JPH0411587B2 - - Google Patents
Info
- Publication number
- JPH0411587B2 JPH0411587B2 JP56173164A JP17316481A JPH0411587B2 JP H0411587 B2 JPH0411587 B2 JP H0411587B2 JP 56173164 A JP56173164 A JP 56173164A JP 17316481 A JP17316481 A JP 17316481A JP H0411587 B2 JPH0411587 B2 JP H0411587B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- formula
- alkyl group
- Prior art date
- 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.)
- Expired - Lifetime
Links
- -1 sulfophenyl group Chemical group 0.000 claims description 77
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000005859 coupling reaction Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 238000004043 dyeing Methods 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 239000004952 Polyamide Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229920002647 polyamide Polymers 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 15
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004964 sulfoalkyl group Chemical group 0.000 claims description 5
- 210000002268 wool Anatomy 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000002347 octyl 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])[H] 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- 239000000980 acid dye Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229920002994 synthetic fiber Polymers 0.000 claims 1
- 239000004758 synthetic textile Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 87
- 239000000243 solution Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 230000008878 coupling Effects 0.000 description 24
- 238000010168 coupling process Methods 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 17
- 238000001914 filtration Methods 0.000 description 15
- 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 description 15
- 239000000203 mixture Substances 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 238000006193 diazotization reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- GQBONCZDJQXPLV-UHFFFAOYSA-N 4-aminoisoindole-1,3-dione Chemical compound NC1=CC=CC2=C1C(=O)NC2=O GQBONCZDJQXPLV-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- 239000008233 hard water Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical class NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- KFIRODWJCYBBHY-UHFFFAOYSA-N 3-nitrophthalic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1C(O)=O KFIRODWJCYBBHY-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 3
- VIACAIAQHPLINF-UHFFFAOYSA-N n-benzyl-n-ethyl-3-methylaniline Chemical compound C=1C=CC(C)=CC=1N(CC)CC1=CC=CC=C1 VIACAIAQHPLINF-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 159000000000 sodium salts Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- KRNUKKZDGDAWBF-UHFFFAOYSA-N 2-(n-ethyl-n-m-toluidino)ethanol Chemical compound OCCN(CC)C1=CC=CC(C)=C1 KRNUKKZDGDAWBF-UHFFFAOYSA-N 0.000 description 2
- UZCKDWUWEAHDQG-UHFFFAOYSA-N 3-(5-amino-1,3-dioxoisoindol-2-yl)propanenitrile Chemical compound NC1=CC=C2C(=O)N(CCC#N)C(=O)C2=C1 UZCKDWUWEAHDQG-UHFFFAOYSA-N 0.000 description 2
