GB618889A - Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyes - Google Patents

Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyes

Info

Publication number
GB618889A
GB618889A GB2191546A GB2191546A GB618889A GB 618889 A GB618889 A GB 618889A GB 2191546 A GB2191546 A GB 2191546A GB 2191546 A GB2191546 A GB 2191546A GB 618889 A GB618889 A GB 618889A
Authority
GB
United Kingdom
Prior art keywords
iodide
prepared
dyes
product
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
GB2191546A
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 GB2191546A priority Critical patent/GB618889A/en
Publication of GB618889A publication Critical patent/GB618889A/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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Di-1-ethyl-benzimidazolylmethane is prepared by refluxing together N-ethyl-o-phenylenediamine and ethyl malonate. Di-1-methyl-benzimidazolylmethane is similarly prepared. Specification 610,064 is referred to.ALSO:N : N1-Alkylenecyanine dyes of the general formula <FORM:0618889/IV (c)/1> wherein R is alkyl, Z is unsubstituted or substituted o-phenylene, X is an anion, and n is 2 or 3, are prepared by heating a di-2-(1-alkyl)-benzimidazolyl)-methane with an ethylene- or propylene-diarylsulphonate and treating the product with an acid binding agent. Dyes where n is 1 are prepared by heating a di-2-(1-alkyl)-benzimidazolylmethane with a methylene halide and treating the product with an acid-binding agent. The dyes may be converted to the corresponding iodides, bromides, or perchlorates. The acid-binding agent may be a trialkyl amine, a dialkylamine, an N-alkylpiperidine, sodium hydroxide or carbonate, or ammonia. 1 : 11 - Diethyl - 3 : 31 - ethylenebenzimidazolocyanine iodide is prepared by heating together di-1-ethylbenzimidazolylmethane and ethylene p-toluenesulphonate, adding sodium hydroxide to an ethyl alcohol solution of the product, and adding alcoholic sodium iodide to an ethyl alcohol solution of the dye p-toluenesulphonate obtained. 1 : 11 - Diethyl - 3 : 31 - trimethylene - benzimidazolocyanine iodide and 1 : 11-dimethyl-3 : 31 - ethylenebenzimidazolocyanine iodide are similarly prepared. 1 : 11 - Diethyl - 3 : 31 - methylenebenzimidazolocyanine iodide is prepared by heating together di - 1 - ethylbenzimidazolylmethane and methylene iodide and adding aqueous sodium hydroxide to a methyl alcohol solution of the product. 1 : 11 - Dimethyl - 3 : 31 - methylene - benzimidazolocyanine iodide is similarly prepared. Specificatio 610,064 is referred to.
GB2191546A 1946-07-23 1946-07-23 Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyes Expired GB618889A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2191546A GB618889A (en) 1946-07-23 1946-07-23 Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2191546A GB618889A (en) 1946-07-23 1946-07-23 Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyes

Publications (1)

Publication Number Publication Date
GB618889A true GB618889A (en) 1949-03-01

Family

ID=10170934

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2191546A Expired GB618889A (en) 1946-07-23 1946-07-23 Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyes

Country Status (1)

Country Link
GB (1) GB618889A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3337579A (en) * 1961-09-15 1967-08-22 Upjohn Co Unsymmetrical 2, 2'-alkylene-bisbenzimidazoles
US3337578A (en) * 1961-09-15 1967-08-22 Heidenheimer Chemisches Lab 2, 2'-alkylenebisbenzimidazoles
GB2301832A (en) * 1995-06-07 1996-12-18 Univ Carnegie Mellon Rigidized monomethine cyanine dyes by cyclisation of di(heterocyclyl)methane precursors
US5852191A (en) * 1995-06-07 1998-12-22 Carnegie Mellon University Rigidized monomethine cyanines
US5981747A (en) * 1995-06-07 1999-11-09 Carnegie Mellon University Monomethine cyanines rigidized by a two-carbon chain
US8063032B2 (en) 2009-02-11 2011-11-22 Sunovion Pharmaceuticals Inc. Histamine H3 inverse agonists and antagonists and methods of use thereof

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3337579A (en) * 1961-09-15 1967-08-22 Upjohn Co Unsymmetrical 2, 2'-alkylene-bisbenzimidazoles
US3337578A (en) * 1961-09-15 1967-08-22 Heidenheimer Chemisches Lab 2, 2'-alkylenebisbenzimidazoles
GB2301832A (en) * 1995-06-07 1996-12-18 Univ Carnegie Mellon Rigidized monomethine cyanine dyes by cyclisation of di(heterocyclyl)methane precursors
GB2301832B (en) * 1995-06-07 1998-03-11 Univ Carnegie Mellon Rigidized monomethine cyanine dyes
US5852191A (en) * 1995-06-07 1998-12-22 Carnegie Mellon University Rigidized monomethine cyanines
US5981747A (en) * 1995-06-07 1999-11-09 Carnegie Mellon University Monomethine cyanines rigidized by a two-carbon chain
US5986093A (en) * 1995-06-07 1999-11-16 Carnegie Mellon University Monomethine cyanines rigidized by a two-carbon chain
US6207464B1 (en) 1995-06-07 2001-03-27 Carnegie Mellon University Rigidized monomethine cyanines
US6277984B1 (en) 1995-06-07 2001-08-21 Carnegie Mellon University Monomethine cyanines rigidized by a two-carbon chain
US8063032B2 (en) 2009-02-11 2011-11-22 Sunovion Pharmaceuticals Inc. Histamine H3 inverse agonists and antagonists and methods of use thereof
US8404670B2 (en) 2009-02-11 2013-03-26 Sunovion Pharmaceuticals Inc. Histamine H3 inverse agonists and antagonists and methods of use thereof

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