CS199564B2 - Linear polyesters spun-dyeing method - Google Patents
Linear polyesters spun-dyeing method Download PDFInfo
- Publication number
- CS199564B2 CS199564B2 CS745334A CS533474A CS199564B2 CS 199564 B2 CS199564 B2 CS 199564B2 CS 745334 A CS745334 A CS 745334A CS 533474 A CS533474 A CS 533474A CS 199564 B2 CS199564 B2 CS 199564B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- anthraquinone
- amino
- hydrogen
- phenyl
- ether
- Prior art date
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000004043 dyeing Methods 0.000 title claims abstract description 8
- -1 arylmercapto Chemical group 0.000 claims abstract description 33
- 239000000975 dye Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 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 claims description 21
- 150000004056 anthraquinones Chemical class 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract description 16
- IEFRFBKOSLZJIK-UHFFFAOYSA-N 1-anilino-2-phenoxyanthracene-9,10-dione Chemical compound C=1C=CC=CC=1OC1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 IEFRFBKOSLZJIK-UHFFFAOYSA-N 0.000 abstract description 3
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000005239 aroylamino group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 6
- JDUYPUMQALQRCN-UHFFFAOYSA-N 4-bromophenyl phenyl ether Chemical compound C1=CC(Br)=CC=C1OC1=CC=CC=C1 JDUYPUMQALQRCN-UHFFFAOYSA-N 0.000 description 5
- 238000002074 melt spinning Methods 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UFGDCUJPYDDXRM-UHFFFAOYSA-N 1,5-bis(2-benzoylanilino)anthracene-9,10-dione Chemical compound C=1C=CC=C(NC=2C=3C(=O)C4=CC=CC(NC=5C(=CC=CC=5)C(=O)C=5C=CC=CC=5)=C4C(=O)C=3C=CC=2)C=1C(=O)C1=CC=CC=C1 UFGDCUJPYDDXRM-UHFFFAOYSA-N 0.000 description 2
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-UHFFFAOYSA-N 0.000 description 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 2
- SSTNIXFHCIOCJI-UHFFFAOYSA-N 1-methyl-4-phenoxybenzene Chemical compound C1=CC(C)=CC=C1OC1=CC=CC=C1 SSTNIXFHCIOCJI-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VMHYWKBKHMYRNF-UHFFFAOYSA-N (2-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1 VMHYWKBKHMYRNF-UHFFFAOYSA-N 0.000 description 1
- CPLWKNRPZVNELG-UHFFFAOYSA-N (3-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 CPLWKNRPZVNELG-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- CWWLJTQYTKOLRU-UHFFFAOYSA-N 1,2-bis(4-phenoxyanilino)anthracene-9,10-dione Chemical class C=1C=C(OC=2C=CC=CC=2)C=CC=1NC1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 CWWLJTQYTKOLRU-UHFFFAOYSA-N 0.000 description 1
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- QFYZUUMEXXFCKY-UHFFFAOYSA-N 1,5-bis(4-phenoxyanilino)anthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC(NC=4C=CC(OC=5C=CC=CC=5)=CC=4)=C3C(=O)C2=CC=CC=1NC(C=C1)=CC=C1OC1=CC=CC=C1 QFYZUUMEXXFCKY-UHFFFAOYSA-N 0.000 description 1
- JUXFTSMEZSMUDG-UHFFFAOYSA-N 1,5-bis[2-(4-methylbenzoyl)anilino]anthracene-9,10-dione Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC(NC=3C(=CC=CC=3)C(=O)C=3C=CC(C)=CC=3)=C1C2=O JUXFTSMEZSMUDG-UHFFFAOYSA-N 0.000 description 1
- AXABXWMNLWJHPD-UHFFFAOYSA-N 1,5-diamino-2-chloroanthracene-9,10-dione Chemical compound O=C1C2=C(N)C(Cl)=CC=C2C(=O)C2=C1C=CC=C2N AXABXWMNLWJHPD-UHFFFAOYSA-N 0.000 description 1
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 1
- VBQNYYXVDQUKIU-UHFFFAOYSA-N 1,8-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C=CC=C2Cl VBQNYYXVDQUKIU-UHFFFAOYSA-N 0.000 description 1
- MMFCPKYGMSQKCQ-UHFFFAOYSA-N 1-amino-4-(4-methoxyanilino)anthracene-9,10-dione Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O MMFCPKYGMSQKCQ-UHFFFAOYSA-N 0.000 description 1
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 1
- PHTDHFYUHFJDJW-UHFFFAOYSA-N 1-amino-4-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2C PHTDHFYUHFJDJW-UHFFFAOYSA-N 0.000 description 1
- HKPYKLPVGPMRDS-UHFFFAOYSA-N 1-amino-5-(4-methylanilino)anthracene-9,10-dione Chemical compound NC1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)NC1=CC=C(C=C1)C)=O HKPYKLPVGPMRDS-UHFFFAOYSA-N 0.000 description 1
- ANPVRWWKXVYROQ-UHFFFAOYSA-N 1-hydroxy-4-(4-phenoxyanilino)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(O)=CC=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 ANPVRWWKXVYROQ-UHFFFAOYSA-N 0.000 description 1
- DBKWISXILXVKEW-UHFFFAOYSA-N 1-methyl-3-(4-methylphenoxy)benzene Chemical compound C1=CC(C)=CC=C1OC1=CC=CC(C)=C1 DBKWISXILXVKEW-UHFFFAOYSA-N 0.000 description 1
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 1
- YHCIQYSVFONICB-UHFFFAOYSA-N 1-sulfanylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S YHCIQYSVFONICB-UHFFFAOYSA-N 0.000 description 1
- REZBJCUQELMZBL-UHFFFAOYSA-N 1-tert-butyl-4-phenoxybenzene Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1=CC=CC=C1 REZBJCUQELMZBL-UHFFFAOYSA-N 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IHCJVCSNHVZNEP-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=C(C(=O)C2=C(NC3=CC=CC=4C(C5=C(C=CC=C5C(C3=4)=O)NC3=C(C=CC=C3)C(C3=CC=C(C=C3)C3=CC=CC=C3)=O)=O)C=CC=C2)C=C1 Chemical compound C1(=CC=CC=C1)C1=CC=C(C(=O)C2=C(NC3=CC=CC=4C(C5=C(C=CC=C5C(C3=4)=O)NC3=C(C=CC=C3)C(C3=CC=C(C=C3)C3=CC=CC=C3)=O)=O)C=CC=C2)C=C1 IHCJVCSNHVZNEP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- VZPDAENHOKEFLP-UHFFFAOYSA-N NC1=C2C(C=3C=CC=C(C3C(C2=CC=C1)=O)NC1=CC=C(C=C1)Cl)=O Chemical compound NC1=C2C(C=3C=CC=C(C3C(C2=CC=C1)=O)NC1=CC=C(C=C1)Cl)=O VZPDAENHOKEFLP-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- FBNCDTLHQPLASV-UHFFFAOYSA-L disodium;5-methyl-2-[[5-(4-methyl-2-sulfonatoanilino)-9,10-dioxoanthracen-1-yl]amino]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC(NC=3C(=CC(C)=CC=3)S([O-])(=O)=O)=C1C2=O FBNCDTLHQPLASV-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 239000011888 foil Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GYLVUQLRAUNUFD-UHFFFAOYSA-N n-(4-amino-9,10-dioxoanthracen-1-yl)-2-chlorobenzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC(=O)C1=CC=CC=C1Cl GYLVUQLRAUNUFD-UHFFFAOYSA-N 0.000 description 1
- ZWFYJWUYSYLFPH-UHFFFAOYSA-N n-(4-amino-9,10-dioxoanthracen-1-yl)-3-chlorobenzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC(=O)C1=CC=CC(Cl)=C1 ZWFYJWUYSYLFPH-UHFFFAOYSA-N 0.000 description 1
- QMTDZZMSWVNEBX-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)-2-chlorobenzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1Cl QMTDZZMSWVNEBX-UHFFFAOYSA-N 0.000 description 1
