GB646900A - Thiazolone cyanine dyes and the method of preparing the same - Google Patents

Thiazolone cyanine dyes and the method of preparing the same

Info

Publication number
GB646900A
GB646900A GB20812/48A GB2081248A GB646900A GB 646900 A GB646900 A GB 646900A GB 20812/48 A GB20812/48 A GB 20812/48A GB 2081248 A GB2081248 A GB 2081248A GB 646900 A GB646900 A GB 646900A
Authority
GB
United Kingdom
Prior art keywords
thioacetanilide
acid
ethyl
butanol
ethylbenzthiazolylidene
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
GB20812/48A
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.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
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 General Aniline and Film Corp filed Critical General Aniline and Film Corp
Publication of GB646900A publication Critical patent/GB646900A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Substituted thioamides of the general formula <FORM:0646900/IV (b)/1> wherein A1 is the residue of a heterocyclic nucleus having 5 or 6 atoms in the heterocyclic ring, R2 is alkyl, allyl, aryl, or aralkyl, R3 is alkyl or aralkyl, and m is 1 or 2, are prepared by condensing a heterocyclic quaternary ammonium salt containing a reactive methyl group in the a - or g -position to the quaternary N atom with an alkyl, allyl, aryl, or aralkyl isothiocyanate in the presence of a base such as triethylamine or pyridine. a -(3-Ethylbenzthiazolylidene)-thioacetanilide is prepared by heating together 2-methylbenzthiazole and ethyl p-toluenesulphonate, pouring the product into a solution of phenyl isothiocyanate in pyridine, and stirring and heating. a -(3-Methyl-6-methoxybenzthiazolylidene)-thioacetanilide is prepared by mixing together 2-methyl-6-methoxybenzthiazole methyl p-toluenesulphonate, methanol, phenyl isothiocyanate, and triethylamine, and allowing to stand. a -(1-Ethyl-3 : 3 : 5-trimethylindolinylidene) - thioacetanilide, a - (3 - ethylbenzthiazolylidene)-N-allylthioacetamide, a -(3-ethyl-5-methoxybenzselenazolylidene) - thioacetanilide, a - (3 - ethyl - 4 : 5 - diphenyloxazolylidene) - thioacetanilide, a - (3 - ethyl - 5 : 6 - dimethylbenzoxazolylidene) - thioacetanilide, a - (3 - ethylbenzthiazolylidene)-thioacet-o-toluidide, a -(3-ethyl6 - methoxybenzthiazolylidene) - thioacet - a - naphthalide, a - (3 - ethylbenzthiazolylidene) - N - ethylthioacetamide, a - (3 : 6 - dimethylbenzthiazolylidene) - thioacetanilide, a - (3 - ethyl - 6 - methoxybenzthiazolylidene) - thioacet - b - naphthalide, a - (1 - methyl - 2 - quinolylidene) - thioacetanilide, a - (3 - methylbenzselenazolylidene) - thioacetanilide, and a - (3 - ethyl - 5 - methyl - 4 - phenylthiazolylidene) - thioacetanilide are similarly prepared. Specification 646,896 is referred to.ALSO:A thiazolone cyanine dye is prepared by heating a substituted thioamide of the general formula <FORM:0646900/IV (c)/1> wherein A1 is the residue of a heterocyclic nucleus having 5 or 6 carbon atoms in the heterocyclic ring, R2 is alkyl, allyl, aryl, or aralkyl, R3 is alkyl or aralkyl, and m is 1 or 2, with an a -halogen- or a : a -dihalogen-acetic acid or with an a -halogenpropionic acid. The reactants may be heated together in a bomb or sealed tube or may be refluxed or heated together with an alcohol or acetic acid or anhydride. Numerous thioamides are specified. Dyes are prepared by heating together: (1) a - (3 - ethylbenzthiazolylidene) - thioacetanilide and bromacetic acid in n-butanol; (2) a - (3 - methyl - 6 - methoxybenzthiazolylidene)-thioacetanilide and bromacetic acid in n-butanol; (3) a - (1 - ethyl - 3 : 3 : 5 - trimethylindolinylidene)-thioacetanilide and bromacetic acid in n-butanol; (4) a -(3-ethylbenzthiazolylidene)-N-allylthioacetamide and chloracetic acid in n-butanol; (5) a -(3-ethyl-5-methoxybenzselenazolylidene) - thioacetanilide and bromacetic acid in n-butanol; (6) a -(3-ethylbenzthiazolylidene)-thioacet-o-toluidide and bromacetic acid in n-butanol; (7) a -(3-ethyl-6-methoxybenzthiazolylidene) - thioacet - a - naphthalide and bromacetic acid in n-butanol; (8) a -(3-ethylbenzthiazolylidene) - N - ethylthioacetamide and bromacetic acid in acetic acid; (9) a - (3 - ethyl - 6 - methoxybenzthiazolylidene)-thioacet-b -naphthalide and bromacetic acid in n-butanol; (10) a -(3 : 6-dimethylbenzthiazolylidene)-thioacetanilide and bromacetic acid in n-butanol; (11) a -(3-ethyl-5-methyl-4-phenylthiazolylidene)-thioacetanilide and bromacetic acid in acetic acid; (12) a -(3-methylbenzselenazolylidene) - thioacetanilide and bromacetic acid in n-butanol; (13) a -(1-methyl-2-quinolylidene) - thioacetanilide and bromacetic acid in n-butanol; (14) a -(3-ethylbenzthiazolylidene) - thioacetanilide and a - chloropropionic acid in n-propanol; (15) a -(3-ethylbenzthiazolylidene)-thioacetanilide and dichloracetic acid in n-propanol; (16) a -(3-ethyl-4 : 5-diphenyloxazolylidene)-thioacetanilide and bromacetic acid in p acetic acid; and (17) a -(3-ethyl-5 : 6 - dimethylbenzoxazolylidene) - thioacetanilide and bromacetic acid in acetic acid. The dyes may be converted to iodides, perchlorates, or thiocyanates. Specification 646,896 is referred to.
GB20812/48A 1947-11-18 1948-08-06 Thiazolone cyanine dyes and the method of preparing the same Expired GB646900A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US646900XA 1947-11-18 1947-11-18

Publications (1)

Publication Number Publication Date
GB646900A true GB646900A (en) 1950-11-29

Family

ID=22057655

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20812/48A Expired GB646900A (en) 1947-11-18 1948-08-06 Thiazolone cyanine dyes and the method of preparing the same

Country Status (1)

Country Link
GB (1) GB646900A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4885366A (en) * 1988-06-08 1989-12-05 Eastman Kodak Company Novel selenium-containing merocyanine dyes
US4937344A (en) * 1988-06-08 1990-06-26 Eastman Kodak Company Novel sulfur-containing merocyanine dyes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4885366A (en) * 1988-06-08 1989-12-05 Eastman Kodak Company Novel selenium-containing merocyanine dyes
US4937344A (en) * 1988-06-08 1990-06-26 Eastman Kodak Company Novel sulfur-containing merocyanine dyes

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