CN1636037A - 基于内酰胺的颜料及其在生产有色塑料或聚合有色颗粒中的应用 - Google Patents
基于内酰胺的颜料及其在生产有色塑料或聚合有色颗粒中的应用 Download PDFInfo
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- 239000000049 pigment Substances 0.000 title claims abstract description 47
- 239000002245 particle Substances 0.000 title claims abstract description 11
- 239000004033 plastic Substances 0.000 title claims abstract description 10
- 229920003023 plastic Polymers 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 150000003951 lactams Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 150000002390 heteroarenes Chemical class 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- -1 methene compound Chemical class 0.000 claims description 10
- 239000011368 organic material Substances 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 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
- 238000001035 drying Methods 0.000 description 4
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 4
- 230000000176 photostabilization Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001136616 Methone Species 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000002012 dioxanes Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 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
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 150000004818 1,2-dichlorobenzenes Chemical class 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- MMBYJYAFFGKUDC-UHFFFAOYSA-N 3-aminoisoindol-1-one Chemical class C1=CC=C2C(N)=NC(=O)C2=C1 MMBYJYAFFGKUDC-UHFFFAOYSA-N 0.000 description 1
- 229940044174 4-phenylenediamine Drugs 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229920000891 common polymer Polymers 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 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
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical class [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/102—The polymethine chain containing an even number of >CH- groups two heterocyclic rings linked carbon-to-carbon
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
本发明涉及新的式(1)颜料，其中R1是氢或C1－C12烷基，R2是氢、－CN、－COO－芳基、－COO－杂芳基、－CONH－芳基或－CONH－杂芳基，且R3是式(II)或(III)杂芳族化合物的基团，或者R2与R3一起形成式(IV)所示基团，其中R4和R5彼此独立地为－CN、－COO－芳基、－COO－杂芳基、－CONH－芳基或－CONH－杂芳基，R6是式(V)、(VI)所示基团，R7是卤素，且R8和R9彼此独立地为C1－C4烷基，还涉及制备这些颜料的方法，以及这些颜料在制备有色塑料或聚合有色颗粒中的应用。
Description
技术领域
本发明涉及新的基于内酰胺的颜料，制备所述颜料的方法，及其在生产有色塑料或聚合有色颗粒中的应用。
背景技术
