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GB742112A - Improvements in the preparation of cyanine and styryl dyestuffs - Google Patents

Improvements in the preparation of cyanine and styryl dyestuffs

Info

Publication number
GB742112A
GB742112A GB26665/52A GB2666552A GB742112A GB 742112 A GB742112 A GB 742112A GB 26665/52 A GB26665/52 A GB 26665/52A GB 2666552 A GB2666552 A GB 2666552A GB 742112 A GB742112 A GB 742112A
Authority
GB
United Kingdom
Prior art keywords
sulpho
anhydro
hydroxide
methyl
butyl
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
GB26665/52A
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.)
Agfa Gevaert NV
Original Assignee
Agfa AG
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 Agfa AG filed Critical Agfa AG
Publication of GB742112A publication Critical patent/GB742112A/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
    • C09B23/14—Styryl dyes
    • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
    • 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
    • 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
    • C09B23/16—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms
    • C09B23/162—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
    • C09B23/164—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms containing one nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

Anhydro - 2 - methyl - 3 - o - sulpho - n - butyl-benzthiazolium hydroxide is prepared by heating together 2-methylbenzthiazole and butane-sultone. Anhydro - 2 - methylmercapto - 3 - o -sulpho - n - butylbenzthiazolium hydroxide, anhydro - 2 - methyl - 1 - o - sulpho - n - butylquinolinium hydroxide, anhydro - 2 - methyl - 3-o - sulpho - n - butylbenzselenazolium hydroxide, anhydro - 2 - methyl - 3 - o - sulpho - n - butyl - 5-methoxybenzselenazolium hydroxide, anhydro-2 : 5 : 6 - trimethyl - 3 - o - sulpho - n - butylbenzthiazolium hydroxide, anhydro - 2 - methyl - 3-g - sulpho: g - methyl - n - butylbenzthiazolium hydroxide, anhydro - 2 - methyl - 3 - o - sulpho-n - butyl - 5 - chlorobenzthiazolium hydroxide, and anhydro - 2 - methyl - 3 - o - sulpho - n - propyl - 5 - chlorobenzthiazolium hydroxide are similarly prepared. Anhydro - 2 - b - N - methylanilinovinyl - 3-o - sulpho - n - butylbenzthiazolium hydroxide is prepared by adding methyldiphenylformamidine to a suspension of anhydro-2-methyl-3-o -sulpho-n-butylbenzthiazolium hydroxide in methanol and ethanol, and heating. Specification 654,690, [Group IV (c)], is referred to.ALSO:Cyanine and styryl dyes in which at least one heterocyclic nitrogen atom carries a sulpho-alkyl group as the sole substituent are prepared by reacting an alkane sultone containing at least three carbon atoms with a heterocyclic base having in the a- or g -position to the nitrogen atom of the heterocyclic ring or alkyl, thioalkyl, b -alkyl thiovinyl, b -halogenovinyl, b -(N-methylanilino)-vinyl, or b -acylanilidovinyl substituent, including similar substituents in which the vinyl groups are substituted by alkyl, aralkyl or aryl groups, and treating the reaction product by a method known to be capable of converting the heterocyclic nitrogen base into a cyanine or styryl dye. Mono-, tri-, and penta-methine and rhodacyanine dyes and styryl dyes are referred to. Anhydro-11-ethyl-3-o -Sulpho-n-butylthia-21 cyanine hydroxide is prepared either by heating together 1-ethyl-2-methylmercaptoquinolinium methosulphate, anhydro-2-methyl-3-o -sulpho - n - butylbenzthiozolium hydroxide, absolute ethanol, and triethylamine, or by heating together 1-ethylquinaldinium, p-toluene sulphonate, anhydro-2-methylmercapto - 3 - o -sulpho-n-butylbenzthiazolium hydroxide, absolute ethanol, and triethylamine. Anhydro-11-ethyl-61-methyl-3-o -sulpho-n-butylthia - 21 - cyanine hydroxide, anhydro-31-methyl-1-o -sulpho-n-butylquina-2-thiocyanine hydroxide, anhydro-3-ethyl-31-o -sulpho-n-butylthiacarbocyanine hydroxide, anhydro-3-ethyl - 31 - o -sulpho-n-butylthiaselenacarbocyanine hydroxide, anhydro-31-ethyl-41-(N : N1 dimethylbenzimidazolylidenei-51keto-41 : 51 - dihydro-3-o -sulpho-n-butylthiazolothia - cyanine hydroxide, anhydro-31 : 9-diethyl-51 : 61-dimethyl-3-o -sulpho-n-butyl - thiacarbocyanine hydroxide, anhydro-31 : 9-diethyl-51 : 61-dimethyl-3-o -sulpho-n-butyl - thiacar - oxythiaselenacarbocyanine hydroxide, anhydro-2-p-dimethylaminostyryl-3- o -sulpho-n-butyl - 5 : 6 - dimethylbenzthiazolium hydroxide, anhydro-11-ethyl-3-g -sulpho:g -methyl-n-butyl thia-21-cyanine hydroxide, anhydro-3-ethyl-31-g -sulpho : g - methyl - n - propyl - 9 - ethylselenethia - carbocyanine hydroxide, anhydro-3 : 31-di-o -sulpho - n - butyl- 5 : 51-diphenyl-9-ethyloxacarbocyanine hydroxide, anhydro-3-ethyl-5:51-dichloro - 31 - o -sulpho-n-butyl-9-ethylthiacarbocyanine hydroxide, and anhydro-3:31-di-o -sulpho-n-propyl-5 : 51 - dichloro - 9 - ethylthiacarbocyanine hydroxide are similarly prepared. Specification 654,690 is referred to.
GB26665/52A 1951-10-23 1952-10-23 Improvements in the preparation of cyanine and styryl dyestuffs Expired GB742112A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE321879X 1951-10-23

Publications (1)

Publication Number Publication Date
GB742112A true GB742112A (en) 1955-12-21

Family

ID=6163974

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26665/52A Expired GB742112A (en) 1951-10-23 1952-10-23 Improvements in the preparation of cyanine and styryl dyestuffs

Country Status (4)

Country Link
BE (1) BE515014A (en)
CH (1) CH321879A (en)
FR (1) FR1073968A (en)
GB (1) GB742112A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3177210A (en) * 1962-11-29 1965-04-06 Polaroid Corp Process for preparing cyanine spectral sensitizing dyes
US3288610A (en) * 1963-10-26 1966-11-29 Agfa Ag Optically sensitized photographic silver halide emulsions
US3352857A (en) * 1962-03-19 1967-11-14 Eastman Kodak Co Solubilized cyanine and merocyanine sensitizing dyes
US3372160A (en) * 1963-05-17 1968-03-05 Ilford Ltd Cyanine dyes
US3424586A (en) * 1963-06-10 1969-01-28 Agfa Ag Silver halide emulsions sensitized with cyanine dyes containing a hydroxypropyl sulfonic acid radical
US3481927A (en) * 1964-09-01 1969-12-02 Eastman Kodak Co Butadienyl dyes for photography
US3649289A (en) * 1968-10-21 1972-03-14 Eastman Kodak Co Photographic materials
US3660103A (en) * 1964-04-21 1972-05-02 Agfa Gevaert Ag Spectral sensitization by polymethine dyes which contain an unsaturated alkyl sulfonic acid group
US3759931A (en) * 1970-10-27 1973-09-18 Ilford Ltd New merocyanine dyestuffs

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3352857A (en) * 1962-03-19 1967-11-14 Eastman Kodak Co Solubilized cyanine and merocyanine sensitizing dyes
US3177210A (en) * 1962-11-29 1965-04-06 Polaroid Corp Process for preparing cyanine spectral sensitizing dyes
US3372160A (en) * 1963-05-17 1968-03-05 Ilford Ltd Cyanine dyes
US3424586A (en) * 1963-06-10 1969-01-28 Agfa Ag Silver halide emulsions sensitized with cyanine dyes containing a hydroxypropyl sulfonic acid radical
US3288610A (en) * 1963-10-26 1966-11-29 Agfa Ag Optically sensitized photographic silver halide emulsions
US3660103A (en) * 1964-04-21 1972-05-02 Agfa Gevaert Ag Spectral sensitization by polymethine dyes which contain an unsaturated alkyl sulfonic acid group
US3481927A (en) * 1964-09-01 1969-12-02 Eastman Kodak Co Butadienyl dyes for photography
US3649289A (en) * 1968-10-21 1972-03-14 Eastman Kodak Co Photographic materials
US3759931A (en) * 1970-10-27 1973-09-18 Ilford Ltd New merocyanine dyestuffs

Also Published As

Publication number Publication date
FR1073968A (en) 1954-09-30
CH321879A (en) 1957-05-31
BE515014A (en)

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