SE184373C1 - - Google Patents
Info
- Publication number
- SE184373C1 SE184373C1 SE184373DA SE184373C1 SE 184373 C1 SE184373 C1 SE 184373C1 SE 184373D A SE184373D A SE 184373DA SE 184373 C1 SE184373 C1 SE 184373C1
- Authority
- SE
- Sweden
- Prior art keywords
- water
- so3h
- ho3s
- process according
- reacted
- Prior art date
Links
- 239000000975 dye Substances 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 19
- 230000008878 coupling Effects 0.000 claims description 16
- 238000010168 coupling process Methods 0.000 claims description 16
- 238000005859 coupling reaction Methods 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 14
- 239000011651 chromium Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000008049 diazo compounds Chemical class 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- -1 polyazo Polymers 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 238000006149 azo coupling reaction Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 description 74
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 72
- 229910052717 sulfur Inorganic materials 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- 239000000835 fiber Substances 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- FYSHPROTETTWKB-UHFFFAOYSA-N 2,4,5,6-tetrabromopyrimidine Chemical compound BrC1=NC(Br)=C(Br)C(Br)=N1 FYSHPROTETTWKB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 150000005694 halopyrimidines Chemical class 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000000463 material 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
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- IPOFQEDKXYAPBX-UHFFFAOYSA-N 1,4-diaminocyclohexa-2,4-diene-1-sulfonic acid Chemical class NC1=CCC(N)(S(O)(=O)=O)C=C1 IPOFQEDKXYAPBX-UHFFFAOYSA-N 0.000 description 1
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical class C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
- JGJUJAYNTZWVAT-UHFFFAOYSA-N 2,4,5-tribromopyrimidine Chemical group BrC1=NC=C(Br)C(Br)=N1 JGJUJAYNTZWVAT-UHFFFAOYSA-N 0.000 description 1
- GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical group ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- SGBQUMZTGSQNAO-UHFFFAOYSA-N 2-hydroxynaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(O)=CC=C21 SGBQUMZTGSQNAO-UHFFFAOYSA-N 0.000 description 1
- CLBQHDAKOPHNQI-UHFFFAOYSA-N 3-amino-2-hydroxynaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(O)C(N)=CC2=C1 CLBQHDAKOPHNQI-UHFFFAOYSA-N 0.000 description 1
- AIRRELHUAAZTTL-UHFFFAOYSA-N 3-nitrobenzenesulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 AIRRELHUAAZTTL-UHFFFAOYSA-N 0.000 description 1
- MOMKYJPSVWEWPM-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=CS1 MOMKYJPSVWEWPM-UHFFFAOYSA-N 0.000 description 1
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 241000766754 Agra Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- MCDZXHYNUZJJFT-UHFFFAOYSA-N C1(=CC=CC=C1)N=NC1=CC=C(C2=CC=CC(=C12)S(=O)(=O)O)S(=O)(=O)O Chemical compound C1(=CC=CC=C1)N=NC1=CC=C(C2=CC=CC(=C12)S(=O)(=O)O)S(=O)(=O)O MCDZXHYNUZJJFT-UHFFFAOYSA-N 0.000 description 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 241000408659 Darpa Species 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 241000492333 Harpa Species 0.000 description 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- BCAARMUWIRURQS-UHFFFAOYSA-N dicalcium;oxocalcium;silicate Chemical compound [Ca+2].[Ca+2].[Ca]=O.[O-][Si]([O-])([O-])[O-] BCAARMUWIRURQS-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 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 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000019983 sodium metaphosphate Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Uppfinnare: J Benz och A Schweizer Prioritet begard fran den 28 maj 1958 (Schweiz) Foreliggande uppfinning avser ett forfarande fOr framstallning av minst en trihalogenpyrimidinrest innehallande vattenlosliga organiska fargamnen tillhorande azoserien, vilket forfarande bestar dari, aft vattenlosliga mono- eller polyazofargamnen, vilka ha minst en utbytbar vateatom, eller fargamneskomponenter, vilka ha minst en utbytbar vateatom, omsattas med 2,4,5,6-tetrahalogenpyrimidin, van i halogen betecknar klor eller brom, och att vid fallet fargamneskomponeater reaktionsprodukterna genom kondensation eller azokoppling everforas till vattenlosliga azofargamnen. Inventors: J Benz and A. Schweizer Priority claimed from 28 May 1958 (Switzerland). a replaceable water atom, or dye component having at least one replaceable water atom, is reacted with 2,4,5,6-tetrahalopyrimidine, used in halogen to denote chlorine or bromine, and in the case of dye compound the reaction products are transferred to the water-soluble by condensation or azo coupling.
Med utbytbara vateatomer fbrstas exempelvis vateatomer tillhOrande hydroxi- och tiolgruppen, foretradesvis emellertid en eventuellt genom alkyl-, hydroxialkyl-, alkoxialkyl- eller halogenalkylrester substituerad aminogrupp. Foljaktligen ifragakomma som vattenlosliga organiska fargamnen framforallt sadana, vilka ha minst en aminogrupp. With exchangeable hydrogen atoms is formed, for example, hydrogen atoms belonging to the hydroxy and thiol group, however, preferably an amino group optionally substituted by alkyl, hydroxyalkyl, alkoxyalkyl or haloalkyl radicals. Consequently, as water-soluble organic dyes, especially those which have at least one amino group.
Aminomono- och -polyazofargamnena kunna ha koordinativt bundna metallatomer, exempelvis krom-, kobolt-, nickel- eller kopparatomer. Man kan aven omsatta sa.dana aminoazofargamnen med 2,4,5,6-tetrahalogenpyrimidiner, vilka ha metalliserbara grupperingar. Sadana fargamen metalliseras t.ex. efter kondensation i substans eller bringas ock i metallfri form enligt en av de vanliga metoderna att reagera med fibern, varvid de erhallna fargningarna kunna efterbehandlas med metallavgivande medel. The amino mono- and polyazo compounds may have coordinately bonded metal atoms, for example chromium, cobalt, nickel or copper atoms. Such aminoazofar compounds can also be reacted with 2,4,5,6-tetrahalopyrimidines, which have metallizable groupings. Such dyes are metallized e.g. after condensation in substance or is also brought into metal-free form according to one of the usual methods of reacting with the fiber, whereby the dyes obtained can be post-treated with metal-releasing agents.
Vidare lampa sig aven fargamnen med minst en reaktionsbenagen hydroxigrupp, saint sadana med en eventuellt monosubstituerad reaktionsbenagen aminogrupp och en reaktionsbenagen hydroxigrupp f Or omsattning med 2,4,5,6-tetrahalogenpyrimidin. Darvid kan aminogruppen och hydroxigruppen vara direkt bundna vid fargamnesmolekylens aromatiska karna eller indirekt bundna vid fargamnesmolekylen Over en alifatisk kedja och eventuellt Over ett bryggled. Som alifatiska kedjor kunna namnas fbljande, namligen —CH,—, —CH,—CH,-----, —CH 2—CH2—CH2—, —CH,—CH— och —CH,—CH,—CH,—CH,—. CH, Som bryggled ifragakomma exempelvis foljande, namligenR' -SO -CO-, -0-, -S-,-S R' R' / 7 CO N , N , NHCONH—, —NHC00—, varvid R' kan beteckna vate, en lagmolekylar alkyl-, hydroxialkyl-, cykloalkyl-, aryl- eller aral- R" kylgrupp eller —N—, van i R" betecknar en acylrest. Furthermore, the dyes with at least one reactive hydroxy group, saint sadana with an optionally monosubstituted reactive amino group and a reactive hydroxy group are reacted with reaction with 2,4,5,6-tetrahalopyrimidine. In this case, the amino group and the hydroxy group can be directly bound to the aromatic nuclei of the dye molecule or indirectly bound to the dye molecule Over an aliphatic chain and optionally Over a bridge link. As aliphatic chains can be named the following, namely —CH, -, —CH, —CH, -----, —CH 2 —CH2 —CH2—, —CH, —CH—, and —CH, —CH, —CH, —CH, -. CH, As the bridge link, for example, the following, namely, R a lower molecular weight alkyl, hydroxyalkyl, cycloalkyl, aryl or aral R group or -N-, van in R "denotes an acyl residue.
Definitionsenligt kan man aven erhana de vattenlosliga, minst en trihalogenerad pyrimidinring innehallande farganmena, om man utgar frail organiska foreningar, vilka ha minst en utbytbar vateatom och dessutom minst en for fargamnesbildning benagen substituent. FOr omsattning till de slutliga fargamnena spelar azokopplingen en viktig roll. Darvid kan man fOrfara pa sa Ott, att man omsatter en minst en utbytbar vateatom och dessutom en diazoterbar aminogrupp innehallande forening med 2,4,5,6-tetrahalogenpyrimidin, diazoterar mellanprodukten och kopplar diazoforeningen med en kopplingskomponent till ett vattenlOsligt fargamne, eller att man omsatter en minst en utbytbar vateatom och dessutom en till diazoterbar aminogrupp overforbar substituent innehallande forening med 2,4,5,6- tetrahalogenpyrimidin, overfor i mellanprodukten denna substituent till aminogrupp, diazoterar aminoforeningen och kopplar diazoforeningen med 2— — en kopplingskomponent till ett vattenlosligt farganme. Man kan emellertid awn omsatta en 2,4,5,6-tetrahalogenpyrimidin med en en reaktionsbenagen och en reaktionstrog aminogrupp innehallande diaminoforening, och harpa anvanda den pa sa satt erhallna, en fri aminogrupp och en trihalogenerad pyrimidinring innehallande kondensationsprodukten som diazokomponent. andra sidan kunna foreningar med minst en utbytbar vateatom och minst en kopplingsbendgen kolatom, t.ex. aminohydroxifereningar, kondenseras med 2,4,5,6-tetrahalogenpyrimidin till en som kopplingskomponent anvandbar mellanprodukt. Givetvis kan man aven koppla diazoforeningen av en en trihalogenpyrimidinring innehallande diazokomponent med en kopplingskomponent, vilken avensa innehaller en trihalogenpyrimidinring. By definition, one can also obtain the water-soluble, at least one trihalogenated pyrimidine ring containing the dyes, if one starts from free organic compounds which have at least one exchangeable hydrogen atom and in addition at least one substituent for dye formation. For turnover to the final dyes, the azo coupling plays an important role. This can be done by reacting at least one exchangeable hydrogen atom and also a diazotizable amino group containing a compound with 2,4,5,6-tetrahalopyrimidine, diazotizing the intermediate and coupling the diazo compound with a coupling component to a water-soluble dye, or converts a substituent containing at least one exchangeable hydrogen atom and in addition a substituent transferable to a diazotizable amino group with 2,4,5,6-tetrahalopyrimidine, converts this substituent into amino group in the intermediate product, diazotizes the amino compound and couples the diazo compound to a water-soluble coupling component . However, it is possible to react a 2,4,5,6-tetrahalopyrimidine with a reactant benogen and a reactive amino group containing diamino compound, and to use the resulting mixture, a free amino group and a trihalogenated pyrimidine ring containing the condensation product as a diazo component. on the other hand, compounds with at least one exchangeable hydrogen atom and at least one coupling bend carbon atom, e.g. aminohydroxy compounds, are condensed with 2,4,5,6-tetrahalopyrimidine to an intermediate which can be used as a coupling component. Of course, the diazo compound of a trihalo-pyrimidine ring containing a diazo component can also be coupled to a coupling component, which avensa contains a trihalo-pyrimidine ring.
Sasom organiska foreningar, vilka kunna an-. vandas for uppbyggnad av pyrimidinfargamnen, ifragakomma exempelvis 1,3- resp. 1,4-diaminobensensuLfonsyror resp. -karbonsyror, 4,4'-diamino-1,1'-difeny1-3-sulfonsyra, 1-(3'- resp. amino)-feny1-3-mety1-5-pyrazoloner, aminohydroxinaftalener och foretradesvis deras sulfonsyror, exempehis 2-amino-5-hydroxinaftalen- 7-sulfonsyra, 2-amino-8-hydroxinaftalen-6-sulfonsyra, 1- amino-8-hydroxinaftalen-4,6-disulfonsyra och 1- amino-8-hydroxinaftalen-3,6-disulfonsyra. As organic associations, which can apply. used for the construction of the pyrimidine dyes, in question for example 1,3- resp. 1,4-diaminobenzenesulfonic acids resp. -carboxylic acids, 4,4'-diamino-1,1'-diphenyl-3-sulfonic acid, 1- (3'- or amino) -phenyl-3-methyl-5-pyrazolones, aminohydroxynaphthalenes and preferably their sulfonic acids, for example 2 -amino-5-hydroxynaphthalene-7-sulfonic acid, 2-amino-8-hydroxynaphthalene-6-sulfonic acid, 1-amino-8-hydroxynaphthalene-4,6-disulfonic acid and 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid .
I det foljande anforas 'Agra fargamnessystem, vilka askadliggora uppfinningen, givetvis utan att begransa denna till dessa. Vid urvalet av utgangsfargamnen resp. av diazo- oeh/eller kopplingskomponenter maste man stadse beakta, att dessa innehalla ett tillrackligt antal vattenlosliggorande substituenter, t.ex. sulfonsyra- oeh/eller karboxylgrupper. 1) Fargamnen med den allmanna formeln HO D— HO S— \ N/R van i A betecknar en trihalogenpyrimidinrest, R betecknar vate eller en lagmolekylar alkylrest och D/ betecknar en diazokomponentrest, vilken her minst en sun, vattenlosliggorande grupp, och vilken eventuellt kan ha azogrupper. In the following, 'Agra dyeing systems are stated, which ash the invention, of course without limiting it to these. When selecting the starting dyes resp. of diazo and / or coupling components, it must always be borne in mind that these contain a sufficient number of water-releasing substituents, e.g. sulfonic acid and / or carboxyl groups. 1) The dyes of the general formula HO D - HO S may have azo groups.
Speciellt vardefulla aro diazokomponenter, vilkas rester Di motsvara formeln /SO 3H Z varvid bensenkarnan Z dessutom kan ha ytterligare substituenter, 1. ex. Particularly valuable aro diazo components, the residues Di of which correspond to the formula / SO 3 H Z, wherein the benzene nucleus Z may also have additional substituents, e.g.
,S0 31-1 Cl—/ SO 011 H8C- CH3SO 31-1 SO,HSOX ClH3C—CO—HN—‹ 1-18C-0— CH8 113C SO 31-1 SO 3H Cl Aven foljande diazokomponentrester kunna N. a. ifragakomma, narnligen SO 3H S0,1-1 HO,S—/ \—N=N—/ / — — 2) Fargamnen med den allmanna formeln HO HN—A HO 3S—I—Y van i A har den ovan angivna betydelsen, det ena Y betecknar Irate och det andra en sulfonsyragrupp, och D, betecknar en diazokomponentrest, viLken kan ha azogrupper och vattenlosliggiirande grupper, t. ex. , S0 31-1 Cl— / SO 011 H8C- CH3SO 31-1 SO, HSOX ClH3C — CO — HN— ‹1-18C-0— CH8 113C SO 31-1 SO 3H Cl Even the following diazo component residues may N. a. , namely SO 3H S0,1-1 HO, S— / \ —N = N— / / - - 2) The dyes with the general formula HO HN — A HO 3S — I — Y van i A have the meaning given above, one Y represents Irate and the other a sulfonic acid group, and D, denotes a diazo component residue, which may have azo groups and water-solubilizing groups, e.g.
SO 3H H3G— ›— SO 311 H3C- CH, SO 3H CI 3) Fargamnen med den allmanna formeln HO3SSO,H och HO3S- \"/ SO3H CH, / H3 \ SO 3H Speciellt yardefulla aro diazokomponenter, vilkas rester motsvara formeln S0,14 varvid bensenkarnan stituenter, t. ex. SO 3H H3G— ›- SO 311 H3C- CH, SO 3H CI 3) The dyes of the general formula HO3SSO, H and HO3S- \" / SO3H CH, / H3 \ SO 3H 14 wherein the benzene nucleus substituents, e.g.
SO 3H Da—N=N—/ z / van i A och R ha de ovan angivna betydelserna, D3 betecknar en diazokomponentrest med minst en. sur, vattenlosliggorande grupp och eventuellt ytterligare substituenter, sasom azogrupper, isynnerhet resterna 1 Z kan ha ytterligare sub- SO 3H CH, H 3C ,S03H H3C—CO—HN- och varvid bensenkarnan Z dessutom kan vara ytterligare substituerad, t. ex. SO 3H Da — N = N— / z / van in A and R have the meanings given above, D3 denotes a diazo component residue with at least one. acid, water-detaching group and optionally further substituents, such as azo groups, in particular the residues 1 Z may have additional sub- SO 3 H CH, H 3 C, SO 3 H H 3 C-CO-HN
CH, —/ N CH, \—NH- \ NH—CO—CH, OCH3 4) Monoazofargainnen med minst tva'. sura, -vattenlesliggorande grupper med den allmanna formeln A—N—D4—N=N—K1 van i A och R ha de ovan anforda betydelserna, D, betecknar en diazokomponentrest, t. ex, — 189 373 — SO3HSO3H —HN—/—HN—HN—‹ >—< ›— \\/ 0—S 3H Dch K1 betecknar resten av en eventuellt ytterligare substituerad hydroxinaftalensulfonsyra, t. ex. CH, - / N CH, \ —NH- \ NH — CO — CH, OCH3 4) The monoazo dye with at least two '. acidic, water-readable groups of the general formula A — N — D4 — N = N — K1 used in A and R have the meanings given above, D, denotes a diazo component residue, e.g., - 189 373 - SO3HSO3H —HN— / —HN — HN— ‹> - <› - \\ / 0 — S 3H Dch K1 denotes the remainder of an optionally further substituted hydroxynaphthalene sulfonic acid, e.g.
HOHO HO SO3H )\/ \/ \/ SO 3H HO NHCOCH3 SO3H HO3S/\/NHCOCH3 HO NH, Y\/\ HO3SSO3HHO 3S/ \/\/ HO3S eller en ketometylenforening, t. ex. HOHO HO SO3H) \ / \ / \ / SO 3H HO NHCOCH3 SO3H HO3S / \ / NHCOCH3 HO NH, Y \ / \ HO3SSO3HHO 3S / \ / \ / HO3S or a ketomethylene compound, e.g.
CH3CH3 ICl CN \ N——SO 3H I\ 0/N—CH—CH—NHCOCH3 —CH—CO / —CH--CO" \ CI CH3 N—CCO—NH HO 3S—CH/COHO 3S—‹ \ CO-6H—\ CO—NH/ NHCOCHCOCH3 SO3H 5) Rrgamnen med den allmanna formeln D3-1'=N—K2—N—A van i A oak R ha de ovan angivna betydelserna, D, betecknar resten av en diazokomponent, vilken har minst en sulfonsyragrupp och eventuellt en azogrupp, t. ex. CH3CH3 ICl CN \ N —— SO 3H I \ 0 / N — CH — CH — NHCOCH3 —CH — CO / —CH - CO "\ CI CH3 N — CCO — NH HO 3S — CH / COHO 3S—‹ \ CO -6H - \ CO — NH / NHCOCHCOCH3 SO3H 5) The radicals of the general formula D3-1 '= N — K2 — N — A van in A oak R at least one sulfonic acid group and optionally an azo group, e.g.
SO3H HO3S SO 3H CD- COOHHO3S \ SO ,H SO 3H — — SO 3HSO 3H H3C—COHN—< och K2 betecknar resten av en i grannstallning till en enoliserbar ketogrupp kopplande kopplingskomponent, sasom CH3 CN\ / —CH—CO'N—N \CH=CH—/ SO 3H HO 3S CH3 N—NH— I \/N- -CH—CO \/ CNNH- COOH NH— CN\ X H3COCHCONH- -CH—CO/ N SO3H HO 3S 6) Metallkomplexforeningar av monoazofargamnen med minst tva sura losliggorande grupper och minst en Over en kvavebrygga bunden trihalogenpyrimidinrest. SO3H HO3S SO 3H CD- COOHHO3S \ SO, H SO 3H - - SO 3HSO 3H H3C — COHN - N \ CH = CH— / SO 3H HO 3S CH3 N — NH— I \ / N- -CH — CO \ / CNNH- COOH NH— CN \ X H3COCHCONH- -CH — CO / N SO3H HO 3S 6) monoazophar strains with at least two acidic loosening groups and at least one trihalogen pyrimidine residue bound over a nitrogen bridge.
Sasom metallatomer ifragakomma krom, kobolt, nickel, framforallt emellertid koppar. As metal atoms come from chromium, cobalt, nickel, but above all copper.
Sasom diazokomponenter for uppbyggnaden av sadana fargamnen ifragakomma hi. a. 2-amino-1 hydroxibensener, 2-amino-1-hydroxi- och 1- amino-2-hydroxinaftalener och 2-aminobensen-1- karbonsyror, medan som kopplingskomponenter exempelvis kunna anvandas 1-(amino)Lary1-5- pyrazoloner och aminohydroxinaftalensulfonsyror. As diazo components for the construction of such dyes come into question hi. a. 2-amino-1 hydroxybenzenes, 2-amino-1-hydroxy- and 1-amino-2-hydroxynaphthalenes and 2-aminobenzene-1-carboxylic acids, while 1- (amino) Lary1-5-pyrazolones can be used as coupling components, for example and aminohydroxynaphthalenesulfonic acids.
Trihalogenpyrimiclinresten kan darvid vara bunden vid kopplingskomponenten, sasom i 101- j ande kombination HO3S0Cu0 HO3SHO,S/\/\/\NH—A eller vid diazokomponenten, t. ex. 0Cu0 N=N A—HN SO ,H HO 3S HO 3S/NN Givetvis kunna icke endast 1: 1-metallkomplex utan aven 2: 1-komplex framstallas. De sistnamnda innehalla som metallatomer foretradesvis krom eller kobolt. The trihalogenpyrimiclin residue can then be bound to the coupling component, as in the 101st combination HO3SOCu0 HO3SHO, S / \ / \ / \ NH-A or to the diazo component, e.g. 0Cu0 N = N A — HN SO, H HO 3S HO 3S / NN Of course, not only 1: 1 metal complexes but also 2: 1 complexes can be produced. The latter contain as metal atoms preferably chromium or cobalt.
Omsattningen av de som utgangsprodukter avsedda fOreningarna eller vattenldsliga f argamnena med 2,4,5,6 - tetrahalogenpyrimidin genomfores foretradesvis i vattenhaltigt medium. Harvid kan halogeniden anvandas som sadan i koncentrerad form eller lost i ett organiskt losningsmedel. Som losningsmedel for halogenpyrimidiner lampa sig isynnerhet aceton, bensen, klorbensen och toluen. The reaction of the starting compounds or aqueous compounds with 2,4,5,6-tetrahalopyrimidine is preferably carried out in aqueous medium. In this case, the halide can be used as such in concentrated form or dissolved in an organic solvent. Acetones, benzene, chlorobenzene and toluene in particular are solvents for halopyrimidines.
Reaktionstemperaturen anpassas efter reaktionsformagan hos de enskilda utgangsproduk terna. Maste hogre temperatur an cirka 40° C anvandas, sa är det med hansyn till vattenangflyktigheten hos halogenpyrimidinerna lampligt att arbeta med reaktionskarl, som fOrsetts med en aterflodeskylare. The reaction temperature is adapted to the reaction shape of the individual starting products. If a temperature higher than about 40 ° C is used, it is appropriate to work with reaction vessels, which are provided with a backflow cooler, in view of the water volatility of the halopyrimidines.
Omsattningen genomf Ores i svagt alkaliskt neutralt till svagt surt medium. For neutralisation av en bildad ekvivalent halogenvate forsattes reaktionslesningen antingen frail borjan med ett syrabindande medal som exempelvis natriumacetat, eller tillsatter man under omsattningen i smd portioner natrium- eller kaliumkarbonat resp. -bikarbonat i fast, pulveriserad form eller som koncentrerad vattenhaltig losning. Som neutralisationsmedel lampa sig emellertid aven vatten- 6— — haltiga losningar av natrium- eller kaliumhydrcodd. Tillsats till reaktionsblandningen av en ringa mangd vat- eller emulgermedel kan paskynda omsattningsreaktionen. The reaction is carried out in ores in slightly alkaline neutral to slightly acidic medium. To neutralize an equivalent halogenate formed, the reaction reading was either continued from the beginning with an acid-binding medal such as sodium acetate, or during the reaction in small portions of sodium or potassium carbonate resp. -bicarbonate in solid, powdered form or as a concentrated aqueous solution. However, aqueous solutions of sodium or potassium hydride can also be used as neutralizing agents. Addition to the reaction mixture of a small amount of water or emulsifier can accelerate the reaction of reaction.
Enligt bada utforingsformerna av forfarandet ledes reaktionen pa sa satt, att endast en halogen-atom av 2,4,5,6-tetrahalogenpyrimidinen reagerar Tried en utbytbar vateatom. According to both embodiments of the process, the reaction is conducted in such a way that only one halogen atom of the 2,4,5,6-tetrahalopyrimidine reacts with a substituted substituted hydrogen atom.
Efter slutford kondensation resp. koppling utsaltas det fardiga pyrimidinfargamnet ur sin eventuellt fOrut neutraliserade losning eller suspension med natrium- eller kaliumklorid eller utMlles med syra, varpa avsuges, tvattas och. torkas. After slutford condensation resp. In connection with coupling, the finished pyrimidine dye is salted out of its optionally neutralized solution or suspension with sodium or potassium chloride or eluted with acid, the warp is filtered off with suction, washed and washed. torkas.
De enligt foreliggande uppfinning erhallna, minst en trihalogenerad pyrirnidinring innehallande, vattenlosliga fargdmnena lampa sig for fargning, klotsning och tryckning av fibrer av animaliskt ursprung, t. ex. yLle, silke, av syntetiska polyamidfibrer, t. ex. nylon, av hider, av cellulosafibrer, t. ex. bomull, linne och av fibrer av regenererad cellulosa, t. ex. viskosrayon, kopparrayon, cellull, samt av blandningar och/eller bildningar av dessa fibrer. De optimala applikationsbetingelserna Oro olika alit efter fiberslag och de fargamnen som anvandas. Animaliska fibrer och syntetiska polyamidfibrer fargar och trycker resp. fixerar man foretradesvis i surt, neutralt eller svagt alkaliskt medium, t. ex. i narvaro av attiksyra, myrsyra, svavelsyra, ammoniumsulfat, natriummetafosfat osv. Man kan aven farga attiksurt till neutralt i narvaro av egaliseringsmedel, t. ex. polyoxetylerade fettaminer eller blandningar av dessa med alkylpolyglykoletrar, och yid slutet avfargningen genomtillsats av ringa mdngder av ett alkaliskt reagerande medal, t, ex. amoniak, natriumbikarbonat, soda osv., eller av foreningar, vilka i varme reagera alkaliskt, t.ex. hexametylentetramin, karbamid, neutralisera badet till neutral eller svagt alkalisk reaktion. Harpá skoljes grundligt och eventuellt surgores med litet attiksyra. The water-soluble dyes obtained according to the present invention, containing at least one trihalogenated pyrimidine ring, are suitable for dyeing, chipping and printing fibers of animal origin, e.g. wool, silk, of synthetic polyamide fibers, e.g. nylon, of hides, of cellulose fibers, e.g. cotton, linen and of regenerated cellulose fibers, e.g. viscose rayon, copper rayon, cellulose, and mixtures and / or formations of these fibers. The optimal application conditions Oro different alit according to fiber type and the dyes used. Animal fibers and synthetic polyamide fibers dye and print resp. is preferably fixed in acidic, neutral or weakly alkaline medium, e.g. in the presence of acetic acid, formic acid, sulfuric acid, ammonium sulphate, sodium metaphosphate, etc. You can also color attic acid to neutral in the presence of leveling agents, e.g. polyoxetylated fatty amines or mixtures thereof with alkyl polyglycol ethers, and at the end of the decolorization the addition of small amounts of an alkaline reacting medal, e.g. ammonia, sodium bicarbonate, soda, etc., or of compounds which in heat react alkaline, e.g. hexamethylenetetramine, urea, neutralize the bath to neutral or slightly alkaline reaction. Harpá is rinsed thoroughly and possibly surgores with a little attic acid.
Vid fargning och tryckning av fibrer och bildningar av animaliskt ursprung och av fibrer och bildningar av polyamid erhalles alit efter fargLinnets reaktivitet ofta en mindre utpraglad bindning mellan fargamnesmolekylen och fibern, i det aft fargamnena delvis Oven pa grund av sin sura karaktar ha affinitet till fibern. When dyeing and printing fibers and formations of animal origin and of fibers and formations of polyamide, alite according to the reactivity of the dye linen, a less pronounced bond is often obtained between the dye molecule and the fiber, in that the dyes have an affinity for the fiber partly due to their acidic nature.
Fargning, klotsning och tryckning resp. fixering av fargamnena pa cellulosafibrer sker med fordel i alkaliskt medium, t. ex. i narvaro av natriumbikarbonat, natriumkarbonat, natronlut, kalilut, natriummetasilikat, natriumborat, trinatriumfosfat, ammoniak osv. For undvikande av reduktionsforeteelser tillsattas vid fargning, klotsning eller tryckning av fibrerna ofta med fordel svaga oxidationsmedel, sasom 1-nitrobensen-3-sulfonsyrat natrium. Fixeringen av fOrgamnena sker i regel dven vid cellulosafibrer i varme. En del av fargamnena, vilka Over en syreatom aro bundna vid trihalogenpyrirnidinringen, kunna vid anvandning av tillrackligt starka alkalier, sasom natriumeller kaliumhydroxid eller trinatriumfosfat, aven fargas resp. fixeras vid laga temperaturer, t. ex. 20-40° C. Staining, grading and printing resp. fixing of the dyes on cellulose fibers takes place advantageously in alkaline medium, e.g. in the presence of sodium bicarbonate, sodium carbonate, sodium hydroxide solution, potassium hydroxide solution, sodium metasilicate, sodium borate, trisodium phosphate, ammonia, etc. In order to avoid reduction phenomena, weak oxidizing agents, such as 1-nitrobenzene-3-sulfonic acid, are often advantageously added when dyeing, chipping or printing the fibers. The fixation of the elements usually takes place in the case of cellulose fibers in heat. Some of the dyes which are attached to an oxygen atom in the trihalopyryridine ring can, when using sufficiently strong alkalis, such as sodium or potassium hydroxide or trisodium phosphate, also be colored resp. fixed at low temperatures, e.g. 20-40 ° C.
Fargningar och tryck pa cellulosafibrer kannetecknas isynnerhet genom framtradande vatakthetsegenskaper. Dessa hero pa bildningen av en stabil kemisk bindning mellan fargdmnesmolekylen och. cellulosamolekylen. Ofta deltager icke hela fargamnesmangden vid den kemiska omsattningen med fibern. Den icke omsatta delen av fargamnet avlagsnas i dessa fall genom lampliga operationer, sasom skoljning och/eller tvaltvattning, eventuellt med anyandning av hogre temperature; fran fibern, varvid dven syntetiska tvattmedel, t.ex. alkylarylsulfonater, natriumlaurylsulfat, natriumlaurylpolyglykoletersulfat samt mono- och dialkylfenolpolyglykoletrar, kunna anvandas. Dyes and prints on cellulosic fibers can be characterized in particular by prominent wetness properties. These are based on the formation of a stable chemical bond between the dye molecule and. cellulose molecules. Often the entire amount of dye does not participate in the chemical reaction with the fiber. The unreacted part of the dye is removed in these cases by suitable operations, such as rinsing and / or soaking, possibly with the use of a higher temperature; from the fiber, whereby dven synthetic detergents, e.g. alkylaryl sulfonates, sodium lauryl sulphate, sodium lauryl polyglycol ether sulphate and mono- and dialkylphenol polyglycol ethers may be used.
I foljande exempel beteckna delar viktdelar, pro cent viktpro cent och temp eraturerna angivas i Celsiusgrader. In the following examples, parts denote parts by weight, percent by weight and the temperatures are given in degrees Celsius.
Exempel 1. 21 delar av fargamnet 2-(4'-amino2'-metyl+fenyl-azo-naftalen-4,8-disulfonsyra lolas neutralt i 400 delar vatten under tillsats av 30-procentig natriumhydroxidlosning och losningen uppvarmes i en med aterflodeskylare och omrorare fOrsedd kolv till 0. Man tillsatter 11 delar 2,4,5,6-tetraklorpyrimidin och hailer blandningen nagra timmar under kraftig omroring vid 50-60°. Det vid reaktionen bildade klorvatet neutraliseras kontinuerligt genom Pion tillsats av utspadd natriumkarbonatlosning under bibehallands av ett pH-varde av 5-6. Nar omsattningen är slutford, vilket kromatografiskt latt kan faststallas, faller man pyrimidinfargamnet genom langsam tillsats av natriumklorid, avfiltrerar fargamnet och tvattar presskakan med utspadd natriumkloridlosning. Det i vakuum yid 80° torkade fargamnet utgores av ett gulbrunt pulver, vilket lOser sig i vatten med gul En cellullvavnad foularderas till en viktokning av cirka 85-procent med en 3-procentig neutral, 50° varm losning av det enligt ovan anforda uppgifter framstallbara fargamnet. Det pa sa stitt impregnerade materialet torkas. For fixering behandlas textilgodset cirka 1 timme i ett bad vid 80-90°, vilket innehaller 250 delar kalcinerat natriumsulfat, 15 delar trinaLriumfosfat och 3 delar 1-nitrobensen-3-sulfonsyrat natrium pa varje 1 000 delar losning. Det fOr fixering anvanda badfOrhallandet utgor 1: 10 till 1: 50. Det behandlade materialet skoljes grundligt med kallt vatten, tvalkokas darpa, skoljes ytterligare en gang och torkas clarpa. Den erhallna rodskiftande gala fargningen har synnerligen goda ljus- och vaLakthetsegenskaper. Den kannetec,knas dessutom genom sin lamplighet for skrynkelfriappretering. Example 1. 21 parts of the dye 2- (4'-amino2'-methyl + phenyl-azonaphthalene-4,8-disulfonic acid are neutralized in 400 parts of water with the addition of 30% sodium hydroxide solution and the solution is heated in a backflow condenser and 11 ml of 2,4,5,6-tetrachloropyrimidine are added and the mixture is stirred for a few hours with vigorous stirring at 50 DEG-60 DEG C. The chlorine water formed in the reaction is continuously neutralized by adding pH value of 5-6 When the reaction is complete, which can be determined chromatographically easily, the pyrimidine dye is dropped by slow addition of sodium chloride, the dye is filtered off and the press cake is washed with dilute sodium chloride solution. , which dissolves in water with yellow. t above apply information manufacturable dye. The impregnated material is dried. For fixing, the fabric is treated for about 1 hour in a bath at 80-90 °, which contains 250 parts of calcined sodium sulphate, 15 parts of trislium phosphate and 3 parts of 1-nitrobenzene-3-sulfonic acid sodium per 1,000 parts of solution. The bathing ratio used for fixation is 1:10 to 1:50. The treated material is thoroughly rinsed with cold water, double-boiled darpa, rinsed once more and dried clarpa. The resulting root-changing gala staining has extremely good light and quality properties. The kannetec, in addition, is crunchy due to its suitability for wrinkle-free finishing.
Ersatter man i detta exempel de 11 delarna 2,4,5,6-tetraklorpyrimidin med 20 delar 2,4,5,6- tetrabrompyrimidin, sa erhaller man ett liknande fargamne, manned erhalles fargningar, vilka ha samma goda egenskaper som ovan beskrivna fargning. If in this example the 11 parts of 2,4,5,6-tetrachloropyrimidine are replaced by 20 parts of 2,4,5,6-tetrabromopyrimidine, a similar dye is obtained, but dyes are obtained which have the same good properties as the coloring described above. .
Exempel 2. 23,5 delar neutralt dinatriumsalt ay fargamnet 2-amino-5-hydroxi-6-fenylazo-naftalen- — —7 2',7-disulfonsyra losas i 500 delar vatten och lOsningen uppvarmes till 65° i en med aterflodeskylning och omrOring forsedd kolv. Under kraftig omrOring tillsatter man 11 delar 2,4,5,6-tetraklorpyrimidin och hailer 4-7 timmar reaktionstemperaturen vid 65-70°. Genom jamn tillsats av 10-procentrig natriumhydroxidlosning Mlles reaktionsblandningen vid ett pH-varde av 4-7. Example 2. 23.5 parts of neutral disodium salt in the dye 2-amino-5-hydroxy-6-phenylazonaphthalene-2 ', 7-disulfonic acid are dissolved in 500 parts of water and the solution is heated to 65 ° in a reflux stirring fitted piston. With vigorous stirring, 11 parts of 2,4,5,6-tetrachloropyrimidine are added and the reaction temperature is maintained at 65-70 ° for 4-7 hours. By uniform addition of 10% sodium hydroxide solution Mlles the reaction mixture at a pH of 4-7.
Efter slutfiird omsattning avskilj es det bildade pyrimidinfargamnet medels koksalt ur lOsningen, avfiltreras och tvaLtas med utspadd koksaltlosning. Fargamnet utgores i torrt tillstand av ett rodbrunt pulver, som i vatten loser sig med orangefarg. After final reaction, the pyrimidine dye formed is separated from the solution by means of brine, filtered off and washed with dilute brine. The dye consists in a dry state of a reddish-brown powder, which dissolves in water with orange color.
Merceriserad boraullssatang tryckes med en tryckpasta med foljande sammansattning, namligen 20 delar av det enligt ovan anforda uppgifter framstallbara fargamnet, 100 delar karbamid, 360 delar vatten, 500 delar 4-procentig natriumalginatfortjock- ning 20 delar natriumkarbonat. 1 000 delar. Mercerized bora wool satin is printed with a printing paste with the following composition, namely 20 parts of the dye, which can be prepared according to the information given above, 100 parts of urea, 360 parts of water, 500 parts of 4% sodium alginate thickening and 20 parts of sodium carbonate. 1,000 parts.
Man torkar vavnaden och behandlar den 5 minuter vid 150° i torr hetta. Det livligt orangefargade trycket skoljes, tvalkokas och skoljes anyo. Man erhaller en ljus- och tvattakta fargning. The tissue is dried and treated for 5 minutes at 150 ° in dry heat. The vivid orange print is rinsed, double boiled and rinsed anyo. You get a light and two-stroke staining.
Exempel 3. 47,8 delar 2-amino-5-hydroxinaftalen-7-sulfonsyra losas vid svagt sur reaktion i 800 delar vatten genom tillsats av 10-procentig natriumhydroxidlosning. Harpa tillsatter man 43,6 delar 2,4,5,6-tetraklorpyrimidin och ror om nagra timmar vid 45-60°. Reaktionsmediets pHvarde Mlles under denna tid genom droppvis tillsats av utspadd natriumkarbonatlosning vid 4,0-4,5. Efter slutford omsattning kyles reaktionsmassan och forsattes med diazoforeningen, vilken man pa vanligt salt erhallit genom diazotering av 34,6 delar 1-amino-bensen-2-sulfonsyra. Genom tillsats av koncentrerad natriumacetatlosning Mlles pH-vardet hos kopplingsblandningen mellan 4,0 och 4,5. Efter omroring 3 timmar installer man pH-vardet med kalcinerad soda pa 6,5-7,0. Efter omroring Over en natt uppvarmer man reaktionsmassan, utsaltar langsaint fargamnet och avfiltrerar detta. Del vid 70-80° torkade fargamnet är identiskt med den produkt, som erhalles enligt uppgifterna i exempel 2. Example 3. 47.8 parts of 2-amino-5-hydroxynaphthalene-7-sulfonic acid are dissolved in a slightly acid reaction in 800 parts of water by the addition of 10% sodium hydroxide solution. Harp is added to 43.6 parts of 2,4,5,6-tetrachloropyrimidine and stirred for a few hours at 45-60 °. The pH value of the reaction medium is measured during this time by dropwise addition of dilute sodium carbonate solution at 4.0-4.5. After final reaction, the reaction mass is cooled and the diazo compound is continued, which is obtained on common salt by diazotization of 34.6 parts of 1-amino-benzene-2-sulfonic acid. By adding concentrated sodium acetate solution Mlles the pH of the coupling mixture between 4.0 and 4.5. After stirring for 3 hours, install the pH value with calcined soda at 6.5-7.0. After stirring overnight, the reaction mass is heated, the longitudinal salt is salted out and filtered off. Part at 70-80 ° dried dye is identical to the product obtained according to the information in Example 2.
Exempel 4. 52,2 delar av fargamnet 1-(2',5'- diklor)- feny1-3-mety1-443"-amino)-feny1-11-azo5-pyrazolon-4',6"-disulfonsyra lOsas neutralt i 700 delar vatten genom tillsats av 30-procentig natriumhydroxidlosning. Man tillsatter 40 delar finpulveriserad 2,4,5,6-tetrabrompyrimidin och uppvarmer reaktionsblandningen nagra timmar vid 55-80°, varvid genom tillsats av utspadd natriumkarbonatlosning ett pH-varde pa 4,5-6,5 uppratthalles. Efter slutford omsattning avskiljes genom filtrering ett ringa overskott tetrabrom pyrimidin och filtratet forsattes langsamt med natriumldorid. Del avskilda fargamnet avfiltreras och torkas. Efter marring erhaller man ett gult pulver, som loser sig i vatten med gul farg. Example 4. 52.2 parts of the dye 1- (2 ', 5'-dichloro) -phenyl-3-methyl-443 "-amino) -phenyl-11-azo5-pyrazolone-4', 6" -disulfonic acid is neutralized in 700 parts of water by adding 30% sodium hydroxide solution. 40 parts of finely powdered 2,4,5,6-tetrabromopyrimidine are added and the reaction mixture is heated for a few hours at 55-80 °, whereby by adding dilute sodium carbonate solution a pH value of 4.5-6.5 is maintained. After final reaction, a small excess of tetrabromo pyrimidine is separated by filtration and the filtrate is slowly added with sodium dloride. Part of the separated dye is filtered off and dried. After marring, a yellow powder is obtained, which dissolves in water with a yellow color.
En tryckpasta innehallande 30 delar av det enligt ovan anfOrda uppgifter framstallbara fargamnet, 100 delar karbamid, 390 delar vatten, 450 delar 4-pro centig natriumalginatfortj ock- ning och 30 delar natriumbikarbonat, 1 000 delar, anvandes for tryckning av joke merceriserad bornullsvavnad. Man torkar trycket och angar detta 10 minuter vid normaltryck. Darpâ forst kallskOljes, sedan varmskoljes vavnaden, tvalkokas 15 minuter och varm- och kallskolj es anyo. Man erhaller ett gronskiftande gull, ljus- och tvattakta tryck. A printing paste containing 30 parts of the dye manufacturable according to the above information, 100 parts of urea, 390 parts of water, 450 parts of 4% sodium alginate thickener and 30 parts of sodium bicarbonate, 1,000 parts, was used for printing joke mercerized boron wool cloth. You dry the pressure and set this for 10 minutes at normal pressure. Then first cold-oiled, then hot-oiled the crust, double-boiled for 15 minutes and hot-cold and cold-oiled anyo. You get a green-changing gold, light and two-stroke print.
Exempel 5. 43,9 delar av fargamnet 1-(5'- hydroxifeny1-11-azo-2-amino-8-hydroxinaftalen6,2'-disulfonsyra lOsas neutralt i 800 delar vatten under tillsats av 30-procentig natriumhydroxidlosning. Efter tillsats av 22 delar 2,4,5,6-tetraklorpyrimidin omrores reaktionsblandMngen cirka 1 timme vid 65-70°, Genom tillsats av utspadd natriu.mkarbonatlosning Mlles reaktionsmediets pH-varde hela tiden mellan 7 och 8. Efter slutford omsattning filtrerar man losningen vid 50° och utsaltar fargamnet ur filtratet genom langsam tillsats av natriumklorid. Efter avfiltrering, torkning i vakuum och darpa foliande malning erhaller man ett morkt pulver, som loser sig i vatten med rod farg. 2 delar air det enligt ovan anforda uppgifter erhallna fargamnet Iösas i 5000 delar vatten. Harpa tillsatter man 2 delar attiksyra och inför vid 50° 100 delar av en yllevaNnad. Man uppvarmer 30 minuter till kokning och hailer clarpa fargbadet 40-60 minuter yid koktemperatur. Nu tillsatter man 5 delar 25-procentig ammoniaklosning oth behandlar fargningen 20 minuter yid 90°. Darph sktiljes grundligt. Under en passage forsatter man skolivallnet med litet myrsyra. Efter torkning erhaller man en rod fargning med god tvatt-, svett- och valkathet. Example 5. 43.9 parts of the dye 1- (5'-hydroxyphenyl-11-azo-2-amino-8-hydroxynaphthalene6,2'-disulfonic acid is dissolved neutrally in 800 parts of water with the addition of 30% sodium hydroxide solution. 22 parts of 2,4,5,6-tetrachloropyrimidine are stirred for the reaction mixture for about 1 hour at 65-70 °. By adding dilute sodium carbonate solution. After the filtration, drying in vacuo and drip foliage grinding, a dark powder is obtained, which dissolves in water with a red color. water. Harpa is added with 2 parts of acetic acid and introduced at 50 ° to 100 parts of a wool mixture. Heat for 30 minutes to boiling and then clarify the dye bath for 40-60 minutes at boiling temperature. Now add 5 parts of 25% ammonia. aklosning oth treats the staining 20 minutes yid 90 °. Darph is thoroughly separated. During a passage, the school wall is continued with a little formic acid. After drying, a red dye is obtained with good washing, sweating and whitening.
I foljande uppstallning ha ytterligare pyrimidbafargamnen anforts, vilka kunna framstallas enligt uppgifterna i exemplen 1-5. I uppstallningen betecknar A en triklorpyrimidinrest och B en tribrompyrimidinrest. 6 0--Cu —N=N HO3S \z—NH—A 0 8 7SO3HOH >N=N-• HO3S NH-A - CH3 Cl /N NH-A CH3 SO3H 8SO3HOH NH-A 11 HO3S OH NH-A SO 3H I> NH-A HO3S0311 CH3 N=C / CO-CH-N=N S031-1 12SO3HHO N=N --/\/\ -NH-A HO SO3H NH-A 13 143S- OH SO3H CH3 -NH-A CH =CH 17 H3C0-‹ SO3H SO3H OH HO Cl Cl HO3S I> NH-A HO3S Cl CH3 N=C / I CO-CH-N=N- 16SO3H -N=N HO3S- HO3S-K<„ _ \-N=N- ›-CH= CH SO3H HO3S 18HO H3C- H03S// NH-A SO3HHO H3C-0C-HN-/\ -N=N-/\/\ HO,SNH-A 26SO3HHO j HO3S-/ \--N=N-/ --N=N-/\/\ \ HO3SNH-A 33 .S081-1 SO 3H _J HO sS—/ \=N HO 39S0311 —N=N GI Hs HO s 36 SO 81-1 HO N=N—/\/ \—NH—A - HO s 41SO 3HHO HsC—N=N--/V\ H,—N —A I ISI CH, HO — 32 HO sSX /1\1\ S081-1HO \ —N—N—/ \ \ \// S /--- HsC/ / \NH—A 34SO 3HHO I HO,S'/ \NH—A HO3S/\/V\NH—‹ \--NH—A CHs HO N =N—I/ \ —NH—A HO3S-1 42SO sH H,C0——N=N 38S0311HO \ —N=N—/\/\—NH—A A—RNHO0S—\\/\/, 43SO3HHO 1\ \ —NH—A HO ,S—w HO 37 HO 3S SO sH HO S031-1HO NH—A SOsH OCHsHO HO— HsC--‹ \—N=N\ HO 56 /CIL— CH, CHC / `CH,— CH3t HO3S HO NH—A I HO3S- / 46HO NH--A HO3S—\)\/—SO3H 47HO NH—A —N=N HO3S—SO3H HO3S 48HO NH—B X/1\ HO3S——N=N HO 3S HO 3 SO3H 53 CH3HONH—A —//\ O—S 3H HO 3S—N=N HO3S— 543H HONH—A H3C0—/—N=N HO 3S— —S0311 5OCH3 HONH—A HO3S y—SO SO3H HO 3S— \/ /—SO 3H — — SO3HHO NH—A —NH—A HO3SS03}1 H3C—/ \ 44S0311HO \—N=N HO3S- \/\/ H,C-0C—HN HO 3S 59 SO ,HHO NH—A 113C 64 HO 3Sr N\ / \ 67SO ,H —SO ,H HO NH—A N=N HO,S—\/ \\/—SO,H HO NH—A 69 HO NH—A 58SO,HHO NH—A C1—‹ I CHO sS H, cHs HO3S— \s/ \z—SO,H HO ,S—S031-1 12 SO,HHO—SO sH 57 164 373 ---, 60 SO,HHO NH—A HO ,S—S— 0,H HO NH—A HsC—/\ 63SO ,H SO ,HHO NH—A ›—N=N:—/\/K HO S 0 ,HHO NH—A —N=N—/\/\ F,C HO NH—A 6SO ,HHO NH—A HO ,S— .\// \/—SO,H —N=N— HO sS 66 H, H2C/ 1-12C \ C H2 68SO ,HHO NH—A —N=N \ HO ,S—w SO,H 61 A—HN 62 N=N HO ,S \s/\/ SO,H 74SO3H HO NH—A N=N HO 3S / 2 CH —CH, CH„CH- \ CH, —CH,/ 80 \/ SO3H SO3H — 70SO3HHO NH—A. 72 CH3 HO3S—HO3S \/ySO3H SO3H 71SO3HHO NH—A 73 el—c)—N=N/K HO S-1 CH3 s \/\// SO3H HO 3S NH—B SO3H HO HO NH—B HO3S—\\ SO3H 75 SO3H /\/\—N=N—< > NHA 76 SO3H /\—N=N—< ›—NH—B \/ \/NH—CO—CH, 78 SO3H ›—NH—A \/ S031-1 79 HO3S—/\/\—N=N——NH--A \—NH—B HO3SLSO sH CH3/ —NH—A 81 SO3HCH3 I /\/\—N=N—\—, NH—A / HO3S- \/\/ SO3H 77 SO3H SO3H NH—CO—CH3—SO3H SO3H COOH SO ,H 88SO 3H HO ,S-‹›-N= 91 SO ,H SO ,H SO ,H CH, 90CH , SO,HCN / >-N=N-CH-CO)N- A-HN 14 82 HO,S - - 84 HO,S OCH, -N=N--N=N-NH-A CH, CH, S-C 311/ H,CX \-N 87SO ,H =N-<, > -NH-A. In the following arrangement, additional pyrimidine baffle strains have been cited, which can be prepared according to the information in Examples 1-5. In the arrangement, A represents a trichloropyrimidine residue and B a tribromopyrimidine residue. 6 0 - Cu —N = N HO3S \ z — NH — A 0 8 7SO3HOH> N = N- • HO3S NH-A - CH3 Cl / N NH-A CH3 SO3H 8SO3HOH NH-A 11 HO3S OH NH-A SO 3H I> NH-A HO3SO311 CH3 N = C / CO-CH-N = N SO31-1 12SO3HHO N = N - / \ / \ -NH-A HO SO3H NH-A 13 143S- OH SO3H CH3 -NH- A CH = CH 17 H3CO- ‹SO3H SO3H OH HO Cl Cl HO3S I> NH-A HO3S Cl CH3 N = C / I CO-CH-N = N- 16SO3H -N = N HO3S- HO3S-K <„ _ \ -N = N- ›-CH = CH SO3H HO3S 18HO H3C- H03S // NH-A SO3HHO H3C-OC-HN - / \ -N = N - / \ / \ HO, SNH-A 26SO3HHO j HO3S- / \ --N = N- / --N = N - / \ / \ \ HO3SNH-A 33 .S081-1 SO 3H _J HO sS— / \ = N HO 39S0311 —N = N GI Hs HO s 36 SO 81- 1 HO N = N - / \ / \ —NH — A - HO s 41SO 3HHO HsC — N = N - / V \ H, —N —AI ISI CH, HO - 32 HO sSX / 1 \ 1 \ S081- 1HO \ —N — N— / \ \ \ // S / --- HsC / / \ NH — A 34SO 3HHO I HO, S '/ \ NH — A HO3S / \ / V \ NH— ‹\ - NH —A CHs HO N = N — I / \ —NH — A HO3S-1 42SO sH H, C0 —— N = N 38S0311HO \ —N = N - / \ / \ - NH — AA — RNHO0S - \\ / \ /, 43SO3HHO 1 \ \ —NH — A HO, S — w HO 37 HO 3S SO sH HO S031-1HO NH — A SOsH OCHsHO HO— HsC - ‹\ —N = N \ HO 56 / CIL— CH, CHC / `CH, - CH3t HO3S HO NH — AI HO3S- / 46HO NH - A HO3S - \) \ / - SO3H 47HO NH — A —N = N HO3S — SO3H HO3S 48HO NH — BX / 1 \ HO3S —— N = N HO 3S HO 3 SO3H 53 CH3HONH — A - // \ O — S 3H HO 3S — N = N HO3S— 543H HONH — A H3C0 - / - N = N HO 3S— —S0311 5OCH3 HONH — A HO3S y — SO SO3H HO 3S— \ / / —SO 3H - - SO3HHO NH — A —NH — A HO3SS03} 1 H3C— / \ 44S0311HO \ - N = N HO3S- \ / \ / H, C-0C — HN HO 3S 59 SO, HHO NH — A 113C 64 HO 3Sr N \ / \ 67SO, H —SO, H HO NH — AN = N HO, S— \ / \\ / - SO, H HO NH — A 69 HO NH — A 58SO, HHO NH — A C1— ‹I CHO sS H, cHs HO3S— \ s / \ z — SO, H HO, S — S031- 1 12 SO, HHO — SO sH 57 164 373 ---, 60 SO, HHO NH — A HO, S — S— 0, H HO NH — A HsC - / \ 63SO, H SO, HHO NH — A ›- N = N: - / \ / K HO S 0, HHO NH — A —N = N - / \ / \ F, C HO NH — A 6SO, HHO NH — A HO, S—. \ // \ / - SO, H —N = N— HO sS 66 H, H2C / 1-12C \ C H2 68SO, HHO NH — A —N = N \ HO, S — w SO, H 61 A — HN 62 N = N HO, S \ s / \ / SO, H 74SO3H HO NH — AN = N HO 3S / 2 CH —CH, CH „CH- \ CH, —CH, / 80 \ / SO3H SO3H - 70SO3HHO NH — A. 72 CH3 HO3S — HO3S \ / ySO3H SO3H 71SO3HHO NH — A 73 el — c) —N = N / K HO S-1 CH3 s \ / \ // SO3H HO 3S NH — B SO3H HO HO NH — B HO3S— \ \ SO3H 75 SO3H / \ / \ - N = N— <> NHA 76 SO3H / \ - N = N— <›—NH — B \ / \ / NH — CO — CH, 78 SO3H› —NH — A \ / S031-1 79 HO3S - / \ / \ - N = N —— NH - A \ —NH — B HO3SLSO sH CH3 / —NH — A 81 SO3HCH3 I / \ / \ - N = N - \ -, NH— A / HO3S- \ / \ / SO3H 77 SO3H SO3H NH — CO — CH3 — SO3H SO3H COOH SO, H 88SO 3H HO, S - ‹› - N = 91 SO, H SO, H SO, H CH, 90CH, SO , HCN /> -N = N-CH-CO) N- A-HN 14 82 HO, S - - 84 HO, S OCH, -N = N - N = N-NH-A CH, CH, SC 311 / H, CX \ -N 87SO, H = N- <,> -NH-A.
NH-CO-CH, NH -B CH, SO ,H 83 HO,S . NH-CO-CH, NH -B CH, SO, H 83 HO, S.
N=N SO ,H 86SO ,H N=N SO ,H N=N SO,H 85 HO ,S NH-S0,-CH, CH, C -CH=CHN-NH-CO-CH, -N=N-CH-00/ HO ,SSOX CH, N=N-NH-A CH, B-HN 89SO ,H - -15_ CH, C-N ,N')-SO3H NN-CH-CO" CI 92 GI 93SO3HCO-CH3 -N-N-CH-CO-NH ›-S031-1 A-HN CH3 SO3HGN\ 03H A-HN-//-N=N-CH -CV \ S 03H CH3 CI CN, A-NH- -CO-NH- -N-N-CH-00' ›-S0,11 -SO3H CH3 ICH, SO3H I N "N-/ ,N--(›-S031-1 /----- \ -N= N-CH-C 07 \ \I/I CI B-HN CH, ICI SO3HC-Ni I\\T/ --/\ / 0-S031-1 -N ---N-CH -CO' 1 \ A-HN 98 CO OH CO OH 94 9 96 97 SO3HCN -N-N-CH-00/N- A-HN SO 31i 108 OH SO3H SO3H CH, CN —N=N—CH—CO — — CH3 1 SO3HC'N _ I\ I _,N— c—> —N=N—CH—00' / H2CCH, A—HN\ / H2C—CH, CH3 I SO3HCN I\ —SO3H A—HN—K \\>—N=N—CH—00/ / CI SO3H ,CO—NH N=N—CH /CO \ CO—NH A—HN CH, ICl CNJ I\ ,N—SO3H —N=N—CH—007 CI 106SO3H —N=N HOsS 107 A—HN 100 101 102 SO3H Cl 10SO3H A—HN SO3HOH N=N—‹ HO3S—c- SO3H OH SO3H CH3 SO a 16 99 CH3 ISO3H S0,11CN A—RN SO3H 103 A—HN OH —N=N- SO3H SO3H 104 B—HN B—RN S031-1 — —17 109SO ,HOH SO ,H1SO,HOH OH II HOS- A—HNA—HNHO ,S S011 , SO ,H116 1SO ,HOH II / —N=N—/ \/\ \ 11 I s HO a A—HN\)\/) 117 \ SO ,H 118SO ,HOH NH—CO—CH, 112SO ,HOHII I < —N—N—/ \" --N=N--/\/\ HO ,S--! \ /\/ 111SO ,HOH —N—N—/\/\ B—HN\/\/ SO,H A—HN A—HN SO ,HNH, > HO—< > SO ,H SO ,H1-12N SO ,H N=N HO 113 A—HN 119SO,HHO NH—00—----> Cl A—HNHO,S4\/ \/ SO,H 114SO ,HOH Cl _ \ HO ,S A—HN 1SO ,H OH NH—CO--Cu, N=N HO 2S——SO ,H \/ \/ A—HN 121 OH NH—CO A—HN 124SO ,HOH 131SO,HOH N=N 1 SO,H 1 SO ,H 18— — 122SO ,HOH129-SO,H N=NA—HN—K —N=N HO aS—NH—CO—C,H,HO ,S-1 \\/ 1SO,H H,C A—UN 126SO ,H 1 H,C—‹ \›—N=N HO ,S A—HN 127 A—FIN—/ 128SO,HOH 1 A—HN—‹N=N--/ HO 8S- 132SOSH A—HN—‹ .›—N=N HO, 133 SO ,HOH A—HN——N =N- -SO ,HHO,S OH Cl —NH—CO—CH, NH—CO—CH, NH, 1 A—HN OH 1 123SO sHOH —NH—CO—C,H, SO,HOH 1 SO \—N =N—NH—A A—FIN——N=N—/\/\ 1HO,S A—HN OH SO ,H OH SO,HOH HO3S- 134 SO ,HOH 1 A—HN—< >—N=N-- HOGS 1SO,H HO 136SO ,H A-HN-• -N=N -/ 110- H,N - -19 SO ,H137SO,HOH OH A-UN-< ›-N=N-/\r/ HO ,SV-8°311 HO3S-\\/ SO,H 141SO ,HOH NH-CO-< SO ,H SO ,H -N=N - HO ,S OH NH-CO-CH, SO,H 138 A-HN 139SO ,H A-HN--N=N- HO 8S--SO ,H OH NH-CO-CH, A-HN-‹ 1 SO ,H Cl Cl HO ,S SO 3H 142SO 3HOH 143SO ,H A-HN-C)--‹ >NN HORS OH -SO ,H SO3H S0311 SO 3H SO 311 OH S031-1 1CH, — — S031-1 A—HN—‹/ >—N=N- \ HO3S OH CI 1SO sHI-12N SO 3H >--N=N--"/\ HO- \/ S0,11 146S031-1OH NH—CO—CH, A—HN— HO3S- SO 311 A—HN—‹>_(>--N=N HO3S- SO ,H A—HN——N= N- H03S HO 3S S0311 149 CH, —SO 3H 144 147 148 OH NH—CO—C—> OH NH—CO—CH, CH, - 184 373 - SO,H 153 CH, SO 3H NH, < CH, A-HN 154 CH, I SO,HCN <---I -\ -N=N-CH-CO'' -CH-CH-NH-B HO,S SO 3H 0,H CH, OH B-HN -N=N 152CH, B-HN-/ SO,H -N-N- HO,S OH SO,H CH, SO 3H 151 21 SO 3H 156CH, COOHI CN I\N--CH- CH- NH-A HO,S-< ›-N-N-CH-00/ HO 3S SO 3H CH, CN ,N- -N-N-CH-00' - NH-A 157 SO,H SO 3H 22- 158 CO OH 8°314CIN H03S--N=N--N=N-CH-CO" NH-A 159 CH, ICI SO3HCNI I I )N--< -NH-A -N=N-CH -CO 160 HO3S CH, CN N=N-CH-CO" SO3H 161SO3HCO-CH, <->-N=N-CH-CO-NH -CH=GH--NH-A HO3SSO3H 162 SO3H SO3H (--- -N=N HO SS NH-A 163OHHO ,SCH, NH-A SO3H CO OHOH HO--N=N- 164GO OH SO 3H S031-1 SO 3H - - HO ,S HO ,S SO 3H SO3H S0,11 HO3S- OH NH2 HO3S-w-SO3H 23 16 166 167 168 169 HO3S 170 SO 2H -CH = CH--NH-A SO3H --NH-A SO3H -N=N HO 3S Cu HO 3SNH-A HO3S 173 CH3 S031-1 174 A HN 0Cu I\cN 11. 1720Cu --O 411. HO3S- N=N- HO NH-A HO 3S 0 21 175 HO3S 0Ni —N=N— HO ,S — 134 373 — 179 NH—A SO 3H Co — SO3H 2 HO3S- Cr 2 HO3S / H3C—C C-0— - N—N- NN Cr HO 3S El HO 181 NH—AJ2 176 177 178 A—HN N —NH—A 0OH —N=N HO ,S SO sH —o HOsS Co Cl HO,S>-0— N HO aS 182 183 — 184 18 HO SS N NH—A2_ ci — — 186 H+ H+ A—HN NH—A) 2 SO 3H 02N—‹ IICr B—HN N _ HO 2S N NH—A2 H+ 2 _ H+ H+ 187 188 Co Cr H+ 26— NO2 • _ 192 HO,S——0— SO ,11 0 H+ \/y Cr HO ,S N NH—A2 SO ,H Co HO,S N NH—Aj2 _ Cr 02N H+ H+ NH—A 2 193 H+ 194 189 190 311A UN- 0,N )—N=N- 0 Cr 0 Cl—"—NN HO aS SO,H NH—A SO 191 H4- Cr 2 _ HO3S- CH, HO3S -N=N- SO3H 203CH, HO Cl CH, A-HN-‹ SO3H Cr HO3S N -0- NH-A 196 - H2N-02s-/ HO3S N I NH-A 2 195 - 197S031-1HO / A-HN S031-1 27 S031-1HO -SO,H SO3H 199SO3HHO =N\-S 03H 1 A-I-1N SOX HO SO ,NH, II HO3S-\/\/-S03H 1-10 OC21-1, SO3H H+ - 198 AHN 201SO3H A-HN 202CH3 A-HN-‹ > SO3H HO 0C21-1, A-TIN 200SO3H - 28 204 - - SO ,HHO OC,H, HO NH'C C-OH / N N HO,SSO,H I O H III e SO ,H NH, SO ,H HO NH-CO I SO,H HO,S A-HN SO,HHO NH-CO- III >-N=N HO ,S 206 A-HN 207 SO 2H A-HN 208 SO ,HHO NH II / C C-NH, III N N S0,11 \ le NH, 209 N SO ,HHO NH/ \ C C -NH- 1III / -\ % C HO ,S- SO,H I NH SO,H A-NH SO,H - -29 HO3S 211SO3H HO NH, 212 SO3H NH-A SO ,CH, NH -A2190Cu Cl SO,NH2 -N=N -SO3H A-HN NH-A -SO3H NH-A -SO3H HO3S- \/-S03H 2140Cu / r/ -N=N HO3S \/I SO3H 20Ni /\-NN HO3S 2170- Cu--U NH-A C1 -N=N SO3H NH -A2180Cu0 NH-A 7\ N=N HO3S \/ SO,H HO3S HO NH-00- -NH-A 216 HO NH, Se-SO,H N=N- HO 3S ›-NH-A 213SO3H A-HN HO NH-CO I HO3S -SO3H HO3S-S03H \/ \ HO3S A-HN HO3S- Cu -N=N HO3S SO3H 2160 - - 2 SO,HSO3H 2210Cu0 NH-A = N HO3S 20Cu0 NH-A HOOC- HO,S SO3HSO 3H 226 HO3S OH SeHO-S0,11 N=N 0-A S0311 SO3H 231 OH S031-1 CH3 SO sCH3 Cu N=N HO ,S Cu N=N HO ,S SO,H 2240Cu HO3S-/ =N HO ,S 227OH -N=N- >-0-CH,- -CHs-O-A. N = N SO, H 86 SO, HN = N SO, HN = N SO, H 85 HO, S NH-SO, -CH, CH, C -CH = CHN-NH-CO-CH, -N = N-CH -00 / HO, SSOX CH, N = N-NH-A CH, B-HN 89SO, H - -15_CH, CN, N ') - SO3H NN-CH-CO "CI 92 GI 93SO3HCO-CH3 -NN- CH-CO-NH ›-SO31-1 A-HN CH3 SO3HGN \ 03H A-HN - // - N = N-CH -CV \ S 03H CH3 CI CN, A-NH- -CO-NH- -NN- CH-00 '›-S0.11 -SO3H CH3 ICH, SO3H IN" N- /, N - (›- S031-1 / ----- \ -N = N-CH-C 07 \ \ I / I CI B-HN CH, ICI SO3HC-Ni I \\ T / - / \ / 0-SO31-1 -N --- N-CH -CO '1 \ A-HN 98 CO OH CO OH 94 9 96 97 SO3HCN -NN-CH-00 / N- A-HN SO 31i 108 OH SO3H SO3H CH, CN —N = N — CH — CO - - CH3 1 SO3HC'N _ I \ I _, N— c—> - N = N — CH — 00 '/ H2CCH, A — HN \ / H2C — CH, CH3 I SO3HCN I \ —SO3H A — HN — K \\> - N = N — CH — 00 // CI SO3H, CO— NH N = N — CH / CO \ CO — NH A — HN CH, ICl CNJ I \, N — SO3H —N = N — CH — 007 CI 106SO3H —N = N HOsS 107 A — HN 100 101 102 SO3H Cl 10SO3H A — HN SO3HOH N = N— ‹HO3S — c- SO3H OH SO3H CH3 SO a 16 99 CH3 ISO3H S0,11CN A — RN SO3H 103 A — HN OH —N = N- SO3H SO3H 104 B — HN B — RN S031 -1 - —17 109SO, HOH SO, H1SO, HOH OH II HOS- A — HNA — HNHO, S S011, SO, H116 1SO, H OH II / —N = N— / \ / \ \ 11 I s HO a A — HN \) \ /) 117 \ SO, H 118SO, HOH NH — CO — CH, 112SO, HOHII I <—N — N— / \ "--N = N - / \ / \ HO, S--! \ / \ / 111SO, HOH —N — N - / \ / \ B — HN \ / \ / SO, HA — HN A — HN SO, HNH,> HO— <> SO, H SO, H1-12N SO, HN = N HO 113 A — HN 119SO, HHO NH — 00 —----> Cl A — HNHO, S4 \ / \ / SO, H 114SO, HOH Cl _ \ HO, SA — HN 1SO, H OH NH— CO - Cu, N = N HO 2S —— SO, H \ / \ / A — HN 121 OH NH — CO A — HN 124SO, HOH 131SO, HOH N = N 1 SO, H 1 SO, H 18— - 122SO, HOH129-SO, HN = NA — HN — K —N = N HO aS — NH — CO — C, H, HO, S-1 \\ / 1SO, HH, CA — UN 126SO, H 1 H, C - ‹\› - N = N HO, SA — HN 127 A — FIN— / 128SO, HOH 1 A — HN— ‹N = N - / HO 8S- 132SOSH A — HN—‹. ›- N = N HO , 133 SO, HOH A — HN —— N = N- -SO, HHO, S OH Cl —NH — CO — CH, NH — CO — CH, NH, 1 A — HN OH 1 123SO sHOH —NH — CO— C, H, SO, HOH 1 SO \ —N = N — NH — AA — FIN —— N = N - / \ / \ 1HO, SA — HN OH SO, H OH SO, HOH HO3S- 134 SO, HOH 1 A — HN— <> —N = N-- HOGS 1SO, H HO 136SO, H A-HN- • -N = N - / 110- H, N - -19 SO, H137SO, HOH OH A-UN- < ›-N = N - / \ r / HO, SV-8 ° 311 HO3S - \\ / SO, H 141SO, HOH NH-CO- <SO, H SO, H -N = N - HO, S OH NH- CO-CH, SO, H 138 A-HN 139SO, H A-HN - N = N- HO 8S - SO, H OH NH-CO-CH, A-HN- ‹1 SO, H Cl Cl HO, S SO 3H 142SO 3HOH 143SO, H A-HN-C) - ‹> NN HORS OH -SO, HS O3H S0311 SO 3H SO 311 OH S031-1 1CH, - - S031-1 A — HN - ‹/> —N = N- \ HO3S OH CI 1SO sHI-12N SO 3H> - N = N -" / \ HO- \ / S0,11 146S031-1OH NH — CO — CH, A — HN— HO3S- SO 311 A — HN - ‹> _ (> - N = N HO3S- SO, HA — HN —— N = N - H03S HO 3S S0311 149 CH, —SO 3H 144 147 148 OH NH — CO — C—> OH NH — CO — CH, CH, - 184 373 - SO, H 153 CH, SO 3H NH, <CH, A- HN 154 CH, I SO, HCN <--- I - \ -N = N-CH-CO '' -CH-CH-NH-B HO, S SO 3H 0, H CH, OH B-HN -N = N 152CH, B-HN- / SO, H -NN- HO, S OH SO, H CH, SO 3H 151 21 SO 3H 156CH, COOHI CN I \ N - CH- CH- NH-A HO, S- < ›-NN-CH-00 / HO 3S SO 3H CH, CN, N- -NN-CH-00 '- NH-A 157 SO, H SO 3H 22- 158 CO OH 8 ° 314CIN H03S - N = N- -N = N-CH-CO "NH-A 159 CH, ICI SO3HCNI II) N - <-NH-A -N = N-CH -CO 160 HO3S CH, CN N = N-CH-CO" SO3H 161SO3HCO -CH, <-> -N = N-CH-CO-NH -CH = GH - NH-A HO3SSO3H 162 SO3H SO3H (--- -N = N HO SS NH-A 163OHHO, SCH, NH-A SO3H CO OHOH HO - N = N- 164GO OH SO 3H S031-1 SO 3H - - HO, S HO, S SO 3H SO3H S0,11 HO3S- OH NH2 HO3S-w-SO3H 23 16 166 167 168 169 HO3S 170 SO 2H -CH = CH - NH-A SO3H --NH-A SO3H -N = N HO 3S Cu HO 3SNH-A HO3S 173 CH3 S031-1 174 A HN 0Cu I \ cN 11. 1720Cu --O 411. HO3S- N = N- HO NH-A HO 3S 0 21 175 HO3S 0Ni —N = N— HO, S - 134 373 - 179 NH — A SO 3H Co - SO3H 2 HO3S- Cr 2 HO3S / H3C — C C-0— - N — N- NN Cr HO 3S El HO 181 NH — AJ2 176 177 178 A — HN N —NH — A 0OH —N = N HO, S SO sH —o HOsS Co Cl HO, S> -0— N HO aS 182 183 - 184 18 HO SS N NH — A2_ ci - - 186 H + H + A — HN NH —A) 2 SO 3H 02N— ‹IICr B — HN N _ HO 2S N NH — A2 H + 2 _ H + H + 187 188 Co Cr H + 26— NO2 • _ 192 HO, S —— 0— SO, 11 0 H + \ / y Cr HO, SN NH — A2 SO, H Co HO, SN NH — Aj2 _ Cr 02N H + H + NH — A 2 193 H + 194 189 190 311A UN- 0, N) —N = N- 0 Cr 0 Cl— "—NN HO aS SO, H NH — A SO 191 H4- Cr 2 _ HO3S- CH, HO3S -N = N- SO3H 203CH, HO Cl CH, A-HN-‹ SO3H Cr HO3S N -0- NH-A 196 - H2N-02s- / HO3S NI NH-A 2 195 - 197S031-1HO / A-HN S031-1 27 S031-1HO -SO, H SO3H 199SO3HHO = N \ -S 03H 1 AI-1N SOX HO SO, NH , II HO3S - \ / \ / - SO3H 1-10 OC21-1, SO3H H + - 198 AHN 201SO3H A-HN 202CH3 A-HN- ‹> SO3H HO 0C21-1, A-TIN 200SO3H - 28 204 - - SO, HHO OC, H, HO NH'C C-OH / NN HO, SSO, HI OH III e SO, H NH, SO, H HO NH-CO I SO, H HO, S A-HN SO, HHO NH-CO- III> -N = N HO, S 206 A-HN 207 SO 2H A- HN 208 SO, HHO NH II / C C-NH, III NN S0.11 \ le NH, 209 N SO, HHO NH / \ CC -NH- 1III / - \% C HO, S- SO, HI NH SO, H A-NH SO, H - -29 HO3S 211SO3H HO NH, 212 SO3H NH-A SO, CH, NH -A2190Cu Cl SO, NH2 -N = N -SO3H A-HN NH-A -SO3H NH-A -SO3H HO3S- \ / - S03H 2140Cu / r / -N = N HO3S \ / I SO3H 20Ni / \ - NN HO3S 2170- Cu - U NH-A C1 -N = N SO3H NH -A2180Cu0 NH-A 7 \ N = N HO3S \ / SO, H HO3S HO NH-00- -NH-A 216 HO NH, Se-SO, HN = N- HO 3S ›-NH-A 213SO3H A-HN HO NH-CO I HO3S -SO3H HO3S- S03H \ / \ HO3S A-HN HO3S- Cu -N = N HO3S SO3H 2160 - - 2 SO, HSO3H 2210Cu0 NH-A = N HO3S 20Cu0 NH-A HOOC- HO, S SO3HSO 3H 226 HO3S OH SeHO-S0,11 N = N 0-A S0311 SO3H 231 OH S031-1 CH3 SO sCH3 Cu N = N HO, S Cu N = N HO, S SO, H 2240Cu HO3S- / = N HO, S 227OH -N = N-> - 0-CH 2 -CH 3 -OA.
SO 3HNH-A SO 3H HO3S- HO3S-w-SO,H 228 HO ,S OH S0,11 HOOC CI NH-A2NH2 0-A HO3S -N=N-‹ >-0-CHs- -C1-12-0-A 222 HO SS 223 Se-N=N-1W -N=N- SO3HCH3 S0311 - - S031-1 31. 232OHCH, -N=N--0-C143-CH2-CH2-0-A SO3H CH3 CH, SO3H \/y SO3H 233OH /CH 2-CH3 -N=N-411. 1W-N=N- CH,-C1-13-0-A S0314 SO3H OH 236 S0311 S031-1 S031-1 238S031-1 241SO3H 2 OH SO3H 239SO3H HO3S-O-S 31-1 237OH -N=N-NH-A HO3S/\/ S0,11 SO 3H CH3 ›-N I C=N `CO-CH-N=N S031-1 SO3H 234 Cl HO 3S- Cl CH, 32— Fargningarna pa bomull, vilka man erhallerFargamnets nrFargton med fargamnena nr 6-241 ha foljande farg-66dito toner:67rod Fargamnets nrFargton68blaskiftande rod 6blaskiftande rod69 dito 7orange70rod 8rod71dito 9gronskiftande gul72blaskiftande rod dito73dito 11rod74dito 12gulskiftande rod7gul 13rOd76rodskiftande gul 14orange77dito gronskiftande gul78dito 16orange79dito 17rOdskiftande gul80dito 18rubin81gul 19rodskiftande orange82rodskiftande gul dito83dito 21orange84dito 22rodskif tande orange8dito 23orange86orangegul 24dito87brunskiftande orange scharlakan88gulbrun 26rod89rodskiftande gul 27orange90gronskiftande gul 28scharlakan91gul 29dito92gulskiftande orange dito93gronskiftande gul 31orange94rodskiftande gul 32scharlakan9gul 33violett96gronskiftande gul 34orangerod97dito rod98gul 36rod99dito 37rod100 guldgul 38orangerod101 gronskiftande gul 39gulskiftande rod102dito scharlakan103gul 41dito104rOdskiftande gul 42rod10orange 43scharlakan106dito 44rOd107dito blaskiftande rod108dito 46rubin109orangerod 47blaskiftande rod1orange 48dito111orangerod 49dito112gulskiftande rod dito113rod 51dito114scharlakan 52rubin1blaskiftande rod 53dito116rod 54dito117rod 5bordeaux118rod 56dito119rod 57dito1blasidftande rod 58rOd121dito 59rod122orange - 60blaskiftande rod123gulskiftande rod 61dito124dito 62rubin1scharlakan 63rod126rod 64violett127 dito 6rubin128 dito — —33 1Vganincts nriVargton 129dito 1blaskiftande rod 131dito 132blaskiftande rOd 133gulskiftande rod 134rod 1blaskiftande rod 136dito 137violett 138violett 139dito 1bordeaux 141dito 142rod 143blaskiftande rod 144dito 1bordeaux 146rodskiftande violett 147dito 148bordeaux 149dito 1scharlakan 151rod 152rod 153rod 154rOd 15gul 156dito 157dito 158orange 159gul 160rodskiftande gal 161gul 162rod • 163scharlakan 164brunrod 16rodbrun 166brunskiftande orange 167gronskiftande gul 168morkgron 169rOdskiftande gul 170rod 171violettrod 172violettbla 173violett 174blarod 17rodbrun 176rodskiftande marinbla 177gra 178olivgron 179rodskiftande marinbla 180rodsldftande marinbla 181marinbla 182brunskiftande violett 183gra 184brunskiftande violett 18gronskiftande gra 186gra 187rOdskiftande marinbla 188brun 189rodskiftande marinbla 190brunskiftande violett 191gra Targaninkts",nr.FArgtori 192'lithrinbla. 193brunskiftande violett. 191., .rodskiftande marinbla 195- -ma.tinbla 196rOdskiftande marinhla 197gulskiftande rod 198 -gulskiftande rbd - 199:rodorange 200-rod 201gulskiftande rod 202rOd 203rod 204bordeaux 20blaskiftande rod 206dito 207dito 208dito 209dito 2dito 211bIagra 212morkgron 213blaskiftande rod 214violett 2rodskiftande violett 216blaskiftande violett 217violett -218rodskiftande violett 219violett 2rodsldftande violett 221dito 222vioIett 223dito 224rodskiftande violett 2dito 226scharlakan 227gulskiftande rod 228dito 229gul 2rod 231scharlakan 232dito 233brunskiftande rod 234gul 2rod 236blaskiftande rod 237gulskiftande rod 238gul 239gul 2gul 241gul SO 3HNH-A SO 3H HO3S- HO3S-w-SO, H 228 HO, S OH S0,11 HOOC CI NH-A2NH2 0-A HO3S -N = N- ‹> -0-CHs- -C1-12-0 -A 222 HO SS 223 Se-N = N-1W -N = N- SO3HCH3 SO311 - - S031-1 31. 232OHCH, -N = N - 0-C143-CH2-CH2-0-A SO3H CH3 CH, SO3H / y SO3H 233OH / CH 2 -CH3 -N = N-411. 1W-N = N- CH, -C1-13-0-A S0314 SO3H OH 236 S0311 S031-1 S031-1 238S031-1 241SO3H 2 OH SO3H 239SO3H HO3S-OS 31-1 237OH -N = N-NH-A HO3S / \ / S0,11 SO 3H CH3 ›-NIC = N` CO-CH-N = N S031-1 SO3H 234 Cl HO 3S- Cl CH, 32— The dyes on cotton, which are obtainedFargamnets nrFargton med fargamnena nr 6- 241 have the following color-66dito tones: 67rod Fargamnets nrFargton68blaskiftande rod 6blaskiftande rod69 ditto 7orange70rod 8rod71dito 9gronskiftande gul72blaskiftande rod dito73dito 11rod74dito 12gulskiftande rod7gul 13rOd76rodskiftande yellow 14orange77dito gronskiftande gul78dito 16orange79dito 17rOdskiftande gul80dito 18rubin81gul 19rodskiftande orange82rodskiftande yellow dito83dito 21orange84dito 22rodskif-making orange8dito 23orange86orangegul 24dito87brunskiftande orange scharlakan88gulbrun 26rod89rodskiftande yellow 27orange90gronskiftande yellow 28scharlakan91gul 29dito92gull-changing orange ditto93green-shifting yellow 31orange94roth-shifting yellow 32scharlakan9gul 33violet96green-shifting yellow 34orangerod97dito rod98g ul 36rod99dito 37rod100 gold 38orangerod101 gronskiftande yellow 39gulskiftande rod102dito scharlakan103gul 41dito104rOdskiftande yellow 42rod10orange 43scharlakan106dito 44rOd107dito bluish rod108dito 46rubin109orangerod 47blaskiftande rod1orange 48dito111orangerod 49dito112gulskiftande rod dito113rod 51dito114scharlakan 52rubin1blaskiftande rod 53dito116rod 54dito117rod 5bordeaux118rod 56dito119rod 57dito1blasidftande rod 58rOd121dito 59rod122orange - 60blaskiftande rod123gulskiftande rod 61dito124dito 62rubin1scharlakan 63rod126rod 64violett127 6rubin128 ditto ditto - -33 1Vganincts nriVargton 129dito 1blaskiftande rod 131dito 132blaskiftande 133gulskiftande Rod Rod Rod 134rod 1blaskiftande 136dito 137violett 138violett 139dito 1bordeaux 141dito 142rod 143blaskiftande rod 144dito 1bordeaux 146rodskiftande violet 147dito 148bordeaux 149dito 1scharlakan 151rod 152rod 153rod 154rOd 15gul 156dito 157dito 158orange 159gul 160rodskiftande gal 161gul 162rod • 163scharlakan 164brunrod 16r odbrun 166brunskiftande 167gronskiftande orange yellow yellow 168morkgron 169rOdskiftande 170rod 171violettrod 172violettbla 173violett 174blarod 17rodbrun 176rodskiftande navy 177gra 178olivgron 179rodskiftande navy 180rodsldftande navy 181marinbla 182brunskiftande violet 183gra 184brunskiftande violet 18gronskiftande make 186gra 187rOdskiftande navy 188brun 189rodskiftande navy 190brunskiftande violet 191gra Targaninkts "nr.FArgtori 192'lithrinbla. 193 brown-changing violet. 191. 218rod-changing violet 219violet 2rodsldftande violet 221dito 222violet 223dito 224rodshifting violet 2dito 226scharlakan 227gulskiftande rod 228dito 229gul 2rod 231scharlakan 232dito 233brunskiftande rod 234gul 2rod 237blg 237bl
Claims (3)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE184373T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE184373C1 true SE184373C1 (en) | 1963-01-01 |
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|---|---|---|---|
| SE184373D SE184373C1 (en) |
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| SE (1) | SE184373C1 (en) |
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0
- SE SE184373D patent/SE184373C1/sv unknown
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