JPS6043384B2 - 水不溶性ジスアゾメチン化合物並びにその製法及び使用法 - Google Patents
水不溶性ジスアゾメチン化合物並びにその製法及び使用法Info
- Publication number
- JPS6043384B2 JPS6043384B2 JP51038839A JP3883976A JPS6043384B2 JP S6043384 B2 JPS6043384 B2 JP S6043384B2 JP 51038839 A JP51038839 A JP 51038839A JP 3883976 A JP3883976 A JP 3883976A JP S6043384 B2 JPS6043384 B2 JP S6043384B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- lower alkyl
- general formula
- tables
- formulas
- Prior art date
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 14
- -1 cyan group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 239000004922 lacquer Substances 0.000 claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003973 paint Substances 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 238000009987 spinning Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 1
- 239000004033 plastic Substances 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- 239000000049 pigment Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 235000021419 vinegar Nutrition 0.000 description 4
- 239000000052 vinegar Substances 0.000 description 4
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001465 metallisation Methods 0.000 description 3
- 229940078494 nickel acetate Drugs 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 150000004002 naphthaldehydes Chemical class 0.000 description 2
- 150000002815 nickel Chemical class 0.000 description 2
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 2
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- ACZIUXLIPAUBEH-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbaldehyde;nickel Chemical compound [Ni].C1=CC=CC2=C(C=O)C(O)=CC=C21 ACZIUXLIPAUBEH-UHFFFAOYSA-N 0.000 description 1
- RQWJHUJJBYMJMN-UHFFFAOYSA-N 4-(trifluoromethyl)benzene-1,2-diamine Chemical group NC1=CC=C(C(F)(F)F)C=C1N RQWJHUJJBYMJMN-UHFFFAOYSA-N 0.000 description 1
- ZZNAYFWAXZJITH-UHFFFAOYSA-N 4-amino-3-nitrobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1[N+]([O-])=O ZZNAYFWAXZJITH-UHFFFAOYSA-N 0.000 description 1
- KSLRFRXKUAIWDV-UHFFFAOYSA-N 4-ethoxy-5-methylbenzene-1,2-diamine Chemical compound CCOC1=CC(N)=C(N)C=C1C KSLRFRXKUAIWDV-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001058 brown pigment Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000010431 corundum Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- FAQOZARUOBFXBH-UHFFFAOYSA-N nitroformamide Chemical compound NC(=O)[N+]([O-])=O FAQOZARUOBFXBH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XEFJCMNRPKBUOC-UHFFFAOYSA-N phenyl peroxycyanate Chemical class N#COOC1=CC=CC=C1 XEFJCMNRPKBUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension 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
- C09B55/00—Azomethine dyes
- C09B55/005—Disazomethine dyes
- C09B55/007—Disazomethine dyes containing only carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/13—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azomethine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2515523A DE2515523C3 (de) | 1975-04-09 | 1975-04-09 | Wasserunlösliche Disazomethinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel |
| DE2515523.1 | 1975-04-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51123226A JPS51123226A (en) | 1976-10-27 |
| JPS6043384B2 true JPS6043384B2 (ja) | 1985-09-27 |
Family
ID=5943424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51038839A Expired JPS6043384B2 (ja) | 1975-04-09 | 1976-04-08 | 水不溶性ジスアゾメチン化合物並びにその製法及び使用法 |
Country Status (14)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2610308A1 (de) * | 1976-03-12 | 1977-09-15 | Hoechst Ag | Wasserunloesliche disazomethin-mischkomplexe, verfahren zu ihrer herstellung und ihre verwendung als farbmittel |
| GB1564231A (en) * | 1977-05-31 | 1980-04-02 | Ciba Geigy Ag | Process for the production of a bisazomethine pigment |
| DE2801288C2 (de) * | 1978-01-13 | 1985-06-20 | Hoechst Ag, 6230 Frankfurt | Verwendung von wasserunlöslichen Diazomethinverbindungen zum Färben von thermoplastischen Polyestern in der Masse und in der Spinnfärbung von thermoplastischen Polyestern |
| CH655508B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1981-08-26 | 1986-04-30 | ||
| GB0100963D0 (en) | 2001-01-15 | 2001-02-28 | Clariant Int Ltd | Improvements relating to organic compounds |
| GB0101546D0 (en) | 2001-01-22 | 2001-03-07 | Clariant Int Ltd | Use of pigment dyes for dispersion dyeing from aqueous media |
| GB0101544D0 (en) | 2001-01-22 | 2001-03-07 | Clariant Int Ltd | Use of pigment dyes for dispersion dyeing from aqueous media |
| KR102734284B1 (ko) * | 2018-12-06 | 2024-11-25 | 주식회사 엘지화학 | 색재 조성물, 감광성 수지 조성물, 감광재, 컬러필터, 및 디스플레이 장치 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2993065A (en) * | 1956-10-24 | 1961-07-18 | Interchem Corp | Pigment and method of preparing same |
| US3398170A (en) * | 1964-05-21 | 1968-08-20 | Universal Oil Prod Co | Mixed chelates of a schiff base, an amine, and a transition series metal |
| FR1469573A (fr) * | 1966-01-04 | 1967-02-17 | Kuhlmann Ets | Pigments azométhiniques métallifères |
| US3472876A (en) * | 1967-08-18 | 1969-10-14 | Shell Oil Co | Olefin epoxidation |
| BE795836A (fr) * | 1972-02-24 | 1973-08-23 | Ciba Geigy | Pigment bis-azomethinique et sa preparation |
| GB1413511A (en) * | 1972-03-20 | 1975-11-12 | Ciba Geigy Ag | Metallised bisazomethine pigments |
| US3939194A (en) * | 1972-06-19 | 1976-02-17 | Ciba-Geigy Corporation | Bis-2-azomethine pigments, process for their manufacture and their use |
| CH568368A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-06-19 | 1975-10-31 | Ciba Geigy Ag | |
| DE2460490A1 (de) * | 1974-12-20 | 1976-07-01 | Hoechst Ag | Wasserunloesliche disazomethinverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
-
1975
- 1975-04-09 DE DE2515523A patent/DE2515523C3/de not_active Expired
- 1975-12-16 US US05/641,252 patent/US4097510A/en not_active Expired - Lifetime
-
1976
- 1976-04-02 NL NL7603465A patent/NL7603465A/xx not_active Application Discontinuation
- 1976-04-06 BR BR7602069A patent/BR7602069A/pt unknown
- 1976-04-06 CH CH431376A patent/CH602889A5/xx not_active IP Right Cessation
- 1976-04-07 IT IT22067/76A patent/IT1058379B/it active
- 1976-04-07 IN IN609/CAL/76A patent/IN144446B/en unknown
- 1976-04-08 JP JP51038839A patent/JPS6043384B2/ja not_active Expired
- 1976-04-08 FR FR7610259A patent/FR2307021A1/fr active Granted
- 1976-04-08 AR AR262819A patent/AR224855A1/es active
- 1976-04-08 CA CA249,842A patent/CA1083590A/en not_active Expired
- 1976-04-08 AU AU12815/76A patent/AU1281576A/en not_active Expired
- 1976-04-09 GB GB14651/76A patent/GB1505009A/en not_active Expired
- 1976-04-09 BE BE166028A patent/BE840599A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU1281576A (en) | 1977-10-13 |
| DE2515523A1 (de) | 1976-10-28 |
| DE2515523C3 (de) | 1980-05-29 |
| US4097510A (en) | 1978-06-27 |
| BE840599A (fr) | 1976-10-11 |
| AR224855A1 (es) | 1982-01-29 |
| IN144446B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-05-06 |
| IT1058379B (it) | 1982-04-10 |
| NL7603465A (nl) | 1976-10-12 |
| FR2307021A1 (fr) | 1976-11-05 |
| FR2307021B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-02-15 |
| GB1505009A (en) | 1978-03-22 |
| JPS51123226A (en) | 1976-10-27 |
| CA1083590A (en) | 1980-08-12 |
| BR7602069A (pt) | 1976-10-05 |
| DE2515523B2 (de) | 1979-09-13 |
| CH602889A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-08-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3758497A (en) | The isoindoline series process for the production of deeply coloured transparent pigments of | |
| US4044036A (en) | Metal complexes of bis-azomethines from hydroxy-aldehydes and alkylene diamines | |
| US3687991A (en) | Azomethine metal complex dyes | |
| JPS6043384B2 (ja) | 水不溶性ジスアゾメチン化合物並びにその製法及び使用法 | |
| ITRM940786A1 (it) | "trifendiossazione per l'impiego come pigmenti" | |
| US3022298A (en) | Dioxazine dyestuffs | |
| US3622583A (en) | Yellow dyes of the phtalimidoquinophthalone series | |
| US3399191A (en) | Benzindole cyanotrimethine basic dyestuffs | |
| USRE27575E (en) | Water-insoluble benzimidazolone containing monoazo dyestuffs | |
| US3555003A (en) | Water-insoluble benzimidazolone containing monoazo dyestuffs | |
| US4097450A (en) | Perinone compounds as colorants for polyolefins | |
| US4042611A (en) | Water-in-soluble disazo methine compounds | |
| US3923774A (en) | Quinazolone containing phenyl-azo-pyridine compounds | |
| USRE25857E (en) | Water-insoluble benzeneazo-s-aceto- acetylaminobenzimidazolone dye- stuffs | |
| DE2451049A1 (de) | Perinon-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel | |
| US3555002A (en) | Water-insoluble benzimidazolone containing monoazo dyestuffs | |
| US2837528A (en) | Phthalocyanine pigments | |
| US2936305A (en) | Water-insoluble disazo dyestuffs | |
| US1881697A (en) | Manufacture of vat dyestuffs of the anthraquinone series | |
| US4157265A (en) | Water-insoluble disazomethine mixed metal-complex compounds, process for preparing them and their use as colorants | |
| US3657217A (en) | Monoazo dyes containing an indole | |
| US3715360A (en) | Dyes of the 2,4-dihydroxyquinoline series | |
| DE2446543A1 (de) | Wasserunloesliche monoazomethinfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung | |
| US3449425A (en) | N,n'-bis(beta-benzophenone)-arylenediamines | |
| JPS5828299B2 (ja) | ジスアゾカゴウブツ ノ セイホウ |