US3836383A - Pressure sensitive recording paper - Google Patents

Pressure sensitive recording paper Download PDF

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Publication number
US3836383A
US3836383A US00193151A US19315171A US3836383A US 3836383 A US3836383 A US 3836383A US 00193151 A US00193151 A US 00193151A US 19315171 A US19315171 A US 19315171A US 3836383 A US3836383 A US 3836383A
Authority
US
United States
Prior art keywords
sensitive recording
recording paper
pressure sensitive
paper
color
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
US00193151A
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English (en)
Inventor
M Kiritani
H Matsukawa
M Aoki
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
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=14122264&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US3836383(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
Application granted granted Critical
Publication of US3836383A publication Critical patent/US3836383A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
    • Y10T428/24835—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including developable image or soluble portion in coating or impregnation [e.g., safety paper, etc.]
    • 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]

Definitions

  • ABSTRACT A pressure-sensitive recording paper comprising a support having coated thereon a layer of color former, said color former dissolved in at least one compound represented by the following formula:
  • This invention relates to a pressure-sensitive recording paper. More particularly, it relates to a pressuresensitive recording paper using a compound, in which two alkyl-substituted benzene nuclei are connected with each other through the unit 4C,,H as a solvent for a color former:
  • n is an integer of from 1 to 8
  • R and R each is an alkyl group having one to eight carbon atoms or a hydrogen atom
  • p and q each is the number of alkyl groups
  • p q being an integer of 1-3
  • R and R may be the same.
  • the object of the present invention is to obtain a pressure-sensitive recording paper having no unpleasant smell and toxicity, and capable of forming a color image having a higher density without giving a color fog.
  • pressure-sensitive recording paper there are those comprising so-called upper paper prepared by dissolving a substantially colorless compound (hereinafter referred to as a color former) in an organic solvent, encapsulating it, and then coating the capsules onto a support; lower paper prepared by coating a color-developing material (hereinafter referred to as a color developer), which is capable of forming colored images, onto another support; and, in some cases, middle paper prepared by coating capsules containing a color former onto one side of a support and a color developer onto the other side thereof, or those containing said capsules and a color developer onto the same side of a support.
  • a color former substantially colorless compound
  • a color developer a color-developing material
  • color is developed by locally pressing in such a way that the capsule layer comes into contact with the color developer layer to decompose the capsules located at the pressed part and to cause reaction between the color former and the color developer.
  • a pressure sensitive recording paper having capsules and a color developer agent on the same surface thereof is used. color will be developed by pressing in the same way.
  • active clay materials such as acid clay, active zeolite and bentonite
  • organic acidic materials such as succinic acid, tannic acid, gallic acid, pentachlorphenol and phenol resin are generally used.
  • malachite green lactone benzoyl leucomethylene blue, crystal violet lactone, rhodamine B lactom, 3-dialkylamino-7- alkylfluorans, 3-methyl-2,2- spirobi(benzo[f]chromene), etc. are used.
  • conditions (a)-(e) are especially of importance and, if one of these conditions is not satisfied, the solvent cannot be used as a solvent for a color former.
  • ethers do not satisfy the conditions of (a) and (d)
  • alcohols do not satisfy the conditions of (a), (c) and (d)
  • paraffins do not satisfy the conditions of (a)
  • ketones, esters, olefins and amines do not satisfy the conditions of (d)
  • organic acids do not satisfy the conditions of (c)
  • usual aromatic hydrocarbons do not satisfy the conditions of (a), (g) and (h).
  • the pressure-sensitive recording paper wherein low chlorinated trichlorodiphenyl and tetrachlorodiphenyl are used, has the defect of having an unpleasant smell.
  • the pressure sensitive recording paper wherein highly chlorinated pentachlorodiphenyl and hexachlorodiphenyl are used, has the defect in that the effusion thereof is difficult to be freely done due to their high viscosity and that sufficient color density cannot be obtained, while they have less of an unpleasant smell.
  • the pressure-sensitive recording paper wherein the mixture of chlorinated diphenyl with a low chlorination degree and the same with high chlorination degree is used is a little more improved in the smell than that wherein chlorinated diphenyl with low chlorination degree is used separately and, in the density of the color formed, the former is a little more improved than that wherein highly chlorinated diphenyl is used independently, but the former has still considerable unpleasant smell and the density of color formed is not sufficient.
  • chlorinated diphenyl is slightly decomposed by light to form hydrogen chloride.
  • the capsule coated sheet wherein chlorinated diphenyl is used has the defect that, when it is exposed to light for a long time, the generated hydrogen chloride will be reacted with the color former to cause colored fog. Furthermore, this capsule coated sheet wherein the colored fog took place has less color developing ability onto the lower paper, and a sufficient density of the color formed cannot be obtained. Besides, chlorinated diphenyl has appreciable toxicity to human beings and animals.
  • the conventional pressure sensitive recording paper wherein chlorinated diphenyl is used has had the defects that it has unpleasant smell, that sufficient density of the color formed cannot be obtained, that when exposed to light for a long time, colored fog on capsule coated sheet and the lowering of the color developing ability thereof to the lower paper take place, and that it has a problem in its toxicity.
  • the present invention is characterized in that, in the pressure sensitive recording paper, the compound represented by the general formula (I) is used as a solvent for the color former, separately or in combination with other solvents.
  • the compound (I) in this invention is characterized in that two alkyl substituted benzene nuclei are connected with each other through a -(-C,,H bond and, as is different from the usual aromatic compounds, the compound (I) of the present invention has a considerably high boiling point, does not vaporize off in a heat drying process or in a place of the elevated temperature, has no unpleasant smell, and in addition, it has no toxicity to human beings and animals.
  • the reason why the number of the carbon atoms contained in R and R, and that in the (-C,,H existing between the two benzene nuclei is not more than 8 and 8, respectively, is that, when the number of the carbon atoms contained in R and R becomes not less than 9 and n becomes not less than 9, the viscosity thereof conspicuously increases and the solubility of a color former thereto decreases, which is not desirable.
  • the compound of this invention having a particularly restricted structure, satisfies the aforesaid conditions of (a)(e) demanded for a solvent for the color former of pressure sensitive recording paper.
  • it has the excellent advantages that there is little rise in viscosity, even at a low temperature, that it has no unpleasant smell or toxicity to human beings and animals, that it raises the stability of the capsule coated sheet to light, that, even when the capsule coated sheet is exposed to light for a long time, the colored fog of the sheet is remarkably less compared with conventional ones, that the color developing ability in developing this capsule coated sheet onto the lower paper does not decrease like the conventional ones, and the like.
  • the pressure sensitive recording paper of this invention is excellent also in that it has a higher density with respect to the color formed compared with conventional pressure sensitive recording paper, wherein chlorinated diphenyl is used. Therefore, it can be said that the compound (I) used in the present invention having a particularly restricted structure is extremely excellent as a solvent for a color former of pressure sensitive recording paper.
  • the compound of the general formula (I) of the present invention may be used in combination with other solvents.
  • solvents to be mixed together there are petroleum fractions such as liquid paraffin, kerosene, naphtha, etc., synthesized oils, such as chlorinated paraffin, chlorinated diphenyl, hexahydroterphenyl, alkylnaphthalenes, alkylated polyphenyls, etc., and vegetable oils, such as cotton seed oil, linseed oil, etc.
  • solvents are mixed and used together in order to adjust the viscosity, to control the solubility of a color former, and to increase the quantity for the reduction of cost, etc.
  • This invention is characterized by using the compound of the general formula (I) having a particularly restricted structure as a solvent for a color former of pressure sensitive recording paper and, accordingly, all of the publicly known art can be applied as a method or process for encapsulating this solvent. Therefore, the present invention is not restricted by the method or process for the encapsulation.
  • a clay paper (lower paper) prepared as follows. That is, g of sulfuric acid processed acidic terra abla was dispersed in 280 g of water containing 6 g of 40 percent sodium hydroxide aqueous solution using homogenizer. Thereafter, 50 g ofa 10 percent aqueous solution of sodium salt of casein and 30 g of a styrene butadiene latex (trade name: Dow Latex 626, made by Dow Chemical Co.), were added thereto as a binder, and coated on a paper by air knife coating, and dried to obtain the clayed paper.
  • a styrene butadiene latex trade name: Dow Latex 626, made by Dow Chemical Co.
  • Example 2 Example 2
  • the upper paper thus obtained had no unpleasant smell like that of the conventional pressure sensitive recording paper.
  • This upper paper was superposed on a clay paper and writing was conducted with pressure, there was developed red image on a clay paper in a moment.
  • the density of color developed image was remarkably high compared with that of the conventional recording paper wherein chlorinated diphenyl was used. Besides, even when this upper paper was exposed to sun light for a long time, the lowering in the color developing ability and fog were not observed.
  • Example 1 20 g of paraffin containing l0-l2 carbon atoms, treated in the same was as in Example 1 to obtain upper paper.
  • the upper paper for pressure sensitive recording paper thus obtained had no unpleasant smell like that of the conventional pressure sensitive recording paper prepared by the analogous treatment using chlorinated diphenyl.
  • this upper paper was superposed on a clay paper and writing was conducted with pressure, there was developed a red image on a clay paper.
  • the density of this color developed image was remarkably high compared with that of the conventional pressure sensitive recording paper wherein chlorinated diphenyl CaHn was used.
  • this upper paper was exposed to sun light for a long time, the lowering in the color developing ability and colored fog were not observed.
  • the capsule solution thus obtained was coated on a paper by way of roll coating, then dried.
  • the upper paper obtained in this way did not have the unpleasant smell like that of the conventional pressure sensitive recording paper obtained by the analogous treatment using chlorinated diphenyl.
  • This upper paper was superposed on a clay paper and writing was conducted, there was developed a blackish green image on a clay paper.
  • the density of this color developed image was remarkably high compared with that of the conventional pressure sensitive recording paper wherein chlorinated diphenyl was used. Furthermore, even when this upper paper was exposed to sun light for a long time, the lowering in the color developing ability and colored fog were not observed.
  • Example 1 was duplicated using 2-methyl-5-isopropyldiphenylmethane (having a boiling point of 307 3 lOC and specific gravity of 09916 at 20C) instead of 2,4-dimethyldiphenylmethane, and using 3-methyl- 2,2-spirobi(benzo[ flchromene) instead of crystal violet lactone. The result thereof was the same as in Example 1.
  • Example 1 was duplicated, except that 1,1-diphenyll-heptylmethane (having a boiling point of l43-l45C/0.l mml-lg, a melting point of to --4C and a specific gravity of 0.9444 at 20C) was used instead of 2 ,4-dimethyldiphenylmethane. The result thereof was the same as in Example 1.
  • R and R each represent a member selected from the group consisting of alkyl groups containing one to eight carbon atoms, and a hydrogen atom
  • p and q represent the number of alkyl groups
  • p q being an integer of 1 to 3
  • R and R may be the same.
  • Example 9 Example 1 was duplicated, except that dimethyl-tbutyldiphenylmethane (mixture of several kinds of isomers, having a boiling point of l3 2l 48C/0.l mmHg) 3.
  • the pressure sensitive recording paper of claim 1 wherein said compound is used as a mixture with a solvent selected from the group consisting of a petroleum fraction, a synthetic oil and a plant oil.
  • the pressure sensitive recording paper of claim 3, wherein said synthetic oil is a member selected from the group consisting of chlorinated paraffin, chlorinated diphenyl, hexahydroterphenyl, alkylnaphthalenes and alkylated polyphenyls.

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  • Color Printing (AREA)
US00193151A 1970-10-27 1971-10-27 Pressure sensitive recording paper Expired - Lifetime US3836383A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP45094877A JPS492126B1 (enrdf_load_stackoverflow) 1970-10-27 1970-10-27

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US06/724,186 Reissue USRE33113E (en) 1970-10-27 1976-09-17 Pressure sensitive recording paper

Publications (1)

Publication Number Publication Date
US3836383A true US3836383A (en) 1974-09-17

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ID=14122264

Family Applications (2)

Application Number Title Priority Date Filing Date
US00193151A Expired - Lifetime US3836383A (en) 1970-10-27 1971-10-27 Pressure sensitive recording paper
US06/724,186 Expired - Lifetime USRE33113E (en) 1970-10-27 1976-09-17 Pressure sensitive recording paper

Family Applications After (1)

Application Number Title Priority Date Filing Date
US06/724,186 Expired - Lifetime USRE33113E (en) 1970-10-27 1976-09-17 Pressure sensitive recording paper

Country Status (6)

Country Link
US (2) US3836383A (enrdf_load_stackoverflow)
JP (1) JPS492126B1 (enrdf_load_stackoverflow)
DE (1) DE2153634C3 (enrdf_load_stackoverflow)
ES (1) ES396370A1 (enrdf_load_stackoverflow)
GB (1) GB1346364A (enrdf_load_stackoverflow)
IE (1) IE36768B1 (enrdf_load_stackoverflow)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3936566A (en) * 1971-03-02 1976-02-03 Nippon Petrochemicals Company Ltd. Pressure sensitive record material employing diaryl alkane solvents
US3939095A (en) * 1972-08-10 1976-02-17 Badische Anilin- & Soda-Fabrik Aktiengesellschaft Dye-containing microcapsules
US3996405A (en) * 1973-01-24 1976-12-07 Ncr Corporation Pressure-sensitive record material
US4130299A (en) * 1977-09-12 1978-12-19 Monsanto Company Low-odor dye solvents for pressure-sensitive copying systems
US4275906A (en) * 1979-07-18 1981-06-30 Diamond Shamrock Corporation Pressure sensitive recording sheets
US4289806A (en) * 1979-01-27 1981-09-15 Nippon Petrochemicals Company, Limited Pressure-sensitive recording material
US4335013A (en) * 1979-08-24 1982-06-15 Monsanto Company Solvents useful in pressure-sensitive mark-recording systems
US4343652A (en) * 1979-08-24 1982-08-10 Monsanto Europe S.A. Chromogen solutions for pressure-sensitive mark-recording systems
US4383706A (en) * 1979-08-31 1983-05-17 Kureha Kagaku Kogyo Kabushiki Kaisha Pressure-sensitive recording paper
US4383705A (en) * 1981-01-13 1983-05-17 Kureha Kagaku Kogyo Kabushiki Kaisha Pressure-sensitive recording material
US4390194A (en) * 1980-06-25 1983-06-28 Nippon Petrochemicals Company, Limited Recording material
US4489017A (en) * 1979-07-26 1984-12-18 Bayer Aktiengesellschaft Spray drying of microcapsule dispersions
USRE32162E (en) * 1971-03-02 1986-05-27 Nippon Petrochemicals Co., Ltd. Pressure sensitive record material employing diaryl alkane solvents
US4686548A (en) * 1984-06-21 1987-08-11 Nippon Petrochemicals Company, Limited Pressure-sensitive recording material
US5877362A (en) * 1996-09-12 1999-03-02 Nippon Petrochemicals Company, Limited Method for producing diphenylmethane
US5880322A (en) * 1996-12-16 1999-03-09 Nippen Petrochemicals Company, Limited Method for producing diarylmethane
US6207866B1 (en) 1997-07-11 2001-03-27 Nippon Petrochemicals Company, Limited Method for producing diarylmethane or its derivatives
US6300534B1 (en) 1998-07-01 2001-10-09 Nippon Petrochemicals Company, Limited Process for producing dehydrogenated compounds of m-ethyldiphenylalkane
US6586362B1 (en) 1999-09-20 2003-07-01 Nippon Petrochemicals Company, Limited Hydrocarbon solvent and pressure-sensitive copying material made with the same

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4921217A (enrdf_load_stackoverflow) * 1972-06-15 1974-02-25
JPS5738436B2 (enrdf_load_stackoverflow) * 1973-08-23 1982-08-16
IT1136651B (it) * 1981-06-04 1986-09-03 Caffaro Spa Ind Chim Solvente per coloranti in carte autocopianti
ES2015528B3 (es) * 1985-12-26 1990-09-01 Nippon Petrochemicals Co Ltd Material de copia sensible a la presion.
JPH074986B2 (ja) * 1986-05-26 1995-01-25 富士写真フイルム株式会社 感熱記録材料
DE3781259D1 (de) * 1986-12-25 1992-09-24 Fuji Photo Film Co Ltd Verfahren zur herstellung eines waermeempfindlichen aufzeichnungsmaterials.
JP2946233B2 (ja) * 1990-07-10 1999-09-06 日本石油化学株式会社 感圧複写材料

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3009760A (en) * 1961-11-21 Process for coloring shaped struc-
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
GB915342A (en) * 1959-03-19 1963-01-09 Hoechst Ag Process for dyeing fibres
US3625736A (en) * 1967-10-27 1971-12-07 Fuji Photo Film Co Ltd Pressure-sensitive copying unit containing granular resinous material and method of making
US3627581A (en) * 1970-10-19 1971-12-14 Ncr Co Pressure-sensitive record material
US3649649A (en) * 1967-07-10 1972-03-14 Nisso Kako Co Ltd Fluoran derivatives and preparation thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3069478A (en) * 1960-03-01 1962-12-18 Socony Mobil Oil Co Inc Aralkylation of aromatics with styrenes
CA986714A (en) * 1971-03-02 1976-04-06 Yoshiaki Aida Pressure-sensitive record material employing diaryl alkane solvents

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3009760A (en) * 1961-11-21 Process for coloring shaped struc-
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
GB915342A (en) * 1959-03-19 1963-01-09 Hoechst Ag Process for dyeing fibres
US3649649A (en) * 1967-07-10 1972-03-14 Nisso Kako Co Ltd Fluoran derivatives and preparation thereof
US3625736A (en) * 1967-10-27 1971-12-07 Fuji Photo Film Co Ltd Pressure-sensitive copying unit containing granular resinous material and method of making
US3627581A (en) * 1970-10-19 1971-12-14 Ncr Co Pressure-sensitive record material

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE32162E (en) * 1971-03-02 1986-05-27 Nippon Petrochemicals Co., Ltd. Pressure sensitive record material employing diaryl alkane solvents
US3936566A (en) * 1971-03-02 1976-02-03 Nippon Petrochemicals Company Ltd. Pressure sensitive record material employing diaryl alkane solvents
US3939095A (en) * 1972-08-10 1976-02-17 Badische Anilin- & Soda-Fabrik Aktiengesellschaft Dye-containing microcapsules
US3996405A (en) * 1973-01-24 1976-12-07 Ncr Corporation Pressure-sensitive record material
US4130299A (en) * 1977-09-12 1978-12-19 Monsanto Company Low-odor dye solvents for pressure-sensitive copying systems
FR2402535A1 (fr) * 1977-09-12 1979-04-06 Monsanto Co Solvants a faible odeur a base de xylene benzyle pour matieres colorantes, pour des systemes de copie sensibles a la pression
US4289806A (en) * 1979-01-27 1981-09-15 Nippon Petrochemicals Company, Limited Pressure-sensitive recording material
US4275906A (en) * 1979-07-18 1981-06-30 Diamond Shamrock Corporation Pressure sensitive recording sheets
US4489017A (en) * 1979-07-26 1984-12-18 Bayer Aktiengesellschaft Spray drying of microcapsule dispersions
US4335013A (en) * 1979-08-24 1982-06-15 Monsanto Company Solvents useful in pressure-sensitive mark-recording systems
US4343652A (en) * 1979-08-24 1982-08-10 Monsanto Europe S.A. Chromogen solutions for pressure-sensitive mark-recording systems
US4383706A (en) * 1979-08-31 1983-05-17 Kureha Kagaku Kogyo Kabushiki Kaisha Pressure-sensitive recording paper
EP0029645B1 (en) * 1979-08-31 1983-07-20 Kureha Kagaku Kogyo Kabushiki Kaisha Use of diphenylethane derivative as solvent for colour-former in pressure-sensitive recording materials; solutions, microcapsules, sheets coated with microcapsules and pressure-sensitive recording materials containing said solvent; method of copying using said sheets or recording materials
US4390194A (en) * 1980-06-25 1983-06-28 Nippon Petrochemicals Company, Limited Recording material
US4383705A (en) * 1981-01-13 1983-05-17 Kureha Kagaku Kogyo Kabushiki Kaisha Pressure-sensitive recording material
US4686548A (en) * 1984-06-21 1987-08-11 Nippon Petrochemicals Company, Limited Pressure-sensitive recording material
US5877362A (en) * 1996-09-12 1999-03-02 Nippon Petrochemicals Company, Limited Method for producing diphenylmethane
US5880322A (en) * 1996-12-16 1999-03-09 Nippen Petrochemicals Company, Limited Method for producing diarylmethane
US6207866B1 (en) 1997-07-11 2001-03-27 Nippon Petrochemicals Company, Limited Method for producing diarylmethane or its derivatives
US6300534B1 (en) 1998-07-01 2001-10-09 Nippon Petrochemicals Company, Limited Process for producing dehydrogenated compounds of m-ethyldiphenylalkane
US6586362B1 (en) 1999-09-20 2003-07-01 Nippon Petrochemicals Company, Limited Hydrocarbon solvent and pressure-sensitive copying material made with the same

Also Published As

Publication number Publication date
ES396370A1 (es) 1974-05-01
JPS492126B1 (enrdf_load_stackoverflow) 1974-01-18
DE2153634B2 (de) 1973-09-06
DE2153634C3 (de) 1980-02-21
USRE33113E (en) 1989-11-14
DE2153634A1 (de) 1972-05-10
IE36768B1 (en) 1977-02-16
GB1346364A (en) 1974-02-06

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