EP0057740A1 - Papiers copiants sensibles à la pression - Google Patents

Papiers copiants sensibles à la pression Download PDF

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Publication number
EP0057740A1
EP0057740A1 EP81100898A EP81100898A EP0057740A1 EP 0057740 A1 EP0057740 A1 EP 0057740A1 EP 81100898 A EP81100898 A EP 81100898A EP 81100898 A EP81100898 A EP 81100898A EP 0057740 A1 EP0057740 A1 EP 0057740A1
Authority
EP
European Patent Office
Prior art keywords
solvent
color former
pressure sensitive
sensitive recording
weight
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.)
Withdrawn
Application number
EP81100898A
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German (de)
English (en)
Inventor
Grannis Samuel Johnson
Ira Marvin Rose
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.)
Diamond Shamrock Corp
Original Assignee
Diamond Shamrock Corp
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
Application filed by Diamond Shamrock Corp filed Critical Diamond Shamrock Corp
Priority to EP81100898A priority Critical patent/EP0057740A1/fr
Publication of EP0057740A1 publication Critical patent/EP0057740A1/fr
Withdrawn legal-status Critical Current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

Definitions

  • This invention relates to pressure sensitive recording sheets.
  • a first sheet generally paper
  • a coating of microcapsules containing a solution of color former is treated on one side with a coating of microcapsules containing a solution of color former.
  • a second sheet is treated on one side with a developer (coreactant material) such as acidic clay or polymeric material.
  • a developer coreactant material
  • the coated side of both sheets are brought into contact with each other and pressure applied to the first sheet, e.g., by pencil, pen or typewriter, the microcapsules are ruptured and the color former is released and comes into contact with the second sheet containing the developer.
  • a color is produced by reaction between the color former and the developer.
  • Patent No. 3,836,383 - Kiritani et al - September 17, 1974 discloses as the solvent two alkyl substituted benzene nuclei connected by -CnH2n - and -CH(CH 3)-.
  • Patent No. 3,936,566 - Sato et al - February 3, 1976 discloses as the solvent the reaction product of styrene and alkyl substituted aromatic hydrocarbons.
  • Patent No. 4,130,299 - Wygant - December 19, 1978 discloses benzylated xylenes as the solvent.
  • Pressure sensitive recording sheets are prepared wherein the color former is dissolved in a solvent which is one or a mixture of alkoxy diphenyl'alkanes having the following structure: where R 1 , R 2 , R 3 and R 4 are H or a straight or branched chain alkyl group of 1 to 8 carbon atoms and can be the same or different; R 5 is a straight or branched chain alkyl group of 1 to 9 carbon atoms; R 6 is a straight or branched chain alkyl group of 1 to 8 carbon atoms; x is 0, 1 or 2; y is I or 2 and n is 1 or 2, with the proviso that the sum of the carbon atoms in R 1 , R 23 R 3 , R 4 , R 5 and R 6 does not exceed 9 and with the further proviso that where the alkoxy diphenyl alkane is a solid to viscous liquid, at least one diluent or at least one other generally liquid solvent.or mixture thereof is present.
  • a solvent which
  • R substituents are alkyl, they may be straight or branched chain such as methyl, ethyl, . n-propyl, isopropyl, n-butyl , isobutyl, secondary butyl, tertiary butyl,
  • the solvent there can be dissolved in the solvent from about 1 per cent by weight to about 10 per cent by weight, usually from about 2 percent by weight to about 5 per cent by weight, of the color former based on the weight of the solvent.
  • the solution of color former e.g., in the form of microcapsules, is applied to one surface of a sheet, which surface is brought into contact with the surface of a second sheet containing the developer.
  • the first sheet which is coated with the color former is further coated with the developer..
  • the color former upon the application of pressure, e.g., by pencil, pen or typewriter, the color former is released, e.g., by rupture of the microcapsules, so that it comes into contact with the developer whereupon color is produced.
