BE627311A

BE627311A -

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Publication number: BE627311A
Authority: BE; Belgium
Prior art keywords: sep; parts; group; dyes; azo
Prior art date

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English (en)

French (fr)

Publication of BE627311A publication Critical patent/BE627311A/fr

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239000000975 dye Substances 0.000 claims description 65
239000011651 chromium Substances 0.000 claims description 27
210000002268 Wool Anatomy 0.000 claims description 26
238000005859 coupling reaction Methods 0.000 claims description 26
230000001808 coupling Effects 0.000 claims description 25
238000010168 coupling process Methods 0.000 claims description 25
239000000835 fiber Substances 0.000 claims description 23
VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 21
229910052804 chromium Inorganic materials 0.000 claims description 19
238000004043 dyeing Methods 0.000 claims description 19
239000000987 azo dye Substances 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 14
239000004952 Polyamide Substances 0.000 claims description 12
229920002647 polyamide Polymers 0.000 claims description 12
239000011528 polyamide (building material) Substances 0.000 claims description 12
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
238000001465 metallisation Methods 0.000 claims description 11
230000000875 corresponding Effects 0.000 claims description 10
239000010985 leather Substances 0.000 claims description 10
-1 azo compound Chemical class 0.000 claims description 9
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 7
125000004429 atoms Chemical group 0.000 claims description 6
150000004696 coordination complex Chemical class 0.000 claims description 6
238000006193 diazotization reaction Methods 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
150000004982 aromatic amines Chemical class 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
238000007639 printing Methods 0.000 claims description 4
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
239000004033 plastic Substances 0.000 claims description 3
229920003023 plastic Polymers 0.000 claims description 3
229920000642 polymer Polymers 0.000 claims description 3
239000002966 varnish Substances 0.000 claims description 3
XTXRWKRVRITETP-UHFFFAOYSA-N vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1H-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 2
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
229910052803 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
238000004040 coloring Methods 0.000 claims description 2
229920001577 copolymer Polymers 0.000 claims description 2
150000005204 hydroxybenzenes Chemical class 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
239000000434 metal complex dye Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
229920002994 synthetic fiber Polymers 0.000 claims 2
240000002275 Cucumis melo Species 0.000 claims 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 claims 1
238000009963 fulling Methods 0.000 claims 1
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 105
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
229910001868 water Inorganic materials 0.000 description 35
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
239000002253 acid Substances 0.000 description 22
239000000243 solution Substances 0.000 description 20
239000011780 sodium chloride Substances 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
229910052801 chlorine Inorganic materials 0.000 description 12
210000004243 Sweat Anatomy 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
239000000843 powder Substances 0.000 description 11
NOPVNWCIHNOJKG-UHFFFAOYSA-N CO[NH-] Chemical compound CO[NH-] NOPVNWCIHNOJKG-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 10
238000005406 washing Methods 0.000 description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
239000011593 sulfur Substances 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
229920002239 polyacrylonitrile Polymers 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
OTYBMLCTZGSZBG-UHFFFAOYSA-L Potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 6
230000002378 acidificating Effects 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000003086 colorant Substances 0.000 description 6
238000005755 formation reaction Methods 0.000 description 6
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
229910052939 potassium sulfate Inorganic materials 0.000 description 6
239000001120 potassium sulphate Substances 0.000 description 6
235000011151 potassium sulphates Nutrition 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000010790 dilution Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000001264 neutralization Effects 0.000 description 5
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical class C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
XEHWPLLDQVKZDO-UHFFFAOYSA-N CCO[NH-] Chemical compound CCO[NH-] XEHWPLLDQVKZDO-UHFFFAOYSA-N 0.000 description 4
239000004677 Nylon Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000027326 copulation Effects 0.000 description 4
229920001778 nylon Polymers 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
229950011260 betanaphthol Drugs 0.000 description 3
238000009835 boiling Methods 0.000 description 3
GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 3
NERQXUOKJAXUHN-UHFFFAOYSA-L cobalt(3+);2-[3-[3-[(2-oxidophenyl)methylideneamino]propylazanidyl]propyliminomethyl]phenolate Chemical compound [Co+3].[O-]C1=CC=CC=C1C=NCCC[N-]CCCN=CC1=CC=CC=C1[O-] NERQXUOKJAXUHN-UHFFFAOYSA-L 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000008049 diazo compounds Chemical class 0.000 description 3
238000007865 diluting Methods 0.000 description 3
239000004744 fabric Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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 3
IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
240000007817 Olea europaea Species 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N Sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001844 chromium Chemical class 0.000 description 2
229910001429 cobalt ion Inorganic materials 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
235000021178 picnic Nutrition 0.000 description 2
238000007747 plating Methods 0.000 description 2
238000004382 potting Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
MSBRDSHNKSLACK-SWKHMZSWSA-N (2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3].O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 MSBRDSHNKSLACK-SWKHMZSWSA-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
SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-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
RDOXTESZEPMUJZ-UHFFFAOYSA-N Anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
NESNTYFIBNMPED-UHFFFAOYSA-N CONS(=O)(=O)C=1C=CC(=C(C1)N)O Chemical compound CONS(=O)(=O)C=1C=CC(=C(C1)N)O NESNTYFIBNMPED-UHFFFAOYSA-N 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
OIDPCXKPHYRNKH-UHFFFAOYSA-J Chrome alum Chemical compound [K]OS(=O)(=O)O[Cr]1OS(=O)(=O)O1 OIDPCXKPHYRNKH-UHFFFAOYSA-J 0.000 description 1
LRCIYVMVWAMTKX-UHFFFAOYSA-L Chromium(II) acetate Chemical compound [Cr+2].CC([O-])=O.CC([O-])=O LRCIYVMVWAMTKX-UHFFFAOYSA-L 0.000 description 1
KTVIXTQDYHMGHF-UHFFFAOYSA-L Cobalt(II) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L Congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
240000000019 Diospyros kaki Species 0.000 description 1
235000008597 Diospyros kaki Nutrition 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
240000007049 Juglans regia Species 0.000 description 1
235000009496 Juglans regia Nutrition 0.000 description 1
VAYOSLLFUXYJDT-RDTXWAMCSA-N LSD Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
210000004185 Liver Anatomy 0.000 description 1
241000920471 Lucilia caesar Species 0.000 description 1
JEDBAYWLBQPWKB-UHFFFAOYSA-N N-(2-ethylhexyl)acetamide Chemical compound CCCCC(CC)CNC(C)=O JEDBAYWLBQPWKB-UHFFFAOYSA-N 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
ODOCHTROFQIEQB-UHFFFAOYSA-M OC1=CC=C2C=CC(=CC2=C1)NC([O-])=O Chemical compound OC1=CC=C2C=CC(=CC2=C1)NC([O-])=O ODOCHTROFQIEQB-UHFFFAOYSA-M 0.000 description 1
XMXNVYPJWBTAHN-UHFFFAOYSA-N Potassium chromate Chemical compound [K+].[K+].[O-][Cr]([O-])(=O)=O XMXNVYPJWBTAHN-UHFFFAOYSA-N 0.000 description 1
PXLIDIMHPNPGMH-UHFFFAOYSA-N Sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000012237 artificial material Substances 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
239000001049 brown dye Substances 0.000 description 1
235000012970 cakes Nutrition 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004532 chromating Methods 0.000 description 1
150000001845 chromium compounds Chemical class 0.000 description 1
229910001430 chromium ion Inorganic materials 0.000 description 1
MVOKRNREBQYLTD-UHFFFAOYSA-L chromium(2+);diformate Chemical compound [Cr+2].[O-]C=O.[O-]C=O MVOKRNREBQYLTD-UHFFFAOYSA-L 0.000 description 1
229940044175 cobalt sulfate Drugs 0.000 description 1
229910000361 cobalt sulfate Inorganic materials 0.000 description 1
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N ethanone Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1