DE2120095A1 - Wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung - Google Patents
Wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2120095A1 DE2120095A1 DE19712120095 DE2120095A DE2120095A1 DE 2120095 A1 DE2120095 A1 DE 2120095A1 DE 19712120095 DE19712120095 DE 19712120095 DE 2120095 A DE2120095 A DE 2120095A DE 2120095 A1 DE2120095 A1 DE 2120095A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- ref
- acid
- substituted
- nitro
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 12
- 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 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 233
- -1 ethoxyl Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
- 238000004043 dyeing Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 230000002209 hydrophobic effect Effects 0.000 claims 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 12
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 10
- 239000002253 acid Substances 0.000 description 7
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 4
- FNAKEOXYWBWIRT-UHFFFAOYSA-N 2,3-dibromophenol Chemical compound OC1=CC=CC(Br)=C1Br FNAKEOXYWBWIRT-UHFFFAOYSA-N 0.000 description 3
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 3
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 3
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 3
- NSVIJCUSYBZPTA-UHFFFAOYSA-N 7-methylnaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(C)=CC=C21 NSVIJCUSYBZPTA-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical class OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- XQDNFAMOIPNVES-UHFFFAOYSA-N 3,5-Dimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1 XQDNFAMOIPNVES-UHFFFAOYSA-N 0.000 description 2
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,5-dimethoxybenzoic acid Chemical compound COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 2
- VOIZNVUXCQLQHS-UHFFFAOYSA-N 3-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC(Br)=C1 VOIZNVUXCQLQHS-UHFFFAOYSA-N 0.000 description 2
- XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 2
- ZPJCBXBTQBOAKY-UHFFFAOYSA-N 3-methylnaphthalen-1-ol Chemical compound C1=CC=CC2=CC(C)=CC(O)=C21 ZPJCBXBTQBOAKY-UHFFFAOYSA-N 0.000 description 2
- SCWBSTVOWDDYHH-UHFFFAOYSA-N 4-amino-2,6-dichlorophenol;4-aminophenol Chemical compound NC1=CC=C(O)C=C1.NC1=CC(Cl)=C(O)C(Cl)=C1 SCWBSTVOWDDYHH-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- ZSUDUDXOEGHEJR-UHFFFAOYSA-N 4-methylnaphthalen-1-ol Chemical compound C1=CC=C2C(C)=CC=C(O)C2=C1 ZSUDUDXOEGHEJR-UHFFFAOYSA-N 0.000 description 2
- SCABGIMUFLBRMU-UHFFFAOYSA-N 6-methylnaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(C)=CC=C21 SCABGIMUFLBRMU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- KNTZCGBYFGEMFR-UHFFFAOYSA-N (propan-2-ylazaniumyl)formate Chemical compound CC(C)NC(O)=O KNTZCGBYFGEMFR-UHFFFAOYSA-N 0.000 description 1
- QAYITGAHWYCLIB-UHFFFAOYSA-N 1,4-dichloronaphthalen-2-ol Chemical compound C1=CC=CC2=C(Cl)C(O)=CC(Cl)=C21 QAYITGAHWYCLIB-UHFFFAOYSA-N 0.000 description 1
- FQJZPYXGPYJJIH-UHFFFAOYSA-N 1-bromonaphthalen-2-ol Chemical compound C1=CC=CC2=C(Br)C(O)=CC=C21 FQJZPYXGPYJJIH-UHFFFAOYSA-N 0.000 description 1
- VUVIRKAVBZITDO-UHFFFAOYSA-N 1-bromonaphthalene-2-carboxylic acid Chemical compound C1=CC=CC2=C(Br)C(C(=O)O)=CC=C21 VUVIRKAVBZITDO-UHFFFAOYSA-N 0.000 description 1
- RMSOEGBYNWXXBG-UHFFFAOYSA-N 1-chloronaphthalen-2-ol Chemical compound C1=CC=CC2=C(Cl)C(O)=CC=C21 RMSOEGBYNWXXBG-UHFFFAOYSA-N 0.000 description 1
- LVQCQPJRMITAJV-UHFFFAOYSA-N 1-methoxynaphthalen-2-ol Chemical compound C1=CC=C2C(OC)=C(O)C=CC2=C1 LVQCQPJRMITAJV-UHFFFAOYSA-N 0.000 description 1
- BBOCZFGVXFNCTC-UHFFFAOYSA-N 1-methylnaphthalen-2-ol Chemical compound C1=CC=C2C(C)=C(O)C=CC2=C1 BBOCZFGVXFNCTC-UHFFFAOYSA-N 0.000 description 1
- IDTDAMGQDWDZEU-UHFFFAOYSA-N 1-methylnaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(C)=C(C(O)=O)C=CC2=C1 IDTDAMGQDWDZEU-UHFFFAOYSA-N 0.000 description 1
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- OFAPWTOOMSVMIU-UHFFFAOYSA-N 2,4-dichloro-5-nitrophenol Chemical compound OC1=CC([N+]([O-])=O)=C(Cl)C=C1Cl OFAPWTOOMSVMIU-UHFFFAOYSA-N 0.000 description 1
- PHMZQTUIUCCHOX-UHFFFAOYSA-N 2,7-dimethylnaphthalene-1-carboxylic acid Chemical compound C1=CC(C)=C(C(O)=O)C2=CC(C)=CC=C21 PHMZQTUIUCCHOX-UHFFFAOYSA-N 0.000 description 1
- ZZYYOHPHSYCHQG-UHFFFAOYSA-N 2-bromo-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(Br)=C1 ZZYYOHPHSYCHQG-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- DTNSDCJFTHMDAK-UHFFFAOYSA-N 2-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C#N DTNSDCJFTHMDAK-UHFFFAOYSA-N 0.000 description 1
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 description 1
- KSTGSVANFMJGGB-UHFFFAOYSA-N 2-ethylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CC)=CC=C21 KSTGSVANFMJGGB-UHFFFAOYSA-N 0.000 description 1
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- SOWDWUPMHVDZGL-UHFFFAOYSA-N 2-methoxy-4-methylbenzoic acid Chemical compound COC1=CC(C)=CC=C1C(O)=O SOWDWUPMHVDZGL-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- IRNJRGVFXLVQEK-UHFFFAOYSA-N 2-methyl-1-phenylbutane-1,3-dione Chemical compound CC(=O)C(C)C(=O)C1=CC=CC=C1 IRNJRGVFXLVQEK-UHFFFAOYSA-N 0.000 description 1
- XXXOBNJIIZQSPT-UHFFFAOYSA-N 2-methyl-4-nitrobenzoic acid Chemical compound CC1=CC([N+]([O-])=O)=CC=C1C(O)=O XXXOBNJIIZQSPT-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- MUCCHGOWMZTLHK-UHFFFAOYSA-N 2-nitronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=CC2=C1 MUCCHGOWMZTLHK-UHFFFAOYSA-N 0.000 description 1
- OMBRWZUUZWYLAP-UHFFFAOYSA-N 3,5-dibromo-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC(Br)=C1[N+]([O-])=O OMBRWZUUZWYLAP-UHFFFAOYSA-N 0.000 description 1
- UMVOQQDNEYOJOK-UHFFFAOYSA-N 3,5-dimethylbenzoic acid Chemical compound CC1=CC(C)=CC(C(O)=O)=C1 UMVOQQDNEYOJOK-UHFFFAOYSA-N 0.000 description 1
- PQVIOPAWVAOHOA-UHFFFAOYSA-N 3-bromonaphthalen-2-ol Chemical compound C1=CC=C2C=C(Br)C(O)=CC2=C1 PQVIOPAWVAOHOA-UHFFFAOYSA-N 0.000 description 1
- NKVUYEGKHRDEBB-UHFFFAOYSA-N 3-chloro-2-methoxybenzoic acid Chemical compound COC1=C(Cl)C=CC=C1C(O)=O NKVUYEGKHRDEBB-UHFFFAOYSA-N 0.000 description 1
- WBQDMPDIVOKUFW-UHFFFAOYSA-N 3-chloro-2-methyl-4-nitrophenol Chemical compound [N+](=O)([O-])C=1C(=C(C(=CC1)O)C)Cl WBQDMPDIVOKUFW-UHFFFAOYSA-N 0.000 description 1
