US3839361A - Dibenzylamino fluoran compounds - Google Patents
Dibenzylamino fluoran compounds Download PDFInfo
- Publication number
- US3839361A US3839361A US00123069A US12306971A US3839361A US 3839361 A US3839361 A US 3839361A US 00123069 A US00123069 A US 00123069A US 12306971 A US12306971 A US 12306971A US 3839361 A US3839361 A US 3839361A
- Authority
- US
- United States
- Prior art keywords
- diethylamino
- methyl
- compound
- reaction
- group
- 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
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- ZBCKLHSPIVVGMC-UHFFFAOYSA-N n-benzyl-n-fluoro-1-phenylmethanamine Chemical class C=1C=CC=CC=1CN(F)CC1=CC=CC=C1 ZBCKLHSPIVVGMC-UHFFFAOYSA-N 0.000 title description 5
- 239000000460 chlorine Substances 0.000 claims abstract description 16
- -1 DIBENZYLAMINOFLUORAN COMPOUND Chemical class 0.000 claims abstract description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract 4
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 8
- 229940073608 benzyl chloride Drugs 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000011973 solid acid Substances 0.000 description 6
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- UMGLBLXWFVODRF-UHFFFAOYSA-N formaldehyde;4-phenylphenol Chemical compound O=C.C1=CC(O)=CC=C1C1=CC=CC=C1 UMGLBLXWFVODRF-UHFFFAOYSA-N 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- BETNPSBTDMBHCZ-UHFFFAOYSA-N 1-(chloromethyl)-2,4-dimethylbenzene Chemical compound CC1=CC=C(CCl)C(C)=C1 BETNPSBTDMBHCZ-UHFFFAOYSA-N 0.000 description 1
- LZBOHNCMCCSTJX-UHFFFAOYSA-N 1-(chloromethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CCl)=C1 LZBOHNCMCCSTJX-UHFFFAOYSA-N 0.000 description 1
- PECXPZGFZFGDRD-UHFFFAOYSA-N 2-(chloromethyl)-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(CCl)=C1 PECXPZGFZFGDRD-UHFFFAOYSA-N 0.000 description 1
- ACNUVXZPCIABEX-UHFFFAOYSA-N 3',6'-diaminospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(N)C=C1OC1=CC(N)=CC=C21 ACNUVXZPCIABEX-UHFFFAOYSA-N 0.000 description 1
- GRIKUIPJBHJPPN-UHFFFAOYSA-N 3',6'-dimethoxyspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(OC)C=C1OC1=CC(OC)=CC=C21 GRIKUIPJBHJPPN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- 239000000975 dye Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- UTVVREMVDJTZAC-UHFFFAOYSA-N furan-2-amine Chemical compound NC1=CC=CO1 UTVVREMVDJTZAC-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
-
- 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
Definitions
- New fluoran compounds containing a dibenzylamino group or a nuclear substituted derivative thereof are provided by a novel method involving the reaction of an aminofiuoran and a benzyl chloride in the presence of alkali in an inert non-polar organic solvent.
- the dibenzylamino fluorans are incorporated as a remarkably effective color former in pressure sensitive copying paper.
- pressure sensitive copying paper consists of two sheets of paper, the lower surface of the upper leaf having applied thereto minute capsules containing a color reactive achromatic substance (hereinafter called a color former) dissolved in a low volatile solvent and the upper surface of the lower leaf being coated with a solid acid, such as acid clay, phenolic compounds, etc.
- a color former a color reactive achromatic substance
- a solid acid such as acid clay, phenolic compounds, etc.
- the color former various kinds of chemical compounds have been used, and, among others, the fluoran compounds have recently been occupying an important position in the pressure sensitive copying paper industry because of the rich variety of colors that such compounds develop and the high color-developing speeds.
- R and R are individually hydrogen, or methyl; R is hydrogen, halogen or lower alkyl; R, and R are individually methyl or ethyl; and n is a integer from 1 to 5.
- R R R R and R can be concurrently in any combination. In the case where R R or R are halogen, chlorine and bromine are preferred.
- the new fluoran compounds are outstanding in the significant requirements of color developing speed, developed color density, light resistance after color development and solubility thereof.
- the novel pressure sensitive copying paper the compounds are dissolved in a low volatile solvent and packed in minute capsules which are used in conjunction with a solid acid.
- non-polar solvent aromatic solvents such as benzene, toluene and Xylene are desirable.
- highly polar solvents such as alcohols and phenols, will hinder the separation and purification of the reaction products.
- solvents having a very weak polarity such as o-xylene and o-dichlorobenzene, are regarded as belonging to the class of non-polar solvents useful in the present invention.
- reaction temperatures and pressures are not criti cal, a wide range of temperatures can be used, but the reaction is preferably conducted at the reflux temperature of the aromatic solvent.
