GB749192A - Improvements in or relating to polynuclear cyanine dyes - Google Patents
Improvements in or relating to polynuclear cyanine dyesInfo
- Publication number
- GB749192A GB749192A GB1256453A GB1256453A GB749192A GB 749192 A GB749192 A GB 749192A GB 1256453 A GB1256453 A GB 1256453A GB 1256453 A GB1256453 A GB 1256453A GB 749192 A GB749192 A GB 749192A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formula
- complete
- groups
- nuclei
- 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 4
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- -1 1:3:4-thiadiazole Chemical class 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000002837 carbocyclic group 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
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-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
- 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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 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
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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 class C1=CC2=CC=CN=C2C2=C1C1=CC=CC=C1C=C2 OZIRORHUKSXTLG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000002916 oxazoles Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 abstract 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 150000003557 thiazoles Chemical class 0.000 abstract 1
- 150000003549 thiazolines Chemical class 0.000 abstract 1
- 125000004001 thioalkyl group Chemical group 0.000 abstract 1
- 150000003852 triazoles 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
- C09B23/10—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
Dyes having one of the general formulae:-<FORM:0749192/IV(c)/1> <FORM:0749192/IV(c)/2> wherein R1 and R2 are alkyl or aralkyl groups or together complete a carbocyclic ring such as cyclopentamethylene, R5 is an alkyl group, R6 is H or an alkykl group, R7 and R8 are alkyl groups, Y is an anion, m, n and p are O or I and D1, D2 and D3 complete heterocyclic nitrogen nuclei, are prepared by reacting the dyes of Specification 749,189 which have a reactive thioalkyl group on the 4 position of the iminazolenine ring with a compound of formula:- <FORM:0749192/IV(c)/3> where Z is an anion, or with a compound of formula:- <FORM:0749192/IV(c)/4> D1, and D2 may complete nuclei such as thiazoles, oxazoles, or selenazoles and their benzene or naphthalene homologues, pyridine, quinoline, naphthoquinolines, indolenines, pyrimodines, quinazolines, 1:3:4-thiadiazole, thiazolines and selenazolines, or, when n is O, iminazolenines. The carbocyclic rings of such nuclei may be substituted with alkyl, aryl, alkoxy or methylene dioxy groups or by halogen atoms. D3 may complete a rhodanine, oxarhodanine, oxindole, 5-pyrazolone, hydantoin, thio-hydantoin, pseudohydantoin, pseudothiohydantoin, oxazolone or thiazolidone (including 21:11 - benziminazo - 2:3 - thiazold - 4 - one) nucleus. Specifications 734,793, 749,190 and 749,193 also are referred to. In the Provisional Specification, R1, R2 and R6 are defined as hydrocarbon groups, R7 and R8 (R9 and R10 in formulae in Provisional Specification) are defined also as arakyl and aryl groups and substituted alkyl groups are referred to in connection with R5 and R7 (R9) and R8 (R10). D1 and D2 may also complete acenaphthene or anthracene homologues of the thiazole, oxazole or selenazole series or nuclei of the oxazoline, pyrazolenine or triazole series. Reference is also made to reacting dyes of the formula:- <FORM:0749192/IV(c)/5> where R9 is alkyl, aralkyl or aryl, p is 1 or 3, D2 has the same significance as D3 above and the other symbols have the meanings given above, with a compound of formula IV or V above. The methine chain in formula VI and VIII above may also carry alkyl substituents in addition to R6.
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 |
|---|---|
| GB749192A true GB749192A (en) | 1956-05-23 |
Family
ID=10006942
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1256553A Expired GB749193A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to polynuclear methine dyes |
| GB1256353A Expired GB749190A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to dinuclear cyanine and merocyanine dyes |
| GB1256253A Expired GB749189A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to dinuclear cyanine dyes |
| GB1256453A Expired GB749192A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to polynuclear cyanine dyes |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1256553A Expired GB749193A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to polynuclear methine dyes |
| GB1256353A Expired GB749190A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to dinuclear cyanine and merocyanine dyes |
| GB1256253A Expired GB749189A (en) | 1953-05-06 | 1953-05-06 | Improvements in or relating to dinuclear cyanine dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (4) | GB749193A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1058303A (en) * | 1964-03-04 | 1967-02-08 | Gevaert Photo Prod Nv | Methine dyes |
-
1953
- 1953-05-06 GB GB1256553A patent/GB749193A/en not_active Expired
- 1953-05-06 GB GB1256353A patent/GB749190A/en not_active Expired
- 1953-05-06 GB GB1256253A patent/GB749189A/en not_active Expired
- 1953-05-06 GB GB1256453A patent/GB749192A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB749190A (en) | 1956-05-23 |
| GB749193A (en) | 1956-05-23 |
| GB749189A (en) | 1956-05-23 |
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