DE2025171A1 - - Google Patents
Info
- Publication number
- DE2025171A1 DE2025171A1 DE19702025171 DE2025171A DE2025171A1 DE 2025171 A1 DE2025171 A1 DE 2025171A1 DE 19702025171 DE19702025171 DE 19702025171 DE 2025171 A DE2025171 A DE 2025171A DE 2025171 A1 DE2025171 A1 DE 2025171A1
- Authority
- DE
- Germany
- Prior art keywords
- diethylamino
- fluorane
- pressure
- carbon atoms
- fluoran
- 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.)
- Granted
Links
- 239000003094 microcapsule Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- -1 fluoran compound Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000004927 clay Substances 0.000 claims description 6
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 229960000892 attapulgite Drugs 0.000 claims description 3
- 229910052625 palygorskite Inorganic materials 0.000 claims description 3
- 239000005011 phenolic resin Substances 0.000 claims description 3
- 229920001568 phenolic resin Polymers 0.000 claims description 3
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- 229910052570 clay Inorganic materials 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
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 claims description 2
- 229940107698 malachite green Drugs 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims 2
- DODIDSXJZADHFA-UHFFFAOYSA-N n-fluoro-2-methylaniline Chemical compound CC1=CC=CC=C1NF DODIDSXJZADHFA-UHFFFAOYSA-N 0.000 claims 1
- 229940043267 rhodamine b Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 239000011973 solid acid Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005354 coacervation Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-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
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- FQNKTJPBXAZUGC-UHFFFAOYSA-N 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O FQNKTJPBXAZUGC-UHFFFAOYSA-N 0.000 description 1
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 1
- JTTMYKSFKOOQLP-UHFFFAOYSA-N 4-hydroxydiphenylamine Chemical compound C1=CC(O)=CC=C1NC1=CC=CC=C1 JTTMYKSFKOOQLP-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 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
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FHWHYVYOMJDEJB-UHFFFAOYSA-N n-benzyl-n-fluoroaniline Chemical compound C=1C=CC=CC=1N(F)CC1=CC=CC=C1 FHWHYVYOMJDEJB-UHFFFAOYSA-N 0.000 description 1
- JQERLSQMCRYVJH-UHFFFAOYSA-N n-fluoro-2-methoxyaniline Chemical compound COC1=CC=CC=C1NF JQERLSQMCRYVJH-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 101150101567 pat-2 gene Proteins 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000033458 reproduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/914—Transfer or decalcomania
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31844—Of natural gum, rosin, natural oil or lac
- Y10T428/31848—Next to cellulosic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Color Printing (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4005669 | 1969-05-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2025171A1 true DE2025171A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-17 |
| DE2025171B2 DE2025171B2 (de) | 1976-11-04 |
| DE2025171C3 DE2025171C3 (de) | 1980-07-10 |
Family
ID=12570247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2025171A Expired DE2025171C3 (de) | 1969-05-23 | 1970-05-23 | Druckempfindliches Kopierpapier |
Country Status (7)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2905825A1 (de) * | 1978-02-15 | 1979-08-16 | Kanzaki Paper Mfg Co Ltd | Waermeempfindliches aufzeichnungsmaterial |
| FR2456740A1 (fr) * | 1979-05-14 | 1980-12-12 | Sterling Drug Inc | Derives de fluorane, leurs intermediaires de synthese et leur utilisation comme precurseurs de couleurs |
| DE4010641A1 (de) * | 1990-04-03 | 1991-10-10 | Bayer Ag | Farbbildner-mischung fuer druck- und waermeempfindliche aufzeichnungssysteme |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4917490B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-07-23 | 1974-05-01 | ||
| JPS492127B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-11-13 | 1974-01-18 | ||
| GB1338179A (en) * | 1970-12-15 | 1973-11-21 | Yamamoto Kagaku Gosei Kk | Naphthal fluoran compounds and their use in pressure sensitive copying paper |
| US3947471A (en) * | 1970-12-26 | 1976-03-30 | Sumitomo Chemical Company, Ltd. | Benz (c) fluoran compounds and recording sheet containing them |
| GB1459417A (en) * | 1973-05-21 | 1976-12-22 | Ciba Geigy Ag | Diamino substituted fluoran compounds their manufacture and their use |
| US4187193A (en) * | 1974-09-24 | 1980-02-05 | Champion International Corporation | Micro-capsules containing ureido fluoran chromogenic compounds |
| US4104437A (en) * | 1974-09-24 | 1978-08-01 | Champion International Corporation | Pressure-sensitive copy system including ureido fluoran chromogenic compounds |
| US3929828A (en) * | 1974-11-21 | 1975-12-30 | Moore Business Forms Inc | 3{40 -Amino-6{40 {0 or 7{40 -(pyrazol-1-yl)fluoran compounds |
