JP2009108302A - レッド染料混合物 - Google Patents
レッド染料混合物 Download PDFInfo
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- JP2009108302A JP2009108302A JP2008238573A JP2008238573A JP2009108302A JP 2009108302 A JP2009108302 A JP 2009108302A JP 2008238573 A JP2008238573 A JP 2008238573A JP 2008238573 A JP2008238573 A JP 2008238573A JP 2009108302 A JP2009108302 A JP 2009108302A
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- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 239000001044 red dye Substances 0.000 title claims abstract description 31
- 229920003023 plastic Polymers 0.000 claims abstract description 38
- 239000004033 plastic Substances 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 238000004040 coloring Methods 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- -1 pyrrolidino, piperidino Chemical group 0.000 claims description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 87
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
- 238000004132 cross linking Methods 0.000 claims description 64
- 150000002431 hydrogen Chemical class 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 239000000975 dye Substances 0.000 claims description 50
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 31
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 239000011737 fluorine Substances 0.000 claims description 23
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 20
- 239000001048 orange dye Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 11
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 11
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- 125000003944 tolyl group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
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- 239000000460 chlorine Substances 0.000 claims description 9
- 239000001046 green dye Substances 0.000 claims description 9
- 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 claims description 8
- 230000001588 bifunctional effect Effects 0.000 claims description 8
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- OMJKVIFSWSQTGQ-UHFFFAOYSA-N 6,7-bis(aziridin-1-yl)quinazoline-5,8-dione Chemical compound C1CN1C=1C(=O)C2=NC=NC=C2C(=O)C=1N1CC1 OMJKVIFSWSQTGQ-UHFFFAOYSA-N 0.000 claims description 3
- BTIIGNUPPKUQAP-UHFFFAOYSA-N [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;diperchlorate Chemical compound [O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 BTIIGNUPPKUQAP-UHFFFAOYSA-N 0.000 claims description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
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- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 239000012209 synthetic fiber Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 29
- 0 CC(B*(C=C(C(C(c1c2cccc1)=O)=C1C2=O)N)C=C1O*)(C=C(C(C(c1ccccc11)=O)=C2C1=O)N)C=C2O* Chemical compound CC(B*(C=C(C(C(c1c2cccc1)=O)=C1C2=O)N)C=C1O*)(C=C(C(C(c1ccccc11)=O)=C2C1=O)N)C=C2O* 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000843 powder Substances 0.000 description 16
- 229920000139 polyethylene terephthalate Polymers 0.000 description 14
- 239000005020 polyethylene terephthalate Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
- 229920000515 polycarbonate Polymers 0.000 description 10
- 239000004417 polycarbonate Substances 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000012265 solid product Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 238000013508 migration Methods 0.000 description 8
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- 239000002585 base Substances 0.000 description 7
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- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229920000193 polymethacrylate Polymers 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 229920005601 base polymer Polymers 0.000 description 5
- 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 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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- 238000007792 addition Methods 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
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- 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 4
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- 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 4
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
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- SNMSMWLEXMJNHA-UHFFFAOYSA-N 1-amino-4-hydroxy-1,2-dihydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)CC=C2O SNMSMWLEXMJNHA-UHFFFAOYSA-N 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WFNXYMSIAASORV-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)cyclohexyl]phenol Chemical compound OC1=CC=CC=C1C1(C=2C(=CC=CC=2)O)CCCCC1 WFNXYMSIAASORV-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 1
- CMZKBUOUTPYWEN-UHFFFAOYSA-N 4-amino-2-bromo-1-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(Br)C=C2N CMZKBUOUTPYWEN-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- XRYFCGMTVUVQDN-UHFFFAOYSA-N CC(C)(c(cc1)ccc1Oc(cc(c(C(c1ccccc11)=O)c2C1=O)N)c2O)c(cc1)ccc1Oc(c(O)c1C(c2c3cccc2)=O)cc(N)c1C3=O Chemical compound CC(C)(c(cc1)ccc1Oc(cc(c(C(c1ccccc11)=O)c2C1=O)N)c2O)c(cc1)ccc1Oc(c(O)c1C(c2c3cccc2)=O)cc(N)c1C3=O XRYFCGMTVUVQDN-UHFFFAOYSA-N 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N CC(Nc1ccccc1)=O Chemical compound CC(Nc1ccccc1)=O FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- QEGNUYASOUJEHD-UHFFFAOYSA-N CC1(C)CCCCC1 Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 1
- ZWPWLKXZYNXATK-UHFFFAOYSA-N Cc(cc1)ccc1C(c1ccc(C)cc1)=O Chemical compound Cc(cc1)ccc1C(c1ccc(C)cc1)=O ZWPWLKXZYNXATK-UHFFFAOYSA-N 0.000 description 1
- OWEIAGSMFHSSES-UHFFFAOYSA-N Cc1ccc(C(C(F)(F)F)(C(F)(F)F)c2ccc(C)cc2)cc1 Chemical compound Cc1ccc(C(C(F)(F)F)(C(F)(F)F)c2ccc(C)cc2)cc1 OWEIAGSMFHSSES-UHFFFAOYSA-N 0.000 description 1
- CCKWMYQYXJIDOR-UHFFFAOYSA-N Cc1ccc(C2(CCCC2)c2ccc(C)cc2)cc1 Chemical compound Cc1ccc(C2(CCCC2)c2ccc(C)cc2)cc1 CCKWMYQYXJIDOR-UHFFFAOYSA-N 0.000 description 1
- CUHHAHMLHZVZSN-UHFFFAOYSA-N Cc1ccc(C2(CCCCCC2)c2ccc(C)cc2)cc1 Chemical compound Cc1ccc(C2(CCCCCC2)c2ccc(C)cc2)cc1 CUHHAHMLHZVZSN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229920000426 Microplastic Polymers 0.000 description 1
- XFYQEBBUVNLYBR-UHFFFAOYSA-N O=C(c(cccc1)c1C1=N2)N1c1cccc3cccc2c13 Chemical compound O=C(c(cccc1)c1C1=N2)N1c1cccc3cccc2c13 XFYQEBBUVNLYBR-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QJQYPZZUKLQGGT-UHFFFAOYSA-N methyl hypobromite Chemical compound COBr QJQYPZZUKLQGGT-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/94—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
- C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
-
- 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
- C09B1/005—Di-anthraquinonyl and derivative compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- 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
- C09B1/36—Dyes with acylated amino groups
- C09B1/46—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound
- C09B1/467—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound attached to two or more anthraquinone 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether 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
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Paints Or Removers (AREA)
- Coloring (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200710044743 DE102007044743A1 (de) | 2007-09-18 | 2007-09-18 | Rote Farbstoffmischung |
| DE200810023114 DE102008023114A1 (de) | 2008-05-09 | 2008-05-09 | Rote Farbstoffmischung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009108302A true JP2009108302A (ja) | 2009-05-21 |
| JP2009108302A5 JP2009108302A5 (https=) | 2011-08-04 |
Family
ID=40300249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008238573A Pending JP2009108302A (ja) | 2007-09-18 | 2008-09-17 | レッド染料混合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20090076199A1 (https=) |
| EP (1) | EP2039728B1 (https=) |
| JP (1) | JP2009108302A (https=) |
| CN (1) | CN102964611B (https=) |
| AT (1) | ATE556119T1 (https=) |
| CA (1) | CA2639559A1 (https=) |
| ES (1) | ES2384409T3 (https=) |
| MX (1) | MX2008011953A (https=) |
| RU (1) | RU2008137224A (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111117285A (zh) * | 2019-12-28 | 2020-05-08 | 江苏亚邦染料股份有限公司 | 一种还原蓝4的精制方法 |
| CN111154287A (zh) * | 2019-12-30 | 2020-05-15 | 江苏亚邦染料股份有限公司 | 一种分散红60缩合工艺 |
| CN120988506B (zh) * | 2025-08-15 | 2026-03-31 | 浙江材华科技有限公司 | 一种高耐候可水洗大分子染料 |
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| JPH05271567A (ja) * | 1991-12-12 | 1993-10-19 | Mitsui Toatsu Chem Inc | カラーフィルター用色素およびそれを含有してなるカラーフィルター |
| DE4217973A1 (de) * | 1992-05-30 | 1993-12-02 | Basf Ag | Farbtoner für die Elektrophotographie |
| JPH0673301A (ja) * | 1991-12-13 | 1994-03-15 | Mitsubishi Kasei Hoechst Kk | 分散染料混合物 |
| JPH0680744A (ja) * | 1992-03-31 | 1994-03-22 | Mitsui Toatsu Chem Inc | カラーフィルター用光硬化型樹脂組成物、及び該組成物を用いるカラーフィルターの製造法 |
| JPH06299083A (ja) * | 1993-04-19 | 1994-10-25 | Mitsubishi Kasei Hoechst Kk | 分散染料組成物 |
| JPH09118834A (ja) * | 1995-09-07 | 1997-05-06 | Basf Ag | 染料混合物 |
| DE19623411A1 (de) * | 1996-06-12 | 1997-12-18 | Basf Ag | Farbstoffmischungen |
| JP2002356624A (ja) * | 2001-03-09 | 2002-12-13 | Bayer Ag | 非対称のメチン染料の製造、この染料を含有する混合物、およびこの混合物の使用 |
| JP2004529218A (ja) * | 2001-01-26 | 2004-09-24 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | アゾ染料、それらの製造方法、ならびに着色プラスチックまたはカラーポリマー粒子の製造および疎水性繊維材料の浸染または捺染におけるそれらの使用 |
| CN1597788A (zh) * | 2004-08-13 | 2005-03-23 | 大连理工大学 | 一类红色蒽醌分散染料 |
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| US1589757A (en) * | 1925-06-24 | 1926-06-22 | Kelly Springfield Tire Company | Accelerator for rubber vulcanization |
| CS123304B5 (https=) * | 1965-01-13 | 1966-12-15 | ||
| US4413066A (en) * | 1978-07-05 | 1983-11-01 | Mitsubishi Petrochemical Company, Ltd. | Crosslinkable polyethylene resin compositions |
| US5578419A (en) * | 1991-12-12 | 1996-11-26 | Mitsui Toatsu Chemicals, Incorporated | Dyes for color filters, and photosensitive resist resin composition containing the same |
| DE69317316T2 (de) * | 1992-03-31 | 1998-10-08 | Mitsui Chemicals Inc | Verfahren zur Herstellung eines Farbfilters und fotohärtbare Harzzusammensetzung für dieses Verfahren |
| DE4241116A1 (de) * | 1992-12-07 | 1994-06-09 | Basf Ag | Farbstoffmischungen, enthaltend Azofarbstoffe mit einer Kupplungskomponente aus der Diaminopyridinreihe |
| CN1153189A (zh) * | 1995-09-07 | 1997-07-02 | 巴斯福股份公司 | 含次甲基染料和蒽醌染料的染料混合物 |
| DE69932188T2 (de) * | 1998-11-02 | 2007-06-06 | Orient Chemical Industries, Ltd. | Gefärbte thermoplastische harzzusammensetzung und daraus hergestellte artikel |
| US6759458B2 (en) * | 1999-02-18 | 2004-07-06 | Ticona Gmbh | Thermoplastic molding composition and its use for laser welding |
| CN1286911C (zh) * | 2004-02-24 | 2006-11-29 | 中国乐凯胶片集团公司 | 一种黑色不透光型聚酯薄膜及其制备方法 |
-
2008
- 2008-09-05 ES ES08163756T patent/ES2384409T3/es active Active
- 2008-09-05 AT AT08163756T patent/ATE556119T1/de active
- 2008-09-05 EP EP08163756A patent/EP2039728B1/de active Active
- 2008-09-11 US US12/208,418 patent/US20090076199A1/en not_active Abandoned
- 2008-09-17 RU RU2008137224/04A patent/RU2008137224A/ru unknown
- 2008-09-17 JP JP2008238573A patent/JP2009108302A/ja active Pending
- 2008-09-17 CA CA002639559A patent/CA2639559A1/en not_active Abandoned
- 2008-09-18 MX MX2008011953A patent/MX2008011953A/es unknown
- 2008-09-18 CN CN201210404610.9A patent/CN102964611B/zh active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05271567A (ja) * | 1991-12-12 | 1993-10-19 | Mitsui Toatsu Chem Inc | カラーフィルター用色素およびそれを含有してなるカラーフィルター |
| JPH0673301A (ja) * | 1991-12-13 | 1994-03-15 | Mitsubishi Kasei Hoechst Kk | 分散染料混合物 |
| JPH0680744A (ja) * | 1992-03-31 | 1994-03-22 | Mitsui Toatsu Chem Inc | カラーフィルター用光硬化型樹脂組成物、及び該組成物を用いるカラーフィルターの製造法 |
| DE4217973A1 (de) * | 1992-05-30 | 1993-12-02 | Basf Ag | Farbtoner für die Elektrophotographie |
| JPH06299083A (ja) * | 1993-04-19 | 1994-10-25 | Mitsubishi Kasei Hoechst Kk | 分散染料組成物 |
| JPH09118834A (ja) * | 1995-09-07 | 1997-05-06 | Basf Ag | 染料混合物 |
| DE19623411A1 (de) * | 1996-06-12 | 1997-12-18 | Basf Ag | Farbstoffmischungen |
| JP2004529218A (ja) * | 2001-01-26 | 2004-09-24 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | アゾ染料、それらの製造方法、ならびに着色プラスチックまたはカラーポリマー粒子の製造および疎水性繊維材料の浸染または捺染におけるそれらの使用 |
| JP2002356624A (ja) * | 2001-03-09 | 2002-12-13 | Bayer Ag | 非対称のメチン染料の製造、この染料を含有する混合物、およびこの混合物の使用 |
| CN1597788A (zh) * | 2004-08-13 | 2005-03-23 | 大连理工大学 | 一类红色蒽醌分散染料 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE556119T1 (de) | 2012-05-15 |
| CN102964611A (zh) | 2013-03-13 |
| US20090076199A1 (en) | 2009-03-19 |
| CN102964611B (zh) | 2016-03-09 |
| MX2008011953A (es) | 2009-04-15 |
| EP2039728A2 (de) | 2009-03-25 |
| RU2008137224A (ru) | 2010-03-27 |
| EP2039728A3 (de) | 2010-03-31 |
| ES2384409T3 (es) | 2012-07-04 |
| CA2639559A1 (en) | 2009-03-18 |
| EP2039728B1 (de) | 2012-05-02 |
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