  • the solvents for the color former are one or a mixture of alkoxy diphenyl alkanes having the following structure: where R 1 , R 2 , R 3 and R 4 are H or a straight or branched chain alkyl group of 1 to 8 carbon atoms and can be the same or different; R S is a straight or branched chain alkyl group of 1 to 9 carbon atoms; R6 is a straight or branched chain alkyl group of 1 to 8 carbon atoms; x is 0, 1 or 2; y is 1 or 2 and n is 1 or 2, with the proviso that the sum of the carbon atoms in R 1 , R 2 , R 3 , R 4 , R 5 and R 6 does not exceed 9 and with the further proviso that where the alkoxy diphenyl alkane is a solid to viscous liquid, at least one diluent or at least one other generally liquid solvent or mixture thereof is present.
  • R substituents are alkyl, they may be straight or branched chain such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secondary butyl, tertiary butyl, n-pentyl, neopentyl, hexyl, heptyl, 2-ethyl hexyl, n-octyl or nonyl.
  • alkoxy diphenyl alkanes are one or a mixture of: the methyl ether of styrenated phenol; the methyl ether of distyrenated phenol; the n-butyl ether of styrenated phenol; the n-butyl ether of distyrenated phenol; the n-propyl ether of styrenated phenol; the methyl ether of alpha methyl styrenated phenol; 2-methoxy diphenyl methane (m.p.
  • the undesirable phenolic odor is eliminated and replaced by a more tolerable ether odor, the reactivity with the color former has been eliminated by blocking the phenolic hydroxyl and the viscosity is reduced.
  • Another advantage of the use of alkoxy diphenyl alkanes as solvents is that where the solution of color former and solvent has water present such as the water present from the encapsulation procedure, the solvent vapor pressure is reduced by hydrogen bonding of water with the ether oxygen of the solvent. This brings about a reduction of odor. Water can be present in an amount up to the solubility limit of the water in the solution of solvent and color former.
  • alkoxy diphenyl alkanes can be prepared by known methods, many of these compounds and their preparations being reported in the literature. Where the alkoxy diphenyl alkanes are prepared in part from styrene or alpha methyl styrene, the following two routes can be employed.
  • One route involves reaction between styrene or alpha-methyl styrene and phenol or cresol (ortho, meta, para or mixtures) in the presence of an acid catalyst to form styrenated phenol or substituted styrenated phenol.
  • the styrene and the phenol or cresol are reacted in a mole ratio of about 1 to 2:1 to 4. This is followed by alkylation of the styrenated phenol to give the corresponding ether.
  • Alkylation (ether formation) can be achieved by reaction of the styrenated phenol with alkyl halides or alkyl sulfates in the presence of sodium hydroxide.
  • Useful Useful alkyl sulfates are dimethyl sulfate and diethyl sulfate. Ether formation can also be achieved by the acid catalyzed addition of styrenated phenol to olefins such as ethylene, propylene, isobutylene, butene-1, pentenes, hexenes and heptenes.
  • the phenol or cresol can be converted to the ether derivative by either of the alkylation procedures described above.
  • the resulting ether is then reacted with styrene or alpha-methyl styrene.
  • the pressure-sensitive recording sheets utilizing the improved solvents of the present invention may be prepared according to well-known, conventional procedures. Descriptions of methods for preparing the first sheet which contains the color former and the second sheet containing the developer or the single sheet containing both color former and developer on the same side of the sheet or containing the color former and developer on opposite sides of the same sheet are to be found in the literature- and such methods do not constitute a part of the present invention. Similarly, formation and application of microcapsules of color former and solvent or color former and solvent dispersed in a binder onto a sheet is fully disclosed in the literature. The solvents of this invention replace the conventional solvents in order to produce improved pressure-sensitive copying systems.
  • alkoxy diphenyl alkanes are solids to viscous liquids. However, in many instances, preparation without purification generally will yield liquid materials. Be that as it may, alkoxy diphenyl alkanes which are liquids at room temperature may be used alone,with diluents or even with known solvents which are generally liquids or with mixtures of the foregoing.
  • Alkoxy diphenyl alkanes which are solids, semisolids or viscous liquids at room temperature must be used in combination with.another generally liquid solvent which can be alkoxy diphenyl alkane or known solvent or with diluents or with mixtures of the foregoing in order to provide a mixture having the equisite degree of liquidity for use in pressure-sensitive recording systems.
  • the term "diluent” includes inert or substantially inert materials which are of little practical use alone as dye solyents, either because they have poor solvating power for the color former or because they act in some way to inhibit the development of color. Further, a diluent should not be selected which worsens the odor.
  • one part by weight of alkoxy diphenyl alkane may be admixed with from 0 to about three parts by weight of diluent for each part of solvent. Where the alkoxy diphenyl alkane is solid to viscous liquid, the minimum amount of diluent is that amount required to provide the requisite degree of liquidity.
  • Useful diluents are one or a mixture of mineral or vegetable oils, such as kerosene, paraffin oil, mineral spirits, neatsfoot oil, sperm oil, lard oil, olive oil, soybean oil, cottonseed oil, coconut oil, or rapeseed oil, or an organic aryl compound such as aromatic naphtha or Cl-12 alkyl benzene.
  • Monoalkylbenzene mixtures sometimes called “alkylates" are particularly useful as diluents with dye solvents of this invention.
  • alkylates are commercially available as intermediates for the manufacture of anionic liquid and solid detergents. Typical is a mono-C10 to C 15 alkylbenzene mixture.
  • the diluents referred to herein function to alter physical properties of the solvent such as viscosity or vapor pressure as may be desired for handling or processing considerations or for imparting the requisite degree of liquidity.
  • the diluents may also serve to reduce the total cost of the solvent in the system.
  • the solvents may also contain certain additives specifically intended to alter or control the final properties of the fluid, as for example viscosity control agents, vapor pressure control agents, freezing point depressants, antioxidants, and the like.
  • the total quantity of known solvent plus alkoxy diphenyl alkane when used with the color former should fall within the ranges heretofore set for the alkoxy diphenyl alkane alone.
  • the solvents of the present invention are utilized in combination with one or more color formers of normally colorless form.
  • Color formers which react with the developer to produce color when used in the present invention are not especially limited'and any conventional color former can be employed.
  • Representative examples of these color formers are: triarylmethane compounds such as 3,3-bis (p-dimethylaminophenyl)-6-dimethylaminophthalide, i.e., Crystal Violet Lactone, 3,3-bis(p-dimethyl- aminopheny1)phtha1ide, 3-(p-dimethylaminophenyl)-3-(1,2-dimethyl indol-3-yl) phthalide, 3-(p-dimethylaminophenyl)-3-(2-methylindol-3-yl)phthalide, 3-(p-dimethylaminophenyl)-3-(2-phenylindol-3-yl)phthalide, 3,3-bis(1,2-dimethyl- indol-3-yl
  • the color formers listed above produce color when the color former is brought into contact with acidic developers. Of course, other color formers that produce color by other mechanisms can be used as well. It is only necessary that the appropriate developer is used.
  • the developer or coreactant material can be any conventional material useful for this purpose.
  • Useful developers for the preceding color formers are acidic materials such as acidic clays and acidic polymeric materials. Examples are inorganic acidic materials such as bentonite, zinc oxide, kaolin, clay, active clay, acid clay, zeolite, bentonite, attapulgite, talc, colloidal silica, etc.
  • acidic polymers such as phenolaldehyde resin, maleic acid-rosin, hydrolysis product of styrenemaleic anhydride copolymers, hydrolysis product of ethylene-maleic anhydride copolymer, carboxypolyethyl- ene, hydrolysis product of vinyl methyl ether-maleic anhydride copolymer, etc.
  • the color former can be microencapsulated or dispersed in a binder by known means and.applied to a support such as a sheet which t can be paper, resin coated paper or plastic.
  • the developer can be applied as an outer layer to the same or applied to a different support or sheet which is positioned with its developer side against the color former.
  • the color former and developer can be applied to opposite sides of the same sheet as in the case where a plurality of sheets are used together, Here, the color former on one sheet is positioned against the developer of another sheet.
  • a 60 gallon stainless steel reactor, equipped with impeller, condenser, receiver and splitter was charged with 302.7 pounds (2.8 moles) of anisole.
  • the reactor was blanketed with nitrogen. Borontrifluoride etherate, 1.7 pounds was then charged into the reactor.
  • Temperature of the reactor was raised to 120°C.
  • Styrene 145.6 pounds (1.4 moles) was pumped into the reactor during 1-2 hours while maintaining temperature at 120 - 125°C. This temperature was held until a refractive index (25°C) of 1.5490 was attained indicating that all of the styrene had reacted.
  • the reactor was cooled to 90°C. Then 1.4 pounds of 28% aqueous ammonia were charged to the reactor.
  • the equipment was set for vacuum distillation and unchanged anisole was distilled off at 4-5 inches
  • Styrenated phenol 500 grams (2.5 moles), which was principally a mixture of 80 - 82% by weight monostyrenated phenol (a mixture of 2-(1-phenyl ethyl) phenol, 3-(1-phenyl ethyl) phenol and 4-(1-phenyl ethyl) phenol), and 18 - 20% by weight of distyrenated phenol were charged into a steel reactor equipped with stirrer, thermometer, dropping funnel and distilling head connected to a condenser. Temperature of the reactor was raised to 130°C. Then 140 grams (2.5 moles) of potassium hydroxide as a 45% aqueous solution was added dropwise while allowing water to distill off.
  • monostyrenated phenol a mixture of 2-(1-phenyl ethyl) phenol, 3-(1-phenyl ethyl) phenol and 4-(1-phenyl ethyl) phenol
  • Anisole 189 grams (1.75 moles), was charged into a glass reactor, equipped with stirrer, thermometer, condenser and dropping funnel. The reactor was blanketed with nitrogen. Borontrifluoride etherate, 1 ml, was charged into the reactor. Temperature of the reactor was raised to 125°C. Alpha-methyl styrene, 109.3 grams (0.926 moles), was added dropwise at 125°C. Temperature of the reactor was maintained at 125°C until refractive index was constant (1.5511). This required about 2 hours. After cooling to 70°C, 3 ml of 28% aqueous ammonia solution was added. Unchanged anisole was distilled off under vacuum (100 mm) allowing reactor temperature to reach 150°C.
  • the reactor was cooled to room temperature and the product filtered. 92 Grams of recovered anisole and 197 grams of product, composed chiefly of 2-and 4-(1-methyl-1-phenyl ethyl) methoxy benzene was obtained. Refractive index, 25°C, 1.5692, viscosity, 25°C, 21 centipoises.
  • the following odor test was conducted. A panel of 25 people was asked to evaluate the odor of the methyl ether of styrenated phenol against benzyl ethyl benzene, a commercial solvent for the color former. Each member of the panel was allowed to sniff containers containing the solvents. Twenty members of the panel found the methyl ether of styrenated phenol to have a less objectionable odor.
  • Example II To 100 grams of the methyl ether of styrenated phenol, as prepared in Example I, was added 3.0 grams. of Crystal Violet Lactone color former. The mixture was heated to 90°C with stirring to dissolve the color former and then cooled to 50°C. Separately, a solution containing 20 grams gum arabic, 5 grams of a polyoxyalkylene glycol mono-butyl ether emulsifying agent (Tergitol XD) and 180 grams of water was prepared by stirring and heating to 50°C. To this was added the solution containing the color former. The mixture of the two solutions was stirred at 50°C until the solvent containing the color former was emulsified.
  • a polyoxyalkylene glycol mono-butyl ether emulsifying agent Tegitol XD
  • a solution of 20 grams gelatin in 300 grams of water was prepared by slowly adding gelatin to the water at 50°C.
  • the resulting solution was added to the emulsified solvent containing the color former, Crystal Violet Lactone.
  • the resulting mixture was maintained at 50°C with stirring while 335 grams of water was added dropwise in about 30 minutes.
  • the mixture was then cooled to 10°C, 10 grams of 37% by weight of formaldehyde in water added and the pH adjusted to 9.5 by dropwise addition of a 5% by weight solution in water of sodium hydroxide. This mixture was stirred at 10°C for about 30 minutes and then allowed to stand overnight at room temperature.
  • the resulting encapsulated solvent/color former solution was spread on a sheet of uncoated publication paper by means of a No. 8 Meyer spreader. After drying, the coated paper was tested as follows:
  • Example II To 100 grams of the n-butyl ether of styrenated phenol, as prepared in Example II, was dissolved 3.0 grams of Crystal Violet Lactone by stirring and heating to 90°C. The resulting solution was emulsified and encapsulated according to the procedure of Example VII. The resulting encapsulated composition was spread on to a sheet of uncoated publication paper using a No. 8 Meyer spreader. After drying, this coated sheet was tested by placing it, coated side down, against the coated side of acid clay coated paper. When writing on the uncoated face of the sheet containing the encapsulated color former, an image immediately formed on the acid clay coated paper. No objectionable odor was emitted.
  • Example III To 100 grams of the methyl ether of alpha-methyl styrenated phenol as prepared in Example III, was dissolved 3.0 grams of Crystal Violet Lactone by stirring and heating to 90°C. The resulting solution was emulsified and encapsulated according to the procedure of Example VII. The resulting encapsulated composition was spread on a sheet of uncoated publication paper using a. No. 8 Meyer spreader. After drying, this coated sheet was tested by placing it, coated side down, against the coated side of acid clay coated paper. By writing on the uncoated face of the sheet containing the encapsulated color former, an image immediately formed on the acid clay coated paper. No objectionable odor was emitted.
  • Example VII To 100 grams of benzyl anisole as prepared in Example IV, was dissolved 3.0 grams of Crystal Violet Lactone by stirring and heating to 90°C. The resulting solution was emulsified and encapsulated according to the procedure of Example VII. The resulting encapsulated composition was spread on a sheet of uncoated publication paper using a No. 8 Meyer spreader. After drying, this coated sheet was tested by placing it, coated side down, against the coated side of acid clay coated paper. By writing on the uncoated face of the sheet containing the encapsulated color former, an image immediately formed on the acid clay coated paper. No objectionable odor was emitted.
  • the solubility of water in the alkoxy diphenyl alkane solvent prepared according to Example I is about 0.4 gram per 100 ml.
  • a 100 ml sample of the solvent of Example I was placed in a stoppered glass vessel. A quantity of water, 0.35 gram, was then dissolved in the solvent. As a control, another 100 ml sample of the solvent of Example I was placed in another vessel of the same kind. No water was added. A panel of twenty-five individuals was asked to evaluate the odor of the two samples. Each member of the panel was allowed to sniff the two vessels. Twenty-five out of twenty-five members of the panel concluded that the solvent with added water had a milder - odor and the quality of the odor was less objectionable.
  • alkoxy diphenyl alkanes which are useful as solvents for the color former are one or a mixture of the following: 1-benzyl-2,4-dimethoxybenzene; benzyl p-dimethoxybenzene; bis(3,4-dimethoxyphenyl) methane (m.p. 70 - 71°C; 1-benzyl-2,4-dipropoxy benzene; 1-benzyl-2,4-diethoxybenzene; 1-benzyl-2,4-dibutoxybenzene; l-phenylethyl-2,4-dimethoxybenzene; 3,4-dimethoxyphenyl-3-methoxyphenyl methane (m.p.

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EP81100898A 1981-02-09 1981-02-09 Papiers copiants sensibles à la pression Withdrawn EP0057740A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP81100898A EP0057740A1 (fr) 1981-02-09 1981-02-09 Papiers copiants sensibles à la pression

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EP81100898A EP0057740A1 (fr) 1981-02-09 1981-02-09 Papiers copiants sensibles à la pression

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EP0057740A1 true EP0057740A1 (fr) 1982-08-18

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0487347A1 (fr) * 1990-11-21 1992-05-27 Minnesota Mining And Manufacturing Company Papier sans carbone pour l'impression dans des copieurs électrophotographiques
EP0486745A1 (fr) * 1990-11-20 1992-05-27 Monsanto Europe S.A./N.V. Solvants améliorés pour chromogènes utiles dans la fabrication des papiers d'enregistrement sans carbone
US7030198B2 (en) * 2000-12-06 2006-04-18 Quarella S.P.A. Curable compositions comprising an epoxidised unsaturated polyester and mineral fillers

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2242251A1 (fr) * 1973-08-30 1975-03-28 Monsanto Co
DE2342758A1 (de) * 1973-08-24 1975-04-10 Pelikan Werke Wagner Guenther Farbreaktionssysteme
DE2726782A1 (de) * 1976-06-16 1977-12-29 Monsanto Europe Sa Loesungsmittelgemische und sie enthaltende kohlefreie kopierpapiersysteme
FR2373590A1 (fr) * 1976-12-07 1978-07-07 Monsanto Europe Sa Solvants de colorants pour la preparation de papiers copiants sans carbone
US4105743A (en) * 1976-06-15 1978-08-08 Mx-Processer Reinhardt & Co. Ab Selectively extracting copper, zinc, nickel from a mixture of metal hydroxides
FR2445360A1 (fr) * 1978-12-29 1980-07-25 Appleton Paper Inc Composition chromogenique, son procede de preparation et son application a la production d'un materiel de copiage sensible a la pression
GB2039934A (en) * 1978-12-29 1980-08-20 Appleton Paper Inc Record receiving sheet

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2342758A1 (de) * 1973-08-24 1975-04-10 Pelikan Werke Wagner Guenther Farbreaktionssysteme
FR2242251A1 (fr) * 1973-08-30 1975-03-28 Monsanto Co
US3968320A (en) * 1973-08-30 1976-07-06 Monsanto Company Dye solvents for pressure-sensitive record material
US4105743A (en) * 1976-06-15 1978-08-08 Mx-Processer Reinhardt & Co. Ab Selectively extracting copper, zinc, nickel from a mixture of metal hydroxides
DE2726782A1 (de) * 1976-06-16 1977-12-29 Monsanto Europe Sa Loesungsmittelgemische und sie enthaltende kohlefreie kopierpapiersysteme
FR2373590A1 (fr) * 1976-12-07 1978-07-07 Monsanto Europe Sa Solvants de colorants pour la preparation de papiers copiants sans carbone
GB1564931A (en) * 1976-12-07 1980-04-16 Monsanto Europe Sa Dye solvents
FR2445360A1 (fr) * 1978-12-29 1980-07-25 Appleton Paper Inc Composition chromogenique, son procede de preparation et son application a la production d'un materiel de copiage sensible a la pression
GB2039934A (en) * 1978-12-29 1980-08-20 Appleton Paper Inc Record receiving sheet

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0486745A1 (fr) * 1990-11-20 1992-05-27 Monsanto Europe S.A./N.V. Solvants améliorés pour chromogènes utiles dans la fabrication des papiers d'enregistrement sans carbone
EP0487347A1 (fr) * 1990-11-21 1992-05-27 Minnesota Mining And Manufacturing Company Papier sans carbone pour l'impression dans des copieurs électrophotographiques
AU649737B2 (en) * 1990-11-21 1994-06-02 Minnesota Mining And Manufacturing Company Carbonless paper printable in electrophotographic copiers
US7030198B2 (en) * 2000-12-06 2006-04-18 Quarella S.P.A. Curable compositions comprising an epoxidised unsaturated polyester and mineral fillers

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