US3900669A - Pressure-sensitive recording sheet with microcapsules having polyurea walls - Google Patents

Pressure-sensitive recording sheet with microcapsules having polyurea walls Download PDF

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Publication number
US3900669A
US3900669A US298888A US29888872A US3900669A US 3900669 A US3900669 A US 3900669A US 298888 A US298888 A US 298888A US 29888872 A US29888872 A US 29888872A US 3900669 A US3900669 A US 3900669A
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US
United States
Prior art keywords
pressure
recording sheet
polyamine
sensitive recording
adduct
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
US298888A
Inventor
Masataka Kiritani
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Fujifilm Holdings Corp
Original Assignee
Fuji Photo Film Co Ltd
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Publication date
Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
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Publication of US3900669A publication Critical patent/US3900669A/en
Publication of US3900669B1 publication Critical patent/US3900669B1/en
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Expired - Lifetime legal-status Critical Current

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    • 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
    • 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
    • B01J13/14—Polymerisation; cross-linking
    • B01J13/16—Interfacial polymerisation
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Color Printing (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Focusing (AREA)
  • Camera Bodies And Camera Details Or Accessories (AREA)

Abstract

A pressure-sensitive recording sheet having reduced color fog which comprises a base sheet and (1) a layer of microcapsules containing a color former in oil droplets surrounded by the wall of a polyurea obtained by the reaction of a polyisocyanate or isocyanate-containing polyisocyanate adduct with a polyamine or polyamine adduct, and (2) a layer of an adsorbent or color reactive substance capable of producing a distinct color upon contact with the color former. Layers (1) and (2) are applied to the same surface of the base material.

Claims (23)

1. A PRESSURE-SENSITIVE RECORDING SHEET WHICH COMPRISES A BASE MATERIAL AND (1) A LAYER OF A COLORLESS OR SUBSTANTIALLY COLORLESS COLOR-FORMING SUBSTANCE RENDERED COLORED UPON REACTION WITH A DEVELOPER, ENCAPSULATED IN WALLS OF A POLYUREA OBTAINED BY THE REACTION OF A POLYISOCYANATE OR ISOCYANATECONTAINING POLYISOCYANATE ADDUCT WITH A POLYAMINE OR POLYAMINE ADUCT, AND (2) A LAYER OF DEVELOPER CAPABLE OF GIVING A COLORED SUBSTANCE BY REACTION WITH SAID COLOR-FORMING SUBSTANCE, LAYERS (1) AND (2) BEING ON THE SAME SURFACE OF SAID BASE MATERIAL.
2. The pressure-sensitive recording sheet of claim 1, wherein said isocyanate-containing polyisocyanate adduct is an adduct formed between a polyisocyanate and a compound containing a hydrophilic group.
3. The pressure-sensitive recording sheet of claim 2, wherein said compound containing a hydrophilic group is selected from the group consisting of polyamines, polycarboxylic acids, polyols, polythiols, polyhydroxy compounds and epoxy compounds.
4. The pressure-sensitive recording sheet of claim 1, wherein said polyamine adduct is an adduct formed between a polyamine and an epoxy compound.
5. The pressure-sensitive recording sheet of claim 1, wherein the polyurea is obtained from an isocyanate containing polyisocyanate adduct which has at least two uncombined isocyanate groups.
6. The pressure-sensitive recording sheet of claim 1, wherein the polyurea is obtained from a polyamine adduct which has at least two uncombined amine groups.
7. The pressure-sensitive recording sheet of claim 1, wherein the polyisocyanate is selected from the group consisting of dithioisocyanates, diisocyanates and triisocyanates.
8. The pressure-sensitive recording sheet of claim 1, wherein the polyisocyanate is a polyisocyanate monomer.
9. The pressure-sensitive recording sheet of claim 1, wherein the polyisocyanate per se or polyisocyanate used to form the adduct is selected from the group consisting of m-phenylene diisocyanate, p-phenylene diisocyanate, 2,6-tolylene diisocyanate, 2,4-tolylene diisocyanate, naphthalene-1,4-diisocyanate, diphenylmethane-4,4''-diisocyanate, 3,3''-dimethoxy-4,4''-biphenyl-diisocyanate, 3,3''-dimethyl diphenylmethane-4,4''-diisocyanate, xylylene-1,4-diisocyanate, xylylene-1,3-diisocyanate, 4,4''-diphenylpropane diisocyanate, trimethylene diisocyanata, hexamethylene diisocyanate, propylene-1,2-diisocyanate, butylene-1,2-diisocyanate, ethylidine diisocyanate, cyclohexylene-1,2-diisocyanate, cyclohexylene-1,4-diisocyanate, xylylene-1,4-diisothiocyanate, ethylidinne diisothiocyanate, hexamethylene dithioisocyanate, 4,4'',4''''-triphenylmethane triisocyanate, toluene-2,4,6-triisocyanate, polymethylene polyphenyl isocyanate, and 4,4''-dimethyldiphenyl methane-2,2'',5, 5''-tetraisocyanate.
10. The pressure-sensitive recording sheet of claim 1, wherein the polyamine per se or polyamine used to form the adduct is an aromatic amine having at least two free amino groups in the molecule.
11. The pressure-sensitive recording sheet of claim 1, wherein the polyamine per se or polyamine used to form the adduct is an aliphatic amine having at least two free amino groups in the molecule.
12. The pressure-sensitive recording sheet of claim 1, wherein the polyurea is obtained from a polyamine per se or the polyamine used to form the adduct is selected from the group consisting of o-phenylene diamine, p-phenylene diamine, diamino naphthalene, 1, 1,3-propylene napthalene or hexymethylene diamine.
13. The pressure-sensitive recording sheet of claim 1, wherein a polyisocyanate is reacted with the polyamine or the polyamine adduct.
14. The pressure-sensitive recording sheet of claim 1, wherein a isocyanate-containing polyisocyanate adduct is reacted with the polyamine or polyamine adduct.
15. The pressure-sensitive recording sheet of claim 1, wherein a polyamine is reacted with the polyisocyanate or the isocyanate-containing polyisocyanate adduct.
16. The pressure-sensitive recording sheet of claim 1, wherein a polyamine adduct is reacted with the polyisocyanate or isocyanate-containing polyisocyanate adduct.
17. The pressure-sensitive recording sheet of claim 3, wherein the compound is a polyamine.
18. The pressure-sensitive recording sheet of claim 3, wherein the compound is a polycarboxylic acid.
19. The pressure-sensitive recording sheet of claim 3, wherein the compound is a polythiol.
20. The pressure-sensitive recording sheet of claim 3, wherein the compound is a polyhydroxy compound.
21. The pressure-sensitive recording sheet of claim 3, wherein the compound is an epoxy compound.
22. The pressure-sensitive recording sheet of claim 3, wherein the compound is a polyol.
23. Pressure sensitive microcapsules containing a colorless color forming substance in an oily liquid encapsulated in walls of a polyurea produced by the reaction of a polyisocyanate or isocyanate-containing polyisocyanate adduct with a polyamine or polyamine adduct comprising: a. dissolving the polyisocyanate or isocyanate-containing polyisocyanate adduct in the oily liquid having dissolved therein the color forming substance; b. emulsifying the product of step (a) in a polar liquid; c. adding to the product of step (b) the polyamine or polyamine adduct; and d. subjecting the system of step (c) to polymerization conditions, whereby the oily liquid having dissolved therein the color forming substance is encapsulated in the polyurea product formed.
US298888A 1971-10-21 1972-10-19 Pressure-sensitive recording sheet with microcapsules having polyurea walls Expired - Lifetime US3900669A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP46083483A JPS4849509A (en) 1971-10-21 1971-10-21

Publications (2)

Publication Number Publication Date
US3900669A true US3900669A (en) 1975-08-19
US3900669B1 US3900669B1 (en) 1987-08-04

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ID=13803704

Family Applications (2)

Application Number Title Priority Date Filing Date
US298888A Expired - Lifetime US3900669A (en) 1971-10-21 1972-10-19 Pressure-sensitive recording sheet with microcapsules having polyurea walls
US00302047A Expired - Lifetime US3810209A (en) 1971-10-21 1972-10-30 Camera positioning apparatus

Family Applications After (1)

Application Number Title Priority Date Filing Date
US00302047A Expired - Lifetime US3810209A (en) 1971-10-21 1972-10-30 Camera positioning apparatus

Country Status (6)

Country Link
US (2) US3900669A (en)
JP (1) JPS4849509A (en)
BE (1) BE790373A (en)
DE (1) DE2251381A1 (en)
ES (1) ES407671A1 (en)
GB (1) GB1396543A (en)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4046741A (en) * 1976-02-17 1977-09-06 Stauffer Chemical Company Post-treatment of polyurea microcapsules
DE2808904A1 (en) * 1977-03-03 1978-09-07 Mead Corp METHOD OF MANUFACTURING PRESSURE-SENSITIVE CARBON-FREE COPY SHEET USING MICROCAPSULES FORMED IN SITU IN A RADIATION-CURABLE Binder
US4170483A (en) * 1975-08-28 1979-10-09 The Mead Corporation Process for the production of self-contained carbonless copy record sheets and coating composition for use therein
US4191404A (en) * 1977-03-03 1980-03-04 The Mead Corporation Process for producing a pressure-sensitive carbonless copy sheet using microcapsules formed in situ in a radiation curable binder
US4200667A (en) * 1977-03-03 1980-04-29 The Mead Corporation Process for producing a pressure-sensitive carbonless copy sheet using microcapsules formed in situ in a radiation curable binder
US4303719A (en) * 1980-07-29 1981-12-01 Vassiliades Anthony E Chromogenic copy system
US4321093A (en) * 1980-04-04 1982-03-23 The Standard Register Company Moisture-set color developer ink
US4324817A (en) * 1979-07-26 1982-04-13 Bayer Aktiengesellschaft Process for making carbonless copying paper
US4435340A (en) 1981-01-27 1984-03-06 Kanzaki Paper Manufacturing Company Limited Process for preparing microcapsules for pressure sensitive manifold paper
US4483974A (en) * 1982-08-18 1984-11-20 Bayer Aktiengesellschaft Process for the production of stabilized polyisocyanates, the polyisocyanates so-stabilized and their use in the production of polyurethanes
US4547429A (en) * 1983-09-17 1985-10-15 Cassella Aktiengesellschaft Encapsulated salts of acid particles wherein the salt particles are surrounded by a polyurethane/polyurea casing
US4847152A (en) * 1986-10-22 1989-07-11 Bayer Aktiengesellschaft Microcapsules with improved polyurea walls
US4877706A (en) * 1988-05-25 1989-10-31 Xerox Corporation Single component cold pressure fixable encapsulated toner compositions
US4891245A (en) * 1986-03-21 1990-01-02 Koh-I-Noor Rapidograph, Inc. Electrophoretic display particles and a process for their preparation
US4945121A (en) * 1987-08-18 1990-07-31 Koh-I-Noor Radiograph, Inc. Thermosetting dyed latex colorant dispersions
US4970031A (en) * 1988-06-02 1990-11-13 Nok Corporation Process for preparing microcapsules with controlled-release
US5204184A (en) * 1990-09-10 1993-04-20 The Standard Register Company Microencapsulation using tertiary aliphatic isocyanate capsule wall material
US5225118A (en) * 1990-08-15 1993-07-06 Boise Cascade Corporation Process for manufacturing polyurea microcapsules and product therefrom
US5330566A (en) * 1992-02-24 1994-07-19 Appleton Papers Inc. Capsule coating
DE102016006320A1 (en) 2016-05-25 2017-11-30 Carl Freudenberg Kg Fixable fabrics

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2738509A1 (en) * 1977-08-26 1979-03-08 Bayer Ag RESPONSE COPY
JPS6026039B2 (en) * 1977-09-05 1985-06-21 三菱製紙株式会社 Self-coloring pressure-sensitive recording paper
DE2753767C2 (en) * 1977-12-02 1987-01-22 Bayer Ag, 5090 Leverkusen Carbonless carbonless paper and process for its manufacture
GB2058111B (en) * 1979-06-08 1983-08-03 Kanzaki Paper Mfg Co Ltd Microcapsule dispersions
DE3020148A1 (en) * 1980-05-28 1981-12-03 Bayer Ag, 5090 Leverkusen CONCENTRATED MICROCAPSULE SUSPENSIONS FOR REACTION COPY PAPERS
JPS57140638A (en) * 1981-01-27 1982-08-31 Kanzaki Paper Mfg Co Ltd Preparation of microcapsule for pressure sensitive copy paper
JPS583898A (en) * 1981-06-30 1983-01-10 Kanzaki Paper Mfg Co Ltd Manufacture of microcapsule for pressure-sensitive copying paper
US4681806A (en) * 1986-02-13 1987-07-21 Minnesota Mining And Manufacturing Company Particles containing releasable fill material and method of making same
JPH0619555B2 (en) * 1986-03-10 1994-03-16 富士写真フイルム株式会社 Method for producing photosensitive microcapsules
CA2012585A1 (en) * 1989-04-14 1990-10-14 The Mead Corporation Preparing high solids cb printing composition by microencapsulation with printing vehicle as continuous phase
DE4130743A1 (en) * 1991-09-16 1993-03-18 Bayer Ag MICROCAPSULES MADE FROM ISOCYANATES WITH GROUPS CONTAINING POLYETHYLENE OXIDE
US5825502A (en) * 1996-10-09 1998-10-20 Teach Screen Software Gmbh Device for close-up photography of surfaces
US6639623B2 (en) 1999-12-23 2003-10-28 Hill-Rom Services, Inc. Controls for a surgical theater system
DE102008002145A1 (en) 2008-06-02 2009-12-03 Symrise Gmbh & Co. Kg Capsule with organic-inorganic hybrid wall

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3016308A (en) * 1957-08-06 1962-01-09 Moore Business Forms Inc Recording paper coated with microscopic capsules of coloring material, capsules and method of making
US3429827A (en) * 1962-11-23 1969-02-25 Moore Business Forms Inc Method of encapsulation
US3619238A (en) * 1968-07-15 1971-11-09 Fuji Photo Film Co Ltd Pressure sensitive copying paper
US3660304A (en) * 1968-06-04 1972-05-02 Fuji Photo Film Co Ltd Method of producing oily liquid-containing microcapsules

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1453843A (en) * 1921-09-22 1923-05-01 Roy W Johnston Focusing mechanism
US1837704A (en) * 1928-04-19 1931-12-22 Harrie J Dean Apparatus for photographing
US2282768A (en) * 1940-08-03 1942-05-12 Remington Rand Inc Copyholder for document photographing cameras
US2612824A (en) * 1950-08-09 1952-10-07 Jr Walter F Kroemmelbein Television photographic device

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3016308A (en) * 1957-08-06 1962-01-09 Moore Business Forms Inc Recording paper coated with microscopic capsules of coloring material, capsules and method of making
US3429827A (en) * 1962-11-23 1969-02-25 Moore Business Forms Inc Method of encapsulation
US3660304A (en) * 1968-06-04 1972-05-02 Fuji Photo Film Co Ltd Method of producing oily liquid-containing microcapsules
US3619238A (en) * 1968-07-15 1971-11-09 Fuji Photo Film Co Ltd Pressure sensitive copying paper

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4170483A (en) * 1975-08-28 1979-10-09 The Mead Corporation Process for the production of self-contained carbonless copy record sheets and coating composition for use therein
US4046741A (en) * 1976-02-17 1977-09-06 Stauffer Chemical Company Post-treatment of polyurea microcapsules
FR2341359A1 (en) * 1976-02-17 1977-09-16 Stauffer Chemical Co POST-TREATMENT OF POLYURIDE MICROCAPSULES
DE2808904A1 (en) * 1977-03-03 1978-09-07 Mead Corp METHOD OF MANUFACTURING PRESSURE-SENSITIVE CARBON-FREE COPY SHEET USING MICROCAPSULES FORMED IN SITU IN A RADIATION-CURABLE Binder
US4191404A (en) * 1977-03-03 1980-03-04 The Mead Corporation Process for producing a pressure-sensitive carbonless copy sheet using microcapsules formed in situ in a radiation curable binder
US4200667A (en) * 1977-03-03 1980-04-29 The Mead Corporation Process for producing a pressure-sensitive carbonless copy sheet using microcapsules formed in situ in a radiation curable binder
US4324817A (en) * 1979-07-26 1982-04-13 Bayer Aktiengesellschaft Process for making carbonless copying paper
US4321093A (en) * 1980-04-04 1982-03-23 The Standard Register Company Moisture-set color developer ink
US4303719A (en) * 1980-07-29 1981-12-01 Vassiliades Anthony E Chromogenic copy system
US4435340A (en) 1981-01-27 1984-03-06 Kanzaki Paper Manufacturing Company Limited Process for preparing microcapsules for pressure sensitive manifold paper
US4483974A (en) * 1982-08-18 1984-11-20 Bayer Aktiengesellschaft Process for the production of stabilized polyisocyanates, the polyisocyanates so-stabilized and their use in the production of polyurethanes
US4547429A (en) * 1983-09-17 1985-10-15 Cassella Aktiengesellschaft Encapsulated salts of acid particles wherein the salt particles are surrounded by a polyurethane/polyurea casing
US4891245A (en) * 1986-03-21 1990-01-02 Koh-I-Noor Rapidograph, Inc. Electrophoretic display particles and a process for their preparation
US4847152A (en) * 1986-10-22 1989-07-11 Bayer Aktiengesellschaft Microcapsules with improved polyurea walls
US4945121A (en) * 1987-08-18 1990-07-31 Koh-I-Noor Radiograph, Inc. Thermosetting dyed latex colorant dispersions
US4877706A (en) * 1988-05-25 1989-10-31 Xerox Corporation Single component cold pressure fixable encapsulated toner compositions
US4970031A (en) * 1988-06-02 1990-11-13 Nok Corporation Process for preparing microcapsules with controlled-release
US5225118A (en) * 1990-08-15 1993-07-06 Boise Cascade Corporation Process for manufacturing polyurea microcapsules and product therefrom
US5324584A (en) * 1990-08-15 1994-06-28 Boise Cascade Corporation Process for manufacturing polyurea microcapsules and product therefrom
US5204184A (en) * 1990-09-10 1993-04-20 The Standard Register Company Microencapsulation using tertiary aliphatic isocyanate capsule wall material
US5330566A (en) * 1992-02-24 1994-07-19 Appleton Papers Inc. Capsule coating
DE102016006320A1 (en) 2016-05-25 2017-11-30 Carl Freudenberg Kg Fixable fabrics

Also Published As

Publication number Publication date
US3900669B1 (en) 1987-08-04
ES407671A1 (en) 1976-02-16
BE790373A (en) 1973-02-15
DE2251381A1 (en) 1973-04-26
US3810209A (en) 1974-05-07
JPS4849509A (en) 1973-07-12
GB1396543A (en) 1975-06-04

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RR Request for reexamination filed

Effective date: 19860811

B1 Reexamination certificate first reexamination