US3669712A - Pressure-sensitive copying papers - Google Patents
Pressure-sensitive copying papers Download PDFInfo
- Publication number
- US3669712A US3669712A US3669712DA US3669712A US 3669712 A US3669712 A US 3669712A US 3669712D A US3669712D A US 3669712DA US 3669712 A US3669712 A US 3669712A
- Authority
- US
- United States
- Prior art keywords
- pressure
- color
- paper
- sensitive copying
- color former
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000011973 solid acid Substances 0.000 description 12
- 239000003094 microcapsule Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- -1 phosphorus oxy- Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 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
- 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
- 241000978776 Senegalia senegal Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005354 coacervation Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000839 emulsion Substances 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
- 239000005457 ice water Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-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
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000007754 air knife coating Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group 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
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 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
- 239000002775 capsule Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 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
- 230000002950 deficient Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 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
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
Definitions
- This invention relates to a pressure-sensitive copying paper. More particularly, this invention relates to a pressure-sensitive copying paper using a novel color former.
- a pressure-sensitive copying paper consists of a combination of an upper sheet prepared by dissolving an electron acceptive, color forming and almost colorless organic compound (hereinafter, such organic compounds are described as color former) in an organic solvent, encapsulating the solution as microcapsules, and applying the microcapsules to a support and a lower sheet prepared by applying an electron donating solid acid to another support.
- the pressure-sensitive paper is composed of a combination of the upper sheet, the lower sheet, and an intermediate sheet prepared by applying microcapsules containing an organic solvent solution of the color former to one surface of a support and applying the solid acid to the other surface of the same support.
- a pressure-sensitive paper of a type in which the microcapsules as described above and the solid acid are applied to one side of a support as a mixture thereof or as two layers is known.
- the sheets are piled so that the microcapsule layer is contacted with the layer of the solid acid and they are pressed locally.
- the coated layer is locally pressurized, whereby the microcapsules are ruptured and the dye solution in the microcapsules is contacted with the layer of the solid acid to form a color at the locally pressurized portions.
- solid acid such inorganic acid materials as bentonite, zeolite, acid clay, active clay, magnesium trisilicate, and the like, and organic acid materials such as benzoic acid, benzene-sulfonic acid, naphthol, and the like, are used.
- the known color formers with a red forming property have the following disadvantages. That is to say, since Rhodamine Lactone itself is unstable, when it is in a natural atmosphere, it is colored in a short period of time, i.e., it is spontaneously colored before it is contacted with the solid acid (hereinafter, the phenomenon is designated as color forming fog). On the other hand, with Rhodamine Anilinolactam, it takes a considerable amount of time before it is completely colored when the. color former is contacted with the solid acid.
- the color former used for pressure-sensitive copying papers is required to have properties such that the color former is colorless before it reacts with the solid acid on contact therewith and is stable in the atmosphere without forming a fog, and the color former is colored instantly when it is contacted with the solid acid.
- the colored image obtained has a high color density and also excellent light fastness and water resistance.
- the abovedescribed conventional color formers are deficient in these respects.
- an object of this invention is to provide a pressure-sensitive copying paper in which a compound having excellent properties is used.
- the color former used in this invention has the following general formula wherein R and R each is an alkyl group having from 1 to 5 carbon atoms, wherein R is an acyl group, and wherein R is an aryl group. 1
- R R R and R are as above described. That is to say, 1 mol of Intermediate A, an o (4-dialkylamino- Z-hydroxybenzoyDbenzoic acid and 1 mol of Intermedi ate B, a p-(N-acyl-N-arylamino)phenol are subjected to a condensation reaction for from 3 to 50 hours at from 20 to 90 C. in the presence of 'a dehydrating agent, such as sulfuric acid, fuming sulfuric acid, phosphoric anhydride, anhydrous zinc chloride, and phosphorus oxy-' chloride.
- 'a dehydrating agent such as sulfuric acid, fuming sulfuric acid, phosphoric anhydride, anhydrous zinc chloride, and phosphorus oxy-' chloride.
- reaction liquid is poured into a large amount of ice water, and then an aqueous alkaline solution such as an aqueous sodium hydroxide solution is added to the mixture to make the resultant mixture Weakly alkaline.
- aqueous alkaline solution such as an aqueous sodium hydroxide solution
- Intermediate A can be prepared by a known manner, for example, by refluxing under heating 1 mol of metadialkylamino-phenol and 1 mol of phthalic anhydride in toluene for a few hours as described in Friedlander, vol. 4, page 260.
- Intermediate B can be prepared by a known method, for example, by subjecting an aniline and hydroquinone to a dehydration condensation to give a p- (N-arylamino) phenol according to the following reaction formula,
- R is an aryl group, and by acyl ating the above product in a conventional manner as shown in Chemical Abstracts, 52, 7184.
- SYNTHESIS 1 (COLOR FORMER 1) 1 mol of o-(4-diethylamino-Z-hydroxybenzoyl)benzoic acid having the structure of Intermediate A, in which R is C H and R is C H and 1 mol of p-(N-acetoanilino)- phenol having the structure of Intermediate B, in which R3 is were condensed for 24 hours at about 50 C. in 10 mols of concentrated sulfuric acid.
- the pressure-sensitive paper of this invention is colorless before color forming reaction and is stable under atmospheric conditions unaccompanied by the formation of spontaneous color fog.
- the pressure-sensitive paper is colored on pressing, the color image is formed instantaneously or the color forming speed is extremely high.
- the color density of the copied image is high and the image has excellent light fastness and water resistance.
- the color thus formed has an absorption in the spectral region of from about 350 to 420 III 1., which corresponds to the light-sensitive region of a diazo light-sensitive paper, the copied image can be copied on a diazo light-sensitive paper.
- the color former corresponding to the above-described general formula is a red-forming dye but by mixing the color former with other known yellow-, purple-, blue-, or green-forming color formers, a pressure sensitive copying paper giving rise to various colors can be prepared.
- Example 1 3 g. of the color former 1 was dissolved in 100 g. of diphenyl trichloride and the solution was emulsified by adding thereto an aqueous solution of 20 g. of gum arabic in 160 g. of water. Then, an aqueous solution of 20 g. of acid-treated gelatin in 160 g. of Water was added to the emulsion. After reducing the pH of the emulsion to 5, 500 g. of water was added thereto to cause coacervation, whereby dense liquid films of gelatin and gum arabic were formed around the oil drops in which the color former had been dissolved. Subsequently, the pH was reduced to 4 and then 4 g. of 37% Formalin was added for hardening. During the above procedures, the temperature of the system was kept at 50 C. but then the system was cooled to C. for gelling the dense liquid films. The pH was increased to 9 for increasing the hardening effect,
- the capsule-containing liquid thus obtained was applied to a paper by a coating manner, such as roll coating or air knife coating, and dried.
- the upper paper produced was placed on a clay paper (a lower paper prepared by applying a clay material to a paper) and they were pressed locally by writing, whereby a red record is instantaneously obtained on the clay paper.
- the pressure sensitive paper of this invention showed sufficient light fastness and water resistance before and after color forming for practical use.
- Example 2 The same procedure as used in Example 1 was followed using each of the color formers 2-10 instead of the color former 1. The results showed that in each case of using the color former, a red record was instantaneously formed on a clay paper. Also, the properties of the pressure sensitive paper before and after color forming were excellent as in Example 1.
- a pressure-sensitive copying paper comprising a support having coated thereon a layer of microcapsules containing a fluoran compound having the following general formula wherein R and R each is an alkyl group having from 1 to 5 carbon atoms, wherein R is an acyl group, and wherein R is an aryl group, a second support having coated thereon a layer of an electron donating solid acid, whereby a distinct color is produced on contact of said fluoran compound with said acid.
- fluoran derivative is a member selected from the group consisting of 3-diethylamino-7- N-acetoanilino) -fluoran, 3-dimethylamino-7- (N-aceto-p-toluidino -fiuoran,
- a pressure-sensitive copying paper comprising a sup: port having coated thereon a layer of microcapsules containing a fluoran compound having .the following general formula, v 7
- R is an acyl group
- R and R each is an alkyl group having from 1 15 wherein R4 is an aryl group, and a layer of electron donating solid acid coated 'on said support whereby a distinctcolor is produced on contact of said fluoran compound With said acid.
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5081969 | 1969-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3669712A true US3669712A (en) | 1972-06-13 |
Family
ID=12869356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US3669712D Expired - Lifetime US3669712A (en) | 1969-06-27 | 1970-06-26 | Pressure-sensitive copying papers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3669712A (enrdf_load_stackoverflow) |
| BE (1) | BE752388A (enrdf_load_stackoverflow) |
| CA (1) | CA918918A (enrdf_load_stackoverflow) |
| ES (1) | ES381083A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2052855A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1264936A (enrdf_load_stackoverflow) |
| IE (1) | IE34334B1 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3920510A (en) * | 1972-08-01 | 1975-11-18 | Yamamoto Kagaku Gosei Kk | Pressure-and-heat-sensitive copying paper |
| US3959571A (en) * | 1973-05-22 | 1976-05-25 | Shin Nisso Kako Co., Ltd. | Chromogenic fluoran derivatives and the preparation and use thereof |
| US3979141A (en) * | 1974-11-21 | 1976-09-07 | Moore Business Forms, Inc. | Pressure-sensitive recording system comprising 3'-amino-6' or 7'-(pyrazol-1-yl)fluoran compounds as color precursors |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5033891B2 (enrdf_load_stackoverflow) * | 1971-10-29 | 1975-11-04 |
-
1970
- 1970-06-22 FR FR7022898A patent/FR2052855A5/fr not_active Expired
- 1970-06-22 GB GB1264936D patent/GB1264936A/en not_active Expired
- 1970-06-23 IE IE809/70A patent/IE34334B1/xx unknown
- 1970-06-23 CA CA086230A patent/CA918918A/en not_active Expired
- 1970-06-23 ES ES381083A patent/ES381083A1/es not_active Expired
- 1970-06-23 BE BE752388D patent/BE752388A/xx not_active IP Right Cessation
- 1970-06-26 US US3669712D patent/US3669712A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3920510A (en) * | 1972-08-01 | 1975-11-18 | Yamamoto Kagaku Gosei Kk | Pressure-and-heat-sensitive copying paper |
| USRE31412E (en) * | 1972-08-01 | 1983-10-11 | Yamamoto Kagaku Gosei Kabushiki Kaisha | Pressure-and-heat-sensitive copying paper |
| US3959571A (en) * | 1973-05-22 | 1976-05-25 | Shin Nisso Kako Co., Ltd. | Chromogenic fluoran derivatives and the preparation and use thereof |
| US3979141A (en) * | 1974-11-21 | 1976-09-07 | Moore Business Forms, Inc. | Pressure-sensitive recording system comprising 3'-amino-6' or 7'-(pyrazol-1-yl)fluoran compounds as color precursors |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2031488B2 (de) | 1976-04-29 |
| DE2031488A1 (de) | 1971-01-28 |
| FR2052855A5 (enrdf_load_stackoverflow) | 1971-04-09 |
| CA918918A (en) | 1973-01-16 |
| BE752388A (fr) | 1970-12-01 |
| IE34334B1 (en) | 1975-04-16 |
| ES381083A1 (es) | 1972-11-01 |
| GB1264936A (enrdf_load_stackoverflow) | 1972-02-23 |
| IE34334L (en) | 1970-12-27 |
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