JPH0322424B2 - - Google Patents
Info
- Publication number
- JPH0322424B2 JPH0322424B2 JP56119382A JP11938281A JPH0322424B2 JP H0322424 B2 JPH0322424 B2 JP H0322424B2 JP 56119382 A JP56119382 A JP 56119382A JP 11938281 A JP11938281 A JP 11938281A JP H0322424 B2 JPH0322424 B2 JP H0322424B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- residue
- methyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 34
- 229910052804 chromium Inorganic materials 0.000 claims description 7
- 239000011651 chromium Substances 0.000 claims description 7
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 5
- 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 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- WDEQGLDWZMIMJM-UHFFFAOYSA-N benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound OCC1CC(O)CN1C(=O)OCC1=CC=CC=C1 WDEQGLDWZMIMJM-UHFFFAOYSA-N 0.000 claims description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 3
- AOLYLEFSPFALGJ-UHFFFAOYSA-N copper formazan Chemical compound [Cu].NN=CN=N AOLYLEFSPFALGJ-UHFFFAOYSA-N 0.000 claims description 2
- SCDCQWMBJXIYNA-UHFFFAOYSA-N diazocopper Chemical group [N+](=[N-])=[Cu] SCDCQWMBJXIYNA-UHFFFAOYSA-N 0.000 claims description 2
- 239000001018 xanthene dye Substances 0.000 claims description 2
- -1 alkali metal salts Chemical class 0.000 description 151
- 150000001875 compounds Chemical class 0.000 description 126
- 125000000217 alkyl group Chemical group 0.000 description 86
- 239000000975 dye Substances 0.000 description 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 54
- 125000003545 alkoxy group Chemical group 0.000 description 50
- 238000005859 coupling reaction Methods 0.000 description 47
- 230000008878 coupling Effects 0.000 description 46
- 238000010168 coupling process Methods 0.000 description 46
- 238000004043 dyeing Methods 0.000 description 46
- 125000001424 substituent group Chemical group 0.000 description 38
- 238000000034 method Methods 0.000 description 36
- 239000000243 solution Substances 0.000 description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
- 229910052801 chlorine Inorganic materials 0.000 description 32
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 29
- 239000002657 fibrous material Substances 0.000 description 29
- 239000002253 acid Substances 0.000 description 28
- 125000001309 chloro group Chemical group Cl* 0.000 description 28
- 239000000835 fiber Substances 0.000 description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
- 239000000463 material Substances 0.000 description 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 21
- 125000000542 sulfonic acid group Chemical group 0.000 description 21
- 238000003756 stirring Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 18
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
- 229920003043 Cellulose fiber Polymers 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 17
- 239000003792 electrolyte Substances 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- 239000004952 Polyamide Substances 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 229920002647 polyamide Polymers 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 15
- 230000007935 neutral effect Effects 0.000 description 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 14
- 125000004093 cyano group Chemical group *C#N 0.000 description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 14
- 239000000985 reactive dye Substances 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 13
- 125000001624 naphthyl group Chemical group 0.000 description 13
- 239000001632 sodium acetate Substances 0.000 description 13
- 235000017281 sodium acetate Nutrition 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- 150000001555 benzenes Chemical class 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 150000002790 naphthalenes Chemical class 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 239000004753 textile Substances 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 9
- 239000000987 azo dye Substances 0.000 description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 125000001246 bromo group Chemical group Br* 0.000 description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 238000005185 salting out Methods 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 238000001694 spray drying Methods 0.000 description 8
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 229910001385 heavy metal Inorganic materials 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical group ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 150000004702 methyl esters Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000004957 naphthylene group Chemical group 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 4
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 4
- HGUYBLVGLMAUFF-UHFFFAOYSA-N 2-methoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=CC=C1N HGUYBLVGLMAUFF-UHFFFAOYSA-N 0.000 description 4
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 4
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
- LBTTZYSOZAGUDI-UHFFFAOYSA-N 4-(2-chloroethylsulfonylmethyl)benzoyl chloride Chemical compound ClCCS(=O)(=O)CC1=CC=C(C(Cl)=O)C=C1 LBTTZYSOZAGUDI-UHFFFAOYSA-N 0.000 description 4
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 4
- PTYVESRWZQGACO-UHFFFAOYSA-N 5-amino-2-methyl-3-(5-oxo-1H-pyrazol-2-yl)benzenesulfonic acid Chemical compound CC1=C(C=C(C=C1S(=O)(=O)O)N)N1NC(C=C1)=O PTYVESRWZQGACO-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 3
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 3
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 3
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 125000005236 alkanoylamino group Chemical group 0.000 description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012320 chlorinating reagent Substances 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Chemical group COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 235000019353 potassium silicate Nutrition 0.000 description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 2
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
- QGNJPFLIBOTDKU-UHFFFAOYSA-N 2,5-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C(S(O)(=O)=O)=C1 QGNJPFLIBOTDKU-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 2
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
- D06M13/272—Unsaturated compounds containing sulfur atoms
- D06M13/278—Vinylsulfonium compounds; Vinylsulfone or vinylsulfoxide compounds
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803029383 DE3029383A1 (de) | 1980-08-01 | 1980-08-01 | Wasserloesliche, faserreaktive verbindungen, ihre herstellung und verwendung sowie neue (beta) -chloraethylsulfonylmethyl-benzoesaeurehalogenide und deren verwendung als faserreaktive anker |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5757753A JPS5757753A (en) | 1982-04-07 |
| JPH0322424B2 true JPH0322424B2 (US07736425-20100615-C00009.png) | 1991-03-26 |
Family
ID=6108765
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56119382A Granted JPS5757753A (en) | 1980-08-01 | 1981-07-31 | Water-soluble fiber reactive compound and use for finishing spun matter and novel beta-chloroethylsulfonylmethyl-benzoyl halide and use as fiber reactive anchor |
| JP63187047A Granted JPS6456658A (en) | 1980-08-01 | 1988-07-28 | Novel beta-chloroethylsulfonylmethyl benzoyl- halide and use as fiber reactive anchor |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63187047A Granted JPS6456658A (en) | 1980-08-01 | 1988-07-28 | Novel beta-chloroethylsulfonylmethyl benzoyl- halide and use as fiber reactive anchor |
Country Status (7)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3718180A1 (de) * | 1987-05-29 | 1988-12-15 | Hoechst Ag | Wasserloesliche monoazo-naphtholcarbonsaeure-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| DE3724931A1 (de) * | 1987-07-28 | 1989-02-09 | Hoechst Ag | Wasserloesliche disazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| DE3829781A1 (de) * | 1988-09-02 | 1990-03-15 | Hoechst Ag | Wasserloesliche azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| US5166338A (en) * | 1989-03-01 | 1992-11-24 | Hoechst Aktiengesellschaft | Water-soluble fiber-reactive dyes and preparation and use thereof |
| US5439882A (en) * | 1989-12-29 | 1995-08-08 | Texas Tech University Health Sciences Center | Blood substitute |
| TW223098B (US07736425-20100615-C00009.png) * | 1991-10-24 | 1994-05-01 | Hoechst Ag | |
| DE4201611A1 (de) * | 1992-01-22 | 1993-07-29 | Bayer Ag | Reaktivfarbstoffe |
| DE59303537D1 (de) | 1992-05-04 | 1996-10-02 | Bayer Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| EP1670865A2 (en) * | 2003-08-19 | 2006-06-21 | Day-Glo Color Corp. | Polymeric colourants and method of colouring thermoplastic resins |
| JP5805416B2 (ja) * | 2011-03-29 | 2015-11-04 | オー・ジー長瀬カラーケミカル株式会社 | セルロース繊維用染料組成物、及びセルロース繊維を含む染色物を製造する方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4967918A (US07736425-20100615-C00009.png) * | 1972-09-08 | 1974-07-02 | ||
| JPS5070427A (US07736425-20100615-C00009.png) * | 1973-07-24 | 1975-06-11 | ||
| JPS5070426A (US07736425-20100615-C00009.png) * | 1973-07-24 | 1975-06-11 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118943A (en) * | 1959-12-08 | 1964-01-21 | Gen Aniline & Film Corp | Aminobenzylsulfonylethanol compounds |
| US3019266A (en) * | 1959-12-08 | 1962-01-30 | Gen Aniline & Film Corp | Nitrobenzylsulfonylethanol compounds |
| US3019268A (en) * | 1959-12-08 | 1962-01-30 | Gen Aniline & Film Corp | Nitrobenzylthioethanol compounds |
| US3094516A (en) * | 1959-12-30 | 1963-06-18 | Gen Aniline & Film Corp | Azo dyestuffs containing a benzene ring substituted by two hydroxyethylsul fonylmethyl groups |
| BE618604A (US07736425-20100615-C00009.png) * | 1960-06-24 | |||
| US3098096A (en) * | 1960-06-27 | 1963-07-16 | Crompton & Knowles Corp | 3-and 4-(2-chlorethylsulfonyl)-benzoyl chloride |
| GB1022756A (en) * | 1963-07-01 | 1966-03-16 | Crompton & Knowles Corp | Substituted benzoyl chlorides and textile auxiliaries prepared therefrom |
| US3261658A (en) * | 1960-06-27 | 1966-07-19 | Crompton & Knowles Corp | Process of reacting chloroethyl-sulfonyl benzoyl chloride compounds with textile auxiliaries and reacting said auxiliaries with textile fibers |
| US3169822A (en) * | 1961-11-20 | 1965-02-16 | Gen Aniline & Film Corp | Dyeing with dyes having ch2sch2ch2-halide groups |
| US3170912A (en) * | 1961-12-28 | 1965-02-23 | Gen Aniline & Film Corp | Azo dyestuffs containing a methylenesulfonylethanol radical or its sulfate ester |
| US3277075A (en) * | 1963-10-21 | 1966-10-04 | Gen Aniline & Film Corp | Dyestuffs containing hydroxyethyl-sulfonylmethyl groups |
| US3271435A (en) * | 1964-09-14 | 1966-09-06 | Gen Aniline & Film Corp | Bis[di(2-substituted ethyl) aminomethyl] benzene compounds |
| US4139527A (en) * | 1968-08-28 | 1979-02-13 | Hoechst Aktiengesellschaft | Fiber reactive monoazo dyestuffs containing a --SO2 --CH2 --CH2 --O--PO3 H2 group |
| GB1272802A (en) * | 1968-08-31 | 1972-05-03 | Hoechst Ag | New water-soluble reactive monoazo dyestuffs and processes for their manufacture |
-
1980
- 1980-08-01 DE DE19803029383 patent/DE3029383A1/de not_active Withdrawn
-
1981
- 1981-07-27 IN IN841/CAL/81A patent/IN156075B/en unknown
- 1981-07-30 DE DE8181105986T patent/DE3171019D1/de not_active Expired
- 1981-07-30 EP EP81105986A patent/EP0045488B1/de not_active Expired
- 1981-07-30 AR AR81286278A patent/AR243577A1/es active
- 1981-07-30 US US06/288,386 patent/US4473498A/en not_active Expired - Lifetime
- 1981-07-31 BR BR8104984A patent/BR8104984A/pt unknown
- 1981-07-31 JP JP56119382A patent/JPS5757753A/ja active Granted
-
1983
- 1983-01-31 US US06/462,340 patent/US4719053A/en not_active Expired - Lifetime
-
1984
- 1984-07-23 IN IN525/CAL/84A patent/IN162383B/en unknown
-
1988
- 1988-07-28 JP JP63187047A patent/JPS6456658A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4967918A (US07736425-20100615-C00009.png) * | 1972-09-08 | 1974-07-02 | ||
| JPS5070427A (US07736425-20100615-C00009.png) * | 1973-07-24 | 1975-06-11 | ||
| JPS5070426A (US07736425-20100615-C00009.png) * | 1973-07-24 | 1975-06-11 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3029383A1 (de) | 1982-03-18 |
| DE3171019D1 (en) | 1985-07-25 |
| JPS5757753A (en) | 1982-04-07 |
| US4473498A (en) | 1984-09-25 |
| US4719053A (en) | 1988-01-12 |
| JPH0360818B2 (US07736425-20100615-C00009.png) | 1991-09-17 |
| EP0045488A3 (en) | 1982-06-23 |
| JPS6456658A (en) | 1989-03-03 |
| EP0045488A2 (de) | 1982-02-10 |
| BR8104984A (pt) | 1982-04-20 |
| IN156075B (US07736425-20100615-C00009.png) | 1985-05-11 |
| IN162383B (US07736425-20100615-C00009.png) | 1988-05-21 |
| EP0045488B1 (de) | 1985-06-19 |
| AR243577A1 (es) | 1993-08-31 |
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