GB369236A - Improvements in or relating to the manufacture of dyes - Google Patents
Improvements in or relating to the manufacture of dyesInfo
- Publication number
- GB369236A GB369236A GB3798130A GB3798130A GB369236A GB 369236 A GB369236 A GB 369236A GB 3798130 A GB3798130 A GB 3798130A GB 3798130 A GB3798130 A GB 3798130A GB 369236 A GB369236 A GB 369236A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- ethiodide
- anhydride
- condensed
- molecule
- 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 15
- 150000003839 salts Chemical group 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- 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 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 150000008065 acid anhydrides Chemical class 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 239000000126 substance Substances 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
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000004280 Sodium formate Substances 0.000 abstract 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000000298 carbocyanine Substances 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical group [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 abstract 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 abstract 1
- 235000019254 sodium formate Nutrition 0.000 abstract 1
- 229960004025 sodium salicylate Drugs 0.000 abstract 1
- 125000001424 substituent group Chemical group 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
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
-
- 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
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Carbocyanine dyes, having a substituent in the carbocyanine chain are produced by treating two molecular proportions of a quaternary salt of a heterocyclic nitrogenous base having an active a -methyl group with at least two molecular proportions of an organic carboxylic acid anhydride, in the presence of not more than one molecular proportion of an acid-binding substance, e.g. the salt of a weak acid. If acetic anhydride is used as the acid anhydride, an a -acetylmethyl derivative of the quaternary salt is first formed, with liberation of a molecule of acetic acid, and a second molecule of the quaternary salt then condenses with the acetyl derivative, a further molecule of acetic anhydride being used as a dehydrating agent, and the acid-binding substance removing one molecule of the hydriodic or other acid of the quaternary salt. According to examples, (1) acetic anhydride is condensed with 1-methylbenzthiazole ethiodide, 2 : 3 : 3-trimethylindolenine ethiodide, quinaldine ethiodide, 1-methylbenzoxazole ethiodide, 1-methyl-3 : 4-benzbenzthiazole ethiodide and 1-methyl-5 : 6 - benzbenzthiazole ethiode, by heating under reflux in the presence of anhydrous sodium acetate: (2) 1-methylbenzoxazole ethiodide is similarly condensed with benzoic anhydride: (3) 1-methylbenzthiazole ethiodide is condensed with acetic anhydride in the presence of sodium formate. Sodium salicylate is also mentioned as an acid-binding agent, and propionic anhydride as a suitable anhydride. Many of the products are photographic sensitizers. Specification 232,740, [Class 2 (iii), Dyes &c.], is referred to. According to the Provisional Specification, acid anhydrides may be condensed with quaternary salts of heterocyclic nitrogenous bases having either a reactive hydrogen atom or methyl group in the a or g positions. For example, benzthiazole ethiodide may be condensed with acetic anhydride. Quinoline and lepidine are also mentioned as suitable bases whose quaternary salts may be used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3798130A GB369236A (en) | 1930-12-16 | 1930-12-16 | Improvements in or relating to the manufacture of dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3798130A GB369236A (en) | 1930-12-16 | 1930-12-16 | Improvements in or relating to the manufacture of dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB369236A true GB369236A (en) | 1932-03-16 |
Family
ID=10400373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3798130A Expired GB369236A (en) | 1930-12-16 | 1930-12-16 | Improvements in or relating to the manufacture of dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB369236A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE741250C (en) * | 1933-03-06 | 1943-11-08 | Kodak Ag | Process for the preparation of oxocarbocyanine dyes substituted in the meso position |
| US2980671A (en) * | 1958-04-15 | 1961-04-18 | Gevaert Photo Prod Nv | Monomethine cyanine dyes and method for preparing them |
-
1930
- 1930-12-16 GB GB3798130A patent/GB369236A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE741250C (en) * | 1933-03-06 | 1943-11-08 | Kodak Ag | Process for the preparation of oxocarbocyanine dyes substituted in the meso position |
| US2980671A (en) * | 1958-04-15 | 1961-04-18 | Gevaert Photo Prod Nv | Monomethine cyanine dyes and method for preparing them |
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