DE2049527A1 - Neue Fluoran Derivate und Verfahren zu deren Herstellung - Google Patents
Neue Fluoran Derivate und Verfahren zu deren HerstellungInfo
- Publication number
- DE2049527A1 DE2049527A1 DE19702049527 DE2049527A DE2049527A1 DE 2049527 A1 DE2049527 A1 DE 2049527A1 DE 19702049527 DE19702049527 DE 19702049527 DE 2049527 A DE2049527 A DE 2049527A DE 2049527 A1 DE2049527 A1 DE 2049527A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- aminophenol
- anhydride
- acid
- bis
- 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 19
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 26
- -1 alkyl radical Chemical class 0.000 claims description 19
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 16
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 14
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 12
- 229940018563 3-aminophenol Drugs 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000011592 zinc chloride Substances 0.000 claims description 7
- 235000005074 zinc chloride Nutrition 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 5
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 23
- 239000013078 crystal Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000370 acceptor Substances 0.000 description 6
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IZOHZBMGVGKMOO-UHFFFAOYSA-N 3-(n-methylanilino)phenol Chemical compound C=1C=CC(O)=CC=1N(C)C1=CC=CC=C1 IZOHZBMGVGKMOO-UHFFFAOYSA-N 0.000 description 4
- NDACNGSDAFKTGE-UHFFFAOYSA-N 3-hydroxydiphenylamine Chemical compound OC1=CC=CC(NC=2C=CC=CC=2)=C1 NDACNGSDAFKTGE-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- ZUMMIDKPYUJVIC-UHFFFAOYSA-N 3-(n-ethylanilino)phenol Chemical compound C=1C=CC(O)=CC=1N(CC)C1=CC=CC=C1 ZUMMIDKPYUJVIC-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- 238000007126 N-alkylation reaction Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KYGSADMIKAJPKC-UHFFFAOYSA-N 3-(4-chloro-N-methylanilino)phenol Chemical compound CN(C=1C=C(C=CC1)O)C1=CC=C(C=C1)Cl KYGSADMIKAJPKC-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- SUHWXARLXCIBFK-UHFFFAOYSA-N 3-(2-methylanilino)phenol Chemical compound CC1=CC=CC=C1NC1=CC=CC(O)=C1 SUHWXARLXCIBFK-UHFFFAOYSA-N 0.000 description 1
- GSHBBDLSLCDLCP-UHFFFAOYSA-N 3-(4-chloroanilino)phenol Chemical compound OC1=CC=CC(NC=2C=CC(Cl)=CC=2)=C1 GSHBBDLSLCDLCP-UHFFFAOYSA-N 0.000 description 1
- HGZJOFCYSPKYJM-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methylamino]phenol Chemical compound C1=CC(OC)=CC=C1CNC1=CC=CC(O)=C1 HGZJOFCYSPKYJM-UHFFFAOYSA-N 0.000 description 1
- LJKFBNRAMCUZMJ-UHFFFAOYSA-N 3-anilino-2-methylphenol Chemical compound CC1=C(O)C=CC=C1NC1=CC=CC=C1 LJKFBNRAMCUZMJ-UHFFFAOYSA-N 0.000 description 1
- UERPUZBSSSAZJE-UHFFFAOYSA-N 3-chlorophthalic anhydride Chemical compound ClC1=CC=CC2=C1C(=O)OC2=O UERPUZBSSSAZJE-UHFFFAOYSA-N 0.000 description 1
- LPUUYZVKCMCHLO-UHFFFAOYSA-N 4,5,6,7-tetrachloroisoindole-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)NC(=O)C2=C1Cl LPUUYZVKCMCHLO-UHFFFAOYSA-N 0.000 description 1
- PAODPKLYMCJZEG-UHFFFAOYSA-N 4,5,7-trichloro-2-benzofuran-1,3-dione Chemical compound ClC1=CC(Cl)=C(Cl)C2=C1C(=O)OC2=O PAODPKLYMCJZEG-UHFFFAOYSA-N 0.000 description 1
- HEGLMCPFDADCAQ-UHFFFAOYSA-N 4,7-dichloro-2-benzofuran-1,3-dione Chemical compound ClC1=CC=C(Cl)C2=C1C(=O)OC2=O HEGLMCPFDADCAQ-UHFFFAOYSA-N 0.000 description 1
- BTTRMCQEPDPCPA-UHFFFAOYSA-N 4-chlorophthalic anhydride Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1 BTTRMCQEPDPCPA-UHFFFAOYSA-N 0.000 description 1
- DVIKZIPMTWLDLT-UHFFFAOYSA-N 5,6-dibromo-2-benzofuran-1,3-dione Chemical compound C1=C(Br)C(Br)=CC2=C1C(=O)OC2=O DVIKZIPMTWLDLT-UHFFFAOYSA-N 0.000 description 1
- BCKVHOUUJMYIAN-UHFFFAOYSA-N 5-bromo-2-benzofuran-1,3-dione Chemical compound BrC1=CC=C2C(=O)OC(=O)C2=C1 BCKVHOUUJMYIAN-UHFFFAOYSA-N 0.000 description 1
- HAXOVWANMPEGGM-UHFFFAOYSA-N 5-iodo-2-benzofuran-1,3-dione Chemical compound IC1=CC=C2C(=O)OC(=O)C2=C1 HAXOVWANMPEGGM-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VKFKKXAGZIYIMO-UHFFFAOYSA-N ClC1=C2C(C(=O)NC2=O)=C(C(=C1Cl)Cl)Cl.[K] Chemical compound ClC1=C2C(C(=O)NC2=O)=C(C(=C1Cl)Cl)Cl.[K] VKFKKXAGZIYIMO-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229940070335 chlor-phen Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- CXWWOTMXNBKMBO-UHFFFAOYSA-N dimethyl 3,4,5,6-tetrachlorobenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)OC CXWWOTMXNBKMBO-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000010457 zeolite Substances 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/1455—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring characterised by fluoran compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/3275—Fluoran compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Color Printing (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8053969A JPS488725B1 (enExample) | 1969-10-08 | 1969-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2049527A1 true DE2049527A1 (de) | 1971-04-22 |
Family
ID=13721142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702049527 Pending DE2049527A1 (de) | 1969-10-08 | 1970-10-08 | Neue Fluoran Derivate und Verfahren zu deren Herstellung |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS488725B1 (enExample) |
| DE (1) | DE2049527A1 (enExample) |
| FR (1) | FR2064194B1 (enExample) |
| GB (1) | GB1273454A (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997049769A1 (en) * | 1996-06-27 | 1997-12-31 | The Perkin-Elmer Corporation | 4,7-dichlororhodamine dyes |
| US6017712A (en) * | 1996-06-27 | 2000-01-25 | Lee; Linda | 4,7-dichlororhodamine dyes |
| US6713622B1 (en) | 1996-06-27 | 2004-03-30 | Applera Corporation | 4,7-dichlororhodamine dye labeled polynucleotides |
| US7169939B2 (en) | 1996-05-03 | 2007-01-30 | Applera Corporation | Energy transfer dyes with enhanced fluorescence |
| US7388092B2 (en) | 1996-05-03 | 2008-06-17 | Applera Corporation | Oligonucleotides and analogs labeled with energy transfer dyes |
| US7550570B2 (en) | 2000-05-25 | 2009-06-23 | Applied Biosystems, Llc. | 4,7-dichlororhodamine dyes labeled polynucleotides |
| US7825237B2 (en) | 1996-05-03 | 2010-11-02 | Applied Biosystems, Llc | Oligonucleotides and analogs labeled with energy transfer dyes |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4826806A (en) * | 1986-07-31 | 1989-05-02 | Shin Nisso Kako Co., Ltd. | Fluoran compounds and color forming recording materials using same |
| JP5595449B2 (ja) | 2011-10-25 | 2014-09-24 | 三菱鉛筆株式会社 | 色素、それを用いたマイクロカプセル顔料及び筆記具用インク組成物 |
| GB201306667D0 (en) | 2013-04-12 | 2013-05-29 | Wellstream Int Ltd | A flexible pipe body and method of manufacture |
| EP3092184B1 (en) | 2014-01-07 | 2017-07-05 | Unilever Plc. | Aerosol venting method |
| WO2026140981A1 (ja) * | 2024-12-26 | 2026-07-02 | パイロットインキ株式会社 | 可逆熱変色性組成物およびそれを内包してなる可逆熱変色性マイクロカプセル顔料 |
-
1969
- 1969-10-08 JP JP8053969A patent/JPS488725B1/ja active Pending
-
1970
- 1970-10-05 FR FR7035857A patent/FR2064194B1/fr not_active Expired
- 1970-10-08 GB GB4792370A patent/GB1273454A/en not_active Expired
- 1970-10-08 DE DE19702049527 patent/DE2049527A1/de active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7449298B2 (en) | 1996-05-03 | 2008-11-11 | Applied Biosystems Inc. | Methods of analyzing polynucleotides employing energy transfer dyes |
| US7449149B2 (en) | 1996-05-03 | 2008-11-11 | Applied Biosystems Inc. | Kits useful for sequencing nucleic acids |
| US7825237B2 (en) | 1996-05-03 | 2010-11-02 | Applied Biosystems, Llc | Oligonucleotides and analogs labeled with energy transfer dyes |
| US7595162B2 (en) | 1996-05-03 | 2009-09-29 | Applied Biosystems, Llc | Methods of labeling polynucleotides with energy transfer dyes |
| US7169939B2 (en) | 1996-05-03 | 2007-01-30 | Applera Corporation | Energy transfer dyes with enhanced fluorescence |
| US7388092B2 (en) | 1996-05-03 | 2008-06-17 | Applera Corporation | Oligonucleotides and analogs labeled with energy transfer dyes |
| US7452672B2 (en) | 1996-05-03 | 2008-11-18 | Applied Biosystems Inc. | Methods of analyzing polynucleotides employing energy transfer dyes |
| US7432058B2 (en) | 1996-05-03 | 2008-10-07 | Applera Corporation | Methods of labeling nucleic acids with energy transfer dyes |
| US7399854B2 (en) | 1996-05-03 | 2008-07-15 | Applera Corporation | Regents labeled with energy transfer dyes |
| US7423140B2 (en) | 1996-05-03 | 2008-09-09 | Applied Biosystems Inc. | Oligonucleotides and analogs labeled with energy transfer dyes |
| WO1997049769A1 (en) * | 1996-06-27 | 1997-12-31 | The Perkin-Elmer Corporation | 4,7-dichlororhodamine dyes |
| US5847162A (en) * | 1996-06-27 | 1998-12-08 | The Perkin Elmer Corporation | 4, 7-Dichlororhodamine dyes |
| US6713622B1 (en) | 1996-06-27 | 2004-03-30 | Applera Corporation | 4,7-dichlororhodamine dye labeled polynucleotides |
| US6017712A (en) * | 1996-06-27 | 2000-01-25 | Lee; Linda | 4,7-dichlororhodamine dyes |
| US7550570B2 (en) | 2000-05-25 | 2009-06-23 | Applied Biosystems, Llc. | 4,7-dichlororhodamine dyes labeled polynucleotides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2064194B1 (enExample) | 1973-01-12 |
| JPS488725B1 (enExample) | 1973-03-17 |
| FR2064194A1 (enExample) | 1971-07-16 |
| GB1273454A (en) | 1972-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2747526C3 (de) | Druck- oder wärmeempfindliches Aufzeichnungsmaterial | |
| DE1795737C3 (de) | 3-(p-Aminophenyl)-3-(3-indolyl)phthalide und ihre Anwendung in druckempfindlichem Aufzeichnungsmaterial | |
| DE2166141C3 (de) | Indikatorfarbstoffe | |
| DE2265233A1 (de) | Neue farbstoffbildner und ihre verwendung | |
| DE2412640C3 (de) | Druckempfindliches Kopierpapier | |
| DE1671616B1 (de) | Druckempfindliches aufzeichnungsmaterial | |
| EP0014344B1 (de) | Cumarinverbindungen, Verfahren zu ihrer Herstellung und deren Verwendung als Weisstöner und Laserfarbstoffe | |
| DE2629937A1 (de) | Verfahren zur herstellung von triarylmethanderivaten | |
| DE1768862B2 (de) | Basisch substituierte fluorane, verfahren zu ihrer herstellung und deren verwendung als farbbildner fuer kopiermaterialien | |
| DE2505239A1 (de) | Verfahren zur herstellung tetracyclischer verbindungen | |
| DE2842263C2 (enExample) | ||
| DE2024859B2 (de) | Basisch substituierte Furanverbindungen und Verfahren zu deren Herstellung | |
| CH654839A5 (de) | Verfahren zur herstellung von basisch substituierten fluoranverbindungen. | |
| DE2530464C3 (de) | Druckempfindliches Kopiermaterial | |
| DE2242005A1 (de) | Verfahren zum herstellen von triphenylmethanderivaten | |
| DE2413986B2 (de) | Druckempfindliches Kopierpapier | |
| DE1561748A1 (de) | Druckempfindliches Kopierpapier | |
| DE2530463C3 (de) | Triphenylmethanverbindungen | |
| CH677232A5 (enExample) | ||
| DE1266425C2 (de) | Verfahren zur herstellung von anthrachinon-dispersionsfarbstoffen und deren verwendung | |
| DE2031490C3 (de) | Di-fluoranverbindungen | |
| DE3319978C2 (de) | Verfahren zur Herstellung von 4-Azaphthalidverbindungen | |
| DE2155986A1 (de) | Chromogene amino-substituierte Fluoran-Verbindungen | |
| DE1913120A1 (de) | Azacarbazolderivate und Verfahren zu ihrer Herstellung | |
| DE69204977T2 (de) | Mono(indolylethylenyl)phthalide. |