CN106590027B - Disperse dye composition and preparation method and application thereof - Google Patents
Disperse dye composition and preparation method and application thereof Download PDFInfo
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- CN106590027B CN106590027B CN201611269697.8A CN201611269697A CN106590027B CN 106590027 B CN106590027 B CN 106590027B CN 201611269697 A CN201611269697 A CN 201611269697A CN 106590027 B CN106590027 B CN 106590027B
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- dye composition
- disperse dye
- component
- compounds
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- 239000000203 mixture Substances 0.000 title claims abstract description 100
- 239000000986 disperse dye Substances 0.000 title claims abstract description 81
- 238000002360 preparation method Methods 0.000 title claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical class ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000000463 material Substances 0.000 claims abstract description 19
- 238000004043 dyeing Methods 0.000 claims abstract description 17
- -1 aromatic amine compounds Chemical class 0.000 claims abstract description 15
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012535 impurity Substances 0.000 claims abstract description 3
- 238000005859 coupling reaction Methods 0.000 claims description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
- 238000003756 stirring Methods 0.000 claims description 42
- 238000001914 filtration Methods 0.000 claims description 38
- 238000010438 heat treatment Methods 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 35
- 238000001816 cooling Methods 0.000 claims description 31
- 238000005406 washing Methods 0.000 claims description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 238000004537 pulping Methods 0.000 claims description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 13
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- RULKYXXCCZZKDZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RULKYXXCCZZKDZ-UHFFFAOYSA-N 0.000 claims description 11
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 claims description 11
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 claims description 11
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- 238000007865 diluting Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000002270 dispersing agent Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 239000000440 bentonite Substances 0.000 claims description 6
- 229910000278 bentonite Inorganic materials 0.000 claims description 6
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000011736 potassium bicarbonate Substances 0.000 claims description 6
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 6
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 235000011181 potassium carbonates Nutrition 0.000 claims description 6
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- 235000017550 sodium carbonate Nutrition 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 claims description 5
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 claims description 5
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 claims description 5
- 239000012752 auxiliary agent Substances 0.000 claims description 5
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 claims description 5
- 238000005469 granulation Methods 0.000 claims description 5
- 230000003179 granulation Effects 0.000 claims description 5
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000004576 sand Substances 0.000 claims description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 4
- BMIPMKQAAJKBKP-UHFFFAOYSA-N 2,4,5-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C=C1C BMIPMKQAAJKBKP-UHFFFAOYSA-N 0.000 claims description 3
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 claims description 3
- PFRYFZZSECNQOL-UHFFFAOYSA-N 2-methyl-4-[(2-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C(=CC=CC=2)C)=C1 PFRYFZZSECNQOL-UHFFFAOYSA-N 0.000 claims description 3
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 3
- DSBIJCMXAIKKKI-UHFFFAOYSA-N 5-nitro-o-toluidine Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N DSBIJCMXAIKKKI-UHFFFAOYSA-N 0.000 claims description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 3
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 claims description 3
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 claims description 2
- AVSIMRGRHWKCAY-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-methylbenzene Chemical compound CC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl AVSIMRGRHWKCAY-UHFFFAOYSA-N 0.000 claims description 2
- ZLELNPSBDOUFHN-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-methylbenzene Chemical compound CC1=CC(Cl)=C(Cl)C(Cl)=C1Cl ZLELNPSBDOUFHN-UHFFFAOYSA-N 0.000 claims description 2
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 claims description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 claims description 2
- KEWNKZNZRIAIAK-UHFFFAOYSA-N 2,3,5,6-tetrachlorophenol Chemical compound OC1=C(Cl)C(Cl)=CC(Cl)=C1Cl KEWNKZNZRIAIAK-UHFFFAOYSA-N 0.000 claims description 2
- WWGQHTJIFOQAOC-UHFFFAOYSA-N 2,3,5-trichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1Cl WWGQHTJIFOQAOC-UHFFFAOYSA-N 0.000 claims description 2
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 claims description 2
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 claims description 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 claims description 2
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 claims description 2
- NMDKWAQVRNUKQH-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid formaldehyde Chemical compound C=O.C(C1=CC=CC=C1)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O NMDKWAQVRNUKQH-UHFFFAOYSA-N 0.000 claims description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims description 2
- GBNHEBQXJVDXSW-UHFFFAOYSA-N 3,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1 GBNHEBQXJVDXSW-UHFFFAOYSA-N 0.000 claims description 2
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 claims description 2
- VPOMSPZBQMDLTM-UHFFFAOYSA-N 3,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1 VPOMSPZBQMDLTM-UHFFFAOYSA-N 0.000 claims description 2
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 claims description 2
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 claims description 2
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 claims description 2
- 229920001732 Lignosulfonate Polymers 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- WQHQCQSAAOGHQP-UHFFFAOYSA-N formaldehyde;2-methylnaphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WQHQCQSAAOGHQP-UHFFFAOYSA-N 0.000 claims description 2
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 claims description 2
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 claims description 2
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- 235000011118 potassium hydroxide Nutrition 0.000 claims 1
- 235000011121 sodium hydroxide Nutrition 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 16
- 230000007613 environmental effect Effects 0.000 abstract description 15
- 150000002989 phenols Chemical class 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 84
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 66
- 230000008878 coupling Effects 0.000 description 51
- 238000010168 coupling process Methods 0.000 description 51
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 40
- 239000000975 dye Substances 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000004321 preservation Methods 0.000 description 19
- 239000000543 intermediate Substances 0.000 description 18
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- 230000009466 transformation Effects 0.000 description 13
- 238000010790 dilution Methods 0.000 description 12
- 239000012895 dilution Substances 0.000 description 12
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 12
- 238000003825 pressing Methods 0.000 description 12
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 9
- 238000001514 detection method Methods 0.000 description 9
- 238000007639 printing Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000004753 textile Substances 0.000 description 9
- 239000002518 antifoaming agent Substances 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- LHRIICYSGQGXSX-UHFFFAOYSA-N 2-chloro-4,6-dinitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1[N+]([O-])=O LHRIICYSGQGXSX-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 238000000227 grinding Methods 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- RTTKVNNZRGYCTK-UHFFFAOYSA-N CC=1C=C(O)N(C)C(=O)C=1C#N Chemical compound CC=1C=C(O)N(C)C(=O)C=1C#N RTTKVNNZRGYCTK-UHFFFAOYSA-N 0.000 description 5
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- 229940051841 polyoxyethylene ether Drugs 0.000 description 4
- 229920000056 polyoxyethylene ether Polymers 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- 239000010865 sewage Substances 0.000 description 4
- 150000003377 silicon compounds Chemical class 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 3
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- KWMDHCLJYMVBNS-UHFFFAOYSA-N 2-bromo-4,6-dinitroaniline Chemical group NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KWMDHCLJYMVBNS-UHFFFAOYSA-N 0.000 description 2
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- ZSUMNJYQUKCOBV-UHFFFAOYSA-N chembl1469934 Chemical group CCN1C(O)=CC(C)=C(C#N)C1=O ZSUMNJYQUKCOBV-UHFFFAOYSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- FPUKYOSOAAPHTN-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1 FPUKYOSOAAPHTN-UHFFFAOYSA-N 0.000 description 2
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- 238000005070 sampling Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BIUJUQPNUIACCY-UHFFFAOYSA-N (3-acetamido-n-acetyloxy-2-ethylanilino) acetate Chemical compound CCC1=C(NC(C)=O)C=CC=C1N(OC(C)=O)OC(C)=O BIUJUQPNUIACCY-UHFFFAOYSA-N 0.000 description 1
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 1
- SZJBQSXXLJETCD-UHFFFAOYSA-N 2-[(2-aminophenyl)methoxymethyl]aniline Chemical compound NC1=CC=CC=C1COCC1=CC=CC=C1N SZJBQSXXLJETCD-UHFFFAOYSA-N 0.000 description 1
- XQGHEXBVXWBMGC-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)anilino]ethyl acetate Chemical compound CC(=O)OCCN(CCOC(C)=O)C1=CC=CC=C1 XQGHEXBVXWBMGC-UHFFFAOYSA-N 0.000 description 1
- ZTTPWPKJVSSSMW-UHFFFAOYSA-N 3-(n-benzylanilino)propanenitrile Chemical compound C=1C=CC=CC=1N(CCC#N)CC1=CC=CC=C1 ZTTPWPKJVSSSMW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- HLCFCDAQLGIKLZ-UHFFFAOYSA-N [5-acetamido-N-(acetyloxymethyl)-2-methoxyanilino]methyl acetate Chemical compound C(C)(=O)OCN(C1=C(C=CC(=C1)NC(=O)C)OC)COC(C)=O HLCFCDAQLGIKLZ-UHFFFAOYSA-N 0.000 description 1
- NGYOVXUBIWJNIU-UHFFFAOYSA-N benzenesulfonate;phenylazanium Chemical compound NC1=CC=CC=C1.OS(=O)(=O)C1=CC=CC=C1 NGYOVXUBIWJNIU-UHFFFAOYSA-N 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000005303 weighing 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/19—Nitro dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/004—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using dispersed dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
A disperse dye composition and a preparation method and application thereof, the disperse dye composition comprises a component A consisting of one or more compounds in a compound shown as a formula (1), a component B consisting of one or more compounds in a compound shown as a formula (2), forbidden aromatic amine compounds, chlorinated phenols, chlorobenzene and chlorotoluene, optional auxiliary materials and other inevitable impurities, wherein the total content of the forbidden aromatic amine compounds is less than 10ppm, the total content of each chlorinated phenol is less than 0.5ppm, and the total content of the chlorobenzene and the chlorotoluene is less than 1ppm. Various environmental protection indexes of the disperse dye composition meet the requirements of Oeko-Tex Standard 100 (2016). In addition, after the disperse dye composition is used for dyeing the fabric, the dyed fabric meets the requirements of Oeko-Tex Standard 100(2016) baby grade.
Description
Technical Field
The invention relates to a disperse dye composition, a preparation method and application thereof. The disperse dye composition is suitable for dyeing or printing terylene and blended fabrics thereof.
Background
The environment-friendly dye has a limit on the content of substances harmful to human bodies, however, most of the environment-friendly dyes are used for environment-friendly control of textile fabrics, namely, the dye on the textile fabrics is measured to control the content of the harmful substances. Therefore, the problem that the ecological environment is seriously influenced by the sewage and sludge of a printing and dyeing mill due to the high content of harmful substances in dye chemicals used for dyeing still exists. Meanwhile, the content of harmful substances in the textile dye is different due to different textile printing and dyeing processes or different dye consumption, so that the environmental protection result is not ideal. Thus, the printing and dyeing wastewater, the sludge and part of the textile fabric which does not meet the environmental protection requirement cause great loss to the downstream printing and dyeing mill. In order to prevent the above-mentioned things from happening, better protect the environment, ensure the health and safety of consumers, enable enterprises to develop stably and sustainably for a long time, develop and produce the high environment-friendly products of the environmental protection level of chemicals required for dyeing, which is the urgent priority of the disperse dye market, is also a necessary way for the survival and development of enterprises, and is the inevitable trend of the development of disperse dyes.
Disclosure of Invention
The invention aims to provide a chemical environment-friendly disperse dye composition, which not only meets the limit requirement of Oeko-Tex Standard 100(2016) in various environment-friendly indexes, but also has low contents of aromatic amine compounds (AZO), Chlorinated Phenols (CPs), chlorobenzene and chlorotoluene (COCs) in a dye composition chemical product for dyeing. The dyed fabric meets the requirements of Oeko-Tex Standard 100(2016) baby grade. In addition, the dyed sewage also meets the current national environmental protection requirements, and the use is more convenient and reliable.
To this end, the invention provides a disperse dye composition, which is characterized by comprising a component A consisting of one or more compounds in a compound of formula (1), a component B consisting of one or more compounds in a compound of formula (2), a forbidden aromatic amine compound, monochlorophenol, dichlorophenol, trichlorophenol, tetrachlorophenol, pentachlorophenol, chlorobenzene and chlorotoluene, optional auxiliary materials and other inevitable impurities,
in the formula (1), the reaction mixture is,
X1、X2each independently is H, NO2Halogen or CN; preferably, the halogen is selected from Cl or Br;
R1is C1～C4Alkyl groups of (a);
R2、R3each independently is hydrogen, C1～C4Alkyl, substituted C1～C4Alkyl, or C2～C4Alkenyl of (a), said substituted C1～C4The substituents of the alkyl group are selected from-OH, -CN, -OCOR, -OCOC6H5、-COOR、OCOOR、-OC6H5、-C6H5Or C1～C4Each R is independently C1～C4Alkyl groups of (a);
in the formula (2), the reaction mixture is,
X3、X4each independently is-H, -Br, -Cl, -CN, -NO2；
R4、R5Each independently is hydrogen, C1～C4Alkyl, substituted C1～C4Alkyl, or C2～C4Alkenyl of (a), said substituted C1～C4The substituents of the alkyl group are selected from-OH, -CN, -OCOR, -OCOC6H5、-COOR、-OC6H5、-C6H5、-CH2CH2OCH2CH2CN, or C1～C4Each R is independently C1～C4Alkyl groups of (a); when R is4、R5Are respectively-CH2CH3and-CH2CH2CN, X3、X4Is not-Cl at the same time;
wherein the forbidden aromatic amine compound is selected from 4-aminobiphenyl (CAS NO.92-67-1), benzidine (92-87-5), 4-chloro-o-toluidine (95-69-2), 2-naphthylamine (91-59-8), o-aminoazotoluene (97-56-3), 2-amino-4-nitrotoluene (99-55-8), p-chloroaniline (106-47-8), 2, 4-diaminoanisole (615-05-4), 4 ' -diaminodiphenylmethane (101-77-9), 3 ' -dichlorobenzidine (91-94-1), 3 ' -dimethoxybenzidine (119-90-4), 3,3 ' -dimethylbenzidine (119-93-7), 3 ' -dimethyl-4, 4 ' -diaminodiphenylmethane (838-88-0), 2-methoxy-5-methylaniline (120-71-8), 4 ' -diamino-3, 3 ' -dichlorodiphenylmethane (101-14-4), 4 ' -diaminodiphenyl ether (101-80-4), 4 ' -diaminodiphenyl sulfide (139-65-1), o-toluidine (95-53-4), 2, 4-diaminotoluene (95-80-7), 2,4, 5-trimethylaniline (137-17-7), o-aminobenzyl ether (90-04-0), One or more of aminoazobenzene (60-09-3), 2, 4-dimethylaniline (95-68-1) and 2, 6-dimethylaniline (87-62-7).
The total content of the forbidden aromatic amine compounds in the dye composition of the invention is 0-10ppm, as detected by the method of EN14362:2012 (gas chromatography-mass spectrometer GC-MS and high performance liquid chromatography HPLC). That is, the dye composition of the present invention may contain none of the aromatic amine compounds, or one or more of the aromatic amine compounds, but the total content of the aromatic amine compounds is not more than 10 ppm.
The chlorinated phenol is selected from monochlorophenol (2-chlorophenol, 3-chlorophenol, 4-chlorophenol), dichlorophenol (2, 6-dichlorophenol, 2, 4-dichlorophenol, 2, 5-dichlorophenol, 3, 5-dichlorophenol, 2, 3-dichlorophenol, 3, 4-dichlorophenol), trichlorophenol (2,4, 6-trichlorophenol, 2,3, 5-trichlorophenol, 2,4, 5-trichlorophenol, 2,3, 4-trichlorophenol, 3,4, 5-trichlorophenol), tetrachlorophenol (2,3,4, 6-tetrachlorophenol, 2,3,5, 6-tetrachlorophenol, 2,3,4, 5-tetrachlorophenol) and pentachlorophenol.
The dye composition of the present invention contains monochlorophenol, dichlorophenol, trichlorophenol, tetrachlorophenol and pentachlorophenol in a total amount of 0 to 0.5ppm, as measured by the method according to ISO17070:2015 (gas chromatography-mass spectrometer GC-MS). Namely, the dye composition of the present invention may contain none or one or more of the chlorinated phenols, but the total content of the monochlorophenol, dichlorophenol, trichlorophenol, tetrachlorophenol and pentachlorophenol is not more than 0.5 ppm. Preferably 0-0.05 pm.
The chlorobenzene and chlorotoluene are selected from one or more of monochlorobenzene, dichlorobenzene, trichlorobenzene, tetrachlorobenzene, pentachlorobenzene, hexachlorobenzene, monochlorobenzene, dichlorotoluene, trichlorotoluene, tetrachlorotoluene and pentachlorotoluene.
The total content of chlorobenzene and chlorotoluene in the dye composition is 0-1ppm determined by referring to the method of GB/T24167-2009 (solvent extraction, GC-MS). Namely, the dye composition of the present invention may contain none of the chlorobenzene and chlorotoluene, or one or more of the chlorobenzene and chlorotoluene, but the total content of the chlorobenzene and chlorotoluene does not exceed 1ppm. Preferably 0 to 0.1ppm.
Preferably, the component A is selected from one or more of the compounds (1-1) to (1-4),
preferably, the component B is selected from one or more compounds of formulae (2-1) to (2-10),
the disperse dye composition can also further comprise a component C consisting of one or more compounds in the compound shown in the formula (3) and an optional component D consisting of one or more compounds in the compound shown in the formula (4),
in the formula (3), the reaction mixture is,
X5is halogen or CN, preferably the halogen is selected from Cl or Br;
R6is C1～C4Alkoxy group of (a);
R7is C1～C4Alkyl groups of (a);
R8、R9each independently is hydrogen, C1～C4Alkyl or substituted C1～C4Or C2～C4Alkenyl of (a), said substituted C1～C4The substituents of the alkyl group are selected from-OH, -CN, -OCOR, -OCOC6H5、-COOR、OCOOR、-OC6H5、-C6H5Or C1～C4Each R is independently C1～C4Alkyl groups of (a);
in the formula (4), the reaction mixture is,
X6、X7each independently is-H, -NO2、-Cl、-OCH3、-OSO2-Ph、-COOC2H4OC2H4OCH3Wherein Ph represents a phenyl group;
R10is optionally substituted by C1～C4Alkoxy-substituted C1～C4An alkyl group.
Preferably, the component C is selected from one or more compounds of formulae (3-1) to (3-12),
preferably, the component D is selected from one or more compounds of formulae (4-1) to (4-9),
preferably, the content of the component A in the disperse dye composition is 1 to 99 parts by weight, preferably 20 to 99 parts by weight, and more preferably 40 to 95 parts by weight; the content of the component B is 1 to 99 parts by weight, preferably 1 to 80 parts by weight, more preferably 5 to 60 parts by weight; the content of the component C is 0 to 90 parts by weight, preferably 10 to 87 parts by weight; the content of component D is 0 to 20 parts by weight, preferably 0.1 to 10 parts by weight.
Preferably, the disperse dye composition comprises one or two of the compounds of formulas (1-1) to (1-2), a compound of formula (2-1) and optionally one or more of the compounds of formulas (3-1) to (3-4).
Preferably, the disperse dye composition comprises a compound of formula (1-1) and a compound of formula (2-9).
Preferably, the disperse dye composition comprises: 10 to 40 parts by weight of component A consisting of one or more compounds of the formula (1), 3 to 50 parts by weight of component B consisting of one or more compounds of the formula (2) and 10 to 87 parts by weight of component C consisting of one or more compounds of the formula (3);
preferably, the auxiliary materials comprise an auxiliary agent and water. Preferably, the weight ratio of the auxiliary agent to the total weight of the component A, the component B, the optional component C and the optional component D is 0.3-6.5: 1.
Preferably, the dispersant is selected from one or more of naphthalene sulfonic acid formaldehyde condensate (dispersant NNO), methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF), benzyl naphthalene sulfonic acid formaldehyde condensate (dispersant CNF), and lignosulfonates (lignin 83A, lignin 85A). Preferably, the dye assistant is anhydrous sodium sulphate.
The disperse dye composition can be liquid after being ground by a sand mill or a grinding machine, and the solid content is 20-50%, or the disperse dye composition is prepared into powder or granules after being spray-dried, and the solid content is 87-96%.
The invention also provides a method for preparing the disperse dye composition, which is characterized by comprising the following steps: (1) adding a compound shown as a formula (P) into water, pulping, adding alkali to adjust the pH value to 10-13, heating to 50-80 ℃, preserving heat for 30-60 minutes, filtering, washing with water, drying, diazotizing, and performing coupling reaction with a compound shown as a formula (Q) to obtain a product I; preferably, the base is selected from one or more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, lithium hydroxide, aluminum hydroxide, methylamine, ethylamine and triethylamine;
or diazotizing the compound shown in the formula (P), diluting with ice and/or water, controlling the temperature to be below 5 ℃, adding diatomite, bentonite or active carbon, stirring, filtering, and performing coupling reaction with the compound shown in the formula (Q) to obtain a product I; wherein, in the formula (P), X1、X2As defined above; in the formula (Q), R1、R2、R3As defined above;
(2) diazotizing a compound shown in a formula (Z), adding ice and/or water for diluting, cooling to below 5 ℃, adding diatomite, bentonite or active carbon for stirring and filtering, and performing coupling reaction with a compound shown in a formula (H) to obtain a product II; wherein, in the formula (Z), X3、X4As defined in claims 1-6; in the formula (H), R4、R5As defined in claims 1-6;
mixing one or more of the obtained products I with one or more of the obtained products II and optional auxiliary materials, and taking the obtained mixture as a disperse dye composition;
optionally, the method further comprises the following steps: adding a compound shown as a formula (X) into water, pulping, adding alkali to adjust the pH value to 10-13, heating to 50-80 ℃, preserving heat for 30-60 minutes, filtering, washing with water, drying, diazotizing, and performing coupling reaction with a compound shown as a formula (Y) to obtain a product III; preferably, the base is selected from one or more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, lithium hydroxide, aluminum hydroxide, methylamine, ethylamine and triethylamine; wherein, in the formula (X), X5As defined above; in the formula (Y), R6、R7、R8、R9As defined above;
mixing one or more of the obtained products III with one or more selected from the products I and one or more selected from the products II and optional auxiliary materials, and taking the mixture as a disperse dye composition;
optionally, the method further comprises the following steps: adding a compound shown as a formula (M) into water, pulping, adding alkali to adjust the pH value to 10-13, heating to 50-80 ℃, preserving heat for 30-60 minutes, filtering, washing with water, drying, diazotizing, and performing coupling reaction with a compound shown as a formula (N) to obtain a product IV; wherein, in the formula (M), X6、X7Each independently is-OSO2-Ph、-COOC2H4OC2H4OCH3In the formula (N), R10Is optionally substituted by C1～C4Alkoxy-substituted C1～C4An alkyl group; preferably, the base is selected from one or more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, lithium hydroxide, aluminum hydroxide, methylamine, ethylamine and triethylamine;
or adding water into the compound shown in the formula (M), crushing, distilling, stopping distilling when the fraction reaches more than 20% of the added water amount, cooling to below 40 ℃, adding hydrochloric acid, pulping, diazotizing to obtain diazonium salt, and performing coupling reaction with the compound shown in the formula (N) to obtain a product IV; wherein, in the formula (M), X6、X7Each independently is-H, -NO2、-Cl、-OCH3In the formula (N), R10Is optionally substituted by C1～C4Alkoxy-substituted C1～C4An alkyl group, a carboxyl group,
and mixing one or more of the obtained products IV with one or more selected from the products I, one or more selected from the products II and one or more optional auxiliary materials selected from the products III, and taking the mixture as a disperse dye composition.
In the above preparation method, one or more of the products I and one or more selected from the products II, optionally one or more selected from the products III and optionally one or more selected from the products IV may be subjected to granulation treatment in the presence of an auxiliary material to prepare a liquid or dried to prepare a disperse dye composition;
or one or more of the products I and one or more selected from the products II, and optionally one or more selected from the products III and optionally one or more selected from the products IV are respectively subjected to granulation treatment in the presence of auxiliary materials, and then are mixed to prepare liquid or dried to prepare the disperse dye composition.
Preferably, the granulation treatment is performed using a sand mill or a grinder.
Preferably, the drying is spray drying.
More preferably, the preparation method of the disperse dye composition comprises the following steps:
a) adding a compound shown as a formula (P) into water, pulping, adding alkali to adjust the pH value to 10-13, heating to 50-80 ℃, preserving heat for 30-60 minutes, filtering, washing and drying; preferably, the base is selected from one or more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, lithium hydroxide, aluminum hydroxide, methylamine, ethylamine and triethylamine;
b) adding sulfuric acid into a diazo kettle, starting the diazo kettle, stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature to be not more than 40 ℃, cooling to 20-30 ℃ after adding, slowly and uniformly adding the compound shown in the formula (P) treated in the step (a), and keeping the temperature at 20-30 ℃ for reaction for 4-8 hours after adding to obtain a diazo component for later use;
c) adding water, sulfuric acid and an emulsifier into a coupling kettle, preferably, the emulsifier is selected from one or more of fatty alcohol-polyoxyethylene ether, adding a coupling component shown in formula (Q), stirring for 30-60 minutes, adding ice and a defoaming agent, preferably, the defoaming agent is selected from one or more of isooctanol or an organic silicon compound, controlling the temperature to be below 10 ℃, dropwise adding a diazo component for standby, dropwise adding for 3-6 hours, controlling the temperature to be 10-15 ℃ after adding, carrying out heat preservation reaction for 2-4 hours, slowly heating to 50-80 ℃ for crystal transformation, filtering and washing with water to obtain a product I;
or,
a) adding sulfuric acid into a diazo kettle, starting the diazo kettle, stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature to be not more than 40 ℃, cooling to 20-30 ℃ after adding, slowly and uniformly adding an intermediate shown in the formula (P), and keeping the temperature at 20-30 ℃ for reaction for 4-8 hours after adding to obtain a diazo component for later use;
b) adding water, ice and sulfuric acid into a diazo dilution kettle, cooling to below 5 ℃, pressing in the diazo component for dilution, controlling the dilution temperature to be below 5 ℃, adding diatomite, bentonite or active carbon after pressing, stirring for 30-60 minutes, filtering, and pumping the diazo filtrate into a coupling kettle;
c) after the diazo filtrate is added, starting a coupling kettle to stir, adding ice, urea or sulfamic acid and an emulsifier, preferably, the emulsifier is selected from one or more of fatty alcohol-polyoxyethylene ether, stirring for 15-60 minutes, adding a defoaming agent, preferably, the defoaming agent is selected from one or more of isooctanol or an organic silicon compound, controlling the temperature below 10 ℃, dropwise adding the coupling component shown in the formula (Q), dropwise adding for 2-5 hours, controlling the temperature to 10-15 ℃ after the addition is finished, carrying out heat preservation reaction for 2-5 hours, slowly heating to 50-80 ℃ for crystal transformation, filtering and washing to obtain a product I;
and, comprising the steps of:
a) adding sulfuric acid into a diazo kettle, starting the diazo kettle, stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature to be not more than 40 ℃, cooling to 20-30 ℃ after adding, slowly and uniformly adding an intermediate shown in the formula (Z), and keeping the temperature at 20-30 ℃ for reaction for 4-8 hours after adding to obtain a diazo component for later use;
b) adding water, ice and sulfuric acid into a diazo dilution kettle, cooling to below 5 ℃, pressing in the diazo component for dilution, controlling the dilution temperature to be below 5 ℃, adding diatomite, bentonite or active carbon after pressing, stirring for 30-60 minutes, filtering, and pumping the diazo filtrate into a coupling kettle;
c) after the diazo filtrate is added, starting a coupling kettle to stir, adding ice, urea or sulfamic acid and an emulsifier, preferably, the emulsifier is selected from one or more of fatty alcohol-polyoxyethylene ether, stirring for 15-60 minutes, adding a defoaming agent, preferably, the defoaming agent is selected from one or more of isooctanol or an organic silicon compound, controlling the temperature below 10 ℃, dropwise adding the coupling component shown in the formula (H), dropwise adding for 2-5 hours, controlling the temperature to 10-15 ℃ after adding, carrying out heat preservation reaction for 2-5 hours, slowly heating to 50-80 ℃ for crystal transformation, filtering and washing to obtain a product II;
and mixing one or more of the obtained products II with one or more of the products I and optional auxiliary materials, and taking the obtained mixture as the disperse dye composition.
Optionally, further comprising the steps of:
a) adding a compound shown as a formula (X) into water, pulping, adding alkali to adjust the pH value to 10-13, heating to 50-80 ℃, preserving heat for 30-60 minutes, filtering, washing and drying; preferably, the base is selected from one or more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, lithium hydroxide, aluminum hydroxide, methylamine, ethylamine and triethylamine;
b) adding sulfuric acid into a diazo kettle, starting the diazo kettle, stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature to be not more than 40 ℃, cooling to 20-30 ℃ after adding, slowly and uniformly adding the compound shown in the formula (X) treated in the step a), keeping the temperature at 25-30 ℃ for reaction for 4-8 hours after adding, and obtaining a diazo component for later use;
c) adding water, sulfuric acid and an emulsifier into a coupling kettle, preferably, the emulsifier is selected from one or more of fatty alcohol-polyoxyethylene ether, adding a coupling component shown in a formula (Y), stirring for 30-60 minutes, adding ice and a defoaming agent, preferably, the defoaming agent is selected from one or more of isooctanol or an organic silicon compound, controlling the temperature to be below 10 ℃, dropwise adding a diazo component for standby, dropwise adding for 3-6 hours, controlling the temperature to be 10-15 ℃ after adding, carrying out heat preservation reaction for 2-4 hours, slowly heating to 50-80 ℃ for crystal transformation, filtering and washing to obtain a product III;
mixing one or more of the obtained products III with one or more of the products I and one or more of the products II and optional auxiliary materials to obtain a mixture serving as a disperse dye composition;
optionally, further comprising the steps of:
a) adding a compound shown as a formula (M) into water for pulping, and adding alkali to adjust the pH value to 10-13; heating to 50-80 ℃, preserving heat for 30-60 minutes, filtering, washing and drying;
b) putting water and the compound shown in the formula (M) treated in the step a) into a diazo kettle, adding hydrochloric acid, pulping for 1-3 hours, adding water to adjust the volume, adding ice to reduce the temperature to be below 5 ℃, slowly adding a sodium nitrite solution with the mass concentration of 20-30%, after the addition is finished, preserving the temperature at 8 ℃ for 1-3 hours to obtain a diazo component for later use;
c) adding water and a buffering agent (such as sodium acetate, disodium hydrogen phosphate and the like) with the pH value of about 9 into a coupling kettle, stirring for 15-60 minutes, putting the coupling component shown in formula (N), pulping for 30-60 minutes, adding ice, cooling to below 15 ℃, dropwise adding a ready-to-use diazo component for 1-3 hours, preserving the temperature for 1-3 hours at 15-20 ℃ after dropwise adding, heating to 50-80 ℃ for crystal transformation, filtering and washing to obtain a product IV;
or,
a) adding water into a kettle, grinding and crushing a compound shown as a formula (M) through a colloid mill, adding the compound into a refining kettle, heating and distilling, stopping distilling when the fraction is 20% of the added water amount, cooling to below 40 ℃, adding hydrochloric acid, and pulping for 1-3 hours;
b) adding the compound shown in the formula (M) treated in the step a) into a diazo kettle, adding water, adding ice, cooling to below 5 ℃, slowly adding a sodium nitrite solution with the mass concentration of 20-30%, and after the addition is finished, carrying out heat preservation reaction at below 8 ℃ for 1-3 hours to obtain a diazo component for later use;
c) adding water and sodium acetate into a coupling kettle, stirring for 15-60 minutes, throwing a coupling component shown in formula (N), pulping for 30-60 minutes, adding ice, cooling to below 15 ℃, dropwise adding a ready-to-use diazo component for 1-3 hours, keeping the temperature for 1-3 hours at 15-20 ℃ after dropwise adding is finished, heating to 50-80 ℃ for crystal transformation, filtering and washing to obtain a product IV;
mixing one or more prepared products IV with one or more selected from the products I and one or more selected from the products II, and optionally one or more selected from the products III, and optionally auxiliary materials, and taking the obtained mixture as a disperse dye composition.
The invention also provides the use of the disperse dye composition for dyeing or printing fabrics; preferably, the fabric is polyester or polyester blend fabric.
The invention also provides a fabric which is characterized by being prepared by adopting the disperse dye composition to dye or print; preferably, the fabric is polyester or polyester blend fabric.
Effects of the invention
The disperse dye composition is a chemical environment-friendly disperse dye composition, and not only meets the limited requirement of Oeko-Tex Standard 100(2016), but also has the advantages that the content of forbidden aromatic amine compounds is not more than 10ppm, the total content of monochlorophenol, dichlorophenol, trichlorophenol, tetrachlorophenol and pentachlorophenol is not more than 0.5ppm, and the total content of chlorobenzene and chlorotoluene (COCs) is not more than 1ppm. The dyed sewage also meets the environmental protection requirement, and the use is more convenient and reliable.
On the other hand, under the condition that the disperse dye composition meets the requirement of environmental protection, no matter how a printing and dyeing process is changed by a downstream printing and dyeing enterprise or the maximum use amount of the dye is used, the environmental protection of the textile can be guaranteed in an all-around way. After the disperse dye composition is adopted to dye fabrics, the dyed fabrics meet the requirements of Oeko-Tex Standard 100(2016) baby grade, particularly, the total content of forbidden aromatic amine compounds can reach below 5ppm, the total content of monochlorophenol, dichlorophenol, trichlorophenol, tetrachlorophenol and pentachlorophenol is below 0.05ppm, and the total content of chlorobenzene and chlorotoluene is below 0.1ppm. Meanwhile, the printing and dyeing sewage and sludge meet the environmental protection requirement, the environmental protection treatment cost is saved, and a solid foundation is laid for enterprise development, ecological environment protection and sustainable development.
Detailed Description
The present invention is further illustrated by the following examples, but the scope of the present invention is not limited thereto.
Preparation example 1
a) Adding the intermediate 2, 4-dinitro-6-chloroaniline into water, pulping, adding 30% sodium hydroxide solution, adjusting the pH to 11, heating to 60 ℃, preserving heat for 30 minutes, filtering, washing and drying;
b) adding sulfuric acid into a diazo kettle, starting stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature not to exceed 40 ℃, cooling to 20 ℃ after adding, slowly and uniformly adding the 2, 4-dinitro-6-chloroaniline treated in the step a), and carrying out heat preservation and diazotization reaction for 6 hours at 25-30 ℃ after adding to obtain a diazo component for later use;
c) adding water, sulfuric acid and peregal into a coupling kettle, adding coupling component N, N-diethyl m-acetamino aniline, stirring for 30 minutes, adding ice and isooctanol, controlling the temperature to be below 10 ℃, dropwise adding a ready-to-use diazo component for about 5 hours, after the addition is finished, controlling the temperature to be 10-15 ℃, carrying out heat preservation reaction for 2 hours, slowly heating to 60 ℃ for crystal transformation, filtering and washing to obtain a product (I-1). The resulting product (I-1) contains the structure of the formula (1-1) as component A.
Preparation example 2
The product (I-2) was obtained by the same procedure as in preparation example 1, except that 2, 4-dinitro-6-chloroaniline, the intermediate in preparation example 1, was replaced with 2, 4-dinitro-6-bromoaniline. The resulting product (I-2) contains the structure of formula (1-2) as component A.
Preparation example 3
a) Adding sulfuric acid into a diazo kettle, starting stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature not to exceed 40 ℃, cooling to 10 ℃ after the addition is finished, slowly and uniformly adding an intermediate p-nitroaniline for about 3 hours, and preserving heat for 2.5 hours after the addition is finished to obtain a diazo component for later use;
b) adding water and ice into a diazo dilution kettle, cooling to below 5 ℃, pressing in the diazo liquid for dilution, controlling the dilution temperature to be below 5 ℃, adding activated carbon after pressing, stirring for 30 minutes, filtering, and pumping the diazo filtrate into a coupling kettle;
c) and (3) after the diazo filtrate is added, starting a coupling kettle and stirring, adding urea and peregal, adding a coupling component N, N-diacetoxyethyl meta-acetaminophenylamine, adjusting the acidity of the coupling material to 10% (the acidity of sulfuric acid), controlling the reaction temperature to be 15-25 ℃, carrying out heat preservation reaction for 4 hours, slowly heating to 30-35 ℃, carrying out heat preservation for 3 hours, heating to 40-45 ℃, carrying out heat preservation for 2 hours, filtering and washing to obtain a product (I-3). The resulting product (I-3) contains the structure of formula (1-3) as component A.
Preparation example 4
a) Adding sulfuric acid into a diazo kettle, starting stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature to be not more than 40 ℃, cooling to 22 ℃ after the addition is finished, slowly and uniformly adding the intermediate 2-cyano-4-nitroaniline, and keeping the temperature at 25-30 ℃ for reaction for 6 hours for later use.
b) Adding water and ice into a diazo diluting kettle, cooling to below 5 ℃, pressing the mixture into the diazo diluting kettle to be diluted by the diazo liquid, controlling the diluting temperature to be below 5 ℃, adding diatomite after pressing, stirring for 30 minutes, and filtering. The filtrate is injected into a coupling kettle.
c) Coupling: after the diazo is added, starting a coupling kettle and stirring, adding ice, urea and peregal, stirring for 15 minutes, adding isooctyl alcohol, controlling the temperature below 10 ℃, dropwise adding the coupling component N, N-diacetic acid methyl ester-m-acetamino aniline for about 3 hours, controlling the temperature to 10-15 ℃ after the dropwise adding is finished, carrying out heat preservation reaction for 2 hours, slowly heating to 70 ℃ for crystal transformation, filtering and washing to obtain a product (I-4). The resulting product (I-4) contains the structure of formula (1-4) as component A.
Preparation examples 5 to 15
Preparation examples 5, 7, 8, 11, 12 and 14 the procedure of preparation example 3 was used except that the coupling component N, N-diacetoxyethyl-m-acetaminoaniline of preparation example 3 was replaced with the coupling component shown in Table 1.
And preparations 6, 9, 10 and 13 the method of preparation 4 was used, except that the intermediate 2-cyano-4-nitroaniline, the coupling component N, N-diacetoxymethylmethylaminoacetanilide, were replaced with the intermediate and the coupling component represented by the formula in Table 1.
TABLE 1
Production examples 5 to 14 Components B contained in the products (II-1) to (II-10) obtained in this order are compounds of the formulae (2-1) to (2-10), respectively.
Preparation examples 15 to 18 and 20 to 26
The products (III-1) to (III-4) and (III-6) to (III-12) were prepared in the same manner as in preparation example 1 except that the intermediate 2, 4-dinitro-6-chloroaniline of preparation example 1 and the coupling component N, N-diethyl-m-acetaminoaniline of preparation example 1 were replaced with the intermediate and the coupling component shown in Table 2, respectively.
TABLE 2
Preparation example 20
According to the same manner as in production example 1 except that the intermediate 2, 4-dinitro-6-chloroaniline and the coupling component N, N-diethyl-m-acetaminoaniline of production example 1 were replaced with the intermediate 2, 4-dinitro-6-bromoaniline and the coupling component N, N-diacetoxymethyl-2-methoxy-5-acetaminoaniline, respectively, to produce a raw material cake of formula (3-5); then cyanidation is carried out: adding DMF into a cyaniding kettle, heating to 80 ℃, adding cyaniding ketone and sodium cyanide, heating to 100 ℃, preserving heat for 1 hour, cooling to 80 ℃, adding the raw material filter cake of the formula (3-5), heating to 100-110 ℃, preserving heat for 3 hours, sampling, measuring the reaction end point, cooling to 25 ℃ after the raw material filter cake is qualified, filtering, and washing with water to obtain a cyaniding filter cake; then removing ketone and cyanogen: dissolving ferric trichloride in water, hydrochloric acid and ferric trichloride, adding cyanide filter cake, pulping for 10 hr, filtering, and washing with water to obtain product (III-5).
Preparation examples 15 to 26 successively gave products (III-1) to (III-12) containing compounds of the formulae (3-1) to (3-12), respectively.
Preparation example 27
a) Adding the intermediate m-benzenesulfonate ester aniline into water, pulping, adding 30% sodium hydroxide solution, adjusting pH to 12, heating to 55 deg.C, keeping the temperature for 30 min, filtering, washing with water, and drying;
b) putting water and the m-benzenesulfonic acid ester group aniline treated in the step a) into a diazo kettle, adding hydrochloric acid, pulping for 2 hours, adding water to adjust the volume, adding ice to cool to 5 ℃, slowly adding a sodium nitrite solution with the mass concentration of 30%, after the addition is finished, keeping the temperature at 4-8 ℃ for 2 hours to obtain a diazo component for later use;
c) adding water and sodium acetate into a coupling kettle, stirring for 15 minutes, adding a coupling component of 3-cyano-4-methyl-6-hydroxy-N-methylpyridone, pulping for 60 minutes, adding ice, cooling to 5 ℃, dropwise adding a ready-to-use diazo component for about 1.5 hours, preserving heat for 2 hours at 15-20 ℃ after dropwise adding is finished, heating to 50 ℃ for crystal transformation, filtering and washing to obtain a product (IV-1).
Preparation example 28
The product (IV-2) was obtained by following the same procedures as in preparation example 27, except that 3-cyano-4-methyl-6-hydroxy-N-methylpyridinone, the coupling component in preparation example 27, was replaced with 3-cyano-4-methyl-6-hydroxy-N-ethylpyridinone.
Preparation example 29
a) Adding water into a kettle, grinding and crushing the o-nitroaniline by a colloid mill, adding the mixture into the kettle, heating and distilling, stopping distilling when the fraction is more than 20% of the added water amount, cooling to below 40 ℃, adding hydrochloric acid, and pulping for 1 hour;
b) adding the o-nitroaniline treated in the step a) into a diazo kettle, adding water to adjust the volume, adding ice to reduce the temperature to be below 5 ℃, slowly adding a sodium nitrite solution with the mass concentration of 20%, and after the addition is finished, keeping the temperature below 5-8 ℃ for 2 hours to obtain a diazo component for later use;
c) adding water and sodium acetate into a coupling kettle, stirring for 15 minutes, adding a coupling component of 3-cyano-4-methyl-6-hydroxy-N-methylpyridone, pulping for 30 minutes, adding ice, cooling to 7 ℃, dropwise adding a ready-to-use diazo component for about 2 hours, keeping the temperature for 2 hours at 15-20 ℃ after dropwise adding, heating to 50 ℃ for crystal transformation, filtering and washing to obtain a product (IV-3).
Preparation examples 30 to 34
The products (IV-4) to (IV-8) were prepared by the same procedures as in preparation example 29, except that the intermediate o-nitroaniline of preparation example 29 and the coupling component 3-cyano-4-methyl-6-hydroxy-N-methylpyridinone were replaced with the intermediates and coupling components shown in Table 3, respectively.
TABLE 3
Preparation example 35
The product (IV-9) was obtained by the same procedures as in preparation example 27, except that p-diethylene glycol methyl ether formate aniline and 3-cyano-4-methyl-6-hydroxy-N-ethylpyridone were used instead of the intermediate m-benzenesulfonate aniline and the coupling component 3-cyano-4-methyl-6-hydroxy-N-methylpyridinone in preparation example 27, respectively.
The components D contained in the products (IV-1) to (IV-9) obtained in production examples 27 to 35 are compounds of the formulae (4-1) to (4-9), respectively.
Comparative preparation example 1
a) Adding sulfuric acid into a diazo kettle, starting stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature to be not more than 40 ℃, cooling to 20 ℃ after adding, slowly and uniformly adding diazo component 6-chloro-2, 4-dinitroaniline, and carrying out heat preservation and diazotization reaction for 6 hours at 25-30 ℃ after adding to obtain a diazo component for later use;
b) adding water, sulfuric acid and peregal into a coupling kettle, adding coupling component N, N-diethyl m-acetamino aniline, stirring for 30 minutes, adding ice and isooctanol, controlling the temperature to be below 10 ℃, dropwise adding a ready-to-use diazo component for about 5 hours, after the addition is finished, controlling the temperature to be 10-15 ℃, carrying out heat preservation reaction for 2 hours, slowly heating to 60 ℃ for crystal transformation, filtering and washing to obtain a product (I' -1).
Comparative preparation example 2
a) Adding sulfuric acid into a diazo kettle, starting stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature to be not more than 40 ℃, cooling to 22 ℃ after the addition is finished, slowly and uniformly adding the intermediate 2-cyano-4-nitroaniline, and keeping the temperature at 25-30 ℃ for reaction for 6 hours for later use.
b) Adding water and ice into a diazo diluting kettle, cooling to below 5 ℃, pressing the mixture into the diazo diluting kettle to be diluted by the diazo liquid, controlling the diluting temperature to be below 5 ℃, stirring for 30 minutes after pressing, and filtering. The filtrate is injected into a coupling kettle.
c) And after the filtrate is added, starting a coupling kettle, stirring, adding ice, urea and peregal, stirring for 15 minutes, adding isooctanol, controlling the temperature to be below 10 ℃, dropwise adding the coupling component N, N-diacetoxyethylaniline for about 3 hours, controlling the temperature to be 10-15 ℃ after the addition is finished, carrying out heat preservation reaction for 2 hours, slowly heating to 70 ℃ for crystal transformation, filtering and washing to obtain a product II' -9).
Comparative preparation example 3
a) Adding sulfuric acid into a diazo kettle, starting stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature not to exceed 40 ℃, cooling to 10 ℃ after the addition is finished, slowly and uniformly adding an intermediate p-nitroaniline for about 3 hours, and preserving heat for 2.5 hours after the addition is finished to obtain a diazo component for later use;
b) adding water and ice into a diazo dilution kettle, cooling to below 5 ℃, pressing in the diazo liquid for dilution, controlling the dilution temperature to be not more than 5 ℃, stirring for 30 minutes after pressing, filtering, and pumping the diazo filtrate into a coupling kettle;
c) and (3) after the diazo filtrate is added, starting a coupling kettle and stirring, adding urea and peregal, adding a coupling component N-cyanoethyl-N-benzylaniline, adjusting the acidity of a coupling material to 10% (the acidity of sulfuric acid), controlling the reaction temperature to be 15-25 ℃, carrying out heat preservation reaction for 4 hours, slowly heating to 30-35 ℃, carrying out heat preservation for 3 hours, heating to 40-45 ℃, carrying out heat preservation for 2 hours, filtering and washing to obtain a product (II' -1).
Comparative preparation example 4
a) Adding sulfuric acid into a diazo kettle, starting stirring, slowly adding nitrosyl sulfuric acid, controlling the temperature to be not more than 40 ℃, cooling to 20 ℃ after adding, slowly and uniformly adding diazo component 2, 4-dinitro-6-chloroaniline, and carrying out heat preservation and diazotization reaction for 6 hours at 25-30 ℃ after adding to obtain a diazo component for later use;
b) adding water, sulfuric acid and peregal into a coupling kettle, adding a coupling component N, N-diallyl-2-methoxy-5-acetamido aniline, stirring for 30 minutes, adding ice and isooctanol, controlling the temperature to be below 10 ℃, dropwise adding a ready-to-use diazo component for about 5 hours, controlling the temperature to be 10-15 ℃ after the dropwise adding, carrying out heat preservation reaction for 2 hours, slowly heating to 60 ℃ for crystal transformation, filtering, and washing to obtain a product (III' -1).
Example 1:
90 g of the product (I-1) obtained in preparation example 1, 10 g of the product (II-9) obtained in preparation example 13, 50 g of the dispersant MF, 80 g of the lignin 85A, 345 g of water, stirring uniformly, grinding by a sand mill, and spray-drying to obtain the disperse dye composition.
Comparative example 1:
the same procedures as in example 1 were followed, except that the products (I-1) and (II-9) in example 1 were replaced with the products (I '-1) and (II' -9) obtained in comparative preparation example 1 and comparative preparation example 2.
The finished dyes of example 1 and comparative example 1 were subjected to the following tests, the specific test methods being as follows:
the dye products of example 1 and comparative example 1 were subjected to analytical tests of AZO, CPs, COCs, respectively, with reference to EN14362:2012 (gas chromatography-mass spectrometer GC-MS and high performance liquid chromatography HPLC), ISO17070:2015 (gas chromatography-mass spectrometer GC-MS), GB/T24167-2009 (solvent extraction, gas chromatography-mass spectrometer GC-MS), with the test results shown in table 4:
TABLE 4
Note: (1) detection limit in the dye composition product:
AZO: ND is not detected, the detection limit is 10ppm, ppm is mg/kg, the same applies below;
CPs (complex peptide sequences): ND is not detected, the detection limit is 0.05ppm, ppm is mg/kg, the same applies below;
COCs: ND is not detected, the detection limit is 0.1ppm, ppm is mg/kg, and the same applies below.
(2) The data of the CPs are the detection data of the highest content in the five types of chlorinated phenols, and the same is carried out below.
As can be seen from Table 4, the respective environmental protection indexes of the disperse dye composition product obtained in example 1 are better than those of the disperse dye composition product obtained in comparative example 1.
Example 2:
adding 450 g of water into 20 g of the product (I-1), 44 g of the product (II-1), 36 g of the product (III-1) dye component, 30 g of the dispersant MF and 30 g of the lignin 85A, fully and uniformly stirring, grinding by using a sand mill, and then carrying out spray drying to obtain the black refined disperse dye composition.
Comparative example 2
The procedure of example 2 was followed, except that the product (I-1), the product (II-1) and the product (III-1) were replaced with the product (I ' -1), the product (II ' -1) and the product (III ' -1) obtained in comparative preparation examples 1, 3 and 4, respectively.
The dyes of example 2 and comparative example 2 were subjected to the analytical tests for AZO, CPs, COCs according to the procedure of example 1, and the test results are shown in table 5:
TABLE 5
As can be seen from Table 5, the respective environmental protection indexes of the disperse dye composition product obtained in example 2 are better than those of the disperse dye composition product obtained in comparative example 2.
Examples 3 to 18
Disperse dye compositions were prepared according to the composition formula shown in Table 6 in the same manner as in example 1, and are shown in Table 6.
Table 6: weight unit: g
The disperse dye composition products of examples 3-18 were subjected to the following tests, specifically:
the disperse dye composition products of examples 3 to 18 were tested for AZO, CPs, COCs content according to methods of EN14362:2012 (gas chromatography-mass spectrometer GC-MS and high performance liquid chromatography HPLC), ISO17070:2015 (gas chromatography-mass spectrometer GC-MS), GB/T24167-2009 (solvent extraction, gas chromatography-mass spectrometer GC-MS), respectively, and the test results are shown in table 7:
TABLE 7
The disperse dye composition products prepared by the methods of the preparation examples and the examples of the invention have slightly different environmental protection indexes although different batches are below the required limit, and the environmental protection indexes are independent of the added auxiliary agents and the grinding method.
The finished dyes of examples 4,5, 6, 7, 8, 9, 11 and 14 in table 7 were prepared into disperse dye suspensions by weighing 1 g of the disperse dye compositions of examples 4,5, 6, 7, 8, 9, 11 and 14 into 500ml of water according to the method of GB/T2394-2006. Absorbing 100ml of disperse dye suspension, adjusting the pH value of a dye bath to 5 by using acetic acid, then heating to 60 ℃, simultaneously respectively adding 2g of polyester fibers for high-temperature high-pressure dyeing, heating to 130 ℃ within 35 minutes, preserving heat for 45 minutes, cooling to 80 ℃ and sampling.
The content of AZO, CPs and COCs of the dyed textiles is tested according to EN14362:2012 (gas chromatography-mass spectrometer GC-MS and high performance liquid chromatograph HPLC), ISO17070:2015 (gas chromatography-mass spectrometer GC-MS) and GB/T24167-2009 (solvent extraction, gas chromatography-mass spectrometer GC-MS) methods, and the test results are shown in Table 8.
TABLE 8
| Name (R) | AZO | CPs | COCs |
| Example 4 | ND | ND | ND |
| Example 5 | ND | ND | ND |
| Example 6 | ND | ND | ND |
| Example 7 | ND | ND | ND |
| Example 8 | ND | ND | ND |
| Example 9 | ND | ND | ND |
| Example 11 | ND | ND | ND |
| Example 14 | ND | ND | ND |
Remarking: detection limit in textiles:
ND is not detected, the detection limit is 5ppm, ppm is mg/kg,
CPs ND was not detected, detection limit was 0.05ppm, ppm was mg/kg,
COCs ND was not detected, the detection limit was 0.1ppm, ppm was mg/kg,
as can be seen from tables 6, 7 and 8, the environmental protection indexes of the examples 3 to 18 are all excellent, and AZO, CPs and COCs are not detected in the dyed fabrics after the dyes of the examples 4,5, 6, 7, 8, 9, 11 and 14 are used for dyeing textiles.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and such simple modifications are within the protective scope of the present invention.
Claims (17)
1. A process for the preparation of a disperse dye composition comprising a component A consisting of one or more compounds of the formula (1), a component B consisting of one or more compounds of the formula (2), a forbidden aromatic amine compound, monochlorophenol, dichlorophenol, trichlorophenol, tetrachlorophenol, pentachlorophenol, chlorobenzene and chlorotoluene, optionally adjuvants, and other unavoidable impurities,
the preparation method of the disperse dye composition is characterized by comprising the following steps of: (1) adding a compound shown as a formula (P) into water, pulping, adding alkali to adjust the pH value to 10-13, heating to 50-80 ℃, preserving heat for 30-60 minutes, filtering, washing with water, drying, diazotizing, and performing coupling reaction with a compound shown as a formula (Q) to obtain a product I;
or diazotizing the compound shown in the formula (P), diluting with ice and water, controlling the temperature to be below 5 ℃, adding diatomite, bentonite or active carbon, stirring, filtering, and performing coupling reaction with the compound shown in the formula (Q) to obtain a product I;
(2) diazotizing a compound shown in a formula (Z), adding ice and/or water for diluting, cooling to below 5 ℃, adding diatomite, bentonite or active carbon, stirring, filtering, and carrying out coupling reaction with a compound shown in a formula (H) to obtain a product II;
mixing one or more of the obtained products I with one or more of the obtained products II and optional auxiliary materials, and taking the obtained mixture as a disperse dye composition;
in the formula (1), the formula (P) and the formula (Q),
X1、X2each independently is-H, -NO2-Cl, -Br or-CN;
R1is C1～C4Alkyl groups of (a);
R2、R3each independently is hydrogen, C1～C4Alkyl, substituted C1～C4Alkyl, or C2～C4Alkenyl of (a), said substituted C1～C4The substituents of the alkyl group are selected from-OH, -CN, -OCOR, -OCOC6H5、-COOR、-OCOOR、-OC6H5、-C6H5Or C1～C4Each R is independently C1～C4Alkyl groups of (a);
in the formula (2), the formula (Z) or the formula (H),
X3、X4each independently is-H, -Br, -Cl, -CN, -NO2；
R4、R5Each independently is hydrogen, C1～C4Alkyl, substituted C1～C4Alkyl, or C2～C4Alkenyl of (a), said substituted C1～C4The substituents of the alkyl group are selected from-OH, -CN, -OCOR, -OCOC6H5、-COOR、-OC6H5、-C6H5、-CH2CH2OCH2CH2CN, or C1～C4Each R is independently C1～C4Alkyl groups of (a); when R is4、R5Are respectively-CH2CH3and-CH2CH2CN, X3、X4Is not-Cl at the same time;
wherein the forbidden aromatic amine compound is selected from 4-aminobiphenyl, benzidine, 4-chloro-o-toluidine, 2-naphthylamine, o-aminoazotoluene, 2-amino-4-nitrotoluene, p-chloroaniline, 2, 4-diaminoanisole, 4 '-diaminodiphenylmethane, 3' -dichlorobenzidine, 3 '-dimethoxybenzidine, 3' -dimethylbenzidine, 3 '-dimethyl-4, 4' -diaminodiphenylmethane, 2-methoxy-5-methylaniline, 4 '-diamino-3, 3' -dichlorodiphenylmethane, 4 '-diaminodiphenyl ether, 4' -diaminodiphenyl sulfide, o-toluidine, 2, one or more of 4-diaminotoluene, 2,4, 5-trimethylaniline, o-aminoanisole, p-aminoazobenzene, 2, 4-dimethylaniline and 2, 6-dimethylaniline;
the monochlorophenol is one or more selected from 2-chlorophenol, 3-chlorophenol and 4-chlorophenol; the dichlorophenol is one or more selected from 2, 6-dichlorophenol, 2, 4-dichlorophenol, 2, 5-dichlorophenol, 3, 5-dichlorophenol, 2, 3-dichlorophenol and 3, 4-dichlorophenol; the trichlorophenol is one or more selected from 2,4, 6-trichlorophenol, 2,3, 5-trichlorophenol, 2,4, 5-trichlorophenol, 2,3, 4-trichlorophenol and 3,4, 5-trichlorophenol; the tetrachlorophenol is one or more selected from 2,3,4, 6-tetrachlorophenol, 2,3,5, 6-tetrachlorophenol and 2,3,4, 5-tetrachlorophenol;
the chlorobenzene and chlorotoluene are one or more selected from monochlorobenzene, dichlorobenzene, trichlorobenzene, tetrachlorobenzene, pentachlorobenzene, hexachlorobenzene, monochlorobenzene, dichlorotoluene, trichlorotoluene, tetrachlorotoluene and pentachlorotoluene;
and the total content of the forbidden aromatic amine compounds is 0-10ppm, the total content of the monochlorophenol, the dichlorophenol, the trichlorophenol, the tetrachlorophenol and the pentachlorophenol is 0-0.5ppm, and the total content of the chlorobenzene and the chlorotoluene is 0-1 ppm.
2. The process for producing a disperse dye composition according to claim 1,
the component A is selected from one or more of (1-1) to (1-4) compounds,
the component B is selected from one or more compounds in formulas (2-1) to (2-10),
3. the process for preparing a disperse dye composition according to claim 1, wherein the disperse dye composition further comprises a component C consisting of one or more compounds of formula (3), and optionally a component D consisting of one or more compounds of formula (4),
the preparation method of the disperse dye composition further comprises the following steps: adding a compound shown as a formula (X) into water, pulping, adding alkali to adjust the pH value to 10-13, heating to 50-80 ℃, preserving heat for 30-60 minutes, filtering, washing with water, drying, diazotizing, and performing coupling reaction with a compound shown as a formula (Y) to obtain a product III;
mixing one or more of the obtained products III with one or more selected from the products I and one or more selected from the products II and optional auxiliary materials, and taking the mixture as a disperse dye composition;
when the disperse dye composition further comprises a component D consisting of one or more compounds in the compounds of the formula (4), the preparation method of the disperse dye composition further comprises the following steps: adding a compound shown as a formula (M) into water, pulping, adding alkali to adjust the pH value to 10-13, heating to 50-80 ℃, preserving heat for 30-60 minutes, filtering, washing with water, drying, diazotizing, and performing coupling reaction with a compound shown as a formula (N) to obtain a product IV; wherein, in the formula (M), X6、X7Each independently is-OSO2-Ph、-COOC2H4OC2H4OCH3In the formula (N), R10Is optionally substituted by C1～C4Alkoxy-substituted C1～C4An alkyl group;
or adding water into the compound shown in the formula (M), crushing, distilling, stopping distilling when the fraction reaches more than 20% of the added water amount, cooling to below 40 ℃, adding hydrochloric acid, pulping, diazotizing to obtain diazonium salt, and performing coupling reaction with the compound shown in the formula (N) to obtain a product IV; wherein, in the formula (M), X6、X7Each independently is-H, -NO2、-Cl、-OCH3In the formula (N), R10Is optionally substituted by C1～C4Alkoxy-substituted C1～C4An alkyl group, a carboxyl group,
mixing one or more of the obtained products IV with one or more selected from the products I and one or more selected from the products II and one or more selected from the products III and optional auxiliary materials, and taking the mixture as a disperse dye composition;
wherein in the formula (3), the formula (X) and the formula (Y),
X5is-Cl, -Br or-CN;
R6is C1～C4Alkoxy group of (a);
R7is C1～C4Alkyl groups of (a);
R8、R9each independently is hydrogen, C1～C4Alkyl, substituted C1～C4Alkyl, or C2～C4Alkenyl of (a), said substituted C1～C4The substituents of the alkyl group are selected from-OH, -CN, -OCOR, -OCOC6H5、-COOR、-OCOOR、-OC6H5、-C6H5Or C1～C4Each R is independently C1～C4Alkyl groups of (a);
in the formula (4), the reaction mixture is,
X6、X7each independently is-H, -NO2、-Cl、-OCH3、-OSO2-Ph、-COOC2H4OC2H4OCH3Wherein Ph represents a phenyl group;
R10is optionally substituted by C1～C4Alkoxy-substituted C1～C4An alkyl group.
4. The process for producing a disperse dye composition according to claim 3, wherein the component C is one or more compounds selected from the group consisting of the compounds of the formulae (3-1) to (3-12),
the component D is selected from one or more compounds in formulas (4-1) to (4-9),
5. the method for preparing a disperse dye composition according to any one of claims 1 to 4, wherein the disperse dye composition contains component A in an amount of 1 to 99 parts by weight; the content of the component B is 1 to 99 weight parts; the content of the component C is 0 to 90 weight portions; the content of the component D is 0 to 20 weight portions.
6. A process for preparing a disperse dye composition according to claim 5, wherein in the disperse dye composition, the content of component A is 20 to 99 parts by weight, the content of component B is 1 to 80 parts by weight, the content of component C is 0 to 90 parts by weight, and the content of component D is 0 to 20 parts by weight.
7. The method for preparing a disperse dye composition according to claim 6, wherein the disperse dye composition comprises 40 to 95 parts by weight of component A, 5 to 60 parts by weight of component B, 0 to 90 parts by weight of component C, and 0 to 20 parts by weight of component D.
8. The process for producing a disperse dye composition according to claim 5, wherein the disperse dye composition comprises one or two of the compounds of formulae (1-1) to (1-2), one or more of the compounds of formula (2-1) and optionally one or more of the compounds of formulae (3-1) to (3-4).
9. The method for preparing a disperse dye composition according to claim 5, wherein the disperse dye composition comprises a compound of formula (1-1) and a compound of formula (2-9).
10. The method for preparing a disperse dye composition according to claim 5, wherein the disperse dye composition comprises: 10 to 40 parts by weight of component A consisting of one or more compounds of the formula (1), 3 to 50 parts by weight of component B consisting of one or more compounds of the formula (2) and 10 to 87 parts by weight of component C consisting of one or more compounds of the formula (3).
11. The method for preparing the disperse dye composition according to any one of claims 1 to 4, wherein the auxiliary material comprises an auxiliary agent and water, and the auxiliary agent is selected from one or more of a dispersing agent, a dyeing assistant, a surfactant and a bactericide.
12. The method for preparing a disperse dye composition according to claim 11, wherein the dispersant is one or more selected from the group consisting of a naphthalene sulfonic acid formaldehyde condensate, a methyl naphthalene sulfonic acid formaldehyde condensate, a benzyl naphthalene sulfonic acid formaldehyde condensate, and a lignosulfonate.
13. The method of preparing a disperse dye composition according to claim 11, wherein the dyeing assistant is anhydrous sodium sulphate.
14. A process for preparing a disperse dye composition according to any one of claims 1 to 4, wherein the base is selected from one or more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, aqueous ammonia, sodium hydroxide, potassium hydroxide, methylamine, ethylamine and triethylamine.
15. The process for preparing a disperse dye composition according to any one of claims 1 to 4, wherein one or more of the products I and one or more selected from the products II, optionally one or more selected from the products III and optionally one or more selected from the products IV are subjected to granulation treatment in the presence of an auxiliary material to prepare a disperse dye composition, and the liquid or the dry treatment is carried out;
or one or more of the products I and one or more selected from the products II, one or more selected from the products III, and one or more selected from the products IV are respectively granulated in the presence of auxiliary materials, and then are mixed to prepare liquid or dried to prepare the disperse dye composition.
16. The method for preparing a disperse dye composition according to claim 15, wherein the granulation treatment is performed using a sand mill or a grinder.
17. The method for preparing a disperse dye composition according to claim 15, wherein the drying is spray drying.
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