DE2114158A1 - Reaktivfarbstoffe - Google Patents
ReaktivfarbstoffeInfo
- Publication number
- DE2114158A1 DE2114158A1 DE19712114158 DE2114158A DE2114158A1 DE 2114158 A1 DE2114158 A1 DE 2114158A1 DE 19712114158 DE19712114158 DE 19712114158 DE 2114158 A DE2114158 A DE 2114158A DE 2114158 A1 DE2114158 A1 DE 2114158A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- dyes
- alkylene
- pyrimidine
- difluoro
- 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
- 239000000985 reactive dye Substances 0.000 title claims description 10
- 239000000975 dye Substances 0.000 claims description 223
- -1 aromatic-heterocyclic radicals Chemical class 0.000 claims description 111
- 238000005859 coupling reaction Methods 0.000 claims description 67
- 230000008878 coupling Effects 0.000 claims description 66
- 238000010168 coupling process Methods 0.000 claims description 65
- 238000004043 dyeing Methods 0.000 claims description 57
- 238000009833 condensation Methods 0.000 claims description 56
- 230000005494 condensation Effects 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 55
- 239000000460 chlorine Substances 0.000 claims description 37
- GOYNRDSJTYLXBU-UHFFFAOYSA-N 5-chloro-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Cl)C(F)=N1 GOYNRDSJTYLXBU-UHFFFAOYSA-N 0.000 claims description 35
- 230000008569 process Effects 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 27
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 150000003254 radicals Chemical class 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 150000004056 anthraquinones Chemical class 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
- 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 16
- 239000000463 material Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 239000000987 azo dye Substances 0.000 claims description 12
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 12
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 239000001000 anthraquinone dye Substances 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 238000006193 diazotization reaction Methods 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 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 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 239000001007 phthalocyanine dye Substances 0.000 claims description 5
- NTSYSQNAPGMSIH-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine Chemical compound FC1=CC(F)=NC(F)=N1 NTSYSQNAPGMSIH-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002790 naphthalenes Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 claims description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 3
- KZMWBUVUQLGBBP-UHFFFAOYSA-N 2,4,5,6-tetrafluoropyrimidine Chemical compound FC1=NC(F)=C(F)C(F)=N1 KZMWBUVUQLGBBP-UHFFFAOYSA-N 0.000 claims description 3
- YXYCPKOAGWDZKX-UHFFFAOYSA-N 2,4-difluoro-5-(trifluoromethyl)pyrimidine Chemical compound FC1=NC=C(C(F)(F)F)C(F)=N1 YXYCPKOAGWDZKX-UHFFFAOYSA-N 0.000 claims description 3
- BAIJUHNFHQYGHR-UHFFFAOYSA-N 4,5-dichloro-2,6-difluoropyrimidine Chemical compound FC1=NC(F)=C(Cl)C(Cl)=N1 BAIJUHNFHQYGHR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- BIMGULMREAFXSC-UHFFFAOYSA-N 2,4,5-trifluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1F BIMGULMREAFXSC-UHFFFAOYSA-N 0.000 claims description 2
- MLLSXQLOUGEEGV-UHFFFAOYSA-N 2,4,6-trifluoro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=C(F)N=C(F)N=C1F MLLSXQLOUGEEGV-UHFFFAOYSA-N 0.000 claims description 2
- JOYWMWSTASJQHZ-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine-5-carbonitrile Chemical compound FC1=NC(F)=C(C#N)C(F)=N1 JOYWMWSTASJQHZ-UHFFFAOYSA-N 0.000 claims description 2
- YKLOPWRWWFKUBX-UHFFFAOYSA-N 2,4-difluoro-6-methylpyrimidine Chemical compound CC1=CC(F)=NC(F)=N1 YKLOPWRWWFKUBX-UHFFFAOYSA-N 0.000 claims description 2
- JZSYSXZDIQUOGP-UHFFFAOYSA-N 2,4-difluoropyrimidine Chemical compound FC1=CC=NC(F)=N1 JZSYSXZDIQUOGP-UHFFFAOYSA-N 0.000 claims description 2
- SLCUSSPKUGKMGA-UHFFFAOYSA-N 4-bromo-2,6-difluoropyrimidine Chemical compound FC1=CC(Br)=NC(F)=N1 SLCUSSPKUGKMGA-UHFFFAOYSA-N 0.000 claims description 2
- XZSZSTCLQANXKU-UHFFFAOYSA-N 5-chloro-2,4-difluoropyrimidine Chemical compound FC1=NC=C(Cl)C(F)=N1 XZSZSTCLQANXKU-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 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 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 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 claims 1
- LUOWQRCVEYJUJS-UHFFFAOYSA-N 2,4,6-trifluoro-5-(trifluoromethyl)pyrimidine Chemical compound FC1=NC(F)=C(C(F)(F)F)C(F)=N1 LUOWQRCVEYJUJS-UHFFFAOYSA-N 0.000 claims 1
- NIAMELKDNLLWRH-UHFFFAOYSA-N 2,4-difluoro-5-methylpyrimidine Chemical compound CC1=CN=C(F)N=C1F NIAMELKDNLLWRH-UHFFFAOYSA-N 0.000 claims 1
- FKSSZHRRUUZKCM-UHFFFAOYSA-N 2,4-difluoro-6-(trifluoromethyl)pyrimidine Chemical compound FC1=CC(C(F)(F)F)=NC(F)=N1 FKSSZHRRUUZKCM-UHFFFAOYSA-N 0.000 claims 1
- VJMKIDUNVPFBOB-UHFFFAOYSA-N 4-chloro-2,6-difluoro-5-methylpyrimidine Chemical compound CC1=C(F)N=C(F)N=C1Cl VJMKIDUNVPFBOB-UHFFFAOYSA-N 0.000 claims 1
- WOQIMJVYLVUMGO-UHFFFAOYSA-N 4-chloro-2,6-difluoro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=C(F)N=C(F)N=C1Cl WOQIMJVYLVUMGO-UHFFFAOYSA-N 0.000 claims 1
- FRSCGYMSBBDAKE-UHFFFAOYSA-N 5-(chloromethyl)-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(CCl)C(F)=N1 FRSCGYMSBBDAKE-UHFFFAOYSA-N 0.000 claims 1
- BOLIYMRNXVAWIJ-UHFFFAOYSA-N 5-bromo-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Br)C(F)=N1 BOLIYMRNXVAWIJ-UHFFFAOYSA-N 0.000 claims 1
- UPACQRCORIQBTF-UHFFFAOYSA-N 5-bromo-2,4-difluoropyrimidine Chemical compound FC1=NC=C(Br)C(F)=N1 UPACQRCORIQBTF-UHFFFAOYSA-N 0.000 claims 1
- LTRDQYKIIGULAQ-UHFFFAOYSA-N 5-chloro-2,4-difluoro-6-(trifluoromethyl)pyrimidine Chemical compound FC1=NC(F)=C(Cl)C(C(F)(F)F)=N1 LTRDQYKIIGULAQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 238000005670 sulfation reaction Methods 0.000 claims 1
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 227
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 163
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 135
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 119
- 235000002639 sodium chloride Nutrition 0.000 description 82
- 239000011780 sodium chloride Substances 0.000 description 78
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 61
- 235000011121 sodium hydroxide Nutrition 0.000 description 45
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 45
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 41
- 239000000203 mixture Substances 0.000 description 36
- 239000004202 carbamide Substances 0.000 description 35
- 210000002268 wool Anatomy 0.000 description 31
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 30
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 28
- 239000000725 suspension Substances 0.000 description 28
- 229920003043 Cellulose fiber Polymers 0.000 description 25
- 235000010288 sodium nitrite Nutrition 0.000 description 22
- 239000012954 diazonium Substances 0.000 description 21
- 150000001989 diazonium salts Chemical class 0.000 description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000003756 stirring Methods 0.000 description 19
- 238000001035 drying Methods 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 239000004744 fabric Substances 0.000 description 16
- 239000012065 filter cake Substances 0.000 description 15
