GB1561772A - Azo dye formulations for cellulose and cellulosic textile materials - Google Patents
Azo dye formulations for cellulose and cellulosic textile materials Download PDFInfo
- Publication number
- GB1561772A GB1561772A GB44801/76A GB4480176A GB1561772A GB 1561772 A GB1561772 A GB 1561772A GB 44801/76 A GB44801/76 A GB 44801/76A GB 4480176 A GB4480176 A GB 4480176A GB 1561772 A GB1561772 A GB 1561772A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- dye
- phenyl
- red
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims description 38
- 238000009472 formulation Methods 0.000 title claims description 23
- 239000001913 cellulose Substances 0.000 title claims description 11
- 229920002678 cellulose Polymers 0.000 title claims description 10
- 239000000463 material Substances 0.000 title claims description 7
- 239000004753 textile Substances 0.000 title claims description 7
- 239000000987 azo dye Substances 0.000 title description 2
- -1 CQ to C Chemical group 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 19
- 239000004744 fabric Substances 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 125000001246 bromo group Chemical group Br* 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 238000007639 printing Methods 0.000 claims description 5
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- WQFCFMPMUNOOTQ-UHFFFAOYSA-N 3-(2-phenoxyethoxy)propan-1-amine Chemical compound NCCCOCCOC1=CC=CC=C1 WQFCFMPMUNOOTQ-UHFFFAOYSA-N 0.000 claims description 2
- ONEOQRJTHAYVJL-UHFFFAOYSA-N 3-(2-phenylethoxy)propan-1-amine Chemical compound NCCCOCCC1=CC=CC=C1 ONEOQRJTHAYVJL-UHFFFAOYSA-N 0.000 claims description 2
- QFHLJYPKYWISHS-UHFFFAOYSA-N 3-phenylmethoxypropan-1-amine Chemical compound NCCCOCC1=CC=CC=C1 QFHLJYPKYWISHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 101150009274 nhr-1 gene Proteins 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims 2
- BECJFCCVDPUGRB-UHFFFAOYSA-N 2-aminoethyl n-phenylcarbamate Chemical compound NCCOC(=O)NC1=CC=CC=C1 BECJFCCVDPUGRB-UHFFFAOYSA-N 0.000 claims 1
- XJGVVOAKITWCAB-UHFFFAOYSA-N 2-phenylmethoxyethanamine Chemical compound NCCOCC1=CC=CC=C1 XJGVVOAKITWCAB-UHFFFAOYSA-N 0.000 claims 1
- YPTFCYIDUSOROW-UHFFFAOYSA-N 3-aminopropyl benzoate Chemical compound NCCCOC(=O)C1=CC=CC=C1 YPTFCYIDUSOROW-UHFFFAOYSA-N 0.000 claims 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims 1
- 229920003043 Cellulose fiber Polymers 0.000 claims 1
- 125000004802 cyanophenyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 239000012209 synthetic fiber Substances 0.000 claims 1
- 229920002994 synthetic fiber Polymers 0.000 claims 1
- 239000000975 dye Substances 0.000 description 31
- 230000008878 coupling Effects 0.000 description 23
- 238000010168 coupling process Methods 0.000 description 23
- 238000005859 coupling reaction Methods 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 229920000742 Cotton Polymers 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 11
- 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 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 229940072056 alginate Drugs 0.000 description 6
- 229920000615 alginic acid Polymers 0.000 description 6
- 235000010443 alginic acid Nutrition 0.000 description 6
- 239000010979 ruby Substances 0.000 description 6
- 229910001750 ruby Inorganic materials 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 230000008719 thickening Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 102100038239 Protein Churchill Human genes 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 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 4
- 238000003756 stirring Methods 0.000 description 4
- HUPIUXCRWNHLFL-UHFFFAOYSA-N 2-chloro-4-phenyldiazenylaniline Chemical compound C1=C(Cl)C(N)=CC=C1N=NC1=CC=CC=C1 HUPIUXCRWNHLFL-UHFFFAOYSA-N 0.000 description 3
- 206010016807 Fluid retention Diseases 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 2
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-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
- JBCUKQQIWSWEOK-UHFFFAOYSA-N 2-(benzenesulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 JBCUKQQIWSWEOK-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZDSAAIDZBOOOPJ-UHFFFAOYSA-N 4-methyl-2,6-bis[3-(2-phenoxyethoxy)propylamino]pyridine-3-carbonitrile Chemical compound N=1C(NCCCOCCOC=2C=CC=CC=2)=C(C#N)C(C)=CC=1NCCCOCCOC1=CC=CC=C1 ZDSAAIDZBOOOPJ-UHFFFAOYSA-N 0.000 description 2
- XLAPHZHNODDMDD-UHFFFAOYSA-N 4-methylpyridine-3-carbonitrile Chemical compound CC1=CC=NC=C1C#N XLAPHZHNODDMDD-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 238000010022 rotary screen printing Methods 0.000 description 2
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 2
- 229960005369 scarlet red Drugs 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- DYOOCGKIDCODHV-UHFFFAOYSA-N (2,4-dibromophenyl)cyanamide Chemical compound BrC1=CC=C(NC#N)C(Br)=C1 DYOOCGKIDCODHV-UHFFFAOYSA-N 0.000 description 1
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- PWZKESLISFPGHR-UHFFFAOYSA-N (2-chlorophenyl)cyanamide Chemical compound ClC1=CC=CC=C1NC#N PWZKESLISFPGHR-UHFFFAOYSA-N 0.000 description 1
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-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
- ZINRVIQBCHAZMM-UHFFFAOYSA-N 1-Amino-2,4-dibromoanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(Br)=C2N ZINRVIQBCHAZMM-UHFFFAOYSA-N 0.000 description 1
- MVRDXWVWKOUPDO-UHFFFAOYSA-N 1-amino-2-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Br)=C2N MVRDXWVWKOUPDO-UHFFFAOYSA-N 0.000 description 1
- QQOBTPNGSQEDAS-UHFFFAOYSA-N 1-amino-2-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Cl)=C2N QQOBTPNGSQEDAS-UHFFFAOYSA-N 0.000 description 1
- AWACQBFBMROGQC-UHFFFAOYSA-N 1-amino-4-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2N AWACQBFBMROGQC-UHFFFAOYSA-N 0.000 description 1
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 description 1
- KXOGXZAXERYOTC-UHFFFAOYSA-N 1-amino-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2OC KXOGXZAXERYOTC-UHFFFAOYSA-N 0.000 description 1
