JPH0796652B2 - テトラクロロペリレン―３，４，９，１０―テトラカルボン酸ジイミド顔料及びラッカー、合成樹脂又は印刷インキの着色法 - Google Patents
テトラクロロペリレン―３，４，９，１０―テトラカルボン酸ジイミド顔料及びラッカー、合成樹脂又は印刷インキの着色法Info
- Publication number
- JPH0796652B2 JPH0796652B2 JP62225466A JP22546687A JPH0796652B2 JP H0796652 B2 JPH0796652 B2 JP H0796652B2 JP 62225466 A JP62225466 A JP 62225466A JP 22546687 A JP22546687 A JP 22546687A JP H0796652 B2 JPH0796652 B2 JP H0796652B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- weight
- tetracarboxylic acid
- tetrachloroperylene
- acid diimide
- 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 - Lifetime
Links
- 239000000049 pigment Substances 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 13
- 238000004040 coloring Methods 0.000 title claims description 10
- 239000004922 lacquer Substances 0.000 title claims description 7
- 229920003002 synthetic resin Polymers 0.000 title claims 2
- 239000000057 synthetic resin Substances 0.000 title claims 2
- UXOABCSWTQUWSB-UHFFFAOYSA-N ClC=1C(=C(C2=C(C(=C(C=3C4=CC=C(C=5C(=CC=C(C1C23)C54)C(=O)O)C(=O)O)Cl)Cl)C(O)=N)C(O)=N)Cl Chemical compound ClC=1C(=C(C2=C(C(=C(C=3C4=CC=C(C=5C(=CC=C(C1C23)C54)C(=O)O)C(=O)O)Cl)Cl)C(O)=N)C(O)=N)Cl UXOABCSWTQUWSB-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000002245 particle Substances 0.000 claims description 15
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 9
- 229910000071 diazene Inorganic materials 0.000 claims description 8
- 238000001228 spectrum Methods 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- MZZSDCJQCLYLLL-UHFFFAOYSA-N Secalonsaeure A Natural products COC(=O)C12OC3C(CC1=C(O)CC(C)C2O)C(=CC=C3c4ccc(O)c5C(=O)C6=C(O)CC(C)C(O)C6(Oc45)C(=O)OC)O MZZSDCJQCLYLLL-UHFFFAOYSA-N 0.000 claims 1
- 239000000976 ink Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 21
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 238000005660 chlorination reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000012986 modification Methods 0.000 description 10
- 235000009518 sodium iodide Nutrition 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- -1 aromatic iodine compounds Chemical class 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- RPQOZSKWYNULKS-UHFFFAOYSA-N 1,2-dicarbamoylperylene-3,4-dicarboxylic acid Chemical class C1=C(C(O)=O)C2=C(C(O)=O)C(C(=N)O)=C(C(O)=N)C(C=3C4=C5C=CC=C4C=CC=3)=C2C5=C1 RPQOZSKWYNULKS-UHFFFAOYSA-N 0.000 description 4
- PONZBUKBFVIXOD-UHFFFAOYSA-N 9,10-dicarbamoylperylene-3,4-dicarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=N)C2=C1C3=CC=C2C(=N)O PONZBUKBFVIXOD-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 229920000180 alkyd Polymers 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004640 Melamine resin Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000008096 xylene Substances 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
- BJQHLKABXJIVAM-BGYRXZFFSA-N 1-o-[(2r)-2-ethylhexyl] 2-o-[(2s)-2-ethylhexyl] benzene-1,2-dicarboxylate Chemical compound CCCC[C@H](CC)COC(=O)C1=CC=CC=C1C(=O)OC[C@H](CC)CCCC BJQHLKABXJIVAM-BGYRXZFFSA-N 0.000 description 1
- BASXRUDJZCJPHE-UHFFFAOYSA-N 2,3,4,5-tetrachloroperylene-1-carboxylic acid Chemical compound C1=CC(C=2C(C(=O)O)=C(Cl)C(Cl)=C3C=2C2=CC(Cl)=C3Cl)=C3C2=CC=CC3=C1 BASXRUDJZCJPHE-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GRDAXMZKXYXRCK-UHFFFAOYSA-N C1=C(Cl)C(C2=C3C(=C(C(O)=O)C(C2(Cl)C(O)=N)C(=N)O)C(=CC(Cl)=C32)C(O)=O)=C3C2=C(Cl)C=CC3=C1 Chemical compound C1=C(Cl)C(C2=C3C(=C(C(O)=O)C(C2(Cl)C(O)=N)C(=N)O)C(=CC(Cl)=C32)C(O)=O)=C3C2=C(Cl)C=CC3=C1 GRDAXMZKXYXRCK-UHFFFAOYSA-N 0.000 description 1
- PNMOTPYDEOUYDA-UHFFFAOYSA-N ClC1=C(C(O)=O)C2=C(C(O)=O)C(C(=N)O)=C(C(O)=N)C(C=3C4=C5C(Cl)=C(Cl)C=C4C=CC=3)=C2C5=C1Cl Chemical compound ClC1=C(C(O)=O)C2=C(C(O)=O)C(C(=N)O)=C(C(O)=N)C(C=3C4=C5C(Cl)=C(Cl)C=C4C=CC=3)=C2C5=C1Cl PNMOTPYDEOUYDA-UHFFFAOYSA-N 0.000 description 1
- LRIQOJVVWGKNOF-UHFFFAOYSA-N ClC1=C(C2=C(C(=C(C=3C=4C=CC=C5C=CC=C(C(=C1)C23)C54)C(O)=N)C(O)=N)C(=O)O)C(=O)O Chemical compound ClC1=C(C2=C(C(=C(C=3C=4C=CC=C5C=CC=C(C(=C1)C23)C54)C(O)=N)C(O)=N)C(=O)O)C(=O)O LRIQOJVVWGKNOF-UHFFFAOYSA-N 0.000 description 1
- YOOKIZGXLNHXTR-UHFFFAOYSA-N ClC1=CC=2C3=CC(=C(C=4C(=C(C=C(C5=CC(=C(C(=C1C(O)=N)C52)C(O)=N)Cl)C43)Cl)C(=O)O)C(=O)O)Cl Chemical class ClC1=CC=2C3=CC(=C(C=4C(=C(C=C(C5=CC(=C(C(=C1C(O)=N)C52)C(O)=N)Cl)C43)Cl)C(=O)O)C(=O)O)Cl YOOKIZGXLNHXTR-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N Diethylhexyl phthalate Natural products CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 208000032400 Retinal pigmentation Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000009500 colour coating Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- QCHIESZMDORMPC-UHFFFAOYSA-N dibutyltin;hexyl 2-hydroxyethanedithioate Chemical compound CCCC[Sn]CCCC.CCCCCCSC(=S)CO QCHIESZMDORMPC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 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
- 125000005462 imide group Chemical group 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000000984 vat dye Substances 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Optical Filters (AREA)
- Developing Agents For Electrophotography (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863631678 DE3631678A1 (de) | 1986-09-18 | 1986-09-18 | Tetrachlorperylen-3,4,9,10-tetracarbonsaeurediimidpigment und dessen verwendung |
| DE3631678.4 | 1986-09-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6377976A JPS6377976A (ja) | 1988-04-08 |
| JPH0796652B2 true JPH0796652B2 (ja) | 1995-10-18 |
Family
ID=6309790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62225466A Expired - Lifetime JPH0796652B2 (ja) | 1986-09-18 | 1987-09-10 | テトラクロロペリレン―３，４，９，１０―テトラカルボン酸ジイミド顔料及びラッカー、合成樹脂又は印刷インキの着色法 |
Country Status (4)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3836536A1 (de) * | 1988-10-27 | 1990-05-10 | Hoechst Ag | Mischkristallpigmente auf basis halogenierter perylentetracarbonsaeurediimide |
| DE3926563A1 (de) * | 1989-08-11 | 1991-02-14 | Hoechst Ag | Sulfonsaeuregruppenhaltige perylenverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| US5986099A (en) * | 1995-01-20 | 1999-11-16 | Basf Aktiengesellschaft | Substituted quaterrylene tetracarboxylic acid diimides |
| DE10005186A1 (de) | 2000-02-05 | 2001-08-09 | Clariant Gmbh | Verfahren zur Herstellung von Perylen-3,4,9,10-tetracarbonsäurediimid in transparenter Pigmentform |
| DE10307557A1 (de) * | 2003-02-21 | 2004-09-02 | Clariant Gmbh | Verfahren zur Herstellung von transparenten Pigmentzubereitungen auf Basis von Perylen-3,4,9,10-tetracarbonsäurediimid |
| EP1749316B1 (en) | 2004-01-26 | 2016-06-29 | Northwestern University | Perylene n-type semiconductors and related devices |
| WO2007146250A2 (en) * | 2006-06-12 | 2007-12-21 | Northwestern University | Naphthalene-based semiconductor materials and methods of preparing and use thereof |
| WO2008051552A2 (en) * | 2006-10-25 | 2008-05-02 | Northwestern University | Organic semiconductor materials and methods of preparing and use thereof |
| EP2086974B1 (en) * | 2006-11-17 | 2013-07-24 | Polyera Corporation | Diimide-based semiconductor materials and methods of preparing and using the same |
| EP2104676A2 (en) * | 2007-01-08 | 2009-09-30 | Polyera Corporation | Methods for preparing arene-bis(dicarboximide)-based semiconducting materials and related intermediates for preparing same |
| US8022214B2 (en) * | 2007-01-24 | 2011-09-20 | Polyera Corporation | Organic semiconductor materials and precursors thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE441587C (de) * | 1922-10-27 | 1927-03-03 | Kalle & Co Akt Ges | Verfahren zur Darstellung von Halogenisierungsprodukten des Perylentetracarbonsaeureimids und seiner Derivate |
| DE2519720A1 (de) * | 1975-05-02 | 1976-11-11 | Dynamit Nobel Ag | Ketogruppen enthaltende ungesaettigte siliciumorganische verbindungen |
| DE3018006A1 (de) * | 1980-05-10 | 1981-11-12 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von pigmenten der perylen-3,4,9,10-tetracarbonsaeurediimidreihe und ihre verwendung |
| DE3149620A1 (de) * | 1981-12-15 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | Lichtsammelsysteme unter verwendung von halogenierten perylenderivaten als lichtwandler |
-
1986
- 1986-09-18 DE DE19863631678 patent/DE3631678A1/de active Granted
-
1987
- 1987-09-03 US US07/092,600 patent/US4846892A/en not_active Expired - Fee Related
- 1987-09-10 JP JP62225466A patent/JPH0796652B2/ja not_active Expired - Lifetime
- 1987-09-15 DE DE87113439T patent/DE3788325D1/de not_active Expired - Lifetime
- 1987-09-15 EP EP87113439A patent/EP0260648B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0260648A3 (de) | 1991-09-04 |
| US4846892A (en) | 1989-07-11 |
| DE3631678C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-28 |
| JPS6377976A (ja) | 1988-04-08 |
| DE3631678A1 (de) | 1988-03-24 |
| EP0260648B1 (de) | 1993-12-01 |
| DE3788325D1 (de) | 1994-01-13 |
| EP0260648A2 (de) | 1988-03-23 |
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