KR102729749B1 - 염료조성물 - Google Patents
염료조성물 Download PDFInfo
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- KR102729749B1 KR102729749B1 KR1020227027239A KR20227027239A KR102729749B1 KR 102729749 B1 KR102729749 B1 KR 102729749B1 KR 1020227027239 A KR1020227027239 A KR 1020227027239A KR 20227027239 A KR20227027239 A KR 20227027239A KR 102729749 B1 KR102729749 B1 KR 102729749B1
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- South Korea
- Prior art keywords
- compound
- dye composition
- formula
- dye
- dyeing
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 586
- 150000001875 compounds Chemical class 0.000 claims abstract description 1149
- 238000004043 dyeing Methods 0.000 claims abstract description 339
- 238000000034 method Methods 0.000 claims abstract description 191
- 239000000835 fiber Substances 0.000 claims abstract description 164
- 239000002270 dispersing agent Substances 0.000 claims abstract description 134
- 239000000975 dye Substances 0.000 claims description 588
- 125000000217 alkyl group Chemical group 0.000 claims description 267
- 125000004432 carbon atom Chemical group C* 0.000 claims description 258
- -1 polyoxyethylene Polymers 0.000 claims description 192
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 187
- 230000008569 process Effects 0.000 claims description 90
- 125000005843 halogen group Chemical group 0.000 claims description 64
- 239000004743 Polypropylene Substances 0.000 claims description 51
- 229920001155 polypropylene Polymers 0.000 claims description 51
- 239000000843 powder Substances 0.000 claims description 49
- 229920001577 copolymer Polymers 0.000 claims description 47
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 125000006353 oxyethylene group Chemical group 0.000 claims description 31
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 28
- 239000004698 Polyethylene Substances 0.000 claims description 27
- 229920000573 polyethylene Polymers 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 238000007654 immersion Methods 0.000 claims description 16
- 229920000098 polyolefin Polymers 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000005418 aryl aryl group Chemical group 0.000 claims description 5
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 4
- 238000010014 continuous dyeing Methods 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- 238000005245 sintering Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 abstract description 30
- 238000000859 sublimation Methods 0.000 abstract description 24
- 230000008022 sublimation Effects 0.000 abstract description 24
- 239000003086 colorant Substances 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 description 383
- 238000003786 synthesis reaction Methods 0.000 description 383
- 239000011324 bead Substances 0.000 description 212
- 239000002002 slurry Substances 0.000 description 212
- 239000000243 solution Substances 0.000 description 191
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 189
- 238000004519 manufacturing process Methods 0.000 description 188
- 239000006185 dispersion Substances 0.000 description 186
- 239000001045 blue dye Substances 0.000 description 151
- 239000010419 fine particle Substances 0.000 description 127
- 239000011521 glass Substances 0.000 description 105
- 238000002360 preparation method Methods 0.000 description 97
- 239000002245 particle Substances 0.000 description 92
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 82
- 239000001048 orange dye Substances 0.000 description 71
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 69
- 238000005859 coupling reaction Methods 0.000 description 67
- 239000001044 red dye Substances 0.000 description 66
- 239000001047 purple dye Substances 0.000 description 56
- 238000012360 testing method Methods 0.000 description 53
- 239000011541 reaction mixture Substances 0.000 description 52
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- 239000000047 product Substances 0.000 description 37
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 34
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 30
- 238000011156 evaluation Methods 0.000 description 28
- 239000004744 fabric Substances 0.000 description 25
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 25
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000986 disperse dye Substances 0.000 description 21
- 229920000728 polyester Polymers 0.000 description 19
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
- 150000008049 diazo compounds Chemical class 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 239000001043 yellow dye Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 16
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 16
- 229920005672 polyolefin resin Polymers 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 14
- FRLFZLYEKQHZEJ-UHFFFAOYSA-N N-(3-amino-4-methoxyphenyl)octanamide Chemical compound CCCCCCCC(=O)NC1=CC=C(OC)C(N)=C1 FRLFZLYEKQHZEJ-UHFFFAOYSA-N 0.000 description 14
- 239000002994 raw material Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000006193 diazotization reaction Methods 0.000 description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 12
- 229910052500 inorganic mineral Inorganic materials 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000011707 mineral Substances 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 230000002378 acidificating effect Effects 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000007731 hot pressing Methods 0.000 description 9
- WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 244000073231 Larrea tridentata Species 0.000 description 8
- 235000006173 Larrea tridentata Nutrition 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 229960002126 creosote Drugs 0.000 description 8
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- GCNLRNBDDUYJMP-UHFFFAOYSA-M sodium;2-methylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C)=CC=C21 GCNLRNBDDUYJMP-UHFFFAOYSA-M 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 8
- 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 description 7
- 150000004056 anthraquinones Chemical class 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- WNLMUPLRUVFLAD-UHFFFAOYSA-N n-(3-aminophenyl)octanamide Chemical compound CCCCCCCC(=O)NC1=CC=CC(N)=C1 WNLMUPLRUVFLAD-UHFFFAOYSA-N 0.000 description 7
- 229920013716 polyethylene resin Polymers 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 6
- 235000019260 propionic acid Nutrition 0.000 description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000010998 test method Methods 0.000 description 6
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 5
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 5
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000001000 anthraquinone dye Substances 0.000 description 5
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 description 5
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 5
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 5
- 238000011109 contamination Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000010025 steaming Methods 0.000 description 5
- 239000002759 woven fabric Substances 0.000 description 5
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 4
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 4
- TYMLOMAKGOJONV-IDEBNGHGSA-N 4-nitroaniline Chemical class N[13C]1=[13CH][13CH]=[13C]([N+]([O-])=O)[13CH]=[13CH]1 TYMLOMAKGOJONV-IDEBNGHGSA-N 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000004737 colorimetric analysis Methods 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 4
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 235000002906 tartaric acid Nutrition 0.000 description 4
- 239000011975 tartaric acid Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 3
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 3
- 125000005916 2-methylpentyl group Chemical group 0.000 description 3
- 125000005917 3-methylpentyl group Chemical group 0.000 description 3
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 3
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 3
- VCLZHGSHIJOXRB-UHFFFAOYSA-N 5-amino-6h-anthra[9,1-cd][1,2]thiazol-6-one Chemical compound S1N=C2C3=CC=CC=C3C(=O)C3=C2C1=CC=C3N VCLZHGSHIJOXRB-UHFFFAOYSA-N 0.000 description 3
- SQBCSDZTDXLTLE-UHFFFAOYSA-N 5-nitro-2,1-benzothiazol-3-amine Chemical compound C1=CC([N+]([O-])=O)=CC2=C(N)SN=C21 SQBCSDZTDXLTLE-UHFFFAOYSA-N 0.000 description 3
- UQPHGZMYCJTPJF-UHFFFAOYSA-N CCCCCCCC(NC(C=C1)=CC(NCCC#N)=C1OC)=O Chemical compound CCCCCCCC(NC(C=C1)=CC(NCCC#N)=C1OC)=O UQPHGZMYCJTPJF-UHFFFAOYSA-N 0.000 description 3
- SXGWGJZIYDSBMS-UHFFFAOYSA-N CCCCCCCC(NC(C=C1)=CC([N+]([O-])=O)=C1OC)=O Chemical compound CCCCCCCC(NC(C=C1)=CC([N+]([O-])=O)=C1OC)=O SXGWGJZIYDSBMS-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 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 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920005673 polypropylene based resin Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000004513 sizing Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 210000004243 sweat Anatomy 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 2
- FENJKTQEFUPECW-UHFFFAOYSA-N 3-anilinopropanenitrile Chemical compound N#CCCNC1=CC=CC=C1 FENJKTQEFUPECW-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- LDKVDGSKPOUPMP-UHFFFAOYSA-N CCCCCCN(CCCCCC)C1=CC(NC(C)=O)=CC=C1OC Chemical compound CCCCCCN(CCCCCC)C1=CC(NC(C)=O)=CC=C1OC LDKVDGSKPOUPMP-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
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- DGYRVXQIGUEFFK-UHFFFAOYSA-N n,n-dihexylaniline Chemical compound CCCCCCN(CCCCCC)C1=CC=CC=C1 DGYRVXQIGUEFFK-UHFFFAOYSA-N 0.000 description 1
- PTRSTXBRQVXIEW-UHFFFAOYSA-N n,n-dioctylaniline Chemical compound CCCCCCCCN(CCCCCCCC)C1=CC=CC=C1 PTRSTXBRQVXIEW-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- VYAVWILUXQDDKH-UHFFFAOYSA-N n-[3-(dibutylamino)phenyl]acetamide Chemical compound CCCCN(CCCC)C1=CC=CC(NC(C)=O)=C1 VYAVWILUXQDDKH-UHFFFAOYSA-N 0.000 description 1
- PTEGHLXVDHZDTI-UHFFFAOYSA-N n-[3-(didodecylamino)phenyl]acetamide Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)C1=CC=CC(NC(C)=O)=C1 PTEGHLXVDHZDTI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PWGFKMXYANFRIJ-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]octanamide Chemical compound CCCCCCCC(=O)NC1=CC=CC(N(CC)CC)=C1 PWGFKMXYANFRIJ-UHFFFAOYSA-N 0.000 description 1
- OQSBXCCSTGNIBR-UHFFFAOYSA-N n-[3-(dihexylamino)phenyl]acetamide Chemical compound CCCCCCN(CCCCCC)C1=CC=CC(NC(C)=O)=C1 OQSBXCCSTGNIBR-UHFFFAOYSA-N 0.000 description 1
- OFGYHXLLMLVGLS-UHFFFAOYSA-N n-[3-(dihexylamino)phenyl]propanamide Chemical compound CCCCCCN(CCCCCC)C1=CC=CC(NC(=O)CC)=C1 OFGYHXLLMLVGLS-UHFFFAOYSA-N 0.000 description 1
- WYADURQGXGOLSP-UHFFFAOYSA-N n-[3-(dioctylamino)phenyl]acetamide Chemical compound CCCCCCCCN(CCCCCCCC)C1=CC=CC(NC(C)=O)=C1 WYADURQGXGOLSP-UHFFFAOYSA-N 0.000 description 1
- TWQCMKMTNOZJHD-UHFFFAOYSA-N n-[3-[bis(2-ethylhexyl)amino]phenyl]propanamide Chemical compound CCCCC(CC)CN(CC(CC)CCCC)C1=CC=CC(NC(=O)CC)=C1 TWQCMKMTNOZJHD-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229920001384 propylene homopolymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 230000021148 sequestering of metal ion Effects 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0081—Isothiazoles or condensed isothiazoles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0822—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by NO2
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3608—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered heterocyclic ring with only one nitrogen as heteroatom
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
-
- 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
- C09B67/006—Preparation of 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
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/0089—Non common dispersing agents non ionic dispersing agent, e.g. EO or PO addition products
-
- 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
-
- 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
- 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
- D06P3/79—Polyolefins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JPJP-P-2020-046823 | 2020-03-17 | ||
| JP2020046823 | 2020-03-17 | ||
| PCT/JP2021/010481 WO2021187447A1 (ja) | 2020-03-17 | 2021-03-16 | 染料組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20220123299A KR20220123299A (ko) | 2022-09-06 |
| KR102729749B1 true KR102729749B1 (ko) | 2024-11-13 |
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| KR1020227027239A Active KR102729749B1 (ko) | 2020-03-17 | 2021-03-16 | 염료조성물 |
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| JP (1) | JP7222565B2 (enrdf_load_stackoverflow) |
| KR (1) | KR102729749B1 (enrdf_load_stackoverflow) |
| CN (1) | CN115279839B (enrdf_load_stackoverflow) |
