CN101490178A - 异吲哚啉颜料 - Google Patents
异吲哚啉颜料 Download PDFInfo
- Publication number
- CN101490178A CN101490178A CNA2007800270600A CN200780027060A CN101490178A CN 101490178 A CN101490178 A CN 101490178A CN A2007800270600 A CNA2007800270600 A CN A2007800270600A CN 200780027060 A CN200780027060 A CN 200780027060A CN 101490178 A CN101490178 A CN 101490178A
- Authority
- CN
- China
- Prior art keywords
- pigment
- isoindoline
- plastics
- hour
- rough
- 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
- 239000000049 pigment Substances 0.000 title claims abstract description 111
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title claims abstract description 42
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229920001684 low density polyethylene Polymers 0.000 claims abstract description 12
- 239000004702 low-density polyethylene Substances 0.000 claims abstract description 12
- 238000004061 bleaching Methods 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 18
- 229920003023 plastic Polymers 0.000 claims description 18
- 239000004033 plastic Substances 0.000 claims description 18
- 238000002425 crystallisation Methods 0.000 claims description 11
- 239000000725 suspension Substances 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000007669 thermal treatment Methods 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 1
- -1 enanthol Chemical compound 0.000 description 24
- 238000000227 grinding Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000012747 synergistic agent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000002464 physical blending Methods 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 3
- 239000011164 primary particle Substances 0.000 description 3
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- BLDFSDCBQJUWFG-UHFFFAOYSA-N 2-(methylamino)-1,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(NC)C(O)C1=CC=CC=C1 BLDFSDCBQJUWFG-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- RZVCEPSDYHAHLX-UHFFFAOYSA-N 3-iminoisoindol-1-amine Chemical compound C1=CC=C2C(N)=NC(=N)C2=C1 RZVCEPSDYHAHLX-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102100025674 Angiopoietin-related protein 4 Human genes 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 101000693076 Homo sapiens Angiopoietin-related protein 4 Proteins 0.000 description 1
- MKYLOMHWHWEFCT-UHFFFAOYSA-N Manthidine Natural products C1C2=CC=3OCOC=3C=C2C2C3=CC(OC)C(O)CC3N1C2 MKYLOMHWHWEFCT-UHFFFAOYSA-N 0.000 description 1
- SNFRINMTRPQQLE-JQWAAABSSA-N Montanin Chemical compound O[C@H]([C@@]1(CO)O[C@H]1[C@H]1[C@H]2O3)[C@]4(O)C(=O)C(C)=C[C@H]4[C@]11OC3(CCCCCCCCCCC)O[C@@]2(C(C)=C)C[C@H]1C SNFRINMTRPQQLE-JQWAAABSSA-N 0.000 description 1
- SNFRINMTRPQQLE-OFGNMXNXSA-N Montanin Natural products O=C1[C@@]2(O)[C@@H](O)[C@@]3(CO)O[C@H]3[C@@H]3[C@H]4[C@@]5(C(=C)C)O[C@](CCCCCCCCCCC)(O4)O[C@@]3([C@H](C)C5)[C@@H]2C=C1C SNFRINMTRPQQLE-OFGNMXNXSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- QTZPBQMTXNEKRX-UHFFFAOYSA-N Voacristine pseudoindoxyl Natural products N1C2=CC=C(OC)C=C2C(=O)C21CCN(C1)C3C(C(C)O)CC1CC32C(=O)OC QTZPBQMTXNEKRX-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
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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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0096—Purification; Precipitation; Filtration
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Paints Or Removers (AREA)
- Indole Compounds (AREA)
Abstract
本发明公开了通式(I)的异吲哚啉颜料,其中R1为C1-C4烷基;R2为氢或C1-C4烷基。所述异吲哚啉颜料在LDPE中的分散硬度≤10,并且为了调整1/3的标准色度其需要≥5的漂白比。
Description
本发明涉及通式I的异吲哚啉颜料:
其中变量定义如下:
R1为C1-C4烷基;
R2为氢或C1-C4烷基,
其在LDPE中表示易分散性的值≤10,并且为了获得1/3的标准色度,其需要≥5的漂白比(reduction ratio)。
本发明还涉及异吲哚啉颜料的制备和它们用于着色天然和合成来源高分子量有机材料的用途,以及用异吲哚啉颜料着色的塑料。
用于塑料、涂料和印刷墨黄色着色的材料通常是无机颜料如C.I颜料黄34或184;或有机颜料,例如奎诺酞酮颜料如C.I.颜料黄138,异吲哚啉颜料如C.I.颜料黄139或偶氮颜料如C.I.颜料黄74、151或180。最近由于环境因素,对不含重金属和卤素的着色剂,尤其是颜料的需求正急剧增加。
人们对异吲哚啉颜料,尤其是已经熟知大约30年的C.I.颜料黄185的关注程度也因此而增加。然而已经在市场上销售了大约25年的以C.I.颜料黄185为基础的粉末颜料只能用作印刷墨和涂料的颜料。它们的易分散性测试性能使它们不适于在塑料中直接使用,而是不得不首先以复杂的方法转变成制剂。
专利文献中所描述的制备方法不能得到具有直接用于塑料所需性能的C.I.颜料黄185。
