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
• 238000000034 method Methods 0.000 claims description 40
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 36
• 230000008569 process Effects 0.000 claims description 31
• 230000008878 coupling Effects 0.000 claims description 29
• 238000010168 coupling process Methods 0.000 claims description 29
• 238000005859 coupling reaction Methods 0.000 claims description 29
• 150000002170 ethers Chemical class 0.000 claims description 24
• 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
• PCFMUWBCZZUMRX-UHFFFAOYSA-N 9,10-Dihydroxyanthracene Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=C(O)C2=C1 PCFMUWBCZZUMRX-UHFFFAOYSA-N 0.000 claims description 12
• 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 effect 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
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 210000002268 wool Anatomy 0.000 claims description 6
• 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 5
• 150000004056 anthraquinones Chemical class 0.000 claims description 5
• 238000003786 synthesis reaction Methods 0.000 claims description 5
• 229930192627 Naphthoquinone Natural products 0.000 claims description 4
• 230000007062 hydrolysis Effects 0.000 claims description 4
• 238000006460 hydrolysis reaction Methods 0.000 claims description 4
• 230000007935 neutral effect Effects 0.000 claims description 4
• SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims description 4
• 150000004053 quinones Chemical class 0.000 claims description 4
• 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
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
• 229920003086 cellulose ether Polymers 0.000 claims 1
• 239000000243 solution Substances 0.000 description 52
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
• 239000002253 acid Substances 0.000 description 34
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 239000000203 mixture Substances 0.000 description 14
• 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
• 235000002639 sodium chloride Nutrition 0.000 description 13
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
• 150000003839 salts Chemical class 0.000 description 12
• 230000009471 action Effects 0.000 description 11
• 239000004744 fabric Substances 0.000 description 11
• 239000007800 oxidant agent Substances 0.000 description 9
• 159000000000 sodium salts Chemical class 0.000 description 9
• JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 6
• 229910021578 Iron(III) chloride Inorganic materials 0.000 description 6
• RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 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
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
• 238000010411 cooking Methods 0.000 description 5
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-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
• 230000008719 thickening Effects 0.000 description 5
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
• 229920001615 Tragacanth Polymers 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
• GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-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
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• 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 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
• 239000013078 crystal Substances 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
• BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 2
• ZUJURJDZOPMJPH-UHFFFAOYSA-N 5-diazocyclohexa-1,3-diene;hydrochloride Chemical compound Cl.[N-]=[N+]=C1CC=CC=C1 ZUJURJDZOPMJPH-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
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-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
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• 239000003929 acidic solution Substances 0.000 description 2
• 239000012670 alkaline solution Substances 0.000 description 2
• SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 238000010586 diagram Methods 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 230000035929 gnawing Effects 0.000 description 2
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
• 239000001044 red dye Substances 0.000 description 2
• 239000007858 starting material Substances 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
• WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-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
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
• 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
• JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-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
• YGNDWDUEMICDLW-UHFFFAOYSA-N 7-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC1=CC=CC=C1 YGNDWDUEMICDLW-UHFFFAOYSA-N 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 244000020551 Helianthus annuus Species 0.000 description 1
• 235000003222 Helianthus annuus Nutrition 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
• 229920000297 Rayon Polymers 0.000 description 1
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-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
• 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
• 230000009286 beneficial effect Effects 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
• 150000001576 beta-amino acids Chemical class 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
• 229920002301 cellulose acetate Polymers 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 150000008049 diazo compounds Chemical class 0.000 description 1
• 239000012954 diazonium Substances 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
• 229940097275 indigo Drugs 0.000 description 1
• COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 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
• 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
• 150000004780 naphthols Chemical class 0.000 description 1
• 150000002791 naphthoquinones Chemical class 0.000 description 1
• 150000005002 naphthylamines Chemical class 0.000 description 1
• 239000001048 orange dye Substances 0.000 description 1
• 230000001590 oxidative effect 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
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 230000009467 reduction Effects 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
• 239000011780 sodium chloride Substances 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
• AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
• 229910021653 sulphate ion Inorganic materials 0.000 description 1
• 150000004992 toluidines Chemical class 0.000 description 1
• LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
• 239000000984 vat dye Substances 0.000 description 1