使用颜料将合成材料例如塑料和聚合有色颗粒进行总体着色的方法是已知的。然而，已经发现，用于这类方法的颜料不能完全满足最高需要，尤其是在耐光度、热稳定性和/或着色力方面不能完全满足最高需要；它们也不能完全覆盖所希望的整个色调调色板。因此，需要能产生耐光的、热稳定且着色性强的着色，尤其是在黄色至红色范围内产生这样的着色，并且表现出良好坚牢度性质的新颜料。
发明内容
现在已惊奇地发现，本发明颜料基本上满足了上述标准。
因此，本发明涉及式(1)颜料
其中
R1是氢或C1-C12烷基，
R2是氢、-CN、-COO-芳基、-COO-杂芳基、-CONH-芳基或-CONH-杂芳基，且
R3是下式所示杂芳族化合物的基团：
或
或者
R2与R3一起形成下式所示基团
或
其中R4和R5彼此独立地为-CN、-COO-芳基、-COO-杂芳基、-CONH-芳基或-CONH-杂芳基，
R6是下式所示基团
或
R7是卤素，且
R8和R9彼此独立地为C1-C4烷基。
作为C1-C12烷基的R1是例如甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基或十二烷基。
在R2、R4和R5的定义内的-COO-芳基和-CONH-芳基中的芳基彼此独立地为例如苯基，所述芳基未取代或者被甲基或卤素取代，尤其是被氯取代。
在R2、R4和R5的定义内的-CONH-杂芳基和-COO-杂芳基中的杂芳基彼此独立地为例如吡咯、呋喃、噻吩、吡啶、咪唑、噻唑、哌嗪或嘧啶。
R1优选为氢或C1-C6烷基。
R1特别优选为氢。
R2优选为氢或-CN。
R2特别优选为氢。
R4优选为氢或-CN。
R4特别优选为氢。
R5优选为氢或-CN。
R5特别优选为氢。
R7优选为氯。
作为C1-C4烷基的R8和R9彼此独立地为甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基或尤其是叔丁基。
本发明还涉及式(1)颜料的制备。
本发明式(1)颜料的制备可例如这样进行：将式(50)化合物
与式(51)化合物反应，
其中X是＝NH或＝O，以形成式(52)化合物
并且任选地，当X是＝NH时，将式(52)化合物与活性亚甲基化合物例如式R4-CH2-R5化合物反应。
本发明还涉及生产有色塑料或聚合有色颗粒的方法，包括将高分子量有机材料与着色有效量的至少一种式(1)颜料彼此混和。
用式(1)颜料给高分子量有机物质着色可例如这样进行：使用轧制机或者混和或研磨装置将这样的颜料与高分子量有机物质混和，结果将颜料溶解或细分散在高分子量材料中。然后使用自身已知的方法，例如压延、压模、挤出、涂布、自旋、倾注或注塑方法将高分子量有机材料与混和的颜料一起加工，结果获得其最终形式的有色材料。颜料的混和还可以在临进行实际加工步骤之前通过例如以下方式来进行：将例如粉末形式的固体颜料与颗粒或粉末形式的高分子量有机材料以及任选的附加组分例如添加剂连续且同时直接进料到挤出机的进料区中，在临加工之前在进料区中混和。然而，一般优选预先将颜料混和到高分子量有机材料内，因为这样可获得着色更均匀的产品。
为了生产非刚性有形制品或为了降低它们的脆性，经常希望在成形之前向高分子量化合物中加入所谓的增塑剂。可用作增塑剂的有例如磷酸、邻苯二甲酸或癸二酸的酯。在本发明方法中，可在掺入着色剂之前或之后向聚合物中掺入增塑剂。此外，为了获得不同色调，除了式(1)颜料以外，还可以向高分子量有机物质中加入任意量的其它颜料或其它着色剂，任选还加入另外的添加剂例如填充剂或干燥剂。
优选给热塑性塑料，尤其是纤维形式的热塑性塑料着色。可依据本发明着色的优选的高分子量有机材料是介电常数≥2.5的极常用聚合物，尤其是聚酯、聚碳酸酯(PC)、聚苯乙烯(PS)、聚异丁烯酸甲酯(PMMA)、聚酰胺、聚乙烯、聚丙烯、苯乙烯/丙烯腈(SAN)和丙烯腈/丁二烯/苯乙烯(ABS)。聚酯和聚酰胺是特别优选的。更尤其优选的是线型芳族聚酯，其可通过将对苯二甲酸与二醇，尤其是乙二醇缩聚来获得，或者是对苯二甲酸与1，4-二(羟基甲基)环己烷的缩合产物，例如聚对苯二甲酸乙二醇酯(PET)或对苯二甲酸丁二醇酯(PBTP)，以及聚碳酸酯，例如由α，α-二甲基-4，4-二羟基-二苯基甲烷与光气获得的聚碳酸酯，或基于聚氯乙烯和基于聚酰胺的聚合物，例如聚酰胺6或聚酰胺6.6。
本发明颜料可给上述材料，尤其是聚酯和聚酰胺材料施加着色性强的色调，并具有非常良好的应用坚牢度性质，尤其是具有良好的耐光性以及良好的热稳定性。
下列实施例是为了举例说明本发明。除非另有说明，在本文中提及的份数是重量份数，百分比是重量百分比。温度是以摄氏度给出的。重量份数与体积份数之间的关系和克数与立方厘米数之间的关系相同。
具体实施方式
实施例1：
将10.2份2-吲哚啉酮(indolinone)与14.3份3-亚氨基异吲哚啉酮盐酸盐以及7.7份乙酸钾在100份二氧杂环己烷和20份冰醋酸中加热至90℃，并在90℃再搅拌4小时。将所沉淀出的反应产物抽滤，用5∶1二氧杂环己烷与冰醋酸的混合物洗涤，然后用水洗涤。干燥后，获得了14.1份式(100)颜料
该颜料能给聚酯总体着上黄色调，并具有非常良好的热稳定性和耐光性。
实施例2：
将4.4份2-氰基苯甲酰胺与4.1份2-吲哚啉酮在25份邻二氯苯中加热至175℃，在该温度下再搅拌6小时。冷却后，沉淀出了4.4份式(100)颜料。
实施例3：
在室温将13.3份2-吲哚啉酮溶解在300份N，N-二甲基乙酰胺中，在室温将所得溶液加到14.5份二亚氨基异吲哚啉(isoindoline)在150份N，N-二甲基乙酰胺内的溶液中。静置48小时后，用水稀释，沉淀出了25份式(101)颜料
将1份所得产物在50份85％乙酸中于回流状态下搅拌4小时。冷却、过滤和干燥后，分离出了0.5份式(100)颜料。
实施例4：