| GB1473434A (en) * | 1974-11-21 | 1977-05-11 | Moore Business Forms Inc | 2-phenyl-1,2,3-triazolofuran compounds |
| US4444591A (en) * | 1977-08-02 | 1984-04-24 | Yamada Chemical Co., Ltd. | Chromogenic compounds and the use thereof as color former in copying or recording materials |
| JPS5434909A (en) * | 1977-08-08 | 1979-03-14 | Yamada Chem Co | Colored recording material |
| US4274660A (en) * | 1979-05-14 | 1981-06-23 | Sterling Drug Inc. | Carbonless duplicating and marking systems |
| DE3044120A1 (de) * | 1980-11-24 | 1982-07-15 | Basf Ag, 6700 Ludwigshafen | Druck- und thermoempfindliches aufzeichnungsmaterial |
| CH654839A5 (de) * | 1983-09-26 | 1986-03-14 | Ciba Geigy Ag | Verfahren zur herstellung von basisch substituierten fluoranverbindungen. |
| US6689619B2 (en) | 2000-04-26 | 2004-02-10 | Battelle Memorial Institute | Solvent-activated color-forming compositions |
| US6680205B1 (en) | 2000-04-26 | 2004-01-20 | Battelle Memorial Instittue | Solvent-activated color forming compositions |
-
1970
- 1970-05-20 GB GB24508/70A patent/GB1277545A/en not_active Expired
- 1970-05-20 ES ES379854A patent/ES379854A1/es not_active Expired
- 1970-05-21 FR FR7018474A patent/FR2048614A5/fr not_active Expired
- 1970-05-21 IE IE666/70A patent/IE34604B1/xx unknown
- 1970-05-22 US US40481A patent/US3669711A/en not_active Expired - Lifetime
- 1970-05-22 BE BE750824D patent/BE750824A/xx not_active IP Right Cessation
- 1970-05-23 DE DE2025171A patent/DE2025171C3/de not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2905825A1 (de) * | 1978-02-15 | 1979-08-16 | Kanzaki Paper Mfg Co Ltd | Waermeempfindliches aufzeichnungsmaterial |
| FR2456740A1 (fr) * | 1979-05-14 | 1980-12-12 | Sterling Drug Inc | Derives de fluorane, leurs intermediaires de synthese et leur utilisation comme precurseurs de couleurs |
| DE4010641A1 (de) * | 1990-04-03 | 1991-10-10 | Bayer Ag | Farbbildner-mischung fuer druck- und waermeempfindliche aufzeichnungssysteme |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2048614A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-19 |
| GB1277545A (en) | 1972-06-14 |
| ES379854A1 (es) | 1972-09-01 |
| IE34604L (en) | 1970-11-23 |
| US3669711A (en) | 1972-06-13 |
| BE750824A (fr) | 1970-11-03 |
| DE2025171B2 (de) | 1976-11-04 |
| DE2025171C3 (de) | 1980-07-10 |
| IE34604B1 (en) | 1975-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1671545C2 (de) | Druckempfindliches Kopierpapier | |
| DE2025171A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2455908A1 (de) | Desensibilisierungsmittel und seine verwendung | |
| DE2150106A1 (de) | Farbbildende Massen | |
| DE2422899C3 (de) | Basisch-substituierte Furanverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbbildner für ein druck- oder wärmeempfindliches Aufzeichnungsmaterial | |
| DE1671616B1 (de) | Druckempfindliches aufzeichnungsmaterial | |
| DE2163658C3 (de) | 3-<2-Alkoxy-4-amino-phenyl)-3-(3-indolyl)-phthalide sowie druckempfindliche Kopierpapiere, die diese enthalten | |
| DE1768862B2 (de) | Basisch substituierte fluorane, verfahren zu ihrer herstellung und deren verwendung als farbbildner fuer kopiermaterialien | |
| DE3438083A1 (de) | Chromogene azaphthalidverbindung und sie enthaltende farbbildende aufzeichnungszusammensetzung | |
| DE2457897A1 (de) | Aufzeichnungsblatt | |
| DE2252901A1 (de) | Aufzeichnungsbogen | |
| DE2707784C3 (de) | Aminothiofluoranverbindungen und deren Verwendung in druck- oder wärmeempfindlichen Kopier- und Aufzeichungspapieren | |
| DE2156371A1 (de) | Farbbildnermasse für druckempfindliche Aufzeichnungen | |
| DE1561748C3 (de) | Aufzeichnungsmaterial | |
| DE1543803C3 (de) | Basisch substituierte Fluorane und Verfahren zu ihrer Herstellung sowie deren Verwendung als Farbbildner für druckempfindliche Vervielfältigungsmaterialien | |
| DE2413986B2 (de) | Druckempfindliches Kopierpapier | |
| DE1421393B2 (de) | Beschichtungsmasse für Aufzeichnungsoder Vervielfältigungsmaterial, farblose oder schwach gefärbte, zur Farbbildung bei Berührung mit geeigneten Substanzen führende Stoffe enthaltend, und damit hergestellter Kopiersatz | |
| DE2016371B2 (de) | 2,4 Disubstituierte 6 amino fluorane und ein Verfahren zu ihrer Herstellung sowie deren Verwendung als Farbbildner für druckempfindliche Kopierpapiere | |
| DE2129467B2 (de) | Druckempfindliches Kopierpapier | |
| DE2245504C2 (de) | Basisch substituierte Fluoranverbindungen und diese Verbindungen enthaltende druck- bzw. wärmeempfindliche Aufzeichnungsmaterialien | |
| DE2152765C3 (de) | Farbentwickler und diesen enthaltender Aufzeichnungsbogen | |
| DE2120920C3 (de) | Sensibilisierter Bogen für druckempfindliche Aufzeichnungsmaterialien | |
| DE2237833A1 (de) | Phenoxazinverbindungen und diese enthaltende druckempfindliche kopierpapiere | |
| DE2022339C3 (de) | Druckempfindliches Aufzeichnungsmaterial | |
| DE2263292C3 (de) | Fluoranverbindungen und druckempfindliches Kopierpapier |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: KOHLER, M., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: SOLF, A., DR.-ING., 8000 MUENCHEN ZAPF, C., DIPL.-ING., PAT.-ANW., 5600 WUPPERTAL |