- GHUZWOWTEPWYHT-UHFFFAOYSA-N 1-aminobenzo[b]phenalen-7-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C3=C2C1=CC=C3N GHUZWOWTEPWYHT-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-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
- IRXRWZUCDXCJBD-UHFFFAOYSA-N 2,6-dibromo-4-phenyldiazenylaniline Chemical compound C1=C(Br)C(N)=C(Br)C=C1N=NC1=CC=CC=C1 IRXRWZUCDXCJBD-UHFFFAOYSA-N 0.000 description 1
- XIRRDAWDNHRRLB-UHFFFAOYSA-N 2,6-dibromoaniline Chemical compound NC1=C(Br)C=CC=C1Br XIRRDAWDNHRRLB-UHFFFAOYSA-N 0.000 description 1
- RLAQAHMABUCMSL-UHFFFAOYSA-N 2-(2-aminoethoxy)ethyl benzoate Chemical compound NCCOCCOC(=O)C1=CC=CC=C1 RLAQAHMABUCMSL-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-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
- ZDNLBGNACWKHAX-UHFFFAOYSA-N 2-amino-1,3-dibromoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Br)C(N)=C(Br)C=C3C(=O)C2=C1 ZDNLBGNACWKHAX-UHFFFAOYSA-N 0.000 description 1
- PLGPRGMWHYWEFT-UHFFFAOYSA-N 2-amino-1-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(N)=CC=C3C(=O)C2=C1 PLGPRGMWHYWEFT-UHFFFAOYSA-N 0.000 description 1
- CLWMYQQCXBSIBF-UHFFFAOYSA-N 2-amino-3-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(Br)=C2 CLWMYQQCXBSIBF-UHFFFAOYSA-N 0.000 description 1
- VMOJFUJVEWWUAV-UHFFFAOYSA-N 2-amino-3-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(Cl)=C2 VMOJFUJVEWWUAV-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- QYRDWARBHMCOAG-UHFFFAOYSA-N 2-amino-5-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C=C1C#N QYRDWARBHMCOAG-UHFFFAOYSA-N 0.000 description 1
- CTMTZUHSDGOWHP-UHFFFAOYSA-N 2-amino-6-(2-hydroxyethylcarbamoyl)benzoic acid Chemical compound NC1=CC=CC(C(O)=NCCO)=C1C(O)=O CTMTZUHSDGOWHP-UHFFFAOYSA-N 0.000 description 1
- WXKUDYUKWWQZGY-UHFFFAOYSA-N 2-amino-6-(phenylcarbamoyl)benzoic acid Chemical compound NC1=CC=CC(C(O)=NC=2C=CC=CC=2)=C1C(O)=O WXKUDYUKWWQZGY-UHFFFAOYSA-N 0.000 description 1
- QPVIKKACYIPURK-UHFFFAOYSA-N 2-amino-6-[(4-methylphenyl)carbamoyl]benzoic acid Chemical compound C1=CC(C)=CC=C1N=C(O)C1=CC=CC(N)=C1C(O)=O QPVIKKACYIPURK-UHFFFAOYSA-N 0.000 description 1
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 1
- JOTMFOWEVMXFHO-UHFFFAOYSA-N 2-aminoethyl benzoate Chemical compound NCCOC(=O)C1=CC=CC=C1 JOTMFOWEVMXFHO-UHFFFAOYSA-N 0.000 description 1
- JSBIDCNYNWHHRV-UHFFFAOYSA-N 2-methoxy-4-[(2-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C(=CC=CC=2)C)=C1 JSBIDCNYNWHHRV-UHFFFAOYSA-N 0.000 description 1
- BQDAFHDHPLPCLC-UHFFFAOYSA-N 2-methoxy-4-phenyldiazenylaniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C=CC=CC=2)=C1 BQDAFHDHPLPCLC-UHFFFAOYSA-N 0.000 description 1
- DAIFINJCZJVJSJ-UHFFFAOYSA-N 2-methoxyethyl 2-amino-3,5-dibromobenzoate Chemical compound COCCOC(=O)C1=CC(Br)=CC(Br)=C1N DAIFINJCZJVJSJ-UHFFFAOYSA-N 0.000 description 1
- PFRYFZZSECNQOL-UHFFFAOYSA-N 2-methyl-4-[(2-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C(=CC=CC=2)C)=C1 PFRYFZZSECNQOL-UHFFFAOYSA-N 0.000 description 1
- KQZBSZUGKSCFBL-UHFFFAOYSA-N 2-phenyldiazenylaniline Chemical class NC1=CC=CC=C1N=NC1=CC=CC=C1 KQZBSZUGKSCFBL-UHFFFAOYSA-N 0.000 description 1
- MPCQGSADMVSDHX-UHFFFAOYSA-N 3-(2-butoxyethoxy)propan-1-amine Chemical compound CCCCOCCOCCCN MPCQGSADMVSDHX-UHFFFAOYSA-N 0.000 description 1
- BBTNXKVTCYNELV-UHFFFAOYSA-N 3-[2-(2-phenoxyethoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOC1=CC=CC=C1 BBTNXKVTCYNELV-UHFFFAOYSA-N 0.000 description 1
- NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-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
- 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
- IVUQHXKKRQEFBU-UHFFFAOYSA-N 3-methyl-4-[(3-methylphenyl)diazenyl]aniline Chemical compound CC1=CC=CC(N=NC=2C(=CC(N)=CC=2)C)=C1 IVUQHXKKRQEFBU-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
- PLDAVAQNMVPUQC-UHFFFAOYSA-N 4-[(2-bromophenyl)diazenyl]aniline Chemical compound BrC1=C(C=CC=C1)N=NC1=CC=C(C=C1)N PLDAVAQNMVPUQC-UHFFFAOYSA-N 0.000 description 1
- URMDOARQQJLVFS-UHFFFAOYSA-N 4-[(2-methoxyphenyl)diazenyl]aniline Chemical compound COC1=CC=CC=C1N=NC1=CC=C(N)C=C1 URMDOARQQJLVFS-UHFFFAOYSA-N 0.000 description 1
- VDUXKWBSXPCZPG-UHFFFAOYSA-N 4-[(2-methylphenyl)diazenyl]aniline Chemical compound CC1=CC=CC=C1N=NC1=CC=C(N)C=C1 VDUXKWBSXPCZPG-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
- XXKRPQBEMXXEGW-UHFFFAOYSA-N 4-[(4-chlorophenyl)diazenyl]-2,5-dimethylaniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C=CC(Cl)=CC=2)=C1C XXKRPQBEMXXEGW-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
- RFPZFFIPFKMAIP-UHFFFAOYSA-N 4-amino-5-bromobenzene-1,3-dicarbonitrile Chemical compound NC1=C(Br)C=C(C#N)C=C1C#N RFPZFFIPFKMAIP-UHFFFAOYSA-N 0.000 description 1
- LTXJICHZZCYYAS-UHFFFAOYSA-N 4-amino-6-ethyl-1,3-dioxoisoindole-5-carbonitrile Chemical compound NC1=C(C#N)C(CC)=CC2=C1C(=O)NC2=O LTXJICHZZCYYAS-UHFFFAOYSA-N 0.000 description 1
- GMHTWQDRUGFBPX-UHFFFAOYSA-N 4-amino-6-methyl-1,3-dioxoisoindole-5-carbonitrile Chemical compound NC1=C(C#N)C(C)=CC2=C1C(=O)NC2=O GMHTWQDRUGFBPX-UHFFFAOYSA-N 0.000 description 1
- BRSAXHREENKEHX-UHFFFAOYSA-N 4-amino-7-chloroisoindole-1,3-dione Chemical compound NC1=CC=C(Cl)C2=C1C(=O)NC2=O BRSAXHREENKEHX-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
- GTCAZWRERBLCFJ-UHFFFAOYSA-N 4-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(N)=CC=C(C(O)=O)C2=C1 GTCAZWRERBLCFJ-UHFFFAOYSA-N 0.000 description 1
- WWZROQCSPTWTED-UHFFFAOYSA-N 4-nitro-1,2-benzothiazol-3-amine Chemical compound C1=CC([N+]([O-])=O)=C2C(N)=NSC2=C1 WWZROQCSPTWTED-UHFFFAOYSA-N 0.000 description 1
- VVDIMAMYKUTSCL-UHFFFAOYSA-N 5-amino-2-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C(C#N)=C1 VVDIMAMYKUTSCL-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
- WMDIAFBFWWIQQQ-UHFFFAOYSA-N 6-aminobenzo[a]phenalen-7-one Chemical compound C1=CC=C2C3=CC=CC=C3C(=O)C3=C2C1=CC=C3N WMDIAFBFWWIQQQ-UHFFFAOYSA-N 0.000 description 1
- IUTASKKTBSMTBV-UHFFFAOYSA-N CC1=C(C=CC(=C1)OC)N=NC1=CC=C(C(=C1)OC)N Chemical compound CC1=C(C=CC(=C1)OC)N=NC1=CC=C(C(=C1)OC)N IUTASKKTBSMTBV-UHFFFAOYSA-N 0.000 description 1