- BWVAMAOLWZGQDA-UHFFFAOYSA-N 3-chloronaphthalen-2-ol Chemical compound C1=CC=C2C=C(Cl)C(O)=CC2=C1 BWVAMAOLWZGQDA-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- SJTNTIRIRIPZDV-UHFFFAOYSA-N 3-methoxynaphthalen-2-ol Chemical compound C1=CC=C2C=C(O)C(OC)=CC2=C1 SJTNTIRIRIPZDV-UHFFFAOYSA-N 0.000 description 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
- JFBYGMUJXBUWEO-UHFFFAOYSA-N 3-methylnaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C)=CC2=C1 JFBYGMUJXBUWEO-UHFFFAOYSA-N 0.000 description 1
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
- CQUUKGPBMDUWMP-UHFFFAOYSA-N 3-propan-2-ylnaphthalen-2-ol Chemical compound C1=CC=C2C=C(O)C(C(C)C)=CC2=C1 CQUUKGPBMDUWMP-UHFFFAOYSA-N 0.000 description 1
- ISMIOKMACYQVSC-UHFFFAOYSA-N 4,6-dibromonaphthalen-2-ol Chemical compound C1=C(Br)C=CC2=CC(O)=CC(Br)=C21 ISMIOKMACYQVSC-UHFFFAOYSA-N 0.000 description 1
- AYWLUFDSHXCPQF-UHFFFAOYSA-N 4,6-dimethylnaphthalene-2-carboxylic acid Chemical compound CC1=CC(=CC2=CC=C(C=C12)C)C(=O)O AYWLUFDSHXCPQF-UHFFFAOYSA-N 0.000 description 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 1
- JFEQJWNWRKCUBV-UHFFFAOYSA-N 4-bromo-2-chloronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C(Cl)C=C(Br)C2=C1 JFEQJWNWRKCUBV-UHFFFAOYSA-N 0.000 description 1
- XEABVLJDZHURAD-UHFFFAOYSA-N 4-bromo-2-ethylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CC)=CC(Br)=C21 XEABVLJDZHURAD-UHFFFAOYSA-N 0.000 description 1
- SVSBFTMMMWFONE-UHFFFAOYSA-N 4-bromo-2-methyl-6-nitrobenzoic acid Chemical compound CC1=CC(Br)=CC([N+]([O-])=O)=C1C(O)=O SVSBFTMMMWFONE-UHFFFAOYSA-N 0.000 description 1
- RYGNNSNXVBBMSK-UHFFFAOYSA-N 4-bromo-2-nitronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C(Br)C2=C1 RYGNNSNXVBBMSK-UHFFFAOYSA-N 0.000 description 1
- PQNQMYMGUXGWTG-UHFFFAOYSA-N 4-bromonaphthalen-2-ol Chemical compound C1=CC=CC2=CC(O)=CC(Br)=C21 PQNQMYMGUXGWTG-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- LECDFGVDGCRITG-UHFFFAOYSA-N 4-chloro-1-methylnaphthalen-2-ol Chemical compound CC1=C(C=C(C2=CC=CC=C12)Cl)O LECDFGVDGCRITG-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- XYHQAQRXVQZBQV-UHFFFAOYSA-N 4-ethoxynaphthalen-1-ol Chemical compound C1=CC=C2C(OCC)=CC=C(O)C2=C1 XYHQAQRXVQZBQV-UHFFFAOYSA-N 0.000 description 1
- PLFCGQDMWZGHOQ-UHFFFAOYSA-N 4-ethylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(CC)=CC=C(C(O)=O)C2=C1 PLFCGQDMWZGHOQ-UHFFFAOYSA-N 0.000 description 1
- 125000006418 4-methylphenylsulfonyl group Chemical group 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- AUIRNGLMBHIITH-UHFFFAOYSA-N 4-nitronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=C([N+]([O-])=O)C2=C1 AUIRNGLMBHIITH-UHFFFAOYSA-N 0.000 description 1
- PSUZGCHZHKKTTP-UHFFFAOYSA-N 4-propan-2-ylnaphthalen-1-ol Chemical compound C1=CC=C2C(C(C)C)=CC=C(O)C2=C1 PSUZGCHZHKKTTP-UHFFFAOYSA-N 0.000 description 1
- OVBHSQOJQFXCAH-UHFFFAOYSA-N 4-propan-2-ylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(C)C)=CC=C(C(O)=O)C2=C1 OVBHSQOJQFXCAH-UHFFFAOYSA-N 0.000 description 1
