DE19900063A1 - Naphthalin- und Perylenhydrazamimide - eine neue Klasse von Farbstoffen - Google Patents
Naphthalin- und Perylenhydrazamimide - eine neue Klasse von FarbstoffenInfo
- Publication number
- DE19900063A1 DE19900063A1 DE19900063A DE19900063A DE19900063A1 DE 19900063 A1 DE19900063 A1 DE 19900063A1 DE 19900063 A DE19900063 A DE 19900063A DE 19900063 A DE19900063 A DE 19900063A DE 19900063 A1 DE19900063 A1 DE 19900063A1
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- groups
- naphthalene
- preferred
- perylene
- 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.)
- Withdrawn
Links
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title claims abstract description 187
- 239000000975 dye Substances 0.000 title claims abstract description 143
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title claims abstract description 64
- -1 1,2-disubstituted hydrazines Chemical class 0.000 claims abstract description 229
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 41
- 239000000049 pigment Substances 0.000 claims abstract description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000000047 product Substances 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 150000002429 hydrazines Chemical class 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 claims description 20
- 230000015572 biosynthetic process Effects 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 19
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 14
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 12
- 239000003086 colorant Substances 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
- 239000003973 paint Substances 0.000 claims description 12
- 238000003786 synthesis reaction Methods 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 239000000976 ink Substances 0.000 claims description 10
- 238000004040 coloring Methods 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000000123 paper Substances 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 239000004065 semiconductor Substances 0.000 claims description 8
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000003136 n-heptyl 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])* 0.000 claims description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 229920000297 Rayon Polymers 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 230000003993 interaction Effects 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 238000010422 painting Methods 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- 238000007639 printing Methods 0.000 claims description 4
- 238000004611 spectroscopical analysis Methods 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 239000002966 varnish Substances 0.000 claims description 4
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 239000000984 vat dye Substances 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 244000198134 Agave sisalana Species 0.000 claims description 2
- ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 claims description 2
- 244000025254 Cannabis sativa Species 0.000 claims description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 240000000491 Corchorus aestuans Species 0.000 claims description 2
- 235000011777 Corchorus aestuans Nutrition 0.000 claims description 2
- 235000010862 Corchorus capsularis Nutrition 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 240000006240 Linum usitatissimum Species 0.000 claims description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 claims description 2
- 229920000877 Melamine resin Polymers 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 239000012491 analyte Substances 0.000 claims description 2
- 235000009120 camo Nutrition 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 235000005607 chanvre indien Nutrition 0.000 claims description 2
- 239000012084 conversion product Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 claims description 2
- 238000000407 epitaxy Methods 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 230000005284 excitation Effects 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 210000004209 hair Anatomy 0.000 claims description 2
- 239000011487 hemp Substances 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000012456 homogeneous solution Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- MELCHBVBYGSSOC-UHFFFAOYSA-N naphthalene-1-carboximidamide Chemical class C1=CC=C2C(C(=N)N)=CC=CC2=C1 MELCHBVBYGSSOC-UHFFFAOYSA-N 0.000 claims description 2
- 239000005445 natural material Substances 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920002480 polybenzimidazole Polymers 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
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- 229920000728 polyester Polymers 0.000 claims description 2
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- 229920001721 polyimide Polymers 0.000 claims description 2
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- 239000004926 polymethyl methacrylate Substances 0.000 claims description 2
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- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 84
- 238000005481 NMR spectroscopy Methods 0.000 description 60
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
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- 239000000203 mixture Substances 0.000 description 31
- 238000006862 quantum yield reaction Methods 0.000 description 30
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- 238000002844 melting Methods 0.000 description 15
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
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- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 2
- CXUGAWWYKSOLEL-UHFFFAOYSA-N 2h-cinnolin-3-one Chemical compound C1=CC=C2N=NC(O)=CC2=C1 CXUGAWWYKSOLEL-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
- PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 239000001055 blue pigment Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- SXMCIQXYGMZFMH-UHFFFAOYSA-N perylene-3,4-dicarboxylic anhydride Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 SXMCIQXYGMZFMH-UHFFFAOYSA-N 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- JEHCGAMWUNPVOI-UHFFFAOYSA-M st50974807 Chemical compound [K+].C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C(C([O-])=O)C2=C1C3=CC=C2C(=O)O JEHCGAMWUNPVOI-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- FXNJNGMYIZRQRG-UHFFFAOYSA-N tridecan-7-amine Chemical compound CCCCCCC(N)CCCCCC FXNJNGMYIZRQRG-UHFFFAOYSA-N 0.000 description 2
- ULAPHUAXIRVOTC-UHFFFAOYSA-N 1,2-di(heptan-4-yl)hydrazine Chemical compound CCCC(CCC)NNC(CCC)CCC ULAPHUAXIRVOTC-UHFFFAOYSA-N 0.000 description 1
- ATKSXVJFUPVUCV-UHFFFAOYSA-N 17-methyl-3,10,17-triazahexacyclo[13.6.2.02,10.04,9.012,22.019,23]tricosa-1(22),2,4,6,8,12,14,19(23),20-nonaene-11,16,18-trione Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C(=O)N(C)C(=O)C4=CC=C1C2=C43 ATKSXVJFUPVUCV-UHFFFAOYSA-N 0.000 description 1
- LSRYDXKYMCAGFS-UHFFFAOYSA-N 1h-naphthalene Chemical compound C1=CC=C2C=C[CH]CC2=C1 LSRYDXKYMCAGFS-UHFFFAOYSA-N 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- VHIDZOIKPWVLTP-UHFFFAOYSA-N C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)N(NCCCCCCC)C(=O)C4=CC=C3C1=C42 Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)N(NCCCCCCC)C(=O)C4=CC=C3C1=C42 VHIDZOIKPWVLTP-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004658 ketimines Chemical group 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GBEWPQKPCMZPBX-UHFFFAOYSA-N n-(1-hexylheptyl)perylene-3,4-dicarboximide Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)N(C(CCCCCC)CCCCCC)C(=O)C4=CC=C3C1=C42 GBEWPQKPCMZPBX-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- LBOJSACZVLWUHN-UHFFFAOYSA-N perylene-3,4-dicarboximide Chemical class C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 LBOJSACZVLWUHN-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- DDPWVABNMBRBFI-UHFFFAOYSA-N tert-butylhydrazine;hydron;chloride Chemical compound Cl.CC(C)(C)NN DDPWVABNMBRBFI-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/36—Benzo-cinnolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Paper (AREA)
- Paints Or Removers (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19900063A DE19900063A1 (de) | 1999-01-04 | 1999-01-04 | Naphthalin- und Perylenhydrazamimide - eine neue Klasse von Farbstoffen |
| US09/465,869 US6143890A (en) | 1999-01-04 | 1999-12-16 | Naphthalenehydrazamimides and perylenehydrazamimides |
| DE69902818T DE69902818T2 (de) | 1999-01-04 | 1999-12-24 | Naphthalenehydrazamimide und perylenhydrazamimide |
| JP2000592358A JP2002534552A (ja) | 1999-01-04 | 1999-12-24 | ナフタレンヒドラザムイミド類及びペリレンヒドラザムイミド類 |
| AT99965553T ATE223462T1 (de) | 1999-01-04 | 1999-12-24 | Naphthalenehydrazamimide und perylenhydrazamimide |
| PCT/EP1999/010367 WO2000040657A1 (en) | 1999-01-04 | 1999-12-24 | Naphthalenehydrazamimides and perylenehydrazamimides |
| AU21024/00A AU2102400A (en) | 1999-01-04 | 1999-12-24 | Naphthalenehydrazamimides and perylenehydrazamimides |
| EP99965553A EP1141140B1 (en) | 1999-01-04 | 1999-12-24 | Naphthalenehydrazamimides and perylenehydrazamimides |
| TW089100015A TW589350B (en) | 1999-01-04 | 2000-01-03 | Naphthalenehydrazamimides and perylenehydrazamimides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19900063A DE19900063A1 (de) | 1999-01-04 | 1999-01-04 | Naphthalin- und Perylenhydrazamimide - eine neue Klasse von Farbstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19900063A1 true DE19900063A1 (de) | 2000-07-27 |
Family
ID=7893563
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19900063A Withdrawn DE19900063A1 (de) | 1999-01-04 | 1999-01-04 | Naphthalin- und Perylenhydrazamimide - eine neue Klasse von Farbstoffen |
| DE69902818T Expired - Fee Related DE69902818T2 (de) | 1999-01-04 | 1999-12-24 | Naphthalenehydrazamimide und perylenhydrazamimide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69902818T Expired - Fee Related DE69902818T2 (de) | 1999-01-04 | 1999-12-24 | Naphthalenehydrazamimide und perylenhydrazamimide |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6143890A (https=) |
| EP (1) | EP1141140B1 (https=) |
| JP (1) | JP2002534552A (https=) |
| AT (1) | ATE223462T1 (https=) |
| AU (1) | AU2102400A (https=) |
| DE (2) | DE19900063A1 (https=) |
| TW (1) | TW589350B (https=) |
| WO (1) | WO2000040657A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2166040A1 (en) * | 2008-09-22 | 2010-03-24 | Radiant Color N.V. | Novel lipophilic fluorescent dyes and a process for their production |
| DE102004008480B4 (de) * | 2004-02-20 | 2011-06-22 | Theodor Heimeier Metallwerk GmbH, 59597 | Dichtigkeitsprüfung geschlossener Systeme mit Hilfe von Fluoreszenzfarbstoffen |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001245643A1 (en) * | 2000-03-14 | 2001-09-24 | Genigma Corporation | Biomarkers for the labeling, visual detection and quantification of biomolecules |
| US6391104B1 (en) | 2000-12-01 | 2002-05-21 | Bayer Corporation | Perylene pigment compositions |
| US6692562B2 (en) | 2002-03-08 | 2004-02-17 | Sun Chemical Corporation | Process for making perylene pigment compositions |
| DE102004006143A1 (de) | 2004-02-07 | 2005-08-25 | Wella Ag | Neue Naphthalinderivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern |
| DE102005053995A1 (de) * | 2005-11-10 | 2007-05-24 | Basf Ag | Verwendung von Rylenderivaten als Photosensibilisatoren in Solarzellen |
| JP5386884B2 (ja) | 2007-09-10 | 2014-01-15 | 株式会社リコー | ナフタレンテトラカルボン酸ジイミド誘導体、及び該ナフタレンテトラカルボン酸ジイミド誘導体を用いた電子写真感光体 |
| CN102841066A (zh) * | 2012-08-24 | 2012-12-26 | 深圳市谱尼测试科技有限公司 | 一种reach高度关注物质肼含量的测定方法 |
| US9812645B2 (en) | 2015-02-13 | 2017-11-07 | Flexterra, Inc. | Perylene-based semiconductors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2992220A (en) * | 1956-12-05 | 1961-07-11 | Ici Ltd | New anthra-1':9'(n):10'(n):5'-dipyridazones and anthra-1':9'(n):10'(n):4'-dipyridazones chemical compounds |
| DE4035009A1 (de) * | 1990-11-03 | 1992-05-07 | Hoechst Ag | Schwarze perylen-3,4,9,10-tetracarbonsaeurediimide, ihre herstellung und verwendung |
| DE59608872D1 (de) * | 1995-10-12 | 2002-04-18 | Ciba Sc Holding Ag | Naphthalinlactamimid-Fluoreszenzfarbstoffe |
| DE19701009A1 (de) * | 1997-01-14 | 1998-07-16 | Leonhard Feiler | Verfahren zur Herstellung von Perylen-3,4-dicarbonsäureanhydriden |
| DE59813430D1 (de) * | 1997-07-24 | 2006-05-04 | Ciba Sc Holding Ag | Perylenhydrazidimide als Carbonylderivatisierungsreagenzien |
-
1999
- 1999-01-04 DE DE19900063A patent/DE19900063A1/de not_active Withdrawn
- 1999-12-16 US US09/465,869 patent/US6143890A/en not_active Expired - Fee Related
- 1999-12-24 EP EP99965553A patent/EP1141140B1/en not_active Expired - Lifetime
- 1999-12-24 AU AU21024/00A patent/AU2102400A/en not_active Abandoned
- 1999-12-24 AT AT99965553T patent/ATE223462T1/de not_active IP Right Cessation
- 1999-12-24 JP JP2000592358A patent/JP2002534552A/ja active Pending
- 1999-12-24 DE DE69902818T patent/DE69902818T2/de not_active Expired - Fee Related
- 1999-12-24 WO PCT/EP1999/010367 patent/WO2000040657A1/en not_active Ceased
-
2000
- 2000-01-03 TW TW089100015A patent/TW589350B/zh not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004008480B4 (de) * | 2004-02-20 | 2011-06-22 | Theodor Heimeier Metallwerk GmbH, 59597 | Dichtigkeitsprüfung geschlossener Systeme mit Hilfe von Fluoreszenzfarbstoffen |
| EP2166040A1 (en) * | 2008-09-22 | 2010-03-24 | Radiant Color N.V. | Novel lipophilic fluorescent dyes and a process for their production |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000040657A1 (en) | 2000-07-13 |
| EP1141140B1 (en) | 2002-09-04 |
| AU2102400A (en) | 2000-07-24 |
| ATE223462T1 (de) | 2002-09-15 |
| US6143890A (en) | 2000-11-07 |
| DE69902818D1 (de) | 2002-10-10 |
| EP1141140A1 (en) | 2001-10-10 |
| TW589350B (en) | 2004-06-01 |
| DE69902818T2 (de) | 2003-07-31 |
| JP2002534552A (ja) | 2002-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |