JPS58104953A - 水不溶性モノアゾ化合物及び疎水性繊維の染色方法 - Google Patents

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Publication number

JPS58104953A

JPS58104953A JP20400081A JP20400081A JPS58104953A JP S58104953 A JPS58104953 A JP S58104953A JP 20400081 A JP20400081 A JP 20400081A JP 20400081 A JP20400081 A JP 20400081A JP S58104953 A JPS58104953 A JP S58104953A

Authority

JP

Japan

Prior art keywords

dyeing

formula

water

parts

group

Prior art date

1981-12-16

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

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• 238000004043 dyeing Methods 0.000 title claims abstract description 28
• -1 monoazo compound Chemical class 0.000 title claims abstract description 25
• 239000000835 fiber Substances 0.000 title claims abstract description 20
• 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 10
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
• 238000000034 method Methods 0.000 claims abstract description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 239000000203 mixture Substances 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 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 claims description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
• 238000005859 coupling reaction Methods 0.000 abstract description 12
• 230000008878 coupling Effects 0.000 abstract description 9
• 238000010168 coupling process Methods 0.000 abstract description 9
• 229920000728 polyester Polymers 0.000 abstract description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 6
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 6
• 150000001875 compounds Chemical class 0.000 abstract description 5
• 239000002253 acid Substances 0.000 abstract description 4
• 229910000029 sodium carbonate Inorganic materials 0.000 abstract description 3
• 238000000859 sublimation Methods 0.000 abstract description 3
• 230000008022 sublimation Effects 0.000 abstract description 3
• 238000005406 washing Methods 0.000 abstract description 3
• 238000000354 decomposition reaction Methods 0.000 abstract description 2
• 239000000463 material Substances 0.000 abstract description 2
• 230000035945 sensitivity Effects 0.000 abstract description 2
• LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 abstract 1
• 230000002152 alkylating effect Effects 0.000 abstract 1
• 229910052736 halogen Inorganic materials 0.000 abstract 1
• 150000002367 halogens Chemical class 0.000 abstract 1
• PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 abstract 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
• 239000000975 dye Substances 0.000 description 32
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 239000004744 fabric Substances 0.000 description 3
• 229920005610 lignin Polymers 0.000 description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• 239000012736 aqueous medium Substances 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
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 239000003795 chemical substances by application Substances 0.000 description 2
• 238000004140 cleaning Methods 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 239000006185 dispersion Substances 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
• KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
• RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 2
• 229910052500 inorganic mineral Inorganic materials 0.000 description 2
• 239000011707 mineral Substances 0.000 description 2
• 235000010755 mineral Nutrition 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 235000011121 sodium hydroxide Nutrition 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
• BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 241000974482 Aricia saepiolus Species 0.000 description 1
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
• CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
• 241000861914 Plecoglossus altivelis Species 0.000 description 1
• 239000004952 Polyamide Substances 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 241000269821 Scombridae Species 0.000 description 1
• IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 1
• XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
• 239000012190 activator Substances 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 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
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 125000004432 carbon atom Chemical group C* 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 230000000052 comparative effect Effects 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000004134 energy conservation Methods 0.000 description 1
• 239000010419 fine particle Substances 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 235000020640 mackerel Nutrition 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• IRFCTHNJIWUUJZ-UHFFFAOYSA-N n-(3-aminophenyl)benzamide Chemical compound NC1=CC=CC(NC(=O)C=2C=CC=CC=2)=C1 IRFCTHNJIWUUJZ-UHFFFAOYSA-N 0.000 description 1
• DRXFARCOYOPZDW-UHFFFAOYSA-N n-(3-aminophenyl)butanamide Chemical compound CCCC(=O)NC1=CC=CC(N)=C1 DRXFARCOYOPZDW-UHFFFAOYSA-N 0.000 description 1
• DRXLHYPPJRAJSL-UHFFFAOYSA-N n-(3-aminophenyl)formamide Chemical compound NC1=CC=CC(NC=O)=C1 DRXLHYPPJRAJSL-UHFFFAOYSA-N 0.000 description 1
• VGDKCRMZIWPMPW-UHFFFAOYSA-N n-(3-aminophenyl)propanamide Chemical compound CCC(=O)NC1=CC=CC(N)=C1 VGDKCRMZIWPMPW-UHFFFAOYSA-N 0.000 description 1
• VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
• 235000010292 orthophenyl phenol Nutrition 0.000 description 1
• 239000002798 polar solvent Substances 0.000 description 1
• 229920002647 polyamide Polymers 0.000 description 1
• 229920000098 polyolefin Polymers 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 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 1
• 150000003839 salts Chemical class 0.000 description 1
• 238000004513 sizing Methods 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 238000001694 spray drying Methods 0.000 description 1
• 239000004575 stone Substances 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 239000004753 textile Substances 0.000 description 1