GB806817A - Heterocyclic polymethine dyes - Google Patents

Heterocyclic polymethine dyes

Info

Publication number
GB806817A
GB806817A GB2326856A GB2326856A GB806817A GB 806817 A GB806817 A GB 806817A GB 2326856 A GB2326856 A GB 2326856A GB 2326856 A GB2326856 A GB 2326856A GB 806817 A GB806817 A GB 806817A
Authority
GB
United Kingdom
Prior art keywords
butyl
methyl
indoline
methylene
alkyl
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
GB2326856A
Inventor
Alistair Howard Berrie
Henry Alfred Piggott
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2326856A priority Critical patent/GB806817A/en
Publication of GB806817A publication Critical patent/GB806817A/en
Expired legal-status Critical Current

Links

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
    • C09B23/16Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms
    • C09B23/162Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
    • C09B23/164Methine 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)

Abstract

Diaryl, diindolinyl and diquinolinyl alkanes of the general formula <FORM:0806817/IV (b)/1> where R and R1 are the same or different and are hydrogen or alkyl or may be joined together to form with the carbon atom a cycloalkyl ring which may contain alkyl substituents, R2 is alkyl or alkylene which is connected to the ring A in a position ortho to the nitrogen atom to form a heterocyclic ring, and rings A may be substituted, are made by reacting a cycloalkanone or an aliphatic aldehyde or ketone and at least 2 molecular proportions of an N-alkyl derivative of an aniline, or an indoline or a tetrahydroquinoline at elevated temperature in a medium containing at least one equivalent of acid for each molecular proportion of amine. Hydrochloric acid may be used. Aldehydes and ketones specified are cyclopentanone, cyclohexanone, 3-methylcyclohexanone, formaldehyde, acetaldehyde, n-butyraldehyde, acetone, methyl ethyl ketone and methyl n-butyl ketone. Amines mentioned are N-ethylaniline, N-methyl-o-toluidine, N-n-butylaniline, indoline, 2-methyl indoline and 8-chloro-tetrahydroquinoline. Examples describe the preparation of: (I) bis-(2-methyl-5-indolinyl-) methane; and (II) 2 : 2-bis-(1 : 2 : 3 : 4-tetrahydro-6-quinolyl)-propane. Bis - (1 : 2 : 3 : 4 - tetrahydro - 6 - quinolyl-) - methane disulphonic acid is made by sulphonating bis - (1 : 2 : 3 : 4 - tetrahydro - 6 - quinolyl-)-methane with 20 per cent oleum. 2 - Aldehydo - methylene - 1 : 3 : 3 - trimethyl indolines containing an n-butyl group or a chlorine atom in the 5-position, and 2-aldehydo - methylene - 1 - n - butyl - 3 : 3 - dimethyl indoline are made by reacting 5-butyl- or 5-chloro - 2 - methylene - 1 : 3 : 3 - trimethyl indoline or 1-n-butyl-3 : 3-dimethyl-2-methylene indoline with N : N - formyl - methyl aniline and phosphorus oxychloride by the method of Specification 438,278 for the preparation of 2-aldehydo-methylene-1 : 3 : 3-trimethyl indoline. 2 - Aldehydo - methylene - 1 : 3 : 3 - trimethyl indoline sulphonic acid is made by sulphonating 2 - aldehydo - methylene - 1 : 3 : 3 - trimethyl indoline with oleum. 5 - Butyl - and 5 - chloro - 2 - methylene - 1 : 3 : - trimethyl indolines are made by the method of Plancher, Chemiker-Zeitung 1898, page 38, for making 2-methylene-1 : 3 : 3-trimethyl indoline by replacing the phenyl hydrazine by equivalent amounts of 4-n-butyl-and 4-chloro-phenyl hydrazines respectively.ALSO:The invention comprises greenish-yellow wool dyes of the formula (I) <FORM:0806817/IV (c)/1> or the alkali-metal salts thereof wherein R and R1 may be the same or different and are hydrogen or alkyl or may be joined together to form with the carbon atom a cycloalkyl ring which may contain alkyl substituents, R2 is alkyl or alkylene which is connected to ring A in a position ortho to the nitrogen to form a heterocyclic ring, R3, T4 and R5 are alkyl and may be the same or different, and rings A and B may be further substituted. The invention further comprises processes for preparing the dyes by sulphonating a compound of the formula (II) <FORM:0806817/IV (c)/2> where X is an anion, such as hydroxy, chloride or sulphate, or by reacting together in acid medium one molecular proportion of a compound of the formula (III) <FORM:0806817/IV (c)/3> and at least two molecular proportions of a compound of the formula (IV) <FORM:0806817/IV (c)/4> provided that each of rings A and B contains not more than one sulphonic acid group, and sulphonating any compound so obtained which contains less than four sulphonic acid groups. The interaction and sulphonation may be carried out in a single operation. The sulphonation may be effected by stirring the compound in oleum at between 0 DEG and 100 DEG C. until a test portion is readily soluble in 50 to 100 parts of cold water. Alkyl groups specified as R and R1 are methyl, ethyl and n-butyl, and cycloalkyl rings formed when R and R1 are joined may be cyclopentane, cyclohexane and methyl cyclohexane. R3, R4 and R5 may be methyl, n-butyl and n-octyl, and R2 may be methyl, ethyl and n-butyl and, when alkylene, may be ethylene, trimethylene and propylene. Substituents present in rings A and B may be methyl, n-butyl, n-octyl, methoxy, carbethoxy, acetamido, propionamido, chlorine and bromine. Compounds of the above general formula II are made by reacting one molecular proportion of the compound of formula (III) with 2 molecular proportions of the compound of formula (IV), both rings A and B being unsulphonated, at elevated temperatures in an acidic medium such as aqueous hydrochloric or sulphuric acid, glacial acetic acid either alone or containing small amounts of hydrochloric or sulphuric acid, or solutions of phosphorus oxychloride in benzene or monochlorobenzene. Examples are given. Specification 438,278, [Group IV], is referred to.
GB2326856A 1956-07-27 1956-07-27 Heterocyclic polymethine dyes Expired GB806817A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2326856A GB806817A (en) 1956-07-27 1956-07-27 Heterocyclic polymethine dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2326856A GB806817A (en) 1956-07-27 1956-07-27 Heterocyclic polymethine dyes

Publications (1)

Publication Number Publication Date
GB806817A true GB806817A (en) 1958-12-31

Family

ID=10192921

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2326856A Expired GB806817A (en) 1956-07-27 1956-07-27 Heterocyclic polymethine dyes

Country Status (1)

Country Link
GB (1) GB806817A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9296857B2 (en) 2010-03-24 2016-03-29 Hexcel Composites Limited Curing agents
CN117089222A (en) * 2023-08-22 2023-11-21 浙江闰土股份有限公司 Cationic yellow dye and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9296857B2 (en) 2010-03-24 2016-03-29 Hexcel Composites Limited Curing agents
CN117089222A (en) * 2023-08-22 2023-11-21 浙江闰土股份有限公司 Cationic yellow dye and preparation method thereof

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