GB431187A - Improvements in or relating to the production of compounds containing a polymethine chain - Google Patents

Improvements in or relating to the production of compounds containing a polymethine chain

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Publication number
GB431187A
GB431187A GB1698535A GB1698535A GB431187A GB 431187 A GB431187 A GB 431187A GB 1698535 A GB1698535 A GB 1698535A GB 1698535 A GB1698535 A GB 1698535A GB 431187 A GB431187 A GB 431187A
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GB
United Kingdom
Prior art keywords
dimethyl
iodide
bromide
toluenesulphonate
phenylene
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
GB1698535A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB1698535A priority Critical patent/GB431187A/en
Publication of GB431187A publication Critical patent/GB431187A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0066Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Dyes containing a polymethine chain are prepared by reacting a body containing the grouping <FORM:0431187/IV/1> (wherein R1, R2, R3 may be hydrogen or the hydrocarbon groupings of a cyclopentadiene homologue or R1 and R2 may be part of an arylene residue as in indene) with a quaternary salt of a heterocyclic nitrogen compound containing as a reactive group a thioether or selenoether grouping. An alternative procedure comprises reacting the above 5-membered ring compound, heterocyclic nitrogen base and an alkyl salt together so as to form the quaternary salt simultaneously with the main reaction. Starting materials comprise cyclopentadiene and its homologues and indenes; on the other hand quaternary salts derived from heterocyclic nitrogen bases having reactive a - or g - alkyl-, aryl-, aralkyl thioether or selenoether or thione or selenone groupings and alkyl salts (the selenoether derivatives are obtained by heating an a - or g -chloro substituted heterocyclic nitrogen base with alcoholic selenourea followed by alkylation of the resulting selenomercaptan); reference is made to quaternary salts of alkyl-quinoline-2-thiones, alkylmercapto derivatives of quinolines, thiazoles, oxazoles, pyridines, diazoles, quinazolines, pyrimidines and phthalazines. Many of the dyes are useful for modifying the sensitivity of photographic emulsions (cf. Specification 431,142, [Group XX]), and some appear to be suitable for dyeing textiles. They are all regarded as carbocyanines in which the trimethine chain is itself part of a five-membered carbocyclic ring system. In examples: (1) 1 - methylmercaptobenzthiazole is heated with methyl- or ethyl-p-toluenesulphonate, cyclopentadiene and pyridine added with further heating, and the products precipitated as the bromide and iodide respectively by adding potassium bromide or iodide to give 2 . 2<1> - dimethyl ( - or - diethyl -) - 7 . 7<1> - dimethenylthiocarbocyanine bromide or iodide. By similar or analogous processes the following dyes are also made:--1 . 1<1> - dimethyl - and 1 . 1<1> - diethyl - 9 - 9<1> - dimethenyl - 2 . 2<1> - carbocyanine bromide from 1 - methyl - and 1 - ethyl - quinoline - 2 - thiones respectively, 2 . 2<1> - dimethyl (and - diethyl -) - 4 . 5 . 4<1> . 5<1> - tetraoxydimethylene - 7 . 7<1> - dimethenylthiocarbocyanine - p - toluene sulphonate from 1 - methylmercapto - 4 . 5 - dioxymethylenebenzthiazole, 2 . 2<1> - dimethyl - (and - diethyl -) 4 . 5 : 4<1> . 5<1> - tetramethoxy - 7 . 7<1> - dimethenyl-thiocarbocyanine - p - toluenesulphonate from 1 - methylmercapto - 4 . 5 - dimethoxybenzthiazole, thiocarbocyanines from dimethylmercapto - b . b <1> - thiodiazole (cf. Example 1 of Specification 425,609), cyclopentadiene and ethyl - and methyl - p - toluenesulphonates, 2 . 2<1> - dimethyl - 3 . 4 . 3<1> . 4<1> - dibenzo - 7 . 7<1> - dimethynylthiocarbocyanine - p - toluenesulphonate from 2 - methylmercapto - b - naphthothiazole, 2 . 2<1> - dimethyl - 7 . 7<1> - dimethenyloxacarbocyanine bromide from 1 - methylmercaptobenzoxazole; (2) 1 . 1<1> - dimethyl - 9 . 9<1> - o - phenylene - 2 . 2<1> - carbocyanine - p - toluenesulphonate is prepared by heating methylquinoline - 2 - thione with ethyl - p - toluenesulphonate and indene in presence of pyridine; by similar or analogous processes the following dyes are also obtained:--1 . 1<1> - diethyl - 9 . 9<1> - o - phenylene - 2 . 2<1> - carbocyanine bromide from 1 - ethylquinoline - 2 - thione, 2 . 2<1> - dimethyl - 7 . 7<1> - o - phenylenethiocarbocyanine iodide from 1 - methylmercaptobenzthiazole and 2 . 2<1> - diethyl - 7 . 7<1> - o - phenylenethiocarbocyanine p - toluenesulphonate and iodide from this base, 2 . 4 . 6 . 2<1> . 4<1> . 6<1> - hexamethyl - 7 . 7<1> - o - phenyleneoxacarbocyanine iodide from 1 - methylmercapto - 4 . 5 - dimethylbenzoxazole, dimethyl - o - phenylene - phthalazocarbocyanine iodide from methyl-mercaptophthalazine (prepared by heating phthazonic acid to give phthazone, treating this with phosphorus pentachloride and then with potassium hydrogen sulphide and finally methylating), 2 . 2<1> - dimethyl - 7 . 7<1> - o - phenyleneoxacarbocyanine iodide from 1-methylmercaptobenzoxazole, 2 . 2<1> - dimethyl - (and - diethyl -) - 4 . 5 . 4<1> . 5<1> - tetroxydimethylene - 7 . 7<1> - o - phenylenethiocarbocyanine - p - toluenesulphonate from 1 - methylmercapto - 4 . 5 - dioxymethylenebenzthiazole, 2 . 2<1> - dimethyl - 4 . 5 . 4<1> . 5<1> - tetramethoxy - 7 . 7<1> - o - phenylene - thiocarbocynic bromide from 1 - methylmercapto - 4 . 5 - dimethoxybenzthiazole, thiocarbocyanine dyes from dimethylmercapto - b .b <1> (and - a . b <1> -) - thiodiazoles, indene and methyl- and ethyl-p-toluenesulphonates, 1 . 1<1> - diethyl - 9 . 9<1> - o - phenylene - 4 . 4<1> - quinazocarbocyanine iodide and the corresponding dimethyl - p - toluenesulphonate, 2 . 2<1> - dimethyl - 3 . 4 . 3<1> . 4<1> - dibenzo - 7 . 7<1> - o - phenylene-thiocarbocyanine bromide, 3 . 3<1> - dimethyl - 2 . 2<1> - dimethylmercapto - o - phenylene - 4 . 4<1> - pyrimidocarbocyanine - p - toluenesulphonate and the corresponding diethyl-bromide compound, 1 . 1<1>-dimethyl - 7 . 7<1> - o - phenylene - 2 . 2<1> - pyridocarbocyanine iodide from 2-methylmercaptopyridine and 3 . 3<1> - dimethyl - 2 . 2<1> . 6 . 6<1> - tetramethylmercapto - o - phenylene - 4 . 4<1> - pyrimidocarbocyanine bromide from 2 . 4 . 6 . trimethylmercaptopyrimidine.
GB1698535A 1933-12-23 1933-12-23 Improvements in or relating to the production of compounds containing a polymethine chain Expired GB431187A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1698535A GB431187A (en) 1933-12-23 1933-12-23 Improvements in or relating to the production of compounds containing a polymethine chain

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1698535A GB431187A (en) 1933-12-23 1933-12-23 Improvements in or relating to the production of compounds containing a polymethine chain

Publications (1)

Publication Number Publication Date
GB431187A true GB431187A (en) 1935-06-24

Family

ID=10087153

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1698535A Expired GB431187A (en) 1933-12-23 1933-12-23 Improvements in or relating to the production of compounds containing a polymethine chain

Country Status (1)

Country Link
GB (1) GB431187A (en)

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