将2.6份在实施例3中制得的式(101)颜料在70份98％乙酸与10份二甲基乙酰胺的混合物中搅拌。加入2份双甲酮后，将该反应混合物加热至80℃，在给温度下再搅拌12小时。用甲醇稀释后，沉淀出了2.7份式(102)颜料
该颜料能给聚酯总体着上红色调。
实施例5-11：
用等当量的表1第二栏所示活性亚甲基化合物代替2.7份实施例4中的双甲酮，并进行如实施例4所述的操作，类似地获得了具有第四栏所示色调的颜料。
表1：
实施例12-21：
用等当量的表2第二栏所示羰基或醛化合物代替实施例1中的14.3份3-亚氨基异吲哚啉酮，并进行如实施例1所述的操作，类似地获得了具有第四栏所示色调的颜料。
表2：
实施例22：
将5.2份得自实施例4的式(102)颜料与1份1，4-苯二胺在500份乙醇与50份乙酸的混合物中于回流状态下搅拌24小时。抽滤出沉淀，使用1∶1二甲基甲酰胺与丙酮的混合物纯化。获得了3.8份式(103)颜料
该颜料能给聚酯总体着上深红色调。
着色实施例：
将1200份聚酯颗粒(PET Arnite D04-300，DSM)在130℃干燥4小时，然后与0.24份式(100)颜料
在“滚柱架”混和装置中以60转/分钟的速度混和15分钟直至均匀。
将该均匀混合物在具有6个加热区的挤出机(双螺杆25mm，得自Collin公司，D-85560 Ebersberg)中以275℃的最高温度挤出，用水冷却，在制粒机(Turb Etuve TE 25，得自MAPAG AG公司，CH-3001 Bern)中制粒，然后在130℃干燥4小时，获得了黄色聚酯颗粒，其具有良好的多种坚牢度性质，尤其是具有非常良好的耐光性和高温耐光性。
Claims (7)
1.式(1)颜料
其中
R1是氢或C1-C12烷基，R2是氢、-CN、-COO-芳基、-COO-杂芳基、-CONH-芳基或-CONH-杂芳基，且R3是下式所示杂芳族化合物的基团：
或者
R2与R3一起形成下式所示基团
其中R4和R5彼此独立地为-CN、-COO-芳基、-COO-杂芳基、-CONH-芳基或-CONH-杂芳基，
R6是下式所示基团
或
R7是卤素，且R8和R9彼此独立地为C1-C4烷基。
2.权利要求1的颜料，其中所述颜料是下式所示颜料：
3.一种制备权利要求1的式(1)颜料的方法，包括将式(50)化合物
与式(51)化合物反应
其中X是＝NH或＝O，
以形成式(52)化合物
并且任选地，当X是＝NH时，将式(52)化合物与活性亚甲基化合物例如式R4-CH2-R5化合物反应。
4.一种生产有色塑料或聚合有色颗粒的方法，包括将高分子量有机材料与着色有效量的至少一种式(1)颜料彼此混和。
5.一种生产有色塑料或聚合有色颗粒的方法，包括将高分子量有机材料与着色有效量的至少一种式(100)-(120)颜料彼此混和。
6.权利要求1的式(1)颜料在制备有色塑料或聚合有色颗粒中的应用。
7.用权利要求1的式(1)颜料着色的塑料或聚合颗粒。
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| CN113773243B (zh) * | 2021-09-01 | 2023-01-06 | 大连理工大学 | 一种有机催化氧化吲哚自缩合制备异靛蓝类化合物的方法 |
| WO2024166734A1 (ja) * | 2023-02-10 | 2024-08-15 | 富士フイルム株式会社 | 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 |
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| IT1093456B (it) | 1978-02-02 | 1985-07-19 | Montedison Spa | Colornti dispersi derivati dalla isatina |
| FI874212A (fi) | 1986-09-29 | 1988-03-30 | Bristol Myers Co | Foerfarande foer framstaellning av 5-aryliden- och 5-alkylidensubstituerade hydantoiner. |
| DE59402281D1 (de) | 1993-06-28 | 1997-05-07 | Bayer Ag | Massefärben von Kunststoffen |
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2003
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- 2003-02-13 JP JP2003569734A patent/JP2005517792A/ja active Pending
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| JP2005517792A (ja) | 2005-06-16 |
| ATE553160T1 (de) | 2012-04-15 |
| US7022177B2 (en) | 2006-04-04 |
| EP1476505A1 (en) | 2004-11-17 |
| WO2003070830A1 (en) | 2003-08-28 |
| US20050056188A1 (en) | 2005-03-17 |
| KR20040096601A (ko) | 2004-11-16 |
| EP1476505B1 (en) | 2012-04-11 |
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