JPS58104954A

JPS58104954A - 水不溶性モノアゾ化合物及び疎水性繊維の染色方法

水不溶性モノアゾ化合物及び疎水性繊維の染色方法

Info

Publication number: JPS58104954A
Authority: JP; Japan
Prior art keywords: group; dyeing; water; formula; dye
Prior art date: 1981-12-16
Legal status : Granted

Application number

JP20400181A

Other languages

English (en)

Japanese (ja)

Other versions

JPH032909B2 (enrdf_load_stackoverflow

Inventor

Kiyoyasu Hashimoto

橋本　清保

Akira Murata

村田　明

Hideo Hattori

秀雄服部

Akira Takeshita

明竹下

Current Assignee

GOSEI SENRIYOU GIJUTSU KENKYU KUMIAI

Original Assignee

GOSEI SENRIYOU GIJUTSU KENKYU KUMIAI

Priority date

1981-12-16

Filing date

1981-12-16

Publication date

1983-06-22

1981-12-16 Application filed by GOSEI SENRIYOU GIJUTSU KENKYU KUMIAI filed Critical GOSEI SENRIYOU GIJUTSU KENKYU KUMIAI

1981-12-16 Priority to JP20400181A priority Critical patent/JPS58104954A/ja

1983-06-22 Publication of JPS58104954A publication Critical patent/JPS58104954A/ja

1991-01-17 Publication of JPH032909B2 publication Critical patent/JPH032909B2/ja

Status Granted legal-status Critical Current

Links

238000004043 dyeing Methods 0.000 title claims abstract description 25
239000000835 fiber Substances 0.000 title claims abstract description 21
-1 monoazo compound Chemical class 0.000 title claims abstract description 18
230000002209 hydrophobic effect Effects 0.000 title claims abstract description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims 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 1
238000005859 coupling reaction Methods 0.000 abstract description 12
230000008878 coupling Effects 0.000 abstract description 10
238000010168 coupling process Methods 0.000 abstract description 10
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
239000002253 acid Substances 0.000 abstract description 6
150000001875 compounds Chemical class 0.000 abstract description 5
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 5
238000005406 washing Methods 0.000 abstract description 4
239000000463 material Substances 0.000 abstract description 3
229910000029 sodium carbonate Inorganic materials 0.000 abstract description 3
PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 abstract description 2
238000000859 sublimation Methods 0.000 abstract description 2
230000008022 sublimation Effects 0.000 abstract description 2
MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 abstract 1
230000002152 alkylating effect Effects 0.000 abstract 1
238000000354 decomposition reaction Methods 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
230000035945 sensitivity Effects 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 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
238000010438 heat treatment Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000002280 amphoteric surfactant Substances 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
229960003237 betaine Drugs 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
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 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
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 2
239000006185 dispersion Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
BFXQGXBFHFANFT-UHFFFAOYSA-N n-(2-cyanophenyl)nitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1C#N BFXQGXBFHFANFT-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 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
238000010186 staining Methods 0.000 description 2
238000010025 steaming Methods 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
RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-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
102100023701 C-C motif chemokine 18 Human genes 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
101100382881 Homo sapiens CCL18 gene Proteins 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
239000004952 Polyamide Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
238000009835 boiling Methods 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
238000004140 cleaning Methods 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
150000002148 esters Chemical class 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000004898 kneading Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 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
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 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000010292 orthophenyl phenol Nutrition 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 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
239000010959 steel Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1