GB691694A - Improvements in the manufacture of methine cyanine dyes - Google Patents

Improvements in the manufacture of methine cyanine dyes

Info

Publication number
GB691694A
GB691694A GB2328450A GB2328450A GB691694A GB 691694 A GB691694 A GB 691694A GB 2328450 A GB2328450 A GB 2328450A GB 2328450 A GB2328450 A GB 2328450A GB 691694 A GB691694 A GB 691694A
Authority
GB
United Kingdom
Prior art keywords
dimethylpyrrole
bis
monomethinecyanine
perchlorate
prepared
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
GB2328450A
Inventor
Kenneth James Reed
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
Priority to GB2328550A priority Critical patent/GB696646A/en
Priority to GB2328450A priority patent/GB691694A/en
Priority to BE505989D priority patent/BE505989A/xx
Priority to FR1087261D priority patent/FR1087261A/en
Priority to BE505990D priority patent/BE505990A/xx
Priority to FR1053982D priority patent/FR1053982A/en
Publication of GB691694A publication Critical patent/GB691694A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor
    • G03C1/832—Methine or polymethine dyes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
    • H01H9/00—Details of switching devices, not covered by groups H01H1/00 - H01H7/00
    • H01H9/10—Adaptation for built-in fuses
    • H01H9/104—Adaptation for built-in fuses with interlocking mechanism between switch and fuse

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Pyrrole Compounds (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)

Abstract

1 - Cyclohexyl - 2 : 5 - dimethylpyrrole is prepared by refluxing together cyclohexylamine, acetonylacetone, and benzene. 1-Ethyl-2 : 5-dimethylpyrrole, 1 - n - butyl - 2 : 5 - dimethylpyrrole, 1-n-octyl-2 : 5-dimethylpyrrole, 1-n-octadecyl - 2 : 5 - dimethylpyrrole, 1 - phenyl - 2 : 5 - dimethylpyrrole, 1 - o - hydroxyphenyl - 2 : 5 - dimethylpyrrole, 1 - o - carboxyphenyl - 2 : 5 - dimethylpyrrole, 1 - anilino - 2 : 5 - dimethylpyrrole, 1-benzyl-2 : 5-dimethylpyrrole, 1 : 11-ethylene - bis - (2 : 5 - dimethylpyrrole), and 1 - b - hydroxyethyl-2 : 5-dimethylpyrrole are similarly prepared. Octane-2 : 5-dione is prepared by mixing together chloromethyl propyl ketone and sodium ethyl acetoacetate, refluxing, and hydrolysing by refluxing with aqueous sulphuric acid. Specification 529,440 is referred to.ALSO:Monomethine cyanine dyes are prepared by condensing with formic acid a pyrrole compound of the general formula <FORM:0691694/IV (c)/1> wherein R1 is an anilino, alkyl, aralkyl, cycloalkyl, aryl, 1-pyrrylalkyl, or 1-pyrrylaryl group, R2 and R4 are alkyl or aryl groups, and R3 is H or a carbalkoxy group. The formic acid may have a concentration of 50 to 100 per cent by weight. Bis - 3 - (1 - cyclohexyl - 2 : 5 - dimethylpyrrole) - monomethinecyanine perchlorate is prepared by refluxing together 1-cyclohexyl-2 : 5-dimethylpyrrole and formic acid, and adding perchloric acid to the product. Bis-3-(1 - dodecyl - 2 : 5 - dimethylpyrrole) - monomethinecyanine sulphate, bis-3-(1-ethyl-2 : 5-dimethylpyrrole) - monomethinecyanine perchlorate, bis - 3 - (1 - n - butyl - 2 : 5 - dimethylpyrrole) - monomethinecyanine perchlorate, bis-3 - (1 - n - octyl - 2 : 5 - dimethylpyrrole) - monomethinecyanine perchlorate, bis - 3 - (1 - n-octadecyl - 2 : 5 - dimethylpyrrole) - monomethinecyanine formate, bis - 3 - (1 - phenyl-2 : 5 - dimethylpyrrole) - monomethinecyanine perchlorate, bis - 3 - (1 - o - hydroxyphenyl - 2 : 5-dimethylpyrrole) - monomethinecyanine perchlorate, bis - 3 - (1 - o - carboxyphenyl - 2 : 5-dimethylpyrrole) - monomethineperchlorate, bis-3 - (1 - anilino - 2 : 5 - dimethylpyrrole) - monomethinecyanine perchlorate, bis - 3 - (1 - benzyl-2 : 5 - dimethylpyrrole) - monomethinecyanine perchlorate, the dyes from 1 : 11-ethylene-bis-(2 : 5-dimethylpyrrole and formic acid and from 1 : 11 - [diphenylene - (4 : 41)] - bis - (2 : 5 dimethylpyrrole) and formic acid, and bis-3-(1 - b - hydroxyethyl - 2 : 5 - dimethylpyrrole)-monomethinecyanine perchlorate are similarly prepared. Specification 529,440, [Group XX], is referred to.
GB2328450A 1950-09-22 1950-09-22 Improvements in the manufacture of methine cyanine dyes Expired GB691694A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB2328550A GB696646A (en) 1950-09-22 1950-09-22 Improvements in methine cyanine dyes
GB2328450A GB691694A (en) 1950-09-22 1950-09-22 Improvements in the manufacture of methine cyanine dyes
BE505989D BE505989A (en) 1950-09-22 1951-09-21
FR1087261D FR1087261A (en) 1950-09-22 1951-09-21 New dipyrrolmethine dyes, process for their preparation and applications
BE505990D BE505990A (en) 1950-09-22 1951-09-21
FR1053982D FR1053982A (en) 1950-09-22 1951-09-21 Process for the preparation of methine dyes, new dyes and their applications

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2328450A GB691694A (en) 1950-09-22 1950-09-22 Improvements in the manufacture of methine cyanine dyes

Publications (1)

Publication Number Publication Date
GB691694A true GB691694A (en) 1953-05-20

Family

ID=46384628

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2328450A Expired GB691694A (en) 1950-09-22 1950-09-22 Improvements in the manufacture of methine cyanine dyes
GB2328550A Expired GB696646A (en) 1950-09-22 1950-09-22 Improvements in methine cyanine dyes

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2328550A Expired GB696646A (en) 1950-09-22 1950-09-22 Improvements in methine cyanine dyes

Country Status (3)

Country Link
BE (2) BE505990A (en)
FR (2) FR1053982A (en)
GB (2) GB691694A (en)

Also Published As

Publication number Publication date
BE505990A (en) 1953-01-30
FR1087261A (en) 1955-02-22
BE505989A (en) 1953-01-30
FR1053982A (en) 1954-02-08
GB696646A (en) 1953-09-02

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