BE498418A - - Google Patents
Info
- Publication number
- BE498418A BE498418A BE498418DA BE498418A BE 498418 A BE498418 A BE 498418A BE 498418D A BE498418D A BE 498418DA BE 498418 A BE498418 A BE 498418A
- Authority
- BE
- Belgium
- Prior art keywords
- radical
- denotes
- dyes
- parts
- acid
- Prior art date
Links
- 239000000975 dye Substances 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000004043 dyeing Methods 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 150000002739 metals Chemical class 0.000 claims description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 238000005755 formation reaction Methods 0.000 claims description 6
- 150000001555 benzenes Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 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 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 210000002268 Wool Anatomy 0.000 description 15
- 230000001808 coupling Effects 0.000 description 13
- 238000010168 coupling process Methods 0.000 description 13
- 238000005859 coupling reaction Methods 0.000 description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- 229910052802 copper Inorganic materials 0.000 description 12
- 239000010949 copper Substances 0.000 description 12
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 10
- ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
- 239000001632 sodium acetate Substances 0.000 description 8
- 235000017281 sodium acetate Nutrition 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 7
- 238000001465 metallisation Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910000365 copper sulfate Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- LGQLOGILCSXPEA-UHFFFAOYSA-L Nickel(II) sulfate Chemical class [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N Orthanilic acid Chemical class NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- PBTUTICKCLVZAB-ZJVSAGCXSA-H copper;tetrasodium;7-[[4-(2-hydroxyethylamino)-6-[[(6E)-6-[(2-oxido-5-sulfonatophenyl)hydrazinylidene]-5-oxo-7-sulfonatonaphthalen-2-yl]amino]-1,3,5-triazin-2-yl]amino]-3-[(4-methoxy-2-sulfonatophenyl)diazenyl]-4-oxidonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].[O-]S(=O)(=O)C1=CC(OC)=CC=C1N=NC(C(=CC1=C2)S([O-])(=O)=O)=C([O-])C1=CC=C2NC1=NC(NCCO)=NC(NC=2C=C3C=C(C(=N/NC=4C(=CC=C(C=4)S([O-])(=O)=O)[O-])/C(=O)C3=CC=2)S([O-])(=O)=O)=N1 PBTUTICKCLVZAB-ZJVSAGCXSA-H 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000007747 plating Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 230000001131 transforming Effects 0.000 description 3
- NDELSWXIAJLWOU-UHFFFAOYSA-N 2,5-dimethyl-4H-pyrazol-3-one Chemical compound CN1N=C(C)CC1=O NDELSWXIAJLWOU-UHFFFAOYSA-N 0.000 description 2
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 2
- VWFBZWHAIIDHRT-UHFFFAOYSA-N 5-methyl-2-propyl-4H-pyrazol-3-one Chemical compound CCCN1N=C(C)CC1=O VWFBZWHAIIDHRT-UHFFFAOYSA-N 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N Barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical class 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 229940053662 nickel sulfate Drugs 0.000 description 2
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-Aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- AACMNEWXGKOJJK-UHFFFAOYSA-N 2-amino-6-nitrophenol Chemical compound NC1=CC=CC([N+]([O-])=O)=C1O AACMNEWXGKOJJK-UHFFFAOYSA-N 0.000 description 1
- BDKWKEPROQIWCA-UHFFFAOYSA-N 2-ethyl-5-methyl-4H-pyrazol-3-one Chemical compound CCN1N=C(C)CC1=O BDKWKEPROQIWCA-UHFFFAOYSA-N 0.000 description 1
- DOEMUQSUNMPUCV-UHFFFAOYSA-N 2-propyl-4H-pyrazol-3-one Chemical compound CCCN1N=CCC1=O DOEMUQSUNMPUCV-UHFFFAOYSA-N 0.000 description 1
- GXINVVNDQWECJP-UHFFFAOYSA-N 3-amino-2-hydroxy-5-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(O)C(S(O)(=O)=O)=C1 GXINVVNDQWECJP-UHFFFAOYSA-N 0.000 description 1
- UARPFAZLXITZKP-UHFFFAOYSA-N 3-amino-2-hydroxybenzenesulfonic acid Chemical group NC1=CC=CC(S(O)(=O)=O)=C1O UARPFAZLXITZKP-UHFFFAOYSA-N 0.000 description 1
- CUQJYQHDIVIFIF-UHFFFAOYSA-N 3-amino-5-benzamido-4-hydroxybenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(NC(=O)C=2C=CC=CC=2)=C1O CUQJYQHDIVIFIF-UHFFFAOYSA-N 0.000 description 1
- VJVXBSHMBSANPG-UHFFFAOYSA-N 3-amino-5-bromo-2-hydroxybenzenesulfonic acid Chemical compound NC1=CC(Br)=CC(S(O)(=O)=O)=C1O VJVXBSHMBSANPG-UHFFFAOYSA-N 0.000 description 1
- NEECEUZBAHTVIN-UHFFFAOYSA-N 4-amino-3-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1Cl NEECEUZBAHTVIN-UHFFFAOYSA-N 0.000 description 1
- JXBUOZMYKQDZFY-UHFFFAOYSA-N 4-hydroxybenzene-1,3-disulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O JXBUOZMYKQDZFY-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- FVELBSCPKVNJHA-UHFFFAOYSA-N 5-acetamido-3-amino-2-hydroxybenzenesulfonic acid Chemical compound CC(=O)NC1=CC(N)=C(O)C(S(O)(=O)=O)=C1 FVELBSCPKVNJHA-UHFFFAOYSA-N 0.000 description 1
- DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N Acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- AIYYMMQIMJOTBM-UHFFFAOYSA-L Nickel(II) acetate Chemical compound [Ni+2].CC([O-])=O.CC([O-])=O AIYYMMQIMJOTBM-UHFFFAOYSA-L 0.000 description 1
- HELHAJAZNSDZJO-UHFFFAOYSA-L Sodium tartrate Chemical compound [Na+].[Na+].[O-]C(=O)C(O)C(O)C([O-])=O HELHAJAZNSDZJO-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- RSJOBNMOMQFPKQ-UHFFFAOYSA-L copper;2,3-dihydroxybutanedioate Chemical compound [Cu+2].[O-]C(=O)C(O)C(O)C([O-])=O RSJOBNMOMQFPKQ-UHFFFAOYSA-L 0.000 description 1
- 230000027326 copulation Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- -1 ethanolamine Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Publications (1)
Publication Number | Publication Date |
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BE498418A true BE498418A (de) |
Family
ID=141097
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BE498418D BE498418A (de) |
Country Status (1)
Country | Link |
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BE (1) | BE498418A (de) |
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0
- BE BE498418D patent/BE498418A/fr unknown