例如,DE-A-29 14 086描述了在含水介质中制备该通式I的异吲哚啉颜料的方法,该方法在第一步骤中在25-90℃下在碱性含水介质中使二亚氨基异吲哚啉(II):
通过与式III的氰基乙酰胺缩合:
NC—CH2—CONHR1 III
转化成式IV的半缩合物:
不进行中间分离,在酸化反应混合物之后,在70-90℃的温度下,使该半缩合物与式V的巴比土酸反应:
得到异吲哚啉颜料I。
然后在90-95℃下持续搅拌反应混合物2-3小时后分离出异吲哚啉颜料I。这样获得的异吲哚啉颜料I具有良好的颜色强度,但是由于其在易分散性测试中的值为大约50而不能直接用于塑料中。
DE-A-27 57 982使用这种一锅法制备具有酰胺基或(对-氯)苯基酰胺基(基团R1:氢或(对-氯)苯基)的异吲哚啉颜料。所得的异吲哚啉颜料描述为易于分散在塑料中。为了提高其耐光性和耐候性,推荐在110-140℃下热后处理该含水反应混合物。
根据EP-A-29 007中所述程序制备了该式I的异吲哚啉颜料,同样如DE-A-16 70 748所述,在两个阶段中首先在甲醇中缩合得到半缩合物IV,中间分离,并在稀乙酸中进一步反应。为了制备具有较大遮盖力的颜料的较粗糙形式,还建议随后对反应混合物进行热处理。然而如果如实施例中所述,该转化方法通过在含水乙酸中对粗制颜料加热3小时至120℃来进行,则得到具有很小颜色强度的C.I.颜料黄185。
因此本发明的目标是提供具有整体有利性能特征,尤其是易于在塑料中分散的异吲哚啉颜料。
因此发现了通式I的异吲哚啉颜料:
其中变量定义如下:
R1为C1-C4烷基;
R2为氢或C1-C4烷基,
其在LDPE中表示易分散性的值≤10,并且为了获得1/3的标准色度,其需要≥5的漂白比。
此外,发现了制备异吲哚啉颜料I的方法,其包括使在颜料合成过程中制备的粗制颜料在仅溶合颜料颗粒的试剂存在下进行结晶过程。
最后,发现了异吲哚啉颜料I用于着色天然和合成来源高分子量有机材料的用途。
本发明的异吲哚啉颜料I具有优异的性能特征。此处尤其重要的是C.I.颜料黄185(R1:甲基,R2:氢)。
本发明的异吲哚啉颜料I在非常广泛使用的各种介质中具有非常好的分散性,尤其是在塑料中具有非常好的分散性,并且其在LDPE中表示易分散性的值≤10(根据DIN EN 13900方法测定)。
同时它们还具有优秀的颜色性能,尤其是具有高的颜色强度。根据本发明,由获得1/3的标准色度ST(DIN 53235-1)所需的漂白比定义颜色强度。因此在LDPE中漂白比≥5,优选≥5.5,在PVC中漂白比≥9,优选≥10.5。
本发明的异吲哚啉颜料I的平均初级粒度一般为50-180nm。
本发明的异吲哚啉颜料I的BET比表面积通常是25-40m2/g。
本发明的异吲哚啉颜料I可以包含次要量的未反应半缩合物IV和水解的半缩合物(亚胺官能团水解得到羰基)。这些附属组分的总量通常低于20重量%,尤其是低于15重量%。
本发明的异吲哚啉颜料I可有利地通过同样属于本发明的制备方法获得,其中使在颜料合成过程中制备的粗制颜料在仅溶合颜料颗粒的试剂存在下进行结晶过程。
这里粗制颜料可以通过已知的中间分离半缩合物IV的方法(变化方案A)或通过一锅合成法(变化方案B)合成,优选变化方案B。
在变化方案A中,有机溶剂用作反应介质。用于第一缩合步骤的合适溶剂是质子溶剂,尤其是脂族醇如甲醇、乙醇、异丙醇、异丁醇、戊醇、乙二醇和乙二醇单***,或者是非质子性溶剂如二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮、乙腈、二甲亚砜、二噁烷、环丁砜、二氯苯和硝基苯,优选醇溶剂。第二缩合步骤优选在脂族羧酸如甲酸、乙酸、丙酸、一氯代乙酸和二氯代乙酸中进行。第一阶段反应温度通常为40-120℃,第二阶段反应温度通常为60-180℃。
在变化方案B中,操作在含水介质中进行,优选在水中或水和乙二醇的混合物中。如果需要也可加入表面活性剂。第一缩合步骤通常在10-180℃,尤其在10-90℃和pH>7,尤其是pH为8-11的条件下进行。半缩合物的进一步反应通常在40-150℃,尤其在40-100℃,以及在pH<7,尤其在pH为1-3的条件下进行。通常通过分别加入氨(优选浓氨水溶液)和加入无机酸(优选稀无机酸,优选硫酸、磷酸和盐酸)调节pH。
如果通过在含水悬浮液中热处理粗制颜料来进行本发明的结晶过程,则通过变化方案B制备粗制颜料尤其有利。
在该方法的这种优选变化方案中,粗制颜料的结晶可以在没有中间分离的情况下直接在合成中产生的悬浮液中进行。
如果对异吲哚啉颜料I纯度有特别高的要求,则可以对粗制颜料进行分离,以及如果合适进行提纯,然后也可以干燥和粉碎。
在含水悬浮液中的本发明结晶过程中,将粗制颜料加热1-60小时达到90-180℃范围内的温度T。在此温度T[℃]依赖于处理时间t[小时],并通过以下公式进行计算:
T[℃]=[148-14.4ln(t)]±10
例如,相对于相应待选温度T[℃],给出某些处理时间t[小时]如下:
处理时间t[小时] | 处理温度T[℃] |
2 | 138±10 |
3 | 132±10 |
12 | 112±10 |
36 | 96±10 |
本发明的结晶过程通常在中性或酸性介质中进行,如果使用在合成中制备的反应悬浮液,则酸性介质特别合适,在此阶段其pH小于7。
在此不适于用乙酸调节pH。有机酸通常不如无机酸合适,优选的无机酸为硫酸、磷酸和盐酸。
含水介质与粗制颜料的重量比通常为5:1-50:1,尤其为10:1-40:1。
也可以向含水悬浮液中加入有机溶剂。
此处结果可以偏离温度及通过上述公式计算出的各个处理时间。在极少数情况下所需处理时间可变得更长,但通常是缩短,该值可下降至所计算时间的三分之一。
合适溶剂的实例是醇、醚醇、醚、酮、羧酰胺和羧酸酯,以及它们的混合物。例如,特别可以提及下述化合物:
具有至多10个碳原子的脂族和芳脂族、一元或多元醇,如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、叔丁醇、戊醇、异戊醇、己醇、异己醇、庚醇、辛醇、2-乙基己醇、乙二醇、1,2-丙二醇、1,3-丙二醇、环己醇、甲基环己醇、苄醇和2-苯基乙醇;
单-和二-C2-C3亚烷基二醇单-C1-C4烷基醚,如乙二醇单甲醚、乙二醇单***和乙二醇单丁醚,以及二甘醇单甲醚和二甘醇单***;
具有至多10个碳原子的非环状和环状脂族醚,如二丙醚、二异丙醚、二丁醚、二异丁醚、四氢呋喃、二噁烷、二甘醇二甲醚和二甘醇二***;
具有至多10个碳原子的非环状和环状脂族和芳脂族酮,例如,丙酮、甲乙酮、甲基丙基酮、甲基丁基酮、二乙基酮、甲基异丙基酮、甲基异丁基酮、环戊酮、环己酮、甲基环己酮、苯乙酮和苯基乙基甲酮;
具有至多4个碳原子的脂族羧酸酰胺和脂族羧酸C1-C4烷基酰胺,例如,甲酰胺、N,N-二甲基-和N,N-二乙基甲酰胺、N,N-二甲基-和N,N-二乙基乙酰胺、N,N-二甲基-和N,N-二乙基丙酰胺和N-甲基吡咯烷酮;
具有总共至多12个碳原子的芳族羧酸酯,例如,邻苯二甲酸二甲酯和邻苯二甲酸二乙酯。
此处优选使用在后处理中易于去除的溶剂,如通过水洗提取、与水共沸蒸馏、蒸汽蒸馏或干燥全部混合物的方法去除溶剂。
尤其优选的溶剂是二元醇和它们的单-和二烷基醚。
如果含水结晶介质含有有机溶剂,则水和有机溶剂的重量比通常是99:1-50:50,尤其是95:5-80:20。
结晶过程通过将粗制颜料在含水介质中分散或简单地通过静置而进行。优选是搅拌由粗制颜料和含水介质组成的混合物。
由于结晶过程在含水介质沸程或以上温度进行,适当的是使用密闭装置如压力容器,或在回流下操作。
本发明的异吲哚啉颜料I可以按常规通过过滤、洗涤和干燥进行分离。干燥的产品有利地进行解聚集研磨,例如在旋转磨机、齿轮磨机或喷射磨机中进行。作为替换也可以冷冻干燥或喷雾干燥含水滤饼。
如果需要,在本发明的结晶过程中也可以使用已经用弱碱性研磨助剂提前干磨的粗制颜料。这可以使本发明的异吲哚啉颜料I具有特别窄的初级粒度分布,这些色调更红一些。
合适研磨助剂的实例是弱无机酸的水溶性盐,尤其是碱金属碳酸盐和碱金属碳酸氢盐,例如碳酸钠、碳酸钾、碳酸氢钠和碳酸氢钾。
研磨助剂与粗制颜料的重量比通常是10:1-1:1,优选是4:1-1:1。
合适研磨装置的实例是球磨机、振动磨机、行星式齿轮磨机和超微磨碎机。合适研磨介质的实例是钢丸、硅/铝/锆氧化物珠、玻璃珠和玛瑙珠,它们的直径通常为0.1-5cm。
为了降低风险,可能有利的是该研磨过程在惰性气氛中进行。
优选将材料研磨直到磨制材料的平均初级粒度≤50nm,这样一般需要的时间为1-40小时,尤其需要4-20小时。
然后将磨制材料与水混合以除去研磨助剂、过滤分离、洗涤并从研磨介质中分离出来。在使用钢丸的研磨过程中,为了除去任何可能存在的磨损铁材料,可用盐酸对该磨制材料进行后处理。
为了控制晶体大小,还可能有利的是在颜料增效剂存在下进行结晶过程,所用增效剂的量通常为约0.01-0.1g增效剂/克粗制颜料。如果实施了预粉碎步骤,则还可在该步骤完成之前加入颜料增效剂。
颜料增效剂是其分子结构在某种程度上或全部含有颜料生色团的化合物。在此颜料增效剂的结构不必与要进行结晶的颜料的结构相同。例如,在本发明中不仅可以使用其结构基于异吲哚啉结构的颜料增效剂,也可以使用例如基于奎诺酞酮结构的那些。
特别合适颜料增效剂的实例为从WO-A-02/00643可知的奎诺酞酮衍生物,优选衍生自C.I.颜料黄138并且在萘环上具有一个或多个磺酸官能团的颜料增效剂。
颜料增效剂的存在对本发明的异吲哚啉颜料I在使用介质中的分散性也会产生有利的影响。
通过和常规添加剂接触可以进一步改进本发明的异吲哚啉颜料I的分散性。除了芳族磺酸衍生物如萘磺酸及其盐以及基于松香衍生物的添加剂外,基于天然和合成蜡的添加剂尤其适用于塑料着色。例如可以提及的是基于聚乙烯和聚丙烯(它们也可以被氧化)、基于聚环氧乙烷、基于乙氧基化脂肪醇、基于聚环氧乙烷-聚环氧丙烷嵌段共聚物、基于脂肪酸酯(如褐煤蜡)、基于脂肪酸酰胺和基于乙烯-乙酸乙烯酯共聚物的蜡。
如果使用这些类型的添加剂,它们的量以颜料计通常为2-30重量%。
本发明的异吲哚啉颜料I对于着色天然和合成来源的高分子量有机材料有优良的适用性。
可提及的这些材料的实例为塑料、粉末涂料、油墨、有机调色剂和滤色片这类材料。
本发明的异吲哚啉颜料I对于塑料着色特别重要。
有利的待着色塑料的具体实例是:聚烯烃,如聚乙烯、聚丙烯、聚丁烯、聚异丁烯和聚-4-甲基-1-戊烯,聚烯烃共聚物,如(Basell)、(Dow)和(DuPont),环烯烃共聚物,如(Celanese);聚四氟乙烯(PTFE),乙烯-四氟乙烯共聚物(ETFE);聚偏二氟乙烯(PVDF),聚氯乙烯(PVC),聚偏二氯乙烯,聚乙烯醇,聚乙烯基酯如聚乙酸乙烯酯,乙烯基酯共聚物如乙烯-乙酸乙烯酯共聚物(EVA),聚乙烯基链烷醛如聚乙烯醇缩乙醛和聚乙烯醇缩丁醛(PVB),聚乙烯基酮缩醇,聚酰胺如尼[6]、尼龙[12]和尼龙[6,6](DuPont),聚酰亚胺,聚碳酸酯,聚碳酸酯共聚物,以及聚碳酸酯与丙烯酸-丁二烯-苯乙烯共聚物的物理共混物、与丙烯腈-苯乙烯-丙烯酸酯共聚物的物理共混物、与聚甲基丙烯酸甲酯的物理共混物、与聚丙烯酸丁酯的物理共混物、与聚甲基丙烯酸丁酯的物理共混物、与聚对苯二甲酸丁二醇酯的物理共混物和与聚对苯二甲酸乙二醇酯的物理共混物;其它例子是聚酯,如聚对苯二甲酸乙二醇酯(PET)、聚对苯二甲酸丁二醇酯(PBT)和聚萘二甲酸乙二醇酯(PEN),以上所提及的聚对苯二甲酸亚烷基二醇酯的共聚物、酯交换产物和物理混合物(共混物),聚(甲基)丙烯酸酯、聚丙烯酰胺、聚丙烯腈、聚(甲基)丙烯酸酯/聚偏二氟乙烯共混物、聚氨酯、聚苯乙烯、苯乙烯共聚物如苯乙烯-丁二烯共聚物、苯乙烯-丙烯腈共聚物(SAN)、苯乙烯-甲基丙烯酸乙酯共聚物、苯乙烯-丁二烯-丙烯酸乙酯共聚物、苯乙烯-丙烯腈/甲基丙烯酸酯共聚物、丙烯腈-丁二烯-苯乙烯共聚物(ABS)和甲基丙烯酸酯-丁二烯-苯乙烯共聚物(MBS);聚醚如聚苯醚、聚醚酮、聚砜、聚醚砜,聚二醇如聚甲醛(POM),聚亚芳基亚乙烯基,聚硅氧烷,离聚物,热塑性和热固性聚氨酯,也可以是它们的混合物,重点是聚烯烃,尤其是聚乙烯(LDPE、MDPE、HDPE)和聚氯乙烯。
可以用任何已知方法将本发明的异吲哚啉颜料I掺入塑料中,例如将材料一起挤出(优选使用单-或双螺杆挤出机),辊压、捏和、压缩或研磨,其中可以加工塑料得到塑料模制品,或得到连续的型材,或得到片材、箔、纤维、薄膜和涂层。
为了在低熔点聚合物(例如大多数熟悉的聚烯烃)或那些具有低熔体粘度的聚合物(如增塑的PVC和PVB,以及可吹塑的PET)中获得具有良好颜色强度的均匀着色,使用分别预先制备并且以一种聚合物或聚合物共混物或一种或多种聚烯烃蜡或它们的混合物为基础的颜料制剂同样有利。然而在以聚合物为基础的颜料制剂(“母料”、“配混的材料”)中所用的载体聚合物(共混物)通常与待着色的高分子量合成有机材料相同,特别用于以制备聚烯烃-蜡为基础的颜料制剂的载体材料是均聚和共聚的PE蜡以及均聚和共聚的PP蜡,如A(乙烯均聚物;BASF),Luwax EVA(乙烯-乙酸乙烯酯共聚物;BASF)和PP230(丙烯均聚物;Clariant)。
实施例
A.本发明异吲哚啉颜料I的制备
实施例1
将100g水润湿的C.I.颜料黄185压缩饼(固含量大约50重量%,根据DE-A-2914086中的实施例1制备)在1125ml水中均匀悬浮1小时。然后在2小时内将该悬浮液于具有锚式搅拌器(转速150rpm)的2.4升压力容器(Juchheim)内加热到115℃,并在此温度下搅拌12小时。
在1小时内冷却到60℃后,过滤分离该颜料,并用已加热到60℃的5升水洗涤(排放水的电导率<100μS)。在干燥箱中于70℃下通过空气循环干燥该润湿的压缩饼,并且为了解聚集,在齿轮式磨机(ZM100超离心磨机,Retsch;齿轮级数:12,1.0mm筛,10000rpm)中进行研磨。产率为100%。
实施例2
加入100g乙二醇单丁醚后,将570g根据DE-A-29 14 086的实施例1获得的C.I.颜料黄185的合成悬浮液(颜料含量:5.4重量%)搅拌加热到100℃(回流温度),并在此温度下搅拌12小时。
冷却1小时到70℃后,过滤分离形成的颗粒状材料,用5升加热到60℃的水洗涤(排放水的电导率<50μS)。在干燥箱中于120℃下通过空气循环干燥该润湿的压缩饼,并且为了解聚集,按实施例1的方式进行研磨。产率为90%。
实施例3
将570g根据DE-A-29 14 086的实施例1获得的C.I.颜料黄185的合成悬浮液(颜料含量:5.4重量%)在2小时内于具有锚式搅拌器(转速150rpm)的2.4升压力容器(Juchheim)中加热到130℃,并在此温度下搅拌3小时。
在1小时内冷却到60℃后,过滤分离该颜料,并用已加热到60℃的5升水洗涤(排放水的电导率<50μS)。在干燥箱中于70℃下通过空气循环干燥该润湿的压缩饼,并且为了解聚集,按实施例1的方式进行研磨。产率为100%。
实施例4
将600g根据DE-A-29 14 086中的实施例1获得的C.I.颜料黄185的合成悬浮液(颜料含量:5.1重量%)在2小时内于具有锚式搅拌器(转速150rpm)的1升玻璃反应器(Normag)中加热到95℃,并在此温度下搅拌36小时。
在1小时内冷却到60℃后,过滤分离该颜料,并用已加热到60℃的5升水洗涤(排放水的电导率<50μS)。在干燥箱中于70℃下通过空气循环干燥该润湿的压缩饼,并且为了解聚集,按实施例1的方式进行研磨。产率为100%。
B.本发明颜料在塑料中的测试
为了测试颜料的性能特征,将获得的颜料掺入聚乙烯(LDPE)和软质PVC中。
每种情况下用(1:10)白色漂白在如下制备的磨制片上测定颜色性能和易分散性。
LDPE磨制片:
在150℃(±2℃)的辊温度下该白色LDPE颗粒用作初始进料。一旦形成磨制片,将颜料按份加入并在150℃(±2℃)的辊温度下使用250次辊旋转处理成厚度为0.4mm(±10%)的磨制片。切除约10g后(磨制片1),将剩下的磨制片等分,一旦将两等份互相叠置,在150℃(±2℃)下用220次辊旋转进一步研磨该材料(磨制片2)。
PVC磨制片:
将80g根据DIN 53775-B制备的白色PVC母体混合物(48.7g氯乙烯均聚物,25.1g邻苯二甲酸二异癸酯,1.12g环氧豆油,0.97g稳定剂,0.15g硬脂酸和4.0g二氧化钛)和4.0g各种颜料在混合机中均化。
将得到的混合物在Collin轧制机上,在150℃(±2℃)的辊温度下使用165次辊旋转处理成厚度为0.4mm(±10%)的磨制片。切除约10g后(磨制片1),将剩下的磨制片等分,一旦将两等份互相叠置,在150℃(±2℃)用225次辊旋转进一步研磨该材料(磨制片2)。
样品(磨制片2)的颜色根据DIN 5033(0/0°测量几何)用Teleflash(Optronik)分光光度计进行测量。
漂白比RR根据DIN 53235-1通过使用FIAF方法测定,将待检测样品的色度匹配至1/3标准色度。表中用于色调[°]、彩度C*、明度L*、a*(分别为红色和绿色组分)和b*(分别为蓝色和黄色组分)的CIELAB色度坐标在匹配色度后根据DIN 6174(D65标准光源,10°标准观察者)进行测定。
表示易分散性的值(DH)根据下述公式从测试中获得的各个漂白比进行计算:
其中:RR1=磨制片1的漂白比
RR2=磨制片2的漂白比
获得的测试结果(CIELAB色度坐标和表示易分散性的值)整理如下表。为了比较,在此还列出EP-A-29 007的实施例14中在LDPE中的测试结果。
表
Claims (9)
2.根据权利要求1所述的通式I的异吲哚啉颜料,其中R1为甲基和R2为氢。
3.一种制备权利要求1或2所述的异吲哚啉颜料的方法,其包括使在颜料合成过程中制备的粗制颜料在仅溶合颜料颗粒的试剂存在下进行结晶过程。
4.根据权利要求3所述的方法,其中在90-180℃的温度T下,将在含水悬浮液中的粗制颜料热处理1-60小时,然后将该材料常规分离,其中温度T[℃]用选定的处理时间通过下式从处理时间t[小时]计算:
T[℃]=[148-14.4ln(t)]±10。
5.根据权利要求4所述的方法,其中将含水颜料合成过程中制备的悬浮液进行热处理。
6.根据权利要求1或2所述的通式I的异吲哚啉颜料用于着色天然和合成来源高分子量有机材料的用途。
7.根据权利要求6所述的用途,其中高分子量材料是塑料、粉末涂料、油墨、有机调色剂和滤色片。
8.根据权利要求6所述的用途,其中高分子量材料是塑料。
9.一种塑料,其使用权利要求1或2所述的异吲哚啉颜料着色。
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CN102585542A (zh) * | 2011-12-27 | 2012-07-18 | 百合花集团有限公司 | 一种制备c.i.颜料黄139的方法 |
CN113710758A (zh) * | 2019-04-22 | 2021-11-26 | 东洋油墨Sc控股株式会社 | 包含异吲哚啉化合物的着色组合物及其利用 |
TWI754733B (zh) * | 2017-03-29 | 2022-02-11 | 日商住友化學股份有限公司 | 異吲哚啉色素及其製造方法 |
CN115916909A (zh) * | 2020-07-15 | 2023-04-04 | 东洋油墨Sc控股株式会社 | 颜料组合物、着色组合物、涂料、油墨、油墨组、印刷物、及包装材料 |
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EP2231785B1 (en) * | 2007-12-10 | 2012-01-18 | Basf Se | Isometric isoindoline yellow pigment |
JP2011017838A (ja) * | 2009-07-08 | 2011-01-27 | Ricoh Co Ltd | トナー用着色剤、電子写真用トナー、二成分現像剤、画像形成方法、画像形成装置およびプロセスカートリッジ |
US9102811B2 (en) * | 2011-05-10 | 2015-08-11 | Canon Kabushiki Kaisha | Pigment dispersion, ink composition including pigment dispersion, and color filter yellow resist composition including pigment dispersion |
JP7192639B2 (ja) * | 2019-04-23 | 2022-12-20 | 東洋インキScホールディングス株式会社 | イソインドリン化合物及びその利用 |
JP7017006B1 (ja) | 2020-07-15 | 2022-02-08 | 東洋インキScホールディングス株式会社 | 顔料組成物、着色組成物、塗料、インキ、インキセット、印刷物、及び包装材料 |
JP7105024B1 (ja) | 2021-08-03 | 2022-07-22 | 東洋インキScホールディングス株式会社 | 顔料組成物、着色組成物、塗料、インキ、インキセット、印刷物、及び包装材料 |
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DE1670748A1 (de) | 1966-09-09 | 1973-05-30 | Bayer Ag | Verfahren zur herstellung neuer isoindolinderivate |
DE2757982C2 (de) | 1977-12-24 | 1980-02-21 | Basf Ag, 6700 Ludwigshafen | Verbindungen der Isoindolinreihe und Verfahren zur Herstellung von in den anwendungstechnischen Eigenschaften verbesserten Pigmenten |
DE2800815C2 (de) | 1978-01-10 | 1986-12-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung leicht verteilbarer und deckender Isoindolinpigmentfarbstoffe |
DE2914086B1 (de) * | 1979-04-07 | 1980-09-18 | Basf Ag | Isoindolinfarbstoffe und deren Verwendung |
EP0029007A1 (de) * | 1979-11-09 | 1981-05-20 | Ciba-Geigy Ag | Isoindolinpigmente, Verfahren zu deren Herstellung und Verwendung |
DE3009602A1 (de) * | 1980-03-13 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur formierung von organischen pigmenten |
US4451654A (en) | 1981-03-05 | 1984-05-29 | Basf Aktiengesellschaft | Conditioning of finely divided crude organic pigments |
CH668980A5 (de) * | 1985-07-05 | 1989-02-15 | Basf Ag | Verfahren zur formierung von isoindolinpigmenten. |
JPH09279052A (ja) * | 1996-04-16 | 1997-10-28 | Dainippon Ink & Chem Inc | イソインドリノン系顔料の製造方法および当該顔料を用いた光学素子 |
DE10326631A1 (de) * | 2003-06-11 | 2005-01-05 | Basf Ag | Verwendung von Chinaldin- und Naphthalinderivaten als Kristallisationsmodifikatoren |
-
2007
- 2007-07-11 BR BRPI0714364-8A patent/BRPI0714364A2/pt not_active IP Right Cessation
- 2007-07-11 DE DE502007005064T patent/DE502007005064D1/de active Active
- 2007-07-11 EP EP07787352A patent/EP2044157B1/de not_active Not-in-force
- 2007-07-11 US US12/373,639 patent/US8026361B2/en not_active Expired - Fee Related
- 2007-07-11 JP JP2009519935A patent/JP5447833B2/ja not_active Expired - Fee Related
- 2007-07-11 WO PCT/EP2007/057078 patent/WO2008009597A2/de active Application Filing
- 2007-07-11 CN CN200780027060.0A patent/CN101490178B/zh not_active Expired - Fee Related
- 2007-07-11 AT AT07787352T patent/ATE481454T1/de active
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102585542A (zh) * | 2011-12-27 | 2012-07-18 | 百合花集团有限公司 | 一种制备c.i.颜料黄139的方法 |
TWI754733B (zh) * | 2017-03-29 | 2022-02-11 | 日商住友化學股份有限公司 | 異吲哚啉色素及其製造方法 |
CN113710758A (zh) * | 2019-04-22 | 2021-11-26 | 东洋油墨Sc控股株式会社 | 包含异吲哚啉化合物的着色组合物及其利用 |
CN115916909A (zh) * | 2020-07-15 | 2023-04-04 | 东洋油墨Sc控股株式会社 | 颜料组合物、着色组合物、涂料、油墨、油墨组、印刷物、及包装材料 |
CN115916909B (zh) * | 2020-07-15 | 2024-05-14 | 爱天思株式会社 | 颜料及着色组合物、涂料、油墨、油墨组、印刷物及包装材料 |
Also Published As
Publication number | Publication date |
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JP2009543917A (ja) | 2009-12-10 |
BRPI0714364A2 (pt) | 2013-03-12 |
CN101490178B (zh) | 2014-01-08 |
US20100003612A1 (en) | 2010-01-07 |
WO2008009597A2 (de) | 2008-01-24 |
WO2008009597A3 (de) | 2008-03-20 |
US8026361B2 (en) | 2011-09-27 |
JP5447833B2 (ja) | 2014-03-19 |
ATE481454T1 (de) | 2010-10-15 |
EP2044157A2 (de) | 2009-04-08 |
DE502007005064D1 (de) | 2010-10-28 |
EP2044157B1 (de) | 2010-09-15 |
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