CN1288211C - 吡啶酮染料及其制备方法、在有色塑料或聚合物有色颗粒的制备中的用途 - Google Patents
吡啶酮染料及其制备方法、在有色塑料或聚合物有色颗粒的制备中的用途 Download PDFInfo
- Publication number
- CN1288211C CN1288211C CNB028061977A CN02806197A CN1288211C CN 1288211 C CN1288211 C CN 1288211C CN B028061977 A CNB028061977 A CN B028061977A CN 02806197 A CN02806197 A CN 02806197A CN 1288211 C CN1288211 C CN 1288211C
- Authority
- CN
- China
- Prior art keywords
- formula
- pyridone
- alkyl
- azoic dyestuff
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000004033 plastic Substances 0.000 title claims abstract description 14
- 229920003023 plastic Polymers 0.000 title claims abstract description 14
- 239000002245 particle Substances 0.000 title claims abstract description 11
- 239000000975 dye Substances 0.000 title claims description 41
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 title claims description 35
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 239000006096 absorbing agent Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 238000006193 diazotization reaction Methods 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 20
- 239000012964 benzotriazole Substances 0.000 abstract description 9
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 abstract description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 6
- 125000003118 aryl group Chemical group 0.000 abstract description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 4
- 239000004305 biphenyl Substances 0.000 abstract description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 3
- 229930192474 thiophene Natural products 0.000 abstract description 3
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 abstract description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 abstract description 2
- 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 abstract description 2
- 150000004056 anthraquinones Chemical class 0.000 abstract description 2
- 235000010290 biphenyl Nutrition 0.000 abstract description 2
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 abstract description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical class C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 2
- 150000003949 imides Chemical class 0.000 abstract description 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical class 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 abstract 1
- -1 isobutyl- Chemical group 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 239000000376 reactant Substances 0.000 description 7
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000000176 photostabilization Effects 0.000 description 5
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 3
- 239000004902 Softening Agent Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001565 benzotriazoles Chemical class 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 238000012545 processing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
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- 239000011324 bead Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
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- 238000001035 drying Methods 0.000 description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- HQEPZWYPQQKFLU-UHFFFAOYSA-N (2,6-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(O)=C1C(=O)C1=CC=CC=C1 HQEPZWYPQQKFLU-UHFFFAOYSA-N 0.000 description 1
- GOZHNJTXLALKRL-UHFFFAOYSA-N (5-benzoyl-2,4-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(O)=C(C(=O)C=2C=CC=CC=2)C=C1C(=O)C1=CC=CC=C1 GOZHNJTXLALKRL-UHFFFAOYSA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- WXHVQMGINBSVAY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 WXHVQMGINBSVAY-UHFFFAOYSA-N 0.000 description 1
- ITLDHFORLZTRJI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1N1N=C2C=CC=CC2=N1 ITLDHFORLZTRJI-UHFFFAOYSA-N 0.000 description 1
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- LHHLLQVLJAUUDT-UHFFFAOYSA-N 2-ethylhexyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCC(CC)CCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O LHHLLQVLJAUUDT-UHFFFAOYSA-N 0.000 description 1
- RYAIMSPHUVXLQI-UHFFFAOYSA-N 4-(aminomethyl)-2-(benzotriazol-2-yl)phenol Chemical compound NCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 RYAIMSPHUVXLQI-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- NKBHDHWFTJYJSK-UHFFFAOYSA-N butyl 2-cyano-3-(4-methoxyphenyl)but-2-enoate Chemical compound CCCCOC(=O)C(C#N)=C(C)C1=CC=C(OC)C=C1 NKBHDHWFTJYJSK-UHFFFAOYSA-N 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
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- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 1
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- JMFYZMAVUHNCPW-UHFFFAOYSA-N dimethyl 2-[(4-methoxyphenyl)methylidene]propanedioate Chemical class COC(=O)C(C(=O)OC)=CC1=CC=C(OC)C=C1 JMFYZMAVUHNCPW-UHFFFAOYSA-N 0.000 description 1
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- 150000002240 furans Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 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
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- WGGBUPQMVJZVIO-UHFFFAOYSA-N methyl 2-cyano-3-(4-methoxyphenyl)but-2-enoate Chemical class COC(=O)C(C#N)=C(C)C1=CC=C(OC)C=C1 WGGBUPQMVJZVIO-UHFFFAOYSA-N 0.000 description 1
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
- YVYHWOZEQUFKOB-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]oxamide Chemical compound CN(C)CCCNC(=O)C(N)=O YVYHWOZEQUFKOB-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N ortho-hydroxybenzophenone Natural products OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- GDESWOTWNNGOMW-UHFFFAOYSA-N resorcinol monobenzoate Chemical compound OC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 GDESWOTWNNGOMW-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
- C09B62/24—Azo dyes
- C09B62/245—Monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
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- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
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- 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
本发明涉及式(1)吡啶酮偶氮染料,其中A为重氮组分的苯、萘、联苯、偶氮苯、噻吩、苯并噻唑、苯并异噻唑、噻二唑、吲唑、苯并三唑、吡唑、蒽醌、萘二甲酰亚胺、色酮、邻苯二甲酰亚胺或二苯并呋喃系列基团;R1为氢、未取代的或羟基或苯基取代的C1-C6烷基,C3以上的烷基链可被一或多个氧原子间隔,或R1与R2的意义相同;R2为式(2)、(3)、(4)、(5)、(6)或(7)的基团,其中B为桥连基,R4为烷基或芳基,R5和R6各自独立为烷基、芳基或杂芳基,A如式(1)所定义,或R1和R2与-NR1R2中的氮原子一起形成杂环,Y为氰基、-CONH2或-CH2SO3H,n为2-6的整数。本发明还涉及所述染料的制备及其在有色塑料或聚合物有色颗粒制备中的用途。
Description
本发明涉及吡啶酮偶氮染料及其制备方法、在有色塑料或聚合物有色颗粒的制备中的用途。
已知吡啶酮偶氮染料及其在半合成或合成疏水性纤维材料染色中的用途。然而,已经表明当将已知的吡啶酮偶氮染料用于合成原料(塑料)的整体染色时,这些染料往往不能完全满足最高要求,尤其在耐热性、色移性和/或着色力方面的要求。因此,需要可产生热稳定着色的强力整体染色并具有良好全面稳定性质的新的吡啶酮染料。
现已意外地发现本发明的吡啶酮偶氮染料在很大程度上满足上述要求。
因此,本发明涉及下式的吡啶酮偶氮染料
其中
A为重氮组分的苯、萘、联苯、偶氮苯、噻吩、苯并噻唑、苯并异噻唑、噻二唑、吲唑、苯并三唑、吡唑、蒽醌、萘二甲酰亚胺(naphtholicacid imide)、色酮、邻苯二甲酰亚胺或二苯并呋喃系列基团,
R1为氢、未取代的或羟基或苯基取代的C1-C6烷基,C3以上的烷基链可被一或多个氧原子间隔,或R1与R2的意义相同,
R2为下式的基团
其中B为桥连基,R4为烷基或芳基,R5和R6各自独立为烷基、芳基或杂芳基,A如式(1)所定义,或
R1和R2与-NR1R2中的氮原子一起形成杂环,
Y为氰基、-CONH2或-CH2SO3H,和
n为2-6的整数。
A优选为重氮基组分的苯系列基团。
特别优选A为下式的基团
其中
R7为氢或卤素,
R8为氢、卤素、氰基、-CF3、-COOR11,其中R11为C1-C4烷基,且所述烷基链可被氧间隔,或R8为苄基或-SO2R12,其中R12为-NR13R14或苯基,且R13为氢或C1-C4烷基和R14为C1-C4烷基或苄基,
R9为氢或卤素,和
R10为氢或-SO2-O-C6H5基团。
作为R1的C1-C6烷基为例如甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、叔戊基(1,1-二甲基丙基)、1,1,3,3-四甲基丁基、己基、1-甲基戊基、新戊基、环戊基、环己基及其相关异构体,尤其是甲基。R1优选为甲基、乙基或-CO-R6(7)基团,特别是氢。
R4、R5和R6定义中的烷基为例如C1-C4烷基,例如甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基和叔丁基,和被C1-C2烷氧基或被苄氧基取代的C1-C4烷基,或C5-C6环烷基如环戊基和环己基。
R4、R5和R6定义中的芳基为例如苯基或萘基。
由-NR1R2中的R1、R2及氮原子形成的杂环为例如邻苯二甲酰亚胺基、内酰胺或糖精系列的杂环。
R5定义中的杂芳基为例如噻唑基、三唑基或噻二唑基。
R6定义中的杂芳基为例如噻吩或呋喃。
作为R11、R13和R14的C1-C4烷基为甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基或叔丁基。
Y优选为氰基。
作为R7、R8和R9的卤素为溴、碘,尤其为氯。
桥连基B为例如亚苯基、亚萘基、噻吩基或呋喃基。
n优选为2-4的数,尤其是2或3。
特别优选具有下式的吡啶酮偶氮染料
本发明还涉及制备本发明的式(1)吡啶酮偶氮染料的方法。
例如,如下制备所述染料:根据常规方法,使式
A-NH2 (50)的化合物重氮化,随后与下式的偶合组分偶合
A、R1、R2、Y和n如上述对式(1)的定义。
用本领域已知的方法,例如在酸性含水介质,如含盐酸或含硫酸的含水介质中用亚硝酸钠进行式(50)化合物的重氮化作用。但也可用其它重氮化试剂,例如用亚硝基硫酸进行所述重氮化作用。在所述重氮化作用中,在所述反应介质中还可存在其它酸如磷酸、硫酸、乙酸、丙酸、盐酸,或这些酸的混合物,如丙酸和乙酸的混合物。所述重氮化作用最好在-10-30℃的温度下进行,例如在-10℃-室温下进行。
经重氮化的式(50)化合物与式(51)偶合组分的偶合作用同样按已知的方法进行,例如在酸性含水介质或酸性含水有机介质,最好在-10-30℃,特别是低于10℃的温度下进行。所用酸的实例有盐酸、乙酸、丙酸、硫酸或磷酸。
式(50)化合物是已知的或可用本领域已知的方法制备。
式(51)的偶合组分是已知的或可用本领域已知的方法制备,例如首先使下式化合物
NC-CH2-CO-O-CH2CH3 (52)
与下式化合物反应
H2N-(CH2)2-NH2 (53),
接着与下式化合物反应
H3C-CO-CH2-COO-CH2CH3 (54)
生成下式化合物
或,例如,通过首先使2mol下式化合物
NC-CH2-CO-O-CH2CH3 (52)
与下式化合物反应
H2N-(CH2)2-NH-(CH2)2NH2 (56),
接着与2mol下式化合物反应
H3C-CO-CH2-COO-CH2CH3 (54)
生成下式化合物
按照本领域已知的方法,以式(55)和(57)化合物为原料,通过使其中的氨基与如苯甲酰氯或乙酰氯进一步反应可制备相应的式(51)的化合物。
式(52)-(54)和(56)是已知的且可用本领域已知的方法制备。
本发明还涉及有色塑料或聚合物有色颗粒的制备方法,所述方法包括使高分子量的有机原料和着色有效量的至少一种式(1)的吡啶酮偶氮染料混合。
通过用如辊式轧墨机、混合装置或造粒装置将所述吡啶酮偶氮染料混入高分子量有机物质中,使所述吡啶酮偶氮染料溶解或细碎分散在这些基质中来进行所述高分子量原料与式(1)的吡啶酮偶氮染料的着色。随后用本领域已知的方法,如压延、压塑、挤塑、涂布、抽丝、浇铸或注塑加工处理所述高分子量有机原料与混合在一起的吡啶酮偶氮染料,从而使着色的原料成其最终形状。也可在所述实际加工处理步骤之前,立即进行所述吡啶酮偶氮染料的混合,例如,在连续喂入粉状吡啶酮偶氮染料的同时,将粒状或粉状的高分子量有机原料和任选的其它辅助成分如添加剂直接进料至挤出机的进料区,在该区中正好在加工处理前进行混合。但一般说来,优选将吡啶酮偶氮染料预先与高分子量有机原料混合,因为可使所述基质更均匀地着色。
为了制备非刚性的模塑物或降低其脆性,通常最好在成型前往所述高分子量化合物中掺入所谓的增塑剂。可用作增塑剂的有例如磷酸酯、苯二甲酸酯或癸二酸酯。在本发明方法中,增塑剂可在掺入色料之前或之后掺入聚合物中。为达到不同的色调,除式(1)的吡啶酮偶氮染料外,还可往所述高分子量的有机原料中加入任何需要量的其它吡啶酮偶氮染料或其它色料,任选同时加入其它添加剂例如填料或催干剂。
为增强耐光性,最好向用本发明的式(1)吡啶酮偶氮染料着色的塑料或聚合物颗粒中混入紫外线吸收剂。紫外线吸收剂的用量可在较大的范围内变化:紫外线吸收剂的用量最好为0.01-1.0%重量,尤其是0.05-0.6%重量,更特别为0.1-0.4%重量,基于塑料或聚合物颗粒的重量计算。
适用的紫外线吸收剂具体有2-(2’-羟基苯基)苯并三唑、2-羟基二苯甲酮、取代或未取代的苯甲酸酯、丙烯酸酯、草酰胺、2-(2-羟基苯基)-1,3,5-三嗪、间苯二酚或甲脒的单苯甲酸酯和在25℃下,比重为1200-1400,优选1300-1350的下式的聚酯紫外线吸收剂:
可提及的2-(2’-羟基苯基)苯并三唑类化合物有如2-(2’-羟基-5’-甲基苯基)苯并三唑、2-(3’,5’-二叔丁基-2’-羟基苯基)苯并三唑、2-(5’-叔丁基-2’-羟基苯基)苯并三唑、2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)苯基)苯并三唑、2-(3’,5’-二叔丁基-2’-羟基苯基)-5-氯代苯并三唑、2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯代苯并三唑、2-(3’-仲丁基-5’-叔丁基-2’-羟基苯基)苯并三唑、2-(2’-羟基-4’-辛氧基苯基)苯并三唑、2-(3’,5’-二叔戊基-2’-羟基苯基)苯并三唑、2-(3’,5’-双(α,α-二甲基苄基)-2’-羟基苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)-5-氯代苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)-5-氯代苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-5-氯代苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)苯并三唑、2-(3’-十二烷基-2’-羟基-5’-甲基苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-异辛氧基羰基乙基)苯基苯并三唑、2,2’-亚甲基-双[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3’-叔丁基-5’-(2-甲氧基羰基乙基)-2’-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯交换产物;[R-CH2CH2-COO-CH2CH2-]2-,其中R=3’-叔丁基-4’-羟基-5’-2H-苯并三唑-2-基苯基;2-[2’-羟基-3’-(α,α-二甲基苄基)-5’-(1,1,3,3-四甲基丁基)苯基]苯并三唑;和2-[2’-羟基-3’-(1,1,3,3-四甲基丁基)-5’-(α,α-二甲基苄基)苯基]苯并三唑。
