CA1077928A - Colorants azoiques heterocycliques de type acyldihydroxybenzene pour les polyolefines metallisees - Google Patents

Colorants azoiques heterocycliques de type acyldihydroxybenzene pour les polyolefines metallisees

Info

Publication number: CA1077928A
Authority: CA; Canada
Prior art keywords: lower alkyl; dye; dyes; polypropylene; nitro
Prior art date: 1976-06-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA269,187A

Other languages

English (en)

Inventor

Raouf Botros

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

American Color and Chemical LLC

Original Assignee

American Color and Chemical LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-06-04

Filing date

1977-01-05

Publication date

1980-05-20

1977-01-05 Application filed by American Color and Chemical LLC filed Critical American Color and Chemical LLC

1980-05-20 Application granted granted Critical

1980-05-20 Publication of CA1077928A publication Critical patent/CA1077928A/fr

Status Expired legal-status Critical Current

Links

229920000098 polyolefin Polymers 0.000 title claims abstract description 10
239000000987 azo dye Substances 0.000 title abstract description 5
125000000623 heterocyclic group Chemical group 0.000 title description 3
-1 nitro, sulfamyl Chemical group 0.000 claims abstract description 40
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
239000000460 chlorine Chemical group 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract description 35
239000000975 dye Substances 0.000 abstract description 32
239000004743 Polypropylene Substances 0.000 abstract description 30
229920001155 polypropylene Polymers 0.000 abstract description 29
239000004744 fabric Substances 0.000 abstract description 21
229910052759 nickel Inorganic materials 0.000 abstract description 17
238000005108 dry cleaning Methods 0.000 abstract description 7
229910052736 halogen Inorganic materials 0.000 abstract description 5
150000002367 halogens Chemical class 0.000 abstract description 5
239000007789 gas Substances 0.000 abstract description 3
150000002431 hydrogen Chemical class 0.000 abstract description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
229910052751 metal Inorganic materials 0.000 description 17
239000002184 metal Substances 0.000 description 17
238000004043 dyeing Methods 0.000 description 16
239000000203 mixture Substances 0.000 description 14
239000000463 material Substances 0.000 description 13
239000000835 fiber Substances 0.000 description 12
239000000243 solution Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
239000002270 dispersing agent Substances 0.000 description 8
238000005859 coupling reaction Methods 0.000 description 7
238000000034 method Methods 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000002657 fibrous material Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000004753 textile Substances 0.000 description 4
229920001213 Polysorbate 20 Polymers 0.000 description 3
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 3
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
LLBBBYLDTDJMNU-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(O)C=C1O LLBBBYLDTDJMNU-UHFFFAOYSA-N 0.000 description 2
SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 2
ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 2
MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 2
RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 2
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
229960004838 phosphoric acid Drugs 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000008149 soap solution Substances 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
238000010998 test method Methods 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
238000001238 wet grinding Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
HEJLFBLJYFSKCE-UHFFFAOYSA-N 2',3'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1O HEJLFBLJYFSKCE-UHFFFAOYSA-N 0.000 description 1
CGJUKQLMOOVGOC-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-6-sulfonamide Chemical compound C1=C(S(N)(=O)=O)C=C2SC(N)=NC2=C1 CGJUKQLMOOVGOC-UHFFFAOYSA-N 0.000 description 1
229940018167 2-amino-5-nitrothiazole Drugs 0.000 description 1
IDPCPTMABJCKGG-UHFFFAOYSA-N 2-amino-n,n-dimethyl-1,3-benzothiazole-6-sulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C2N=C(N)SC2=C1 IDPCPTMABJCKGG-UHFFFAOYSA-N 0.000 description 1
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
OJKLTHIQRARJCE-UHFFFAOYSA-N 2-methoxy-1,3-benzothiazole Chemical compound C1=CC=C2SC(OC)=NC2=C1 OJKLTHIQRARJCE-UHFFFAOYSA-N 0.000 description 1
UZGRZSHGRZYCQV-UHFFFAOYSA-N 4,6-dichloro-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C=C2SC(N)=NC2=C1Cl UZGRZSHGRZYCQV-UHFFFAOYSA-N 0.000 description 1
NDWBXTNRCBNGAK-UHFFFAOYSA-N 4-methyl-5-nitro-1,3-thiazol-2-amine Chemical compound CC=1N=C(N)SC=1[N+]([O-])=O NDWBXTNRCBNGAK-UHFFFAOYSA-N 0.000 description 1
GHKHTBMTSUEBJD-UHFFFAOYSA-N 5,6-dichloro-1,3-benzothiazol-2-amine Chemical compound ClC1=C(Cl)C=C2SC(N)=NC2=C1 GHKHTBMTSUEBJD-UHFFFAOYSA-N 0.000 description 1
DMGAMZGETZDLBL-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3-thiazol-2-amine Chemical compound NC1=NC=C(C(F)(F)F)S1 DMGAMZGETZDLBL-UHFFFAOYSA-N 0.000 description 1
ZPUJTWBWSOOMRP-UHFFFAOYSA-N 5-bromo-1,3-benzothiazol-2-amine Chemical compound BrC1=CC=C2SC(N)=NC2=C1 ZPUJTWBWSOOMRP-UHFFFAOYSA-N 0.000 description 1
XFDCNXIWKCIBAE-UHFFFAOYSA-N 5-bromo-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.NC1=NC=C(Br)S1 XFDCNXIWKCIBAE-UHFFFAOYSA-N 0.000 description 1
MELAGXOBBSTJPI-UHFFFAOYSA-N 5-methyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC=C2SC(N)=NC2=C1 MELAGXOBBSTJPI-UHFFFAOYSA-N 0.000 description 1
KOYJWFGMEBETBU-UHFFFAOYSA-N 6-ethoxy-1,3-benzothiazol-2-amine Chemical compound CCOC1=CC=C2N=C(N)SC2=C1 KOYJWFGMEBETBU-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
239000000305 astragalus gummifer gum Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000013522 chelant Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
XHFUVBWCMLLKOZ-UHFFFAOYSA-N ethyl 2-amino-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(N)=N1 XHFUVBWCMLLKOZ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000005562 fading Methods 0.000 description 1
229930182830 galactose Natural products 0.000 description 1
229940097043 glucuronic acid Drugs 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
238000003801 milling Methods 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
150000002816 nickel compounds Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
KLAKIAVEMQMVBT-UHFFFAOYSA-N p-hydroxy-phenacyl alcohol Natural products OCC(=O)C1=CC=C(O)C=C1 KLAKIAVEMQMVBT-UHFFFAOYSA-N 0.000 description 1
229920000867 polyelectrolyte Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229940080236 sodium cetyl sulfate Drugs 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000013112 stability test Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/79—Polyolefins
- D06P3/795—Polyolefins using metallisable or mordant dyes, dyeing premetallised fibres

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Coloring (AREA)

CA269,187A 1976-06-04 1977-01-05 Colorants azoiques heterocycliques de type acyldihydroxybenzene pour les polyolefines metallisees Expired CA1077928A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US69291176A	1976-06-04	1976-06-04

Publications (1)

Publication Number	Publication Date
CA1077928A true CA1077928A (fr)	1980-05-20

Family

ID=24782553

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA269,187A Expired CA1077928A (fr)	1976-06-04	1977-01-05	Colorants azoiques heterocycliques de type acyldihydroxybenzene pour les polyolefines metallisees

Country Status (5)

Country	Link
JP (1)	JPS52148530A (fr)
AU (1)	AU2571277A (fr)
CA (1)	CA1077928A (fr)
FR (1)	FR2353602A1 (fr)
IT (1)	IT1113253B (fr)

1977
- 1977-01-05 CA CA269,187A patent/CA1077928A/fr not_active Expired
- 1977-03-30 FR FR7709595A patent/FR2353602A1/fr active Granted
- 1977-04-12 JP JP4249677A patent/JPS52148530A/ja active Pending
- 1977-04-27 IT IT914477A patent/IT1113253B/it active
- 1977-06-01 AU AU25712/77A patent/AU2571277A/en not_active Expired

Also Published As

Publication number	Publication date
FR2353602B3 (fr)	1980-05-30
FR2353602A1 (fr)	1977-12-30
JPS52148530A (en)	1977-12-09
AU2571277A (en)	1978-12-07
IT1113253B (it)	1986-01-20

Legal Events

Date	Code	Title	Description
1997-05-20	MKEX	Expiry

Publication	Publication Date	Title
US3413075A (en)	1968-11-26	Azo dyestuff mixtures and aromatic polyester fibers colored therewith
EP0013809B1 (fr)	1983-08-10	Colorants monoazoiques de la série des benzothiazoles, leur préparation et leur utilisation dans la teinture et l'impression de fibres hydrophobes
US3321266A (en)	1967-05-23	Process for the dyeing and printing of polypropylene fibers
US4257943A (en)	1981-03-24	Disperse azo dyestuffs and process for preparation and their use
US4089849A (en)	1978-05-16	Monoazo dyes having a benzthiazolyl substituted phenol or naphthol coupling component
US4053462A (en)	1977-10-11	Unsymmetrical phenyl azo naphthyl chromium complex dyes
US4026663A (en)	1977-05-31	Polyester fabric dyed with monoazo dyestuffs
US4089850A (en)	1978-05-16	Disazo dyes having a benzthiazolyl substituted phenol or naphthol coupling component
CA1080217A (fr)	1980-06-24	Colorants azoiques d'acyldihydroxybenzene pour teindre les polyolefines metallisees
US4066388A (en)	1978-01-03	Disazo dyes derived from 1-acyl-2,4-dihydroxybenzenes and metallized polyolefin dyed therewith
CA1068684A (fr)	1979-12-25	Teintures de type azomethine pour le polypropylene
US4097231A (en)	1978-06-27	Metal-containing polypropylene dyed with monoazo 1-aryl-3-alkyl-5-pyrazolones
GB1578988A (en)	1980-11-12	Mixtures of 1:2 cobalt complexes of azo dyes
CA1068686A (fr)	1979-12-25	Colorants jaune-vert brillants pour le polyester
CA1068682A (fr)	1979-12-25	Teintures de type bisazomethine pour le polypropylene
EP0102729B1 (fr)	1986-11-05	Composés nitrothiazol-azoiques, leur préparation et leur utilisation pour la teinture de fibres synthéthiques
US4118383A (en)	1978-10-03	Azo dyes containing an N-2-pyridine-2,4-dihydroxybenzamide coupler component
US3241907A (en)	1966-03-22	Process for the dyeing of cellulose esters
US4005065A (en)	1977-01-25	Unsymmetrical phenyl azo naphthyl chromium complex dyes
CA1096557A (fr)	1981-03-03	Traduction non-disponible
US3498735A (en)	1970-03-03	Dyeing of polypropylene with dyes of the benzeneazo pyrazolone series
US3781168A (en)	1973-12-25	Process for preparing navy-blue and grey 1:2 chromium and cobalt complex azo-dyestuff mixtures for natural and synthetic polyamide and polyurethane fibres
US3214424A (en)	1965-10-26	Disazo disperse dyestuff
US3929843A (en)	1975-12-30	Dihydroxythiophenoxyanthraquinones
GB1576770A (en)	1980-10-15	Azo dyes containing a benzthiazolyl group