GB1111903A - Cyanine dyes - Google Patents

Cyanine dyes

Info

Publication number
GB1111903A
GB1111903A GB2376665A GB2376665A GB1111903A GB 1111903 A GB1111903 A GB 1111903A GB 2376665 A GB2376665 A GB 2376665A GB 2376665 A GB2376665 A GB 2376665A GB 1111903 A GB1111903 A GB 1111903A
Authority
GB
United Kingdom
Prior art keywords
methyl
alkyl
trifluoromethyl
group
ethyl
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
GB2376665A
Inventor
Konrad Jerzy Bannert
Douglas James Fry
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.)
Ilford Imaging UK Ltd
Original Assignee
Ilford 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 Ilford Ltd filed Critical Ilford Ltd
Priority to GB2376665A priority Critical patent/GB1111903A/en
Priority to GB2339366A priority patent/GB1111904A/en
Priority to BE682090D priority patent/BE682090A/xx
Priority to BE682089D priority patent/BE682089A/xx
Priority to FR64113A priority patent/FR1481888A/en
Priority to DE19661569797 priority patent/DE1569797A1/en
Priority to BE682584D priority patent/BE682584A/xx
Publication of GB1111903A publication Critical patent/GB1111903A/en
Expired legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/02—Monocyclic aromatic halogenated hydrocarbons
    • C07C25/13—Monocyclic aromatic halogenated hydrocarbons containing fluorine
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
    • 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
    • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Indole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention relates to cyanine dyes of the formula <FORM:1111903/C4-C5/1> wherein R is halogen, alkyl 1-6C or amino, R and R3 are alkyl 1-6C, R2 and R4 are alkyl, hydroxyalkyl, aralkyl, carboxy - substituted aralkyl, carboxy - substituted alkyl, -(CH2)n-SO3H, where n is 1 to 6, -(CH2)nSO2NHCOR8, where n is 1 to 6 and R8 is an alkyl group, or -(CH2)nSO2.NHR9, where n is 1 to 6 and R9 is an alkyl or aralkyl group, R5 is H, halogen, alkyl or amino, R6 is H, halogen, trifluoromethyl, cyano, or alkoxy carbonyl except that when R1 and R5 each represent Cl and R6 is -CF3 R2 and R4 are not both the same alkyl group, and X is an anion, and when R2 and R4 are each a sulphoalkyl group, the corresponding anhydro hydroxide compounds. The dyes are obtained by the usual condensation methods.ALSO:1 - Ethyl - 2 - methyl - 5 - trifluoromethyl - 6 - chlorobenzimidazole is obtained by diazotizing 1 - ethyl - 2 - methyl - 5 - trifluoromethyl - 6 - aminobenzimidazole with NaNO2/HCl and treating the product with cuprous chloride. The 1 - ethyl - 2 - methyl - 5 - trifluoromethyl - 6 - aminobenzimidazole is obtained by nitrating the corresponding benzimidazole and reducing the 1 - ethyl - 2 - methyl - 5 - trifluoromethyl - 6 - nitrobenzimidazole produced. 1 - Ethyl - 2,6 - dimethyl - 5 - trifluoromethyl benzimidazole is prepared by reacting p-cresol with carbon tetrachloride/aluminium chloride to give 4-methyl - 4 - trichloromethyl - 2,5 - cyclohexadienone, reacting the latter with phosphorus pentachloride to give 2-methyl-4-chlorobenzotrichloride, conversion of the latter to 2-methyl-4-chlorobenzo trifluoride with antimony trifluoride, conversion of the trifluoride to its 5-nitro compound with nitric acid/sulphuric acid, conversion of the 4-chloro group to a 4-ethylamino group with ethylamine, reduction of the nitro group with Raney nickel/H2 and cyclization of the 5-amino 4-ethylamino 2-methyl benzotrifluoride produced in the presence of acetyl chloride.
GB2376665A 1965-06-03 1965-06-03 Cyanine dyes Expired GB1111903A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB2376665A GB1111903A (en) 1965-06-03 1965-06-03 Cyanine dyes
GB2339366A GB1111904A (en) 1965-06-03 1965-10-19 Trifluoromethyl-substituted benzimidazoles
BE682090D BE682090A (en) 1965-06-03 1966-06-03
BE682089D BE682089A (en) 1965-06-03 1966-06-03
FR64113A FR1481888A (en) 1965-06-03 1966-06-03 New cyanines and their preparation
DE19661569797 DE1569797A1 (en) 1965-06-03 1966-06-03 Cyanine dyes and processes for their preparation
BE682584D BE682584A (en) 1965-06-03 1966-06-15

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2376665A GB1111903A (en) 1965-06-03 1965-06-03 Cyanine dyes
GB4420165 1965-10-19

Publications (1)

Publication Number Publication Date
GB1111903A true GB1111903A (en) 1968-05-01

Family

ID=26256702

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2376665A Expired GB1111903A (en) 1965-06-03 1965-06-03 Cyanine dyes
GB2339366A Expired GB1111904A (en) 1965-06-03 1965-10-19 Trifluoromethyl-substituted benzimidazoles

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2339366A Expired GB1111904A (en) 1965-06-03 1965-10-19 Trifluoromethyl-substituted benzimidazoles

Country Status (2)

Country Link
BE (2) BE682090A (en)
GB (2) GB1111903A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104725207A (en) * 2014-01-11 2015-06-24 天长市天佳化工科技有限公司 Method for preparing 4-methyl-4-trichloromethyl-2, 5-cyclohexadiene-1-ketone

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19954014A1 (en) * 1999-11-10 2001-05-17 Bayer Ag Process for the preparation of trifluoromethylanilines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104725207A (en) * 2014-01-11 2015-06-24 天长市天佳化工科技有限公司 Method for preparing 4-methyl-4-trichloromethyl-2, 5-cyclohexadiene-1-ketone
CN104725207B (en) * 2014-01-11 2016-08-17 天长市天佳化工科技有限公司 A kind of preparation method of 4-methyl-4-trichloromethyl-2,5-cyclohexadiene-1-ketone

Also Published As

Publication number Publication date
BE682584A (en) 1966-11-14
BE682090A (en) 1966-11-14
GB1111904A (en) 1968-05-01

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