可提及的2-羟基二苯甲酮类化合物有例如4-羟基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2’,4’-三羟基和2’-羟基-4,4’-二甲氧基衍生物。
可提及的2-(2-羟基苯基)-1,3,5-三嗪类化合物有例如2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2,4-双(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-双(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十三烷氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-己氧基)苯基-4,6-二苯基-1,3,5-三嗪、2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪、2,4,6-三[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪和2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪。
可提及的草酰胺类化合物有如4,4’-二辛氧基-N,N’-草酰二苯胺、2,2’-二乙氧基-N,N’-草酰二苯胺、2,2’-二辛氧基-5,5’-二叔丁氧基-N,N’-草酰二苯胺、2,2’-二(十二烷氧基)-5,5’-二叔丁氧基-N,N’-草酰二苯胺、2-乙氧基-2’-乙氧基-N,N’-草酰二苯胺、N,N’-双(3-二甲基氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2’-乙氧基-N,N’-草酰二苯胺及其与2-乙氧基-2’-乙基-5,4’-二叔丁氧基-N,N’-草酰二苯胺的混合物、邻-和对-甲氧基-二取代的N,N’-草酰二苯胺混合物和邻-和对-乙氧基-二取代的N,N’-草酰二苯胺混合物。
可提及的取代或未取代的苯甲酸酯有如水杨酸4-叔丁基苯酯、水杨酸苯酯、水杨酸辛基苯酯、二苯甲酰间苯二酚、双(4-叔丁基苯甲酰基)间苯二酚、苯甲酰间苯二酚、3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯酯、3,5-二叔丁基-4-羟基苯甲酸十六烷酯、3,5-二叔丁基-4-羟基苯甲酸十八烷酯或3,5-二叔丁基-4-羟基苯甲酸2-甲基-4,6-二叔丁基苯酯。
可提及的丙烯酸酯类化合物有如α-氰基-β,β-二苯基丙烯酸乙酯、α-氰基-β,β-二苯基丙烯酸异辛酯、α-甲酯基肉桂酸甲酯、α-氰基-β-甲基-对甲氧基肉桂酸甲酯、α-氰基-β-甲基-对甲氧基肉桂酸丁酯、α-甲酯基-对甲氧基肉桂酸甲酯或N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚。
间苯二酚单苯甲酸酯为例如下式的化合物:
甲脒为如下式的化合物:
优选对特别呈纤维、颗粒或模塑形状(例如固体或液体物质的容器例如瓶子)的热塑性塑料着色。待根据本发明进行着色的优选的高分子量有机原料是非常普通的、介电常数≥2.5的聚合物,具体有聚酯、聚碳酸酯(PC)、聚苯乙烯(PS)、聚甲基丙烯酸甲酯(PMMA)、聚酰胺、聚乙烯、聚丙烯、苯乙烯/丙烯腈(SAN)或丙烯腈/丁二烯/苯乙烯共聚物(ABS)。特别优选聚酯和聚酰胺。极优选的有:可通过对苯二甲酸或萘-2,6-二甲酸和二元醇,尤其是乙二醇的缩聚得到的线性芳族聚酯,或对苯二甲酸和1,4-双(羟甲基)环己烷的缩合产物,例如聚对苯二甲酸乙二醇酯(PET)、聚萘-2,6-二甲酸乙二醇酯(PEN)或聚对苯二甲酸丁二醇酯(PBTP);和聚碳酸酯,例如由α,α-二甲基-4,4-二羟基-二苯基甲烷和光气得到的那些聚碳酸酯,或基于聚氯乙烯的聚合物和基于聚酰胺的聚合物,例如聚酰胺-6或聚酰胺-6,6。
本发明的吡啶酮偶氮染料赋予所提及的原料,尤其是聚酯原料具有优异的耐用性、特别是良好耐光性和高温耐光性的强着色力及均匀色调。特别值得一提的是所获得的染色具有良好色移稳定性和热色移稳定性。
本发明还涉及有色塑料或聚合物有色颗粒的制备方法,所述方法包括使用式(1)吡啶酮偶氮染料和紫外线吸收剂的组合,其中使用对上述吡啶酮偶氮染料和紫外线吸收剂的含义和优选含义。
本发明还涉及用上述方法整体染色的塑料。
下列实施例用于说明本发明。除非另有说明,否则份数为重量份,百分比为重量百分比。温度为摄氏度。重量比和体积比之间的关系为克和立方厘米之间的关系。
实施例1
(A)将140.0ml水置于反应容器内并冷却到0-5℃。在30分钟内加入405.2ml 1,2-乙二胺,再逐滴加入215.4ml氰基乙酸乙酯,冷却使其温度保持低于20℃。接着在20℃下搅拌所述反应混合物16小时,60℃下真空蒸馏出过量的1,2-乙二胺,并在40℃下搅拌所述混合物1小时。
随后逐滴加入253.0ml乙酰乙酸乙酯,滴加的最后使温度升高到70℃。一旦乙酰乙酸乙酯的加入完成,则依次加入168.0ml 30%氨水溶液和1400.0ml丙醇,在70-75℃下搅拌所述反应混合物16小时。过滤所生成的悬浮液,加入1500.0ml乙醇,于20℃下搅拌14小时并再次过滤。用总量1000.0ml的乙醇分批洗涤所述滤饼并干燥。
