GB927895A - Improvements in heat sensitive copying materials - Google Patents

Improvements in heat sensitive copying materials

Info

Publication number
GB927895A
GB927895A GB16681/59A GB1668159A GB927895A GB 927895 A GB927895 A GB 927895A GB 16681/59 A GB16681/59 A GB 16681/59A GB 1668159 A GB1668159 A GB 1668159A GB 927895 A GB927895 A GB 927895A
Authority
GB
United Kingdom
Prior art keywords
butylhydroquinone
tert
cooling
followed
filtrate
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
Application number
GB16681/59A
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.)
Kodak Ltd
Original Assignee
Kodak 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
Application filed by Kodak Ltd filed Critical Kodak Ltd
Publication of GB927895A publication Critical patent/GB927895A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/02—Quinones with monocyclic quinoid structure
    • 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
    • B41M5/323—Organic colour formers, e.g. leuco dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
    • C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
    • C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

2-n-Hexadecyl-5-methylquinone is prepared by adding the corresponding hydroquinone to an oxidizing mixture of glacial acetic acid, dilute sulphuric acid and sodium chlorate together with vanadium pentoxide as catalyst, the temperature being held at 80 DEG C. and the hydroquinone being added in portions with rapid stirring and stirred for 1 hour without applying heat, followed by cooling, drying and recrystallization. 2-n-Octadecylquinone is prepared from the corresponding hydroquinone by dissolving it in acetone containing 5% by volume of water held cooled to 10 DEG C. and then adding dropwise in succession concentrated sulphuric acid and sodium dichromate, followed by stirring and crystallization. 2-Allyl-5-tert.-butylhydroquinone is prepared by reflux heating under an inert atmosphere of a mixture of tert.-butylhydroquinone, allyl chloride methanol, water and zinc dust, adding dropwise caustic soda solution and continuing refluxing for 3 hours, followed by cooling and extraction with benzene, extraction with aqueous sodium hydroxide to remove unreacted tert.-butylhydroquinone, distillation of the benzene solution, refluxing with kerosene, extraction with dilute acetic acid, and finally recrystallization successively from a hexane-benzene mixture and then aqueous acetic acid. 2-Chloro-5-tert.-butylhydroquinone is produced by adding with stirring tert.-butylhydroquinone to chloroform, heating to 48 DEG C. and very slowly adding sulphuryl chloride at this temperature, followed by the addition of zinc dust and cooling to 10 DEG C.; filtering off the solids, extracting the filtrate at 60 DEG C. with aqueous sodium hydroxide, cooling the extract to 30 DEG C. and treating with sodium hydrosulphite, acidifying with concentrated hydrochloric acid, filtering and washing the filtrate with cold water and finally drying. 1:2:4:5-Tetrahydroxybenzene is formed by hydrogenation of 2:5-dihydroxy-1:4-benzoquinone in water in the presence of a palladium-on-alumina catalyst in an autoclave at an initial pressure of 800 lbs./sq. in. and a temperature of 27 DEG -47 DEG C., heating the contents to 72 DEG C. when the pressure has fallen by 160 lbs./sq. in. and discharging the contents at 70 DEG -80 DEG C. into an aqueous solution of sodium hydrosulphite containing decolourising carbon, filtering through diatomaceous earth and cooling the filtrate to 10 DEG C. to effect crystallisation, washing the crystals and finally vacuum drying. Specifications 752,146 and 752,147 are referred to.
GB16681/59A 1958-05-19 1959-05-15 Improvements in heat sensitive copying materials Expired GB927895A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US73624858A 1958-05-19 1958-05-19

Publications (1)

Publication Number Publication Date
GB927895A true GB927895A (en) 1963-06-06

Family

ID=24959133

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16681/59A Expired GB927895A (en) 1958-05-19 1959-05-15 Improvements in heat sensitive copying materials

Country Status (4)

Country Link
US (1) US2899334A (en)
DE (1) DE1129510B (en)
FR (1) FR1231262A (en)
GB (1) GB927895A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0262900A2 (en) * 1986-09-29 1988-04-06 E.I. Du Pont De Nemours And Company Anisotropic melt polyesters with improved glass transition temperature
CN112210290A (en) * 2020-10-12 2021-01-12 上海北昂医药科技股份有限公司 Diaphragm for rotary distribution valve

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1109712B (en) * 1958-08-09 1961-06-29 Kalle Ag Copy layers for producing images by heat
US2995465A (en) * 1959-08-07 1961-08-08 Minnesota Mining & Mfg Copy-sheet
US2995466A (en) * 1959-08-07 1961-08-08 Minnesota Mining & Mfg Heat-sensitive copy-sheet
BE593980A (en) * 1959-08-14
US3076721A (en) * 1959-10-19 1963-02-05 Minnesota Mining & Mfg Heat-sensitive copy-paper and method of making
US3090697A (en) * 1961-02-13 1963-05-21 Nashua Corp Heat sensitive marking papers and methods for making same
BE626634A (en) * 1962-01-05 1900-01-01
NL287454A (en) * 1962-01-18
US3166433A (en) * 1962-08-01 1965-01-19 Nashua Corp Heat sensitive copy and recording sheet
US3293061A (en) * 1963-11-21 1966-12-20 Man Res Lab Inc Primary amine modified secondary or tertiary amine-polyketo reaction product in a heat developable copy sheet
US3515568A (en) * 1967-07-03 1970-06-02 Eastman Kodak Co Processing of erasing from a thermographic element
US4766256A (en) * 1986-09-29 1988-08-23 E. I. Du Pont De Nemours And Company Anisotropic melt polyesters with improved glass transition temperature
US7022441B2 (en) * 2004-02-25 2006-04-04 Eastman Kodak Company Silver-free black-and-white thermographic materials containing a benzoquinone and methods of imaging

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0262900A2 (en) * 1986-09-29 1988-04-06 E.I. Du Pont De Nemours And Company Anisotropic melt polyesters with improved glass transition temperature
EP0262900A3 (en) * 1986-09-29 1989-05-31 E.I. Du Pont De Nemours And Company Anisotropic melt polyesters with improved glass transition temperature
CN112210290A (en) * 2020-10-12 2021-01-12 上海北昂医药科技股份有限公司 Diaphragm for rotary distribution valve
CN112210290B (en) * 2020-10-12 2021-08-06 上海北昂医药科技股份有限公司 Diaphragm for rotary distribution valve

Also Published As

Publication number Publication date
US2899334A (en) 1959-08-11
FR1231262A (en) 1960-09-28
DE1129510B (en) 1962-05-17

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