CN102224203A - Dyes for polymer coloration, their preparation and their use - Google Patents
Dyes for polymer coloration, their preparation and their use Download PDFInfo
- Publication number
- CN102224203A CN102224203A CN2009801466171A CN200980146617A CN102224203A CN 102224203 A CN102224203 A CN 102224203A CN 2009801466171 A CN2009801466171 A CN 2009801466171A CN 200980146617 A CN200980146617 A CN 200980146617A CN 102224203 A CN102224203 A CN 102224203A
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- CN
- China
- Prior art keywords
- alkyl
- amino
- aryl
- list
- group
- 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.)
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- 239000000975 dye Substances 0.000 title claims description 75
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 229920000642 polymer Polymers 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
- 125000001769 aryl amino group Chemical group 0.000 claims description 42
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 36
- -1 polyoxy Polymers 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 125000004104 aryloxy group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 22
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 22
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 21
- 229910021529 ammonia Inorganic materials 0.000 claims description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 14
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 14
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 12
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000004986 diarylamino group Chemical group 0.000 claims description 4
- 238000009826 distribution Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 230000000740 bleeding effect Effects 0.000 description 10
- 239000004743 Polypropylene Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- 230000000176 photostabilization Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 229920000098 polyolefin Polymers 0.000 description 7
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000005469 granulation Methods 0.000 description 6
- 230000003179 granulation Effects 0.000 description 6
- 238000001746 injection moulding Methods 0.000 description 6
- 239000004570 mortar (masonry) Substances 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000000227 grinding Methods 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000992 solvent dye Substances 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical class ClC1=NC=NC=N1 HTSVYUUXJSMGQC-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 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 2
- 239000006185 dispersion Substances 0.000 description 2
- 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 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001207 fluorophenyl group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical class CCCCCCS PMBXCGGQNSVESQ-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
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical class CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-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
- RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 CNc1nc(Nc2ccc(-c(c(C(c3c4cccc3)=O)c3C4=O)ccc3Nc3nc(N(*)*)nc(N*)n3)c(C(c3ccccc33)=O)c2C3=O)nc(N(C)*)n1 Chemical compound CNc1nc(Nc2ccc(-c(c(C(c3c4cccc3)=O)c3C4=O)ccc3Nc3nc(N(*)*)nc(N*)n3)c(C(c3ccccc33)=O)c2C3=O)nc(N(C)*)n1 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- BJSKBZUMYQBSOQ-UHFFFAOYSA-N Jeffamine M-600 Chemical compound COCCOCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)N BJSKBZUMYQBSOQ-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide 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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004647 alkyl sulfenyl group Chemical group 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical class CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 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
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [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
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000004079 stearyl 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])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
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000010626 work up procedure 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/005—Di-anthraquinonyl and derivative compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The present invention relates to a compound of formula (I) where X, Y, S and T are each as defined in claim 1, to its preparation and to its use.
Description
(1) technical field
The present invention relates to be used for the painted dyestuff of polymkeric substance, its preparation and uses thereof.
(2) background technology
It is painted that polymkeric substance can use dyestuff to carry out in a different manner.A kind of mode is painted before the spinning of polymkeric substance, for example with a kind of pigment or a kind of dyestuff and this mixed with polymers and with this polymer melted so that this dyestuff is sent in this polymeric matrix.Other method relates to by dyestuff is diffused into from solution or dispersion in the polymkeric substance this polymkeric substance painted (more precisely dyeing), and example is for example to use to the polymer fiber of being made up of for example polyethers, polyacrylonitrile, urethane, Mierocrystalline cellulose or polymeric amide that dispersed dye, cationic dyestuff, matching stain, metallized dye or reactive dyestuffs dye.Use reactive dyestuffs to cause and between dyestuff and matrix, form a covalent linkage, thereby given these dye/tint extra high fastness.Another kind of is dyestuff to be joined in the monomer or oligopolymer of this polymkeric substance before this polymer formation or when it forms with the polymkeric substance method of colouring.Can may cause obtaining the painted of high fastness equally with the dyestuff of this polymer support formation covalent linkage.For this reason, employed dyestuff or more precisely their chromophore must be enough very stable under the polymeric condition.
Commercially available pigment is used for before the spinning of polymkeric substance having given painted polymkeric substance significant high fastness really when painted, but these painted be dim, in other words, lack transparency.The commercially available dyestuff that is used for polymkeric substance is dispersed dye or solvent dye normally, and when being used for to polyolefine producing painted polyolefine when painted, wherein dyestuff often only has hypotonic color fastness.In addition, many in these known dyestuffs have bad photostabilization or low thermostability in polyolefine.A large amount of have in polyolefine that good bleeding fastness, good photostabilization, good thermostability have high saturation ratio and transparency simultaneously and the dyestuff that employed polyolefinic characteristic do not had a negative impact is unknown.
EP 0423068A1, EP 0648817A1 and JP 2003-43680 has described the dianthraquinone dyestuff, and these dyestuffs have satisfied above-mentioned requirements to a certain extent.But mentioned dyestuff can only produce limited tone and limited saturation ratio under the situation that satisfies higher bleeding fastness.
Therefore, for have these cited characteristics and therefore for polyolefinic painted be that useful dyestuff exists a kind of needs.
(3) summary of the invention
Have been found that now by two cyclosubstituted dianthraquinone dyestuffs of triazine and constituted painted useful dyestuff for other matrix of Polyolefin and.They have high stability under application conditions, be easy dissolved in polymkeric substance or be miscible and the painted of highly transparent with fine fastness is provided with the organic solvent that is fit to.
Therefore, the invention provides the dyestuff shown in the formula (I):
Wherein, X, Y, Z and T independently represent a group with formula (1) or formula (2) separately:
Wherein,
R
1To R
3Have identical or different definition separately at a intramolecularly with formula (I), and independent separately representative: Ar; Heteroaryl; Ring-(C3-C8)-alkyl; Heterocyclylalkyl; (C
1-C
35)-alkyl; By one or more by one or more G
1To G
4(the C that replaces of substituting group
1-C
35(the C that)-alkyl interrupts
2-C
35)-alkyl; Interrupted by one or more heteroatomss and by one or more G
1To G
4(the C that replaces of substituting group
2-C
35)-alkyl; Perhaps group with formula (3);
And R
1Also can represent hydrogen; Wherein,
R
4Represent hydrogen, (C
1-C
35)-alkyl, (the C that single oxygen or polyoxy interrupt
1-C
35)-alkyl, aryl, aryl-(C
1-C
35)-alkyl, (C
1-C
35)-alkyl-aryl, aryloxy, (C
1-C
35)-alkoxyl group, monohydroxy-(C
1-C
35)-alkyl or poly-hydroxy-(C
1-C
35)-alkyl; And has identical or different definition at a intramolecularly with formula (I);
V represents one from 1 to 35 numeral;
T represents one from 0.1 to 200 rational number, and has identical or different definition at an intramolecularly with formula (I); And
R
5And R
6Independent separately the hydrogen, (C of representing
1-C
35)-alkyl, (the C that single oxygen or polyoxy interrupt
1-C
35)-alkyl, aryl, aryloxy, (C
1-C
35)-alkoxyl group, monohydroxy-(C
1-C
35)-alkyl or poly-hydroxy-(C
1-C
35)-alkyl;
Wherein, R
5And R
6Has identical or different definition separately at a intramolecularly with formula (I); And work as R
5And R
6When an intramolecularly with formula (I) had different implications, these different definition were that repeating unit stochastic distribution or that have identical definition accordingly is connected to each other;
U represents hydrogen, hydroxyl, amino, list-(C
1-C
35)-alkylamino, N, N-two-(C
1-C
35)-alkylamino, (C
1-C
35)-alkyl, aryl, aryloxy, (C
1-C
35)-alkoxyl group, monohydroxy-(C
1-C
35)-alkyl, poly-hydroxy-(C
1-C
35)-alkyl or (C
1-C
35)-alkyl-aryloxy;
G
1Represent trifluoromethyl; Ring-(C
3-C
8)-alkyl; Aryl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
35)-alkoxyl group; (C
1-C
35)-alkoxy carbonyl; Aryloxy; (C
2-C
35)-acyl group; Aryl carbonyl; (C
2-C
35)-acyloxy; Aryl carbonyl oxygen base; (C
2-C
35)-acyl amino; (C
1-C
35)-alkyl sulfonyl-amino; Arlysulfonylamino; Aryl-amino-carbonyl; Formamyl; N-monocycle-(C
3-C
8)-alkyl-formamyl; N-list-(C
1-C
35)-alkyl-formamyl; N, N-two ring-(C
3-C
8)-alkyl-formamyl; N, N-two-(C
1-C
35)-alkyl-formamyl; Single aryl-the formamyl of N-; N, N-diaryl-formamyl; N-monocycle-(C
3-C
8The single aryl-amino-carbonyl of)-alkyl-N-; N-list-(C
1-C
35The single aryl-amino-carbonyl of)-alkyl-N-; (C
1-C
35)-alkoxy carbonyl; Aryloxycarbonyl; Amino; Monocycle-(C
3-C
8)-alkyl-amino; List-(C
1-C
35)-alkyl-amino; Two ring-(C
3-C
8)-alkyl-amino; Single aryl-amino; Ammonia diaryl base; Monocycle-(C
3-C
8)-alkyl list arylamino; List-(C
1-C
35)-alkyl list aryl-amino; Amino thio-carbonyl-amino; Amino carbonyl amino; Sulfamyl; N-monocycle-(C
3-C
8)-alkyl-sulfamyl; N-list-(C
1-C
35)-alkyl-sulfamyl; N, N-two ring-(C
3-C
8)-alkyl-sulfamyl; N, N-two-(C
1-C
35)-alkyl-sulfamyl; Single aryl-the sulfamyl of N-; N, N-diaryl-sulfamyl; N-monocycle-(C
3-C
8The single ammonia aryl sulfonyl of)-alkyl-N-; N-list-(C
1-C
35The single ammonia aryl sulfonyl of)-alkyl-N-; Amino-sulfonyl amino; (C
1-C
35)-alkyl sulfenyl; Artyl sulfo; (C
1-C
35)-alkyl sulphonyl or aryl sulfonyl;
G
2Representative (C
2-C
35)-alkoxyl group; (C
2-C
35)-alkoxy carbonyl; (C
2-C
35)-acyl group; (C
2-C
35)-acyloxy; (C
2-C
35)-acyl amino; (C
2-C
35)-alkyl sulfonyl-amino; N-list-(C
2-C
35)-alkyl-formamyl; N, N-two-(C
2-C
35)-alkyl-formamyl; N-list-(C
2-C
35The single aryl-amino-carbonyl of)-alkyl-N-; (C
2-C
35)-alkoxy carbonyl; List-(C
2-C
35)-alkyl-amino; List-(C
2-C
35)-alkyl list aryl-amino; N-list-(C
2-C
35)-alkyl-sulfamyl; N, N-two-(C
2-C
35)-alkyl-sulfamyl; N-list-(C
2-C
35The single ammonia aryl sulfonyl of)-alkyl-N-; (C
2-C
35)-alkyl sulfenyl or (C
2-C
35)-alkyl sulphonyl; Wherein alkyl group is interrupted by one or more heteroatomss;
G
3Representative ring-(C
3-C
8)-alkyl; (C
1-C
35)-alkoxyl group; (C
1-C
35)-alkoxy carbonyl; (C
2-C
35)-acyl group; (C
2-C
35)-acyloxy; (C
2-C
35)-acyl amino; (C
1-C
35)-alkyl sulfonyl-amino; N-monocycle-(C
3-C
8)-alkyl-formamyl; N-list-(C
1-C
35)-alkyl-formamyl; N, N-two ring-(C
3-C
8)-alkyl-formamyl; N, N-two-(C
1-C
35)-alkyl-formamyl; N-monocycle-(C
3-C
8The single aryl-amino-carbonyl of)-alkyl-N-; N-list-(C
1-C
35The single aryl-amino-carbonyl of)-alkyl-N-; (C
1-C
35)-alkoxy carbonyl; Monocycle-(C
3-C
8)-alkyl-amino; List-(C
1-C
35)-alkyl-amino; Two ring-(C
3-C
8)-alkyl-amino; Monocycle-(C
3-C
8)-alkyl list arylamino; List-(C
1-C
35)-alkyl list aryl-amino; N-monocycle-(C
3-C
8)-alkyl-sulfamyl; N-list-(C
1-C
35)-alkyl-sulfamyl; N, N-two ring-(C
3-C
8)-alkyl-sulfamyl; N, N-two-(C
1-C
35)-alkyl-sulfamyl; N-monocycle-(C
3-C
8The single ammonia aryl sulfonyl of)-alkyl-N-; N-list-(C
1-C
35The single ammonia aryl sulfonyl of)-alkyl-N-; (C
1-C
35)-alkyl sulfenyl or (C
1-C
35)-alkyl sulphonyl; Wherein alkyl group is by a substituting group G
1Replace:
G
4Represent G
2, wherein alkyl group is replaced by a substituting group G1;
Ar represents a group with formula (5) or formula (6):
Wherein
R
7To R
13Independently has G separately
11Or G
12Definition, perhaps represent a group with formula (7) or formula (8)
Wherein
G
11Represent hydrogen; (C
1-C
35)-alkyl; Trifluoromethyl; Ring-(C
3-C
8)-alkyl; Aryl; Heteroaryl; Heterocyclylalkyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
35)-alkoxyl group; Aryloxy; (C
2-C
35)-acyl group; Ring-(C
3-C
8)-alkyl-carbonyl; Aryl carbonyl; (C
2-C
35)-acyloxy; Aryl carbonyl oxygen base; (C
2-C
35)-acyl amino; (C
1-C
35)-alkyl sulfonyl-amino; Arlysulfonylamino; Aryl-amino-carbonyl; Formamyl; N-monocycle-(C
3-C
8)-alkyl-formamyl; N-list-(C
1-C
35)-alkyl-formamyl; N, N-two ring-(C
3-C
8)-alkyl-formamyl; N, N-two-(C
1-C
35)-alkyl-formamyl; Single aryl-the formamyl of N-; N, N-diaryl-formamyl; N-monocycle-(C
3-C
8The single aryl-amino-carbonyl of)-alkyl-N-; N-list-(C
1-C
35The single aryl-amino-carbonyl of)-alkyl-N-; (C
1-C
35)-alkoxy carbonyl; Aryloxycarbonyl; Amino; Monocycle-(C
3-C
8)-alkyl-amino; List-(C
1-C
35)-alkyl-amino; Two ring-(C
3-C
8)-alkyl-amino; Two-(C
1-C
35)-alkyl-amino; Single aryl-amino; Diaryl-amino; Monocycle-(C
3-C
8)-alkyl list arylamino; List-(C
1-C
35)-alkyl list aryl-amino; Amino thio-carbonyl-amino; Amino carbonyl amino; Sulfamyl; N-monocycle-(C
3-C
8)-alkyl-sulfamyl; N-list-(C
1-C
35)-alkyl-sulfamyl; N, N-two ring-(C
3-C
8)-alkyl-sulfamyl; N, N-two-(C
1-C
35)-alkyl-sulfamyl; Single aryl-the sulfamyl of N-; N, N-diaryl-sulfamyl; N-monocycle-(C
3-C
8The single ammonia aryl sulfonyl of)-alkyl-N-; N-list-(C
1-C
35The single ammonia aryl sulfonyl of)-alkyl-N-; Amino-sulfonyl amino; (C
1-C
35)-alkyl sulfenyl; Artyl sulfo; (C
1-C
35)-alkyl sulphonyl or aryl sulfonyl;
G
12Representative (C
2-C
35)-alkyl; (C
2-C
35)-alkoxyl group; (C
2-C
35)-acyl group; (C
2-C
35)-acyloxy; (C
2-C
35)-acyl amino; (C
2-C
35)-alkyl sulfonyl-amino; N-list-(C
2-C
35)-alkyl-formamyl; N, N-two-(C
2-C
35)-alkyl-formamyl; N-list-(C
2-C
35The single aryl-amino-carbonyl of)-alkyl-N-; (C
2-C
35)-alkoxy carbonyl; List-(C
2-C
35)-alkyl-amino; Two-(C
2-C
35)-alkyl-amino; List-(C
2-C
35)-alkyl list aryl-amino; N-list-(C
2-C
35)-alkyl-sulfamyl; N, N-two-(C
2-C
35)-alkyl-sulfamyl; N-list-(C
2-C
35The single ammonia aryl sulfonyl of)-alkyl-N-; (C
2-C
35)-alkyl sulfenyl or (C
2-C
35)-alkyl sulphonyl; Wherein alkyl group is interrupted by one or more heteroatomss;
R
14To R
16Independent separately representative ring-(C
5-C
6)-alkyl; Heterocyclylalkyl; Heteroaryl; Aryl; (C
1-C
35)-alkyl; (the C that is interrupted by one or more heteroatomss
2-C
35)-alkyl; By one or more substituting group G
13(the C that replaces
1-C
35)-alkyl; Perhaps interrupted and by one or more substituting group G by one or more heteroatomss
13(the C that replaces
2-C
35)-alkyl, and R
14And R
15Can also represent hydrogen separately;
G
13Represent trifluoromethyl; Ring-(C
3-C
8)-alkyl; Aryl; Heteroaryl; Heterocyclylalkyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
35)-alkoxyl group; Aryloxy; (C
2-C
35)-acyl group; Aryl carbonyl; (C
2-C
35)-acyloxy; Aryl carbonyl oxygen base; (C
2-C
35)-acyl amino; Amino; Monocycle-(C
3-C
8)-alkyl-amino; List-(C
1-C
35)-alkyl-amino; Two ring-(C
3-C
8)-alkyl-amino; Two-(C
1-C
35)-alkyl-amino; Single arylamino; Ammonia diaryl base; Monocycle-(C
3-C
8)-alkyl list arylamino; List-(C
1-C
35)-alkyl list arylamino; (C
1-C
35)-alkyl sulfenyl; Artyl sulfo; (C
1-C
35)-alkyl sulphonyl or aryl sulfonyl; And
Aryl is represented a group with formula (9) or formula (10):
Wherein
R
17To R
23The independent separately hydrogen of representing; (C
1-C
12)-alkyl; Ring-(C
3-C
8)-alkyl; Trifluoromethyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
6)-alkoxyl group; (C
2-C
6)-acyl group; (C
2-C
6)-acyl amino; (C
1-C
6)-alkyl sulfonyl-amino; Formamyl; N-list-(C
1-C
6)-alkyl-formamyl; N, N-two-(C
1-C
6)-alkyl-formamyl; Amino; N-list-(C
1-C
6)-alkyl-amino; Two-N, N-(C
1-C
6)-alkyl-amino; Amino carbonyl amino; Sulfamyl; N-list-(C
1-C
6)-alkyl-sulfamyl; Two-N, N-(C
1-C
6)-alkyl-sulfamyl; Amino-sulfonyl amino; (C
1-C
6)-alkyl sulfenyl or (C
1-C
6)-alkyl sulphonyl.
In above-mentioned these definition, alkyl group can be straight chain or side chain, for example methyl, ethyl, n-propyl, sec.-propyl, normal-butyl or isobutyl-also can be hexyl (as n-hexyl), heptyl (as n-heptyl), octyl group (as n-octyl and iso-octyl), nonyl (as n-nonyl), decyl (as positive decyl), dodecyl (as dodecyl), hexadecyl (as n-hexadecyl) or octadecyl (as the Octadecane base) still.Same situation is applicable to alkoxyl group and alkyl sulfenyl.
When alkyl group was interrupted by one or more heteroatomss, heteroatoms was oxygen, sulphur and group-NR
24, R wherein
24Representative (C
1-C
6)-alkyl, monohydroxy-(C
1-C
6)-alkyl, poly-hydroxy-(C
1-C
6)-alkyl, (C
1-C
4)-alkoxyl group-(C
1-C
6)-alkyl, phenoxy group-(C
1-C
6)-alkyl or phenyl.
Cycloalkyl is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, suberyl and ring octyl group especially.
Heterocyclylalkyl has particularly 3 to 8 ring structures, and preferably represents tetramethyleneimine, piperidines, morpholine or piperazine.
Heteroaryl has particularly 5 or 6 ring structures, and is preferably pyridine, pyrimidine, pyridazine, pyrazine, pyrroles, imidazoles, pyrazoles, 1,2,4-thiadiazole, tetrazolium, thiophene, thiazole, isothiazole, 1,3,4-thiadiazole, furans ， oxazole Huo isoxazole.Halogen is selected from fluorine, chlorine or bromine especially.
The dyestuff that the present invention preferably has formula (I) has symmetric replacement form, wherein X, Y, Z and T all be identical or wherein X and Z and Y and T each is identical naturally.
The dyestuff that preferred especially the present invention has formula (I) meets formula (Ia):
Wherein
R
1' and R
2' have identical or different definition separately at a intramolecularly with structural formula (Ia), and independent separately representative: Ar; Ring-(C
5-C
6)-alkyl; Heteroaryl with 5 or 6 ring structures; Heterocyclylalkyl with 5 or 6 ring structures; (C
1-C
18)-alkyl; (the C that is interrupted by one or more heteroatomss
2-C
18)-alkyl; By one or more substituting group G
14(the C that replaces
1-C
18)-alkyl; Interrupted by one or more heteroatomss and by one or more substituting group G
14(the C that replaces
2-C
18)-alkyl; Perhaps group with formula (3a):
And R
1' can also represent hydrogen; Wherein
R
4' represent hydrogen or (C
1-C
35)-alkyl;
W represents 1,2 or 3;
S represents one from 0.1 to 100 rational number, and has identical or different definition at an intramolecularly with structural formula (I);
R
5' and R
6' independent separately hydrogen or the (C of representing
1-C
35)-alkyl;
R wherein
5' and R
6' have identical or different definition separately at a intramolecularly with formula (I); Work as R
5' and R
6' when an intramolecularly with formula (I) had different definition, these different definition were that repeating unit stochastic distribution or that have corresponding identical definition is connected to each other;
U ' represents hydrogen, (C
1-C
35)-alkyl, aryl, aryloxy, (C
1-C
35)-alkoxyl group or (C
1-C
35)-alkyl-aryloxy;
G
14Represent trifluoromethyl; Ring-(C
5-C
6)-alkyl; Aryl; Heteroaryl with 5 or 6 ring structures; Heterocyclylalkyl with 5 or 6 ring structures; Hydroxyl; (C
1-C
18)-alkoxyl group; (C
1-C
18)-alkoxy carbonyl; Aryloxy; (C
2-C
18)-acyl group; (C
2-C
18)-acyloxy or aryl carbonyl;
Ar represent a formula (5a) or (6a) shown in group:
Wherein
R
7' to R
9' the independent separately hydrogen of representing; (C
1-C
18)-alkyl; Trifluoromethyl; Ring-(C
5-C
6)-alkyl; Aryl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
18)-alkoxyl group; Aryloxy; (C
2-C
18)-acyl group; Aryl carbonyl; (C
2-C
18)-acyl amino; (C
1-C
18)-alkyl sulfonyl-amino; Arlysulfonylamino; Aryl-amino-carbonyl; Formamyl; N-list-(C
1-C
18)-alkyl-formamyl; Amino; List-(C
1-C
18)-alkyl-amino; Two-(C
1-C
18)-alkyl-amino; Single aryl-amino; List-(C
1-C
18)-alkyl list aryl-amino; Amino carbonyl amino; Sulfamyl; N-list-(C
1-C
18)-alkyl-sulfamyl; Amino-sulfonyl amino; (C
1-C
18)-alkyl sulfenyl; Artyl sulfo; (C
1-C
18)-alkyl sulphonyl or aryl sulfonyl; And
R
10' to R
13' the independent separately hydrogen, (C represented
1-C
18)-alkyl or a group with formula (7a) or formula (8a):
Wherein, R
14' to R
16' independent separately representative (C
5-C
6)-cycloalkyl; Heterocyclylalkyl with 5 or 6 ring structures; Heteroaryl with 5 or 6 ring structures; Aryl; (C
1-C
18)-alkyl; (the C that is interrupted by one or more heteroatomss
2-C
18)-alkyl; By one or more substituting group G
15(the C that replaces
1-C
18)-alkyl; Perhaps interrupted and by one or more substituting group G by one or more heteroatomss
15(the C that replaces
2-C
18)-alkyl; And R
14' and R
15' can also represent hydrogen separately;
G
15Represent trifluoromethyl; Ring-(C
5-C
6)-alkyl; Aryl; Heteroaryl with 5 or 6 ring structures; Heterocyclylalkyl with 5 or 6 ring structures; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
18)-alkoxyl group; Aryloxy; (C
2-C
18)-acyl group; Aryl carbonyl; Two-(C
1-C
18)-alkyl-amino; Single aryl-amino; Diaryl-amino; List-(C
1-C
18)-alkyl list aryl-amino; (C
1-C
18)-alkyl sulfenyl; Artyl sulfo; (C
1-C
18)-alkyl sulphonyl or aryl sulfonyl; And
Aryl represents one to have formula (9a) or group (10a):
Wherein
R
17' to R
19' the independent separately hydrogen of representing; (C
1-C
12)-alkyl; Trifluoromethyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
6)-alkoxyl group; (C
2-C
6)-acyl group; Amino; (C
2-C
6)-acyl group-amino; List-(C
1-C
6)-alkyl-amino; Sulfamyl; Formamyl or (C
1-C
6)-alkyl sulfenyl; And
R
20' to R
23' independent separately hydrogen or the (C of representing
1-C
6)-alkyl.
Dyestuff shown in the special preferred formula (Ia):
R
1' represent hydrogen or (C
1-C
4)-alkyl; And
R
2' representative (C
1-C
12)-alkyl; By (C
1-C
4)-alkoxyl group, (the C that cyclohexyl or hydroxyl replace
1-C
4)-alkyl; Cyclohexyl; Phenyl; The phenyl that is replaced by fluorine; Group with formula (7a), wherein a R
14' and R
15' separately the representative (C
1-C
4)-alkyl or the group with formula (8a), wherein a R
16' representative (C
1-C
4)-alkyl; Perhaps group with formula (3a), wherein
R
4' represent hydrogen or methyl;
R
5' represent hydrogen or methyl;
U ' represents (C
1-C
10)-alkoxyl group;
V represents 2; And
T represents one from 8 to 12 numeral.
Example with dyestuff of formula (Ia) is the dyestuff with formula (Ia1) to (Ia28):
Further, the dyestuff of particularly preferred the present invention with formula (I) meets formula (Ib):
Wherein
R
3' have identical or different definition and represent Ar at an intramolecularly with formula (Ib); Ring-(C
5-C
6)-alkyl; Heteroaryl with 5 or 6 ring structures; Heterocyclylalkyl with 5 or 6 ring structures; (C
1-C
18)-alkyl; (the C that is interrupted by one or more heteroatomss
2-C
18)-alkyl; By one or more substituting group G
14(the C that replaces
1-C
18)-alkyl; Perhaps interrupted and by one or more substituting group G by one or more heteroatomss
14(the C that replaces
2-C
18)-alkyl; G wherein
14Definition the same; Ar represents one to have formula (5a) or group (6a):
Wherein
R
7' to R
9' the independent separately hydrogen of representing; (C
1-C
18)-alkyl; Trifluoromethyl; Ring-(C
5-C
6)-alkyl; Aryl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
18)-alkoxyl group; Aryloxy; (C
2-C
18)-acyl group; Aryl carbonyl; (C
2-C
18)-acyl amino; (C
1-C
18)-alkyl sulfonyl-amino; Arlysulfonylamino; Aryl-amino-carbonyl; Formamyl; N-list-(C
1-C
18)-alkyl-formamyl; Amino; List-(C
1-C
18)-alkyl-amino; Two-(C
1-C
18)-alkyl-amino; Single aryl-amino; List-(C
1-C
18)-alkyl list aryl-amino; Amino carbonyl amino; Sulfamyl; N-list-(C
1-C
18)-alkyl-sulfamyl; Amino-sulfonyl amino; (C
1-C
18)-alkyl sulfenyl; Artyl sulfo; (C
1-C
18)-alkyl sulphonyl or aryl sulfonyl; And
R
10' to R
13' the independent separately hydrogen, (C represented
1-C
18)-alkyl;
Aryl represents one to have formula (9a) or group (10a):
Wherein
R
17' to R
19' the independent separately hydrogen of representing; (C
1-C
12)-alkyl; Trifluoromethyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
6)-alkoxyl group; (C
2-C
6)-acyl group; Amino; (C
2-C
6)-acyl group-amino; List-(C
1-C
6)-alkyl-amino; Sulfamyl; Formamyl or (C
1-C
6)-alkyl sulfenyl; And
R
20' to R
23' independent separately hydrogen or the (C of representing
1-C
6)-alkyl.
The dyestuff that especially preferably has formula (Ib), R
3' representative (C
1-C
12)-alkyl; By (the C of two Sauerstoffatoms interruptions
1-C
12)-alkyl; By trifluoromethyl, cyano group, chlorine, one or two hydroxyl, phenyl, phenoxy group or (C
1-C
8(the C that)-alkoxy carbonyl replaces
1-C
4)-alkyl; Cyclopentyl; Cyclohexyl; Phenyl; Fluorophenyl or naphthyl.
Example with dyestuff of formula (Ib) is to have the dyestuff of formula (Ib1) to formula (Ib24):
Further, the dyestuff of preferred especially the present invention with formula (I) meets formula (Ic):
Wherein
R
1", R
2" and R
3" have identical or different implication separately at a intramolecularly with formula (Ic), and the independent separately Ar that represents; Ring-(C
5-C
6)-alkyl; Heteroaryl with 5 or 6 ring structures; Heterocyclylalkyl with 5 or 6 ring structures; (C
1-C
18)-alkyl; (the C that is interrupted by one or more heteroatomss
2-C
18)-alkyl; By one or more substituting group G
14(the C that replaces
1-C
18)-alkyl; Interrupted by one or more heteroatomss and by one or more substituting group G
14(the C that replaces
2-C
18)-alkyl; And R
1" can also represent hydrogen; G wherein
14Definition the same;
Ar represents a group with formula (5a) or formula (6a):
Wherein
R
7' to R
9' the independent separately hydrogen of representing; (C
1-C
18)-alkyl; Trifluoromethyl; Ring-(C
5-C
6)-alkyl; Aryl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
18)-alkoxyl group; Aryloxy; (C
2-C
18)-acyl group; Aryl carbonyl; (C
2-C
18)-acyl amino; (C
1-C
18)-alkyl sulfonyl-amino; Arlysulfonylamino; Aryl-amino-carbonyl; Formamyl; N-list-(C
1-C
18)-alkyl-formamyl; Amino; List-(C
1-C
18)-alkyl-amino; Two-(C
1-C
18)-alkyl-amino; Single aryl-amino; List-(C
1-C
18)-alkyl list aryl-amino; Amino carbonyl amino; Sulfamyl; N-list-(C
1-C
18)-alkyl-sulfamyl; Amino-sulfonyl amino; (C
1-C
18)-alkyl sulfenyl; Artyl sulfo; (C
1-C
18)-alkyl sulphonyl or aryl sulfonyl; And
R
10' to R
13' the independent separately hydrogen, (C represented
1-C
18)-alkyl;
Aryl represents one to have formula (9a) or group (10a):
Wherein
R
17' to R
19' the independent separately hydrogen of representing; (C
1-C
12)-alkyl; Trifluoromethyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
6)-alkoxyl group; (C
2-C
6)-acyl group; Amino; (C
2-C
6)-acyl group-amino; List-(C
1-C
6)-alkyl-amino; Sulfamyl; Formamyl or (C
1-C
6)-alkyl sulfenyl; And
R
20' to R
23' independent separately hydrogen or the (C of representing
1-C
6)-alkyl.
The dyestuff that especially preferably has formula (Ic):
R
1" represent hydrogen;
R
2" representative (C
1-C
10)-alkyl; And
R
3" representative (C
1-C
12)-alkyl; By trifluoromethyl, hydroxyl or (C
1-C
4(the C that)-alkoxy carbonyl replaces
1-C
4)-alkyl; Phenyl; Fluorophenyl or naphthyl.
Example with dyestuff of formula (Ic) is to have the dyestuff of formula (Ic1) to formula (Ic10):
Having compound that the dyestuff of formula (I) can be by having formula (II) and one has the compound of formula (III) or has the compound of formula (IV) or the mixture condensation that has the compound of formula (III) and have a compound of formula (IV) obtains
R wherein
1To R
3Definition separately is the same.
This condensation reaction is especially under the temperature condition of 50-200 ℃ (more preferably at 50-180 ℃), in the presence of alkali-free or a kind of alkali (for example pyridine, piperidines, sodium-acetate, salt of wormwood or aluminum chloride) and preferably carry out under anhydrous condition.The preferred a kind of inert solvent of reaction medium that uses or the mixture of inert solvent.Useful solvent comprises chlorinated solvent (for example chlorobenzene or 1,2-dichlorobenzene), alcohol (Pentyl alcohol for example, 1-methoxyl group-2-propyl alcohol, 2-Ethylhexyl Alcohol, 2-methyl-1-butene alcohol, primary isoamyl alcohol, phenylcarbinol, hexalin, glycols and derivative thereof, ethylene glycol diethyl ether for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, the glycol monomethyl isopropyl ether, ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, ethylene glycol, diethylene glycol monoethyl ether, dipropylene glycol), ether (dibutyl ether for example, diisobutyl ether, diisoamyl ether, two n-pentyl ethers), perhaps more polarity or nonpolar inert solvent (ethylbenzene for example, methyl-phenoxide, N, dinethylformamide, N,N-dimethylacetamide, tetramethylene sulfone, N-Methyl pyrrolidone, toluene, 1,2-dimethylbenzene, 1,3-dimethylbenzene, 1,4-dimethylbenzene), the perhaps mixture of above-mentioned solvent.
These reactions can be known from for example DE 3514077 and EP 0710706A2.
As for have formula (I) by the dyestuff of asymmetric replacement, condensation reaction can be carried out continuously, the intermediate product of formation can separate also in reaction process and can not separate.
Compound with formula (II) can be by a compound and 2,4 with formula V, and the reaction of 6-three chloro-1,3,5-triazines obtains.
This condensation reaction is preferably carried out according to above-mentioned reaction with compound of formula (II).
Compound with formula V is to obtain and is commercially available as Colour Index dyestuff C.I. Pigment red 177.Similarly, 2,4,6-three chloro-1,3,5-triazines also are commercially available, for example with the name of Cynuric Chloride.
Similarly, the compound with formula (III) and formula (IV) also is commercially available or makes by known method.The useful compound with formula (III) comprises that particularly the Hensel at the texas,U.S Woodlands steps (Huntsman, TheWoodlands, TX, trade mark USA)
The product of Chu Shouing under one's name.The example of this series products is Jeffamine M-600, Jeffamine M-2005, Jeffamine M-2070, Jeffamine M-1000, Jeffamine D-230, Jeffamine D-400, Jeffamine D-2000, Jeffamine D-4000, Jeffamine HK-511, Jeffamine ED-600, Jeffamine ED-900, Jeffamine ED-2003, Jeffamine ED-2001, Jeffamine EDR-148, Jeffamine EDR-176, JeffamineT-403, Jeffamine M-3000, Jeffamine T-5000, Jeffamine XTJ-435 and Jeffamine XTJ-436.When using multiple these compounds, the dyestuff that the present invention has a formula (I) forms the mixture on the statistical significance.
After synthetic, have formula (I) dyestuff can by filter, extraction or evaporation (and if necessary, drying) separate.Yet they can also not use by further handling (workup).
It is painted that the dyestuff that the present invention has a formula (I) can be directly used in polymkeric substance, perhaps makes them stand one and finally handle (adjustings) and operate so that they are changed into a kind of salable dye preparations.
Final handle (finishing) can set about carrying out by a kind of independent dyestuff with formula (I) or by a kind of mixture of two or more dyestuffs with formula (I) or by one or more multiple mixtures with the dyestuff of formula (I) and dyestuff of other dye class (for example pigment or solvent dye), optional pass through assisting of auxiliary agent (for example surface-modifying agent and dispersion agent), by disperseing, suspend or be dissolved in a kind of liquid or solid solid support material, and optional a kind of desirable colour intensity and a kind of desirable tone of also being normalized to, and the optional dye preparations that will therefore obtain carries out drying.