- JFAUXACZVJJMNY-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)-3-chlorobenzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC(Cl)=C1 JFAUXACZVJJMNY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004091 panning Methods 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000006209 tert-butylation Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1122473A CH575444A5 (en, 2012) | 1973-08-02 | 1973-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199564B2 true CS199564B2 (en) | 1980-07-31 |
Family
ID=4371321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS745334A CS199564B2 (en) | 1973-08-02 | 1974-07-25 | Linear polyesters spun-dyeing method |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3939113A (en, 2012) |
| JP (1) | JPS5741506B2 (en, 2012) |
| AR (1) | AR212856A1 (en, 2012) |
| BE (1) | BE818377A (en, 2012) |
| CA (1) | CA1045272A (en, 2012) |
| CH (1) | CH575444A5 (en, 2012) |
| CS (1) | CS199564B2 (en, 2012) |
| DE (1) | DE2436652C2 (en, 2012) |
| ES (1) | ES428842A1 (en, 2012) |
| FR (1) | FR2245811B1 (en, 2012) |
| GB (1) | GB1457933A (en, 2012) |
| NL (1) | NL7409401A (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2421375A1 (de) * | 1974-05-03 | 1975-12-04 | Bayer Ag | Verfahren zum massefaerben von polyestern |
| CH603746A5 (en, 2012) * | 1974-09-27 | 1978-08-31 | Ciba Geigy Ag | |
| CH599987A5 (en, 2012) * | 1975-10-28 | 1978-06-15 | Sandoz Ag | |
| WO2004083270A2 (en) * | 2003-03-18 | 2004-09-30 | Ciba Specialty Chemicals Holding Inc. | Colored polymeric articles having high melt temperatures |
| TWI568719B (zh) * | 2012-10-20 | 2017-02-01 | 克萊瑞特國際股份有限公司 | 二聚合陰離子型蒽醌染料 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7002735A (en, 2012) * | 1969-02-27 | 1970-08-31 | ||
| US3840567A (en) * | 1972-10-20 | 1974-10-08 | American Aniline Prod | Polyester and plastic dyes |
-
1973
- 1973-08-02 CH CH1122473A patent/CH575444A5/xx not_active IP Right Cessation
-
1974
- 1974-07-11 NL NL7409401A patent/NL7409401A/xx not_active Application Discontinuation
- 1974-07-25 CS CS745334A patent/CS199564B2/cs unknown
- 1974-07-29 US US05/492,629 patent/US3939113A/en not_active Expired - Lifetime
- 1974-07-30 DE DE2436652A patent/DE2436652C2/de not_active Expired
- 1974-07-31 AR AR254978A patent/AR212856A1/es active
- 1974-07-31 CA CA206,016A patent/CA1045272A/en not_active Expired
- 1974-08-01 FR FR7426749A patent/FR2245811B1/fr not_active Expired
- 1974-08-01 ES ES428842A patent/ES428842A1/es not_active Expired
- 1974-08-01 GB GB3394374A patent/GB1457933A/en not_active Expired
- 1974-08-01 BE BE147190A patent/BE818377A/xx not_active IP Right Cessation
- 1974-08-02 JP JP49088946A patent/JPS5741506B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1045272A (en) | 1978-12-26 |
| DE2436652C2 (de) | 1982-07-22 |
| AU7186974A (en) | 1976-02-05 |
| CH575444A5 (en, 2012) | 1976-05-14 |
| NL7409401A (nl) | 1975-02-04 |
| FR2245811A1 (en, 2012) | 1975-04-25 |
| GB1457933A (en) | 1976-12-08 |
| FR2245811B1 (en, 2012) | 1977-01-07 |
| US3939113A (en) | 1976-02-17 |
| JPS5049360A (en, 2012) | 1975-05-02 |
| AR212856A1 (es) | 1978-10-31 |
| JPS5741506B2 (en, 2012) | 1982-09-03 |
| BE818377A (fr) | 1975-02-03 |
| ES428842A1 (es) | 1976-09-01 |
| DE2436652A1 (de) | 1975-02-20 |
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