得到263.6g下式化合物
(B)将式50.0g式(55)的化合物悬浮于500.0ml的水中,加热至60℃,用32%HCl将pH值调至1.0,并于60℃下搅拌3小时。再从反应物质中过滤出晶状沉淀,用30%的NaOH水溶液将母液的pH值调至9.0,再加入40.0ml的苯甲酰氯。随后将所述反应混合物搅拌18小时,如必要加入HCl使其pH值保持在9.0。接着加入100.0g NaCl,用32%HCl将所述完全反应的反应物的pH值调节至0.5,并于0℃下搅拌直到沉淀出产物。经吸滤过滤出所沉淀出的反应产物并干燥。
得到含62.3g下式化合物的93.5g产物。
(C)于15-20℃下将10.6ml邻氨基苯甲酸乙酯置于110.0ml 98%乙酸中,再加入22.0g 32%HCl。随后往所述反应物中逐滴加入17.8ml4N NaNO2,并于10-15℃下搅拌1小时。接着用氨基磺酸破坏过量的硝酸盐。
(D)将根据(B)制备的14.9g式(58)的化合物置于150.0ml水中;加入22.0g 30%NaOH溶液,加热该混合物至50℃。随后向所生成的悬浮液中逐滴加入120g根据(B)制备的重氮溶液,加入约200.0g冰使其温度保持在15℃。一旦加入完成,将其pH值调至5.0,搅拌该反应物16小时。
再加入300.0ml水,将该完全反应的反应物加热至70℃,吸滤,用水洗涤并干燥。
得到20.0g下式的吡啶酮偶氮染料,该染料可将聚酯染成黄色。
实施例2
(A)将111.95ml二亚乙基三胺置于反应烧瓶中,于20℃下加入氰基乙酸乙酯,将温度升至约75℃。搅拌该反应混合物30分钟,随后加入1000.0ml 94%乙醇,于72℃下搅拌该混合物2小时(回流)。接着依次加入278.3ml乙酰乙酸乙酯、168.0ml 30%氨水和3000.0ml94%乙醇,回流下再搅拌该混合物41小时。
于75℃下吸滤所生成的悬浮液,随后用总量为500.0ml的94%乙醇分批洗涤,接着加入2000.0ml 94%乙醇,在20℃下搅拌该混合物14小时。随后吸滤该悬液,用总量为1000.0ml的94%乙醇分批洗涤该滤饼,并真空干燥。
得到235.6g下式化合物
(B)将92.35g式(57)的化合物悬浮于1000.0ml水中,加热该悬浮液至60℃,用32%HCl将pH值调节至1.0,并于60℃下搅拌3小时。随后从该反应物中过滤出晶状沉淀,用30%NaOH溶液调节该母液的pH值至9.0,加入40.0ml苯甲酰氯。接着搅拌该反应混合物18小时,如必要加入HCl使其pH值保持在9.0。
随后加入200.0g NaCl,并用32%HCl将完全反应的反应物的pH值调节至0.5,并于0℃下搅拌直到沉淀出产物。吸滤出所沉淀出的反应产物并干燥。
得到90.0g下式化合物
(C)在15-30℃下将1.65g邻氨基苯甲酸乙酯置于10.0ml冰醋酸中,加入0.6ml 96%硫酸,搅拌该混合物30分钟。用10分钟向该反应物中逐滴加入1.85ml 40%亚硝基硫酸,于17-20℃下搅拌该混合物1小时。
(D)以100.0ml二甲基甲酰胺(DMF)作为原料,在搅拌下加入2.4g式(59)的化合物和10.0ml冰水。然后,于5-10℃下用30分钟逐滴加入(C)中制备的重氮溶液,同时,为保持其pH值在3-4,加入22.0ml10%NaOH水溶液。
于0-5℃下搅拌该反应混合物4小时,随后调节pH值到4.6,并于20℃下再搅拌17小时。吸滤所生成的悬浮液,依次用25.0ml 80%DMF、乙醇和水洗涤直到pH>6,并干燥。
得到3.3g下式的吡啶酮偶氮染料,该染料可将聚酯染成黄色。
实施例3-185:
按照实施例1和2的类似方法,可制备列于表1-16的下列染料,它们同样将聚酯染成黄色:
表1
表2
表3
表4
表5
表6
表7
表8
表9
表10
表11
表12
表13
表14
表15
表16
染色实施例1:
130℃下预干燥1200.00g聚酯颗粒(PET Arnite D04-300,DSM)4小时,随后与0.24g式(14)的吡啶酮偶氮染料在“辊架(roller rack)”混合装置中以每分钟60转的转速均匀混合15分钟。
在配备有6个加热区(最高温度275℃)的挤出机(双螺杆25mm,购自Collin,D-85560 Ebersberg)中挤出所述均匀混合物,用水冷却,用造粒机(Turb Etuve TE 25,购自MAPAG AG,CH-3001 Bern)中造粒,再于130℃下干燥4小时。
所生成的黄色聚酯颗粒具有良好的全面的稳定性,尤其是非常好的耐光性和高温耐光性。
染色实施例2:
130℃下预干燥1200.00g聚酯颗粒(PET Arnite D04-300,DSM)4小时,再与0.60g式(14)的吡啶酮偶氮染料和3.60g下式的紫外线吸收剂在“辊架”混合装置中以每分钟60转的转速均匀混合15分钟。
在配备有6个加热区(最高温度275℃)的挤出机(双螺杆25mm,购自Collin,D-85560 Ebersberg)中挤出所述均匀混合物,用水冷却,用造粒机(Turb Etuve TE 25,购自MAPAG AG,CH-3001 Bern)中造粒,再于130℃下干燥4小时。
所生成的黄色聚酯颗粒具有良好的全面的稳定性,尤其是非常好的耐光性和高温耐光性。
Claims (8)
1.一种下式的吡啶酮偶氮染料
其中
A为下式的基团
其中R7为氢或卤素,R8为卤素、氰基、-CF3、-COOR11,其中R11为C1-C4烷基,且所述烷基链可被氧间隔,或为-SO2R12,其中R12为-NR13R14或苯基,且R13为C1-C4烷基和R14为C1-C4烷基,R9为氢或卤素,和R10为氢或-SO2-O-C6H5基团,
R1为氢,或式(3)或(7)的基团
R2为下式的基团
其中
B为亚苯基桥连基,
R6为未取代的C1-C4烷基或被C1-C2烷氧基取代的C1-C4烷基或苯基,以及