Comprise and have formula the goods of dyestuff of (I) can further comprise in order to adjust the auxiliary agent of viscosity/flowability.
This useful analog assistant for example is being described among the US 6,605,126.Preferred example is ethylene glycol, propylene glycol, polyether polyol, polyester polyol, lactone and carbonic ether.
Therefore the present invention also provides dye preparations, these dye preparations to comprise one or more dyestuffs with formula (I) and has also had one or more to be used to adjust the auxiliary agent of viscosity/flowability.
These dye preparations preferably comprise value for by weight 5% to 100% one or more have the compound of formula (I) and value for by weight 0% to 95% one or more be used to adjust the auxiliary agent of viscosity/flowability, all based on this dye preparations.
Having the present invention further provides the compound with formula (I) is used for the painted purposes of polymkeric substance.
A kind of possible program is to have compound and this mixed with polymers of formula (I).
In addition, the compound of the present invention with formula (I) can also use with the form of masterbatch.The dyestuff enriched material that masterbatch is made up of solid support material and tinting material, tinting material is to exist than concentration higher in the final use and solid support material is introduced into and forms so that carrier and masterbatch and have material to be colored to have consistency.Employed solid support material can be a polymkeric substance, for example polyolefine, polyvinyl chloride, polyester, polymeric amide, polycarbonate or polystyrene.Preferred polymkeric substance is polyolefine (for example polyethylene or polypropylene) and polyolefinic multipolymer.The useful carrier material further comprises paraffin oil and polyoxyethylene glycol.The feature of these dyestuff masterbatch particularly in, they comprise value and are one or more solid support materials of 40% to 95% by weight for one or more the present invention of 5% to 60% by weight have the compound of formula (I) and value.
Compound with formula (I) has the advantage aspect bleeding/gamut fastness in painted before polyolefinic spinning, particularly compare with commercially available solvent dye.These advantages are significant especially in polypropylene, polypropylene copolymer and polypropylene blend painted.In order to realize the good bleeding fastness of the polymkeric substance that this is painted, preferred the compound that uses with formula (I) with enough high molecular weights.
(4) embodiment
Example hereinafter is used to illustrate the present invention, but not the present invention is limited to these examples.Unless otherwise indicated, otherwise umber and per-cent all be by weight.The relation of parts by weight and volume parts is as the relation of kilogram and liter.
Embodiment 1
A) 20.0 part 1, the 4-dioxane, the mixture of 13.5 parts of compounds with formula V and 55.0 parts of Cynuric Chlorides (from Fluka) stirred 10 hours at 100 ℃, and cooling is also filtered, separate the precipitation obtain with 2-propyl alcohol purifying, and drying obtain the having formula compound of (II).
B) 10.0 parts of compounds with formula (II), 15.0 part 2 ethyl hexylamine (from Merck) and 75.0 part 1, the mixture of 4-dioxane refluxes under the boiling temperature of mixture and stirred 7 hours, the cooling and and methanol mixed, separate the precipitation obtain and be washed with water to neutrality, drying obtains the having formula compound of (Ia3).
C) dyestuff that makes of 0.9g step b) is pulverized in mortar, adds altogether in the 2kg polypropylene granules (from the Moplen RP340R of Basell).This mixture is extruded and granulation in a twin screw extruder (from the ZSE 18HP-D40 of Leistritz) then grinding evenly in a roll crusher.The pellet that is obtained can be handled in an injection molding machine (from 420 ℃ of 1000-100 of Arburg) to form the yellow transparent sample substrate.This dyestuff has high bleeding fastness (according to prEN14469-4), high to hot colour stability (according to EN12877-2) and high photostabilization (according to EN ISO 105-B01).
Embodiment 2
A) 8.0 parts of compounds with formula (II), 8.3 part 3 methoxypropyl amine (from Aldrich) and 70.0 part 1, the mixture of 4-dioxane refluxes under the boiling temperature of mixture and stirred 8 hours, cooling also mixes with water, separate the precipitation methyl alcohol purifying obtain, drying obtains the having formula compound of (Ia1).
B) dyestuff that makes of 0.8g step a) is pulverized in mortar, adds altogether in the 2kg polypropylene granules (from the Moplen RP340R of Basell).This mixture is extruded and granulation in a twin screw extruder (from the ZSE 18HP-D40 of Leistritz) then grinding evenly in a roll crusher.The pellet that is obtained can be handled in an injection molding machine (from 420 ℃ of 1000-100 of Arburg) to form the yellow transparent sample substrate.This dyestuff has high bleeding fastness (according to prEN14469-4), extraordinary to hot colour stability (according to EN12877-2) and extraordinary photostabilization (according to EN ISO 105-B01).
Embodiment 3
A) 10.0 parts of compounds with formula (II), 25.0 parts of Dodecyl Mercaptans (from Aldrich), 7.8 parts of Anhydrous potassium carbonates and 75.0 part 1, the mixture of 4-dioxane refluxes under the boiling temperature of mixture and stirred 10 hours, cooling and and methanol mixed.The sedimentation and filtration that generates, blunge to neutrality and use the methyl alcohol purifying then, and drying obtains the compound of formula (Ib14).
B) dyestuff that makes of 1.0g step a) is pulverized in mortar, adds altogether in the 2kg polypropylene granules (from the Moplen RP340R of Basell).This mixture is extruded and granulation in a twin screw extruder (from the ZSE 18HP-D40 of Leistritz) then grinding evenly in a roll crusher.The pellet that is obtained can be handled in an injection molding machine (from 420 ℃ of 1000-100 of Arburg) to form the yellow transparent sample substrate.This dyestuff has high bleeding fastness (according to prEN14469-4), high to hot colour stability (according to EN12877-2) and high photostabilization (according to EN ISO 105-B01).
Embodiment 4
A) 7.5 parts of compounds with formula (II), 6.8 parts of hexylmercaptans (from Aldrich), the mixture of 7.7 parts of Anhydrous potassium carbonates and 75.0 parts of tetramethylene sulfone stirred 10 hours at 125-140 ℃, cooling and and methanol mixed.The sedimentation and filtration that generates, blunge to neutrality and use the methyl alcohol purifying then, and drying obtains the compound of formula (Ib10).
B) dyestuff that makes of 1.0g step a) is pulverized in mortar, adds altogether in the 2kg polypropylene granules (from the Moplen RP340R of Basell).This mixture is extruded and granulation in a twin screw extruder (from the ZSE 18HP-D40 of Leistritz) then grinding evenly in a roll crusher.The pellet that is obtained can be handled in an injection molding machine (from 420 ℃ of 1000-100 of Arburg) to form the yellow transparent sample substrate.This dyestuff has high bleeding fastness (according to prEN14469-4), high to hot colour stability (according to EN12877-2) and high photostabilization (according to EN ISO 105-B01).
Embodiment 5
A) 10.0 parts of compounds with formula (II), 22.7 parts of amino dodecanes (from Aldrich) and 75.0 part 1, the mixture of 4-dioxane reflux under the boiling temperature of mixture and stirred 2 hours, cooling and and methanol mixed.Separate the precipitation obtain and blunge to neutrality and use the methyl alcohol purifying then, and drying obtains the compound of formula (Ia27).
B) dyestuff that makes of 1.0g step a) is pulverized in mortar, is added to altogether in the 2kg polypropylene granules (from the Moplen RP340R of Basell).This mixture is extruded and granulation in a twin screw extruder (from the ZSE 18HP-D40 of Leistritz) then grinding evenly in a roll crusher.The pellet that is obtained can be handled in an injection molding machine (from 420 ℃ of 1000-100 of Arburg) to form the yellow transparent sample substrate.This dyestuff has high bleeding fastness (according to prEN14469-4), high to hot colour stability (according to EN12877-2) and high photostabilization (according to EN ISO 105-B01).
Embodiment 6
A) 7.5 parts of compounds with formula (II), 9.6 parts of butylamine (from Aldrich) and 100 part 1, the mixture of 4-dioxane stirred 7 hours under superatmospheric pressure (1.3bar) condition at 100 ℃, cooling and and methanol mixed.The precipitation that obtains is blunged to neutrality and is used the methyl alcohol purifying then, and drying obtains the compound of formula (Ia2).
B) dyestuff that makes of 1.0g step a) is pulverized in mortar, is added to altogether in the 2kg polypropylene granules (from the Moplen RP340R of Basell).This mixture grinds in a roll crusher evenly, extrudes and granulation in a twin screw extruder (from the ZSE 18HP-D40 of Leistritz) then.The pellet that is obtained can be handled in an injection molding machine (from 420 ℃ of 1000-100 of Arburg) to form the yellow transparent sample substrate.This dyestuff has high bleeding fastness (according to prEN14469-4), high to hot colour stability (according to EN12877-2) and high photostabilization (according to EN ISO 105-B01).
Claims (7)
1. dyestuff with formula (I)
Wherein, X, Y, Z and T independently represent a group with formula (1) or formula (2) separately:
Wherein,
R
1To R
3Have identical or different definition separately at a intramolecularly with formula (I), and independent separately representative: Ar; Heteroaryl; Ring-(C3-C8)-alkyl; Heterocyclylalkyl; (C
1-C
35)-alkyl; By one or more by one or more G
1To G
4(the C that replaces of substituting group
1-C
35(the C that)-alkyl interrupts
2-C
35)-alkyl; Interrupted by one or more heteroatomss and by one or more G
1To G
4(the C that replaces of substituting group
2-C
35)-alkyl; Perhaps group with formula (3);
And R
1Also can represent hydrogen; Wherein,
R
4Represent hydrogen, (C
1-C
35)-alkyl, (the C that single oxygen or polyoxy interrupt
1-C
35)-alkyl, aryl, aryl-(C
1-C
35)-alkyl, (C
1-C
35)-alkyl-aryl, aryloxy, (C
1-C
35)-alkoxyl group, monohydroxy-(C
1-C
35)-alkyl or poly-hydroxy-(C
1-C
35)-alkyl; And has identical or different definition at a intramolecularly with formula (I);
V represents one from 1 to 35 numeral;
T represents one from 0.1 to 200 rational number, and has identical or different definition at an intramolecularly with formula (I); And
R
5And R
6Independent separately the hydrogen, (C of representing
1-C
35)-alkyl, (the C that single oxygen or polyoxy interrupt
1-C
35)-alkyl, aryl, aryloxy, (C
1-C
35)-alkoxyl group, monohydroxy-(C
1-C
35)-alkyl or poly-hydroxy-(C
1-C
35)-alkyl;
Wherein, R
5And R
6Has identical or different definition separately at a intramolecularly with formula (I); And work as R
5And R
6When an intramolecularly with formula (I) had different implications, these different definition were that repeating unit stochastic distribution or that have identical definition accordingly is connected to each other;
U represents hydrogen, hydroxyl, amino, list-(C
1-C
35)-alkylamino, N, N-two-(C
1-C
35)-alkylamino, (C
1-C
35)-alkyl, aryl, aryloxy, (C
1-C
35)-alkoxyl group, monohydroxy-(C
1-C
35)-alkyl, poly-hydroxy-(C
1-C
35)-alkyl or (C
1-C
35)-alkyl-aryloxy;
G
1Represent trifluoromethyl; Ring-(C
3-C
8)-alkyl; Aryl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
35)-alkoxyl group; (C
1-C
35)-alkoxy carbonyl; Aryloxy; (C
2-C
35)-acyl group; Aryl carbonyl; (C
2-C
35)-acyloxy; Aryl carbonyl oxygen base; (C
2-C
35)-acyl amino; (C
1-C
35)-alkyl sulfonyl-amino; Arlysulfonylamino; Aryl-amino-carbonyl; Formamyl; N-monocycle-(C
3-C
8)-alkyl-formamyl; N-list-(C
1-C
35)-alkyl-formamyl; N, N-two ring-(C
3-C
8)-alkyl-formamyl; N, N-two-(C
1-C
35)-alkyl-formamyl; Single aryl-the formamyl of N-; N, N-diaryl-formamyl; N-monocycle-(C
3-C
8The single aryl-amino-carbonyl of)-alkyl-N-; N-list-(C
1-C
35The single aryl-amino-carbonyl of)-alkyl-N-; (C
1-C
35)-alkoxy carbonyl; Aryloxycarbonyl; Amino; Monocycle-(C
3-C
8)-alkyl-amino; List-(C
1-C
35)-alkyl-amino; Two ring-(C
3-C
8)-alkyl-amino; Single aryl-amino; Ammonia diaryl base; Monocycle-(C
3-C
8)-alkyl list arylamino; List-(C
1-C
35)-alkyl list aryl-amino; Amino thio-carbonyl-amino; Amino carbonyl amino; Sulfamyl; N-monocycle-(C
3-C
8)-alkyl-sulfamyl; N-list-(C
1-C
35)-alkyl-sulfamyl; N, N-two ring-(C
3-C
8)-alkyl-sulfamyl; N, N-two-(C
1-C
35)-alkyl-sulfamyl; Single aryl-the sulfamyl of N-; N, N-diaryl-sulfamyl; N-monocycle-(C
3-C
8The single ammonia aryl sulfonyl of)-alkyl-N-; N-list-(C
1-C
35The single ammonia aryl sulfonyl of)-alkyl-N-; Amino-sulfonyl amino; (C
1-C
35)-alkyl sulfenyl; Artyl sulfo; (C
1-C
35)-alkyl sulphonyl or aryl sulfonyl;
G
2Representative (C
2-C
35)-alkoxyl group; (C
2-C
35)-alkoxy carbonyl; (C
2-C
35)-acyl group; (C
2-C
35)-acyloxy; (C
2-C
35)-acyl amino; (C
2-C
35)-alkyl sulfonyl-amino; N-list-(C
2-C
35)-alkyl-formamyl; N, N-two-(C
2-C
35)-alkyl-formamyl; N-list-(C
2-C
35The single aryl-amino-carbonyl of)-alkyl-N-; (C
2-C
35)-alkoxy carbonyl; List-(C
2-C
35)-alkyl-amino; List-(C
2-C
35)-alkyl list aryl-amino; N-list-(C
2-C
35)-alkyl-sulfamyl; N, N-two-(C
2-C
35)-alkyl-sulfamyl; N-list-(C
2-C
35The single ammonia aryl sulfonyl of)-alkyl-N-; (C
2-C
35)-alkyl sulfenyl or (C
2-C
35)-alkyl sulphonyl; Wherein alkyl group is interrupted by one or more heteroatomss;
G
3Representative ring-(C
3-C
8)-alkyl; (C
1-C
35)-alkoxyl group; (C
1-C
35)-alkoxy carbonyl; (C
2-C
35)-acyl group; (C
2-C
35)-acyloxy; (C
2-C
35)-acyl amino; (C
1-C
35)-alkyl sulfonyl-amino; N-monocycle-(C
3-C
8)-alkyl-formamyl; N-list-(C
1-C
35)-alkyl-formamyl; N, N-two ring-(C
3-C
8)-alkyl-formamyl; N, N-two-(C
1-C
35)-alkyl-formamyl; N-monocycle-(C
3-C
8The single aryl-amino-carbonyl of)-alkyl-N-; N-list-(C
1-C
35The single aryl-amino-carbonyl of)-alkyl-N-; (C
1-C
35)-alkoxy carbonyl; Monocycle-(C
3-C
8)-alkyl-amino; List-(C
1-C
35)-alkyl-amino; Two ring-(C
3-C
8)-alkyl-amino; Monocycle-(C
3-C
8)-alkyl list arylamino; List-(C
1-C
35)-alkyl list aryl-amino; N-monocycle-(C
3-C
8)-alkyl-sulfamyl; N-list-(C
1-C
35)-alkyl-sulfamyl; N, N-two ring-(C
3-C
8)-alkyl-sulfamyl; N, N-two-(C
1-C
35)-alkyl-sulfamyl; N-monocycle-(C
3-C
8The single ammonia aryl sulfonyl of)-alkyl-N-; N-list-(C
1-C
35The single ammonia aryl sulfonyl of)-alkyl-N-; (C
1-C
35)-alkyl sulfenyl or (C
1-C
35)-alkyl sulphonyl; Wherein alkyl group is by a substituting group G
1Replace:
G
4Represent G
2, wherein alkyl group is replaced by a substituting group G1;
Ar represents a group with formula (5) or formula (6)
Wherein
R
7To R
13Independently has G separately
11Or G
12Definition, perhaps represent a group with formula (7) or formula (8)
Wherein
G
11Represent hydrogen; (C
1-C
35)-alkyl; Trifluoromethyl; Ring-(C
3-C
8)-alkyl; Aryl; Heteroaryl; Heterocyclylalkyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
35)-alkoxyl group; Aryloxy; (C
2-C
35)-acyl group; Ring-(C
3-C
8)-alkyl-carbonyl; Aryl carbonyl; (C
2-C
35)-acyloxy; Aryl carbonyl oxygen base; (C
2-C
35)-acyl amino; (C
1-C
35)-alkyl sulfonyl-amino; Arlysulfonylamino; Aryl-amino-carbonyl; Formamyl; N-monocycle-(C
3-C
8)-alkyl-formamyl; N-list-(C
1-C
35)-alkyl-formamyl; N, N-two ring-(C
3-C
8)-alkyl-formamyl; N, N-two-(C
1-C
35)-alkyl-formamyl; Single aryl-the formamyl of N-; N, N-diaryl-formamyl; N-monocycle-(C
3-C
8The single aryl-amino-carbonyl of)-alkyl-N-; N-list-(C
1-C
35The single aryl-amino-carbonyl of)-alkyl-N-; (C
1-C
35)-alkoxy carbonyl; Aryloxycarbonyl; Amino; Monocycle-(C
3-C
8)-alkyl-amino; List-(C
1-C
35)-alkyl-amino; Two ring-(C
3-C
8)-alkyl-amino; Two-(C
1-C
35)-alkyl-amino; Single aryl-amino; Diaryl-amino; Monocycle-(C
3-C
8)-alkyl list arylamino; List-(C
1-C
35)-alkyl list aryl-amino; Amino thio-carbonyl-amino; Amino carbonyl amino; Sulfamyl; N-monocycle-(C
3-C
8)-alkyl-sulfamyl; N-list-(C
1-C
35)-alkyl-sulfamyl; N, N-two ring-(C
3-C
8)-alkyl-sulfamyl; N, N-two-(C
1-C
