DE2223791A1 - Verfahren zur Herstellung von Dichlorchinacridonen - Google Patents
Verfahren zur Herstellung von DichlorchinacridonenInfo
- Publication number
- DE2223791A1 DE2223791A1 DE19722223791 DE2223791A DE2223791A1 DE 2223791 A1 DE2223791 A1 DE 2223791A1 DE 19722223791 DE19722223791 DE 19722223791 DE 2223791 A DE2223791 A DE 2223791A DE 2223791 A1 DE2223791 A1 DE 2223791A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfuric acid
- parts
- percent
- mixture
- acid
- 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 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 239000000049 pigment Substances 0.000 description 13
- 238000006798 ring closing metathesis reaction Methods 0.000 description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000004040 coloring Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- -1 1 -chlorphenylamino Chemical group 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JMEWGCRUPXQFQL-UHFFFAOYSA-N 1,2-dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1Cl)Cl)N1)C1=C2 JMEWGCRUPXQFQL-UHFFFAOYSA-N 0.000 description 2
- JCHNWGHDRJBSRH-UHFFFAOYSA-N 2,5-bis(3-chloroanilino)terephthalic acid Chemical compound OC(=O)C=1C=C(NC=2C=C(Cl)C=CC=2)C(C(=O)O)=CC=1NC1=CC=CC(Cl)=C1 JCHNWGHDRJBSRH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 230000019612 pigmentation Effects 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- ZJQZWNLKRBUEKX-UHFFFAOYSA-N 2,5-dianilinoterephthalic acid Chemical class OC(=O)C=1C=C(NC=2C=CC=CC=2)C(C(=O)O)=CC=1NC1=CC=CC=C1 ZJQZWNLKRBUEKX-UHFFFAOYSA-N 0.000 description 1
- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000137 polyphosphoric acid 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
- 230000000750 progressive effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C09B48/00—Quinacridones
-
- 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
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0036—Mixtures of quinacridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Printing Methods (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH744571A CH543571A (de) | 1971-05-19 | 1971-05-19 | Verfahren zur Herstellung von 3,10-Dichlorchinacridon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2223791A1 true DE2223791A1 (de) | 1972-12-07 |
Family
ID=4325235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722223791 Pending DE2223791A1 (de) | 1971-05-19 | 1972-05-16 | Verfahren zur Herstellung von Dichlorchinacridonen |
Country Status (13)
| Country | Link |
|---|---|
| AU (1) | AU476824B2 (enExample) |
| BE (1) | BE783626A (enExample) |
| BR (2) | BR7201557D0 (enExample) |
| CA (1) | CA999865A (enExample) |
| CH (1) | CH543571A (enExample) |
| DD (1) | DD96717A5 (enExample) |
| DE (1) | DE2223791A1 (enExample) |
| ES (1) | ES402824A1 (enExample) |
| FR (1) | FR2137546B1 (enExample) |
| GB (1) | GB1390093A (enExample) |
| IT (1) | IT955635B (enExample) |
| NL (1) | NL7206457A (enExample) |
| SU (1) | SU424354A3 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5927800B2 (ja) * | 1977-02-25 | 1984-07-07 | 花王株式会社 | スコアリングパツド |
| GB9704665D0 (en) * | 1997-03-06 | 1997-04-23 | Clariant Int Ltd | Organic compounds |
| CN100513491C (zh) * | 2003-07-18 | 2009-07-15 | 西巴特殊化学品控股有限公司 | 包括不对称取代的组分的喹吖啶酮颜料组合物 |
| BRPI0412754A (pt) * | 2003-07-18 | 2006-09-26 | Ciba Sc Holding Ag | composições de pigmentos de quinacridona, que compreendem componentes substituìdos assimetricamente |
-
1971
- 1971-05-19 CH CH744571A patent/CH543571A/de not_active IP Right Cessation
-
1972
- 1972-03-17 BR BR155772A patent/BR7201557D0/pt unknown
- 1972-05-05 FR FR7216040A patent/FR2137546B1/fr not_active Expired
- 1972-05-12 NL NL7206457A patent/NL7206457A/xx not_active Application Discontinuation
- 1972-05-16 DE DE19722223791 patent/DE2223791A1/de active Pending
- 1972-05-16 GB GB2287272A patent/GB1390093A/en not_active Expired
- 1972-05-17 BR BR313372A patent/BR7203133D0/pt unknown
- 1972-05-17 ES ES402824A patent/ES402824A1/es not_active Expired
- 1972-05-17 SU SU1784786A patent/SU424354A3/ru active
- 1972-05-17 BE BE783626A patent/BE783626A/xx unknown
- 1972-05-18 CA CA142,461A patent/CA999865A/en not_active Expired
- 1972-05-18 IT IT2453372A patent/IT955635B/it active
- 1972-05-18 AU AU42463/72A patent/AU476824B2/en not_active Expired
- 1972-05-18 DD DD16306872A patent/DD96717A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2137546B1 (enExample) | 1978-03-03 |
| IT955635B (it) | 1973-09-29 |
| BR7201557D0 (pt) | 1973-05-17 |
| SU424354A3 (ru) | 1974-04-15 |
| NL7206457A (enExample) | 1972-11-21 |
| AU476824B2 (en) | 1976-10-07 |
| AU4246372A (en) | 1973-11-22 |
| CH543571A (de) | 1973-10-31 |
| BR7203133D0 (pt) | 1973-09-25 |
| ES402824A1 (es) | 1975-11-01 |
| CA999865A (en) | 1976-11-16 |
| FR2137546A1 (enExample) | 1972-12-29 |
| GB1390093A (en) | 1975-04-09 |
| BE783626A (fr) | 1972-11-17 |
| DD96717A5 (enExample) | 1973-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OD | Request for examination | ||
| OHN | Withdrawal |