DE2017450C3 - Farbstoffe der Pyranthronreihe und Verfahren zu ihrer Herstellung - Google Patents
Farbstoffe der Pyranthronreihe und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2017450C3 DE2017450C3 DE2017450A DE2017450A DE2017450C3 DE 2017450 C3 DE2017450 C3 DE 2017450C3 DE 2017450 A DE2017450 A DE 2017450A DE 2017450 A DE2017450 A DE 2017450A DE 2017450 C3 DE2017450 C3 DE 2017450C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- bromine
- dye
- good
- dyes
- 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
- 239000000975 dye Substances 0.000 title claims description 46
- 238000000034 method Methods 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 4
- XQGDNRFLRLSUFQ-UHFFFAOYSA-N 2H-pyranthren-1-one Chemical class C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 XQGDNRFLRLSUFQ-UHFFFAOYSA-N 0.000 title description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 25
- 229910052794 bromium Inorganic materials 0.000 description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 12
- KEENQJKVECTQBT-UHFFFAOYSA-N 6,14-dichloro-2H-pyranthren-1-one Chemical compound C12=C3C4=C5C6=CC3=C(Cl)C=C2C=C2C=CC=CC2=C1C=C4C(Cl)=CC5=CC1=C6C=CCC1=O KEENQJKVECTQBT-UHFFFAOYSA-N 0.000 description 11
- 230000031709 bromination Effects 0.000 description 10
- 238000005893 bromination reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000049 pigment Substances 0.000 description 8
- 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 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000001054 red pigment Substances 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 239000001053 orange pigment Substances 0.000 description 5
- 239000000984 vat dye Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- -1 bromine 6,14-dichloropyranthrone Chemical compound 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IOPYVZVNUXHZCP-UHFFFAOYSA-N 2-(3-ethyloctan-3-yloxycarbonyl)benzoic acid Chemical compound CCCCCC(CC)(CC)OC(=O)C1=CC=CC=C1C(O)=O IOPYVZVNUXHZCP-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- YOCIQNIEQYCORH-UHFFFAOYSA-M chembl2028361 Chemical compound [Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 YOCIQNIEQYCORH-UHFFFAOYSA-M 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical group Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000554155 Andes Species 0.000 description 1
- 235000010469 Glycine max Nutrition 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
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XWTFVTOZYCMQLA-UHFFFAOYSA-N [S].[Br] Chemical compound [S].[Br] XWTFVTOZYCMQLA-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene 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
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical class C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010626 work up procedure 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/40—Pyranthrones
- C09B3/44—Preparation from starting materials already containing the pyranthrone nucleus
- C09B3/46—Preparation from starting materials already containing the pyranthrone nucleus by halogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Paints Or Removers (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2017450A DE2017450C3 (de) | 1970-04-11 | 1970-04-11 | Farbstoffe der Pyranthronreihe und Verfahren zu ihrer Herstellung |
| CA109,807A CA945547A (en) | 1970-04-11 | 1971-04-05 | Dyes of the pyranthrone series |
| US00131402A US3754008A (en) | 1970-04-11 | 1971-04-05 | Dyes of the pyranthrone series |
| NL7104694A NL7104694A (enExample) | 1970-04-11 | 1971-04-07 | |
| CH508471A CH533154A (de) | 1970-04-11 | 1971-04-07 | Verfahren zur Herstellung von Farbstoffen der Pyranthronreihe |
| FR7112821A FR2086001B1 (enExample) | 1970-04-11 | 1971-04-09 | |
| JP46022363A JPS5215612B1 (enExample) | 1970-04-11 | 1971-04-12 | |
| GB2656171*A GB1340530A (en) | 1970-04-11 | 1971-04-19 | Dyes of the pyranthrone series preparation of substituted chromenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2017450A DE2017450C3 (de) | 1970-04-11 | 1970-04-11 | Farbstoffe der Pyranthronreihe und Verfahren zu ihrer Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2017450A1 DE2017450A1 (enExample) | 1971-11-04 |
| DE2017450B2 DE2017450B2 (de) | 1974-12-05 |
| DE2017450C3 true DE2017450C3 (de) | 1975-07-10 |
Family
ID=5767842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2017450A Expired DE2017450C3 (de) | 1970-04-11 | 1970-04-11 | Farbstoffe der Pyranthronreihe und Verfahren zu ihrer Herstellung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3754008A (enExample) |
| JP (1) | JPS5215612B1 (enExample) |
| CA (1) | CA945547A (enExample) |
| CH (1) | CH533154A (enExample) |
| DE (1) | DE2017450C3 (enExample) |
| FR (1) | FR2086001B1 (enExample) |
| GB (1) | GB1340530A (enExample) |
| NL (1) | NL7104694A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3814246A1 (de) * | 1988-04-27 | 1989-11-09 | Siemens Ag | Medizinische untersuchungsanlage mit einer bilderzeugungsvorrichtung |
-
1970
- 1970-04-11 DE DE2017450A patent/DE2017450C3/de not_active Expired
-
1971
- 1971-04-05 US US00131402A patent/US3754008A/en not_active Expired - Lifetime
- 1971-04-05 CA CA109,807A patent/CA945547A/en not_active Expired
- 1971-04-07 CH CH508471A patent/CH533154A/de not_active IP Right Cessation
- 1971-04-07 NL NL7104694A patent/NL7104694A/xx unknown
- 1971-04-09 FR FR7112821A patent/FR2086001B1/fr not_active Expired
- 1971-04-12 JP JP46022363A patent/JPS5215612B1/ja active Pending
- 1971-04-19 GB GB2656171*A patent/GB1340530A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA945547A (en) | 1974-04-16 |
| NL7104694A (enExample) | 1971-10-13 |
| JPS5215612B1 (enExample) | 1977-05-02 |
| GB1340530A (en) | 1973-12-12 |
| FR2086001B1 (enExample) | 1975-09-26 |
| DE2017450A1 (enExample) | 1971-11-04 |
| US3754008A (en) | 1973-08-21 |
| DE2017450B2 (de) | 1974-12-05 |
| FR2086001A1 (enExample) | 1971-12-31 |
| CH533154A (de) | 1973-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8330 | Complete disclaimer |