US3627581A - Pressure-sensitive record material - Google Patents
Pressure-sensitive record material Download PDFInfo
- Publication number
- US3627581A US3627581A US82198A US3627581DA US3627581A US 3627581 A US3627581 A US 3627581A US 82198 A US82198 A US 82198A US 3627581D A US3627581D A US 3627581DA US 3627581 A US3627581 A US 3627581A
- Authority
- US
- United States
- Prior art keywords
- sheet material
- isopropylbiphenyl
- record sheet
- percent
- liquid
- 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
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
- B41M5/165—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 characterised by the use of microcapsules; Special solvents for incorporating the ingredients
- B41M5/1655—Solvents
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
- Y10T428/2985—Solid-walled microcapsule from synthetic polymer
Definitions
- Roberts Dayton, Ohio ABSTRACT Record material comprising paper sheet materi- [54] PRESSURESENSITIVE RECORD MATERIAL a] coated with liquid-containing microcapsules wherein the 14 Claims No Drawings tquld contents comprise lsopr opylblphenyl and no halogenated hydrocarbon liquid. Said llqLlld IS associated on [52] U.S.C1 117/362, the record material with at least two color-producing reac- 1 17/156, 252/316, 106/137 tants, at least one of which is soluble in said liquid. The encap- [51] Int. Cl.
- B4lm 5/16 sulated liquid is associated with the reactants by either being [50] Field of Search 117/362, in close proximity to both reactants or by having one of the 36.8, 36.9 reactants dissolved therein and being in close proximity to the other.
- the color-producing reactants one is a chromogenic [56] Ree'ences cued dye-precursor and one is a coreactant material capable of UNITED STATES PATENTS developing the color of the chromogenic dye-precursor when 3,432,327 3/1969 Kan et a1 1 17/36.2 the feaciams are brought into reaction Contact by rupture of the capsule walls that contain said liquid.
- PRESSURE-SENSITIVE RECORD MATERIAL There is provided by this invention record material, comprising paper sheets coated with isolated liquid droplets, comprising isopropylbiphenyl and no halogenated hydrocarbon liquid. Said isolated liquid droplets are associated on the record material with at least two color-producing reactants, at least one of which is soluble in said liquid. The liquid is associated with the reactants by either being in close proximity to both reactants or by having one of the reactants dissolved therein and being in close proximity to the other.
- one is a chromogenic dye-precursor and one is a coreactant material capable of developing the color of the chromogenic dye-precursor when the two reactants are brought into reaction contact by rupture of the isolating medium.
- lsolation of the liquid droplets is preferably accomplished by encapsulation of the droplets with polymeric film material.
- CVL Crystal Violet Lactone
- an acidic coreactant material such as attapulgite clay or an oil-soluble, para-substitued-phenoLaldehyde novolak resin
- a liquid solvent that is at least in part a halogenated aromatic liquid, particularly mixtures of chlorinated biphenyls.
- Halogenated aromatic liquids have low vapor pressure and good solvent power and are readily retained by gelatin films (the most widely used capsular wall material). The halogenated aromatics have therefore served well as the solvent in pressure-sensitive record material systems of the type described.
- Amylbiphenyl as part of an encapsulated dye-precursor solvent system which does not also include halogenated aromatics has not, as far as is known, been taught in the art. However, amylbiphenyl was tested in the hope of its meeting the objects of this invention. Amylbiphenyl has not been found satisfactory in the record systems of this invention partly because of its low solubilizing power but mainly because of its perfonnance in use. Prints made on a standard commercial novolak-sensitized receiving sheet with a 2:1 amylbiphenyl-saturated hydrocarbon oil solution of CVL were much less intense than similarly made prints using a 2:1 chlorinated-biphenyl-saturated hydrocarbon oil solution of CVL.
- CVL-in-amylbiphenyl prints faded even more rapidly and completely than the known-art CVL- in-chlorinated-biphenyl prints.
- the failure of amylbiphenyl to meet the objects of this invention and improve on the chlorinated aromatic solvents of the known art made even more surprising the advantageous performance of isopropylbiphenyl, the use of which is set out herein.
- isoproplybiphenyl a compound or a mixture of compounds of the structure:
- the isopropyl group may be attached to the benzene ring at the ortho, meta or para positions.
- Synthetic methods commonly used produce a mixture of at least two of the three possible isopropylbiphenyls. Of particular use in this invention is the mixture wherein meta-isopropylbiphenyl and paraisopropylbiphenyl are the predominant isomers. These two isomers appear to perform in the record material systems of the invention equally well and whether alone or in combination to perform better than ortho-isopropylbiphenyl.
- lsopropylbiphenyl has been found to give better print intensities and better fade resistance than higher alkylated biphenyls such as butylbiphenyl, amylbiphenyl, hexylbiphenyl, decylbiphenyl, diisopropylbiphenyl and triisopropylbiphenyl.
- alkylated biphenyls such as butylbiphenyl, amylbiphenyl, hexylbiphenyl, decylbiphenyl, diisopropylbiphenyl and triisopropylbiphenyl.
- alkylated biphenyls such as butylbiphenyl, amylbiphenyl, hexylbiphenyl, decylbiphenyl, diisopropylbiphenyl and triisopropylbiphenyl.
- the impurities are polyisopropylbiphenyls, that is generally diisopropylbiphenyl with trace amounts of triisopropylbiphenyl
- no more than about 55 percent, by weight, of the total biaryl content should be such higher alkylated species.
- Preferably no more than about 25 to 30 percent of the total biaryl content is polysiopropylbiphenyl.
- Unalkylated biphenyl that is biphenyl itself, can also be tolerated as an impurity in the isopropylbiphenyl.
- Biphenyl as an impurity does not noticeably hurt the performance of isopropylbiphenyl in the record materials of this invention, but when biphenyl makes up more than about 10 percent of the total biaryl content the biphenyl odor generally makes such record materials commercially unacceptable.
- total biaryl content is meant the amount of isopropylbiphenyl present, together with its impurities,
- polyisopropylbiphenyl and biphenyl polyisopropylbiphenyl and biphenyl.
- polyisopropylbiphenyl is meant biphenyl having two or more isopropyl s i ssvb itqts ths q
- Nonhalogenated diluent oils may be added to the isopropylbiphenyl without adversely affecting the performance of the record systems made therewith.
- High-boiling aliphatic hydrocarbons and C, -C,,,-alkylbenzenes have been used successfully as isopropylbiphenyl diluents. Since these diluents are generally cheaper than isopropylbiphenyl, their use is in the interest of economy.
- Solubility of the chosen colorless, chromogenic dye-precursor material in the chosen diluent dictates the maximum amount of such diluent which can be used. If the isopropylbiphenyl is to be diluted with other oils, the diluted isopropylbiphenyl should be capable of dissolving at least one percent and preferably 1.5 percent or more of the chosen dye-precursor.
- the preferred diluents are saturated aliphatic hydrocarbon oils (with a distillation range in the range of 320 to 550 F.), which may be added to isopropylbiphenyl to make up about one-third of the total weight of the CVL solvent, and C,,C, -alkylbenzene which may be used to the extent of two-thirds of the total weight of said solvent.
- oils known to the art as useful internal phase solvents may be used as a diluent herein for the isopropylbiphenyl provided they are not halogenated, are at least partially miscible with isopropylbiphenyl so as to give a single phase in the proportions used, and are not chemically reactive with isopropylbiphenyl or the other components of the marking liquid.
- low molecular weight aromatic hydrocarbons such as xylene and toluene
- organic acid esters such as fatty acid esters and phthalic acid esters
- phosphate esters such as dibutylphosphate, dioctyl phosphate and dicresylphosphate
- ethers such as diphenyl oxide are alleligible foruse as diluent oils. 7 V
- An unexpected advantage of the record material of this invention is that color-production efficiency is also enhanced over the known-art systems which include chlorinated biphenyls. This allows the use of less marking liquid per unit area to produce the same amount of color.
- the color-production efficiency of record material coated with microcapsules having an internal phase consisting of 1.7 percent CVL dissolved in a 2:1 mixture of isopropylbiphenyl and saturated hydrocarbon oil is 16 percent greater than the colorproduction efficiency of record material coated with microcapsules having an internal phase consisting of 1.5 percent CVL dissolved in a 2:1 mixture of a chlorinated biphenyl (of 42 percent chlorine content) and saturated hydrocarbon oil. This increased efficiency reprewnts a saving in rawmaterial costs as well as reduced coating weights on the finished product.
- the preferred composition for use in this invention is approximately 50 percent meta-isopropylbiphenyl, 30 percent para-isopropylbiphenyl, 25 percent polyisopropylbiphenyl, 0.5 percent biphenyl. This preferred composition is best represented by Samples D" and N," above.
- Samples of isopropylbiphenyl having about 75 percent polyisopropylbiphenyl impurity associated with about 25 percent isopropylbiphenyl (a mixture of meta and para isomers) were found, when mixed 2:1 with a saturated hydrocarbon oil and used as the internal phase solvent for CVL, to give slightly less intense prints on phenolicresin sensitized paper than 2:1 chlorinated-biphenyksaturatcd hydrocarbon oil solutions of CVL did and to show no appreciable improvement in fade resistance.
- Satisfactory isopropylbiphenyl for use herein may be obtained commercially or may be synthesized by Friedel-Crafts alltylation of biphenyl, a study of which reaction is reported in industrial and Engineering Chemistry Product Research and Development, 8 239-241 (1969), by Duane B. Priddy.
- Dye-precursor materials in addition to CVL which may be dissolved in isopropylbiphenyl for encapsulation purposes include any colorless, chromogenic dye-precursor materials such as those disclosed in the U.S. application of Robert E. Miller and Paul S. Phillips, Jr., Ser. No. 44, 805, filed June 9, 1970.
- the same Miller-Phillips application also discloses those phenol-aldehyde resins eligible for use as coreactant materials to develop the color of the dye-precursor materials.
- the preferred resins are oil-soluble para-substitutedphenol-formaldehyde novolak resins.
- Capsule-wall materials and capsule manufacture are not critical to this invention. Suitable capsules may be made according to the procedures taught in U.S. Pat. Nos. 2,800,457 July 23, 1957), 2,800,458 (July 23, 1957) which became Re. 24,899 (Nov. 29, 1960) and 3,041,289 June 26, 1962). Other methods of isolating the marking droplets are also applicable here, such as entrapment of the droplets in a dried emulsion film.
- EXAMPLE 1 Encapsulation of CVL-isopropylbiphenyl Solution-A solution of CVL, 1.7 percent, in isopropylbiphenyl, Sample D"of Table l, was chosen for use as the internal phase of the capsules.
- the following formulation was emulsified in a Waring Blendor" at 55 C. to give internal phase droplets of 4 microns diameter:
- microcapsules After 4 hours of stirring, 12.0 milliliters of basic 5 percent PVM/MA (pH 9.0) is added, dropwise, to the mixture which is then stirred for an additional 2.5 hours while it gradually warms, up to about room temperature. The pH of the mixture, which is now a suspension of microcapsules, was finally adjusted to 9.5 with 20 percent sodium hydroxide.
- the microcapsulcs may be used as is, as an aqueous suspension or they may be isolated by filtration and airdried.
- EXAMPLE 2 Encapsulation of CVL-isopropylbiphenyl-hydrocarbon oil. According to the procedure of Example 1, microcapsules were made wherein a 2:1 mixture of isopropylbiphenyl and a saturated hydrocarbon oil (distillation range 370-500 F.) was substituted for the isopropylbiphenyl of that example.
- EXAMPLE 3 Encapsulation of CVL-isopropylbiphenyl-alkylbenzene.According to the procedure of example 1, microcapsules were made wherein a 1:2 mixture of isopropylbiphenyl and a mono-C to C -alkylbenzene was substituted for the isopropylbiphenyl of that example.
