GB390808A - Improvements in or relating to the manufacture of dyes - Google Patents
Improvements in or relating to the manufacture of dyesInfo
- Publication number
- GB390808A GB390808A GB2779231A GB2779231A GB390808A GB 390808 A GB390808 A GB 390808A GB 2779231 A GB2779231 A GB 2779231A GB 2779231 A GB2779231 A GB 2779231A GB 390808 A GB390808 A GB 390808A
- Authority
- GB
- United Kingdom
- Prior art keywords
- propargylaldehydediethylacetal
- ethiodide
- condensed
- methyl
- prepared
- 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
- 239000000975 dye Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- RGUXEWWHSQGVRZ-UHFFFAOYSA-N 3,3-diethoxyprop-1-yne Chemical compound CCOC(C#C)OCC RGUXEWWHSQGVRZ-UHFFFAOYSA-N 0.000 abstract 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract 4
- SJLJHVITDDTVMW-UHFFFAOYSA-N C[S+]1C2=CC=CC=C2N=C1 Chemical compound C[S+]1C2=CC=CC=C2N=C1 SJLJHVITDDTVMW-UHFFFAOYSA-N 0.000 abstract 3
- 230000001476 alcoholic effect Effects 0.000 abstract 3
- 229940072033 potash Drugs 0.000 abstract 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 3
- 235000015320 potassium carbonate Nutrition 0.000 abstract 3
- FKKVKKSEVMQYER-UHFFFAOYSA-N 1,1-diethoxybut-2-yne Chemical compound CCOC(OCC)C#CC FKKVKKSEVMQYER-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical group 0.000 abstract 2
- 238000010792 warming Methods 0.000 abstract 2
- OEVSHJVOKFWBJY-UHFFFAOYSA-M 1-ethyl-2-methylquinolin-1-ium;iodide Chemical compound [I-].C1=CC=C2[N+](CC)=C(C)C=CC2=C1 OEVSHJVOKFWBJY-UHFFFAOYSA-M 0.000 abstract 1
- SNHUPGJQDQJZKL-UHFFFAOYSA-N 1-methyl-1lambda4,3-benzoselenazole Chemical compound C[SeH]1C=NC2=C1C=CC=C2 SNHUPGJQDQJZKL-UHFFFAOYSA-N 0.000 abstract 1
- ZMDDOWQHSDJXDW-UHFFFAOYSA-N 2,3-dibromopropanal Chemical compound BrCC(Br)C=O ZMDDOWQHSDJXDW-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000012259 ether extract Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- IJNJLGFTSIAHEA-UHFFFAOYSA-N prop-2-ynal Chemical compound O=CC#C IJNJLGFTSIAHEA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
- -1 silver halide Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Dicarbocyanine dyestuffs are obtained by condensing an acetal of propargyl aldehyde, or of a b alkyl or aryl derivative thereof, with a quaternary salt of a heterocyclic nitrogenous base having an active a methyl group. In examples: (1) 1-methylbenzthiazol ethiodide or the corresponding oxazole is condensed with crude propargylaldehydediethylacetal in the presence of pyridine: (2) 1-methylbenzthiazol ethiodide is similarly condensed with pure propargylaldehydediethylacetal: (3) quinaldine ethiodide is condensed in diacetone alcohol with pure propargylaldehydediethylacetal: (4) 1-methyl-a -naphthothiazol ethiodide is condensed in pyridine with crude propargylaldehydediethylacetal: (5) 1-methyl benzselenazol ethiodide is condensed in diacetone alcohol with pure propargylaldehydediethylacetal. The following dyestuffs are also prepared: 2 : 2<1>-diethyl-3 : 4 : 3<1> : 4<1>-dibenzthiodicarbocyanine (from 2 - methyl - b - naphthothiazol ethiodide and propargylaldehydediethylacetal) and 2 : 2<1>-diethyl-8-methylthiodicarbocyanineiodide (from 1-methylbenzthiazole ethiodide and tetrolaldehydediethylacetal). 2-Methyl-b -naphthoxazole and 2 : 3 : 3-trimethyl indolenine, the quaternary salts of which may be used, are mentioned. The dyestuffs are photographic sensitizers for silver halide emulsions. Propargylaldehydediethylacetal is prepared from acroleindibromide by heating with excess of alcoholic potash, filtering off the potassium bromide, and extracting with ether after distilling off the alcohol and adding water. The crude diethylacetal obtained by fractionating the ether extract is found to give greater yields of dyestuff than the pure product which may be obtained by allowing the crude product to stand over solid caustic potash and refractionating. b -Phenylpropargylaldehydediethylacetal may be prepared from monobromcinnamic aldehyde diethylacetal by warming with alcoholic potash. Tetrolaldehydediethylacetal may be prepared from dibromcrotonicaldehyde diethylacetal by warming with alcoholic potash under reduced pressure and fractionating.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2779231A GB390808A (en) | 1931-10-06 | 1931-10-06 | Improvements in or relating to the manufacture of dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2779231A GB390808A (en) | 1931-10-06 | 1931-10-06 | Improvements in or relating to the manufacture of dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB390808A true GB390808A (en) | 1933-04-06 |
Family
ID=10265376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2779231A Expired GB390808A (en) | 1931-10-06 | 1931-10-06 | Improvements in or relating to the manufacture of dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB390808A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999019558A2 (en) * | 1997-10-14 | 1999-04-22 | Henkel Kommanditgesellschaft Auf Aktien | Use of malonaldehyde derivatives for dyeing fibres containing keratin |
-
1931
- 1931-10-06 GB GB2779231A patent/GB390808A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999019558A2 (en) * | 1997-10-14 | 1999-04-22 | Henkel Kommanditgesellschaft Auf Aktien | Use of malonaldehyde derivatives for dyeing fibres containing keratin |
| WO1999019558A3 (en) * | 1997-10-14 | 1999-06-17 | Henkel Kgaa | Use of malonaldehyde derivatives for dyeing fibres containing keratin |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB458405A (en) | Process for the manufacture of polymethine dyestuffs | |
| GB390808A (en) | Improvements in or relating to the manufacture of dyes | |
| US2571775A (en) | Pyrro-colinocarbocyanine dyes and process for the preparation thereof | |
| US2647053A (en) | Photographic emulsions containing symmetrical carbocyanine dyes | |
| US2106383A (en) | Manufacture of carbocyanine dyes | |
| US2104855A (en) | Polymethine dyes | |
| GB479926A (en) | Manufacture of dyes and process for sensitising photographic silver halide emulsions | |
| US2060382A (en) | Trimethine-cyanine dyes | |
| Hamer | 149. Bases of which methincyanines are the quaternary salts | |
| GB385320A (en) | Manufacture of cyanine dyes and the application thereof in photography | |
| GB549203A (en) | Improvements in or relating to dyestuffs | |
| GB402458A (en) | Improvements in photographic sensitisers | |
| US2270255A (en) | Selenotricarbocyanine dyes | |
| GB383486A (en) | Improvements in light-sensitive silver halide emulsions | |
| US2071994A (en) | Thiazole trimethine cyanines | |
| US1957869A (en) | Selenazolinocarbocyanine dye and process of preparing it | |
| US2071993A (en) | Trimethine cyanine dyes | |
| GB457450A (en) | Manufacture of dyes and process for sensitising photographic silver halide emulsions | |
| GB464852A (en) | An improved method of sensitizing photographic silver halide emulsions | |
| GB490729A (en) | Manufacture of dyes and process for sensitising photographic silver halide emulsions | |
| Hamer | CXCIV.—Neocyanine | |
| SU369132A1 (en) | 'Ska! L \. Cl. from 09L 23 / 08UDK 547.712'8'32 (088.8) B. S. Portna and G. N. Kamenska Institute of Chemical and Photographic Industry | |
| US2984663A (en) | Methin dyes containing hydroxypyrroline nuclei | |
| SU51779A1 (en) | The method of obtaining beta-alkyl and beta-aryl substituted acetylacetic acid phenylamides | |
| GB415949A (en) | Process for sensitising photographic silver halide emulsions |