GB610064A - Improvements in methods of making cyanine dyes and in photographic emulsions containing them - Google Patents

Improvements in methods of making cyanine dyes and in photographic emulsions containing them

Info

Publication number
GB610064A
GB610064A GB3090145A GB3090145A GB610064A GB 610064 A GB610064 A GB 610064A GB 3090145 A GB3090145 A GB 3090145A GB 3090145 A GB3090145 A GB 3090145A GB 610064 A GB610064 A GB 610064A
Authority
GB
United Kingdom
Prior art keywords
di
prepared
benzthiazolylidene
heating
iodide
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
GB3090145A
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 GB3090145A priority Critical patent/GB610064A/en
Publication of GB610064A publication Critical patent/GB610064A/en
Application status is Expired legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04Methine 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

Abstract

Di-2-benzoxazolylmethane is prepared by refluxing together o-aminophenol and ethyl malonate, a stream of CO2 gas being passed through the apparatus. Di-2-benzthiazolylmethane and di-2-benzselenazolylmethane are similarly prepared. 2-Benzthiazolyl-2-quinolylmethane is prepared by refluxing together 2-chlorobenzthiazole and quinaldine. Di - 2 - benzthiazolyl - 2 - quinolyl - methane is obtained as a by-product. 2 - (3 - b - Bromoethyl - 2 - benzthiazolylidene) - methylbenzthiazole is prepared by heating together 2 - (3 - b - hydroxyethyl - 2 - benzthiazolylidene)-methylbenzthiazole and phosphorus tribromide. 2-(3-b -Bromoethyl-2-benzthiazolylidene) - methylquinoline and 2 - (3 - g - bromo - propyl - 2 - benzthiazolylidene) - methylbenzthia - zole are similarly prepared. 2 - (3 - b - Hydroxyethyl - 2 - benzthiazolylidene)-methylbenzthiazole is prepared by heating together di-2-benzthiazolylmethane and ethylene bromohydrin, and rendering alkaline with ammonium hydroxide. 2 - (3 - g - Hydroxy - propyl - 2 - benzthiazolylidene) - methylbenzthia - zole is similarly prepared from di - 2 - benz - thiazolylmethane and trimethylenebromo - hydrin. 2 - (3 - b - Hydroxyethyl - 2 - benzthiazolylidene)-methylquinoline is prepared by refluxing together 2 - methylbenzthiazole b - hydroxyethobromide and 2-methylmercaptoquinoline, and adding triethylamine.ALSO:A cyanine dye of the general formula <FORM:0610064/IV (c)/1> wherein Z and Z1 each represent the nonmetallic atoms necessary to complete a 5- or 6-membered heterocyclic ring, X represents an anion, and n is 2 or 3 is prepared by heating a di-heterocyclylmethane of the general formula <FORM:0610064/IV (c)/2> with an ethylene or propylene arylsulphonate, and then treating the product with an acid-binding agent. The dye may also be prepared by heating an N-bromoethyl or N-bromopropyl cyanine base of the general formula <FORM:0610064/IV (c)/3> The heating may be effected at from 150 DEG to 200 DEG C., and the acid-binding agent may be a trialkylamine, a dialkylamine, an N-alkylpiperidine, sodium carbonate or ammonia. The dye arylsulphonates obtained in the first method may be converted to iodides, bromides, or perchlorates, and the dye bromides obtained in the second process may be converted to iodides or perchlorates. The bromides or iodides may be converted into chlorides by treatment with silver chloride in a phenol. 3 : 31-Ethylenethiacyanine iodide is prepared by heating together di-2-benzthiazolylmethane and ethylene di-p-toluenesulphonate, suspending the product in hot methyl alcohol and adding triethylamine, and adding a hot methyl alcohol solution of sodium iodide. 1 : 11-Ethylene-2 : 11-cyanine iodide, and 3 : 31-ethyleneoxacyanine iodide are similarly prepared, and dyes can be obtained similarly from di-2-benzselenazolylmethane, di-2-(4-thiazolyl)-methane, di-2-(4-phenylthiazolyl) - methane, di - 2 - (5 - methyl - benzoxazole) - methane, 2 - benzthiazolyl - 2 - quinolylmethane and 2 - benzoxazolyl - 2 - benzthiazolylmethane. 3 : 31-Propylenethiacyanine bromide is prepared by heating 2-(3-bromopropyl-2-benzthiazolylidene)-methylbenzthiazole. 3 : 31-Ethylenethiacyanine iodide and 11 : 3-ethylenethia-21-cyanine iodide are similarly prepared.
GB3090145A 1945-11-17 1945-11-17 Improvements in methods of making cyanine dyes and in photographic emulsions containing them Expired GB610064A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3090145A GB610064A (en) 1945-11-17 1945-11-17 Improvements in methods of making cyanine dyes and in photographic emulsions containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3090145A GB610064A (en) 1945-11-17 1945-11-17 Improvements in methods of making cyanine dyes and in photographic emulsions containing them

Publications (1)

Publication Number Publication Date
GB610064A true GB610064A (en) 1948-10-11

Family

ID=10314868

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3090145A Expired GB610064A (en) 1945-11-17 1945-11-17 Improvements in methods of making cyanine dyes and in photographic emulsions containing them

Country Status (1)

Country Link
GB (1) GB610064A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0747448A2 (en) * 1995-06-07 1996-12-11 Carnegie Mellon University 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

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0747448A2 (en) * 1995-06-07 1996-12-11 Carnegie Mellon University Rigidized monomethine cyanine dyes
GB2301832A (en) * 1995-06-07 1996-12-18 Univ Carnegie Mellon Rigidized monomethine cyanine dyes by cyclisation of di(heterocyclyl)methane precursors
EP0747448A3 (en) * 1995-06-07 1997-03-05 Univ Carnegie Mellon Rigidized monomethine cyanine dyes
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

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