GB730489A - Improvements in or relating to cyanine and merocyanine dyes - Google Patents
Improvements in or relating to cyanine and merocyanine dyesInfo
- Publication number
- GB730489A GB730489A GB2877252A GB2877252A GB730489A GB 730489 A GB730489 A GB 730489A GB 2877252 A GB2877252 A GB 2877252A GB 2877252 A GB2877252 A GB 2877252A GB 730489 A GB730489 A GB 730489A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkyl
- compound
- nucleus
- 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 5
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 title 1
- 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 8
- 150000001875 compounds Chemical class 0.000 abstract 5
- 150000003839 salts Chemical group 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- -1 heterocyclic keto-methylene compound Chemical class 0.000 abstract 3
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical compound C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 abstract 2
- MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical compound C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-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
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000000623 heterocyclic 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-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
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical group CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-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
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 150000004891 diazines Chemical class 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 238000010438 heat treatment Methods 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
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 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
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
- 238000010992 reflux Methods 0.000 abstract 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 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
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Dyes of the following general formula are described:- I <FORM:0730489/IV (c)/1> and II <FORM:0730489/IV (c)/2> wherein R1, R2, R3 and R4 are alkyl groups containing up to 4 carbon atoms, R5 is an alkyl group, R6 is a hydrocarbon radical or is joined via carbon and nitrogen to the nucleus D2 to form a heterocyclic nucleus, R7 is H or alkyl, X is an anion, m and n are 0 or 1 and D1 and D2 complete heterocyclic nuclei. The dyes of formula I may be prepared by reacting a compound of formula <FORM:0730489/IV (c)/3> wherein Y is an acid radical with a compound of formula <FORM:0730489/IV (c)/4> wherein Q is a thioether or acetanilide group. The dyes of formula II may be prepared by reacting a compound of formula III with a heterocyclic keto-methylene compound in the presence of an alkyl orthoformate or alkyl ortho acetate. Symmetrical dyes of formula I are obtained by reacting two mols. of a compound of formula III with an alkyl orthoformate. In place of the quaternary salt of formula III there may be used a compound of formula <FORM:0730489/IV (c)/5> and two molecular equivalents of a salt R4Y (in which case R3 = R4) and instead of the quaternary salt of formula IV the corresponding base may be used together with a quaternizing salt R5X. D1 may complete a nucleus such as thiazole or oxazole and their benzene and naphthalene homologues, quinoline, indolenine, diazines such as pyrimidine, diazoles such as thio-b ,b 1-diazole, pyrazolenine and iminazolenine. The carbocyclic rings of such nuclei may be substituted with alkyl, aryl, alkoxy, methylene dioxy or halogen radicals. D2 may complete a rhodanine, pyrazole-5-one, thiohydantoin or thiazolidene (e.g. with R6, a benziminazothiazolidone) nucleus. According to the Provisional Specification the nucleus D1 may also be selenazole, an acenaphthene or anthracene homologue of thiazole, oxazole or selenazole, pyridine, a - and b -naphthoquinolines, lepidine, quinazoline, oxazoline, thiazoline, or selenazotine, and D2 may be oxarhodanine or an N-hydrocarbon derivative thereof, oxindole, hydantoin, pseudohydantoin or pseudothiohydantoin. Further, formula II is given wherein the two nuclei are joined by = (CH-CH)p, where p is a positive integer, e.g. 1 or 2. It is stated that the carbocyclic rings of the nuclei D1 may also be substituted with amino or hydroxy groups, that Q in formula IV may be an amino or substituted amino group, and that R1, R2 and R3 may be hydrocarbon groups, R4 may be alkyl or aralkyl and R5 may also be aralkyl, hydroxyalkyl or carboxyalkyl.ALSO:4 : 4 : 5 - trimethyl - 3 - pyrazolone is prepared by heating ethyl a ,a -dimethylacetoacetate and hydrazine hydrate under reflux, and removing the ethanol and water formed. 4 : 4 : 5 - trimethylpyrazolenine - 3 - thiol is prepared by adding phosphorus pentasulphide to 4 : 4 : 5-trimethyl-3-pyrazolone in dry xylene. 3 - Methylthio - 4 : 4 : 5 - trimethylpyrazolene is prepared by adding dimethyl sulphate to 4 : 4 : 4 : 5 - trimethylpyrazolenine - 3 - thiol dissolved in sodium hydroxide. Similarly, ethyl a : a - diethylacetoacetate yields 4 : 4 - diethyl - 5 - methyl - 3 - pyrazolone and the corresponding -3-thiol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2877252A GB730489A (en) | 1952-11-14 | 1952-11-14 | Improvements in or relating to cyanine and merocyanine dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2877252A GB730489A (en) | 1952-11-14 | 1952-11-14 | Improvements in or relating to cyanine and merocyanine dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB730489A true GB730489A (en) | 1955-05-25 |
Family
ID=10280906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2877252A Expired GB730489A (en) | 1952-11-14 | 1952-11-14 | Improvements in or relating to cyanine and merocyanine dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB730489A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007114398A1 (en) * | 2006-03-31 | 2007-10-11 | Wako Pure Chemical Industries, Ltd. | Pyrazole-type cyanine dye |
-
1952
- 1952-11-14 GB GB2877252A patent/GB730489A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007114398A1 (en) * | 2006-03-31 | 2007-10-11 | Wako Pure Chemical Industries, Ltd. | Pyrazole-type cyanine dye |
| US8921124B2 (en) | 2006-03-31 | 2014-12-30 | Wako Pure Chemical Industries, Ltd. | Pyrazole-based cyanine dye |
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