US3149993A - Heat developable paper - Google Patents

Heat developable paper Download PDF

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Publication number
US3149993A
US3149993A US255085A US25508563A US3149993A US 3149993 A US3149993 A US 3149993A US 255085 A US255085 A US 255085A US 25508563 A US25508563 A US 25508563A US 3149993 A US3149993 A US 3149993A
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United States
Prior art keywords
salt
reagent
organic
colored
compound
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Expired - Lifetime
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US255085A
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English (en)
Inventor
Michael F Baumann
William R Lawton
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Nashua Corp
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Nashua Corp
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Publication date
Priority to BE627029D priority Critical patent/BE627029A/xx
Priority to NL287454D priority patent/NL287454A/xx
Priority to GB48987/62A priority patent/GB1000088A/en
Priority to DEN22558A priority patent/DE1213436B/de
Priority to FR921207A priority patent/FR1472017A/fr
Priority to CH37763A priority patent/CH408071A/fr
Application filed by Nashua Corp filed Critical Nashua Corp
Priority to US255085A priority patent/US3149993A/en
Application granted granted Critical
Publication of US3149993A publication Critical patent/US3149993A/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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/32—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers one component being a heavy metal compound, e.g. lead or iron
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/913—Material designed to be responsive to temperature, light, moisture
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/165—Thermal imaging composition

Definitions

  • This invention relates to heat marking processes and provides a novel heat sensitive sheet useful for copying and recording uses, and characterized by the ability to form a mark of contrasting color when heated to an activation temperature in the range of 50-150" C.
  • Sheets of this type are commonly employed in thermographic copying processes, in which a sheet is placed next to a graphic original and is exposed with the original to infrared radiation which causes selective heating of the dark areas of the original sufiicient to form a copy thereof on the copy sheet. A detailed description of this process is set forth in US. Patent No. 2,740,896.
  • the sheets of this invention may also be used in recording devices in which marking is accomplished by means of a heated stylus.
  • materials which are reactive to form a colored compound are incorporated in the sheet in intimate association.
  • These materials include an ionizable polyvalent metal salt, and an electron donor organic reagent which forms a distinctly colored covalent coordination metallo-organic complex with the metal ions of the salt.
  • precursors of the colored compound include an ionizable polyvalent metal salt, and an electron donor organic reagent which forms a distinctly colored covalent coordination metallo-organic complex with the metal ions of the salt.
  • the salts of metals which may be identified by spot test techniques and reagents useful for spot tests, as well as salts and organic reagents which combine in other similar known color forming reactions with the formation of a colored covalent coordination metallo-organic complex.
  • both of the precursors are present as physically distinct but intimately associated components.
  • a heat responsive reaction between these components is brought about by providing a solid stable co-crystal adduct in which the carrier compound is either a bisphenol or an hydroxyphenyl substituted chroman-and the included compound is a liquid organic ammonia derivative, e.g., organic amines or amides, hydrazine derivatives and guanadine derivatives, to name but a few.
  • Solid adducts of this type are well known; many are described in U.S. Patent No. 2,829,175.
  • the cocrystal adduct dissociates when heated and thereupon releases its liquid organic ammonia derivative which then serves as the vehicle for the color forming reaction between the precursors of the colored compound.
  • color formation is due to the ability of the organic ammonia derivative to cause the metallic salt to ionize and thereby bring the metallic salt and organic reagent into reactive association.
  • the ammonia derivatives do not appear to enter into any kind of chemical reaction with either of the other color-forming reagents, but on the contrary serve what is essentially a physical function.
  • the color body precursors should be lightly colored, solid, non-hydroscopic, and otherwise stable, at normal conditions of temperature and humidity, that is, those conditions one might expect to encounter in actual conditions of storage, shipment, and use.
  • the co-crystal adduct should be similarly stable, and lightly colored, and should in addition he dissociable to yield the ammonia derivative at the desired activation temperature in the range of 50150 C.
  • the particular bisphenol or hydroxyphenyl substituted chromans and ammonia derivatives are accordingly to be selected with reference to these criteria on the basis of known, or readily ascertainable, characteristics of materials of this type.
  • the metal salt, the organic reagent and the co-crystal adduct are dispersed separately or together in a binder solu tion and applied as one or more coatings to a paper or other base by conventional techniques.
  • the relative proportions of the color compound precursors should be such as to provide mutual reaction, with a total concentration sufficient to produce a distinct contrasting color mark when the sheet is heated.
  • the amount of co-crystal adduct should be sufficient to provide enough of the ammonia derivative as a reaction vehicle to bring about a color forming reaction between the color compound precursors. These quantities may be determined by routine experimentation. While the amount of organic ammonia derivative employed may vary considerably depending upon the particular color compound presursors selected it has been found that most effective results are obtained when the ammonia derivative is provided in an amount equal to at least about 5% of the weight of the precursors.
  • Example I A co-crystal adduct is first formed by combining:
  • Tetrachloro bisphenol A 183 Ethanol amine (EA) 61 Toluene 364 by dissolving the TCBA in the toluene at 150 F., adding the ethanol amine and stirring for 30 minutes. The mixture is chilled to about 30 F. and held at that temperature for about 14 hours (overnight) during which time a precipitate forms. This is filtered off, washed thoroughly with n-hexane at room temperature F.) and dried. The solid crystal product is the co-crystal adduct of tetrachloro bisphenol A and ethanol amine (TCBA/EA) having a melting point of 96104 C.
  • a dispersion is prepared of:
  • the mixture is charged in a ball mill and milled overnight at 40 F.
  • a second dispersion is prepared consisting of Parts by Weight Dithiooxamide (rubeanic acid) H 2.5 Polyvinyl -butyral (Butvar 13-76) 2.5 Trichloroethylene 95 This mixture is similarly charged in a ball mill and milled over night at 40 F.
  • Nickel oxalate 10 Polyvinyl butyral (Butvar B-87) 2.5 Trichloroethylene 87 .5
  • This mixture is dispersed in the same manner as the dispersions prepared above.
  • a mixture of the three dispersions is prepared in the proportions of 3 parts of dispersion A, parts of dispersion B, and 2 parts of dispersion C. After thorough mixing, this is coated in the conventional manner upon a 25-pound per ream (500 sheets, 24 x 36") glassine base to a coating weight of 4 pounds per ream.
  • the coated paper is dried in air and may be used in a recording machine having a heated stylus, e.q., a Viso-cardiette electrocardiograph, a trace velocity of 100-300 inches per second.
  • the sheets may also be used in thermographic processes, e.g,, in a Minnesota Mining and Manufacturing Company Thermofax copier, Model 17H, at settings of from 1 to 5.
  • Example II A co-crystal adduet is formed according to the procedure of Example I from a combination of:
  • a dispersion is prepared of:
  • EHEC Ethyl hydroxy ethyl cellulose
  • a second dispersion is prepared consisting of:
  • n-Hexane 86 Ethyl alcohol 2 Parts by weight n-Hexane 86 Ethyl alcohol 2 and milling the mixture in a ball mill at F. overnight.
  • a heat marking sheet is prepared by first coating a 5% solution of cadmium nitrate in a 40-60 by Weight methanol-Water mixture on a 25-pound per ream glassine sheet to a Wet thickness of about 1 mil. After the sheet has been dried, a 6% solution of gelatin in a 4060 by Weight methanol-Water mixture is applied to a coating thickness of 2 mils Wet. After the gelatin coating has dried, a mixture consisting of 2 parts of dispersion A and 1 part of dispersion B is applied to a dry weight of 5 pounds per ream. Upon drying a heat marking sheet suitable for copying and recording purposes is provided.
  • Example III A co-crystal adduct is formed according to the procedure of Example I from a combination of:
  • a dispersion is prepared of:
  • the mixture is charged in a ball mill and milled Overnight at 40 F.
  • a second dispersion is prepared consisting of:
  • a heat marking sheet is prepared by first coating on a 25-pound per ream glassine sheet, to a coating weight of 5 pounds per ream, a mixture of equal parts of dispersion B and dispersion C. This coating When dried is topcoated with a 3 pound per ream coating from dispersion A. The resulting sheet provides an eifective heat marking copy or recording medium.
  • polyvalent metal salts may also be utilized in the preparation of sheets according to the present invention, including nickel formate, cobalt oxalate, nickel sulfate, aluminum chloride, copper oxalate, lead chloride, zinc sulfate, manganese chloride, nickel tartrate, ferrous oxalate, barium chloride, and chelates of nickel chloride with such compounds as 1,3-propylenediamine, tetramethylenediamine, and diamine hexane.
  • organic reagents that form colored covalent coordination metallo-organie complexes with polyvalent metal ions and that are suitable for use in compositions of this invention are included dithiooxalic acid and its potassium salt, biuret, 8-hydroxyquinoline, benzoinoxime, 2,2'-dipyridyl, anthranilic acid, pyrogallol, alizarin, tannin, carminic acid, morin, 2,3-butane dioneoxime thiocarbazide.
  • the hydroxyphenyl substituted chromans have been found to be especially useful carrier compounds.
  • Their co-crystal adducts with organic ammonia derivatives are generally water-insensitive, have excellent storage stability, and usually possess dissociation temperatures in a range which is well suited to the thermographic process. Examples in which these compounds are the carriers follow.
  • Example IV 7,4-diethyl-2'-hydroxy-2,4,4 trimethyl flaven was prepared according to the procedure described by Baker, Mc- Omie, and Wild, J. Chem. Soc., 1957, 3060-4.
  • a mixture of m-cresol (400 g.) and cyclohexanone (240 g.) was saturated with dry HCl for one hour at 0 C., kept for three days at room temperature and one day at 40-50 C. and stirred into 4 liters of an aqueous 2 normal sodium hydroxide solution.
  • the product was extracted with a mixture of 1000 cc. diethylether and 400 cc. hexane.
  • Example VI 2-hydroxy-2,4,4,6,7,4',5-heptamethylflavan was prepared by the procedure described by Baker, McOmie, and Wild, J. Chem. Soc., 1957, 3060-4.
  • the diethanolamine complex was prepared by treating 30 g. of the flavan in a hexane-toluol solution with 10 g. diethanolamine. A solid product was obtained after chilling overnight at -20 C. The yield of the diethanolamine/flavan complex was 32.5 g. and the melting point was 153-7" C. with considerable softening at much lower temperature.
  • Example VII 2'-hydroxy-2,4,4,6,5-pentamethylfiavan was prepared by the procedure described by Baker, Curtis, and McOmie in J. Chem. Soc., 1952, 1774-85.
  • Example VIII 2-hydroxy-2,4,4,7,4'-pentamethylflavan was prepared by the procedure described by Baker and Besley in J. Chem. Soc., 1951, 1103-6.
  • organic ammonia derivatives representative of those that might be employed in the foregoing illustrative and suggested compositions include tetramethyl guanadine, ethyl ethanol amine, phenyl ethanol amine, dibutylamine, hydrazine N-Z-hydroxyethyl 1 methyl dodecylamine, formamide, piperidine, triethanolamine, cyclohexylamine, Numerous other bisphenols may be used in the formation of the co-crystal adducts of the organic ammonia derivatives, including tetrabromobisphenol A, bithionol, bisphenol A as well as others listed in the above-identified Patent No. 2,829,175.
  • the hydroxyphenyl substituted chroman/amine complexes may be incorporated into the'color-forming, heatreactive coatings in the same manner as has been described in connection with the bisphenol/ amine adducts, i.e., all three dispersions in organic liquids may be combined into a single coating composition.
  • binders which can be water-soluble polymers such as glue, starch, polyvinyl alcohol, Water-soluble gums, carboxymethyl cellulose, hydroxyethyl cellulose and like substances.
  • binders are less compatible with the chroman/ amine adducts than are the organic solvent-soluble types and therefore have less tendency to interact with the adduct. This fact contributes to the storage stability of the chroman/ amine systems.
  • a ball-mill grind is made containing:
  • Test coatings were coated with a No. 12 Mayer rod on 45-lb. stock to give a weight-coat of 3-5 lbs. per ream of 24" x 36" x 500 sheets.
  • the dried amine complex coatings were overcoated with the various color-forming systems to give a top coat dry Weight of 0.5-2 lbs. per ream.
  • Example IX A. 20 parts of 7,4'-diethyl-2'-hydroxy-2,4,4-trimethyl flavan (Example IV) was 'grounded in a ball-mill for 24 hours in a 2% water solution of polyvinyl alcohol.
  • SuspensionA was coated on 25 lbs. glassine base (24 x 36" x 500 pages) to a coating weight of 4 lbs. per
  • Suspension C was overcoated on the dried coated sheet (B) to a coating weight of 2 lbs. per ream.
  • the coated sheet Will give clear, colored indicia under a heated stylus or in a thermographic copy machine.
  • Co-crystal adducts suitable for a particular application should be selected with reference to the dissociation temperature, which may be determined by mixing the adduct with a mixture of nicket oxalate and rubeanic acid in the dry state and heating slowly until a color is formed.
  • the co-crystal adduct should also be selected with reference to its stability, color, and hydroscopic properties, so as to impart the desired properties in the paper.
  • the sheets described in the foregoing examples have activation temperatures of a range of 50-150 C., as determined by placing the sheet on a heated surface for 1 second, and measuring the lowest temperature at which a visibly distinct color change occurs in the heated area.
  • the accompanying drawing illustrates schematically a heat sensitive sheet corresponding to this invention.
  • the sheet is represented as being in cross section.
  • ingredients may also be included in the coating such as anti-tack agents, anti-fingerprinting agents, anti-static agents, fillers, and coloring compounds, and bases other than glassine, e.g., regenerated cellulose, cellulose esters, other forms of paper and plastic materials may also be used if desired.
  • a heat sensitive sheet adapted for dry heat marking processes, stable and lightly colored under normal conditions and responsive to heating to an activation temperature in the range of 50 C.-150 C. by changing visibly and irreversibly to a contrasting color through the formation of a colored compound
  • said sheet including a solid stable ionizable polyvalent metal salt and a solid stable organic reagent reactive with the metal ions of said salt in the presence of a liquid ammonia derivative to form a colored metallo-organic compound by covalent coordinate bonding between said metal ions and said reagent, said salt and reagent being precursors of said colored compound present in said sheet in physically distinct potentially reactive association, and a solid, stable crystalline cocrystal adduct of a liquid organic ammonia derivative and a hydroxyphenol carrier compound selected from the class consisting of bisphenols and hydroxyphenyl substituted chromans, said adduct having a dissociation temperature of between 50 C. and 150 C. at which temperature said '1'0 liquid ammonia derivative is released
  • a heat sensitive sheet adapted for dry heat marking processes, stable and lightly colored under normal conditions responsive to heating to an activation temperature in the range of 50 C. C. by changing visibly and irreversibly to a contrasting color through the formation of a colored compound, said sheet including solid stable precursors of said compound in physically distinct intimate potentially reactive association, one of said precursors being an ionizable polyvalent metal salt and the other being an organic reagent reactive with the metal ions from said salt in the presence of a liquid ammonia derivative to form a colored metallo-organic compound by covalent coordinate bonding between said metal ions and said reagents, and a solid stable crystalline co-crystal adduct of a liquid organic ammonia derivative and a hydroxyphenol carrier compound selected from the class consisting of bisphenols and hydroxyphenyl substituted chromans, said adduct dissociating at a temperature of from 50 C.150 C. to yield said ammonia derivative and thereby provide a vehicle for the color-forming reaction between said salt and said sheet
  • a heat sensitive sheet adapted for dry heat marking processes, stable and lightly colored under normal conditions and responsive to heating to an activation temperature in the range of 50 C.150 C. by changing visibly and irreversibly to a contrasting color through the formation of a colored compound, said sheet comprising a web of flexible sheet material, and a layer coated thereon and adherent thereto and comprising an intimate and uni form potentially reactive mixture of a solid stable ionizable polyvalent metal salt, a solid stable organic reagent reactive with the metal ions of said salt in the presence of a liquid ammonia derivative to form a colored metalloorganic compound by covalent coordinate bonding between said metal ions and said reagent, and a solid, stable crystalline co-crystal adduct of a liquid organic ammonia derivative and a hydroxyphenol carrier compound selected from the class consisting of bisphenols and hydroxyphenyl substituted chromans, said adduct: having a dissociation temperature of between 50 C. and 150 C. at which temperature said liquid am
  • a heat sensitive sheet adapted for dry heat marking processes, stable and lightly colored under normal conditions and responsive to heating to an activation temperature in the range of 50 C.-150 C. by changing visibly and irreversibly to a contrasting color through the formation of a colored compound, said sheet comprising a web of flexible sheet material, and a layer coated thereon and adherent thereto and comprising, in physically distinct potentially reactive association, a solid stable ionizable polyvalent metal salt, a solid stable organic reagent reactive with the metal ions of said salt in the presence of a liquid ammonia derivative to form a colored metallo-organic compound by covalent coordinate bonding between said metal ions and said reagent, said salt and said reagent being precursors of said colored compound, and a solid stable crystalline co-crystal adduct of a liquid organic ammonia derivative and a hydroxyphenol carrier compound selected from the class consisting of bisphenols and hydroxyphenyl substituted chromans, said adduct having a dissociation temperature of between

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Color Printing (AREA)
US255085A 1962-01-18 1963-01-30 Heat developable paper Expired - Lifetime US3149993A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
BE627029D BE627029A (de) 1962-01-18
NL287454D NL287454A (de) 1962-01-18
GB48987/62A GB1000088A (en) 1962-01-18 1962-12-31 Heat-sensitive sheets
DEN22558A DE1213436B (de) 1962-01-18 1962-12-31 Waermeempfindliches Blattmaterial
FR921207A FR1472017A (fr) 1962-01-18 1963-01-11 Papier développable par la chaleur
CH37763A CH408071A (fr) 1962-01-18 1963-01-11 Papier développable par la chaleur
US255085A US3149993A (en) 1962-01-18 1963-01-30 Heat developable paper

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16718062A 1962-01-18 1962-01-18
US255085A US3149993A (en) 1962-01-18 1963-01-30 Heat developable paper

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US3149993A true US3149993A (en) 1964-09-22

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US255085A Expired - Lifetime US3149993A (en) 1962-01-18 1963-01-30 Heat developable paper

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US (1) US3149993A (de)
BE (1) BE627029A (de)
CH (1) CH408071A (de)
DE (1) DE1213436B (de)
GB (1) GB1000088A (de)
NL (1) NL287454A (de)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3328191A (en) * 1964-03-02 1967-06-27 Hirsch Arthur Heat-sensitive copying sheet
US3819382A (en) * 1970-06-26 1974-06-25 Agfa Gevaert Ag Light-sensitive material having developers embedded therein
US3850649A (en) * 1971-08-05 1974-11-26 Minnesota Mining & Mfg Latent image printing
US3859111A (en) * 1970-11-20 1975-01-07 Gen Co Ltd Heat-sensitive recording sheet
US5622778A (en) * 1991-07-25 1997-04-22 Kabushiki Kaisha Toyota Chuo Kenkyusho Synthetic resin composition and interior material coated with the same
US20060138022A1 (en) * 2004-12-23 2006-06-29 Chevron U.S.A. Inc. Production of low sulfur, moderately aromatic distillate fuels by hydrocracking of combined Fischer-Tropsch and petroleum streams
US20060138024A1 (en) * 2004-12-23 2006-06-29 Chevron U.S.A. Inc. Production of low sulfur, moderately aromatic distillate fuels by hydrocracking of combined fischer-tropsch and petroleum streams

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2663656A (en) * 1952-05-15 1953-12-22 Minnesota Mining & Mfg Heat-sensitive copying paper
US2899334A (en) * 1958-05-19 1959-08-11 Heat-sensitive layer
US2967785A (en) * 1959-08-14 1961-01-10 Eastman Kodak Co Thermographic copying material
US2995466A (en) * 1959-08-07 1961-08-08 Minnesota Mining & Mfg Heat-sensitive copy-sheet
US3024362A (en) * 1958-08-09 1962-03-06 Kalle Ag Heat sensitive reproduction material and mbthod of using same
US3076707A (en) * 1959-04-22 1963-02-05 Nashua Corp Heat developable copy sheet and compositions useful therefor

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2663656A (en) * 1952-05-15 1953-12-22 Minnesota Mining & Mfg Heat-sensitive copying paper
US2899334A (en) * 1958-05-19 1959-08-11 Heat-sensitive layer
US3024362A (en) * 1958-08-09 1962-03-06 Kalle Ag Heat sensitive reproduction material and mbthod of using same
US3076707A (en) * 1959-04-22 1963-02-05 Nashua Corp Heat developable copy sheet and compositions useful therefor
US2995466A (en) * 1959-08-07 1961-08-08 Minnesota Mining & Mfg Heat-sensitive copy-sheet
US2967785A (en) * 1959-08-14 1961-01-10 Eastman Kodak Co Thermographic copying material

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3328191A (en) * 1964-03-02 1967-06-27 Hirsch Arthur Heat-sensitive copying sheet
US3819382A (en) * 1970-06-26 1974-06-25 Agfa Gevaert Ag Light-sensitive material having developers embedded therein
US3859111A (en) * 1970-11-20 1975-01-07 Gen Co Ltd Heat-sensitive recording sheet
US3850649A (en) * 1971-08-05 1974-11-26 Minnesota Mining & Mfg Latent image printing
US5622778A (en) * 1991-07-25 1997-04-22 Kabushiki Kaisha Toyota Chuo Kenkyusho Synthetic resin composition and interior material coated with the same
US20060138022A1 (en) * 2004-12-23 2006-06-29 Chevron U.S.A. Inc. Production of low sulfur, moderately aromatic distillate fuels by hydrocracking of combined Fischer-Tropsch and petroleum streams
US20060138024A1 (en) * 2004-12-23 2006-06-29 Chevron U.S.A. Inc. Production of low sulfur, moderately aromatic distillate fuels by hydrocracking of combined fischer-tropsch and petroleum streams
US7374657B2 (en) 2004-12-23 2008-05-20 Chevron Usa Inc. Production of low sulfur, moderately aromatic distillate fuels by hydrocracking of combined Fischer-Tropsch and petroleum streams
US7951287B2 (en) 2004-12-23 2011-05-31 Chevron U.S.A. Inc. Production of low sulfur, moderately aromatic distillate fuels by hydrocracking of combined Fischer-Tropsch and petroleum streams

Also Published As

Publication number Publication date
NL287454A (de)
GB1000088A (en) 1965-08-04
BE627029A (de)
CH408071A (fr) 1966-02-28
DE1213436B (de) 1966-03-31

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