DE2534810A1 - Azopigmente und verfahren zu deren herstellung - Google Patents
Azopigmente und verfahren zu deren herstellungInfo
- Publication number
- DE2534810A1 DE2534810A1 DE19752534810 DE2534810A DE2534810A1 DE 2534810 A1 DE2534810 A1 DE 2534810A1 DE 19752534810 DE19752534810 DE 19752534810 DE 2534810 A DE2534810 A DE 2534810A DE 2534810 A1 DE2534810 A1 DE 2534810A1
- Authority
- DE
- Germany
- Prior art keywords
- pigment
- pigments
- yellow
- solution
- water
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 claims description 5
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000049 pigment Substances 0.000 description 55
- 239000001052 yellow pigment Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000975 dye Substances 0.000 description 14
- 238000005859 coupling reaction Methods 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 11
- 238000010168 coupling process Methods 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- 230000008878 coupling Effects 0.000 description 10
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 9
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical group [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 239000008199 coating composition Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 2
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- CFGFWEIWOCBBQR-UHFFFAOYSA-N 4-methyl-2-nitroaniline N-(2-methylphenyl)nitramide Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1.CC1=CC=CC=C1N[N+]([O-])=O CFGFWEIWOCBBQR-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 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 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical group ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-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
- 239000012860 organic pigment Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940052228 zinc oxide paste Drugs 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3665—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms
- C09B29/3669—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms from a pyrimidine ring
- C09B29/3673—Barbituric acid and derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/495,804 US3979377A (en) | 1974-08-08 | 1974-08-08 | Yellow azo pigment and process of preparation from dichloroaniline and barbituric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2534810A1 true DE2534810A1 (de) | 1976-02-19 |
Family
ID=23970046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752534810 Pending DE2534810A1 (de) | 1974-08-08 | 1975-08-05 | Azopigmente und verfahren zu deren herstellung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3979377A (enExample) |
| JP (1) | JPS5141024A (enExample) |
| BE (1) | BE832201A (enExample) |
| BR (1) | BR7505049A (enExample) |
| DE (1) | DE2534810A1 (enExample) |
| FR (1) | FR2281405A1 (enExample) |
| GB (1) | GB1461065A (enExample) |
| IT (1) | IT1040319B (enExample) |
| NL (1) | NL7509487A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5512347B2 (enExample) * | 1974-03-28 | 1980-04-01 | ||
| JPS5536009A (en) * | 1978-09-02 | 1980-03-13 | Yamaguchiken | Nozzle for carbonic acid gas shielded arc welding |
| JPH07331105A (ja) * | 1994-06-06 | 1995-12-19 | Dainichiseika Color & Chem Mfg Co Ltd | アゾ色素の製造方法 |
| CN112322068B (zh) * | 2020-11-27 | 2022-07-29 | 辽宁鸿港化工有限公司 | 一种单偶氮黄色有机颜料及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2140538A (en) * | 1937-01-14 | 1938-12-20 | Eastman Kodak Co | Coloration of organic derivatives of cellulose |
| US3654258A (en) * | 1969-08-27 | 1972-04-04 | Donald Edward Mckay | Disperse yellow dye of 5-(2-nitro-p-anisylazo) barbituric acid |
-
1974
- 1974-08-08 US US05/495,804 patent/US3979377A/en not_active Expired - Lifetime
-
1975
- 1975-08-01 IT IT26028/75A patent/IT1040319B/it active
- 1975-08-05 DE DE19752534810 patent/DE2534810A1/de active Pending
- 1975-08-06 FR FR7524526A patent/FR2281405A1/fr not_active Withdrawn
- 1975-08-06 GB GB3287775A patent/GB1461065A/en not_active Expired
- 1975-08-07 JP JP50095488A patent/JPS5141024A/ja active Pending
- 1975-08-07 BR BR7505049*A patent/BR7505049A/pt unknown
- 1975-08-07 BE BE159002A patent/BE832201A/xx unknown
- 1975-08-08 NL NL7509487A patent/NL7509487A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US3979377A (en) | 1976-09-07 |
| IT1040319B (it) | 1979-12-20 |
| BE832201A (fr) | 1976-02-09 |
| JPS5141024A (enExample) | 1976-04-06 |
| AU8371075A (en) | 1977-02-10 |
| FR2281405A1 (fr) | 1976-03-05 |
| BR7505049A (pt) | 1976-08-03 |
| GB1461065A (en) | 1977-01-13 |
| NL7509487A (nl) | 1976-02-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3305571C2 (enExample) | ||
| DE69809674T2 (de) | Gefärbtes, mit Titandioxid beschichtetes Glimmerpigment und damit beschichteter Gegenstand | |
| DE2215191A1 (de) | Verbesserte Pigmente | |
| DE2622902C2 (enExample) | ||
| DE69107106T2 (de) | Verfahren zur Herstellung von Pigmenten. | |
| DE2308594A1 (de) | Bisazomethinpigment und verfahren zu seiner herstellung | |
| DE2206551C3 (de) | Azofarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von Papier sowie naturlicher und regenerierter Cellulose | |
| DE2855944C3 (de) | Verfahren zur Herstellung von Pigmentzusammensetzungen | |
| DE2803990C2 (de) | Verfahren zur Herstellung von Azopigmenten | |
| DE2727531C2 (enExample) | ||
| DE2534810A1 (de) | Azopigmente und verfahren zu deren herstellung | |
| DE1254791B (de) | Anpastungsmittel fuer Pigmente | |
| DE1467473A1 (de) | Verfahren zur Herstellung eines modifizierten Farbpigments | |
| DE951524C (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE1769443C3 (de) | Azoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Druckfarben | |
| DE929992C (de) | Verfahren zur Herstellung von gefaerbtem Polyvinylbenzal | |
| DE927041C (de) | Verfahren zur Herstellung von Polyazofarbstoffen | |
| DE1928437A1 (de) | Neue Azoverbindungen und Verfahren zu deren Herstellung | |
| DE2330070C3 (de) | Mischpigment | |
| DE2133070A1 (de) | Azomethinpigmente und Verfahren zu ihrer Herstellung | |
| DE2012153C (de) | Verfahren zur Herstellung von Monoazopigmentgemischen sowie deren Verwendung zum Färben | |
| AT148467B (de) | Verfahren zur Herstellung gefärbter Lacke und filmbildender Überzüge. | |
| DE921532C (de) | Verfahren zur Herstellung von wasserunloeslichen Azofarbstoffen | |
| DE72387C (de) | Verfahren zur Darstellung von Lackfarben | |
| DE905659C (de) | UEberzugsmasse |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |