GB466245A - Improvements in the manufacture of carbocyanine dyes - Google Patents

Improvements in the manufacture of carbocyanine dyes

Info

Publication number
GB466245A
GB466245A GB2511636A GB2511636A GB466245A GB 466245 A GB466245 A GB 466245A GB 2511636 A GB2511636 A GB 2511636A GB 2511636 A GB2511636 A GB 2511636A GB 466245 A GB466245 A GB 466245A
Authority
GB
United Kingdom
Prior art keywords
formylmethylene
ethiodide
methyl
quinaldine
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
GB2511636A
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.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
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 Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to GB2511636A priority Critical patent/GB466245A/en
Publication of GB466245A publication Critical patent/GB466245A/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
    • C09B23/06—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)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

Carbocyanine dyes are made by condensing a quaternary cyclammonium salt containing a reactive a - or g -alkyl group with a formylmethylene compound having the formula <FORM:0466245/IV/1> where V = a chain of two carbon atoms which may form part of a benzene or naphthalene nucleus, Y = O, S, Se or <FORM:0466245/IV/2> , and R = alkyl. a -Formylmethylene compounds derived from a thiazole, e.g. 4-phenylthiazole, a selenazole, a benzthiazole, a benzselenazole, a naphthathiazole or from oxazoles such as benzoxazole and naphthoxazole, thiazolines, selenazolines, pyridines or quinolines, e.g. 5-methylquinoline or a benzquinoline are mentioned. In examples, (1)--(3) 1-ethyl-2-formylmethylene-b -naphthathiazoline is condensed in acetic anhydride with quinaldine ethiodide, lepidine ethiodide or 1-methylbenzoxazole ethiodide; (4) 2-formylmethylene-1-methyl-1 : 2-dihydroquinoline is similarly condensed with 2-methyl-b -naphthathiazole ethiodide. Quaternary salts of quinaldine, lepidine, a - and g -picoline, 1-methybenzthiazole, 2-methyl-a -and b -naphthathiazoles, 1-methylbenzselenazole, 2-methylthiazoles, 2-methylthiazoline, 2 : 3 : 3-trimethylindolenine, 1-methyl-benzoxazole and methyla - and b -naphthoxazole are mentioned. The dyes are useful for sensitizing gelatino-silver halide photographic emulsions, in the construction of light-filters and may be used for textiles, particularly cellulose acetate. Specification 466,268 is referred to. Samples have been furnished under Sect. 2 (5) of the dyestuffs (1) 1<1>-ethyl-3 : 4-dimethylthiazolo-2<1>-carbocyanine iodide (formula given) made by condensing 2-formylmethylene-3 : 4-dimethyl-D <4>-thiazoline with quinaldine ethiodide in acetic anhydride; (2) 1<1>-ethyl-3-methylthiazolino-2<1>-carbocyanine iodide (formula given) made similarly from 2-formylmethylene-3-methylthiazolidine and quinaldine ethiodide. According to the Provisional Specification the starting materials are formylmethylene derivatives of the dihydro derivatives of heterocyclic compounds having a substituent on a nitrogen atom in the nucleus.
GB2511636A 1935-08-15 1935-08-15 Improvements in the manufacture of carbocyanine dyes Expired GB466245A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2511636A GB466245A (en) 1935-08-15 1935-08-15 Improvements in the manufacture of carbocyanine dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2511636A GB466245A (en) 1935-08-15 1935-08-15 Improvements in the manufacture of carbocyanine dyes

Publications (1)

Publication Number Publication Date
GB466245A true GB466245A (en) 1937-05-18

Family

ID=10222463

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2511636A Expired GB466245A (en) 1935-08-15 1935-08-15 Improvements in the manufacture of carbocyanine dyes

Country Status (1)

Country Link
GB (1) GB466245A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3723419A (en) * 1967-05-17 1973-03-27 Eastman Kodak Co Preparation of formylmethylene compounds and corresponding photographic dyestuffs

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3723419A (en) * 1967-05-17 1973-03-27 Eastman Kodak Co Preparation of formylmethylene compounds and corresponding photographic dyestuffs

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