DE2309638A1 - Dispersionsfarbstoffe der 2,6diaminopyridinreihe - Google Patents
Dispersionsfarbstoffe der 2,6diaminopyridinreiheInfo
- Publication number
- DE2309638A1 DE2309638A1 DE19732309638 DE2309638A DE2309638A1 DE 2309638 A1 DE2309638 A1 DE 2309638A1 DE 19732309638 DE19732309638 DE 19732309638 DE 2309638 A DE2309638 A DE 2309638A DE 2309638 A1 DE2309638 A1 DE 2309638A1
- Authority
- DE
- Germany
- Prior art keywords
- chg
- yellow
- red
- amino
- cyano
- 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
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical class NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 title claims description 3
- 239000006185 dispersion Substances 0.000 title description 2
- -1 carbomethoxy, carboethoxy Chemical group 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 22
- 230000008878 coupling Effects 0.000 claims description 19
- 238000010168 coupling process Methods 0.000 claims description 19
- 238000005859 coupling reaction Methods 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000000975 dye Substances 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- VRAKDAYLTPMBAW-UHFFFAOYSA-N [O-][N+](=O)ClC#N Chemical compound [O-][N+](=O)ClC#N VRAKDAYLTPMBAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000986 disperse dye Substances 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000012209 synthetic fiber Substances 0.000 claims 1
- 229920002994 synthetic fiber Polymers 0.000 claims 1
- 206010039587 Scarlet Fever Diseases 0.000 description 21
- 239000010979 ruby Substances 0.000 description 18
- 229910001750 ruby Inorganic materials 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
- 101150065749 Churc1 gene Proteins 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 102100038239 Protein Churchill Human genes 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- UNBOSJFEZZJZLR-UHFFFAOYSA-N 4-(4-nitrophenylazo)aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 UNBOSJFEZZJZLR-UHFFFAOYSA-N 0.000 description 3
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 description 3
- SQBCSDZTDXLTLE-UHFFFAOYSA-N 5-nitro-2,1-benzothiazol-3-amine Chemical compound C1=CC([N+]([O-])=O)=CC2=C(N)SN=C21 SQBCSDZTDXLTLE-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 2
- FYCKYDRDTNXECN-UHFFFAOYSA-N 2,4-dimethyl-4-phenyldiazenylcyclohexa-1,5-dien-1-amine Chemical compound CC1=C(C=CC(C1)(C)N=NC2=CC=CC=C2)N FYCKYDRDTNXECN-UHFFFAOYSA-N 0.000 description 2
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 2
- LCNDCGHEVNINRY-UHFFFAOYSA-N 2,5-dimethyl-4-phenyldiazenylaniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C=CC=CC=2)=C1C LCNDCGHEVNINRY-UHFFFAOYSA-N 0.000 description 2
- YMZIFDLWYUSZCC-UHFFFAOYSA-N 2,6-dibromo-4-nitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1Br YMZIFDLWYUSZCC-UHFFFAOYSA-N 0.000 description 2
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 2
- RIYSFSQPHCAGLS-UHFFFAOYSA-N 2-amino-3,5-dinitrobenzonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O RIYSFSQPHCAGLS-UHFFFAOYSA-N 0.000 description 2
- XVYNBLCPQVDRCH-UHFFFAOYSA-N 2-amino-3-chloro-5-nitrobenzonitrile Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1C#N XVYNBLCPQVDRCH-UHFFFAOYSA-N 0.000 description 2
- QYRDWARBHMCOAG-UHFFFAOYSA-N 2-amino-5-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C=C1C#N QYRDWARBHMCOAG-UHFFFAOYSA-N 0.000 description 2
- ZBEGDHIBRPHOBV-UHFFFAOYSA-N 2-amino-5-nitrobenzene-1,3-dicarbonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1C#N ZBEGDHIBRPHOBV-UHFFFAOYSA-N 0.000 description 2
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 2
- 229940018167 2-amino-5-nitrothiazole Drugs 0.000 description 2
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 2
- KWMDHCLJYMVBNS-UHFFFAOYSA-N 2-bromo-4,6-dinitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KWMDHCLJYMVBNS-UHFFFAOYSA-N 0.000 description 2
- CGPPWNTVTNCHDO-UHFFFAOYSA-N 2-bromo-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Br CGPPWNTVTNCHDO-UHFFFAOYSA-N 0.000 description 2
- GLUCALKKMFBJEB-UHFFFAOYSA-N 2-bromo-6-chloro-4-nitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Br GLUCALKKMFBJEB-UHFFFAOYSA-N 0.000 description 2
- LHRIICYSGQGXSX-UHFFFAOYSA-N 2-chloro-4,6-dinitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1[N+]([O-])=O LHRIICYSGQGXSX-UHFFFAOYSA-N 0.000 description 2
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- VVDIMAMYKUTSCL-UHFFFAOYSA-N 5-amino-2-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C(C#N)=C1 VVDIMAMYKUTSCL-UHFFFAOYSA-N 0.000 description 2
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- PKUKCASRNJIQNU-UHFFFAOYSA-N 1-(2-amino-4-methyl-1,3-thiazol-5-yl)ethanone Chemical compound CC(=O)C=1SC(N)=NC=1C PKUKCASRNJIQNU-UHFFFAOYSA-N 0.000 description 1
- GPRYKVSEZCQIHD-UHFFFAOYSA-N 1-(4-aminophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1 GPRYKVSEZCQIHD-UHFFFAOYSA-N 0.000 description 1
- GOISDOCZKZYADO-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1=CC=CC=C1 GOISDOCZKZYADO-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 description 1
- JBXZCPXEYAEMJS-UHFFFAOYSA-N 2,5-dichloro-4-nitroaniline Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl JBXZCPXEYAEMJS-UHFFFAOYSA-N 0.000 description 1
- WAMNCBOYTXKHGN-UHFFFAOYSA-N 2,5-dimethoxy-4-phenyldiazenylaniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C=CC=CC=2)=C1OC WAMNCBOYTXKHGN-UHFFFAOYSA-N 0.000 description 1
- JBCUKQQIWSWEOK-UHFFFAOYSA-N 2-(benzenesulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 JBCUKQQIWSWEOK-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- GDFCZZHSWGWCHP-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-6-carbonitrile Chemical compound C1=C(C#N)C=C2SC(N)=NC2=C1 GDFCZZHSWGWCHP-UHFFFAOYSA-N 0.000 description 1
- DLXMVUGDZUUAIA-UHFFFAOYSA-N 2-amino-1-n,1-n,4-n,4-n-tetraethylbenzene-1,4-dicarboxamide Chemical compound CCN(CC)C(=O)C1=CC=C(C(=O)N(CC)CC)C(N)=C1 DLXMVUGDZUUAIA-UHFFFAOYSA-N 0.000 description 1
- MUHLVSZIVTURCZ-UHFFFAOYSA-N 2-amino-3-bromo-5-nitrobenzonitrile Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1C#N MUHLVSZIVTURCZ-UHFFFAOYSA-N 0.000 description 1
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 1
- JEQCDTSDGSTDID-UHFFFAOYSA-N 2-amino-n,n-dimethyl-5-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1N JEQCDTSDGSTDID-UHFFFAOYSA-N 0.000 description 1
- UVYPOPPLLZWKCD-UHFFFAOYSA-N 2-amino-n-butyl-5-nitrobenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1N UVYPOPPLLZWKCD-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- RKODNVITKISFKU-UHFFFAOYSA-N 2-bromo-5-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(Br)C(C#N)=C1 RKODNVITKISFKU-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- LNJDKXMHIWMTQJ-UHFFFAOYSA-N 2-methoxy-4-[(4-methoxyphenyl)diazenyl]-5-methylaniline Chemical compound C1=CC(OC)=CC=C1N=NC1=CC(OC)=C(N)C=C1C LNJDKXMHIWMTQJ-UHFFFAOYSA-N 0.000 description 1
- SZNYTNIULZADHD-UHFFFAOYSA-N 2-methoxy-5-methyl-4-phenyldiazenylaniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C=CC=CC=2)=C1C SZNYTNIULZADHD-UHFFFAOYSA-N 0.000 description 1
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
- KIMXIMWZIRTKCQ-UHFFFAOYSA-N 2-methylsulfonyl-4-nitroaniline Chemical compound CS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1N KIMXIMWZIRTKCQ-UHFFFAOYSA-N 0.000 description 1
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- IHGCCIAXAAWTSR-UHFFFAOYSA-N 3-amino-6-nitrophthalic acid Chemical compound NC1=CC=C([N+]([O-])=O)C(C(O)=O)=C1C(O)=O IHGCCIAXAAWTSR-UHFFFAOYSA-N 0.000 description 1
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 description 1
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 1
- FCXCNPRNYVYWIU-UHFFFAOYSA-N 3-chloro-4-[(3-chlorophenyl)diazenyl]aniline Chemical compound ClC1=CC(N)=CC=C1N=NC1=CC=CC(Cl)=C1 FCXCNPRNYVYWIU-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- GDYFDXDATVPPDR-UHFFFAOYSA-N 4-(benzenesulfonyl)aniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=CC=C1 GDYFDXDATVPPDR-UHFFFAOYSA-N 0.000 description 1
- QIKYZXDTTPVVAC-UHFFFAOYSA-N 4-Aminobenzamide Chemical compound NC(=O)C1=CC=C(N)C=C1 QIKYZXDTTPVVAC-UHFFFAOYSA-N 0.000 description 1
- YLNDNABNWASMFD-UHFFFAOYSA-N 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C YLNDNABNWASMFD-UHFFFAOYSA-N 0.000 description 1
- DBCJYQPYIOLAEU-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]-3-methylphenol Chemical compound OC1=CC(=C(C=C1)N=NC1=CC=C(C=C1)N)C DBCJYQPYIOLAEU-UHFFFAOYSA-N 0.000 description 1
- MXKIPKDHXYHKCJ-UHFFFAOYSA-N 4-[(4-chlorophenyl)diazenyl]-2,5-dimethoxyaniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C=CC(Cl)=CC=2)=C1OC MXKIPKDHXYHKCJ-UHFFFAOYSA-N 0.000 description 1
- RJEMRACHOZYVGV-UHFFFAOYSA-N 4-[(4-chlorophenyl)diazenyl]-2-methoxy-5-methylaniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C=CC(Cl)=CC=2)=C1C RJEMRACHOZYVGV-UHFFFAOYSA-N 0.000 description 1
- CJIOLSUKXRASPJ-UHFFFAOYSA-N 4-amino-2,6-dimethylbenzene-1,3-dicarbonitrile Chemical compound CC1=CC(N)=C(C#N)C(C)=C1C#N CJIOLSUKXRASPJ-UHFFFAOYSA-N 0.000 description 1
- QDNOBTKJPANVQD-UHFFFAOYSA-N 4-amino-2-chloro-5-nitrobenzonitrile Chemical compound NC1=CC(Cl)=C(C#N)C=C1[N+]([O-])=O QDNOBTKJPANVQD-UHFFFAOYSA-N 0.000 description 1
- OREVCMGFYSUYPX-UHFFFAOYSA-N 4-amino-3-chlorobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1Cl OREVCMGFYSUYPX-UHFFFAOYSA-N 0.000 description 1
- DWJRSEJMGZTDGY-UHFFFAOYSA-N 4-amino-7-nitro-1,2-benzothiazole-5-carbonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C2=C1C=NS2 DWJRSEJMGZTDGY-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- IPMNLGOBXWTQRV-UHFFFAOYSA-N 4-aminobenzene-1,3-dicarbonitrile Chemical compound NC1=CC=C(C#N)C=C1C#N IPMNLGOBXWTQRV-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- OXSANYRLJHSQEP-UHFFFAOYSA-N 4-aminophthalic acid Chemical compound NC1=CC=C(C(O)=O)C(C(O)=O)=C1 OXSANYRLJHSQEP-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 1
- NDWBXTNRCBNGAK-UHFFFAOYSA-N 4-methyl-5-nitro-1,3-thiazol-2-amine Chemical compound CC=1N=C(N)SC=1[N+]([O-])=O NDWBXTNRCBNGAK-UHFFFAOYSA-N 0.000 description 1
- XJEVFFNOMKXBLU-UHFFFAOYSA-N 4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C=C1 XJEVFFNOMKXBLU-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical class C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-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
- DGPPFUFNWWEMBL-UHFFFAOYSA-N 5-bromo-7-nitro-1,2-benzothiazol-4-amine Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C2=C1C=NS2 DGPPFUFNWWEMBL-UHFFFAOYSA-N 0.000 description 1
- FGZZEDHHSWZQGU-UHFFFAOYSA-N 5-chloro-7-nitro-1,2-benzothiazol-4-amine Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C2=C1C=NS2 FGZZEDHHSWZQGU-UHFFFAOYSA-N 0.000 description 1
- YKHFWFMWXBZUHK-UHFFFAOYSA-N 6,7-dichloro-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C(Cl)=C2SC(N)=NC2=C1 YKHFWFMWXBZUHK-UHFFFAOYSA-N 0.000 description 1
- ZYHNHJAMVNINSY-UHFFFAOYSA-N 6-methylsulfonyl-1,3-benzothiazol-2-amine Chemical compound CS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 ZYHNHJAMVNINSY-UHFFFAOYSA-N 0.000 description 1
- SOEMXHBNLXIWET-UHFFFAOYSA-N 7-chloro-5-nitro-2,1-benzothiazol-3-amine Chemical compound ClC1=CC([N+]([O-])=O)=CC2=C(N)SN=C21 SOEMXHBNLXIWET-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 241000343235 Maso Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N aniline-p-carboxylic acid Natural products NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- BDFDXMSSBFNAQG-UHFFFAOYSA-N diethyl 2-aminobenzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C(N)=C1 BDFDXMSSBFNAQG-UHFFFAOYSA-N 0.000 description 1
- DSSKDXUDARIMTR-UHFFFAOYSA-N dimethyl 2-aminobenzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(N)=C1 DSSKDXUDARIMTR-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- WZHUPCREDVWLKC-UHFFFAOYSA-N ethyl 2-amino-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N)=NC=1C WZHUPCREDVWLKC-UHFFFAOYSA-N 0.000 description 1
- AMLDNINFPSEDHZ-UHFFFAOYSA-N ethyl 2-amino-5-nitrobenzoate Chemical compound CCOC(=O)C1=CC([N+]([O-])=O)=CC=C1N AMLDNINFPSEDHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BLVZXLIGARVLJC-UHFFFAOYSA-N methyl 2-amino-3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1N BLVZXLIGARVLJC-UHFFFAOYSA-N 0.000 description 1
- VZDNXXPBYLGWOS-UHFFFAOYSA-N methyl 3-aminobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1 VZDNXXPBYLGWOS-UHFFFAOYSA-N 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 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
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000286 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
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000010023 transfer printing Methods 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
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 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
- C09B29/3639—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 amino groups
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
- C09B31/153—Heterocyclic components containing a six-membered ring with one nitrogen atom as the only ring hetero-atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Pyridine Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732309638 DE2309638A1 (de) | 1973-02-27 | 1973-02-27 | Dispersionsfarbstoffe der 2,6diaminopyridinreihe |
| DD17672074A DD110293A5 (enrdf_load_stackoverflow) | 1973-02-27 | 1974-02-20 | |
| CH257774A CH589122A5 (enrdf_load_stackoverflow) | 1973-02-27 | 1974-02-22 | |
| IT4878774A IT1003614B (it) | 1973-02-27 | 1974-02-26 | Coloranti da dispersione della serie 2 6 diamminopiridinica |
| JP2244574A JPS502025A (enrdf_load_stackoverflow) | 1973-02-27 | 1974-02-27 | |
| BE141448A BE811640A (fr) | 1973-02-27 | 1974-02-27 | Colorants disperses de la serie de la 2 |
| FR7406654A FR2219205A1 (en) | 1973-02-27 | 1974-02-27 | 2,6-Diaminopyridine disperse dyes - for dyeing polyesters, cellulose esters, polyacrylonitrile yellow-blue shades |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732309638 DE2309638A1 (de) | 1973-02-27 | 1973-02-27 | Dispersionsfarbstoffe der 2,6diaminopyridinreihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2309638A1 true DE2309638A1 (de) | 1974-09-12 |
Family
ID=5873182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732309638 Pending DE2309638A1 (de) | 1973-02-27 | 1973-02-27 | Dispersionsfarbstoffe der 2,6diaminopyridinreihe |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS502025A (enrdf_load_stackoverflow) |
| BE (1) | BE811640A (enrdf_load_stackoverflow) |
| CH (1) | CH589122A5 (enrdf_load_stackoverflow) |
| DD (1) | DD110293A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2309638A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2219205A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1003614B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2640576B2 (de) | 1975-10-29 | 1980-02-07 | Bayer Ag, 5090 Leverkusen | Verwendung von sulfonsäuregruppenfreien Azofarbstoffen zum Färben und Bedrucken von nicht tannierter Cellulose und nichttanniertem cellulosehaltigen! Textilmaterial |
| EP0042486A1 (de) * | 1980-06-06 | 1981-12-30 | BASF Aktiengesellschaft | Verfahren zum Färben von Belagmassen, organischen Lösungsmitteln und Mineralölprodukten und neue Farbstoffe |
| WO2018184770A1 (en) * | 2017-04-07 | 2018-10-11 | Huntsman Advanced Materials (Switzerland) Gmbh | Colorant mixtures |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5426357A (en) * | 1977-07-29 | 1979-02-27 | Ajinomoto Kk | Production of frozen ground fish meat containing soybean protein |
| JPS5498361A (en) * | 1978-01-21 | 1979-08-03 | Nishida Shigeru | Method for preventing actomyosin modification during freezing ground fish meat |
| DE3528759A1 (de) * | 1985-08-10 | 1987-02-19 | Basf Ag | Heterocyclische azofarbstoffe |
| JP2516097B2 (ja) * | 1990-10-16 | 1996-07-10 | 株式会社紀文 | 新規練製品及びその製造法 |
| JP6693785B2 (ja) * | 2016-03-30 | 2020-05-13 | オルガノフードテック株式会社 | 食品添加剤、および食品添加剤を含む食品 |
-
1973
- 1973-02-27 DE DE19732309638 patent/DE2309638A1/de active Pending
-
1974
- 1974-02-20 DD DD17672074A patent/DD110293A5/xx unknown
- 1974-02-22 CH CH257774A patent/CH589122A5/xx not_active IP Right Cessation
- 1974-02-26 IT IT4878774A patent/IT1003614B/it active
- 1974-02-27 JP JP2244574A patent/JPS502025A/ja active Pending
- 1974-02-27 FR FR7406654A patent/FR2219205A1/fr active Granted
- 1974-02-27 BE BE141448A patent/BE811640A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2640576B2 (de) | 1975-10-29 | 1980-02-07 | Bayer Ag, 5090 Leverkusen | Verwendung von sulfonsäuregruppenfreien Azofarbstoffen zum Färben und Bedrucken von nicht tannierter Cellulose und nichttanniertem cellulosehaltigen! Textilmaterial |
| EP0042486A1 (de) * | 1980-06-06 | 1981-12-30 | BASF Aktiengesellschaft | Verfahren zum Färben von Belagmassen, organischen Lösungsmitteln und Mineralölprodukten und neue Farbstoffe |
| WO2018184770A1 (en) * | 2017-04-07 | 2018-10-11 | Huntsman Advanced Materials (Switzerland) Gmbh | Colorant mixtures |
| US11407912B2 (en) | 2017-04-07 | 2022-08-09 | Huntsman International Llc | Colorant mixtures |
Also Published As
| Publication number | Publication date |
|---|---|
| BE811640A (fr) | 1974-08-27 |
| CH589122A5 (enrdf_load_stackoverflow) | 1977-06-30 |
| FR2219205A1 (en) | 1974-09-20 |
| IT1003614B (it) | 1976-06-10 |
| FR2219205B3 (enrdf_load_stackoverflow) | 1976-12-03 |
| JPS502025A (enrdf_load_stackoverflow) | 1975-01-10 |
| DD110293A5 (enrdf_load_stackoverflow) | 1974-12-12 |
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