- the reaction can be conducted at atmospheric pressure or at superatmospheric pressures. Reduced pressures could be used, but such pressures result in unnecessary loss of solvent.
- the alkali compound potassium carbonate, sodium carbonate, caustic potash and caustic soda give the most favorable results.
- the alkali compound is used at least in an amount corresponding to the stoichiometric amount of aminofiuoran compound or benzyl halide.
- the product is recovered from the reaction mixture by conventional means, for example by precipitation with a lower alcohol or by crystallization.
- the dispersion was cooled down to below 10 C. with iced water under stirring, and 10% caustic soda was added to adjust its pH to 9. It was then gradually brought back to room temperature. It was applied to the lower surface of the upper leaf and dried.
- EXAMPLE 12 A pressure sensitive copying paper which uses the color former obtained in Example 6 was prepared as follows:
- the solvent of low volatility is diphenyl chloride.
- the solvent of low volatility is a lower alkyl diphenyl such as methyl-, ethyl-, and propyl diphenyl or a higher alkyl benzene, such as dodecyldecyland octylbenzene, having a boiling point of above 15 C. If the boiling point of the solvent is at least 150 C. it has suflicient low volatility according to the invention.
- the solid acid functions as an electron acceptive absorbent.
- zeolite zeolite, bentonite, attapulgite and silton can be used with excellent results.
- R and R are individually members selected from the group consisting of hydrogen, chlorine, bromine and methyl;
- R is a member selected from the group consisting of hydrogen, chlorine, bromine, and C lower alkyl;
- R; and R are individually members selected from the group consisting of methyl and ethyl; and
- n is an integer of from 1 to 2.
- a compound of Claim 1 which is 3-diethylamino-7- di (p-chlorob enzyl aminofluoran. methyl-7-dibenzylaminofluoran.
- a compound of claim 1 which is 3-diethylamino-7- bis (2',4'-dimethylb enzyl) aminofluoran.
- a compound of claim 1 which is S-dimethylamino- 7-dibenzylaminofluoran.
- a compound of claim 1 which is 3-diethylamino-7- bis(dimethylbenzyl)aminofluoran.
- a compound of claim 1 which is 3-diethylamino-6 chloro-7-dibenzylaminofiuoran.
- R and R are individually members selected from the group consisting of hydrogen, chlorine, bromine, and methyl;
- R is a member selected from the group consisting of hydrogen, chlorine, bromine, and C lower alkyl;
- R; and R are individually members selected from the group consisting of methyl and ethyl; and
- n is an integer of from 1 to 2, further wherein at least one of R R and R is other than hydrogen.
- R is chlorine, bromine or C lower alkyl.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Color Printing (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7313464A SE394868B (sv) | 1970-07-08 | 1970-12-10 | Tryckkensligt kopiepapper, hos vilket som fergbildare anvendes ett bensylaminofluoranderivat |
| SE7016736A SE385010B (sv) | 1970-07-08 | 1970-12-10 | Dibensylaminofluoranforening till anvendning som fergbildare i tryckkensligt kopieringspapper samt sett att framstella foreningen ifraga |
| US00123069A US3839361A (en) | 1970-07-08 | 1971-03-10 | Dibenzylamino fluoran compounds |
| BE765179A BE765179A (fr) | 1970-07-08 | 1971-04-02 | Preparation d'un copulant chromogene et papier de copie sensible a la pression incorporant ce copulant chromogene |
| GB2623271*A GB1335762A (en) | 1970-07-08 | 1971-04-19 | Dibenzylamino-fluorans |
| CH682871A CH558351A (de) | 1970-07-08 | 1971-05-10 | Verfahren zur herstellung von dibenzylaminofluoran-verbindungen und verwendung derselben zur herstellung von farb-kopierpapieren. |
| AT06986/72A AT318660B (de) | 1970-07-08 | 1971-05-13 | Druckempfindliches kopierpapier |
| AT414671A AT308105B (de) | 1970-07-08 | 1971-05-13 | Verfahren zur Herstellung von Dibenzylaminofluoranverbindungen |
| DE2166374A DE2166374C2 (de) | 1970-07-08 | 1971-06-22 | Druckempfindliches Kopierpapier |
| DE2130845A DE2130845B2 (de) | 1970-07-08 | 1971-06-22 | Dibenzylaminofluorane, ihre Her stellung und Verwendung |
| CA117,043A CA992085A (en) | 1970-07-08 | 1971-06-29 | Process for the production of fluoran compounds containing dibenzylamino group or its nucleons substitution derivative group |
| FR7124972A FR2100398A5 (enrdf_load_stackoverflow) | 1970-07-08 | 1971-07-08 | |
| US00288993A US3824119A (en) | 1970-07-08 | 1972-09-14 | Pressure sensitive copy paper employing dibenzylamino fluoran compounds |
| US05/450,167 US3998846A (en) | 1970-07-08 | 1974-03-11 | Process for preparing dibenzylamino fluoran compounds |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5971170A JPS4939163B1 (enrdf_load_stackoverflow) | 1970-07-08 | 1970-07-08 | |
| US00123069A US3839361A (en) | 1970-07-08 | 1971-03-10 | Dibenzylamino fluoran compounds |
| US00288993A US3824119A (en) | 1970-07-08 | 1972-09-14 | Pressure sensitive copy paper employing dibenzylamino fluoran compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/450,167 Division US3998846A (en) | 1970-07-08 | 1974-03-11 | Process for preparing dibenzylamino fluoran compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3839361A true US3839361A (en) | 1974-10-01 |
Family
ID=27296979
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00123069A Expired - Lifetime US3839361A (en) | 1970-07-08 | 1971-03-10 | Dibenzylamino fluoran compounds |
| US00288993A Expired - Lifetime US3824119A (en) | 1970-07-08 | 1972-09-14 | Pressure sensitive copy paper employing dibenzylamino fluoran compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00288993A Expired - Lifetime US3824119A (en) | 1970-07-08 | 1972-09-14 | Pressure sensitive copy paper employing dibenzylamino fluoran compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US3839361A (enrdf_load_stackoverflow) |
| AT (2) | AT308105B (enrdf_load_stackoverflow) |
| BE (1) | BE765179A (enrdf_load_stackoverflow) |
| CA (1) | CA992085A (enrdf_load_stackoverflow) |
| CH (1) | CH558351A (enrdf_load_stackoverflow) |
| DE (2) | DE2130845B2 (enrdf_load_stackoverflow) |
| FR (1) | FR2100398A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1335762A (enrdf_load_stackoverflow) |
| SE (2) | SE385010B (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3959571A (en) * | 1973-05-22 | 1976-05-25 | Shin Nisso Kako Co., Ltd. | Chromogenic fluoran derivatives and the preparation and use thereof |
| US3970671A (en) * | 1971-08-21 | 1976-07-20 | Kanzaki Paper Manufacturing Co., Ltd. | Chromogenic compounds and method for preparation thereof |
| US4334406A (en) * | 1978-03-15 | 1982-06-15 | Dowty Fuel Systems Limited | Fuel supply system |
| US4515971A (en) * | 1980-03-31 | 1985-05-07 | Hilton-Davis Chemical Co. | 5'/6'-Carboxyfluorans and derivatives thereof |
| US5006563A (en) * | 1989-12-14 | 1991-04-09 | Hoechst-Roussel Pharmaceuticals Inc. | Alkylamino- and alkylamino alkyl diarylketones |
| US5071480A (en) * | 1986-10-31 | 1991-12-10 | Ciba-Geigy Corporation | Fluoran color former mixture and use thereof in recording materials |
| US5149689A (en) * | 1986-10-31 | 1992-09-22 | Ciba-Geigy Corporation | Fluoran color former mixture and use thereof in recording materials |
| US5177111A (en) * | 1989-12-14 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Inc. | Alkylamino- and alkylamino alkyl diarylketones and pharmaceutical compositions thereof |
| US20040043314A1 (en) * | 2002-08-30 | 2004-03-04 | Nusrallah Jubran | Organophotoreceptors with a fluoran-based compound |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE397360B (sv) * | 1970-10-13 | 1977-10-31 | Kanzaki Paper Mfg Co Ltd | Fluoranforeningar, speciellt bensfluoranforeningar, till anvendning som fergmaterial i registrerings- och kopieringssystem och sett att framstella dessa nya foreningar |
| JPS5033891B2 (enrdf_load_stackoverflow) * | 1971-10-29 | 1975-11-04 | ||
| US3929825A (en) * | 1974-04-18 | 1975-12-30 | Mead Corp | Pyrazoloxanthene compounds and process for producing same |
| US4020056A (en) * | 1975-04-10 | 1977-04-26 | Ncr Corporation | Di-vinyl phthalides color formers |
| GB9414637D0 (en) * | 1994-07-20 | 1994-09-07 | Wiggins Teape Group The Limite | Presure-sensitive copying material |