| TW (2) | TWI863879B (enrdf_load_stackoverflow) |
| WO (1) | WO2021187447A1 (enrdf_load_stackoverflow) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4200739A1 (de) * | 1991-01-17 | 1992-07-23 | Ciba Geigy Ag | Benzoisothiazolylazofarbstoffe und ihre verwendung im thermotransferdruck |
| JP2019203223A (ja) * | 2018-05-24 | 2019-11-28 | 日本化薬株式会社 | ポリプロピレン繊維の染色方法及び着色ポリプロピレン繊維 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB953719A (en) * | 1961-07-07 | 1964-04-02 | Ici Ltd | Dyeing of polyolefine materials |
| US3536735A (en) | 1967-06-27 | 1970-10-27 | Du Pont | Oleophilic anthraquinone red dyes for polypropylene |
| BE759527A (fr) * | 1969-11-28 | 1971-04-30 | Bayer Ag | Procede de teinture en continu de matieres fibreuses synthetiques |
| DE2254376A1 (de) * | 1972-11-07 | 1974-05-22 | Hoechst Ag | Verfahren zum faerben von synthetischen fasermaterialien aus organischen loesemitteln |
| JPS55152869A (en) | 1979-05-16 | 1980-11-28 | Sumitomo Chemical Co | Dyeing of polyester fiber |
| JPS6026869B2 (ja) * | 1979-07-20 | 1985-06-26 | 住友化学工業株式会社 | 疎水性繊維の染色あるいは捺染方法 |
| JPS5658077A (en) * | 1979-10-17 | 1981-05-20 | Sanyo Chemical Ind Ltd | Disperse dyestuff composition |
| JPS582355A (ja) * | 1981-06-29 | 1983-01-07 | Sumitomo Chem Co Ltd | 分散染料組成物およびそれを用いる染色法 |
| DE3131849A1 (de) * | 1981-08-12 | 1983-02-24 | Hoechst Ag, 6000 Frankfurt | Transferdrucktraeger, verfahren zu seiner herstellung und seine anwendung |
| DE3234186A1 (de) * | 1982-09-15 | 1984-03-15 | Cassella Ag, 6000 Frankfurt | Mischungen von monoazofarbstoffen |
| GB2134130A (en) * | 1983-01-21 | 1984-08-08 | Yorkshire Chemicals Ltd | Disperse azo dyes |
| CH661519A5 (de) * | 1984-10-18 | 1987-07-31 | Ciba Geigy Ag | Monoazoverbindungen. |
| JPS61152647A (ja) * | 1984-12-27 | 1986-07-11 | Toshiba Corp | ジアゾ化合物 |
| DE3609342A1 (de) * | 1986-03-20 | 1987-09-24 | Bayer Ag | Verfahren zur herstellung von azoverbindungen |
| JPS631277A (ja) | 1986-06-20 | 1988-01-06 | Matsushita Electric Ind Co Ltd | カラ−固体撮像装置 |
| JPH068387B2 (ja) * | 1986-11-26 | 1994-02-02 | 日本化薬株式会社 | モノアゾ化合物及びそれを用いる疎水性繊維の染色法 |
| JP2872388B2 (ja) * | 1990-11-07 | 1999-03-17 | 日本化薬株式会社 | 分散染料組成物及び疎水性繊維の染色法 |
| US5283238A (en) | 1992-04-24 | 1994-02-01 | Immtech International, Inc. | Methods of treating cancer using modified C-reactive protein |
| JP2767564B2 (ja) * | 1994-04-19 | 1998-06-18 | 日本化薬株式会社 | 染料組成物およびそれを用いる疎水性繊維材料の染色法 |
| JPH0872882A (ja) | 1994-09-05 | 1996-03-19 | Nippon Dennetsu Co Ltd | 包装容器 |
| JP3806166B2 (ja) * | 1995-10-18 | 2006-08-09 | ダイスタージャパン株式会社 | 青色系分散染料混合物及びその製造方法 |
| JPH103515A (ja) | 1996-06-17 | 1998-01-06 | Canon Inc | 画像処理方法及び装置 |
| JPH11158403A (ja) * | 1997-11-28 | 1999-06-15 | Sumitomo Chem Co Ltd | 分散染料組成物およびそれを用いる疎水性材料の着色方法 |
| KR101172860B1 (ko) * | 2010-03-09 | 2012-08-09 | 경북대학교 산학협력단 | 초고분자량 폴리에틸렌 섬유의 염색방법 |
| KR101618699B1 (ko) * | 2015-03-31 | 2016-05-18 | 주식회사 오영 | 폴리올레핀 섬유용 염료 조성물 |
| KR101713675B1 (ko) * | 2015-04-02 | 2017-03-09 | 대영산업 주식회사 | 내알칼리성 흑색 분산염료 조성물 |
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2021
- 2021-03-16 TW TW113124583A patent/TWI863879B/zh active
- 2021-03-16 TW TW110109387A patent/TWI856244B/zh active
- 2021-03-16 CN CN202180020355.5A patent/CN115279839B/zh active Active
- 2021-03-16 WO PCT/JP2021/010481 patent/WO2021187447A1/ja active IP Right Grant
- 2021-03-16 JP JP2021536697A patent/JP7222565B2/ja active Active
- 2021-03-16 KR KR1020227027239A patent/KR102729749B1/ko active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4200739A1 (de) * | 1991-01-17 | 1992-07-23 | Ciba Geigy Ag | Benzoisothiazolylazofarbstoffe und ihre verwendung im thermotransferdruck |
| JP2019203223A (ja) * | 2018-05-24 | 2019-11-28 | 日本化薬株式会社 | ポリプロピレン繊維の染色方法及び着色ポリプロピレン繊維 |
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| CN115279839A (zh) | 2022-11-01 |
| JP7222565B2 (ja) | 2023-02-15 |
| TW202140681A (zh) | 2021-11-01 |
| TW202440803A (zh) | 2024-10-16 |
| JPWO2021187447A1 (enrdf_load_stackoverflow) | 2021-09-23 |
| TW202440804A (zh) | 2024-10-16 |
| KR20220123299A (ko) | 2022-09-06 |
| TWI856244B (zh) | 2024-09-21 |
| TWI863879B (zh) | 2024-11-21 |
| CN115279839B (zh) | 2025-06-27 |
| WO2021187447A1 (ja) | 2021-09-23 |
| TW202440532A (zh) | 2024-10-16 |
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