DE2158924A1 - Monoazofarbstoffe - Google Patents
MonoazofarbstoffeInfo
- Publication number
- DE2158924A1 DE2158924A1 DE19712158924 DE2158924A DE2158924A1 DE 2158924 A1 DE2158924 A1 DE 2158924A1 DE 19712158924 DE19712158924 DE 19712158924 DE 2158924 A DE2158924 A DE 2158924A DE 2158924 A1 DE2158924 A1 DE 2158924A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- amino
- alkyl
- phenyl
- hydrogen
- 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 23
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical compound [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 7
- -1 naphthylene radical Chemical class 0.000 claims description 58
- 239000000460 chlorine Substances 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 17
- 239000004952 Polyamide Substances 0.000 claims description 16
- 229920002647 polyamide Polymers 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000005521 carbonamide group Chemical group 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229920002994 synthetic fiber Polymers 0.000 claims description 4
- 239000012209 synthetic fiber Substances 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 27
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 13
- 229940018564 m-phenylenediamine Drugs 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000004677 Nylon Substances 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 206010039587 Scarlet Fever Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- WRZDSZXJYGDDBE-UHFFFAOYSA-N 2-phenoxybenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1OC1=CC=CC=C1 WRZDSZXJYGDDBE-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JTLBRJZAWNVZCJ-UHFFFAOYSA-N (1,5-diaminocyclohexa-2,4-dien-1-yl)-phenylmethanone Chemical compound NC1(C(=O)C2=CC=CC=C2)CC(=CC=C1)N JTLBRJZAWNVZCJ-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-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
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 1
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical class NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- SWDHKZPAUHBMHV-UHFFFAOYSA-N 2-ethoxybenzenesulfonic acid Chemical compound CCOC1=CC=CC=C1S(O)(=O)=O SWDHKZPAUHBMHV-UHFFFAOYSA-N 0.000 description 1
- FQBAMYDJEQUGNV-UHFFFAOYSA-N 2-methoxybenzenesulfonic acid Chemical compound COC1=CC=CC=C1S(O)(=O)=O FQBAMYDJEQUGNV-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- SQBQMRMRIXXYCS-UHFFFAOYSA-N 3-[(4-aminophenyl)sulfonylamino]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC(S(O)(=O)=O)=C1 SQBQMRMRIXXYCS-UHFFFAOYSA-N 0.000 description 1
- VGIJZDWQVCXVNL-UHFFFAOYSA-N 3-butoxyphenol Chemical compound CCCCOC1=CC=CC(O)=C1 VGIJZDWQVCXVNL-UHFFFAOYSA-N 0.000 description 1
- LUNFYXBUYWMPBY-UHFFFAOYSA-N 3-chloro-n-ethylaniline Chemical compound CCNC1=CC=CC(Cl)=C1 LUNFYXBUYWMPBY-UHFFFAOYSA-N 0.000 description 1
- VBIKLMJHBGFTPV-UHFFFAOYSA-N 3-ethoxyphenol Chemical compound CCOC1=CC=CC(O)=C1 VBIKLMJHBGFTPV-UHFFFAOYSA-N 0.000 description 1
- CVXZPKUQXOWDPY-UHFFFAOYSA-N 3-isocyanatoaniline Chemical compound NC1=CC=CC(N=C=O)=C1 CVXZPKUQXOWDPY-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- CITSVDLEKMWTER-UHFFFAOYSA-N 5-chloro-2-ethylphenol Chemical group CCC1=CC=C(Cl)C=C1O CITSVDLEKMWTER-UHFFFAOYSA-N 0.000 description 1
- JCXKWQYJLMZMHG-UHFFFAOYSA-N CC(=O)C1(CC(=CC=C1)N)N Chemical compound CC(=O)C1(CC(=CC=C1)N)N JCXKWQYJLMZMHG-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 101710109085 Cysteine synthase, chloroplastic/chromoplastic Proteins 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- FYWIYYNVVUXXGD-UHFFFAOYSA-N NC(C=C1)=CC=C1S(NC(C=C1)=CC(S(C(C=C(C=C2)NS(C(C=C3)=CC=C3N)(=O)=O)=C2OC2=CC=CC=C2)(=O)=O)=C1OC1=CC=CC=C1)(=O)=O Chemical compound NC(C=C1)=CC=C1S(NC(C=C1)=CC(S(C(C=C(C=C2)NS(C(C=C3)=CC=C3N)(=O)=O)=C2OC2=CC=CC=C2)(=O)=O)=C1OC1=CC=CC=C1)(=O)=O FYWIYYNVVUXXGD-UHFFFAOYSA-N 0.000 description 1
- QCGTXJJHQPPZTN-UHFFFAOYSA-N NC1(CC(=CC=C1)N)C=O Chemical compound NC1(CC(=CC=C1)N)C=O QCGTXJJHQPPZTN-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FWVYIDMJEIHMMX-UHFFFAOYSA-N [3-[(4-amino-2,5-dichlorophenyl)sulfonylamino]phenyl]methanesulfonic acid Chemical compound C1=C(Cl)C(N)=CC(Cl)=C1S(=O)(=O)NC1=CC=CC(CS(O)(=O)=O)=C1 FWVYIDMJEIHMMX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940005667 ethyl salicylate Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 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 1
- FBGJJTQNZVNEQU-UHFFFAOYSA-N n,3-dimethylaniline Chemical compound CNC1=CC=CC(C)=C1 FBGJJTQNZVNEQU-UHFFFAOYSA-N 0.000 description 1
- XTXFAVHDQCHWCS-UHFFFAOYSA-N n-(3-amino-4-ethoxyphenyl)acetamide Chemical compound CCOC1=CC=C(NC(C)=O)C=C1N XTXFAVHDQCHWCS-UHFFFAOYSA-N 0.000 description 1
- BIYQLXLSSLKTNE-UHFFFAOYSA-N n-(3-aminophenyl)-2-hydroxyacetamide Chemical compound NC1=CC=CC(NC(=O)CO)=C1 BIYQLXLSSLKTNE-UHFFFAOYSA-N 0.000 description 1
- HKDFWZNDGAOZCK-UHFFFAOYSA-N n-(3-aminophenyl)-n-(2-hydroxyethyl)acetamide Chemical compound OCCN(C(=O)C)C1=CC=CC(N)=C1 HKDFWZNDGAOZCK-UHFFFAOYSA-N 0.000 description 1
- 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 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
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- GUYMMHOQXYZMJQ-UHFFFAOYSA-N n-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 1
- KERKSHQWMCWPBT-UHFFFAOYSA-N n-phenylacetamide;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.CC(=O)NC1=CC=CC=C1 KERKSHQWMCWPBT-UHFFFAOYSA-N 0.000 description 1
- HKTBRYQNVRPBCF-UHFFFAOYSA-N nitrobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.[O-][N+](=O)C1=CC=CC=C1 HKTBRYQNVRPBCF-UHFFFAOYSA-N 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- NBADVBNRRHVIAO-UHFFFAOYSA-N phenylsulfanol Chemical compound OSC1=CC=CC=C1 NBADVBNRRHVIAO-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011734 sodium Substances 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
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE791873D BE791873A (fr) | 1971-11-27 | Colorants monoazoiques | |
| DE19712158924 DE2158924A1 (de) | 1971-11-27 | 1971-11-27 | Monoazofarbstoffe |
| JP11628772A JPS4864122A (https=) | 1971-11-27 | 1972-11-21 | |
| NL7215989A NL7215989A (https=) | 1971-11-27 | 1972-11-24 | |
| CH77674A CH550229A (de) | 1971-11-27 | 1972-11-24 | Verfahren zur herstellung von monoazofarbstoffen. |
| IT3209872A IT971215B (it) | 1971-11-27 | 1972-11-24 | Coloranti monoazoici |
| GB5466872A GB1379328A (en) | 1971-11-27 | 1972-11-27 | Monoazo dyestuffs |
| FR7242038A FR2161112A1 (https=) | 1971-11-27 | 1972-11-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712158924 DE2158924A1 (de) | 1971-11-27 | 1971-11-27 | Monoazofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2158924A1 true DE2158924A1 (de) | 1973-05-30 |
Family
ID=5826346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712158924 Pending DE2158924A1 (de) | 1971-11-27 | 1971-11-27 | Monoazofarbstoffe |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4864122A (https=) |
| BE (1) | BE791873A (https=) |
| CH (1) | CH550229A (https=) |
| DE (1) | DE2158924A1 (https=) |
| FR (1) | FR2161112A1 (https=) |
| GB (1) | GB1379328A (https=) |
| IT (1) | IT971215B (https=) |
| NL (1) | NL7215989A (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2422465A1 (de) * | 1974-05-09 | 1975-12-04 | Bayer Ag | Azofarbstoffe |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3133919A1 (de) * | 1981-08-27 | 1983-03-17 | Bayer Ag, 5090 Leverkusen | Saure monoazofarbstoffe sowie deren verwendung zum faerben von polyamiden |
| DE3133915A1 (de) * | 1981-08-27 | 1983-03-17 | Bayer Ag, 5090 Leverkusen | Saure monoazofarbstoffe und deren verwendung zum faerben von polyamiden |
| JPS58104956A (ja) * | 1981-12-18 | 1983-06-22 | Sumitomo Chem Co Ltd | アゾ染料の製造法 |
-
0
- BE BE791873D patent/BE791873A/xx unknown
-
1971
- 1971-11-27 DE DE19712158924 patent/DE2158924A1/de active Pending
-
1972
- 1972-11-21 JP JP11628772A patent/JPS4864122A/ja active Pending
- 1972-11-24 CH CH77674A patent/CH550229A/xx not_active IP Right Cessation
- 1972-11-24 NL NL7215989A patent/NL7215989A/xx unknown
- 1972-11-24 IT IT3209872A patent/IT971215B/it active
- 1972-11-27 GB GB5466872A patent/GB1379328A/en not_active Expired
- 1972-11-27 FR FR7242038A patent/FR2161112A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2422465A1 (de) * | 1974-05-09 | 1975-12-04 | Bayer Ag | Azofarbstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| IT971215B (it) | 1974-04-30 |
| NL7215989A (https=) | 1973-05-29 |
| CH550229A (de) | 1974-06-14 |
| FR2161112A1 (https=) | 1973-07-06 |
| BE791873A (fr) | 1973-05-24 |
| JPS4864122A (https=) | 1973-09-05 |
| GB1379328A (en) | 1975-01-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2738885C2 (https=) | ||
| DE2557410C2 (de) | Disazofarbstoffe | |
| DE2353149A1 (de) | Saure disazofarbstoffe, verfahren zu ihrer herstellung und ihrer verwendung | |
| DE2201112A1 (de) | Disperse Azofarbstoffe | |
| DE2158924A1 (de) | Monoazofarbstoffe | |
| DE2141987A1 (de) | Kationische farbstoffe | |
| EP0027887B1 (de) | Azofarbstoffe, deren Herstellung und Verwendung zum Färben von Synthesefasern | |
| EP0197471B1 (de) | Azofarbstoffe mit Thiophen-Diazokomponenten | |
| DE2363603A1 (de) | Azofarbstoffe | |
| DE1644109B2 (de) | Wasserunloesliche nitromonoazofarbstoffe und verfahren zum faerben von polyesterfasern | |
| DE2714204A1 (de) | Monoazofarbstoffe | |
| DE1644135A1 (de) | Neue,wasserunloesliche Azofarbstoffe und Verfahren zu deren Herstellung | |
| DE2006261C3 (de) | SulfonsäuregruppenhaJtige Disazofarbstoffe und ihre Verwendung zum Färben und Bedrucken von natürlichen und künstlichen Polyamidfasermaterialien | |
| DE2203460C3 (de) | Monoazofarbstoffe und Verfahren zum Färben und Bedrucken | |
| DE2324198C3 (de) | Neue quaternäre Monoazofarbstoffe, Verfahren zu ihrer Herstellung und Färbeverfahren | |
| DE2263295A1 (de) | Monoazofarbstoffe | |
| AT214547B (de) | Verfahren zur Herstellung von neuen Azofarbstoffen | |
| DE2637922A1 (de) | Organische verbindungen, deren herstellung und verwendung | |
| DE2640764A1 (de) | Azofarbstoffe | |
| DE2239814C2 (de) | Monoazofarbstoffe und ihre Verwendung | |
| DE2006733B2 (de) | Eine Sulfogruppe enthaltende Disazofarbstoffe und ihre Verwendung zum Färben von Fasermaterialien aus synthetischen Polyamiden | |
| DE2453209A1 (de) | Disazofarbstoffe | |
| DE1017718B (de) | Verfahren zur Herstellung von Disazofarbstoffen | |
| AT220742B (de) | Verfahren zur Herstellung von neuen Azofarbstoffen | |
| DE2362330A1 (de) | Polyfluorierte saure azofarbstoffe |