35)-alkyl-sulfamyl; Single aryl-the sulfamyl of N-; N, N-diaryl-sulfamyl; N-monocycle-(C
3-C
8The single ammonia aryl sulfonyl of)-alkyl-N-; N-list-(C
1-C
35The single ammonia aryl sulfonyl of)-alkyl-N-; Amino-sulfonyl amino; (C
1-C
35)-alkyl sulfenyl; Artyl sulfo; (C
1-C
35)-alkyl sulphonyl or aryl sulfonyl;
G
12Representative (C
2-C
35)-alkyl; (C
2-C
35)-alkoxyl group; (C
2-C
35)-acyl group; (C
2-C
35)-acyloxy; (C
2-C
35)-acyl amino; (C
2-C
35)-alkyl sulfonyl-amino; N-list-(C
2-C
35)-alkyl-formamyl; N, N-two-(C
2-C
35)-alkyl-formamyl; N-list-(C
2-C
35The single aryl-amino-carbonyl of)-alkyl-N-; (C
2-C
35)-alkoxy carbonyl; List-(C
2-C
35)-alkyl-amino; Two-(C
2-C
35)-alkyl-amino; List-(C
2-C
35)-alkyl list aryl-amino; N-list-(C
2-C
35)-alkyl-sulfamyl; N, N-two-(C
2-C
35)-alkyl-sulfamyl; N-list-(C
2-C
35The single ammonia aryl sulfonyl of)-alkyl-N-; (C
2-C
35)-alkyl sulfenyl or (C
2-C
35)-alkyl sulphonyl; Wherein alkyl group is interrupted by one or more heteroatomss;
R
14To R
16Independent separately representative ring-(C
5-C
6)-alkyl; Heterocyclylalkyl; Heteroaryl; Aryl; (C
1-C
35)-alkyl; (the C that is interrupted by one or more heteroatomss
2-C
35)-alkyl; By one or more substituting group G
13(the C that replaces
1-C
35)-alkyl; Perhaps interrupted and by one or more substituting group G by one or more heteroatomss
13(the C that replaces
2-C
35)-alkyl, and R
14And R
15Can also represent hydrogen separately;
G
13Represent trifluoromethyl; Ring-(C
3-C
8)-alkyl; Aryl; Heteroaryl; Heterocyclylalkyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
35)-alkoxyl group; Aryloxy; (C
2-C
35)-acyl group; Aryl carbonyl; (C
2-C
35)-acyloxy; Aryl carbonyl oxygen base; (C
2-C
35)-acyl amino; Amino; Monocycle-(C
3-C
8)-alkyl-amino; List-(C
1-C
35)-alkyl-amino; Two ring-(C
3-C
8)-alkyl-amino; Two-(C
1-C
35)-alkyl-amino; Single arylamino; Ammonia diaryl base; Monocycle-(C
3-C
8)-alkyl list arylamino; List-(C
1-C
35)-alkyl list arylamino; (C
1-C
35)-alkyl sulfenyl; Artyl sulfo; (C
1-C
35)-alkyl sulphonyl or aryl sulfonyl; And
Aryl is represented a group with formula (9) or formula (10):
Wherein
R
17To R
23The independent separately hydrogen of representing; (C
1-C
12)-alkyl; Ring-(C
3-C
8)-alkyl; Trifluoromethyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
6)-alkoxyl group; (C
2-C
6)-acyl group; (C
2-C
6)-acyl amino; (C
1-C
6)-alkyl sulfonyl-amino; Formamyl; N-list-(C
1-C
6)-alkyl-formamyl; N, N-two-(C
1-C
6)-alkyl-formamyl; Amino; N-list-(C
1-C
6)-alkyl-amino; Two-N, N-(C
1-C
6)-alkyl-amino; Amino carbonyl amino; Sulfamyl; N-list-(C
1-C
6)-alkyl-sulfamyl; Two-N, N-(C
1-C
6)-alkyl-sulfamyl; Amino-sulfonyl amino; (C
1-C
6)-alkyl sulfenyl or (C
1-C
6)-alkyl sulphonyl.
2. dyestuff as claimed in claim 1 meets formula (Ia)
Wherein
R
1' and R
2' have identical or different definition separately at a intramolecularly with structural formula (Ia), and independent separately representative: Ar; Ring-(C
5-C
6)-alkyl; Heteroaryl with 5 or 6 ring structures; Heterocyclylalkyl with 5 or 6 ring structures; (C
1-C
18)-alkyl; (the C that is interrupted by one or more heteroatomss
2-C
18)-alkyl; By one or more substituting group G
14(the C that replaces
1-C
18)-alkyl; Interrupted by one or more heteroatomss and by one or more substituting group G
14(the C that replaces
2-C
18)-alkyl; Perhaps group with formula (3a):
And R
1' can also represent hydrogen; Wherein
R
4' represent hydrogen or (C
1-C
35)-alkyl;
W represents 1,2 or 3;
S represents one from 0.1 to 100 rational number, and has identical or different definition at an intramolecularly with structural formula (I);
R
5' and R
6' independent separately hydrogen or the (C of representing
1-C
35)-alkyl;
R wherein
5' and R
6' have identical or different definition separately at a intramolecularly with formula (I); Work as R
5' and R
6' when an intramolecularly with formula (I) had different definition, these different definition were that repeating unit stochastic distribution or that have corresponding identical definition is connected to each other;
U ' represents hydrogen, (C
1-C
35)-alkyl, aryl, aryloxy, (C
1-C
35)-alkoxyl group or (C
1-C
35)-alkyl-aryloxy;
G
14Represent trifluoromethyl; Ring-(C
5-C
6)-alkyl; Aryl; Heteroaryl with 5 or 6 ring structures; Heterocyclylalkyl with 5 or 6 ring structures; Hydroxyl; (C
1-C
18)-alkoxyl group; (C
1-C
18)-alkoxy carbonyl; Aryloxy; (C
2-C
18)-acyl group; (C
2-C
18)-acyloxy or aryl carbonyl;
Ar represent a formula (5a) or (6a) shown in group:
Wherein
R
7' to R
9' the independent separately hydrogen of representing; (C
1-C
18)-alkyl; Trifluoromethyl; Ring-(C
5-C
6)-alkyl; Aryl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
18)-alkoxyl group; Aryloxy; (C
2-C
18)-acyl group; Aryl carbonyl; (C
2-C
18)-acyl amino; (C
1-C
18)-alkyl sulfonyl-amino; Arlysulfonylamino; Aryl-amino-carbonyl; Formamyl; N-list-(C
1-C
18)-alkyl-formamyl; Amino; List-(C
1-C
18)-alkyl-amino; Two-(C
1-C
18)-alkyl-amino; Single aryl-amino; List-(C
1-C
18)-alkyl list aryl-amino; Amino carbonyl amino; Sulfamyl; N-list-(C
1-C
18)-alkyl-sulfamyl; Amino-sulfonyl amino; (C
1-C
18)-alkyl sulfenyl; Artyl sulfo; (C
1-C
18)-alkyl sulphonyl or aryl sulfonyl; And
R
10' to R
13' the independent separately hydrogen, (C represented
1-C
18)-alkyl or a group with formula (7a) or formula (8a):
Wherein, R
14' to R
16' independent separately representative (C
5-C
6)-cycloalkyl; Heterocyclylalkyl with 5 or 6 ring structures; Heteroaryl with 5 or 6 ring structures; Aryl; (C
1-C
18)-alkyl; (the C that is interrupted by one or more heteroatomss
2-C
18)-alkyl; By one or more substituting group G
15(the C that replaces
1-C
18)-alkyl; Perhaps interrupted and by one or more substituting group G by one or more heteroatomss
15(the C that replaces
2-C
18)-alkyl; And R
14' and R
15' can also represent hydrogen separately;
G
15Represent trifluoromethyl; Ring-(C
5-C
6)-alkyl; Aryl; Heteroaryl with 5 or 6 ring structures; Heterocyclylalkyl with 5 or 6 ring structures; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
18)-alkoxyl group; Aryloxy; (C
2-C
18)-acyl group; Aryl carbonyl; Two-(C
1-C
18)-alkyl-amino; Single aryl-amino; Diaryl-amino; List-(C
1-C
18)-alkyl list aryl-amino; (C
1-C
18)-alkyl sulfenyl; Artyl sulfo; (C
1-C
18)-alkyl sulphonyl or aryl sulfonyl; And
Aryl represents one to have formula (9a) or group (10a):
Wherein
R
17' to R
19' the independent separately hydrogen of representing; (C
1-C
12)-alkyl; Trifluoromethyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
6)-alkoxyl group; (C
2-C
6)-acyl group; Amino; (C
2-C
6)-acyl group-amino; List-(C
1-C
6)-alkyl-amino; Sulfamyl; Formamyl or (C
1-C
6)-alkyl sulfenyl; And
R
20' to R
23' independent separately hydrogen or the (C of representing
1-C
6)-alkyl.
3. dyestuff as claimed in claim 1 meets formula (Ib)
Wherein
R
3' have identical or different definition and represent Ar at an intramolecularly with formula (Ib); Ring-(C
5-C
6)-alkyl; Heteroaryl with 5 or 6 ring structures; Heterocyclylalkyl with 5 or 6 ring structures; (C
1-C
18)-alkyl; (the C that is interrupted by one or more heteroatomss
2-C
18)-alkyl; By one or more substituting group G
14(the C that replaces
1-C
18)-alkyl; Perhaps interrupted and by one or more substituting group G by one or more heteroatomss
14(the C that replaces
2-C
18)-alkyl; G wherein
14Definition with claim 2;
Ar represents one to have formula (5a) or group (6a):
Wherein
R
7' to R
9' the independent separately hydrogen of representing; (C
1-C
18)-alkyl; Trifluoromethyl; Ring-(C
5-C
6)-alkyl; Aryl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
18)-alkoxyl group; Aryloxy; (C
2-C
18)-acyl group; Aryl carbonyl; (C
2-C
18)-acyl amino; (C
1-C
18)-alkyl sulfonyl-amino; Arlysulfonylamino; Aryl-amino-carbonyl; Formamyl; N-list-(C
1-C
18)-alkyl-formamyl; Amino; List-(C
1-C
18)-alkyl-amino; Two-(C
1-C
18)-alkyl-amino; Single aryl-amino; List-(C
1-C
18)-alkyl list aryl-amino; Amino carbonyl amino; Sulfamyl; N-list-(C
1-C
18)-alkyl-sulfamyl; Amino-sulfonyl amino; (C
1-C
18)-alkyl sulfenyl; Artyl sulfo; (C
1-C
18)-alkyl sulphonyl or aryl sulfonyl; And
R
10' to R
13' the independent separately hydrogen, (C represented
1-C
18)-alkyl;
Aryl represents one to have formula (9a) or group (10a):
Wherein
R
17' to R
19' the independent separately hydrogen of representing; (C
1-C
12)-alkyl; Trifluoromethyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
6)-alkoxyl group; (C
2-C
6)-acyl group; Amino; (C
2-C
6)-acyl group-amino; List-(C
1-C
6)-alkyl-amino; Sulfamyl; Formamyl or (C
1-C
6)-alkyl sulfenyl; And
R
20' to R
23' independent separately hydrogen or the (C of representing
1-C
6)-alkyl.
4. dyestuff as claimed in claim 1 meets formula (Ic)
Wherein
R
1", R
2" and R
3" have identical or different implication separately at a intramolecularly with formula (Ic), and the independent separately Ar that represents; Ring-(C
5-C
6)-alkyl; Heteroaryl with 5 or 6 ring structures; Heterocyclylalkyl with 5 or 6 ring structures; (C
1-C
18)-alkyl; (the C that is interrupted by one or more heteroatomss
2-C
18)-alkyl; By one or more substituting group G
14(the C that replaces
1-C
18)-alkyl; Interrupted by one or more heteroatomss and by one or more substituting group G
14(the C that replaces
2-C
18)-alkyl; And R
1" can also represent hydrogen; G wherein
14Definition with claim 2;
Ar represents a group with formula (5a) or formula (6a):
Wherein
R
7' to R
9' the independent separately hydrogen of representing; (C
1-C
18)-alkyl; Trifluoromethyl; Ring-(C
5-C
6)-alkyl; Aryl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
18)-alkoxyl group; Aryloxy; (C
2-C
18)-acyl group; Aryl carbonyl; (C
2-C
18)-acyl amino; (C
1-C
18)-alkyl sulfonyl-amino; Arlysulfonylamino; Aryl-amino-carbonyl; Formamyl; N-list-(C
1-C
18)-alkyl-formamyl; Amino; List-(C
1-C
18)-alkyl-amino; Two-(C
1-C
18)-alkyl-amino; Single aryl-amino; List-(C
1-C
18)-alkyl list aryl-amino; Amino carbonyl amino; Sulfamyl; N-list-(C
1-C
18)-alkyl-sulfamyl; Amino-sulfonyl amino; (C
1-C
18)-alkyl sulfenyl; Artyl sulfo; (C
1-C
18)-alkyl sulphonyl or aryl sulfonyl; And
R
10' to R
13' the independent separately hydrogen, (C represented
1-C
18)-alkyl;
Aryl represents one to have formula (9a) or group (10a):
Wherein
R
17' to R
19' the independent separately hydrogen of representing; (C
1-C
12)-alkyl; Trifluoromethyl; Halogen; Cyano group; Nitro; Hydroxyl; (C
1-C
6)-alkoxyl group; (C
2-C
6)-acyl group; Amino; (C
2-C
6)-acyl group-amino; List-(C
1-C
6)-alkyl-amino; Sulfamyl; Formamyl or (C
1-C
6)-alkyl sulfenyl; And
R
20' to R
23' independent separately hydrogen or the (C of representing
1-C
6)-alkyl.
5. one kind prepares the described method with dyestuff of formula (I) of claim 1, comprises making the have formula compound of (II) and one have the compound of formula (III) or having the compound of formula (IV) or have the compound of formula (III) and have the mixture condensation of the compound of formula (IV);
R wherein
1To R
3Definition separately is with claim 1.
6. be used for the painted purposes of polymkeric substance as one among the claim 1-4 or multinomial described dyestuff with formula (I).
7. a masterbatch comprises as one among the claim 1-4 or multinomial described a kind of compound and a kind of solid support material with formula (I).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200810059110 DE102008059110A1 (en) | 2008-11-26 | 2008-11-26 | Dyes for polymer dyeing, process for their preparation and their use |
| DE102008059110.6 | 2008-11-26 | ||
| PCT/EP2009/065430 WO2010060849A2 (en) | 2008-11-26 | 2009-11-19 | Dyes for polymer coloration, their preparation and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102224203A true CN102224203A (en) | 2011-10-19 |
Family
ID=42114676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009801466171A Pending CN102224203A (en) | 2008-11-26 | 2009-11-19 | Dyes for polymer coloration, their preparation and their use |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP2370522A2 (en) |
| JP (1) | JP2012509950A (en) |
| CN (1) | CN102224203A (en) |
| BR (1) | BRPI0921179A2 (en) |
| DE (1) | DE102008059110A1 (en) |
| WO (1) | WO2010060849A2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5952228B2 (en) * | 2013-07-01 | 2016-07-13 | 大日精化工業株式会社 | Pigment colorant |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6088185A (en) * | 1983-10-18 | 1985-05-17 | 東洋インキ製造株式会社 | Pigment dispersant |
| DE59007845D1 (en) | 1989-10-10 | 1995-01-12 | Ciba Geigy Ag | New dianthraquinonyl compounds. |
| EP0648817B1 (en) | 1993-10-13 | 1999-11-10 | Ciba SC Holding AG | Novel fluorescent dyes |
| JP3149707B2 (en) | 1994-10-28 | 2001-03-26 | 東洋インキ製造株式会社 | Pigment dispersion method and aqueous pigment dispersion |
| JPH09137075A (en) * | 1995-11-14 | 1997-05-27 | Nippon Kayaku Co Ltd | Pigment dispersant and pigment composition using the same |
| JP3837772B2 (en) * | 1996-04-08 | 2006-10-25 | 東洋インキ製造株式会社 | Method for producing pigment composition, pigment composition and colorant composition |
| US6605126B1 (en) | 2000-06-02 | 2003-08-12 | Milliken & Co. | Low-viscosity polymeric colorants exhibiting high color strength characteristics |
| JP4089180B2 (en) | 2001-07-30 | 2008-05-28 | 東洋インキ製造株式会社 | Coloring composition for color filter and color filter |
| JP4576890B2 (en) * | 2004-06-04 | 2010-11-10 | 東洋インキ製造株式会社 | Red coloring composition for color filter and color filter |
| TWI341853B (en) * | 2005-07-01 | 2011-05-11 | Toyo Ink Mfg Co | Red colored film, red colored composition, color filter and liquid crystal display device |
| JP5315608B2 (en) * | 2005-12-21 | 2013-10-16 | 東洋インキＳｃホールディングス株式会社 | Pigment dispersion and colored resin composition |
| JP4802746B2 (en) * | 2006-02-08 | 2011-10-26 | 凸版印刷株式会社 | Photosensitive coloring composition and color filter |
-
2008
- 2008-11-26 DE DE200810059110 patent/DE102008059110A1/en not_active Withdrawn
-
2009
- 2009-11-19 WO PCT/EP2009/065430 patent/WO2010060849A2/en active Application Filing
- 2009-11-19 EP EP09759930A patent/EP2370522A2/en not_active Withdrawn
- 2009-11-19 CN CN2009801466171A patent/CN102224203A/en active Pending
- 2009-11-19 BR BRPI0921179A patent/BRPI0921179A2/en not_active Application Discontinuation
- 2009-11-19 JP JP2011536859A patent/JP2012509950A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010060849A3 (en) | 2010-07-29 |
| DE102008059110A1 (en) | 2010-05-27 |
| BRPI0921179A2 (en) | 2018-10-16 |
| EP2370522A2 (en) | 2011-10-05 |
| WO2010060849A2 (en) | 2010-06-03 |
| JP2012509950A (en) | 2012-04-26 |
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