BE367618A - - Google Patents

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Publication number

BE367618A

BE367618A BE367618DA BE367618A BE 367618 A BE367618 A BE 367618A BE 367618D A BE367618D A BE 367618DA BE 367618 A BE367618 A BE 367618A

Authority

BE

Belgium

Prior art keywords

sep

parts

ether

acid

ethers

Prior art date

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• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 94
• 239000000975 dye Substances 0.000 claims description 49
• LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 36
• 238000000034 method Methods 0.000 claims description 31
• 230000001808 coupling Effects 0.000 claims description 29
• 238000010168 coupling process Methods 0.000 claims description 28
• 238000005859 coupling reaction Methods 0.000 claims description 28
• 150000002170 ethers Chemical class 0.000 claims description 24
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
• 235000010288 sodium nitrite Nutrition 0.000 claims description 18
• 239000000835 fiber Substances 0.000 claims description 15
• 239000000987 azo dye Substances 0.000 claims description 14
• 239000000463 material Substances 0.000 claims description 14
• 229920000742 Cotton Polymers 0.000 claims description 13
• 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 13
• 238000004043 dyeing Methods 0.000 claims description 13
• 150000001412 amines Chemical class 0.000 claims description 12
• -1 anthraquinones naphtho quinones Chemical class 0.000 claims description 12
• 150000001875 compounds Chemical class 0.000 claims description 12
• 239000000126 substance Substances 0.000 claims description 12
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
• 238000004040 coloring Methods 0.000 claims description 10
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 10
• 238000007639 printing Methods 0.000 claims description 10
• 230000015572 biosynthetic process Effects 0.000 claims description 9
• 239000000470 constituent Substances 0.000 claims description 9
• 150000002989 phenols Chemical class 0.000 claims description 9
• 230000002378 acidificating Effects 0.000 claims description 8
• 125000003277 amino group Chemical group 0.000 claims description 8
• 238000006193 diazotization reaction Methods 0.000 claims description 8
• 125000001033 ether group Chemical group 0.000 claims description 8
• 241001062009 Indigofera Species 0.000 claims description 7
• 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 7
• 230000003647 oxidation Effects 0.000 claims description 7
• 238000007254 oxidation reaction Methods 0.000 claims description 7
• 238000007747 plating Methods 0.000 claims description 7
• 210000002268 Wool Anatomy 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 238000003786 synthesis reaction Methods 0.000 claims description 5
• 230000002194 synthesizing Effects 0.000 claims description 5
• SBOJXQVPLKSXOG-UHFFFAOYSA-N O-amino-Hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims description 4
• 238000006460 hydrolysis reaction Methods 0.000 claims description 4
• 230000001264 neutralization Effects 0.000 claims description 4
• 150000004053 quinones Chemical class 0.000 claims description 4
• 206010062080 Pigmentation disease Diseases 0.000 claims description 3
• 150000004056 anthraquinones Chemical class 0.000 claims description 3
• 125000000468 ketone group Chemical group 0.000 claims description 3
• 230000019612 pigmentation Effects 0.000 claims description 3
• 239000002994 raw material Substances 0.000 claims description 3
• 229920002955 Art silk Polymers 0.000 claims description 2
• 238000005470 impregnation Methods 0.000 claims description 2
• 229920003086 cellulose ether Polymers 0.000 claims 1
• KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
• 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 113
• 239000000243 solution Substances 0.000 description 54
• VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
• 239000002253 acid Substances 0.000 description 34
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
• 239000000203 mixture Substances 0.000 description 17
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 238000003756 stirring Methods 0.000 description 14
• VFNGKCDDZUSWLR-UHFFFAOYSA-N Disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 13
• 239000011780 sodium chloride Substances 0.000 description 13
• 235000002639 sodium chloride Nutrition 0.000 description 13
• 150000003839 salts Chemical class 0.000 description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
• 239000004744 fabric Substances 0.000 description 11
• 239000007800 oxidant agent Substances 0.000 description 9
• 159000000000 sodium salts Chemical class 0.000 description 9
• RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 6
• 239000001187 sodium carbonate Substances 0.000 description 6
• 229910000029 sodium carbonate Inorganic materials 0.000 description 6
• ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 5
• 238000010411 cooking Methods 0.000 description 5
• 159000000001 potassium salts Chemical class 0.000 description 5
• VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
