GB749189A - Improvements in or relating to dinuclear cyanine dyes - Google Patents
Improvements in or relating to dinuclear cyanine dyesInfo
- Publication number
- GB749189A GB749189A GB1256253A GB1256253A GB749189A GB 749189 A GB749189 A GB 749189A GB 1256253 A GB1256253 A GB 1256253A GB 1256253 A GB1256253 A GB 1256253A GB 749189 A GB749189 A GB 749189A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- alkyl
- complete
- aryl
- 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 3
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- -1 1:3:4-thiadiazole Chemical compound 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 150000001450 anions Chemical class 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 abstract 1
- VGGUVGVAVAAODK-ZROIWOOFSA-N (5z)-2-amino-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(OC2CCCC2)C(OC)=CC=C1\C=C1/SC(=N)NC1=O VGGUVGVAVAAODK-ZROIWOOFSA-N 0.000 abstract 1
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical class C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 abstract 1
- SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical compound O=C1NCCS1 SLYRGJDSFOCAAI-UHFFFAOYSA-N 0.000 abstract 1
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 abstract 1
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 abstract 1
- VYDRCHNHWXHJSQ-UHFFFAOYSA-N 3-sulfanylidene-1,2,4-oxathiazolidin-5-one Chemical compound S1C(=S)NC(=O)O1 VYDRCHNHWXHJSQ-UHFFFAOYSA-N 0.000 abstract 1
- MVVFUAACPKXXKJ-UHFFFAOYSA-N 4,5-dihydro-1,3-selenazole Chemical class C1CN=C[Se]1 MVVFUAACPKXXKJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 abstract 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 abstract 1
- 229940091173 hydantoin Drugs 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 1
- OZIRORHUKSXTLG-UHFFFAOYSA-N naphtho[1,2-h]quinoline Chemical compound C1=CC2=CC=CN=C2C2=C1C1=CC=CC=C1C=C2 OZIRORHUKSXTLG-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003568 thioethers Chemical group 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 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
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
-
- 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
- C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
-
- 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
-
- 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
-
- 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
- C09B23/102—The polymethine chain containing an even number of >CH- groups two heterocyclic rings linked carbon-to-carbon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Cyanine dyes having one of the general formulae:-<FORM:0749189/IV(c)/1> <FORM:0749189/IV(c)/2> wherein R1 and R2 are alkyl or aralkyl groups, or together complete an aliphatic carboxylic ring such as cyclopentamethylene, R3, R5 and R7 are alkyl groups, R6 is H or alkyl, D1 and D2 complete heterocyclic nitrogen rings, n and m are 0 or 1 and Y is an anion, are prepared by reacting a compound of the formula:- <FORM:0749189/IV(c)/3> wherein X is an anion with a compound of the formula.- <FORM:0749189/IV(c)/4> wherein Q is a thio ether, thio ether vinyl or acetanilidovinyl group, or with a compound of the formula:- <FORM:0749189/IV(c)/5> The reactions are preferably carried out in the presence of a base such as pyridine, triethylamine, sodium acetate or sodium ethoxide. Instead of either of the above quaternary salts, the free bases may be used together with sufficient alkyl salt (R5 or R7Y) to convert them to the corresponding quaternary salts. D1 may complete a nucleus of the thiazole, oxazole or selenazole series, including their benzene and naphthalene homologues, or of the pyridine, quinoline, naphthoquinoline, indolenine, pyrimidine, quinazoline, 1:3:4-thiadiazole, thiazoline or selenazoline series, or, when n is O, D1 may be iminazolenine (i.e. by reacting two mols of a compound of formula III together, or by using a compound as described in Specification 734,792). The carbocyclic rings of such nuclei may carry alkyl, aryl, alkoxy, methylene dioxy or halogen substituents. D2 may complete a rhodanine, oxarhodanine, oxindole, 5-pyrazolone, hydantoin, thiohydantoin, pseudohydantoin, pseudothiohydantoin, oxazolone or thiazolidone (including 21:1 - benziminazo - 2:3 -thioazolid - 4 - one) nucleus. Some of the products are identical with those described in Specification 734,792. In the Provisional Specification, R1 and R2 are defined also as aryl, R6 as hydrocarbon and R7 (9 in the Provisional formula) as aryl or aralkyl. Additional values of D1 are given and merodicarbocyanine dyes similar to formula VII are referred to. Substituents on the methine chain in formula VI, other than R6, are indicated. Compounds of formula V may also be employed by having a reactive =CHOH or =CHNAC6H5 group. Specifications 743,133, 749,191 [Group IV(b)] and 749,192 also are referred to.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1256353A GB749190A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to dinuclear cyanine and merocyanine dyes |
| GB1256453A GB749192A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to polynuclear cyanine dyes |
| GB1256553A GB749193A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to polynuclear methine dyes |
| GB1256253A GB749189A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to dinuclear cyanine dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1256253A GB749189A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to dinuclear cyanine dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB749189A true GB749189A (en) | 1956-05-23 |
Family
ID=10006942
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1256453A Expired GB749192A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to polynuclear cyanine dyes |
| GB1256253A Expired GB749189A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to dinuclear cyanine dyes |
| GB1256353A Expired GB749190A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to dinuclear cyanine and merocyanine dyes |
| GB1256553A Expired GB749193A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to polynuclear methine dyes |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1256453A Expired GB749192A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to polynuclear cyanine dyes |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1256353A Expired GB749190A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to dinuclear cyanine and merocyanine dyes |
| GB1256553A Expired GB749193A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to polynuclear methine dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (4) | GB749192A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359113A (en) * | 1964-03-04 | 1967-12-19 | Gevaert Photo Prod Nv | Silver halide emulsions sensitized with methine dyes containing an imidazole nucleus |
-
1953
- 1953-05-06 GB GB1256453A patent/GB749192A/en not_active Expired
- 1953-05-06 GB GB1256253A patent/GB749189A/en not_active Expired
- 1953-05-06 GB GB1256353A patent/GB749190A/en not_active Expired
- 1953-05-06 GB GB1256553A patent/GB749193A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359113A (en) * | 1964-03-04 | 1967-12-19 | Gevaert Photo Prod Nv | Silver halide emulsions sensitized with methine dyes containing an imidazole nucleus |
Also Published As
| Publication number | Publication date |
|---|---|
| GB749193A (en) | 1956-05-23 |
| GB749192A (en) | 1956-05-23 |
| GB749190A (en) | 1956-05-23 |
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