| CA2680371A1 (en) | 2007-03-15 | 2008-09-18 | Basf Se | Heat-sensitive coating compositions based on resorcinyl triazine derivatives |
| EP2167323B1 (en) | 2007-07-18 | 2018-04-04 | DataLase Ltd | Laser-sensitive coating formulation |
| ES2377852T3 (es) | 2007-08-22 | 2012-04-02 | Datalase Ltd | Composición de revestimiento sensible al láser |
| KR20100074334A (ko) | 2007-11-07 | 2010-07-01 | 바스프 에스이 | 신규한 섬유 생성물 |
| RU2011120235A (ru) | 2008-10-23 | 2012-11-27 | Дейталейз Лимитед | Теплопоглощающие добавки |
| WO2010049282A1 (en) | 2008-10-27 | 2010-05-06 | Basf Se | Coating composition for marking substrates |
| US20120045624A1 (en) | 2008-10-27 | 2012-02-23 | Basf Se | Aqueous laser-sensitive composition for marking substrates |
| EP2714413B1 (en) | 2011-05-25 | 2018-01-17 | Tetra Laval Holdings & Finance SA | Improved near infrared absorbers |
| WO2013098076A1 (en) | 2011-12-30 | 2013-07-04 | Tetra Laval Holdings & Finance S.A. | Laminated color forming composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1671545U (de) | 1952-03-15 | 1954-02-11 | Neue Argus Gmbh | Kugelabsperrhahn. |
| FR1553291A (enrdf_load_stackoverflow) * | 1967-01-27 | 1969-01-10 |
-
1970
- 1970-12-10 SE SE7016736A patent/SE385010B/xx unknown
- 1970-12-10 SE SE7313464A patent/SE394868B/xx unknown
-
1971
- 1971-03-10 US US00123069A patent/US3839361A/en not_active Expired - Lifetime
- 1971-04-02 BE BE765179A patent/BE765179A/xx not_active IP Right Cessation
- 1971-04-19 GB GB2623271*A patent/GB1335762A/en not_active Expired
- 1971-05-10 CH CH682871A patent/CH558351A/xx not_active IP Right Cessation
- 1971-05-13 AT AT414671A patent/AT308105B/de not_active IP Right Cessation
- 1971-05-13 AT AT06986/72A patent/AT318660B/de not_active IP Right Cessation
- 1971-06-22 DE DE2130845A patent/DE2130845B2/de not_active Withdrawn
- 1971-06-22 DE DE2166374A patent/DE2166374C2/de not_active Expired
- 1971-06-29 CA CA117,043A patent/CA992085A/en not_active Expired
- 1971-07-08 FR FR7124972A patent/FR2100398A5/fr not_active Expired
-
1972
- 1972-09-14 US US00288993A patent/US3824119A/en not_active Expired - Lifetime
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3970671A (en) * | 1971-08-21 | 1976-07-20 | Kanzaki Paper Manufacturing Co., Ltd. | Chromogenic compounds and method for preparation thereof |
| US3959571A (en) * | 1973-05-22 | 1976-05-25 | Shin Nisso Kako Co., Ltd. | Chromogenic fluoran derivatives and the preparation and use thereof |
| US4334406A (en) * | 1978-03-15 | 1982-06-15 | Dowty Fuel Systems Limited | Fuel supply system |
| US4515971A (en) * | 1980-03-31 | 1985-05-07 | Hilton-Davis Chemical Co. | 5'/6'-Carboxyfluorans and derivatives thereof |
| US5071480A (en) * | 1986-10-31 | 1991-12-10 | Ciba-Geigy Corporation | Fluoran color former mixture and use thereof in recording materials |
| US5149689A (en) * | 1986-10-31 | 1992-09-22 | Ciba-Geigy Corporation | Fluoran color former mixture and use thereof in recording materials |
| US5006563A (en) * | 1989-12-14 | 1991-04-09 | Hoechst-Roussel Pharmaceuticals Inc. | Alkylamino- and alkylamino alkyl diarylketones |
| US5177111A (en) * | 1989-12-14 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Inc. | Alkylamino- and alkylamino alkyl diarylketones and pharmaceutical compositions thereof |
| US5300527A (en) * | 1989-12-14 | 1994-04-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Alkylamino-and alkylamino alkyl diarylketones |
| US20040043314A1 (en) * | 2002-08-30 | 2004-03-04 | Nusrallah Jubran | Organophotoreceptors with a fluoran-based compound |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2130845B2 (de) | 1973-12-06 |
| SE385010B (sv) | 1976-05-31 |
| CH558351A (de) | 1975-01-31 |
| US3824119A (en) | 1974-07-16 |
| DE2166374A1 (de) | 1973-11-15 |
| FR2100398A5 (enrdf_load_stackoverflow) | 1972-03-17 |
| GB1335762A (en) | 1973-10-31 |
| BE765179A (fr) | 1971-08-30 |
| AT308105B (de) | 1973-06-25 |
| DE2166374C2 (de) | 1984-03-01 |
| SE394868B (sv) | 1977-07-18 |
| AT318660B (de) | 1974-11-11 |
| DE2130845A1 (de) | 1972-01-13 |
| CA992085A (en) | 1976-06-29 |
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