PL35572B1

PL35572B1 -

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Publication number: PL35572B1
Authority: PL; Poland
Prior art keywords: dyes; parts; residue; chromium; starting materials
Prior art date: 1949-02-10

Application number

PL35572A

Other languages

English (en)

Polish (pl)

Filing date

1949-02-10

Publication date

1952-10-31

1949-02-10 Application filed filed Critical

1952-10-31 Publication of PL35572B1 publication Critical patent/PL35572B1/pl

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239000000975 dye Substances 0.000 claims description 52
239000011651 chromium Substances 0.000 claims description 28
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 23
229910052804 chromium Inorganic materials 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 21
238000000034 method Methods 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
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
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
150000001555 benzenes Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
125000000542 sulfonic acid group Chemical group 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 34
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
210000002268 wool Anatomy 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
229910000029 sodium carbonate Inorganic materials 0.000 description 9
239000000126 substance Substances 0.000 description 8
238000001035 drying Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
150000001412 amines Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
235000002639 sodium chloride Nutrition 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
235000010288 sodium nitrite Nutrition 0.000 description 5
150000001989 diazonium salts Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 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
238000001816 cooling Methods 0.000 description 3
238000006193 diazotization reaction Methods 0.000 description 3
238000004043 dyeing Methods 0.000 description 3
230000005923 long-lasting effect Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
-1 sulpho groups Chemical group 0.000 description 3
NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 2
NZDXSXLYLMHYJA-UHFFFAOYSA-M 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C NZDXSXLYLMHYJA-UHFFFAOYSA-M 0.000 description 2
YGUFQYGSBVXPMC-UHFFFAOYSA-N 4-chloro-2,5-dimethoxyaniline Chemical compound COC1=CC(Cl)=C(OC)C=C1N YGUFQYGSBVXPMC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
150000001845 chromium compounds Chemical class 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
150000008049 diazo compounds Chemical class 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
230000007017 scission Effects 0.000 description 2
DPXZULKECUHOKO-UHFFFAOYSA-N 2,5-diethoxy-4-nitroaniline Chemical compound CCOC1=CC([N+]([O-])=O)=C(OCC)C=C1N DPXZULKECUHOKO-UHFFFAOYSA-N 0.000 description 1
XPKFTIYOZUJAGA-UHFFFAOYSA-N 2,5-diethoxyaniline Chemical compound CCOC1=CC=C(OCC)C(N)=C1 XPKFTIYOZUJAGA-UHFFFAOYSA-N 0.000 description 1
CWIBPAGDXLMLNI-UHFFFAOYSA-N 2,5-dimethoxy-4-methylaniline Chemical compound COC1=CC(N)=C(OC)C=C1C CWIBPAGDXLMLNI-UHFFFAOYSA-N 0.000 description 1
ZTQGTYFYOODGOQ-UHFFFAOYSA-N 2,5-dimethoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=C(OC)C=C1N ZTQGTYFYOODGOQ-UHFFFAOYSA-N 0.000 description 1
BJSYSHJRLRFCMG-UHFFFAOYSA-N 3-chloro-1,4-dimethoxycyclohexa-2,4-dien-1-amine Chemical compound COC1(CC=C(C(=C1)Cl)OC)N BJSYSHJRLRFCMG-UHFFFAOYSA-N 0.000 description 1
OTDGGLHARJLEII-UHFFFAOYSA-N 5-butoxy-2-methoxyaniline Chemical compound CCCCOC1=CC=C(OC)C(N)=C1 OTDGGLHARJLEII-UHFFFAOYSA-N 0.000 description 1
GDAIYFAMMVNXNI-UHFFFAOYSA-N 5-ethoxy-2-methoxyaniline Chemical compound CCOC1=CC=C(OC)C(N)=C1 GDAIYFAMMVNXNI-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229910021555 Chromium Chloride Inorganic materials 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
150000001844 chromium Chemical class 0.000 description 1
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
239000011696 chromium(III) sulphate Substances 0.000 description 1
235000015217 chromium(III) sulphate Nutrition 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
DDRCIGNRLHTTIW-UHFFFAOYSA-N n-(4-amino-2,5-dimethoxyphenyl)benzamide Chemical compound C1=C(N)C(OC)=CC(NC(=O)C=2C=CC=CC=2)=C1OC DDRCIGNRLHTTIW-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
238000007747 plating Methods 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1

PL35572A 1949-02-10 PL35572B1 (enExample)