• 239000001632 sodium acetate Substances 0.000 description 5
• 235000017281 sodium acetate Nutrition 0.000 description 5
• 235000011121 sodium hydroxide Nutrition 0.000 description 5
• GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
• 229920001615 Tragacanth Polymers 0.000 description 4
• 238000005755 formation reaction Methods 0.000 description 4
• 229920000591 gum Polymers 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• 150000003931 anilides Chemical class 0.000 description 3
• 239000000305 astragalus gummifer gum Substances 0.000 description 3
• 229950011260 betanaphthol Drugs 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• 230000027326 copulation Effects 0.000 description 3
• 230000000875 corresponding Effects 0.000 description 3
• 238000002360 preparation method Methods 0.000 description 3
• CXYMDAXGGAITQP-UHFFFAOYSA-N 2-hydroxy-N-phenylnaphthalene-1-carboxamide Chemical compound OC1=CC=C2C=CC=CC2=C1C(=O)NC1=CC=CC=C1 CXYMDAXGGAITQP-UHFFFAOYSA-N 0.000 description 2
• HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 2
• SOIFLUNRINLCBN-UHFFFAOYSA-N Ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
• UXJVWJGDHIZPLD-UHFFFAOYSA-O Ammonium vanadate Chemical compound [NH4+].O=[V-](=O)=O UXJVWJGDHIZPLD-UHFFFAOYSA-O 0.000 description 2
• RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• YZHUMGUJCQRKBT-UHFFFAOYSA-M Sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 2
• AKEJUJNQAAGONA-UHFFFAOYSA-N Sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
• ZUJURJDZOPMJPH-UHFFFAOYSA-M [Cl-].[N-]=[N+]=C1CC=CC=C1 Chemical compound [Cl-].[N-]=[N+]=C1CC=CC=C1 ZUJURJDZOPMJPH-UHFFFAOYSA-M 0.000 description 2
• 239000003929 acidic solution Substances 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
• 238000010586 diagram Methods 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
• 230000035929 gnawing Effects 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 239000001044 red dye Substances 0.000 description 2
• 229940080281 sodium chlorate Drugs 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
• YTMCUIACOKRXQA-UHFFFAOYSA-N (2-aminoacetyl) 2-aminoacetate Chemical compound NCC(=O)OC(=O)CN YTMCUIACOKRXQA-UHFFFAOYSA-N 0.000 description 1
• LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-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
• QLSWIGRIBOSFMV-UHFFFAOYSA-N 1H-pyrrol-2-amine Chemical compound NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 description 1
• VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
• JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
• CXOWHCCVISNMIX-UHFFFAOYSA-N 2-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(N)=CC=C21 CXOWHCCVISNMIX-UHFFFAOYSA-N 0.000 description 1
• PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
• TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
• BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
• 229920002301 Cellulose acetate Polymers 0.000 description 1
• ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 240000006669 Helianthus annuus Species 0.000 description 1
• 235000003222 Helianthus annuus Nutrition 0.000 description 1
• 229940097275 Indigo Drugs 0.000 description 1
• WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
• PSRNXESQSJEQMN-UHFFFAOYSA-N N-(4-chloro-2-methylphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound CC1=CC(Cl)=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O PSRNXESQSJEQMN-UHFFFAOYSA-N 0.000 description 1
• 229920000297 Rayon Polymers 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
• 235000011130 ammonium sulphate Nutrition 0.000 description 1
• 229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 description 1
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 150000008049 diazo compounds Chemical class 0.000 description 1
• 150000001989 diazonium salts Chemical class 0.000 description 1
• 238000005562 fading Methods 0.000 description 1
• 150000002334 glycols Chemical class 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 239000010446 mirabilite Substances 0.000 description 1
• 150000004780 naphthols Chemical class 0.000 description 1
• 150000002791 naphthoquinones Chemical class 0.000 description 1
• 150000005002 naphthylamines Chemical class 0.000 description 1
• TWXTWZIUMCFMSG-UHFFFAOYSA-N nitride(3-) Chemical compound [N-3] TWXTWZIUMCFMSG-UHFFFAOYSA-N 0.000 description 1
• IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
• IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
• 239000001048 orange dye Substances 0.000 description 1
• 230000001590 oxidative Effects 0.000 description 1
• 239000000049 pigment Substances 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 239000001047 purple dye Substances 0.000 description 1
• JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000000344 soap Substances 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
• AJXVJQAPXVDFBT-UHFFFAOYSA-M sodium;naphthalen-2-olate Chemical compound [Na+].C1=CC=CC2=CC([O-])=CC=C21 AJXVJQAPXVDFBT-UHFFFAOYSA-M 0.000 description 1
• 210000001519 tissues Anatomy 0.000 description 1
• 150000004992 toluidines Chemical class 0.000 description 1
• 239000000984 vat dye Substances 0.000 description 1