GB354826A - Improvements in or relating to the manufacture of dyes - Google Patents
Improvements in or relating to the manufacture of dyesInfo
- Publication number
- GB354826A GB354826A GB1503730A GB1503730A GB354826A GB 354826 A GB354826 A GB 354826A GB 1503730 A GB1503730 A GB 1503730A GB 1503730 A GB1503730 A GB 1503730A GB 354826 A GB354826 A GB 354826A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- primary
- prepared
- substituted
- glutaconic
- 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 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- 150000001299 aldehydes Chemical class 0.000 abstract 3
- 239000007859 condensation product Substances 0.000 abstract 3
- MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical compound C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 150000003839 salts Chemical group 0.000 abstract 2
- 150000003336 secondary aromatic amines Chemical class 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
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- YDQJXVYGARVLRT-UHFFFAOYSA-N Lepidine Natural products C=1C=CC(CC=2NC=CN=2)=CC=1OC=1C(OC)=CC=CC=1CC1=NC=CN1 YDQJXVYGARVLRT-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- VUCMMJBDNXZQDJ-ZUJIUJENSA-N hydron;n-[(1e,3e)-5-phenyliminopenta-1,3-dienyl]aniline;chloride Chemical compound Cl.C=1C=CC=CC=1N\C=C\C=C\C=NC1=CC=CC=C1 VUCMMJBDNXZQDJ-ZUJIUJENSA-N 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 125000003263 primary aromatic amine group Chemical group 0.000 abstract 1
- 150000003142 primary aromatic amines Chemical class 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 150000004992 toluidines Chemical class 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
- C09B23/086—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 more than five >CH- groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Polymethine dyestuffs, which are photographic sensitizers, are prepared by treating a quaternary salt of a heterocyclic nitrogenous base having an active a methyl group, with a condensation product of glutaconic aldehyde with a primary or secondary aromatic amine. In an example, glutaconicaldehydedianilidehydrochloride is boiled with quinaldine ethiodide in dry spirit solution, and a solution of sodium in dry spirit added, when the dyestuff separates. 1-Methylbenzthiazole, 1-methyl-a -naphthiazole and 2-methyl-b -naphthathiazole and substituted derivatives thereof are mentioned as suitable heterocyclic bases. The condensation products of glutaconic aldehyde with primary and secondary aromatic amines are prepared by heating in spirit solution a pyridinium salt, e.g. 2 : 4-dinitrophenylpyridiniumchloride with the aromatic amine, e.g. aniline, toluidine, a naphthylamine or methylaniline. Specification 351,555 is referred to. According to the Provisional Specification quaternary salts of heterocyclic nitrogenous bases having active methyl groups in the g position, and also condensation products of substituted glutaconic aldehydes with any primary or secondary amine or ammonia, may be employed in the production of similar polymethine dyestuffs. The following additional components are specified : lepidine, 1-methyl benzoxazole, a and g picolines, substituted 2-methylindolenines, e.g. 2 : 3 : 3-trimethylindolenine and hydroxyglutaconicaldehydedianilidehydrobromide, The latter is prepared by the reaction of aniline, furfuraldehyde and hydrobromic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1503730A GB354826A (en) | 1930-05-15 | 1930-05-15 | Improvements in or relating to the manufacture of dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1503730A GB354826A (en) | 1930-05-15 | 1930-05-15 | Improvements in or relating to the manufacture of dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB354826A true GB354826A (en) | 1931-08-17 |
Family
ID=10051928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1503730A Expired GB354826A (en) | 1930-05-15 | 1930-05-15 | Improvements in or relating to the manufacture of dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB354826A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4681827A (en) * | 1985-04-17 | 1987-07-21 | Hoechst Aktiengesellschaft | Organic electrophotographic material sensitized by cyanine dye |
-
1930
- 1930-05-15 GB GB1503730A patent/GB354826A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4681827A (en) * | 1985-04-17 | 1987-07-21 | Hoechst Aktiengesellschaft | Organic electrophotographic material sensitized by cyanine dye |
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