SE192650C1 - - Google Patents
Info
- Publication number
- SE192650C1 SE192650C1 SE192650DA SE192650C1 SE 192650 C1 SE192650 C1 SE 192650C1 SE 192650D A SE192650D A SE 192650DA SE 192650 C1 SE192650 C1 SE 192650C1
- Authority
- SE
- Sweden
- Prior art keywords
- anthraquinone
- catalyst
- sec
- sulfonic acid
- dye
- Prior art date
Links
- 239000000975 dye Substances 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- QDPOHAYYMHVFMI-UHFFFAOYSA-N boron;hydrate Chemical class [B].O QDPOHAYYMHVFMI-UHFFFAOYSA-N 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 150000002484 inorganic compounds Chemical class 0.000 claims 1
- 229910010272 inorganic material Inorganic materials 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 86
- 239000000725 suspension Substances 0.000 description 67
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 56
- 239000000243 solution Substances 0.000 description 52
- 239000004744 fabric Substances 0.000 description 37
- -1 Anthraquinone-1-sulphonic acid potassium 1-nitro-anthraquinone-8 -sulfonic acid potassium Chemical compound 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000010949 copper Substances 0.000 description 21
- JVUYWILPYBCNNG-UHFFFAOYSA-N potassium;oxido(oxo)borane Chemical compound [K+].[O-]B=O JVUYWILPYBCNNG-UHFFFAOYSA-N 0.000 description 19
- XUINISXRACTVNW-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 XUINISXRACTVNW-UHFFFAOYSA-N 0.000 description 14
- 235000019239 indanthrene blue RS Nutrition 0.000 description 14
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 14
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 13
- 229910052802 copper Inorganic materials 0.000 description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 11
- 229940012189 methyl orange Drugs 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- 229960001922 sodium perborate Drugs 0.000 description 8
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 8
- 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 7
- 239000002253 acid Substances 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 7
- 229960002449 glycine Drugs 0.000 description 7
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000008149 soap solution Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 229940079877 pyrogallol Drugs 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 4
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- BHZXDYRJZYTGQA-UHFFFAOYSA-N anthracene-1,2,9,10-tetrone Chemical compound C1=CC(=O)C(=O)C2=C1C(=O)C1=CC=CC=C1C2=O BHZXDYRJZYTGQA-UHFFFAOYSA-N 0.000 description 3
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 3
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- JGUQDUKBUKFFRO-GGWOSOGESA-N (NE)-N-[(3E)-3-hydroxyiminobutan-2-ylidene]hydroxylamine Chemical compound O\N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-GGWOSOGESA-N 0.000 description 2
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 2
- DWBYKKOMRNYEMS-UHFFFAOYSA-N 1,5-diamino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=C(N)C(S(O)(=O)=O)=CC=C2C(=O)C2=C1C=CC=C2N DWBYKKOMRNYEMS-UHFFFAOYSA-N 0.000 description 2
- JEPVBIMOJDNAAK-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid;sodium Chemical compound [Na].O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(S(O)(=O)=O)=C2N JEPVBIMOJDNAAK-UHFFFAOYSA-N 0.000 description 2
- MMKNBFSDCOALQO-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(O)=O)=C2N MMKNBFSDCOALQO-UHFFFAOYSA-N 0.000 description 2
- PZSHANOBYYVNEX-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(S(O)(=O)=O)=C2N PZSHANOBYYVNEX-UHFFFAOYSA-N 0.000 description 2
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SSONOLLEQNJAFC-UHFFFAOYSA-N 3-amino-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(C(O)=O)=C2 SSONOLLEQNJAFC-UHFFFAOYSA-N 0.000 description 2
- QQPQYWGNVMIGAF-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-dicarboxylic acid Chemical compound C1=CC=C2C(=O)C3=C(C(O)=O)C(C(=O)O)=CC=C3C(=O)C2=C1 QQPQYWGNVMIGAF-UHFFFAOYSA-N 0.000 description 2
- ASDLSKCKYGVMAI-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 241000408659 Darpa Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CBPBONMHNWNVFI-UHFFFAOYSA-N [K].O=C1C=2C(S(=O)(=O)O)=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O Chemical compound [K].O=C1C=2C(S(=O)(=O)O)=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O CBPBONMHNWNVFI-UHFFFAOYSA-N 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 210000000941 bile Anatomy 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JXUKQCUPTNLTCS-UHFFFAOYSA-N vat green 1 Chemical compound C1=CC=C[C]2C(=O)C(C3=C45)=CC=C4C(C4=C67)=CC=C7C(=O)[C]7C=CC=CC7=C6C=C(OC)C4=C5C(OC)=CC3=C21 JXUKQCUPTNLTCS-UHFFFAOYSA-N 0.000 description 2
- DURBTILWOVXSNP-UHFFFAOYSA-N 1,3,4-trihydroxy-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(S(O)(=O)=O)C(O)=C2O DURBTILWOVXSNP-UHFFFAOYSA-N 0.000 description 1
- NNAUDJVNWLIGDT-UHFFFAOYSA-N 1,3,5,7-tetrahydroxyanthracene-9,10-dione Chemical compound OC1=CC(O)=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 NNAUDJVNWLIGDT-UHFFFAOYSA-N 0.000 description 1
- MKARJQUHEFPSDM-UHFFFAOYSA-N 1,4,5-triaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C=CC=C2N MKARJQUHEFPSDM-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- BYONTSBHKAJYCU-UHFFFAOYSA-N 1,4-diamino-9,10-dioxoanthracene-2,6-disulfonic acid Chemical compound O=C1C2=CC=C(S(O)(=O)=O)C=C2C(=O)C2=C1C(N)=C(S(O)(=O)=O)C=C2N BYONTSBHKAJYCU-UHFFFAOYSA-N 0.000 description 1
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- LTQANAVAMUQQEA-UHFFFAOYSA-N 1,4-dihydroxy-9,10-dioxoanthracene-2,6-disulfonic acid Chemical compound O=C1C2=CC=C(S(O)(=O)=O)C=C2C(=O)C2=C1C(O)=C(S(O)(=O)=O)C=C2O LTQANAVAMUQQEA-UHFFFAOYSA-N 0.000 description 1
- WWWSDHATHLGGRD-UHFFFAOYSA-N 1,5-dichloro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound ClC1=C(C=CC=2C(C3=C(C=CC=C3C(C12)=O)Cl)=O)C(=O)O WWWSDHATHLGGRD-UHFFFAOYSA-N 0.000 description 1
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 1
- XBGXIWFUHLXTTR-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxo-2h-anthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)(S(O)(=O)=O)CC=C2Br XBGXIWFUHLXTTR-UHFFFAOYSA-N 0.000 description 1
- GSHAIJZSVNSADP-UHFFFAOYSA-N 1-amino-5-chloro-2-methylanthracene-9,10-dione Chemical compound NC1=C(C=CC=2C(C3=C(C=CC=C3C(C12)=O)Cl)=O)C GSHAIJZSVNSADP-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- OZFDRTGKARBHQM-UHFFFAOYSA-N 1-iodoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2I OZFDRTGKARBHQM-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- HXDZGPAXAIRSAB-UHFFFAOYSA-N 3,4-diamino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(N)C(S(O)(=O)=O)=C2 HXDZGPAXAIRSAB-UHFFFAOYSA-N 0.000 description 1
- NVNLUZUQLPMRKT-UHFFFAOYSA-N 3-amino-4-bromo-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=C(N)C(C(O)=O)=C2 NVNLUZUQLPMRKT-UHFFFAOYSA-N 0.000 description 1
- RIGCOIRFSVUFIZ-UHFFFAOYSA-N 3-amino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(S(O)(=O)=O)=C2 RIGCOIRFSVUFIZ-UHFFFAOYSA-N 0.000 description 1
- MQSFCEJHJKTYBZ-UHFFFAOYSA-N 4-amino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S(O)(=O)=O)C=C2N MQSFCEJHJKTYBZ-UHFFFAOYSA-N 0.000 description 1
- HYKDWGUFDOYDGV-UHFFFAOYSA-N 4-anilinobenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NC1=CC=CC=C1 HYKDWGUFDOYDGV-UHFFFAOYSA-N 0.000 description 1
- WVWSLCJRULYUMP-UHFFFAOYSA-N 5,8-diamino-6,7-dichloro-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C=2C(N)=C(Cl)C(Cl)=C(N)C=2C(=O)C2=C1C=CC=C2S(O)(=O)=O WVWSLCJRULYUMP-UHFFFAOYSA-N 0.000 description 1
- CAOPOEWNJFGVEK-UHFFFAOYSA-N 5-nitro-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC(S(=O)(=O)O)=CC=C2C(=O)C2=C1C=CC=C2[N+]([O-])=O CAOPOEWNJFGVEK-UHFFFAOYSA-N 0.000 description 1
- UEZJOQCWOFDUOR-UHFFFAOYSA-N 8-amino-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC(S(O)(=O)=O)=C2C(=O)C2=C1C=CC=C2N UEZJOQCWOFDUOR-UHFFFAOYSA-N 0.000 description 1
- UGRPYHKFFFMXCA-UHFFFAOYSA-N 8-amino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=C(S(O)(=O)=O)C=C2C(=O)C2=C1C=CC=C2N UGRPYHKFFFMXCA-UHFFFAOYSA-N 0.000 description 1
- CZZFIABCNJUYFY-UHFFFAOYSA-N 8-chloro-5-nitro-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C(C(=CC=C2Cl)[N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O CZZFIABCNJUYFY-UHFFFAOYSA-N 0.000 description 1
- LXLIFNPZHSMYTR-UHFFFAOYSA-N 8-nitro-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 LXLIFNPZHSMYTR-UHFFFAOYSA-N 0.000 description 1
- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 1
- ODJXGZPKDAAQIH-UHFFFAOYSA-N 9,10-dioxoanthracene-1,4-dicarboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(C(O)=O)=CC=C2C(=O)O ODJXGZPKDAAQIH-UHFFFAOYSA-N 0.000 description 1
- NPJWMYCZWPHPIC-UHFFFAOYSA-N 9,10-dioxoanthracene-1,5-dicarboxylic acid Chemical compound O=C1C2=C(C(O)=O)C=CC=C2C(=O)C2=C1C=CC=C2C(=O)O NPJWMYCZWPHPIC-UHFFFAOYSA-N 0.000 description 1
- YKHSDQDRVMUJGA-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid;potassium Chemical compound [K].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O YKHSDQDRVMUJGA-UHFFFAOYSA-N 0.000 description 1
- MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000009355 Antron Species 0.000 description 1
- OBKSOOYIKLUNMD-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NC1=CC=CC=2C(C=3C(=CC=CC3C(C12)=O)S(=O)(=O)O)=O Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC=CC=2C(C=3C(=CC=CC3C(C12)=O)S(=O)(=O)O)=O OBKSOOYIKLUNMD-UHFFFAOYSA-N 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- ZYHBRBAMLZPYSX-UHFFFAOYSA-N ClC1=C(C=CC=2C(C3=C(C(=CC=C3C(C12)=O)C(=O)O)Cl)=O)C(=O)O Chemical compound ClC1=C(C=CC=2C(C3=C(C(=CC=C3C(C12)=O)C(=O)O)Cl)=O)C(=O)O ZYHBRBAMLZPYSX-UHFFFAOYSA-N 0.000 description 1
- NINNEYLDNSNNRB-UHFFFAOYSA-N ClC1=C(C=CC=2C(C3=CC=CC(=C3C(C12)=O)Cl)=O)C(=O)O Chemical compound ClC1=C(C=CC=2C(C3=CC=CC(=C3C(C12)=O)Cl)=O)C(=O)O NINNEYLDNSNNRB-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000002917 Fraxinus ornus Nutrition 0.000 description 1
- 244000182067 Fraxinus ornus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 241001233242 Lontra Species 0.000 description 1
- ANEBGPVJNNVMQW-UHFFFAOYSA-N NC(C(C(C(C1=C(C(S(O)(=O)=O)=C2)N)=C2Br)=O)=C(C(Br)=C2)C1=O)=C2S(O)(=O)=O Chemical compound NC(C(C(C(C1=C(C(S(O)(=O)=O)=C2)N)=C2Br)=O)=C(C(Br)=C2)C1=O)=C2S(O)(=O)=O ANEBGPVJNNVMQW-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- IBVLAPQFOXQSRN-UHFFFAOYSA-N OC1=C(C=CC=2C(C3=CC=CC(=C3C(C12)=O)S(=O)(=O)O)=O)O Chemical compound OC1=C(C=CC=2C(C3=CC=CC(=C3C(C12)=O)S(=O)(=O)O)=O)O IBVLAPQFOXQSRN-UHFFFAOYSA-N 0.000 description 1
- JEXOSPIWWPWMSE-UHFFFAOYSA-N OC1=C(NC2=C(C=CC=3C(C4=CC=CC=C4C(C23)=O)=O)NC2=C(C=CC=C2)O)C=CC=C1 Chemical compound OC1=C(NC2=C(C=CC=3C(C4=CC=CC=C4C(C23)=O)=O)NC2=C(C=CC=C2)O)C=CC=C1 JEXOSPIWWPWMSE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001302210 Sida <water flea> Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 244000274883 Urtica dioica Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 0.000 description 1
- QONNSKOHDHVXDE-UHFFFAOYSA-N [Na].O=C1C2=CC=CC(S(O)(=O)=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O Chemical compound [Na].O=C1C2=CC=CC(S(O)(=O)=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O QONNSKOHDHVXDE-UHFFFAOYSA-N 0.000 description 1
- WJEIYVAPNMUNIU-UHFFFAOYSA-N [Na].OC(O)=O Chemical compound [Na].OC(O)=O WJEIYVAPNMUNIU-UHFFFAOYSA-N 0.000 description 1
- XZLHVAFSPKKNRZ-UHFFFAOYSA-N [Na].OS(=O)(=O)c1ccc2C(=O)c3c(cccc3[N+]([O-])=O)C(=O)c2c1 Chemical compound [Na].OS(=O)(=O)c1ccc2C(=O)c3c(cccc3[N+]([O-])=O)C(=O)c2c1 XZLHVAFSPKKNRZ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- WNHUAWNEKMITEW-UHFFFAOYSA-N anthrapurpurin Chemical compound C1=C(O)C(O)=C2C(=O)C3=CC(O)=CC=C3C(=O)C2=C1 WNHUAWNEKMITEW-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- ZDRJMZMVJTUQHH-UHFFFAOYSA-N borane;potassium Chemical compound B.[K] ZDRJMZMVJTUQHH-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- TVMUHOAONWHJBV-UHFFFAOYSA-N dehydroglycine Chemical compound OC(=O)C=N TVMUHOAONWHJBV-UHFFFAOYSA-N 0.000 description 1
- PXFORDPOPVGNJL-UHFFFAOYSA-N diphenylsulfamic acid Chemical compound C=1C=CC=CC=1N(S(=O)(=O)O)C1=CC=CC=C1 PXFORDPOPVGNJL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- VBHKTXLEJZIDJF-UHFFFAOYSA-N quinalizarin Chemical compound C1=CC(O)=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1O VBHKTXLEJZIDJF-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- KJPJZBYFYBYKPK-UHFFFAOYSA-N vat yellow 1 Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3N=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1N=C4C=C5 KJPJZBYFYBYKPK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE192650T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE192650C1 true SE192650C1 (ref) | 1964-01-01 |
Family
ID=41978891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE192650D SE192650C1 (ref) |
Country Status (1)
| Country | Link |
|---|---|
| SE (1) | SE192650C1 (ref) |
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0
- SE SE192650D patent/SE192650C1/sv unknown
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