- KEGNUIZNBCHWLZ-UHFFFAOYSA-N 5,8-dichloronaphthalen-1-ol Chemical compound C1=CC(Cl)=C2C(O)=CC=CC2=C1Cl KEGNUIZNBCHWLZ-UHFFFAOYSA-N 0.000 description 1
- UGNAVPLMTQHVJH-UHFFFAOYSA-N 5,8-dichloronaphthalene-1-carboxylic acid Chemical compound C1=CC(Cl)=C2C(C(=O)O)=CC=CC2=C1Cl UGNAVPLMTQHVJH-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
- SEENCYZQHCUTSB-UHFFFAOYSA-N 5-bromo-2-methylbenzoic acid Chemical compound CC1=CC=C(Br)C=C1C(O)=O SEENCYZQHCUTSB-UHFFFAOYSA-N 0.000 description 1
- BZCYULYTYLSGBX-UHFFFAOYSA-N 5-bromonaphthalen-2-ol Chemical compound BrC1=CC=CC2=CC(O)=CC=C21 BZCYULYTYLSGBX-UHFFFAOYSA-N 0.000 description 1
- QPOQPJDDJJNVRY-UHFFFAOYSA-N 5-bromonaphthalene-2-carboxylic acid Chemical compound BrC1=CC=CC2=CC(C(=O)O)=CC=C21 QPOQPJDDJJNVRY-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- XOAHGFTUIRAVTN-UHFFFAOYSA-N 5-methoxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(OC)=CC=CC2=C1C(O)=O XOAHGFTUIRAVTN-UHFFFAOYSA-N 0.000 description 1
- QDECJNWVPYZYIP-UHFFFAOYSA-N 5-methoxynaphthalene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(OC)=CC=CC2=C1 QDECJNWVPYZYIP-UHFFFAOYSA-N 0.000 description 1
- RIXNIZKEKXPLIT-UHFFFAOYSA-N 5-nitronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=CC2=C1[N+]([O-])=O RIXNIZKEKXPLIT-UHFFFAOYSA-N 0.000 description 1
- DGDAVTPQCQXLGU-UHFFFAOYSA-N 5437-38-7 Chemical compound CC1=CC=CC(C(O)=O)=C1[N+]([O-])=O DGDAVTPQCQXLGU-UHFFFAOYSA-N 0.000 description 1
- JHGMBKMPUBNWBB-UHFFFAOYSA-N 6,7-dimethylnaphthalen-1-ol Chemical compound C1=CC(O)=C2C=C(C)C(C)=CC2=C1 JHGMBKMPUBNWBB-UHFFFAOYSA-N 0.000 description 1
- IPELRBKDSIGNSI-UHFFFAOYSA-N 6,7-dimethylnaphthalen-2-ol Chemical compound C1=C(O)C=C2C=C(C)C(C)=CC2=C1 IPELRBKDSIGNSI-UHFFFAOYSA-N 0.000 description 1
- YZBILXXOZFORFE-UHFFFAOYSA-N 6-Methoxy-2-naphthoic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(OC)=CC=C21 YZBILXXOZFORFE-UHFFFAOYSA-N 0.000 description 1
- LTNYJHPFAVZPDR-UHFFFAOYSA-N 6-bromo-1-ethylnaphthalen-2-ol Chemical compound BrC1=CC=C2C(CC)=C(O)C=CC2=C1 LTNYJHPFAVZPDR-UHFFFAOYSA-N 0.000 description 1
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 1
- CNLYNLSYCPWZQY-UHFFFAOYSA-N 6-chloronaphthalen-2-ol Chemical compound C1=C(Cl)C=CC2=CC(O)=CC=C21 CNLYNLSYCPWZQY-UHFFFAOYSA-N 0.000 description 1
- WIIBBUOXRNBMDS-UHFFFAOYSA-N 6-ethoxynaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(OCC)=CC=C21 WIIBBUOXRNBMDS-UHFFFAOYSA-N 0.000 description 1
- WWPKRXOOVICNJY-UHFFFAOYSA-N 6-methoxynaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(OC)=CC=C21 WWPKRXOOVICNJY-UHFFFAOYSA-N 0.000 description 1
- SHWKZEFERHFBTQ-UHFFFAOYSA-N 6-methylnaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(C)=CC=C21 SHWKZEFERHFBTQ-UHFFFAOYSA-N 0.000 description 1
- VOCNMTIGMYPFPY-UHFFFAOYSA-N 6-methylnaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C)=CC=C21 VOCNMTIGMYPFPY-UHFFFAOYSA-N 0.000 description 1
- VWSBGGRCEQOTNU-UHFFFAOYSA-N 7-bromonaphthalen-2-ol Chemical compound C1=CC(Br)=CC2=CC(O)=CC=C21 VWSBGGRCEQOTNU-UHFFFAOYSA-N 0.000 description 1
- QSDSWPOSISCSSI-UHFFFAOYSA-N 7-chloronaphthalen-2-ol Chemical compound C1=CC(Cl)=CC2=CC(O)=CC=C21 QSDSWPOSISCSSI-UHFFFAOYSA-N 0.000 description 1
- UNFNRIIETORURP-UHFFFAOYSA-N 7-methoxynaphthalen-2-ol Chemical compound C1=CC(O)=CC2=CC(OC)=CC=C21 UNFNRIIETORURP-UHFFFAOYSA-N 0.000 description 1
- IWXCQSJYXQESCP-UHFFFAOYSA-N 7-methoxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=CC(OC)=CC=C21 IWXCQSJYXQESCP-UHFFFAOYSA-N 0.000 description 1
- JJAGLIPYTVMFTL-UHFFFAOYSA-N 7-methoxynaphthalene-2-carboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(OC)=CC=C21 JJAGLIPYTVMFTL-UHFFFAOYSA-N 0.000 description 1
- RJUFYSUNQJMDLZ-UHFFFAOYSA-N 8-bromonaphthalen-1-ol Chemical compound C1=CC(Br)=C2C(O)=CC=CC2=C1 RJUFYSUNQJMDLZ-UHFFFAOYSA-N 0.000 description 1
- PJRXIIFRDDJZSP-UHFFFAOYSA-N 8-bromonaphthalen-2-ol Chemical compound C1=CC=C(Br)C2=CC(O)=CC=C21 PJRXIIFRDDJZSP-UHFFFAOYSA-N 0.000 description 1
- QVKBELCKHUHPRW-UHFFFAOYSA-N 8-chloronaphthalen-1-ol Chemical compound C1=CC(Cl)=C2C(O)=CC=CC2=C1 QVKBELCKHUHPRW-UHFFFAOYSA-N 0.000 description 1
- XSMAIDLOXKONHB-UHFFFAOYSA-N 8-chloronaphthalen-2-ol Chemical compound C1=CC=C(Cl)C2=CC(O)=CC=C21 XSMAIDLOXKONHB-UHFFFAOYSA-N 0.000 description 1
- NMLPABRPTHFKMQ-UHFFFAOYSA-N 8-methoxynaphthalen-1-ol Chemical compound C1=CC(O)=C2C(OC)=CC=CC2=C1 NMLPABRPTHFKMQ-UHFFFAOYSA-N 0.000 description 1
- AGWGITMRMDHPGN-UHFFFAOYSA-N 8-methoxynaphthalene-1-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(OC)=CC=CC2=C1 AGWGITMRMDHPGN-UHFFFAOYSA-N 0.000 description 1
- WVVFTEVROJKIJA-UHFFFAOYSA-N 8-methoxynaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(OC)=CC=CC2=C1 WVVFTEVROJKIJA-UHFFFAOYSA-N 0.000 description 1
- FLBHUCKQJRXXQB-UHFFFAOYSA-N 8-methylnaphthalene-1-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C)=CC=CC2=C1 FLBHUCKQJRXXQB-UHFFFAOYSA-N 0.000 description 1
- YZHNXQGDCFWEPO-UHFFFAOYSA-N 8-nitronaphthalen-2-ol Chemical compound C1=CC=C([N+]([O-])=O)C2=CC(O)=CC=C21 YZHNXQGDCFWEPO-UHFFFAOYSA-N 0.000 description 1
- USMKVLABRYGBJX-UHFFFAOYSA-N 8-nitronaphthalene-1-carboxylic acid Chemical compound C1=CC([N+]([O-])=O)=C2C(C(=O)O)=CC=CC2=C1 USMKVLABRYGBJX-UHFFFAOYSA-N 0.000 description 1
- QAYNSPOKTRVZRC-UHFFFAOYSA-N 99-60-5 Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl QAYNSPOKTRVZRC-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 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
- 150000003931 anilides Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CKTNHGVJKUQEBM-UHFFFAOYSA-N ethylazanide Chemical compound CC[NH-] CKTNHGVJKUQEBM-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000005027 hydroxyaryl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- HAZAXSFZTQULFE-UHFFFAOYSA-N phenyl 3-aminobenzoate Chemical compound NC1=CC=CC(C(=O)OC=2C=CC=CC=2)=C1 HAZAXSFZTQULFE-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical class OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C09B29/34—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
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712120095 DE2120095A1 (de) | 1971-04-24 | 1971-04-24 | Wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung |
| NL7204977A NL7204977A (enrdf_load_stackoverflow) | 1971-04-24 | 1972-04-13 | |
| IT23410/72A IT954842B (it) | 1971-04-24 | 1972-04-19 | Coloranti mono azoici insolubili in acqua e procedimento per la loro preparazione |
| BE782424A BE782424A (fr) | 1971-04-24 | 1972-04-20 | Colorants monoazoiques |
| BR2466/72A BR7202466D0 (pt) | 1971-04-24 | 1972-04-20 | Processo para a preparacao de novos corantes monoazoicos nao hidrossoluveis processo para tingimento e estampagem de materiais sinteticos hidrofobos com emprego dos ditos corantes e materiais assim tingidos ou estampados |
| DD162445A DD105623A5 (enrdf_load_stackoverflow) | 1971-04-24 | 1972-04-20 | |
| CA140,231A CA958006A (en) | 1971-04-24 | 1972-04-21 | Monoazo dyes |
| SU1776272A SU489354A3 (ru) | 1971-04-24 | 1972-04-21 | Способ крашени и набивки текстильных материалов |
| AT353272A AT309620B (de) | 1971-04-24 | 1972-04-21 | Verfahren zur Herstellung von neuen, wasserunlöslichen Monoazofarbstoffen |
| FR7214181A FR2134400B1 (enrdf_load_stackoverflow) | 1971-04-24 | 1972-04-21 | |
| AU41455/72A AU468752B2 (en) | 1971-04-24 | 1972-04-21 | Monoazo dyes |
| ZA722696A ZA722696B (en) | 1971-04-24 | 1972-04-21 | Monoazo dyes |
| ES402044A ES402044A1 (es) | 1971-04-24 | 1972-04-24 | Procedimiento para la obtencion de colorantes monoazoicos hidroinsolubles. |
| GB1883872A GB1388701A (en) | 1971-04-24 | 1972-04-24 | Monoazo dyestuffs containing hydroxypyridone residues |
| CH604672A CH566370A5 (enrdf_load_stackoverflow) | 1971-04-24 | 1972-04-24 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712120095 DE2120095A1 (de) | 1971-04-24 | 1971-04-24 | Wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2120095A1 true DE2120095A1 (de) | 1972-11-02 |
Family
ID=5805799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712120095 Pending DE2120095A1 (de) | 1971-04-24 | 1971-04-24 | Wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung |
Country Status (15)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH471861A (de) * | 1968-01-18 | 1969-04-30 | Sandoz Ag | Verfahren zur Herstellung von Monoazoverbindungen |
| CH503781A (de) * | 1968-05-15 | 1971-02-28 | Sandoz Ag | Verfahren zur Herstellung von basischen Farbstoffen |
| DE1917278B2 (de) * | 1969-04-03 | 1974-06-27 | Basf Ag, 6700 Ludwigshafen | Monoazofarbstoffe, Verfahren zu deren Herstellung und Farbstoffzubereitungen |
-
1971
- 1971-04-24 DE DE19712120095 patent/DE2120095A1/de active Pending
-
1972
- 1972-04-13 NL NL7204977A patent/NL7204977A/xx not_active Application Discontinuation
- 1972-04-19 IT IT23410/72A patent/IT954842B/it active
- 1972-04-20 BR BR2466/72A patent/BR7202466D0/pt unknown
- 1972-04-20 DD DD162445A patent/DD105623A5/xx unknown
- 1972-04-20 BE BE782424A patent/BE782424A/xx unknown
- 1972-04-21 AU AU41455/72A patent/AU468752B2/en not_active Expired
- 1972-04-21 FR FR7214181A patent/FR2134400B1/fr not_active Expired
- 1972-04-21 AT AT353272A patent/AT309620B/de not_active IP Right Cessation
- 1972-04-21 CA CA140,231A patent/CA958006A/en not_active Expired
- 1972-04-21 SU SU1776272A patent/SU489354A3/ru active
- 1972-04-21 ZA ZA722696A patent/ZA722696B/xx unknown
- 1972-04-24 ES ES402044A patent/ES402044A1/es not_active Expired
- 1972-04-24 GB GB1883872A patent/GB1388701A/en not_active Expired
- 1972-04-24 CH CH604672A patent/CH566370A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1388701A (en) | 1975-03-26 |
| IT954842B (it) | 1973-09-15 |
| BR7202466D0 (pt) | 1973-06-12 |
| DD105623A5 (enrdf_load_stackoverflow) | 1974-05-05 |
| ES402044A1 (es) | 1975-11-01 |
| FR2134400B1 (enrdf_load_stackoverflow) | 1974-12-20 |
| NL7204977A (enrdf_load_stackoverflow) | 1972-10-26 |
| AU468752B2 (en) | 1976-01-22 |
| SU489354A3 (ru) | 1975-10-25 |
| ZA722696B (en) | 1973-02-28 |
| FR2134400A1 (enrdf_load_stackoverflow) | 1972-12-08 |
| CH566370A5 (enrdf_load_stackoverflow) | 1975-09-15 |
| CA958006A (en) | 1974-11-19 |
| AU4145572A (en) | 1973-10-25 |
| AT309620B (de) | 1973-08-27 |
| BE782424A (fr) | 1972-10-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1544446C3 (de) | Von Sulfon- und Carbonsäuregruppen freie wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| CH638237A5 (de) | Farbstoffe der cumarinreihe und deren herstellung. | |
| DE1901712A1 (de) | Verfahren zur Herstellung von Azoverbindungen | |
| DE2120095A1 (de) | Wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE2254017C2 (de) | Wasserunlösliche Azofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE2531445B2 (de) | Sulfogruppenfreie wasserloesliche azofarbstoffe und deren verwendung zum faerben und/oder bedrucken von synthetischen textilfasern | |
| EP0100008A1 (de) | Neue Azofarbstoffe, ihre Herstellung und Verwendung | |
| DE2147759A1 (de) | Wasserunloesliche monoazofarbstoffe und verfahren zu ihrer herstellung | |
| DE2008491C3 (de) | Benzoxanthenfarbstoffe und Verfahren zu ihrer Herstellung | |
| DE1239421B (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE1298663B (de) | Verfahren zur Herstellung wasserunloeslicher Disazofarbstoffe | |
| DE1935482A1 (de) | Azoverbindungen,ihre Herstellung und Verwendung | |
| CH324391A (de) | Verfahren zur Herstellung neuer kobalthaltiger Azofarbstoffe | |
| AT232623B (de) | Verfahren zur Herstellung von neuen Diazapolymethinfarbstoffen | |
| DE2824710A1 (de) | Wasserunloesliche monoazofarbstoffe | |
| DE4121754B4 (de) | Azo-Dispersionsfarbstoffe | |
| DE1644122C3 (de) | Sulfonsäure- und carbonsäuregruppenfreie wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE2212755A1 (de) | Wasserunloesliche monoazofarbstoffe und verfahren zu ihrer herstellung | |
| DE2116315B2 (de) | Monoazofarbstoffe, Verfahren zu ihrer Herstellung und Verwendung | |
| DE3536718A1 (de) | Monoazoverbindungen | |
| DE2338089A1 (de) | Wasserunloesliche monoazofarbstoffe und verfahren zu ihrer herstellung | |
| DE1644122B2 (de) | Sulfonsaeure- und carbonsaeuregruppenfreie wasserunloesliche monoazofarbstoffe und verfahren zu ihrer herstellung | |
| DE2523632A1 (de) | Wasserunloesliche monoazofarbstoffe und verfahren zu ihrer herstellung | |
| DE1719090A1 (de) | Verfahren zur Herstellung von Dispersionsfarbstoffen der heterocyclischen Reihe | |
| DE2438497A1 (de) | Azofarbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal | ||
| OGA | New person/name/address of the applicant |