- 229920000742 Cotton Polymers 0.000 description 14
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 14
- 239000001103 potassium chloride Substances 0.000 description 13
- 235000011164 potassium chloride Nutrition 0.000 description 13
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 11
- 229940012017 ethylenediamine Drugs 0.000 description 11
- 239000002609 medium Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000006386 neutralization reaction Methods 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 7
- 229920002678 cellulose Polymers 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- 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 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000004382 potting Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-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
- 239000004952 Polyamide Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229940072056 alginate Drugs 0.000 description 3
- 235000010443 alginic acid Nutrition 0.000 description 3
- 229920000615 alginic acid Polymers 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 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
- 239000003086 colorant Substances 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- HWKWYDXHMQQDQJ-UHFFFAOYSA-N 2,3-dibromopropanoyl chloride Chemical compound ClC(=O)C(Br)CBr HWKWYDXHMQQDQJ-UHFFFAOYSA-N 0.000 description 2
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- ACYSJALOFWHUEX-UHFFFAOYSA-N 4-chloro-2,6-difluoropyrimidine Chemical compound FC1=CC(Cl)=NC(F)=N1 ACYSJALOFWHUEX-UHFFFAOYSA-N 0.000 description 1
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- NDHIIWMVAUTCNX-UHFFFAOYSA-N 4-chloro-2-methylsulfonylpyrimidine-5-sulfonic acid Chemical compound CS(=O)(=O)C1=NC=C(S(O)(=O)=O)C(Cl)=N1 NDHIIWMVAUTCNX-UHFFFAOYSA-N 0.000 description 1
- AFRRXNLSPAQVRI-UHFFFAOYSA-N 4-chloro-6-methyl-2-sulfonyl-1h-pyrimidine Chemical compound CC1=CC(Cl)=NC(=S(=O)=O)N1 AFRRXNLSPAQVRI-UHFFFAOYSA-N 0.000 description 1
- UYCCTQPHCSKTTN-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfonyl)pyrimidine Chemical compound CC1=CC(S(C)(=O)=O)=NC(S(C)(=O)=O)=N1 UYCCTQPHCSKTTN-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
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- OPLXQBDWWSSPEX-UHFFFAOYSA-N 5-bromo-4-methyl-2,6-bis(methylsulfonyl)pyrimidine Chemical compound CC1=NC(S(C)(=O)=O)=NC(S(C)(=O)=O)=C1Br OPLXQBDWWSSPEX-UHFFFAOYSA-N 0.000 description 1
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- XQAFHGXXHIZSGZ-UHFFFAOYSA-N 8-hydroxynaphthalene-1,6-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 XQAFHGXXHIZSGZ-UHFFFAOYSA-N 0.000 description 1
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- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
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- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
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- HXAVIUPZFMDULP-UHFFFAOYSA-N O=S(C(Cl)Cl)(C1=CC(S(C(Cl)Cl)(=O)=O)=NC2=CC=CC=C12)=O Chemical compound O=S(C(Cl)Cl)(C1=CC(S(C(Cl)Cl)(=O)=O)=NC2=CC=CC=C12)=O HXAVIUPZFMDULP-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
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- 206010039587 Scarlet Fever Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
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- 239000007997 Tricine buffer Substances 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 1
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
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- SOYBJIUDKRLQTA-UHFFFAOYSA-N benzene;dinaphthalen-1-yldiazene Chemical class C1=CC=CC=C1.C1=CC=C2C(N=NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 SOYBJIUDKRLQTA-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KQDDQXNVESLJNO-UHFFFAOYSA-N chloromethanesulfonyl chloride Chemical compound ClCS(Cl)(=O)=O KQDDQXNVESLJNO-UHFFFAOYSA-N 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 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
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- WSEFXLKPOBQART-UHFFFAOYSA-N dinaphthalen-1-yldiazene;naphthalene Chemical class C1=CC=CC2=CC=CC=C21.C1=CC=C2C(N=NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 WSEFXLKPOBQART-UHFFFAOYSA-N 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
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- 238000009963 fulling Methods 0.000 description 1
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- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical compound [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- 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 description 1
- USPGWRYCHDAJCB-UHFFFAOYSA-N methyl 2,4-difluoropyrimidine-5-carboxylate Chemical compound COC(=O)C1=CN=C(F)N=C1F USPGWRYCHDAJCB-UHFFFAOYSA-N 0.000 description 1
- YSEQKGHEMQCJCC-UHFFFAOYSA-N methyl 2,6-difluoropyrimidine-4-carboxylate Chemical compound COC(=O)C1=CC(F)=NC(F)=N1 YSEQKGHEMQCJCC-UHFFFAOYSA-N 0.000 description 1
- SQYUJKVKVFILNB-UHFFFAOYSA-N methyl 2-amino-4-[(2,5-dichlorophenyl)carbamoyl]benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(=O)NC1=CC(Cl)=CC=C1Cl SQYUJKVKVFILNB-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712114158 DE2114158A1 (de) | 1971-03-24 | 1971-03-24 | Reaktivfarbstoffe |
| DD161692A DD102158A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-24 | 1972-03-21 | |
| IT7222296A IT953554B (it) | 1971-03-24 | 1972-03-22 | Coloranti reattivi |
| CH1558473A CH565226A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-24 | 1972-03-22 | |
| GB1366172A GB1363374A (en) | 1971-03-24 | 1972-03-23 | Reactive dyestuffs |
| JP2859272A JPS5434007B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-24 | 1972-03-23 | |
| NL7203905A NL7203905A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-24 | 1972-03-23 | |
| US05/237,920 US4065446A (en) | 1971-03-24 | 1972-03-24 | Reactive dyestuffs containing urea alkylene linkage between chromophore and reactive radical |
| FR7210432A FR2130673B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-24 | 1972-03-24 | |
| BE781214A BE781214A (fr) | 1971-03-24 | 1972-03-24 | Colorants reactifs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712114158 DE2114158A1 (de) | 1971-03-24 | 1971-03-24 | Reaktivfarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2114158A1 true DE2114158A1 (de) | 1972-09-28 |
Family
ID=5802553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712114158 Pending DE2114158A1 (de) | 1971-03-24 | 1971-03-24 | Reaktivfarbstoffe |
Country Status (10)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2549570A1 (de) * | 1975-11-05 | 1977-05-12 | Bayer Ag | Azoreaktivfarbstoffe |
| DE2734679A1 (de) * | 1976-08-02 | 1978-02-09 | Ciba Geigy Ag | Faserreaktive azofarbstoffe, deren herstellung und verwendung |
| DE2906191A1 (de) * | 1979-02-17 | 1980-08-28 | Bayer Ag | Azoreaktivfarbstoffe |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2831912A1 (de) * | 1978-07-20 | 1980-02-07 | Bayer Ag | Azoreaktivfarbstoffe |
| DE3340590A1 (de) * | 1983-11-10 | 1985-05-23 | Bayer Ag, 5090 Leverkusen | Polyazoreaktivfarbstoffe |
| EP0174909B1 (de) * | 1984-08-30 | 1991-10-16 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| GB8517779D0 (en) * | 1985-07-15 | 1985-08-21 | Ici Plc | Anthraquinone derivatives |
| TW204339B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1990-05-17 | 1993-04-21 | Ciba Geigy Ag | |
| DE4122866A1 (de) * | 1991-07-11 | 1993-01-14 | Bayer Ag | Monoreaktive mono- und disazoreaktivfarbstoffe |
| DE4125754A1 (de) * | 1991-08-03 | 1993-02-04 | Bayer Ag | Fluorpyrimidin-reaktivfarbstoffe |
| ES2254731T3 (es) * | 2001-10-08 | 2006-06-16 | Clariant Finance (Bvi) Limited | Pigmetos triazo reactivos a la fibra. |
| KR101493717B1 (ko) | 2010-03-04 | 2015-02-16 | 아지노모토 가부시키가이샤 | 알킬아민 유도체 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH410238A (de) * | 1957-11-29 | 1966-03-31 | Sandoz Ag | Verfahren zur Herstellung von Reaktivfarbstoffen |
| CH364854A (de) * | 1957-11-29 | 1962-10-15 | Sandoz Ag | Verfahren zur Herstellung von Pyrimidinfarbstoffen |
| CH420414A (de) * | 1959-04-29 | 1966-09-15 | Sandoz Ag | Verfahren zur Herstellung von Pyrimidinfarbstoffen |
| CH405537A (de) * | 1957-11-29 | 1966-01-15 | Sandoz Ag | Verfahren zur Herstellung von Reaktivfarbstoffen |
| CH420424A (de) * | 1960-09-08 | 1966-09-15 | Sandoz Ag | Verfahren zur Herstellung von Reaktivfarbstoffen |
| FR1277461A (fr) * | 1960-11-21 | 1961-12-01 | Ici Ltd | Nouvelles matières colorantes solubles dans l'eau |
| CH424032A (de) * | 1962-02-23 | 1966-11-15 | Sandoz Ag | Verfahren zur Herstellung von Reaktivfarbstoffen |
| DE1252824B (de) * | 1963-03-01 | 1967-10-26 | J. R. Geigy A.G., Basel (Schweiz) | Verfahren zur Herstellung von reaktiven Farbstoffen |
| BE645855A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-05-09 | 1964-07-16 | ||
| DE1644171A1 (de) * | 1966-09-10 | 1970-07-30 | Bayer Ag | Reaktivfarbstoffe und Verfahren zu deren Herstellung |
| US3632611A (en) * | 1967-10-09 | 1972-01-04 | Sumitomo Chemical Co | Anthraquinone dyes containing a reactive carbamylmethyl group |
-
1971
- 1971-03-24 DE DE19712114158 patent/DE2114158A1/de active Pending
-
1972
- 1972-03-21 DD DD161692A patent/DD102158A5/xx unknown
- 1972-03-22 IT IT7222296A patent/IT953554B/it active
- 1972-03-22 CH CH1558473A patent/CH565226A5/xx not_active IP Right Cessation
- 1972-03-23 GB GB1366172A patent/GB1363374A/en not_active Expired
- 1972-03-23 JP JP2859272A patent/JPS5434007B1/ja active Pending
- 1972-03-23 NL NL7203905A patent/NL7203905A/xx unknown
- 1972-03-24 US US05/237,920 patent/US4065446A/en not_active Expired - Lifetime
- 1972-03-24 FR FR7210432A patent/FR2130673B1/fr not_active Expired
- 1972-03-24 BE BE781214A patent/BE781214A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2549570A1 (de) * | 1975-11-05 | 1977-05-12 | Bayer Ag | Azoreaktivfarbstoffe |
| DE2549570C2 (de) * | 1975-11-05 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | Azo-Reaktivfarbstoffe |
| DE2734679A1 (de) * | 1976-08-02 | 1978-02-09 | Ciba Geigy Ag | Faserreaktive azofarbstoffe, deren herstellung und verwendung |
| DE2906191A1 (de) * | 1979-02-17 | 1980-08-28 | Bayer Ag | Azoreaktivfarbstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7203905A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-26 |
| FR2130673A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-11-03 |
| US4065446A (en) | 1977-12-27 |
| IT953554B (it) | 1973-08-10 |
| BE781214A (fr) | 1972-09-25 |
| DD102158A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-12-05 |
| GB1363374A (en) | 1974-08-14 |
| FR2130673B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-24 |
| JPS5434007B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-10-24 |
| CH565226A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-08-15 |
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Legal Events
| Date | Code | Title | Description |
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| OHN | Withdrawal |