A如式(1)所定义,或
R1和R2与-NR1R2中的氮原子一起形成邻苯二甲酰亚胺基、内酰胺或糖精系列的杂环,
Y为氰基,和
n为2-6的整数。
2.权利要求1的吡啶酮偶氮染料,所述染料具有下式的结构:
3.根据权利要求2的吡啶酮偶氮染料,其具有以下结构式:
4.一种制备权利要求1的式(1)吡啶酮偶氮染料的方法,所述方法包括使式
A-NH2 (50)的化合物重氮化,随后与下式的偶合组分偶合
A、R1、R2、Y和n如权利要求1中所定义。
5.一种制备有色塑料或聚合物有色颗粒的方法,所述方法包括往这些材料中掺入一种或多种权利要求1所述的式(1)的吡啶酮偶氮染料。
6.一种制备有色塑料或聚合物有色颗粒的方法,所述方法包括使用权利要求1的式(1)的吡啶酮偶氮染料和紫外线吸收剂的组合。
7.权利要求1的式(1)吡啶酮偶氮染料在有色塑料或聚合物有色颗粒的制备中的用途。
8.按照权利要求5或6的方法着色的塑料或聚合物有色颗粒。
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CNB028061977A Expired - Lifetime CN1288211C (zh) | 2001-03-09 | 2002-02-28 | 吡啶酮染料及其制备方法、在有色塑料或聚合物有色颗粒的制备中的用途 |
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US (1) | US6953846B2 (zh) |
EP (1) | EP1368431B1 (zh) |
JP (1) | JP4380990B2 (zh) |
KR (1) | KR20030090664A (zh) |
CN (1) | CN1288211C (zh) |
AT (1) | ATE380221T1 (zh) |
BR (1) | BR0207944A (zh) |
CA (1) | CA2434837A1 (zh) |
DE (1) | DE60223907T2 (zh) |
MX (1) | MXPA03006339A (zh) |
WO (1) | WO2002072707A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102127012A (zh) * | 2009-12-25 | 2011-07-20 | 住友化学株式会社 | 吡啶酮化合物 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060160933A1 (en) * | 2002-08-30 | 2006-07-20 | Ian Christensen | Method of producing coloured plastics or polymeric color particles |
DE60306671T2 (de) * | 2002-10-18 | 2007-07-12 | Clariant Finance (Bvi) Ltd., Road Town | Azoverbindungen |
JP4879752B2 (ja) * | 2003-12-23 | 2012-02-22 | チバ ホールディング インコーポレーテッド | 有機素材を光から保護する方法 |
JP4512507B2 (ja) * | 2004-07-09 | 2010-07-28 | 富士フイルム株式会社 | ピリドンアゾ化合物およびこの互変異性体を含み着色剤含有硬化性組成物、カラーフィルタおよびその製造方法 |
US20070207331A1 (en) * | 2006-03-06 | 2007-09-06 | Pearson Jason C | Azo compounds and coating compositions containing the azo compounds |
TWI470031B (zh) * | 2008-05-14 | 2015-01-21 | Sumitomo Chemical Co | 偶氮化合物或其鹽類 |
TWI461408B (zh) * | 2008-07-02 | 2014-11-21 | Clariant Finance Bvi Ltd | 酸染料 |
TW201134886A (en) * | 2009-12-25 | 2011-10-16 | Sumitomo Chemical Co | Pyridone compound |
US9910196B2 (en) | 2013-09-27 | 2018-03-06 | Canon Kabushiki Kaisha | Dye compound, ink, and resist composition for color filter |
US9658553B2 (en) | 2013-09-27 | 2017-05-23 | Canon Kabushiki Kaisha | Toner |
EP2868705A1 (en) * | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Metal free acid dyes, process for their production and their use |
CN104231660A (zh) * | 2014-08-01 | 2014-12-24 | 浙江昱泰染化科技有限公司 | 一种单偶氮化合物、制品与应用 |
CN112679979B (zh) * | 2020-12-29 | 2023-09-01 | 浙江永合新材料科技有限公司 | 一种苯并三唑类紫外线吸收剂中间体偶氮染料的制备方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH552661A (de) | 1968-11-12 | 1974-08-15 | Ciba Geigy Ag | Verfahren zur herstellung neuer azofarbstoffe. |
CA972353A (en) * | 1970-12-22 | 1975-08-05 | Ciba-Geigy Ag | Azo compounds, their manufacture and use |
ES2066015T3 (es) * | 1989-01-10 | 1995-03-01 | Sumitomo Chemical Co | Composicion de colorantes de dispersion, util para teñir o estampar materiales de fibra hidrofoba. |
DE3927069A1 (de) * | 1989-08-16 | 1991-02-21 | Basf Ag | Phenonazofarbstoffe und verfahren zum thermischen transfer dieser farbstoffe |
US5550098A (en) * | 1991-11-14 | 1996-08-27 | Dai Nippon Printing Co., Ltd. | Thermal transfer sheet |
JPH08108637A (ja) * | 1994-10-13 | 1996-04-30 | Nippon Kayaku Co Ltd | 感熱転写用シート |
US5728201A (en) | 1995-09-14 | 1998-03-17 | Canon Kabushiki Kaisha | Ink, and ink-jet recording method and instruments using the same |
US6353094B1 (en) * | 1999-03-22 | 2002-03-05 | Ciba Specialty Chemicals Corporation | Dyes, a process for their preparation and their use |
-
2002
- 2002-02-28 EP EP02702379A patent/EP1368431B1/en not_active Expired - Lifetime
- 2002-02-28 JP JP2002571768A patent/JP4380990B2/ja not_active Expired - Lifetime
- 2002-02-28 KR KR10-2003-7011764A patent/KR20030090664A/ko not_active Application Discontinuation
- 2002-02-28 WO PCT/EP2002/002150 patent/WO2002072707A1/en active IP Right Grant
- 2002-02-28 AT AT02702379T patent/ATE380221T1/de not_active IP Right Cessation
- 2002-02-28 US US10/469,889 patent/US6953846B2/en not_active Expired - Lifetime
- 2002-02-28 BR BR0207944-5A patent/BR0207944A/pt not_active IP Right Cessation
- 2002-02-28 DE DE60223907T patent/DE60223907T2/de not_active Expired - Lifetime
- 2002-02-28 MX MXPA03006339A patent/MXPA03006339A/es active IP Right Grant
- 2002-02-28 CN CNB028061977A patent/CN1288211C/zh not_active Expired - Lifetime
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102127012A (zh) * | 2009-12-25 | 2011-07-20 | 住友化学株式会社 | 吡啶酮化合物 |
Also Published As
Publication number | Publication date |
---|---|
ATE380221T1 (de) | 2007-12-15 |
CA2434837A1 (en) | 2002-09-19 |
DE60223907T2 (de) | 2008-10-16 |
US6953846B2 (en) | 2005-10-11 |
EP1368431A1 (en) | 2003-12-10 |
MXPA03006339A (es) | 2003-10-06 |
WO2002072707A1 (en) | 2002-09-19 |
KR20030090664A (ko) | 2003-11-28 |
JP2004526836A (ja) | 2004-09-02 |
DE60223907D1 (de) | 2008-01-17 |
US20040123403A1 (en) | 2004-07-01 |
CN1496388A (zh) | 2004-05-12 |
JP4380990B2 (ja) | 2009-12-09 |
BR0207944A (pt) | 2004-07-27 |
EP1368431B1 (en) | 2007-12-05 |
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