- 101800001195 Crustacean hyperglycemic hormone 3 Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- VNQABZCSYCTZMS-UHFFFAOYSA-N Orthoform Chemical compound COC(=O)C1=CC=C(O)C(N)=C1 VNQABZCSYCTZMS-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- MRQIXHXHHPWVIL-ISLYRVAYSA-N Sudan I Chemical compound OC1=CC=C2C=CC=CC2=C1\N=N\C1=CC=CC=C1 MRQIXHXHHPWVIL-ISLYRVAYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000005333 aroyloxy group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 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
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- WNVWWDKUMKBZQV-UHFFFAOYSA-N bis(4-methylphenyl)diazene Chemical compound C1=CC(C)=CC=C1N=NC1=CC=C(C)C=C1 WNVWWDKUMKBZQV-UHFFFAOYSA-N 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 1
- SUXCALIDMIIJCK-UHFFFAOYSA-L disodium;4-amino-3-[[4-[4-[(1-amino-4-sulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=C4C=CC=CC4=C(C=3)S([O-])(=O)=O)N)C)=CC(S([O-])(=O)=O)=C21 SUXCALIDMIIJCK-UHFFFAOYSA-L 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- KUWAAZMPJBFLEO-UHFFFAOYSA-N n,n,2-trichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1Cl KUWAAZMPJBFLEO-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-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
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229950006098 orthocaine Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- HJCRYHUIBTZWFZ-UHFFFAOYSA-N propyl 2-amino-3,5-dichlorobenzoate Chemical compound CCCOC(=O)C1=CC(Cl)=CC(Cl)=C1N HJCRYHUIBTZWFZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010020 roller printing Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- AZLXCBPKSXFMET-UHFFFAOYSA-M sodium 4-[(4-sulfophenyl)diazenyl]naphthalen-1-olate Chemical compound [Na+].C12=CC=CC=C2C(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 AZLXCBPKSXFMET-UHFFFAOYSA-M 0.000 description 1
- MLVYOYVMOZFHIU-UHFFFAOYSA-M sodium;4-[(4-anilinophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 MLVYOYVMOZFHIU-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000001043 yellow dye Substances 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
-
- 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
- C09B29/0018—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0822375A AT373930B (de) | 1975-10-29 | 1975-10-29 | Farbstoffzubereitungen fuer das faerben und bedrucken von cellulose und cellulosehaltigem textilmaterial |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561772A true GB1561772A (en) | 1980-03-05 |
Family
ID=3603610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB44801/76A Expired GB1561772A (en) | 1975-10-29 | 1976-10-28 | Azo dye formulations for cellulose and cellulosic textile materials |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4146535A (enExample) |
| JP (1) | JPS6015756B2 (enExample) |
| AT (1) | AT373930B (enExample) |
| CH (1) | CH609722A5 (enExample) |
| DE (1) | DE2640576C3 (enExample) |
| FR (1) | FR2329724A1 (enExample) |
| GB (1) | GB1561772A (enExample) |
