示器(LCD)生产的滤色器是以色点透射率高为特色的。
本发明也涉及按照本发明的蒽酯染料作为一种着色剂用于滤色器生产的用途。
具体实施方式
以下实施例用来说明本发明。
实施例1
1，4-二[4-(2-羟基乙基)苯基氨基]-5，8-二羟基蒽酯Ib
将100g 2-(4-氨基苯基)乙醇和20g乙酸钠导入一个实验室反应装置中，在120℃向其中加入20g 1，4-二氯-5，8-二羟基蒽醌。该反应混合物在120℃搅拌4小时，然后倾入1.2L 2N盐酸中。将沉淀物滤出、用水洗涤直至中性、在真空干燥室中干燥。
产率：23.8g(70％)
实施例2
1-[4-(2-羟基乙基)苯基氨基]-3-氯-4-氨基蒽醌Ic
120g 2-(4-氨基苯基)乙醇、17.8g乙酸钾和40g 1-氨基-2，4-二氯蒽醌的混合物在一个实验室反应装置中在180℃搅拌24小时。使反应混合物冷却到室温后，添加大约0.5L甲醇。将沉淀物滤出、用乙醇重结晶、干燥。
产率：50.4g(97％)
实施例3
1-[4-(2-羟基乙基)苯基氨基]-3-(2-羟基乙硫基)-4-氨基蒽醌Ia
50.4g实施例2的1-[4-(2-羟基乙基)苯基氨基]-3-氯-4-氨基蒽醌Ic和100mL二甲基甲酰胺(DMF)的混合物在一个实验室反应装置中加热到80℃。然后添加另外50mL DMF和11g 2-巯基乙醇。然后，在83℃的内部温度，慢慢滴加18.6g 30％氢氧化钠水溶液，混合物在80℃搅拌3小时。冷却到室温后，将沉淀物滤出、用乙醇洗涤、在真空干燥室中干燥。
产率：23.8g(47％)
II.应用例
II.1液晶显示器(LCD)用滤色器生产
在一个含有83.3g锆瓷珠的100mL玻璃容器中，2.8g按照实施例1的蒽醌染料、0.28g Solsperse5000、4.10g Disperbyk
161(分散剂，30％含有对该颜料有亲合力的基团的高分子量嵌段共聚物在乙酸正丁酯/乙酸1-甲氧基-2-丙酯(1∶6)中有溶液，BYK Chemie公司)和14.62g乙酸1-甲氧基-2-丙酯(MPA)使用一台Dispermat在23℃以1000rpm搅拌10分钟、再以3000rpm搅拌180分钟。在添加4.01g丙烯酸酯聚合物粘结剂(35％MPA溶液)之后，在室温下以3000rpm进行30分钟搅拌。除去该瓷珠之后，该分散液用等重量MPA稀释。
使用一台旋涂装置，给一种玻璃基材(Corning型1737-F)涂布所得到的分散液，以1000rpm离心30秒钟。该层在一台热板上于100℃干燥2分钟、于200℃干燥5分钟。所得到的层厚是0.4μm。
同样适用于本体着色塑料的下列蒽醌染料(表1)可以类似于实施例1那样制备：
表1
Claims (12)
1. 一种式(I)化合物
式中，R1是一种式(II)基团
其中X是直连键，Y是-OH或-OSO3H，且n是2，
R2是-NH2或一种式(II)基团，
R3和R4彼此独立地是氢、羟基、-NH2或一种式(II)基团，
R5是氢、卤素或-X-(CH2)n-Y，
其中X是直连键，-O-或-S-，Y是-OH或-OSO3H，且n是0～6的数，
先决条件是，基团R3、R4和R5中至少一个不是氢。
2. 按照权利要求1的式(I)化合物，式中R1是一种其中Y为-OH的式(II)基团。
3. 按照权利要求1的式(I)化合物，式中R3和R4是氢或羟基。
4. 按照权利要求1的式(I)化合物，式中R5是氢、氯或-S-(CH2)2-OH。
5. 按照权利要求1的式(I)化合物，该化合物是式(Ia)～(Ic)中任何一种：
6. 按照权利要求1的式(I)化合物的制备方法，式中基团R2～R4之一是一种式(II)基团，该方法包含使式(IIIa)、(IIIb)或(IIIc)化合物
式中R2～R5同权利要求1中的定义，
与一种式(IV)化合物反应
式中X、Y和n同权利要求1中的定义。
7. 式中基团R2～R4之一是-NH2的按照权利要求1的式(I)化合物的制备方法，包含使式(Va)、(Vb)或(Vc)化合物
式中R2～R5同权利要求1中的定义，
与一种式(IV)化合物反应
式中X、Y和n同权利要求1中的定义。
8. 按照权利要求1～5中任何一项的式(I)化合物在本体着色塑料或聚合物彩色微粒生产中的用途。
9. 本体着色塑料或聚合物彩色微粒的一种生产方法，包含将一种高分子量有机材料与着色有效量的、按照权利要求1～5中任何一项的至少一种式(I)化合物混合。
10. 本体着色塑料或聚合物彩色微粒的一种生产方法，包含使含有至少一个NH反应性基团且能进行聚合、加聚或缩聚反应的至少一种单体的混合物与按照权利要求1～5中任何一项的至少一种式(I)化合物反应。
11. 采用按照权利要求9或10的方法着色的塑料或聚合物彩色微粒。
12. 按照权利要求1的蒽醌染料作为一种着色剂用于滤色器生产的用途。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405226 | 2002-03-22 | ||
| EP02405226.8 | 2002-03-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1643074A CN1643074A (zh) | 2005-07-20 |
| CN100408640C true CN100408640C (zh) | 2008-08-06 |
Family
ID=28051880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB038066092A Expired - Fee Related CN100408640C (zh) | 2002-03-22 | 2003-03-13 | 蒽醌染料 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7456316B2 (zh) |
| EP (1) | EP1487920B1 (zh) |
| JP (1) | JP4503296B2 (zh) |
| KR (1) | KR20050006133A (zh) |
| CN (1) | CN100408640C (zh) |
| AT (1) | ATE545681T1 (zh) |
| AU (1) | AU2003227059A1 (zh) |
| BR (1) | BR0308618B1 (zh) |
| CA (1) | CA2476886C (zh) |
| MX (1) | MXPA04009115A (zh) |
| RU (1) | RU2340642C2 (zh) |
| TW (1) | TWI293322B (zh) |
| WO (1) | WO2003080734A1 (zh) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101384672B (zh) * | 2006-02-17 | 2012-08-08 | 西巴控股有限公司 | 具有提高的对比度的蓝色滤色片 |
| JP6054239B2 (ja) * | 2013-05-07 | 2016-12-27 | 山本化成株式会社 | イソインドリン系化合物およびその製造方法。 |
| WO2015157983A1 (en) * | 2014-04-18 | 2015-10-22 | Dow Global Technologies Llc | Anthraquinone compound used for color filter of lcd |
| CN106458855A (zh) * | 2014-06-17 | 2017-02-22 | 陶氏环球技术有限责任公司 | 用于lcd的彩色滤光片的蒽醌化合物 |
| EP3489217A1 (de) * | 2017-11-24 | 2019-05-29 | LANXESS Deutschland GmbH | Verfahren zur herstellung von phenylaminohydroxyanthrachinonen |
| CN111087831A (zh) * | 2019-12-20 | 2020-05-01 | 南京金浩医药科技有限公司 | 一种新型蒽醌类溶剂蓝染料的制备方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2434765A (en) * | 1944-01-13 | 1948-01-20 | Chem Ind Basel | 1-amino-2-hydroxyalkylthio-4-arylamino-anthraquinones |
| US3413257A (en) * | 1965-07-19 | 1968-11-26 | Ici Ltd | Coloration process |
| US3488195A (en) * | 1966-06-29 | 1970-01-06 | Eastman Kodak Co | Light-sensitive photographic element |
| GB1367933A (en) * | 1971-05-10 | 1974-09-25 | Ici Ltd | Mass colouration of polyesters |
| GB2034358A (en) * | 1978-10-05 | 1980-06-04 | Bayer Ag | Process for dyeing and printing cellulose fibres |
| JPS63268768A (ja) * | 1987-04-27 | 1988-11-07 | Mitsui Toatsu Chem Inc | フイルタ−用緑色色素 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE705034C (de) | 1938-07-31 | 1941-04-13 | Messerschmitt Boelkow Blohm | Rueckstossantrieb mittels der Abgase einer Brennkraftmaschine |
| GB560817A (en) * | 1942-07-15 | 1944-04-21 | Du Pont | Anthraquinone dyestuffs |
| US2487045A (en) * | 1947-02-27 | 1949-11-08 | Eastman Kodak Co | 1,4-diamino-2-halogenoanthraquinone compounds |
| CH325464A (de) | 1953-12-04 | 1957-11-15 | Ciba Geigy | Verfahren zur Herstellung neuer Dioxy-di-(arylamino)-anthrachinone |
| FR1450641A (fr) * | 1964-07-04 | 1966-06-24 | Bayer Ag | Colorants de la série de l'anthraquinone et de la phtalocyanine, et leurs procédés de fabrication |
| CH472464A (de) * | 1964-08-08 | 1969-05-15 | Bayer Ag | Verfahren zur Herstellung von Verbindungen der Anthrachinonreihe |
| US3434792A (en) * | 1965-05-04 | 1969-03-25 | American Cyanamid Co | 1-amino- (and methylamino) 2-bromo-4-(p-(beta - hydroxyethyl) - anilino) - anthraquinone disperse dyes for nylon and polypropylene |
| FR1516828A (fr) | 1965-11-29 | 1968-02-05 | Ici Ltd | Nouveaux colorants de la série de l'anthraquinone et leur procédé de fabrication |
| GB1166998A (en) * | 1965-11-29 | 1969-10-15 | Ici Ltd | Anthraquinone Dyestuffs |
| GB1078092A (en) | 1966-03-08 | 1967-08-02 | Ici Ltd | Anthraquinone dyestuffs |
| GB1152244A (en) * | 1966-07-11 | 1969-05-14 | Ici Ltd | Anthraquinone Dyestuffs |
| FR1530985A (fr) | 1966-07-11 | 1968-06-28 | Ici Ltd | Procédé de fabrication de composés anthraquinoniques |
| US3734934A (en) * | 1970-04-01 | 1973-05-22 | Ciba Geigy Ag | Dispersible {60 -{11 and {62 -substituted anthraquinone dyestuffs containing an -alkyleneocoor group |
| DE2123454A1 (en) | 1971-05-12 | 1972-11-23 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Dyeing of synthetic fibres - using 1,4-bis-(hydroxyanilino) anthraquinones as dispersions in org solvents |
| GB1592966A (en) * | 1977-04-25 | 1981-07-15 | Ici Ltd | Colouration process |
| JPS5790081A (en) * | 1980-11-27 | 1982-06-04 | Canon Inc | Liquid crystal display device |
| GB2101624B (en) | 1981-05-20 | 1984-09-19 | Mitsubishi Chem Ind | Anthraquinone dyes for cellulose-containing fibers and their synthesis |
| JPS5819363A (ja) * | 1981-07-27 | 1983-02-04 | Mitsubishi Chem Ind Ltd | アントラキノン化合物、その製造法及びセルロース含有繊維類用アントラキノン染料 |
| JPS62903A (ja) * | 1985-06-05 | 1987-01-06 | Sumitomo Chem Co Ltd | 近赤外線吸収フイルタ− |
| JPH0657798B2 (ja) * | 1986-12-03 | 1994-08-03 | 三井東圧化学株式会社 | フイルタ−用青色色素 |
| JPS63249693A (ja) * | 1987-04-06 | 1988-10-17 | Sumitomo Chem Co Ltd | 昇華転写型感熱記録用シアン色素 |
| JPH0813930B2 (ja) | 1987-12-28 | 1996-02-14 | 三井東圧化学株式会社 | 近赤外線吸収フィルター用高純度アントラキノン系色素 |
| US4846846A (en) * | 1988-06-20 | 1989-07-11 | Milliken Research Corporation | Process for preparing polyurethane resins colored with anthraquinone colorants and products produced thereby |
| PL362429A1 (en) * | 2000-12-22 | 2004-11-02 | Ciba Specialty Chemicals Holding Inc. | Anthraquinone dyes, preparation thereof and use thereof |
| EP1343840A1 (en) * | 2000-12-22 | 2003-09-17 | Ciba SC Holding AG | Preparation of dyed plastics or polymeric dye particles |
| BR0116401B1 (pt) * | 2000-12-22 | 2014-09-16 | Ciba Specialty Chemicals Hoding Inc | Corante, seu processo de preparação, processo para tintura ou impressão tricromática de materiais fabricados a partir de polímeros naturais e de fibras sintéticas hidrófobas, misturas de corantes tricromáticos, material fabricado de polímero natural ou de material de fibra sintética hidrófoba, de preferência materiais têxteis de poliéster, e processo para produção de combinações de materiais plásticos e de materiais fabricados com polímero natural ou com fibras sintéticas tingidas em tom sobre tom |
-
2003
- 2003-03-13 MX MXPA04009115A patent/MXPA04009115A/es active IP Right Grant
- 2003-03-13 BR BRPI0308618-6B1A patent/BR0308618B1/pt not_active IP Right Cessation
- 2003-03-13 AT AT03744799T patent/ATE545681T1/de active
- 2003-03-13 US US10/508,714 patent/US7456316B2/en not_active Expired - Fee Related
- 2003-03-13 WO PCT/EP2003/002616 patent/WO2003080734A1/en active Application Filing
- 2003-03-13 AU AU2003227059A patent/AU2003227059A1/en not_active Abandoned
- 2003-03-13 KR KR10-2004-7014932A patent/KR20050006133A/ko active IP Right Grant
- 2003-03-13 CA CA2476886A patent/CA2476886C/en not_active Expired - Fee Related
- 2003-03-13 RU RU2004131534/04A patent/RU2340642C2/ru not_active IP Right Cessation
- 2003-03-13 EP EP03744799A patent/EP1487920B1/en not_active Expired - Lifetime
- 2003-03-13 JP JP2003578472A patent/JP4503296B2/ja not_active Expired - Fee Related
- 2003-03-13 CN CNB038066092A patent/CN100408640C/zh not_active Expired - Fee Related
- 2003-04-03 TW TW092107595A patent/TWI293322B/zh not_active IP Right Cessation
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2434765A (en) * | 1944-01-13 | 1948-01-20 | Chem Ind Basel | 1-amino-2-hydroxyalkylthio-4-arylamino-anthraquinones |
| US3413257A (en) * | 1965-07-19 | 1968-11-26 | Ici Ltd | Coloration process |
| US3488195A (en) * | 1966-06-29 | 1970-01-06 | Eastman Kodak Co | Light-sensitive photographic element |
| GB1367933A (en) * | 1971-05-10 | 1974-09-25 | Ici Ltd | Mass colouration of polyesters |
| GB2034358A (en) * | 1978-10-05 | 1980-06-04 | Bayer Ag | Process for dyeing and printing cellulose fibres |
| JPS63268768A (ja) * | 1987-04-27 | 1988-11-07 | Mitsui Toatsu Chem Inc | フイルタ−用緑色色素 |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2004131534A (ru) | 2005-07-10 |
| TW200420673A (en) | 2004-10-16 |
| RU2340642C2 (ru) | 2008-12-10 |
| EP1487920B1 (en) | 2012-02-15 |
| AU2003227059A1 (en) | 2003-10-08 |
| WO2003080734A1 (en) | 2003-10-02 |
| CN1643074A (zh) | 2005-07-20 |
| MXPA04009115A (es) | 2004-12-07 |
| US7456316B2 (en) | 2008-11-25 |
| BR0308618B1 (pt) | 2013-12-03 |
| CA2476886A1 (en) | 2003-10-02 |
| EP1487920A1 (en) | 2004-12-22 |
| CA2476886C (en) | 2011-02-15 |
| BR0308618A (pt) | 2005-02-15 |
| JP4503296B2 (ja) | 2010-07-14 |
| KR20050006133A (ko) | 2005-01-15 |
| US20050150061A1 (en) | 2005-07-14 |
| JP2005520906A (ja) | 2005-07-14 |
| ATE545681T1 (de) | 2012-03-15 |
| TWI293322B (en) | 2008-02-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100408640C (zh) | 蒽醌染料 | |
| TWI261062B (en) | Azo dyes | |
| EP1509573B1 (en) | Anthraquinone-azo dyes | |
| TWI294901B (en) | Anthraquinone dyes | |
| WO2009040318A2 (en) | Dyes for polymer coloration, their preparation and their use | |
| JPH0768459B2 (ja) | 染 料 | |
| KR100207307B1 (ko) | 고분자색소의 제조방법 |
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 | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080806 Termination date: 20180313 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |