GB432628A - Improvements in or relating to the production of compounds containing an ethylenic linkage, or a polymethine chain - Google Patents
Improvements in or relating to the production of compounds containing an ethylenic linkage, or a polymethine chainInfo
- Publication number
- GB432628A GB432628A GB1698635A GB1698635A GB432628A GB 432628 A GB432628 A GB 432628A GB 1698635 A GB1698635 A GB 1698635A GB 1698635 A GB1698635 A GB 1698635A GB 432628 A GB432628 A GB 432628A
- Authority
- GB
- United Kingdom
- Prior art keywords
- condensed
- indanedione
- give
- group
- heterocyclic
- 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
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
- C09B23/10—The polymethine chain containing an even number of >CH- groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Compounds containing an ethylenic linkage or a polymethine chain are prepared by reacting an organic compound containing a ketomethylene (--COCH2--) group and which may be represented by one of the following general formul <FORM:0432628/IV/1> or <FORM:0432628/IV/2> (wherein X stands for C, S or O), with a quaternary salt of a heterocyclic nitrogen compound containing as a reactive group an aryl-, alkyl-, or aralkyl-thioether or -selenoether, an aminovinyl, an arylaminovinyl, an acetaminovinyl, an acetarylaminovinyl or a halogen group. Alternatively, the organic compound containing the ketomethylene grouping, the heterocyclic nitrogen base and an alkyl salt are mixed together and heated to effect quaternary salt formation simultaneously with the main condensation reaction. Also such products are obtained by condensing with a heterocyclic quaternary ammonium salt having a reactive group, the condensation product of the compound containing the ketomethylene group and a formamidine or a formimino ether. As starting materials the following ketomethylene compounds are mentioned: indanedione, a - and b -hydrindone, tetronic acid, a - and b -keto - dihydrothionaphthene, naphthathioindoxyls, ethoxythioindoxyls, a - and b -ketodihydrocoumarone; also for reaction therewith there may be used heterocyclic quaternary ammonium salts having thioether or selenoether groupings in a - or g -position or compounds formed by treating the corresponding N-alkyl thiones with alkyl salts (the selenoether derivatives are prepared by heating a - or g -chloro substituted heterocyclic nitrogen bases with alcoholic selenourea, followed by saponification and alkylation), and compounds formed by condensing formamidines or aryl-formamidines with quaternary salts of heterocyclic nitrogen bases having a reactive methyl group. Many of the products are useful for mixing with photographic emulsions for modifying the light-sensitivity while others may be of use as textile dyes. In examples, (1) 1,3-indanedione is condensed with diphenylformamidine in acetic anhydride and the product with 1-methylbenzthiazole ethyl - p - toluenesulphonate, lepidine methiodide and quinaldine ethiodide to give products which are represented as having a dimethenyl linkage, indanedione and heterocyclic radicles; (2) indanedione is condensed with 1-methylmercaptobenzthiazole ethiodide in pyridine to give N-ethyldihydrobenzthiazolyl-1<1>.2 - indane - 1.3 - dione; (3) 2 - hydrindone (derived from indene by bromination according to Walters's method, followed by treatment with alcoholic caustic potash and steam distillation from an acidified solution) is condensed with acetanilidovinylbenzthiazole ethiodide to give N - ethyldihydrobenzthiazolyl-1<1>.1-dimethenylindane-2-one; (4) 1-hydrindone is condensed with the product of 1-methylquinoline-2-thione and ethyl-p-toluenesulphonate to give N-methyldihydroquinolyl - 2.2<1> - indane - 1 -one. Samples have been furnished under Sect. 2 (5) of products prepared as follows: (a) 1-methylmercaptobenzthiazole condensed with methyl-p-toluenesulphonate and the product further condensed with hydroxythiotolene (a -oxy-a <1>-methylthiophene); (b) b -courmaranone concondensed with 2-iodoquinoline ethiodide in presence of sodium ethoxide; (c) 2-methyl-selenomercaptoquinoline (prepared by reacting 2-chloroquinoline with selenourea (from cyanamide and hydrogen selenide) saponifying and methylating) is condensed with methyl-p-toluenesulphonate and then further heated with 1.3-indanedione to give N-methyldihydroquinolyl-2,2-indane-1,3-dione.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1698635A GB432628A (en) | 1933-12-23 | 1933-12-23 | Improvements in or relating to the production of compounds containing an ethylenic linkage, or a polymethine chain |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1698635A GB432628A (en) | 1933-12-23 | 1933-12-23 | Improvements in or relating to the production of compounds containing an ethylenic linkage, or a polymethine chain |
Publications (1)
Publication Number | Publication Date |
---|---|
GB432628A true GB432628A (en) | 1935-07-23 |
Family
ID=10087168
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1698635A Expired GB432628A (en) | 1933-12-23 | 1933-12-23 | Improvements in or relating to the production of compounds containing an ethylenic linkage, or a polymethine chain |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB432628A (en) |
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2487881A (en) * | 1944-03-28 | 1949-11-15 | Eastman Kodak Co | Process for preparing polymethine dyes |
US2515878A (en) * | 1946-01-19 | 1950-07-18 | Eastman Kodak Co | Arylaminomethine compounds |
WO2013066629A1 (en) * | 2011-10-19 | 2013-05-10 | Bioformix, Llc | Methylene beta-ketoester monomers, methods for making methylene beta-ketoester monomers, polymerizable compositions and products formed therefrom |
US9181365B2 (en) | 2012-03-30 | 2015-11-10 | Sirrus, Inc. | Methods for activating polymerizable compositions, polymerizable systems, and products formed thereby |
US9217098B1 (en) | 2015-06-01 | 2015-12-22 | Sirrus, Inc. | Electroinitiated polymerization of compositions having a 1,1-disubstituted alkene compound |
US9234107B2 (en) | 2012-03-30 | 2016-01-12 | Sirrus, Inc. | Ink coating formulations and polymerizable systems for producing the same |
US9249265B1 (en) | 2014-09-08 | 2016-02-02 | Sirrus, Inc. | Emulsion polymers including one or more 1,1-disubstituted alkene compounds, emulsion methods, and polymer compositions |
US9279022B1 (en) | 2014-09-08 | 2016-03-08 | Sirrus, Inc. | Solution polymers including one or more 1,1-disubstituted alkene compounds, solution polymerization methods, and polymer compositions |
US9315597B2 (en) | 2014-09-08 | 2016-04-19 | Sirrus, Inc. | Compositions containing 1,1-disubstituted alkene compounds for preparing polymers having enhanced glass transition temperatures |
US9334430B1 (en) | 2015-05-29 | 2016-05-10 | Sirrus, Inc. | Encapsulated polymerization initiators, polymerization systems and methods using the same |
US9416091B1 (en) | 2015-02-04 | 2016-08-16 | Sirrus, Inc. | Catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
US9518001B1 (en) | 2016-05-13 | 2016-12-13 | Sirrus, Inc. | High purity 1,1-dicarbonyl substituted-1-alkenes and methods for their preparation |
US9522381B2 (en) | 2013-01-11 | 2016-12-20 | Sirrus, Inc. | Method to obtain methylene malonate via bis(hydroxymethyl) malonate pathway |
US9567475B1 (en) | 2016-06-03 | 2017-02-14 | Sirrus, Inc. | Coatings containing polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
US9617377B1 (en) | 2016-06-03 | 2017-04-11 | Sirrus, Inc. | Polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
US9752059B2 (en) | 2012-11-16 | 2017-09-05 | Sirrus, Inc. | Plastics bonding systems and methods |
US9828324B2 (en) | 2010-10-20 | 2017-11-28 | Sirrus, Inc. | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom |
US10047192B2 (en) | 2012-06-01 | 2018-08-14 | Sirrus, Inc. | Optical material and articles formed therefrom |
US10196481B2 (en) | 2016-06-03 | 2019-02-05 | Sirrus, Inc. | Polymer and other compounds functionalized with terminal 1,1-disubstituted alkene monomer(s) and methods thereof |
US10414839B2 (en) | 2010-10-20 | 2019-09-17 | Sirrus, Inc. | Polymers including a methylene beta-ketoester and products formed therefrom |
US10428177B2 (en) | 2016-06-03 | 2019-10-01 | Sirrus, Inc. | Water absorbing or water soluble polymers, intermediate compounds, and methods thereof |
US10501400B2 (en) | 2015-02-04 | 2019-12-10 | Sirrus, Inc. | Heterogeneous catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
US10607910B2 (en) | 2012-11-30 | 2020-03-31 | Sirrus, Inc. | Composite compositions for electronics applications |
US10913875B2 (en) | 2012-03-30 | 2021-02-09 | Sirrus, Inc. | Composite and laminate articles and polymerizable systems for producing the same |
-
1933
- 1933-12-23 GB GB1698635A patent/GB432628A/en not_active Expired
Cited By (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2487881A (en) * | 1944-03-28 | 1949-11-15 | Eastman Kodak Co | Process for preparing polymethine dyes |
US2515878A (en) * | 1946-01-19 | 1950-07-18 | Eastman Kodak Co | Arylaminomethine compounds |
US10414839B2 (en) | 2010-10-20 | 2019-09-17 | Sirrus, Inc. | Polymers including a methylene beta-ketoester and products formed therefrom |
US9828324B2 (en) | 2010-10-20 | 2017-11-28 | Sirrus, Inc. | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom |
US9512058B2 (en) | 2011-10-19 | 2016-12-06 | Sirrus Inc. | Multifunctional monomers, methods for making multifunctional monomers, polymerizable compostions and products formed thereform |
US9221739B2 (en) | 2011-10-19 | 2015-12-29 | Sirrus, Inc. | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom |
US10611861B2 (en) | 2011-10-19 | 2020-04-07 | Sirrus, Inc. | Multifunctional monomers, methods for making multifunctional monomers, polymerizable compositions and products formed thereform |
US10604601B2 (en) | 2011-10-19 | 2020-03-31 | Sirrus, Inc. | Multifunctional monomers, methods for making multifunctional monomers, polymerizable compositions and products formed therefrom |
US9969822B2 (en) | 2011-10-19 | 2018-05-15 | Sirrus, Inc. | Multifunctional monomers, methods for making multifunctional monomers, polymerizable compositions and products formed therefrom |
US9527795B2 (en) | 2011-10-19 | 2016-12-27 | Sirrus, Inc. | Methylene beta-ketoester monomers, methods for making methylene beta-ketoester monomers, polymerizable compositions and products formed therefrom |
WO2013066629A1 (en) * | 2011-10-19 | 2013-05-10 | Bioformix, Llc | Methylene beta-ketoester monomers, methods for making methylene beta-ketoester monomers, polymerizable compositions and products formed therefrom |
US9234107B2 (en) | 2012-03-30 | 2016-01-12 | Sirrus, Inc. | Ink coating formulations and polymerizable systems for producing the same |
US10913875B2 (en) | 2012-03-30 | 2021-02-09 | Sirrus, Inc. | Composite and laminate articles and polymerizable systems for producing the same |
US9181365B2 (en) | 2012-03-30 | 2015-11-10 | Sirrus, Inc. | Methods for activating polymerizable compositions, polymerizable systems, and products formed thereby |
US9523008B2 (en) | 2012-03-30 | 2016-12-20 | Sirrus, Inc. | Ink coating formulations and polymerizable systems for producing the same |
US10047192B2 (en) | 2012-06-01 | 2018-08-14 | Sirrus, Inc. | Optical material and articles formed therefrom |
US9752059B2 (en) | 2012-11-16 | 2017-09-05 | Sirrus, Inc. | Plastics bonding systems and methods |
US10607910B2 (en) | 2012-11-30 | 2020-03-31 | Sirrus, Inc. | Composite compositions for electronics applications |
US9522381B2 (en) | 2013-01-11 | 2016-12-20 | Sirrus, Inc. | Method to obtain methylene malonate via bis(hydroxymethyl) malonate pathway |
US10086355B2 (en) | 2013-01-11 | 2018-10-02 | Sirrus, Inc. | Method to obtain methylene malonate via bis(hydroxymethyl) malonate pathway |
US10081685B2 (en) | 2014-09-08 | 2018-09-25 | Sirrus, Inc. | Emulson polymers including one or more 1,1-disubstituted alkene compounds, emulson methods, and polymer compositions |
US10633566B2 (en) | 2014-09-08 | 2020-04-28 | Sirrus, Inc. | Polymers containing a 1,1-disubstituted alkene compound |
US9249265B1 (en) | 2014-09-08 | 2016-02-02 | Sirrus, Inc. | Emulsion polymers including one or more 1,1-disubstituted alkene compounds, emulsion methods, and polymer compositions |
US9279022B1 (en) | 2014-09-08 | 2016-03-08 | Sirrus, Inc. | Solution polymers including one or more 1,1-disubstituted alkene compounds, solution polymerization methods, and polymer compositions |
US10519257B2 (en) | 2014-09-08 | 2019-12-31 | Sirrus, Inc. | Compositions containing 1,1-di-carbonyl-substituted alkene compounds for preparing polymers having enhanced glass transition temperatures |
US9637564B2 (en) | 2014-09-08 | 2017-05-02 | Sirrus, Inc. | Emulsion polymers including one or more 1,1-disubstituted alkene compounds, emulsion methods, and polymer compositions |
US9315597B2 (en) | 2014-09-08 | 2016-04-19 | Sirrus, Inc. | Compositions containing 1,1-disubstituted alkene compounds for preparing polymers having enhanced glass transition temperatures |
US10308802B2 (en) | 2014-09-08 | 2019-06-04 | Sirrus, Inc. | Polymers including one or more 1,1-disubstituted alkene compounds and polymer compositions thereof |
US9890227B1 (en) | 2014-09-08 | 2018-02-13 | Sirrus, Inc. | Compositions containing 1,1-di-substituted alkene compounds for preparing polymers having enhanced glass transition temperatures |
US10184073B2 (en) | 2014-09-08 | 2019-01-22 | Sirrus, Inc. | Emulsion including polymers containing a 1,1-disubstituted alkene compound, adhesives, coatings, and methods thereof |
US9969819B2 (en) | 2014-09-08 | 2018-05-15 | Sirrus, Inc. | Pressure sensitive adhesive including a 1,1-disubstituted alkene compound |
US10167348B2 (en) | 2014-09-08 | 2019-01-01 | Sirrus, Inc. | Solution polymers formed from methylene malonate monomers, polymerization, and solution polymer products |
US9790295B2 (en) | 2014-09-08 | 2017-10-17 | Sirrus, Inc. | Compositions containing 1,1-disubstituted alkene compounds for preparing polymers having enhanced glass transition temperatures |
US9676875B2 (en) | 2014-09-08 | 2017-06-13 | Sirrus, Inc. | Solution polymers including one or more 1,1-disubstituted alkene compounds, solution polymerization methods, and polymer compositions |
US11021617B2 (en) | 2014-09-08 | 2021-06-01 | Sirrus, Inc. | Polymers including one or more 1,1-disubstituted alkene compounds and polymer compositions thereof |
US9416091B1 (en) | 2015-02-04 | 2016-08-16 | Sirrus, Inc. | Catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
US9938223B2 (en) | 2015-02-04 | 2018-04-10 | Sirrus, Inc. | Catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
US10501400B2 (en) | 2015-02-04 | 2019-12-10 | Sirrus, Inc. | Heterogeneous catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
US9334430B1 (en) | 2015-05-29 | 2016-05-10 | Sirrus, Inc. | Encapsulated polymerization initiators, polymerization systems and methods using the same |
US9683147B2 (en) | 2015-05-29 | 2017-06-20 | Sirrus, Inc. | Encapsulated polymerization initiators, polymerization systems and methods using the same |
US10087272B2 (en) | 2015-05-29 | 2018-10-02 | Sirrus, Inc. | Encapsulated polymerization initiators, polymerization systems and methods using the same |
US9617354B2 (en) | 2015-06-01 | 2017-04-11 | Sirrus, Inc. | Electroinitiated polymerization of compositions having a 1,1-disubstituted alkene compound |
US9217098B1 (en) | 2015-06-01 | 2015-12-22 | Sirrus, Inc. | Electroinitiated polymerization of compositions having a 1,1-disubstituted alkene compound |
US9518001B1 (en) | 2016-05-13 | 2016-12-13 | Sirrus, Inc. | High purity 1,1-dicarbonyl substituted-1-alkenes and methods for their preparation |
US10428177B2 (en) | 2016-06-03 | 2019-10-01 | Sirrus, Inc. | Water absorbing or water soluble polymers, intermediate compounds, and methods thereof |
US9567475B1 (en) | 2016-06-03 | 2017-02-14 | Sirrus, Inc. | Coatings containing polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
US10150886B2 (en) | 2016-06-03 | 2018-12-11 | Sirrus, Inc. | Coatings containing polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
US9745413B1 (en) | 2016-06-03 | 2017-08-29 | Sirrus, Inc. | Polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
US9617377B1 (en) | 2016-06-03 | 2017-04-11 | Sirrus, Inc. | Polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
US9718989B1 (en) | 2016-06-03 | 2017-08-01 | Sirrus, Inc. | Coatings containing polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
US10087283B2 (en) | 2016-06-03 | 2018-10-02 | Sirrus, Inc. | Polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
US10196481B2 (en) | 2016-06-03 | 2019-02-05 | Sirrus, Inc. | Polymer and other compounds functionalized with terminal 1,1-disubstituted alkene monomer(s) and methods thereof |
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