| IT (1) | IT1080516B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005024123A3 (en) * | 2003-09-08 | 2005-06-02 | Ciba Sc Holding Ag | Process for printing or dyeing cellulose/polyester mixed fibres |
| WO2017202480A1 (en) * | 2016-05-25 | 2017-11-30 | Huntsman Advanced Materials (Switzerland) Gmbh | Disperse azo dyes, a process for the preparation thereof and the use thereof |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2755022A1 (de) * | 1977-12-09 | 1979-08-30 | Bayer Ag | Azofarbstoffe |
| DE2832020C2 (de) | 1978-07-21 | 1982-12-23 | Basf Ag, 6700 Ludwigshafen | Disazofarbstoffe mit Pyridinkupplungskomponenten, deren Herstellung und Verwendung |
| DE2903132A1 (de) * | 1979-01-27 | 1980-07-31 | Bayer Ag | Verfahren zum faerben und bedrucken von cellulosefasern |
| DE2930919A1 (de) * | 1979-07-30 | 1981-02-26 | Basf Ag | Verfahren zum faerben und bedrucken von cellulosehaltigem textilmaterial |
| DE3201268A1 (de) * | 1982-01-16 | 1983-07-28 | Basf Ag, 6700 Ludwigshafen | Benzisothiazolazofarbstoffe |
| DE3330155A1 (de) * | 1983-08-20 | 1985-03-07 | Basf Ag, 6700 Ludwigshafen | Isothiazolazofarbstoffe |
| CA2379372A1 (en) * | 1999-07-14 | 2001-01-18 | Tommy G. Taylor | Innovative incineration system for refuse-derived fuels, coal and petroleum coke, or chlorinated hydrocarbons |
| JP4205948B2 (ja) * | 2001-01-26 | 2009-01-07 | チバ ホールディング インコーポレーテッド | アゾ染料、それらの製造方法、ならびに着色プラスチックまたはカラーポリマー粒子の製造および疎水性繊維材料の浸染または捺染におけるそれらの使用 |
| ATE499414T1 (de) * | 2001-01-26 | 2011-03-15 | Huntsman Adv Mat Switzerland | Azofarbstoffe, verfahren zu ihrer herstellung sowie ihre verwendung zum faerben oder bedrucken von hydrophobem fasermaterial |
| MXPA04012033A (es) * | 2002-06-03 | 2005-03-07 | Ciba Sc Holding Ag | Tintes azo de antraquinona. |
| JP5897032B2 (ja) * | 2010-12-20 | 2016-03-30 | ハンツマン アドバンスト マテリアルズ （スイッツァランド） ゲーエムベーハーＨｕｎｔｓｍａｎ Ａｄｖａｎｃｅｄ Ｍａｔｅｒｉａｌｓ （Ｓｗｉｔｚｅｒｌａｎｄ） Ｇｍｂｈ | 分散アゾ染料 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH1785468A4 (enExample) | 1968-11-25 | 1976-09-15 | ||
| DE2263458A1 (de) | 1972-12-27 | 1974-07-04 | Basf Ag | 2,6-diaminopyridin-farbstoffe |
| DE2260827C3 (de) * | 1972-12-13 | 1980-11-13 | Basf Ag, 6700 Ludwigshafen | 2,6-Diaminopyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Kupplungskomponenten für Azofarbstoffe |
| DE2211663C3 (de) | 1972-03-10 | 1975-01-16 | Basf Ag, 6700 Ludwigshafen | Azofarbstoffe mit 2,6-Diaminopyrfdinen als Kupplungskomponenten, Verfahren zu deren Herstellung und Farbstoffzubereitungen |
| DE2251702B2 (de) * | 1972-10-21 | 1976-11-18 | Basf Ag, 6700 Ludwigshafen | Dispersionsazofarbstoffe der 2,6- diaminopyridinreihe, verfahren zu deren herstellung und ihre verwendung |
| DE2258823A1 (de) | 1972-12-01 | 1974-06-06 | Basf Ag | 2,6-diaminopyridinfarbstoffe |
| DE2259684A1 (de) | 1972-12-06 | 1974-06-12 | Basf Ag | Azofarbstoffe mit 2,6-diaminopyridinen als kupplungskomponenten |
| DE2062717C3 (de) | 1970-12-19 | 1975-02-13 | Basf Ag | Azofarbstoffe aus 2,6-Diaminopyridin-derivaten, Verfahren zu deren Herstellung und Verwendung |
| DE2156545A1 (de) | 1971-11-15 | 1973-05-24 | Basf Ag | Azofarbstoffe aus 2,6-diamino-pyridinderivaten |
| DE2226933C3 (de) | 1972-06-02 | 1975-05-07 | Basf Ag, 6700 Ludwigshafen | Azofarbstoffe mit 2,6 Diaminopyridinen als Kupplungskomponenten, Verfahren zu deren Herstellung und ihre Verwendung |
| US3998802A (en) * | 1970-12-19 | 1976-12-21 | Basf Aktiengesellschaft | Azo dye with a 3-cyano- or 3-carbamoyl-4-methyl-2,6-diamino-pyridine coupling component |
| DE2251719A1 (de) | 1972-10-21 | 1974-04-25 | Basf Ag 6700 Ludwigshafen | Dispersionsfarbstoffe der 2,6diaminopyridinreihe |
| CH596263A5 (enExample) * | 1972-03-10 | 1978-03-15 | Basf Ag | |
| DE2222099A1 (de) | 1972-05-05 | 1973-11-22 | Hoechst Ag | Basische azofarbstoffe, ihre herstellung und verwendung |
| DE2222873A1 (de) * | 1972-05-10 | 1973-11-22 | Basf Ag | Verfahren zum faerben von synthetischen linearen polyestern |
| DE2309638A1 (de) | 1973-02-27 | 1974-09-12 | Basf Ag | Dispersionsfarbstoffe der 2,6diaminopyridinreihe |
| DE2404854A1 (de) | 1974-02-01 | 1975-08-21 | Basf Ag | Farbstoffzubereitungen fuer den transferdruck |
| US3974123A (en) * | 1974-03-01 | 1976-08-10 | Basf Aktiengesellschaft | Dyes for thermoplastics |
| DE2512365A1 (de) | 1975-03-21 | 1976-09-30 | Cassella Farbwerke Mainkur Ag | Wasserunloesliche monoazofarbstoffe und verfahren zu ihrer herstellung |
| DE2513949A1 (de) | 1975-03-29 | 1976-10-07 | Bayer Ag | Azofarbstoffe |
-
1975
- 1975-10-29 AT AT0822375A patent/AT373930B/de not_active IP Right Cessation
-
1976
- 1976-09-09 DE DE2640576A patent/DE2640576C3/de not_active Expired
- 1976-10-01 US US05/728,527 patent/US4146535A/en not_active Expired - Lifetime
- 1976-10-18 FR FR7631221A patent/FR2329724A1/fr active Granted
- 1976-10-26 CH CH1349776A patent/CH609722A5/xx not_active IP Right Cessation
- 1976-10-27 IT IT51916/76A patent/IT1080516B/it active
- 1976-10-28 JP JP51128907A patent/JPS6015756B2/ja not_active Expired
- 1976-10-28 GB GB44801/76A patent/GB1561772A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005024123A3 (en) * | 2003-09-08 | 2005-06-02 | Ciba Sc Holding Ag | Process for printing or dyeing cellulose/polyester mixed fibres |
| WO2017202480A1 (en) * | 2016-05-25 | 2017-11-30 | Huntsman Advanced Materials (Switzerland) Gmbh | Disperse azo dyes, a process for the preparation thereof and the use thereof |
| TWI707002B (zh) * | 2016-05-25 | 2020-10-11 | 瑞士商杭斯曼高級材料公司 | 分散偶氮染料、其製備方法及其用途 |
| US10934435B2 (en) | 2016-05-25 | 2021-03-02 | Huntsman International Llc | Disperse azo dyes, a process for the preparation thereof and the use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US4146535A (en) | 1979-03-27 |
| CH609722A5 (enExample) | 1979-03-15 |
| IT1080516B (it) | 1985-05-16 |
| AT373930B (de) | 1984-03-12 |
| FR2329724A1 (fr) | 1977-05-27 |
| JPS6015756B2 (ja) | 1985-04-22 |
| FR2329724B1 (enExample) | 1981-02-13 |
| ATA822375A (de) | 1983-07-15 |
| DE2640576C3 (de) | 1980-10-23 |
| DE2640576B2 (de) | 1980-02-07 |
| DE2640576A1 (de) | 1977-05-12 |
| JPS5259789A (en) | 1977-05-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |