CH624977A5 - Process for the preparation of azo pigments - Google Patents
Process for the preparation of azo pigments Download PDFInfo
- Publication number
- CH624977A5 CH624977A5 CH1650576A CH1650576A CH624977A5 CH 624977 A5 CH624977 A5 CH 624977A5 CH 1650576 A CH1650576 A CH 1650576A CH 1650576 A CH1650576 A CH 1650576A CH 624977 A5 CH624977 A5 CH 624977A5
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- atoms
- methyl
- phenylenediamine
- amino
- Prior art date
Links
- 239000000049 pigment Substances 0.000 title description 17
- 238000000034 method Methods 0.000 title description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 239000000987 azo dye Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 15
- -1 carboxylic acid halide Chemical class 0.000 description 14
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 11
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 10
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- XKFIFYROMAAUDL-UHFFFAOYSA-N 3-amino-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1N XKFIFYROMAAUDL-UHFFFAOYSA-N 0.000 description 3
- 229940044174 4-phenylenediamine Drugs 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 3
- 125000005116 aryl carbamoyl group Chemical group 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000005236 alkanoylamino group Chemical group 0.000 description 2
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000005281 alkyl ureido group Chemical group 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 125000005239 aroylamino group Chemical group 0.000 description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- CPCPKQUNFFHAIZ-UHFFFAOYSA-N 2-chloro-5-methylbenzene-1,4-diamine Chemical compound CC1=CC(N)=C(Cl)C=C1N CPCPKQUNFFHAIZ-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 206010039587 Scarlet Fever Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- DGQLVPJVXFOQEV-JNVSTXMASA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-JNVSTXMASA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YEPWCJHMSVABPQ-UHFFFAOYSA-N methyl 3-amino-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(N)=C1 YEPWCJHMSVABPQ-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000002966 varnish 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
- C09B43/38—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines by reacting two or more ortho-hydroxy naphthoic acid dyes with polyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1650576A CH624977A5 (en) | 1976-12-31 | 1976-12-31 | Process for the preparation of azo pigments |
| GB5156977A GB1595489A (en) | 1976-12-31 | 1977-12-12 | Process for the production of azo pigments |
| JP15860177A JPS5385826A (en) | 1976-12-31 | 1977-12-27 | Disazo pigment* method of making same and process for coloring high molecular weight organic material using same |
| DE19772758407 DE2758407A1 (de) | 1976-12-31 | 1977-12-28 | Verfahren zur herstellung von azopigmenten |
| BR7708740A BR7708740A (pt) | 1976-12-31 | 1977-12-29 | Processo para a preparacao de azopigmentos,azopigmentos e sua aplicacao |
| FR7739621A FR2376190A1 (fr) | 1976-12-31 | 1977-12-29 | Procede de preparation de pigments azoiques |
| CA294,023A CA1095902A (en) | 1976-12-31 | 1977-12-29 | Process for the production of azo pigments |
| DK588677A DK588677A (da) | 1976-12-31 | 1977-12-30 | Fremgangsmaade til fremstilling af azopigmenter |
| IT3147477A IT1089279B (it) | 1976-12-31 | 1977-12-30 | Procedimento per la preparazione di pigmenti azoici |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1650576A CH624977A5 (en) | 1976-12-31 | 1976-12-31 | Process for the preparation of azo pigments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624977A5 true CH624977A5 (en) | 1981-08-31 |
Family
ID=4417944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1650576A CH624977A5 (en) | 1976-12-31 | 1976-12-31 | Process for the preparation of azo pigments |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5385826A (enrdf_load_stackoverflow) |
| BR (1) | BR7708740A (enrdf_load_stackoverflow) |
| CA (1) | CA1095902A (enrdf_load_stackoverflow) |
| CH (1) | CH624977A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2758407A1 (enrdf_load_stackoverflow) |
| DK (1) | DK588677A (enrdf_load_stackoverflow) |
| FR (1) | FR2376190A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1595489A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0594789U (ja) * | 1992-05-26 | 1993-12-24 | リズム時計工業株式会社 | カラクリ人形の動作機構 |
| EP0822235B1 (de) * | 1996-07-31 | 2002-01-30 | Ciba SC Holding AG | Verfahren zur Herstellung von farbstarken Disazopigmentgemischen |
| KR101428348B1 (ko) * | 2009-12-22 | 2014-08-11 | 다이니치 세이카 고교 가부시키가이샤 | 비대칭형 폴리아조 색소, 그 제조방법, 착색제 및 착색방법 |
| CN102816457B (zh) * | 2012-08-23 | 2013-12-11 | 鞍山七彩化学股份有限公司 | 一种高着色强度的红色偶氮缩合混合颜料及其制备方法 |
-
1976
- 1976-12-31 CH CH1650576A patent/CH624977A5/de not_active IP Right Cessation
-
1977
- 1977-12-12 GB GB5156977A patent/GB1595489A/en not_active Expired
- 1977-12-27 JP JP15860177A patent/JPS5385826A/ja active Granted
- 1977-12-28 DE DE19772758407 patent/DE2758407A1/de active Granted
- 1977-12-29 FR FR7739621A patent/FR2376190A1/fr active Granted
- 1977-12-29 CA CA294,023A patent/CA1095902A/en not_active Expired
- 1977-12-29 BR BR7708740A patent/BR7708740A/pt unknown
- 1977-12-30 DK DK588677A patent/DK588677A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1595489A (en) | 1981-08-12 |
| DE2758407A1 (de) | 1978-07-13 |
| JPS5385826A (en) | 1978-07-28 |
| CA1095902A (en) | 1981-02-17 |
| FR2376190A1 (fr) | 1978-07-28 |
| FR2376190B1 (enrdf_load_stackoverflow) | 1980-05-16 |
| DE2758407C2 (enrdf_load_stackoverflow) | 1987-07-23 |
| DK588677A (da) | 1978-07-01 |
| BR7708740A (pt) | 1978-08-22 |
| JPS6126591B2 (enrdf_load_stackoverflow) | 1986-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |