US3856553A - Light-resistant-color developing sheet for pressure-sensitive copying paper - Google Patents

Light-resistant-color developing sheet for pressure-sensitive copying paper Download PDF

Info

Publication number
US3856553A
US3856553A US41057473A US3856553A US 3856553 A US3856553 A US 3856553A US 41057473 A US41057473 A US 41057473A US 3856553 A US3856553 A US 3856553A
Authority
US
United States
Prior art keywords
phenol
color developing
developing sheet
sheet according
clay
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
Application number
Other languages
English (en)
Inventor
T Hayashi
H Matsukawa
M Kiritani
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujifilm Holdings Corp
Original Assignee
Fuji Photo Film Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from JP45049339A external-priority patent/JPS4833210B1/ja
Priority to GB1949171A priority Critical patent/GB1309512A/en
Priority to DE2128518A priority patent/DE2128518B2/de
Priority to CA115,055A priority patent/CA944151A/en
Priority to FR7120804A priority patent/FR2096092A5/fr
Priority to BE768244A priority patent/BE768244A/xx
Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
Priority to US41057473 priority patent/US3856553A/en
Application granted granted Critical
Publication of US3856553A publication Critical patent/US3856553A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/10—Complex coacervation, i.e. interaction of oppositely charged particles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/0004—Preparation of sols
    • B01J13/0008—Sols of inorganic materials in water
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/025—Applications of microcapsules not provided for in other subclasses
    • 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
    • B41M5/155—Colour-developing components, e.g. acidic compounds; Additives or binders therefor; Layers containing such colour-developing components, additives or binders
    • 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
    • Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
    • Y10T428/258—Alkali metal or alkaline earth metal or compound thereof
    • 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]
    • Y10T428/31942—Of aldehyde or ketone condensation product
    • Y10T428/31949—Next to cellulosic
    • Y10T428/31964—Paper

Definitions

  • a color developing sheet comprising a support and a developer layer coated thereon, said developer layer containing an alkaline substance, such as, sodium hydroxide in addition to clay, such as, acid clay and a phenol compound, such as, p-phenyl phenol.
  • the alkaline substance increases the light resistance of a color image formed by pressure-contact of the developer sheet with a sheet which is coated with microcapsules containing a suitable mixture of couplers.
  • This invention relates to a color developing sheet for pressure-sensitive copying paper, and particularly to the improvement of a pressure-sensitive copying paper comprising a phenol compound as a color developer together.
  • the pressure-sensitive copying paper is produced by utilizing microcapsules containing a solution of a substantially colorless organic compound (hereinafter referred to as coupler) and an adsorbent material (hereinafter referred to as developer) which reacts with the coupler to form a distinctive color.
  • coupler substantially colorless organic compound
  • developer adsorbent material
  • Developers generally used include clays, such as, attapulgite, acid clay, active clay, zeolite or bentonite, an organic compound, such as succinic acid, tannic acid or gallic acid, and a phenol resin.
  • a phenol compound has been proposed in place of the developing agent (Japanese Patent Publication No. 9309/65).
  • a color image formed by reaction with a coupler such as, crystal violet lactone and benzoyl leuco methylene blue, has only insufficient weatherability. In other words, such color image has the defeet that it is easily discolored or faded by radiation of sunlight or on being left to stand indoors.
  • an object of this invention is to provide an improved pressure-sensitive copying paper.
  • Another object of the invention is to provide a method of improving the weatherability of a phenol compound used as a developer.
  • the phenol compounds used in the present invention are phenol compounds in which the hydrogen atom bonded to the aromatic ring is substituted with at least one hydroxyl group. Therefore, the phenol compounds used in the invention are monohydric or polyhydric phenols in the strict chemical sense.
  • phenols such as p-cresol, pnonylphenol, p-phenol phenol, p-(p-bromophenyl) phenol, biphenyl phenol, 2,4-xylenol, 2,4-diphenyl phenol, 2-chloro-4-phenyl phenol, 2,3,5- trimethylphenol, tetramethyl phenol, p-t-butyl phenol and p-t-amyl phenol.
  • phenols such as p-cresol, pnonylphenol, p-phenol phenol, p-(p-bromophenyl) phenol, biphenyl phenol, 2,4-xylenol, 2,4-diphenyl phenol, 2-chloro-4-phenyl phenol, 2,3,5- trimethylphenol, tetramethyl phenol, p-t-butyl phenol and p-t-amyl phenol.
  • polyhydric phenols in the strict chemical sense, .there may be mentioned 4-phenyl pyrocatechol, o,o'-biphenol, 4,4'-bi-ocresol, a, a'-diphenyl-4,4-bi-o-cresol, biphenyl tetrol, 2,4'-methylene diphenol, methylene diresorcinol, 2,2- methylene di-p-cresol, methylene bis-(benzylphenol), p-p'-isopropylidene diphenol, methylene bis-(phenyl phenol), methylene bis-(halophenol), and 4,4- thiodiphenol.
  • the alkaline substances used in this invention include hydroxides and carbonates of alkali metals or alkaline earth metals, such as, sodium, potassium, lithium, calcium, magnesium or barium.
  • Suitable amounts of the phenol compound are 1-10 parts by weight per parts by weight of clay, and those of the alkaline substance are 0.2-30 parts by weight on the same basis.
  • the method of adding these compounds is not particularly limited.
  • the alkaline substance may be added to a slurry of clay, and then the phenol compound may be added, or this order of addition may be reversed.
  • a mixture of the phenol compound and the alkaline substance may be added to a slurry of clay. It is possible to add organic acids, inorganic acids, or ion-exchange resins to a coating solution of the developer.
  • the alkaline substance When the'developer of the invention is used, its activity is enhanced by the alkaline substance, and there can be produced a pressure-sensitive copying paper which forms a color image of higher density. It must be emphasized, however, that the main purpose of using the alkaline substance is to increase the weatherability of a color image formed by adsorption to the phenol compound and clay upon reaction, and the increase in the activity of the conventional developers is of secondary significance.
  • a coating solution so obtained in accordance with the present invention is coated on a support such as paper either singly or in combination with microcapsules containing a coupler to be described.
  • the examples of the coupler are crystal violet lactone which is 3,3-bis-(pdimethylaminophenyl)-6- dimethylamino phthalide, benzoyl leuco methylene blue, malachite green lactone which is 3,3-bis-(pdimethylaminophenyl) phthalide, Rhodamine B lactam, 3-dialkylamino-7-dialkylamino fluoranes, and 3- methyl-2,2'-spirobi (benzo-[fl-chromene), which may be used either alone or in a mixture.
  • crystal violet lactone which is 3,3-bis-(pdimethylaminophenyl)-6- dimethylamino phthalide
  • benzoyl leuco methylene blue malachite green lactone which is 3,3-bis-(pdimethylaminophenyl) phthalide
  • Rhodamine B lactam which is 3,3-bis-(pdimethylaminophenyl) phthal
  • the color coupler of pressure-sensitive copying paper is used in the form of a mixture in order to render complete the instantaneous-coloring properties and light resistance of a colored image.
  • the most well known combination is one of crystal violet lactone, which is a primary coupler and colors instantaneously, and benzoyl leuco methylene blue which has good light resistance.
  • crystal violet lactone which is a primary coupler and colors instantaneously
  • benzoyl leuco methylene blue which has good light resistance.
  • v crystal violet lactone colors instantaneously, but it takes a long time before benzoyl leuco methylene blue forms a color.
  • a colored image of crystal violet lactone fades during this time interval.
  • Pressure sensitive copying paper which forms a black color usually contains a mixture of couplers which form various colors. According to the present invention, a complete black image can be obtained without assuming a red color in sunlight and the like.
  • Microcapsules containing a coupler are produced, for instance, in accordance with the method of U.S. Pat. No. 2,800,457.
  • One specific example is as follows: Ten parts of acid-treated pigskin gelatin and 10 parts of gum arabic are dissolved in 400 parts of water at 40C. With addition of 0.2 part of Turkey red oil as an emulsifier, 40 parts of a coupler oil is emulsified in the aqueous solution.
  • the coupler oil consists of 4 parts of chlorodiphenyl containing 2 percent of crystal violet lactone and 1.5 percent of benzoyl leuco methylene blue dissolved therein. The emulsification is stopped when the drop size of the oil is 5 microns on an average.
  • Water at 40C is added to the emulsion to adjust the total amount to 900 parts, and stirring is continued. At this time, care should be taken not to lower the temperature of the liquid below 40C. Thereafter, percent acetic acid is added to adjust the pH of the liquid to 4.0-4.2 to cause coacervation. Stirring is further continued, and after a lapse of 20 minutes, the mixture is cooled with ice water to gel coacervate film deposited around the oil droplets. When the temperature of the liquid reaches 20 C, 7 parts of 37 percent formaldehyde is added, and at 10 C, a percent aqueous solution of sodium hydroxide is added to adjust the pH to 9. The addition of the sodium hydroxide at this time should be performed with utmost care.
  • the mixture is heated for minutes to adjust the temperature of the liquid to 50C.
  • the microcapsules so obtained are cooled down to 30 C, and coated in an amount of 6 g/m as solids content on a base material having a unit weight of 40 g/m.
  • EXAMPLE 1 Eight parts of sodium hydroxide (20%) was added to 300 parts of dispersing water, and a solution of 4 parts of p-phenyl phenol in 40 parts of methanol was added (p-phenyl phenol being dissolved as dodecasodium salt). With stirring, 100 parts of acid clay was gradually added, and then 20parts (as solids content) of a styrene-butadiene latex was added to form a coating solution which had a pH of 9.5. The coating solution was applied to a base paper having a unit weight of 40 g/m in an amount of 10 g/m calculated as solids content using a coating rod.
  • Comparative Example 1 One hundred parts of acid clay was gradually added to 300 parts of dispersing water with stirring. A solution of 4 parts of p-phenyl phenol in 30 parts of methanol was added gradually with stirring, and 20 parts of a styrene-butadiene rubber latex (as solids content) was added gradually with stirring to form a coating solution. The coating solution was applied to a base paper having a unit weight of 40 g/m in an amount of 10 g/m as solids content using a coating rod, and then allowed to dry.
  • Comparative Test A Paper coated withmicrocapsules containing crystal violet lactone was superposed on each of the developer sheets obtained in Example 1 and Comparative Example 1, and a color was formed by applying a pressure of 600 Kg/cm After allowing it to stand for one hour in a dark place, the absorption spectrum curve at a wavelength in the range of 700 to 380p. was measured of each sheet. The absorption spectrum curve of the coupler after one-hour and three-hour irradiation of sunlight was also measured. The results obtained are shown in FIG. 1 attached in which [I] refers to the 'l)o11sil1y at absorption maximum after sunlight.
  • EXAMPLE 2 Ten parts of 20 percent potassium hydroxide was added to 300 parts of dispersing water, and a solution of4 parts ofp,p'-isopropylidene diphenol in 40 parts of methanol was added. With stirring, acid clay was gradually added, and then 20 parts (as solids content) of a styrene-butadiene rubber latex was added with slow stirring to form a coating solution which had a pH of 9.8. The coating solution was applied to base paper having a unit weight of 40 g/m as solids content.
  • Comparative Example 2 Acid clay was gradually added to 300 parts of dispersing water with stirring. With continued stirring, a solution of 4 parts of p,p-isopropylidene diphenol in methanol was added gradually. Subsequently, 20 parts, calculated as solids content, of a styrene-butadiene rubber latex was added with slow stirring to form a coating solution. The coating solution was applied to base paper having a unit weight of 40 g/m in an amount of g/m as solids content.
  • Comparative Test B Paper coated with microcapsules containing crystal violet lactone was superposed on each of the devel oper sheets obtained in Example 2 and Comparative Example 2, and a color was formed by applying a pres sure of 600 Kg/cm? After allowing it to stand for one hour in a dark place, the absorption spectrum curve at a wavelength in the range of 700 to 380p. was measured of each sheet. The absorption spectrum curve of the coupler after 1-hour and 3-hour irradiation of sunlight was also measured. The results are shown in FIG. 3, in which [1] refers to the sheet of Example 2, and [ll] refers to the sheet of Comparative Example 2, and the other symbols have the same significance as set forth in Comparative Test A, (1) above. The light resistance of crystal violet lactone at the absorption maximum is given in Table 4 below.
  • Example 2 A color was formed on each of the sheets obtained in Example 2 and Comparative Example 2 in the same manner as set forth in (l) above, using paper coated with microcapsules containing 3-dibenzylamino-7- diethylamino fluorane.
  • the absorption spectrum curve was measured, after allowing the sheet to stand for one hour in a dark place, and also after subjecting it to irradiation of sunlight for one hour and three hours respectively.
  • the results obtained are shown in FIG. 4 in which the symbols have the same significance as set 6 forth in (1) above.
  • the light resistance of the coupler at the absorption maximum lt is given in Table 5.
  • EXAMPLE 3 plied to a base paper having a unit weight of 40 g/m in an amount of 10 g/m as solids content.
  • Comparative Test C Paper coated with microcapsules containing crystal violet lactone was superposed on each of the developer sheets obtained in Example 3 and Comparative Example 1, and a color was formed by applying pressure of 600 Kg/cm The absorption spectrum curve of each sheet was measured, after allowing it to stand for one hour in a dark place, and this was designated as a fresh absorption spectrum curve. Thereafter, the absorption spectrum was also measured, after subjecting the sheet to sunlight irradiation for one hour and three hours respectively. The results obtained are shown in FIG. 5 in which [1] refers to the sheet obtained in Example 3, and [11] refers to the sheet of Comparative Example l, and the other symbols have the same significance as set forth in Comparative Test A, (l). The absorption spectrum curves of Comparative Example 1 were the same as those shown in FIG. 1. The light resistance of the coupler at the absorption maximum is given in Table 7.
  • a color developing sheet for pressure-sensitive copying paper comprising a support and a developer layer coated thereon, said developer layer comprising an alkaline substance selected from the group consist ing of an alkali metal hydroxide and an alkali metal carbonate, in addition to a clay and a phenol compound in which the hydrogen atom bonded to the aromatic ring is substituted with at least one hydroxyl group,
  • said alkaline substance being present in an amount of from 0.2 to 30 parts by weight per parts by weight of said clay and said phenol compound being present in an amount of from 1 to 10 parts by'weight per 100 parts by weight of clay.
  • a color developing sheet according to claim 1, wherein said phenol compound is a member selected from the group consisting of p-t-butyl phenol, p-t-amyl phenol, p-cresol, p-nonylphenol, p(p-bromophenyl) phenol, biphenyl phenol, 2,4-xylenol, 2,4-diphenyl phenol, 2-chloro-4-phenyl phenol, 2,3,5-trimethyl phenol, tetramethyl phenol, 4-phenyl pyrocatechol, 0,0- biphenol, 4,4'-bi-o-cresol, a, a-diphenyl-4,4'-bi-ocresol, biphenyl tetrol, 2,4-methylene diphenol, methylene diresorcinol, 2,2-methylene di-p-cresol, methylene bis-(benzylphenol), methylene bis-(phenyl phenol), methylene bis-(halo-phenol), and
  • a color developing sheet according to claim 1 wherein said alkaline substance is sodium hydroxide.
  • a color developing sheet according to claiml wherein said alkaline substance is potassium hydroxide.
  • a color developing sheet according to claim 1 wherein said phenol compound is p-phenyl phenol or p,p-isopropylidene diphenol.
  • a color developing sheet according to claim 1 wherein said phenol compound is p-phenyl phenol.
  • a color developing sheet according to claim 1 wherein said phenol compound is selected from the group consisting of p-t-butyl phenol, p-t-amyl phenol, p-cresol, p-nonylphenol, p(p-bromophenyl) phenol, biphenyl phenol, 2,4-xylenol, 2,4-diphenyl phenol, 2- chloro-4 phenyl phenol, 2,3,5-trimethyl phenol and

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Color Printing (AREA)
US41057473 1970-06-08 1973-10-29 Light-resistant-color developing sheet for pressure-sensitive copying paper Expired - Lifetime US3856553A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB1949171A GB1309512A (en) 1970-06-08 1971-06-08 Developer sheets for pressure-sensitive recording
DE2128518A DE2128518B2 (de) 1970-06-08 1971-06-08 Farbentwicklungsblatt fur druck empfindliche Kopierpapiere
CA115,055A CA944151A (en) 1970-06-08 1971-06-08 Light-resistant-color developing sheet for pressure-sensitive copying paper
FR7120804A FR2096092A5 (xx) 1970-06-08 1971-06-08
BE768244A BE768244A (fr) 1970-06-08 1971-06-08 Feuille revelant les couleurs, resistant a la lumiere, utilisable avec un papier a reproduire sensible a la pression
US41057473 US3856553A (en) 1970-06-08 1973-10-29 Light-resistant-color developing sheet for pressure-sensitive copying paper

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP45049339A JPS4833210B1 (xx) 1970-06-08 1970-06-08
US15104671A 1971-06-08 1971-06-08
US41057473 US3856553A (en) 1970-06-08 1973-10-29 Light-resistant-color developing sheet for pressure-sensitive copying paper

Publications (1)

Publication Number Publication Date
US3856553A true US3856553A (en) 1974-12-24

Family

ID=27293604

Family Applications (1)

Application Number Title Priority Date Filing Date
US41057473 Expired - Lifetime US3856553A (en) 1970-06-08 1973-10-29 Light-resistant-color developing sheet for pressure-sensitive copying paper

Country Status (6)

Country Link
US (1) US3856553A (xx)
BE (1) BE768244A (xx)
CA (1) CA944151A (xx)
DE (1) DE2128518B2 (xx)
FR (1) FR2096092A5 (xx)
GB (1) GB1309512A (xx)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3965282A (en) * 1973-09-14 1976-06-22 Agfa-Gevaert N.V. Thermographic recording material
US4022936A (en) * 1975-04-28 1977-05-10 Ncr Corporation Record material
US4076887A (en) * 1975-10-28 1978-02-28 Fuji Photo Film Co., Ltd. Recording sheets
US4148968A (en) * 1972-09-28 1979-04-10 Canon Kabushiki Kaisha Receiving sheet
US4172727A (en) * 1975-02-17 1979-10-30 Fuji Photo Film Co., Ltd. Desensitizer compositions
US4188456A (en) * 1977-12-23 1980-02-12 Ncr Corporation Pressure-sensitive recording sheet
US4342473A (en) * 1978-06-26 1982-08-03 Champion International Corporation Pressure-sensitive copy systems containing phenolic ester as color-stabilizers
US4379721A (en) * 1980-03-14 1983-04-12 Spezial-Papiermaschinenfabrik August Alfred Krupp Gmbh & Co. Pressure sensitive recording materials
US4409272A (en) * 1979-05-22 1983-10-11 The Wiggins Teape Group Limited Process for the manufacture of color developing material and product
EP0092091A3 (en) * 1982-04-15 1984-03-07 Allied Corporation Manufacture of powder cores for electromagnetic apparatus

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0162661A3 (en) * 1984-05-18 1987-01-14 Amoco Corporation Carbonless paper copying system

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2972547A (en) * 1957-08-05 1961-02-21 Antioch College Acyl hydrazine compositions and methods of producing color therewith
US3516845A (en) * 1967-01-24 1970-06-23 Ncr Co Record sheet sensitized with salt modified kaolin-phenolic material
US3540913A (en) * 1967-01-30 1970-11-17 Ncr Co Pressure sensitive recording sheet employing substituted indole phthalides
US3634121A (en) * 1969-03-17 1972-01-11 Ncr Co Acid-sensitized record sheet
US3641011A (en) * 1969-01-21 1972-02-08 Ncr Co 5- and 6-dialkylaminobenzylidene-aminofluorans

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2972547A (en) * 1957-08-05 1961-02-21 Antioch College Acyl hydrazine compositions and methods of producing color therewith
US3516845A (en) * 1967-01-24 1970-06-23 Ncr Co Record sheet sensitized with salt modified kaolin-phenolic material
US3540913A (en) * 1967-01-30 1970-11-17 Ncr Co Pressure sensitive recording sheet employing substituted indole phthalides
US3641011A (en) * 1969-01-21 1972-02-08 Ncr Co 5- and 6-dialkylaminobenzylidene-aminofluorans
US3634121A (en) * 1969-03-17 1972-01-11 Ncr Co Acid-sensitized record sheet

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4148968A (en) * 1972-09-28 1979-04-10 Canon Kabushiki Kaisha Receiving sheet
US3965282A (en) * 1973-09-14 1976-06-22 Agfa-Gevaert N.V. Thermographic recording material
US4172727A (en) * 1975-02-17 1979-10-30 Fuji Photo Film Co., Ltd. Desensitizer compositions
US4022936A (en) * 1975-04-28 1977-05-10 Ncr Corporation Record material
US4076887A (en) * 1975-10-28 1978-02-28 Fuji Photo Film Co., Ltd. Recording sheets
US4188456A (en) * 1977-12-23 1980-02-12 Ncr Corporation Pressure-sensitive recording sheet
US4342473A (en) * 1978-06-26 1982-08-03 Champion International Corporation Pressure-sensitive copy systems containing phenolic ester as color-stabilizers
US4409272A (en) * 1979-05-22 1983-10-11 The Wiggins Teape Group Limited Process for the manufacture of color developing material and product
US4379721A (en) * 1980-03-14 1983-04-12 Spezial-Papiermaschinenfabrik August Alfred Krupp Gmbh & Co. Pressure sensitive recording materials
EP0092091A3 (en) * 1982-04-15 1984-03-07 Allied Corporation Manufacture of powder cores for electromagnetic apparatus

Also Published As

Publication number Publication date
GB1309512A (en) 1973-03-14
DE2128518A1 (de) 1971-12-16
DE2128518B2 (de) 1973-09-13
FR2096092A5 (xx) 1972-02-11
BE768244A (fr) 1971-11-03
CA944151A (en) 1974-03-26

Similar Documents

Publication Publication Date Title
US3767449A (en) Recording sheet
US3856553A (en) Light-resistant-color developing sheet for pressure-sensitive copying paper
US3769062A (en) Pressure-sensitive recording paper
US4749680A (en) Color-developing agent for pressure-sensitive recording sheet and color-developing sheet therefor
US3955026A (en) Pressure-sensitive recording sheet
JPS6049118B2 (ja) 記録シ−トの製造方法
US4087284A (en) Color-developer coating for use in copy systems
US3843383A (en) Recording sheet employing an aromatic carboxylic acid
US3952117A (en) Method of desensitizing
US4147830A (en) Recording sheet
US3955025A (en) Pressure-sensitive copying sheet
US3833400A (en) Sheet with improved image durability
US4076887A (en) Recording sheets
US3834929A (en) Color developer sheet for pressure sensitive recording paper
CA1285765C (en) Color-developing sheet for pressure-sensitive recording sheet
JPS5819474B2 (ja) キロクシ−ト
US4473832A (en) Pressure-sensitive recording sheets
US3732141A (en) Pressure-sensitive record material
US3900217A (en) Pressure-sensitive copying paper
IE48723B1 (en) Pigment having a chromogenic material absorbed thereon and record receiving sheet having a coating thereof
US4159208A (en) Process for production of color developer
US3773542A (en) Sensitizing sheet for pressure- or heat-sensitive copying paper
EP0557649A1 (en) Coating compositions for pressure-sensitive record material
JPS6021875B2 (ja) 記録材料
US4835135A (en) Color-developing sheet for pressure-sensitive recording sheets