- EXAMPLE 4 Encapsulation of phenolic resin solution.-Gcnerally follow ing the method of example 1, a 10 percent solution of paraphenylphenolformaldchyde novolak resin in a 2:1 mixture of isopropylbiphenyl and xylene was encapsulated. The initial emulsion consisted of 180 grams of internal phase, 191 grams of 11 percent gelatin at pH 4.3 and 15.8 grams of deionized water. Coacervation was accomplished by the addition of 127 grams of 1 1 percent gum arabic solution, grams of 5 percent PVM/MA and 817 grams of deionized water.
- EXAMPLE 5 Capsule-Coated Record Material Sheets.--An aqueous coating slurry of the following composition was made up by stir- Water Paper sheets were coated with the above slurry with a No. Mayer rod to give a dried coating weight of about 3.5 pounds per ream (500 sheets, measuring 25x38 inches).
- Coatings made with the capsules of examples I, 2 or 3 gave record material sheets that yielded intense blue marks when marked on against acid-sensitized receiving sheets.
- the test receiving sheets were standard commercial receiving sheets sensitized according to the teaching of the previously cited Miller-Brockett application.
- the so-produced marks were more intense and more fade resistant (when exposed to light and air) than similar marks made with coated sheets having 2:1 chlorinated biphenyl-hydrocarbon oil as the capsular internal phase solvent for the CVL.
- Record sheet material comprising isolated droplets of an oil solution of a color-producing reactant material, selected from the group consisting of base-reacting colorless chromogenic dye-precursor materials and acid-reacting phenol-formaldehyde novolak resins capable of producing color in said dye-precursors when brought into reactive contact therewith, wherein said oil is a halogen-free oil comprising biaryl material selected from the group consisting of biphenyl.
- a color-producing reactant material selected from the group consisting of base-reacting colorless chromogenic dye-precursor materials and acid-reacting phenol-formaldehyde novolak resins capable of producing color in said dye-precursors when brought into reactive contact therewith, wherein said oil is a halogen-free oil comprising biaryl material selected from the group consisting of biphenyl.
- novolak resin is para-phenylphenol-formaldehyde resin.
- the record sheet material of claim 13 wherein the total biaryl content consists of about percent of a mixture metaisopropylbiphenyl and para-isopropylbiphenyl, about 20 percent of polyisopropylbiphenyl, and about l percent biphenyl.
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- Color Printing (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Measurement Of Unknown Time Intervals (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US8219870A | 1970-10-19 | 1970-10-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3627581A true US3627581A (en) | 1971-12-14 |
Family
ID=22169670
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US82198A Expired - Lifetime US3627581A (en) | 1970-10-19 | 1970-10-19 | Pressure-sensitive record material |
Country Status (17)
Country | Link |
---|---|
US (1) | US3627581A (nl) |
AT (1) | AT309474B (nl) |
AU (1) | AU449659B2 (nl) |
BE (1) | BE774127A (nl) |
BR (1) | BR7106910D0 (nl) |
CA (1) | CA965947A (nl) |
CH (1) | CH568857A5 (nl) |
DK (1) | DK129403B (nl) |
ES (1) | ES395698A1 (nl) |
FR (1) | FR2111473A5 (nl) |
GB (1) | GB1320273A (nl) |
IT (1) | IT938851B (nl) |
NL (1) | NL166222C (nl) |
NO (1) | NO133656C (nl) |
SE (1) | SE373071B (nl) |
SU (1) | SU504518A3 (nl) |
ZA (1) | ZA715910B (nl) |
Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3836383A (en) * | 1970-10-27 | 1974-09-17 | Fuji Photo Film Co Ltd | Pressure sensitive recording paper |
US3846331A (en) * | 1971-08-04 | 1974-11-05 | Kureha Chemical Ind Co Ltd | Solvent composition for dyes for use in pressure-sensitive copying paper |
US3865613A (en) * | 1971-09-23 | 1975-02-11 | Wiggins Teape Res Dev | Pressure-sensitive copying systems |
US3976427A (en) * | 1972-05-23 | 1976-08-24 | Sandoz Ltd. | Organic compounds |
JPS51127816A (en) * | 1975-04-28 | 1976-11-08 | Ncr Co | Materials of record sheets |
FR2309613A1 (fr) * | 1975-05-02 | 1976-11-26 | Kureha Chemical Ind Co Ltd | Perfectionnements aux solvants pour colorants utilisables dans des papiers copiants sensibles a la pression, et a de tels papiers copiants |
US3996405A (en) * | 1973-01-24 | 1976-12-07 | Ncr Corporation | Pressure-sensitive record material |
US4003589A (en) * | 1970-07-11 | 1977-01-18 | Kureha Kagaku Kogyo Kabushiki Kaisha | Carbonless copying paper |
US4012554A (en) * | 1972-12-15 | 1977-03-15 | Ncr Corporation | Single coating record system-solvent loss produces color |
US4039712A (en) * | 1971-03-02 | 1977-08-02 | Nippon Petrochemicals Company Ltd. | Process for producing a solvent for use in microcapsule for pressure-sensitive copying paper |
US4064068A (en) * | 1975-07-30 | 1977-12-20 | Sun Oil Company Of Pennsylvania | Preparation of isopropylnaphthalene mixture |
DE2823758A1 (de) * | 1977-06-24 | 1979-01-11 | Westinghouse Electric Corp | Mit meta-isopropylbiphenyl isoliertes elektrisches gehaeuse |
WO1985005327A1 (en) * | 1984-05-21 | 1985-12-05 | Ncr Corporation | Marking liquid composition |
USRE32162E (en) * | 1971-03-02 | 1986-05-27 | Nippon Petrochemicals Co., Ltd. | Pressure sensitive record material employing diaryl alkane solvents |
US4684574A (en) * | 1984-03-09 | 1987-08-04 | Papierfabrik August Koehler Ag | Process for encapsulating dissolved reactants of color reaction system and resulting capsules |
US4699658A (en) * | 1986-05-02 | 1987-10-13 | Kureha Kagaku Kogyo Kabushiki Kaisha | Solvent for chromogenic dye-precursor material for pressure-sensitive recording paper sheet and pressure-sensitive recording paper sheet prepared by using the solvent |
EP0243554A1 (en) * | 1986-05-02 | 1987-11-04 | Kureha Kagaku Kogyo Kabushiki Kaisha | Solvent for chromogenic dye-precursor material for pressure-sensitive recording paper |
FR2611211A1 (fr) * | 1987-02-19 | 1988-08-26 | Kureha Chemical Ind Co Ltd | Solvant pour precurseur de colorant chromogene pour feuille de papier autocopiant et feuille de papier autocopiant preparee a l'aide du solvant |
US4774136A (en) * | 1986-05-02 | 1988-09-27 | Kureha Kagaku Kogyo Kabushiki Kaisha | Solvent for the chromogenic dye-precursor material for a pressure-sensitive recording paper sheet and a pressure-sensitive recording paper sheet prepared by using the solvent |
US4795493A (en) * | 1986-01-07 | 1989-01-03 | Kureha Kagaku Kogyo Kabushiki Kaisha | Solvent for chromogenic dye-precursor material for pressure-sensitive recording paper sheet and pressure-sensitive recording paper sheet prepared by using the solvent |
US5318940A (en) * | 1992-12-02 | 1994-06-07 | Koch Industries, Inc. | Carbonless paper solvent comprising diisopropylbiphenyl and triisopropylbiphenyl and products utilizing same |
US5726456A (en) * | 1995-02-17 | 1998-03-10 | Gel Sciences, Inc. | Encapsulated materials |
US5849412A (en) * | 1995-02-17 | 1998-12-15 | Medlogic Global Corporation | Encapsulated materials |
WO2004000570A1 (en) | 2002-06-25 | 2003-12-31 | Appleton Papers Inc. | Product authentication |
US20040214134A1 (en) * | 2003-04-22 | 2004-10-28 | Appleton Papers Inc. | Dental articulation kit and method |
US20060063125A1 (en) * | 2003-04-22 | 2006-03-23 | Hamilton Timothy F | Method and device for enhanced dental articulation |
US20100099594A1 (en) * | 2008-10-17 | 2010-04-22 | Robert Stanley Bobnock | Fragrance-delivery composition comprising boron and persulfate ion-crosslinked polyvinyl alcohol microcapsules and method of use thereof |
US10092023B2 (en) * | 2012-05-24 | 2018-10-09 | Firmenich Sa | Hybrid coacervate capsules |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9221621D0 (en) * | 1992-10-15 | 1992-11-25 | Wiggins Teape Group Ltd | Solvents for use in pressure-sensitive record material |
CN101983267B (zh) * | 2008-03-31 | 2014-02-19 | 国际纸业公司 | 在低添加剂水平下具有改善的印刷质量的记录片材 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3432327A (en) * | 1964-03-13 | 1969-03-11 | Pilot Pen Co Ltd | Pressure sensitive copying sheet and the production thereof |
US3481759A (en) * | 1966-08-22 | 1969-12-02 | Minnesota Mining & Mfg | Impact marking carbonless paper |
US3488207A (en) * | 1965-10-22 | 1970-01-06 | Us Plywood Champ Papers Inc | Process of preparing a colored substance and transfer copy set |
US3540913A (en) * | 1967-01-30 | 1970-11-17 | Ncr Co | Pressure sensitive recording sheet employing substituted indole phthalides |
-
1970
- 1970-10-19 US US82198A patent/US3627581A/en not_active Expired - Lifetime
-
1971
- 1971-08-23 CA CA121,148A patent/CA965947A/en not_active Expired
- 1971-09-03 ZA ZA715910A patent/ZA715910B/xx unknown
- 1971-09-13 AU AU33374/71A patent/AU449659B2/en not_active Expired
- 1971-09-24 SU SU1700242A patent/SU504518A3/ru active
- 1971-09-28 IT IT29219/71A patent/IT938851B/it active
- 1971-10-04 ES ES395698A patent/ES395698A1/es not_active Expired
- 1971-10-05 NO NO3658/71A patent/NO133656C/no unknown
- 1971-10-05 GB GB4622271A patent/GB1320273A/en not_active Expired
- 1971-10-15 SE SE7113082A patent/SE373071B/xx unknown
- 1971-10-18 DK DK505671AA patent/DK129403B/da not_active IP Right Cessation
- 1971-10-18 BR BR6910/71A patent/BR7106910D0/pt unknown
- 1971-10-18 FR FR7137265A patent/FR2111473A5/fr not_active Expired
- 1971-10-19 BE BE774127A patent/BE774127A/xx not_active IP Right Cessation
- 1971-10-19 NL NL7114361.A patent/NL166222C/nl not_active IP Right Cessation
- 1971-10-19 AT AT901571A patent/AT309474B/de active
- 1971-10-19 CH CH1522371A patent/CH568857A5/xx not_active IP Right Cessation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3432327A (en) * | 1964-03-13 | 1969-03-11 | Pilot Pen Co Ltd | Pressure sensitive copying sheet and the production thereof |
US3488207A (en) * | 1965-10-22 | 1970-01-06 | Us Plywood Champ Papers Inc | Process of preparing a colored substance and transfer copy set |
US3481759A (en) * | 1966-08-22 | 1969-12-02 | Minnesota Mining & Mfg | Impact marking carbonless paper |
US3540913A (en) * | 1967-01-30 | 1970-11-17 | Ncr Co | Pressure sensitive recording sheet employing substituted indole phthalides |
Cited By (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4003589A (en) * | 1970-07-11 | 1977-01-18 | Kureha Kagaku Kogyo Kabushiki Kaisha | Carbonless copying paper |
US3836383A (en) * | 1970-10-27 | 1974-09-17 | Fuji Photo Film Co Ltd | Pressure sensitive recording paper |
USRE33113E (en) * | 1970-10-27 | 1989-11-14 | Fuji Photo Film Co., Ltd. | Pressure sensitive recording paper |
US4039712A (en) * | 1971-03-02 | 1977-08-02 | Nippon Petrochemicals Company Ltd. | Process for producing a solvent for use in microcapsule for pressure-sensitive copying paper |
USRE32162E (en) * | 1971-03-02 | 1986-05-27 | Nippon Petrochemicals Co., Ltd. | Pressure sensitive record material employing diaryl alkane solvents |
US3846331A (en) * | 1971-08-04 | 1974-11-05 | Kureha Chemical Ind Co Ltd | Solvent composition for dyes for use in pressure-sensitive copying paper |
US3865613A (en) * | 1971-09-23 | 1975-02-11 | Wiggins Teape Res Dev | Pressure-sensitive copying systems |
US3976427A (en) * | 1972-05-23 | 1976-08-24 | Sandoz Ltd. | Organic compounds |
US4012554A (en) * | 1972-12-15 | 1977-03-15 | Ncr Corporation | Single coating record system-solvent loss produces color |
US3996405A (en) * | 1973-01-24 | 1976-12-07 | Ncr Corporation | Pressure-sensitive record material |
US4027065A (en) * | 1975-04-28 | 1977-05-31 | Ncr Corporation | Pressure-sensitive record material |
JPS5648319B2 (nl) * | 1975-04-28 | 1981-11-14 | ||
JPS51127816A (en) * | 1975-04-28 | 1976-11-08 | Ncr Co | Materials of record sheets |
FR2309613A1 (fr) * | 1975-05-02 | 1976-11-26 | Kureha Chemical Ind Co Ltd | Perfectionnements aux solvants pour colorants utilisables dans des papiers copiants sensibles a la pression, et a de tels papiers copiants |
US4064068A (en) * | 1975-07-30 | 1977-12-20 | Sun Oil Company Of Pennsylvania | Preparation of isopropylnaphthalene mixture |
US4266264A (en) * | 1977-06-24 | 1981-05-05 | Westinghouse Electric Corp. | Meta isopropyl biphenyl insulated electrical apparatus |
DE2823758A1 (de) * | 1977-06-24 | 1979-01-11 | Westinghouse Electric Corp | Mit meta-isopropylbiphenyl isoliertes elektrisches gehaeuse |
US4684574A (en) * | 1984-03-09 | 1987-08-04 | Papierfabrik August Koehler Ag | Process for encapsulating dissolved reactants of color reaction system and resulting capsules |
US4748146A (en) * | 1984-03-09 | 1988-05-31 | Papierfabrik August Koehler Ag | Process for encapsulating dissolved reactants of color reaction systems, the capsules obtained as a result thereof and their use in non-carbon papers |
WO1985005327A1 (en) * | 1984-05-21 | 1985-12-05 | Ncr Corporation | Marking liquid composition |
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Also Published As
Publication number | Publication date |
---|---|
DK129403B (da) | 1974-10-07 |
IT938851B (it) | 1973-02-10 |
NO133656B (nl) | 1976-03-01 |
BR7106910D0 (pt) | 1973-04-26 |
ES395698A1 (es) | 1974-12-16 |
NO133656C (nl) | 1976-06-09 |
BE774127A (fr) | 1972-02-14 |
DE2151178B2 (de) | 1977-06-08 |
NL166222B (nl) | 1981-02-16 |
DK129403C (nl) | 1975-02-24 |
FR2111473A5 (nl) | 1972-06-02 |
GB1320273A (en) | 1973-06-13 |
AU3337471A (en) | 1973-03-22 |
AT309474B (de) | 1973-08-27 |
CH568857A5 (nl) | 1975-11-14 |
NL166222C (nl) | 1981-07-15 |
AU449659B2 (en) | 1974-06-20 |
SE373071B (nl) | 1975-01-27 |
DE2151178A1 (de) | 1973-01-25 |
SU504518A3 (ru) | 1976-02-25 |
CA965947A (en) | 1975-04-15 |
NL7114361A (nl) | 1972-04-21 |
ZA715910B (en) | 1972-05-31 |
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Legal Events
Date | Code | Title | Description |
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AS | Assignment |
Owner name: APPLETON PAPERS INC. Free format text: MERGER;ASSIGNORS:TUVACHE, INC.;GERMAINE MONTEIL COSMETIQUES CORPORATION (CHANGED TO APPLETON PAPERS);REEL/FRAME:004108/0262 Effective date: 19811215 |