BE518234A - - Google Patents
Info
- Publication number
- BE518234A BE518234A BE518234DA BE518234A BE 518234 A BE518234 A BE 518234A BE 518234D A BE518234D A BE 518234DA BE 518234 A BE518234 A BE 518234A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- hydroxy
- methyl
- acid
- amino
- Prior art date
Links
- 239000000975 dye Substances 0.000 claims description 40
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 14
- 210000002268 Wool Anatomy 0.000 claims description 12
- QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims description 9
- 239000000987 azo dye Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 230000000875 corresponding Effects 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 230000001808 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000012209 synthetic fiber Substances 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002829 nitrogen Chemical group 0.000 claims description 2
- XANZQEFWHPLPRS-UHFFFAOYSA-N 6-amino-1-hydroxycyclohexa-2,4-diene-1-sulfonic acid Chemical compound NC1C=CC=CC1(O)S(O)(=O)=O XANZQEFWHPLPRS-UHFFFAOYSA-N 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 305
- 239000002253 acid Substances 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
- 239000011651 chromium Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 16
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- -1 1-hydroxy-2-amino 6-methyl benzene 4-sulfonic acid N-methylamide Chemical compound 0.000 description 11
- 239000004952 Polyamide Substances 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- 229920002647 polyamide Polymers 0.000 description 9
- 229910052804 chromium Inorganic materials 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000001187 sodium carbonate Substances 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 7
- 238000004040 coloring Methods 0.000 description 6
- 239000011528 polyamide (building material) Substances 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- KIEOKOFEPABQKJ-UHFFFAOYSA-N Sodium dichromate Chemical class [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 5
- CKTNHGVJKUQEBM-UHFFFAOYSA-N ethylazanide Chemical compound CC[NH-] CKTNHGVJKUQEBM-UHFFFAOYSA-N 0.000 description 5
- 230000001264 neutralization Effects 0.000 description 5
- 230000002378 acidificating Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- IAOZVUUQCPRLOI-UHFFFAOYSA-N 3-amino-4-hydroxy-N-phenylbenzenesulfonamide Chemical compound C1=C(O)C(N)=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1 IAOZVUUQCPRLOI-UHFFFAOYSA-N 0.000 description 3
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- NFNLMGYLSDEJKS-UHFFFAOYSA-N 3-amino-4-hydroxy-N-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(O)C(N)=C1 NFNLMGYLSDEJKS-UHFFFAOYSA-N 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N Propanamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001844 chromium Chemical class 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- QGTXBWMKRGHPDD-UHFFFAOYSA-N 3-amino-5-chloro-4-hydroxybenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(Cl)=C1O QGTXBWMKRGHPDD-UHFFFAOYSA-N 0.000 description 1
- JJVNHAPLIQRIHB-UHFFFAOYSA-N 3-amino-N-benzyl-4-hydroxybenzenesulfonamide Chemical compound C1=C(O)C(N)=CC(S(=O)(=O)NCC=2C=CC=CC=2)=C1 JJVNHAPLIQRIHB-UHFFFAOYSA-N 0.000 description 1
- OCFRAVIOHQUKOV-UHFFFAOYSA-N 3-amino-N-butyl-4-hydroxybenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=C(O)C(N)=C1 OCFRAVIOHQUKOV-UHFFFAOYSA-N 0.000 description 1
- QPRBDAGIOLBTPF-UHFFFAOYSA-N 3-amino-N-ethyl-4-hydroxybenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=C(O)C(N)=C1 QPRBDAGIOLBTPF-UHFFFAOYSA-N 0.000 description 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- FDOOTBCQFJWROU-UHFFFAOYSA-N 4-amino-3-hydroxy-N-phenylbenzenesulfonamide Chemical compound C1=C(O)C(N)=CC=C1S(=O)(=O)NC1=CC=CC=C1 FDOOTBCQFJWROU-UHFFFAOYSA-N 0.000 description 1
- ZXGTZMLVXTZUOU-UHFFFAOYSA-N 4-amino-N-ethyl-3-hydroxybenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=C(N)C(O)=C1 ZXGTZMLVXTZUOU-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N Butyramide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- KBMUHGFVZGCZSQ-UHFFFAOYSA-N C(C1=CC=CC=C1)NS(=O)(=O)C=1C=CC(=C(C=1)O)N Chemical compound C(C1=CC=CC=C1)NS(=O)(=O)C=1C=CC(=C(C=1)O)N KBMUHGFVZGCZSQ-UHFFFAOYSA-N 0.000 description 1
- CLGJLNBUITYEHY-UHFFFAOYSA-N CNS(=O)(=O)C1=CC(=C(C(=C1)Cl)O)N Chemical compound CNS(=O)(=O)C1=CC(=C(C(=C1)Cl)O)N CLGJLNBUITYEHY-UHFFFAOYSA-N 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L Cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-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
- 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
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-hydroxy-Succinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- UHNKGFIFLKUJKY-UHFFFAOYSA-N benzylazanide Chemical compound [NH-]CC1=CC=CC=C1 UHNKGFIFLKUJKY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine 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
- 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 1
- NDIDNCPRPZUUHS-UHFFFAOYSA-N chromium;formic acid Chemical compound [Cr].OC=O NDIDNCPRPZUUHS-UHFFFAOYSA-N 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910052803 cobalt Inorganic materials 0.000 description 1
- PJQDFOMVKDFESH-UHFFFAOYSA-N cobalt(2+);N-(9H-fluoren-2-yl)-N-oxidoacetamide Chemical class [Co+2].C1=CC=C2C3=CC=C(N([O-])C(=O)C)C=C3CC2=C1.C1=CC=C2C3=CC=C(N([O-])C(=O)C)C=C3CC2=C1 PJQDFOMVKDFESH-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- NGFQXYLWQODUIL-UHFFFAOYSA-N cyclohexylazanide Chemical compound [NH-]C1CCCCC1 NGFQXYLWQODUIL-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000009963 fulling 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE518234A true BE518234A (ja) |
Family
ID=154863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE518234D BE518234A (ja) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE518234A (ja) |
-
0
- BE BE518234D patent/BE518234A/fr unknown
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