- WSCIDTFVZAVVFU-UHFFFAOYSA-N 4-[2-(4-aminophenyl)ethyl]-1,3-dioxoisoindole-2-sulfonic acid Chemical compound C1=CC(N)=CC=C1CCC1=CC=CC2=C1C(=O)N(S(O)(=O)=O)C2=O WSCIDTFVZAVVFU-UHFFFAOYSA-N 0.000 description 2
- SLBQXWXKPNIVSQ-UHFFFAOYSA-N 4-nitrophthalic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1C(O)=O SLBQXWXKPNIVSQ-UHFFFAOYSA-N 0.000 description 2
- VZUVOYFTHDDTLB-UHFFFAOYSA-N 5-amino-2-cyclohexylisoindole-1,3-dione Chemical compound O=C1C2=CC(N)=CC=C2C(=O)N1C1CCCCC1 VZUVOYFTHDDTLB-UHFFFAOYSA-N 0.000 description 2
- ANYWGXDASKQYAD-UHFFFAOYSA-N 5-nitroisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)NC(=O)C2=C1 ANYWGXDASKQYAD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 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 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000012113 quantitative test Methods 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- YUPGGFIIOBISGK-UHFFFAOYSA-N (2-benzyl-3-methylphenyl)-(2-ethylhexyl)sulfamic acid Chemical compound CCCCC(CC)CN(S(O)(=O)=O)C1=CC=CC(C)=C1CC1=CC=CC=C1 YUPGGFIIOBISGK-UHFFFAOYSA-N 0.000 description 1
- CBIBXWDQNAWPGN-UHFFFAOYSA-N (2-benzyl-3-methylphenyl)-cyclohexylsulfamic acid Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1N(S(O)(=O)=O)C1CCCCC1 CBIBXWDQNAWPGN-UHFFFAOYSA-N 0.000 description 1
- KVYDUPBVRBHAQW-UHFFFAOYSA-N (2-benzyl-3-methylphenyl)-ethylsulfamic acid Chemical compound CCN(S(O)(=O)=O)C1=CC=CC(C)=C1CC1=CC=CC=C1 KVYDUPBVRBHAQW-UHFFFAOYSA-N 0.000 description 1
- XMWVEBIZMYLPHK-UHFFFAOYSA-N (2-benzylphenyl)-ethylsulfamic acid Chemical compound CCN(S(O)(=O)=O)C1=CC=CC=C1CC1=CC=CC=C1 XMWVEBIZMYLPHK-UHFFFAOYSA-N 0.000 description 1
- FALCMQXTWHPRIH-UHFFFAOYSA-N 2,3-dichloroprop-1-ene Chemical compound ClCC(Cl)=C FALCMQXTWHPRIH-UHFFFAOYSA-N 0.000 description 1
- KCJMSEKNQFTARP-UHFFFAOYSA-N 2-(3-methyl-n-(3,3,5-trimethylcyclohexyl)anilino)ethanol Chemical compound C1C(C)(C)CC(C)CC1N(CCO)C1=CC=CC(C)=C1 KCJMSEKNQFTARP-UHFFFAOYSA-N 0.000 description 1
- SSQFVLRFFNZLCG-UHFFFAOYSA-N 2-(3-methylanilino)ethanesulfonic acid Chemical compound CC1=CC=CC(NCCS(O)(=O)=O)=C1 SSQFVLRFFNZLCG-UHFFFAOYSA-N 0.000 description 1
- UWZNTLRFBBTYQL-UHFFFAOYSA-N 2-(5-amino-1,3-dioxoisoindol-2-yl)-1-phenylethanesulfonic acid Chemical compound O=C1C2=CC(N)=CC=C2C(=O)N1CC(S(O)(=O)=O)C1=CC=CC=C1 UWZNTLRFBBTYQL-UHFFFAOYSA-N 0.000 description 1
- JGRBKWGKEBZQOW-UHFFFAOYSA-N 2-(n-benzyl-3-methylanilino)ethanol Chemical compound CC1=CC=CC(N(CCO)CC=2C=CC=CC=2)=C1 JGRBKWGKEBZQOW-UHFFFAOYSA-N 0.000 description 1
- SDMCKIUVIVHZSU-UHFFFAOYSA-N 2-(n-benzylanilino)ethanesulfonic acid Chemical compound C=1C=CC=CC=1N(CCS(=O)(=O)O)CC1=CC=CC=C1 SDMCKIUVIVHZSU-UHFFFAOYSA-N 0.000 description 1
- VMIORCIXXWGAGI-UHFFFAOYSA-N 2-(n-benzylanilino)ethanol Chemical compound C=1C=CC=CC=1N(CCO)CC1=CC=CC=C1 VMIORCIXXWGAGI-UHFFFAOYSA-N 0.000 description 1
- XVIYJIXLTGSPCT-UHFFFAOYSA-N 2-(n-cyclohexyl-3-methylanilino)ethanesulfonic acid Chemical compound CC1=CC=CC(N(CCS(O)(=O)=O)C2CCCCC2)=C1 XVIYJIXLTGSPCT-UHFFFAOYSA-N 0.000 description 1
- PTQDUHFWDIQXDS-UHFFFAOYSA-N 2-(n-cyclohexyl-3-methylanilino)ethanol Chemical compound CC1=CC=CC(N(CCO)C2CCCCC2)=C1 PTQDUHFWDIQXDS-UHFFFAOYSA-N 0.000 description 1
- JAKIBWZPJXEMRZ-UHFFFAOYSA-N 2-(n-cyclohexylanilino)ethanol Chemical compound C=1C=CC=CC=1N(CCO)C1CCCCC1 JAKIBWZPJXEMRZ-UHFFFAOYSA-N 0.000 description 1
- INXRCRIYDWYKAK-UHFFFAOYSA-N 2-(n-ethyl-3-methylanilino)-1-phenylethanesulfonic acid Chemical compound C=1C=CC(C)=CC=1N(CC)CC(S(O)(=O)=O)C1=CC=CC=C1 INXRCRIYDWYKAK-UHFFFAOYSA-N 0.000 description 1
- AWGYCBCAKHOAQH-UHFFFAOYSA-N 2-(n-ethylanilino)-1-phenylethanesulfonic acid Chemical compound C=1C=CC=CC=1N(CC)CC(S(O)(=O)=O)C1=CC=CC=C1 AWGYCBCAKHOAQH-UHFFFAOYSA-N 0.000 description 1
- ZRZGEUALTHTWAB-UHFFFAOYSA-N 2-[3-methyl-n-(2-phenylethyl)anilino]ethanesulfonic acid Chemical compound CC1=CC=CC(N(CCC=2C=CC=CC=2)CCS(O)(=O)=O)=C1 ZRZGEUALTHTWAB-UHFFFAOYSA-N 0.000 description 1
- VCOXWGWUDIOTMQ-UHFFFAOYSA-N 2-[3-methyl-n-(2-phenylethyl)anilino]ethanol Chemical compound CC1=CC=CC(N(CCO)CCC=2C=CC=CC=2)=C1 VCOXWGWUDIOTMQ-UHFFFAOYSA-N 0.000 description 1
- NANDKMATVOHWKQ-UHFFFAOYSA-N 2-cyclohexyl-5-nitroisoindole-1,3-dione Chemical compound O=C1C2=CC([N+](=O)[O-])=CC=C2C(=O)N1C1CCCCC1 NANDKMATVOHWKQ-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- LBWNPYYSZUSNCX-UHFFFAOYSA-N 3-(n-benzyl-3-methylanilino)propane-1-sulfonic acid Chemical compound CC1=CC=CC(N(CCCS(O)(=O)=O)CC=2C=CC=CC=2)=C1 LBWNPYYSZUSNCX-UHFFFAOYSA-N 0.000 description 1
- LHCWFKPBKQFRQP-UHFFFAOYSA-N 3-(n-benzylanilino)propane-1-sulfonic acid Chemical compound C=1C=CC=CC=1N(CCCS(=O)(=O)O)CC1=CC=CC=C1 LHCWFKPBKQFRQP-UHFFFAOYSA-N 0.000 description 1
- NOUIOMMCSFBHGP-UHFFFAOYSA-N 3-(n-cyclohexyl-3-methylanilino)propane-1-sulfonic acid Chemical compound CC1=CC=CC(N(CCCS(O)(=O)=O)C2CCCCC2)=C1 NOUIOMMCSFBHGP-UHFFFAOYSA-N 0.000 description 1
- KBUNDKRURFATFO-UHFFFAOYSA-N 3-[3-methyl-n-(2-phenylethyl)anilino]propane-1-sulfonic acid Chemical compound CC1=CC=CC(N(CCCS(O)(=O)=O)CCC=2C=CC=CC=2)=C1 KBUNDKRURFATFO-UHFFFAOYSA-N 0.000 description 1
- ULWLCNJHDDETFL-UHFFFAOYSA-N 3-[n-(2-phenylethyl)anilino]propane-1-sulfonic acid Chemical compound C=1C=CC=CC=1N(CCCS(=O)(=O)O)CCC1=CC=CC=C1 ULWLCNJHDDETFL-UHFFFAOYSA-N 0.000 description 1
- BONIIQYTWOPUQI-UHFFFAOYSA-N 4-nitroisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)NC2=O BONIIQYTWOPUQI-UHFFFAOYSA-N 0.000 description 1
- APJOGCVLBBFKRW-UHFFFAOYSA-N 5-[3-(5-amino-1,3-dioxoisoindol-2-yl)propyl]-5-(2-methylpropyl)cyclohexa-1,3-diene-1-sulfonic acid Chemical compound O=C1C2=CC=C(N)C=C2C(=O)N1CCCC1(CC(C)C)CC(S(O)(=O)=O)=CC=C1 APJOGCVLBBFKRW-UHFFFAOYSA-N 0.000 description 1
- QFLZDVDYRZEYQR-UHFFFAOYSA-N 5-amino-2-(2-bromoprop-2-enyl)isoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)N(CC(Br)=C)C(=O)C2=C1 QFLZDVDYRZEYQR-UHFFFAOYSA-N 0.000 description 1
- LKPHJRPWJOCJCK-UHFFFAOYSA-N 5-amino-2-(2-ethylhexyl)isoindole-1,3-dione Chemical compound C1=C(N)C=C2C(=O)N(CC(CC)CCCC)C(=O)C2=C1 LKPHJRPWJOCJCK-UHFFFAOYSA-N 0.000 description 1
- NMBUWDHRCOFXFM-UHFFFAOYSA-N 5-amino-2-(2-phenylethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC(N)=CC=C2C(=O)N1CCC1=CC=CC=C1 NMBUWDHRCOFXFM-UHFFFAOYSA-N 0.000 description 1
- SKMFSRZWNZERLS-UHFFFAOYSA-N 5-amino-2-(3,3,5-trimethylcyclohexyl)isoindole-1,3-dione Chemical compound C1C(C)(C)CC(C)CC1N1C(=O)C2=CC(N)=CC=C2C1=O SKMFSRZWNZERLS-UHFFFAOYSA-N 0.000 description 1
- SXGPADFJAQBTHD-UHFFFAOYSA-N 5-amino-2-(3-chloroprop-2-enyl)isoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)N(CC=CCl)C(=O)C2=C1 SXGPADFJAQBTHD-UHFFFAOYSA-N 0.000 description 1
- QDLIZJGZOIZMAK-UHFFFAOYSA-N 5-amino-2-benzylisoindole-1,3-dione Chemical compound O=C1C2=CC(N)=CC=C2C(=O)N1CC1=CC=CC=C1 QDLIZJGZOIZMAK-UHFFFAOYSA-N 0.000 description 1
- ZGDUHJHDEBBIDM-UHFFFAOYSA-N 5-amino-2-butan-2-ylisoindole-1,3-dione Chemical compound C1=C(N)C=C2C(=O)N(C(C)CC)C(=O)C2=C1 ZGDUHJHDEBBIDM-UHFFFAOYSA-N 0.000 description 1
- LEPAHWUHXOWZCL-UHFFFAOYSA-N 5-amino-2-ethylisoindole-1,3-dione Chemical compound C1=C(N)C=C2C(=O)N(CC)C(=O)C2=C1 LEPAHWUHXOWZCL-UHFFFAOYSA-N 0.000 description 1
- NUKVWBRSEGVYPZ-UHFFFAOYSA-N 5-amino-2-prop-1-enylisoindole-1,3-dione Chemical compound C1=C(N)C=C2C(=O)N(C=CC)C(=O)C2=C1 NUKVWBRSEGVYPZ-UHFFFAOYSA-N 0.000 description 1
- FXXIEDZMDGZPDJ-UHFFFAOYSA-N 5-amino-2-propan-2-ylisoindole-1,3-dione Chemical compound C1=C(N)C=C2C(=O)N(C(C)C)C(=O)C2=C1 FXXIEDZMDGZPDJ-UHFFFAOYSA-N 0.000 description 1
- PMEHKVSRSQHZHZ-UHFFFAOYSA-N 5-amino-2-propylisoindole-1,3-dione Chemical compound C1=C(N)C=C2C(=O)N(CCC)C(=O)C2=C1 PMEHKVSRSQHZHZ-UHFFFAOYSA-N 0.000 description 1
- FBBXQDASHFXIPN-UHFFFAOYSA-N 5-amino-4-bromo-2-butan-2-ylisoindole-1,3-dione Chemical compound C1=C(N)C(Br)=C2C(=O)N(C(C)CC)C(=O)C2=C1 FBBXQDASHFXIPN-UHFFFAOYSA-N 0.000 description 1
- SFKDUEHGETZFKI-UHFFFAOYSA-N 5-amino-4-bromo-2-ethylisoindole-1,3-dione Chemical compound C1=C(N)C(Br)=C2C(=O)N(CC)C(=O)C2=C1 SFKDUEHGETZFKI-UHFFFAOYSA-N 0.000 description 1
- VLHVHKMIFDUDAN-UHFFFAOYSA-N 5-amino-4-bromo-2-propan-2-ylisoindole-1,3-dione Chemical compound C1=C(N)C(Br)=C2C(=O)N(C(C)C)C(=O)C2=C1 VLHVHKMIFDUDAN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 150000001555 benzenes Chemical class 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
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- SRQRCKLCWXPIEW-UHFFFAOYSA-N ethyl-[3-methyl-2-(2-phenylethyl)phenyl]sulfamic acid Chemical compound CCN(S(O)(=O)=O)C1=CC=CC(C)=C1CCC1=CC=CC=C1 SRQRCKLCWXPIEW-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 description 1
- KNFACAHYMGIYIQ-UHFFFAOYSA-N n-ethyl-3-methyl-n-(2-phenylethyl)aniline Chemical compound C=1C=CC(C)=CC=1N(CC)CCC1=CC=CC=C1 KNFACAHYMGIYIQ-UHFFFAOYSA-N 0.000 description 1
- ZRGUOPOONSTAOZ-UHFFFAOYSA-N n-ethyl-n-(2-phenylethyl)aniline Chemical compound C=1C=CC=CC=1N(CC)CCC1=CC=CC=C1 ZRGUOPOONSTAOZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
-
- 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
- C09B29/0801—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls
- C09B29/0803—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls containing SO3H, OSO3H
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH807480 | 1980-10-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57102953A JPS57102953A (en) | 1982-06-26 |
| JPH0411587B2 true JPH0411587B2 (US20100012521A1-20100121-C00001.png) | 1992-02-28 |
Family
ID=4334746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56173164A Granted JPS57102953A (en) | 1980-10-30 | 1981-10-30 | Monoazo compound |
Country Status (4)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6008332A (en) * | 1994-02-11 | 1999-12-28 | Ciba Specialty Chemicals Corporation | Phthalimidylazo dyes, process for their preparation and the use thereof |
| TW353105B (en) * | 1994-05-30 | 1999-02-21 | Ciba Sc Holding Ag | Reactive dyes, their preparation and use |
| KR20000057281A (ko) * | 1996-11-27 | 2000-09-15 | 해리 제이. 그윈넬 | 광흡수 중합체성 조성물의 제조 방법 |
| JP4589726B2 (ja) * | 2002-11-11 | 2010-12-01 | チバ ホールディング インコーポレーテッド | フタルイミジル−アゾ染料、その調製方法及びその使用 |
| DE102006027535A1 (de) * | 2006-06-14 | 2007-12-20 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Dispersionsfarbstoffe, ihre Herstellung und ihre Verwendung |
| WO2014108357A1 (en) | 2013-01-14 | 2014-07-17 | Dystar Colours Distribution Gmbh | High wet-fast disperse dye mixtures |
| EP2754696A1 (en) | 2013-01-15 | 2014-07-16 | DyStar Colours Distribution GmbH | AOX-free navy and black disperse dye mixtures |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2018862A1 (fr) * | 1968-09-25 | 1970-06-26 | Basf Ag | Colorants monoazoiques sulfones |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3551407A (en) * | 1967-04-19 | 1970-12-29 | Basf Ag | Monoazo dyes derived from aminophthalimides |
| ES387358A1 (es) * | 1970-01-19 | 1974-01-01 | Crompton & Knowles Corp | Un metodo de fabricar un colorante acido para fibras de po-liamida naturales y sinteticas y para fibras de acetato de celulosa secundarias. |
| CA943127A (en) * | 1970-01-19 | 1974-03-05 | Crompton And Knowles Corporation | Dye intermediates, dyestuffs prepared therefrom and process for making dyes and intermediates |
| BE793232A (fr) * | 1971-12-23 | 1973-06-22 | Basf Ag | Colorants derives du phtalimide |
| US3980634A (en) * | 1973-07-02 | 1976-09-14 | Eastman Kodak Company | Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith |
| GB1504795A (en) * | 1976-01-23 | 1978-03-22 | Yorkshire Chemicals Ltd | Water-soluble monoazo dyes derived from n-substituted aminophthalimide diazo components |
| US4255326A (en) * | 1979-03-30 | 1981-03-10 | Eastman Kodak Company | Nitrogen and/or sulfur containing heterocyclic azo dyes with aniline, tetrahydroquinoline and benzomorpholine couplers having sulfate group |
| US4267104A (en) * | 1979-06-14 | 1981-05-12 | Eastman Kodak Company | Dyes from selected substituted aniline diazo components and aniline couplers containing sulfate ester groups |
-
1981
- 1981-10-26 DE DE8181810423T patent/DE3170172D1/de not_active Expired
- 1981-10-26 EP EP81810423A patent/EP0051563B1/de not_active Expired
- 1981-10-30 JP JP56173164A patent/JPS57102953A/ja active Granted
-
1986
- 1986-08-28 US US06/901,708 patent/US4734490A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2018862A1 (fr) * | 1968-09-25 | 1970-06-26 | Basf Ag | Colorants monoazoiques sulfones |
Also Published As
| Publication number | Publication date |
|---|---|
| US4734490A (en) | 1988-03-29 |
| DE3170172D1 (en) | 1985-05-30 |
| JPS57102953A (en) | 1982-06-26 |
| EP0051563B1 (de) | 1985-04-24 |
| EP0051563A1 (de) | 1982-05-12 |
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