JPS58215455A - モノアゾ化合物及びそれを用いる染色法 - Google Patents

Info

Publication number

JPS58215455A

JPS58215455A JP9798982A JP9798982A JPS58215455A JP S58215455 A JPS58215455 A JP S58215455A JP 9798982 A JP9798982 A JP 9798982A JP 9798982 A JP9798982 A JP 9798982A JP S58215455 A JPS58215455 A JP S58215455A

Authority

JP

Japan

Prior art keywords

group

parts

monoazo compound

acid

formula

Prior art date

1982-06-07

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Granted

Links

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• -1 Monoazo compound Chemical class 0.000 title claims abstract description 31
• 238000004043 dyeing Methods 0.000 title claims description 16
• 238000000034 method Methods 0.000 title claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
• 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 4
• 125000003545 alkoxy group Chemical group 0.000 claims abstract 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 239000012209 synthetic fiber Substances 0.000 claims description 6
• 229920002994 synthetic fiber Polymers 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims 3
• 239000000975 dye Substances 0.000 abstract description 14
• 239000000835 fiber Substances 0.000 abstract description 11
• 229920000728 polyester Polymers 0.000 abstract description 6
• 150000001412 amines Chemical class 0.000 abstract description 5
• NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 abstract description 5
• 239000000203 mixture Substances 0.000 abstract description 5
• 239000004952 Polyamide Substances 0.000 abstract description 4
• 239000002253 acid Substances 0.000 abstract description 4
• 229920002647 polyamide Polymers 0.000 abstract description 4
• 230000008878 coupling Effects 0.000 abstract description 3
• 238000010168 coupling process Methods 0.000 abstract description 3
• 238000005859 coupling reaction Methods 0.000 abstract description 3
• 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 3
• 239000011707 mineral Substances 0.000 abstract description 3
• 239000012954 diazonium Substances 0.000 abstract description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 abstract description 2
• 229910052736 halogen Inorganic materials 0.000 abstract description 2
• 150000002367 halogens Chemical class 0.000 abstract description 2
• 239000000463 material Substances 0.000 abstract description 2
• RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 abstract 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• 239000004744 fabric Substances 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
• 238000005406 washing Methods 0.000 description 6
• 238000007639 printing Methods 0.000 description 5
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
• 238000010018 discharge printing Methods 0.000 description 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• 235000019260 propionic acid Nutrition 0.000 description 3
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
• 238000010025 steaming Methods 0.000 description 3
• TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
• 229960001413 acetanilide Drugs 0.000 description 2
• 239000012736 aqueous medium Substances 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
• 239000003638 chemical reducing agent Substances 0.000 description 2
• 239000003795 chemical substances by application Substances 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• 150000001875 compounds Chemical class 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 238000000354 decomposition reaction Methods 0.000 description 2
• 239000006185 dispersion Substances 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 235000010755 mineral Nutrition 0.000 description 2
• 239000012046 mixed solvent Substances 0.000 description 2
• PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 238000004513 sizing Methods 0.000 description 2
• 239000001119 stannous chloride Substances 0.000 description 2
• 235000011150 stannous chloride Nutrition 0.000 description 2
• 238000000859 sublimation Methods 0.000 description 2
• 230000008022 sublimation Effects 0.000 description 2
• RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
• MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 1
• UIHYHADQHHUIOF-UHFFFAOYSA-N 2-[n-ethyl-3-methyl-4-[(5-nitro-1,3-thiazol-2-yl)diazenyl]anilino]ethanol Chemical compound CC1=CC(N(CCO)CC)=CC=C1N=NC1=NC=C([N+]([O-])=O)S1 UIHYHADQHHUIOF-UHFFFAOYSA-N 0.000 description 1
• 229940018167 2-amino-5-nitrothiazole Drugs 0.000 description 1
• BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
• DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
• KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
• MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
• RDXLYGJSWZYTFJ-UHFFFAOYSA-N Niridazole Chemical compound S1C([N+](=O)[O-])=CN=C1N1C(=O)NCC1 RDXLYGJSWZYTFJ-UHFFFAOYSA-N 0.000 description 1
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
• CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
• XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
• 239000002280 amphoteric surfactant Substances 0.000 description 1
• 229960003237 betaine Drugs 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 238000004140 cleaning Methods 0.000 description 1
• 229940125782 compound 2 Drugs 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
• 150000001989 diazonium salts Chemical class 0.000 description 1
• 238000006193 diazotization reaction Methods 0.000 description 1
• 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 1
• 229940117964 disperse blue 106 Drugs 0.000 description 1
• 239000000986 disperse dye Substances 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 239000010419 fine particle Substances 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 230000002209 hydrophobic effect Effects 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 229960005130 niridazole Drugs 0.000 description 1
• VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 235000010292 orthophenyl phenol Nutrition 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 229920000098 polyolefin Polymers 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 235000011121 sodium hydroxide Nutrition 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 238000001694 spray drying Methods 0.000 description 1
• 238000010186 staining Methods 0.000 description 1
• IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
• 229950011008 tetrachloroethylene Drugs 0.000 description 1
• 239000004753 textile Substances 0.000 description 1
• FSBZGYYPMXSIEE-UHFFFAOYSA-H tin(2+);diphosphate Chemical compound [Sn+2].[Sn+2].[Sn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O FSBZGYYPMXSIEE-UHFFFAOYSA-H 0.000 description 1
• 150000004992 toluidines Chemical class 0.000 description 1