JP4070037B2 - 新規な結晶型のジケトピロロピロール顔料 - Google Patents
新規な結晶型のジケトピロロピロール顔料 Download PDFInfo
- Publication number
- JP4070037B2 JP4070037B2 JP22597397A JP22597397A JP4070037B2 JP 4070037 B2 JP4070037 B2 JP 4070037B2 JP 22597397 A JP22597397 A JP 22597397A JP 22597397 A JP22597397 A JP 22597397A JP 4070037 B2 JP4070037 B2 JP 4070037B2
- Authority
- JP
- Japan
- Prior art keywords
- diketopyrrolopyrrole
- pigment
- formula
- succinate
- alkali metal
- 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 - Fee Related
Links
- 239000000049 pigment Substances 0.000 title claims description 33
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 title claims description 18
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- -1 alkali metal salt Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000003900 succinic acid esters Chemical group 0.000 claims description 4
- 230000003750 conditioning effect Effects 0.000 claims description 3
- 238000007796 conventional method Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- QPULDJYQYDGZEI-AATRIKPKSA-N Trans-4-Nonenal Chemical compound CCCC\C=C\CCC=O QPULDJYQYDGZEI-AATRIKPKSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001143 conditioned effect Effects 0.000 claims 1
- 238000010586 diagram Methods 0.000 abstract description 2
- 238000012986 modification Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000003973 paint Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 229920003264 Maprenal® Polymers 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 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 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- IGPFDBHTWKTPFD-UHFFFAOYSA-N 1,4-diphenylpyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C=1C=CC=CC=1C1=NC(=O)C2=C1C(=O)N=C2C1=CC=CC=C1 IGPFDBHTWKTPFD-UHFFFAOYSA-N 0.000 description 1
- SJIQTGOBEGYKSI-UHFFFAOYSA-N 2-[(1,3-dioxoisoindol-2-yl)methyl]-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC=C(NC=2C(=CC3=C(C(C4=CC=CC=C4N3)=O)C=2)C2=O)C2=C1 SJIQTGOBEGYKSI-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole 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
- 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
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/003—Crystal modifications; Special X-ray patterns of diketopyrrolopyrrole
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Optical Filters (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2060/96 | 1996-08-22 | ||
| CH206096 | 1996-08-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH10101960A JPH10101960A (ja) | 1998-04-21 |
| JPH10101960A5 JPH10101960A5 (enExample) | 2005-05-26 |
| JP4070037B2 true JP4070037B2 (ja) | 2008-04-02 |
Family
ID=4224982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22597397A Expired - Fee Related JP4070037B2 (ja) | 1996-08-22 | 1997-08-22 | 新規な結晶型のジケトピロロピロール顔料 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5871575A (enExample) |
| EP (1) | EP0825234B1 (enExample) |
| JP (1) | JP4070037B2 (enExample) |
| KR (1) | KR100503583B1 (enExample) |
| CN (1) | CN1057526C (enExample) |
| AT (1) | ATE201710T1 (enExample) |
| BR (1) | BR9704479A (enExample) |
| CA (1) | CA2213440A1 (enExample) |
| CZ (1) | CZ290763B6 (enExample) |
| DE (1) | DE59703652D1 (enExample) |
| TW (1) | TW457280B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59804631D1 (de) * | 1997-05-06 | 2002-08-08 | Ciba Sc Holding Ag | Diketopyrrolopyrrolzusammensetzungen |
| EP0952183B1 (de) * | 1998-04-22 | 2005-02-23 | Ciba SC Holding AG | Verzugsfreie Pigmentzusammensetzungen enthaltend Diaryl-diketopyrrolo 3,4c pyrrole |
| US6057449A (en) * | 1998-06-02 | 2000-05-02 | Ciba Specialty Chemicals Corporation | Direct preparation of pyrrolo[3,4-c]pyrroles |
| US6375732B1 (en) | 1999-04-08 | 2002-04-23 | Clariant Finance (Bvi) Limited | Pigments, the process of their manufacturing and their use |
| DE10028104A1 (de) | 2000-06-07 | 2001-12-13 | Clariant Gmbh | Verfahren zur Herstellung von Diketopyrrologyrrol-Pigmenten |
| KR20050103950A (ko) * | 2003-02-20 | 2005-11-01 | 시바 스페셜티 케미칼스 홀딩 인크. | 내부 교반 안료 조성물 |
| JP5082318B2 (ja) * | 2006-07-24 | 2012-11-28 | 東洋インキＳｃホールディングス株式会社 | α型結晶変態ジクロロジケトピロロピロール顔料の製造方法、該方法で製造されたα型結晶変態ジクロロジケトピロロピロール顔料、およびそれを用いた着色組成物 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0061426B1 (de) * | 1981-03-20 | 1985-02-13 | Ciba-Geigy Ag | Verfahren zum Färben von hochmolekularem organischem Material und neue polycyclische Pigmente |
| DE3366011D1 (en) * | 1982-05-17 | 1986-10-16 | Ciba Geigy Ag | Preparation of pyrrolo-(3,4-c) pyrroles |
| US4783540A (en) * | 1986-08-07 | 1988-11-08 | Ciba-Geigy Corporation | Solid solutions of pyrrolo-(3,4-C)-pyrrols |
| WO1990001480A1 (de) * | 1988-07-29 | 1990-02-22 | Riedel-De Haen Aktiengesellschaft | Optische datenspeicher |
| EP0408498B1 (de) * | 1989-07-13 | 1994-09-14 | Ciba-Geigy Ag | Plättchenförmige organische Effektpigmente |
| US5347014A (en) * | 1992-12-23 | 1994-09-13 | Ciba-Geigy Corporation | Process for preparing 1,4-diketo-3,6-diphenylpyrrolo-[3,4-C]-pyrrole |
| TW372244B (en) * | 1993-07-29 | 1999-10-21 | Ciba Sc Holding Ag | Process for producing novel finely divided highly transparent diketopyrrolopyrrole pigments |
| EP0648770B1 (de) * | 1993-10-13 | 2000-05-17 | Ciba SC Holding AG | Pyrrolo[3,4-c]pyrrole |
| EP0654506B1 (de) * | 1993-11-22 | 2000-05-17 | Ciba SC Holding AG | Verfahren zur Herstellung synergistischer Pigmentgemische |
| EP0690059B1 (de) * | 1994-06-29 | 1999-09-08 | Ciba SC Holding AG | Zwei neue Kristallmodifikationen eines Diketopyrrolopyrrolpigments |
| EP0690057B1 (de) * | 1994-06-29 | 1999-09-08 | Ciba SC Holding AG | Neue Kristallmodifikation eines Diketopyrrolopyrrolpigments |
| DE59506763D1 (de) * | 1994-06-29 | 1999-10-14 | Ciba Sc Holding Ag | Neue Kristallmodifikation eines Diketopyrrolopyrrolpigments |
| DE59507427D1 (de) * | 1994-09-28 | 2000-01-20 | Ciba Sc Holding Ag | Mischkristalle und feste Lösungen von 1,4-Diketopyrrolopyrrolen |
| KR100307444B1 (ko) * | 1994-10-12 | 2001-12-01 | 김순택 | 면광원장치 |
| EP0748851B1 (de) * | 1995-06-15 | 2001-05-09 | Ciba SC Holding AG | Pigmentzusammensetzungen aus Diketopyrrolopyrrolen |
-
1997
- 1997-08-13 EP EP97810564A patent/EP0825234B1/de not_active Expired - Lifetime
- 1997-08-13 AT AT97810564T patent/ATE201710T1/de not_active IP Right Cessation
- 1997-08-13 DE DE59703652T patent/DE59703652D1/de not_active Expired - Lifetime
- 1997-08-18 CN CN97117830A patent/CN1057526C/zh not_active Expired - Fee Related
- 1997-08-20 TW TW086111896A patent/TW457280B/zh not_active IP Right Cessation
- 1997-08-20 CA CA002213440A patent/CA2213440A1/en not_active Abandoned
- 1997-08-20 CZ CZ19972660A patent/CZ290763B6/cs not_active IP Right Cessation
- 1997-08-21 BR BR9704479A patent/BR9704479A/pt not_active Application Discontinuation
- 1997-08-21 KR KR1019970039788A patent/KR100503583B1/ko not_active Expired - Fee Related
- 1997-08-22 US US08/916,659 patent/US5871575A/en not_active Expired - Lifetime
- 1997-08-22 JP JP22597397A patent/JP4070037B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE201710T1 (de) | 2001-06-15 |
| CN1174840A (zh) | 1998-03-04 |
| US5871575A (en) | 1999-02-16 |
| KR19980018836A (ko) | 1998-06-05 |
| EP0825234B1 (de) | 2001-05-30 |
| BR9704479A (pt) | 1998-12-15 |
| CA2213440A1 (en) | 1998-02-22 |
| TW457280B (en) | 2001-10-01 |
| EP0825234A2 (de) | 1998-02-25 |
| CZ290763B6 (cs) | 2002-10-16 |
| DE59703652D1 (de) | 2001-07-05 |
| CN1057526C (zh) | 2000-10-18 |
| JPH10101960A (ja) | 1998-04-21 |
| KR100503583B1 (ko) | 2005-10-21 |
| CZ266097A3 (cs) | 1998-03-18 |
| EP0825234A3 (de) | 1998-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3135977B2 (ja) | 新規なジケトピロロピロール | |
| CA1311092C (en) | Compositions based on indanthrone blue pigments | |
| US4069064A (en) | Phthalocyanine formulations having high gloss, which are stabilized against recrystallization and against change of modification | |
| GB2238550A (en) | New diketopyrrolopyrrole pigment mixtures comprising both sulfonated and unsulfonated components | |
| JP3927258B2 (ja) | ジケトピロロピロールの顔料組成物 | |
| JPH08199085A (ja) | １、４−ジケトピロロピロールの混晶および固溶体 | |
| KR100435007B1 (ko) | 1,4-디케토피롤로피롤및퀴나크리돈의3성분고용체 | |
| JP2573642B2 (ja) | ピロロ−〔３，４−ｃ〕−ピロールとキナクリドンとの固溶体 | |
| US5650520A (en) | Crystal modification of a diketopyrrolopyrrole pigment | |
| JP4410321B2 (ja) | 新規なジケトピロロピロール組成物 | |
| JP2537932B2 (ja) | Ｃ．ｉ．ピグメントレッド１７７を基剤とした新規組成物 | |
| JP4070037B2 (ja) | 新規な結晶型のジケトピロロピロール顔料 | |
| JP3881388B2 (ja) | 高度なクロマを有するジケトピロロピロール顔料 | |
| JPH08120189A (ja) | ジアリールジケトピロロピロール顔料の製造方法 | |
| EP0690059B1 (de) | Zwei neue Kristallmodifikationen eines Diketopyrrolopyrrolpigments | |
| JPH07110923B2 (ja) | 顔料組成物及び顔料分散体 | |
| US6616750B2 (en) | Ternary pigment compositions | |
| EP0690057A1 (de) | Neue Kristallmodifikation eines Diketopyrrolopyrrolpigments | |
| MXPA97006385A (en) | Azinyloxy, and phenoxy-diaryl-carboxylic acid derivatives, their preparation and use as mixed eta | |
| US4725685A (en) | Novel isoindoline compounds, their metal complexes and their use as pigments | |
| US20070226920A1 (en) | Salts of Laked Monoazo Compounds | |
| JPH06322282A (ja) | ピロロピロール顔料の安定化 | |
| MXPA98003569A (en) | Compositions of diceto pirrolo pirrol novedo |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20040727 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20040727 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20070423 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A132 Effective date: 20070501 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20070731 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20070803 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20070831 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20070905 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20071001 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20071004 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20071116 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20080110 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110125 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110125 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120125 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120125 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130125 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140125 Year of fee payment: 6 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |