CA1109061A - Sels de colorants 1:2-metal-complexe, exempts de groupements d'acide sulfinique - Google Patents

Sels de colorants 1:2-metal-complexe, exempts de groupements d'acide sulfinique

Info

Publication number: CA1109061A
Authority: CA; Canada
Prior art keywords: atoms; alkyl; formula; hydrogen; dye
Prior art date: 1977-03-21
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

CA299,199A

Other languages

English (en)

Inventor

Paul Lienhard

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.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1977-03-21

Filing date

1978-03-17

Publication date

1981-09-15

1978-03-17 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1981-09-15 Application granted granted Critical

1981-09-15 Publication of CA1109061A publication Critical patent/CA1109061A/fr

Status Expired legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 title claims abstract description 38
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 title claims abstract description 12
239000000434 metal complex dye Substances 0.000 title claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 47
239000000975 dye Substances 0.000 claims abstract description 43
125000000217 alkyl group Chemical group 0.000 claims abstract description 32
-1 sulphamoyl Chemical group 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 19
150000001412 amines Chemical class 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 11
239000001018 xanthene dye Substances 0.000 claims abstract description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
239000011651 chromium Substances 0.000 claims description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
229910052804 chromium Inorganic materials 0.000 claims description 10
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical group [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 9
150000003139 primary aliphatic amines Chemical class 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
150000003254 radicals Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
238000004043 dyeing Methods 0.000 abstract description 11
229920000642 polymer Polymers 0.000 abstract description 8
239000003960 organic solvent Substances 0.000 abstract description 4
150000002431 hydrogen Chemical class 0.000 abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
ACNUVXZPCIABEX-UHFFFAOYSA-N 3',6'-diaminospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(N)C=C1OC1=CC(N)=CC=C21 ACNUVXZPCIABEX-UHFFFAOYSA-N 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
AAIUWVOMXTVLRG-UHFFFAOYSA-N 8,8-dimethylnonan-1-amine Chemical compound CC(C)(C)CCCCCCCN AAIUWVOMXTVLRG-UHFFFAOYSA-N 0.000 description 11
239000000987 azo dye Substances 0.000 description 10
238000007639 printing Methods 0.000 description 10
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 9
235000019253 formic acid Nutrition 0.000 description 9
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 9
JRBAVVHMQRKGLN-UHFFFAOYSA-N 16,16-dimethylheptadecan-1-amine Chemical compound CC(C)(C)CCCCCCCCCCCCCCCN JRBAVVHMQRKGLN-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
239000000123 paper Substances 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
239000000725 suspension Substances 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000000020 Nitrocellulose Substances 0.000 description 4
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
229920001220 nitrocellulos Polymers 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
DVFGEIYOLIFSRX-UHFFFAOYSA-N 3-(2-ethylhexoxy)propan-1-amine Chemical compound CCCCC(CC)COCCCN DVFGEIYOLIFSRX-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 3
239000004411 aluminium Substances 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
229940043265 methyl isobutyl ketone Drugs 0.000 description 3
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 3
238000009987 spinning Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 2
SFLMBHYNCSYPOO-UHFFFAOYSA-N 2-amino-4-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(O)C(N)=C1 SFLMBHYNCSYPOO-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 2
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 2
ZRJOUVOXPWNFOF-UHFFFAOYSA-N 3-dodecoxypropan-1-amine Chemical compound CCCCCCCCCCCCOCCCN ZRJOUVOXPWNFOF-UHFFFAOYSA-N 0.000 description 2
DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
229920001800 Shellac Polymers 0.000 description 2
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
229940081735 acetylcellulose Drugs 0.000 description 2
POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 2
239000002585 base Substances 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
229920002301 cellulose acetate Polymers 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000004040 coloring Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
238000005108 dry cleaning Methods 0.000 description 2
QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
238000010409 ironing Methods 0.000 description 2
229960004592 isopropanol Drugs 0.000 description 2
239000004922 lacquer Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000003801 milling Methods 0.000 description 2
229920006122 polyamide resin Polymers 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000004208 shellac Substances 0.000 description 2
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 2
229940113147 shellac Drugs 0.000 description 2
235000013874 shellac Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
230000009466 transformation Effects 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
QOBAXXQQFJJPAA-UHFFFAOYSA-N 1-(butylamino)propan-2-ol Chemical compound CCCCNCC(C)O QOBAXXQQFJJPAA-UHFFFAOYSA-N 0.000 description 1
HRBCDVLFVGOSIC-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-methyl-1h-pyrazol-3-one Chemical compound N1C(C)=CC(=O)N1C1=CC=CC(Cl)=C1 HRBCDVLFVGOSIC-UHFFFAOYSA-N 0.000 description 1
DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
FEDLEBCVFZMHBP-UHFFFAOYSA-N 2-amino-3-methylphenol Chemical compound CC1=CC=CC(O)=C1N FEDLEBCVFZMHBP-UHFFFAOYSA-N 0.000 description 1
WLJLENRIPLYJSZ-UHFFFAOYSA-N 2-amino-4-(2-methylbutan-2-yl)-6-nitrophenol Chemical compound CCC(C)(C)C1=CC(N)=C(O)C([N+]([O-])=O)=C1 WLJLENRIPLYJSZ-UHFFFAOYSA-N 0.000 description 1
HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
NNZXDXMEXBYSRF-UHFFFAOYSA-N 2-methyl-4h-pyrazol-3-one Chemical compound CN1N=CCC1=O NNZXDXMEXBYSRF-UHFFFAOYSA-N 0.000 description 1
NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
FNACVBYMEBRAOQ-UHFFFAOYSA-N 3-oxo-n-(2-sulfamoylphenyl)butanamide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1S(N)(=O)=O FNACVBYMEBRAOQ-UHFFFAOYSA-N 0.000 description 1
YIGBNEDFDIDTJU-UHFFFAOYSA-N 4-amino-3-hydroxybenzenesulfonamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1O YIGBNEDFDIDTJU-UHFFFAOYSA-N 0.000 description 1
240000000972 Agathis dammara Species 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
229920000298 Cellophane Polymers 0.000 description 1
229920002284 Cellulose triacetate Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 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
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
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229920000297 Rayon Polymers 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241001106476 Violaceae Species 0.000 description 1
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
229960002380 dibutyl phthalate Drugs 0.000 description 1
238000009973 dope dyeing Methods 0.000 description 1
238000000578 dry spinning Methods 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
239000007970 homogeneous dispersion Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
PJFIAKRRJLGWMD-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(OC)C(NC(=O)CC(C)=O)=C1 PJFIAKRRJLGWMD-UHFFFAOYSA-N 0.000 description 1
BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
150000005619 secondary aliphatic amines Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/48—Preparation from other complex metal compounds of azo dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Paper (AREA)
Compositions Of Macromolecular Compounds (AREA)
Cosmetics (AREA)

CA299,199A 1977-03-21 1978-03-17 Sels de colorants 1:2-metal-complexe, exempts de groupements d'acide sulfinique Expired CA1109061A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH3495/77		1977-03-21
CH349577A CH624981A5 (en)	1977-03-21	1977-03-21	Process for the preparation of salts of 1:2 metal complex dyes which are free from sulphonic acid groups

Publications (1)

Publication Number	Publication Date
CA1109061A true CA1109061A (fr)	1981-09-15

Family

ID=4257222

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA299,199A Expired CA1109061A (fr)	1977-03-21	1978-03-17	Sels de colorants 1:2-metal-complexe, exempts de groupements d'acide sulfinique

Country Status (7)

Country	Link
JP (1)	JPS53117026A (fr)
CA (1)	CA1109061A (fr)
CH (1)	CH624981A5 (fr)
DE (1)	DE2811752A1 (fr)
FR (1)	FR2384825A1 (fr)
GB (1)	GB1599812A (fr)
IT (1)	IT7821368A0 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2918633A1 (de) *	1979-05-09	1980-11-20	Bayer Ag	Kobalt-komplexfarbstoffe
US4258118A (en) *	1979-12-26	1981-03-24	Polaroid Corporation	Novel xanthene compounds and photographic products and processes employing the same
US4258119A (en) *	1979-12-26	1981-03-24	Polaroid Corporation	Novel xanthene compounds and photographic products and processes employing the same
US4304834A (en) *	1979-12-26	1981-12-08	Polaroid Corporation	Novel xanthene compounds and photographic products and processes employing the same
JPS6191261A (ja) *	1984-10-12	1986-05-09	Sumitomo Chem Co Ltd	金属錯塩化合物
EP1506547A1 (fr) *	2002-05-17	2005-02-16	Ciba Specialty Chemicals Holding Inc.	Support de stockage optique haute performance
US7442242B2 (en) *	2005-11-30	2008-10-28	Xerox Corporation	Phase change inks containing specific colorants
US7381255B2 (en) *	2005-11-30	2008-06-03	Xerox Corporation	Phase change inks
TWI498385B (zh) *	2009-12-25	2015-09-01	Sumitomo Chemical Co	Pyridine ketone compound compounds
TWI531622B (zh) *	2009-12-25	2016-05-01	Sumitomo Chemical Co	Pyridine ketone compound compounds
JP2012122005A (ja) *	2010-12-09	2012-06-28	Sumitomo Chemical Co Ltd	化合物
JP2012122007A (ja) *	2010-12-09	2012-06-28	Sumitomo Chemical Co Ltd	化合物
TWI518142B (zh) *	2011-03-31	2016-01-21	住友化學股份有限公司	染料用鹽
TWI518143B (zh) *	2011-03-31	2016-01-21	Sumitomo Chemical Co	Dye with salt
JP6135282B2 (ja) *	2013-04-26	2017-05-31	大日本印刷株式会社	色材、色材分散液、カラーフィルタ用着色樹脂組成物、カラーフィルタ、液晶表示装置、及び有機発光表示装置

1977
- 1977-03-21 CH CH349577A patent/CH624981A5/de not_active IP Right Cessation
1978
- 1978-03-17 CA CA299,199A patent/CA1109061A/fr not_active Expired
- 1978-03-17 DE DE19782811752 patent/DE2811752A1/de not_active Withdrawn
- 1978-03-20 GB GB10916/78A patent/GB1599812A/en not_active Expired
- 1978-03-20 IT IT7821368A patent/IT7821368A0/it unknown
- 1978-03-20 JP JP3228778A patent/JPS53117026A/ja active Pending
- 1978-03-21 FR FR7808102A patent/FR2384825A1/fr active Granted

Also Published As

Publication number	Publication date
GB1599812A (en)	1981-10-07
JPS53117026A (en)	1978-10-13
DE2811752A1 (de)	1978-09-28
FR2384825B1 (fr)	1980-04-04
FR2384825A1 (fr)	1978-10-20
CH624981A5 (en)	1981-08-31
IT7821368A0 (it)	1978-03-20

Legal Events

Date	Code	Title	Description
1998-09-15	MKEX	Expiry

Publication	Publication Date	Title
CA1109061A (fr)	1981-09-15	Sels de colorants 1:2-metal-complexe, exempts de groupements d'acide sulfinique
CA1052375A (fr)	1979-04-10	Colorants mono et diazoiques disperses, derives d'amino-2 dicyano-4,5 imidazole
JPH08127749A (ja)	1996-05-21	顔料の分散方法および水性顔料分散体
US3994872A (en)	1976-11-30	Tertiary-alkylamine salts of metal complex dyestuffs
US3150136A (en)	1964-09-22	Certain pyrazoloquinazolone compounds
US4322529A (en)	1982-03-30	Tertiary-alkylamine salts of azine dyestuffs
US4085097A (en)	1978-04-18	Process for the manufacture of chromium complexes from metallizable azo or azo methine dyes
US2728762A (en)	1955-12-27	Azo-dyestuffs of the pyrazolone and pyrazole series
USRE27575E (en)	1973-02-06	Water-insoluble benzimidazolone containing monoazo dyestuffs
US2906747A (en)	1959-09-29	Pyrazolone-1-carboxylic acid amidine monoazo dyestuffs
CA1038865A (fr)	1978-09-19	Preparation industrielle de phtalocyanines tetra-alkyisulfamoyl de cuivre
DE3707715A1 (de)	1988-09-22	Farbstoffe mit n-(2-aminoethyl)piperazingruppen
US3919188A (en)	1975-11-11	Monoazo dyes of the benzisothiazole series which are not soluble in water
US2671081A (en)	1954-03-02	Half-chromed azo dye
US3923774A (en)	1975-12-02	Quinazolone containing phenyl-azo-pyridine compounds
US2721111A (en)	1955-10-18	Oil and spirit soluble azo dyestuffs
US2200005A (en)	1940-05-07	Azo dye compounds and material colored therewith
US3555002A (en)	1971-01-12	Water-insoluble benzimidazolone containing monoazo dyestuffs
US2282323A (en)	1942-05-12	Azo compounds and material colored therewith
US4254026A (en)	1981-03-03	Water-soluble monoazo dyestuffs
US2196776A (en)	1940-04-09	Azo dye compounds and process for coloring therewith
US2249774A (en)	1941-07-22	Azo compound and material colored therewith
US2153627A (en)	1939-04-11	New monoazo dyestuffs
US1983045A (en)	1934-12-04	Coloring matter derived from pyrazolones
US3105829A (en)	1963-10-01	Monoazo dyestuffs of the benzothiazol series