BE423587A

BE423587A -

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Publication number: BE423587A
Authority: BE; Belgium
Prior art keywords: dyes; parts; condensation products; aminotriazines; soluble
Prior art date

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English (en)

French (fr)

Publication of BE423587A publication Critical patent/BE423587A/fr

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239000000975 dye Substances 0.000 claims description 53
239000007859 condensation product Substances 0.000 claims description 40
239000000047 product Substances 0.000 claims description 38
239000000463 material Substances 0.000 claims description 24
239000007787 solid Substances 0.000 claims description 20
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 claims description 20
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 17
239000000543 intermediate Substances 0.000 claims description 12
230000002378 acidificating Effects 0.000 claims description 7
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
238000004043 dyeing Methods 0.000 claims description 6
239000004753 textile Substances 0.000 claims description 5
239000003086 colorant Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 2
239000002671 adjuvant Substances 0.000 claims 1
230000000240 adjuvant Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
229920000742 Cotton Polymers 0.000 description 26
239000004744 fabric Substances 0.000 description 19
230000000694 effects Effects 0.000 description 17
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 15
238000005406 washing Methods 0.000 description 10
239000002253 acid Substances 0.000 description 9
238000009835 boiling Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000000835 fiber Substances 0.000 description 8
239000000344 soap Substances 0.000 description 8
SOIFLUNRINLCBN-UHFFFAOYSA-N Ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000008149 soap solution Substances 0.000 description 6
241000416162 Astragalus gummifer Species 0.000 description 5
229940116362 Tragacanth Drugs 0.000 description 5
229920001615 Tragacanth Polymers 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000000981 basic dye Substances 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000000196 tragacanth Substances 0.000 description 5
235000010487 tragacanth Nutrition 0.000 description 5
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000000982 direct dye Substances 0.000 description 4
230000002209 hydrophobic Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3H-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 3
DGOBMKYRQHEFGQ-UHFFFAOYSA-L Light Green SF yellowish Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 DGOBMKYRQHEFGQ-UHFFFAOYSA-L 0.000 description 3
210000002268 Wool Anatomy 0.000 description 3
239000000980 acid dye Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
230000001264 neutralization Effects 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002562 thickening agent Substances 0.000 description 3
210000001519 tissues Anatomy 0.000 description 3
LNTHITQWFMADLM-UHFFFAOYSA-N Gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
210000003284 Horns Anatomy 0.000 description 2
229920000297 Rayon Polymers 0.000 description 2
210000003491 Skin Anatomy 0.000 description 2
239000004902 Softening Agent Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
239000010985 leather Substances 0.000 description 2
239000000123 paper Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000004627 regenerated cellulose Substances 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-N-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 2
239000007921 spray Substances 0.000 description 2
BSUNTQCMCCQSQH-UHFFFAOYSA-N triazine Chemical compound C1=CN=NN=C1.C1=CN=NN=C1 BSUNTQCMCCQSQH-UHFFFAOYSA-N 0.000 description 2
239000002023 wood Substances 0.000 description 2
ZCOKBQSNYAKTHI-UHFFFAOYSA-N (2,4,6-triamino-2H-1,3,5-triazin-1-yl)methanol Chemical compound NC1N=C(N)N=C(N)N1CO ZCOKBQSNYAKTHI-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-N-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 description 1
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
DEPZVYHSZRMDFX-UHFFFAOYSA-N 2-ethyl-2,3-dihydroxybutanedioic acid Chemical compound CCC(O)(C(O)=O)C(O)C(O)=O DEPZVYHSZRMDFX-UHFFFAOYSA-N 0.000 description 1
ZTFYJIXFKGPCHV-UHFFFAOYSA-N 2-propan-2-ylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C(C)C)=CC=C21 ZTFYJIXFKGPCHV-UHFFFAOYSA-N 0.000 description 1
BCHZICNRHXRCHY-UHFFFAOYSA-N 2H-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 description 1
240000005337 Agave sisalana Species 0.000 description 1
235000011624 Agave sisalana Nutrition 0.000 description 1
RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
240000008564 Boehmeria nivea Species 0.000 description 1
240000000218 Cannabis sativa Species 0.000 description 1
240000000491 Corchorus aestuans Species 0.000 description 1
235000011777 Corchorus aestuans Nutrition 0.000 description 1
235000010862 Corchorus capsularis Nutrition 0.000 description 1
210000003746 Feathers Anatomy 0.000 description 1
229940074391 Gallic acid Drugs 0.000 description 1
240000004533 Hesperis matronalis Species 0.000 description 1
235000015847 Hesperis matronalis Nutrition 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N Melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
240000004713 Pisum sativum Species 0.000 description 1
235000010582 Pisum sativum Nutrition 0.000 description 1
235000017343 Quebracho blanco Nutrition 0.000 description 1
229940043267 Rhodamine B Drugs 0.000 description 1
PYWVYCXTNDRMGF-UHFFFAOYSA-N Rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
241000065615 Schinopsis balansae Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N Sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 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
GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
238000007792 addition Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000000751 azo group Chemical class [*]N=N[*] 0.000 description 1
JNIGYQOBELCEIZ-MAKDUZDQSA-L barium(2+);5-chloro-4-methyl-2-[(2Z)-2-(2-oxonaphthalen-1-ylidene)hydrazinyl]benzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1S([O-])(=O)=O JNIGYQOBELCEIZ-MAKDUZDQSA-L 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
235000009120 camo Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000005607 chanvre indien Nutrition 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
230000023298 conjugation with cellular fusion Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000875 corresponding Effects 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
235000004515 gallic acid Nutrition 0.000 description 1
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000011487 hemp Substances 0.000 description 1
235000012765 hemp Nutrition 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
235000012766 marijuana Nutrition 0.000 description 1
230000013011 mating Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
-1 methylol compound Chemical class 0.000 description 1
239000010446 mirabilite Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000978 natural dye Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
238000011017 operating method Methods 0.000 description 1
230000001151 other effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000001184 potassium carbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
239000005871 repellent Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
GRYBZNLNHVSHPY-UHFFFAOYSA-N sodium;4-hydroxy-5-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]naphthalene-2,7-disulfonic acid Chemical compound [Na+].C=12C(O)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=1NC=C1C=CC=CC1=O GRYBZNLNHVSHPY-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000988 sulfur dye Substances 0.000 description 1
239000000979 synthetic dye Substances 0.000 description 1
239000001648 tannin Substances 0.000 description 1
235000018553 tannin Nutrition 0.000 description 1
229920001864 tannin Polymers 0.000 description 1
JDCJCNVYTGPGAN-PNAMFBHNSA-J tetrasodium;(3E)-5-amino-3-[[4-[4-[(2Z)-2-(8-amino-1-oxo-3,6-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-4-oxonaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].O=C\1C2=C(N)C=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(=CC3=CC(=CC(N)=C3C/2=O)S([O-])(=O)=O)S([O-])(=O)=O)C(OC)=C1 JDCJCNVYTGPGAN-PNAMFBHNSA-J 0.000 description 1
JADVWWSKYZXRGX-UHFFFAOYSA-M thioflavin T Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 JADVWWSKYZXRGX-UHFFFAOYSA-M 0.000 description 1
230000001131 transforming Effects 0.000 description 1
230000021037 unidirectional conjugation Effects 0.000 description 1
239000000984 vat dye Substances 0.000 description 1