GB1123094A - A process for the production of substituted 2,7-bis(phenylazc) derivatives of chromotropic acid - Google Patents
A process for the production of substituted 2,7-bis(phenylazc) derivatives of chromotropic acidInfo
- Publication number
- GB1123094A GB1123094A GB1448066A GB1448066A GB1123094A GB 1123094 A GB1123094 A GB 1123094A GB 1448066 A GB1448066 A GB 1448066A GB 1448066 A GB1448066 A GB 1448066A GB 1123094 A GB1123094 A GB 1123094A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- coupling
- chromotropic acid
- chromotropic
- bis
- 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
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical class OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 title abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 238000005859 coupling reaction Methods 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 229910006069 SO3H Inorganic materials 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 150000007530 organic bases Chemical class 0.000 abstract 2
- 238000001556 precipitation Methods 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- XLNJLYSLXXLENR-UHFFFAOYSA-N N[As]C1=CC=CC=C1 Chemical compound N[As]C1=CC=CC=C1 XLNJLYSLXXLENR-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 229910052790 beryllium Inorganic materials 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910001424 calcium ion Inorganic materials 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 229910052712 strontium Inorganic materials 0.000 abstract 1
- -1 sulphate anion Chemical class 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/04—Disazo dyes in which the coupling component is a dihydroxy or polyhydroxy compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Substituted 2,7-bis-phenylazo derivatives of chromotropic acid of general formula <FORM:1123094/C4-C5/1> in which Y is an -OH, -SH, -COOH, -SO3H, -SeO2H, or -CH2N(CH2COOH)2 group, R1 and R2 which may be the same or different are H, -COOH, -SO3H, -NO2, -NHCOCH3, -N(CH3)2-N(C2H5)2 -CH3, -Cl, -Br or -F are prepared by coupling diazonium salts of formula R1R2YC6H2N2A in which A is a chloride or sulphate anion, R1R2 and Y being as above, with chromotropic acid whilst stirring at a temperature below 0 DEG C. in aqueous alkali medium at pH 10-14 in the presence of organic bases and ions of the alkali earth metals Be, Mg, Ca and Sr to form the bisazo compounds which are purified by precipitation with HCl to remove the metal ions. The organic base used may be pyridine, quinoline, trimethylamine or tetramethylammonium hydroxide used in a ratio of 1:1 to 1:5 to water. The course of the coupling reaction may be monitored by adding a sample of the coupling reaction mixture to conc. sulphuric acid when the bisazo dye is indicated by a green colour and the mono-azo dye is indicated by a blue colour.ALSO:In Examples 6, 7 and 10 the bisazo compounds of formulae <FORM:1123094/C2/1> <FORM:1123094/C2/2> <FORM:1123094/C2/3> are prepared by coupling the diazotized aminophenyl-arsenic or -stibenic acid with chromotropic acid in water and pyridine mixture in presence of calcium ions, this being followed by precipitation with concentrated hydrochloric acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS219165 | 1965-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1123094A true GB1123094A (en) | 1968-08-14 |
Family
ID=5358305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1448066A Expired GB1123094A (en) | 1965-04-02 | 1966-04-01 | A process for the production of substituted 2,7-bis(phenylazc) derivatives of chromotropic acid |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT267017B (en) |
| BE (1) | BE678839A (en) |
| CH (1) | CH479679A (en) |
| DE (1) | DE1544461A1 (en) |
| GB (1) | GB1123094A (en) |
| SE (1) | SE320449B (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512246A (en) * | 1989-09-21 | 1996-04-30 | Anthony P. Russell | Method and means for detecting polyhydroxyl compounds |
| WO2003104332A1 (en) * | 2002-06-07 | 2003-12-18 | Avecia Limited | Compositions and inks containing disazo dyes |
| WO2006113477A3 (en) * | 2005-04-19 | 2007-05-10 | Specialty Assays Inc | Use of phosphonazo iii for the measurement of calcium, magnesium and sodium in analytical samples |
| US7481522B2 (en) | 2002-06-07 | 2009-01-27 | Fujifilm Imaging Colorants Limited | Compositions and inks containing disazo dyes |
| US8088097B2 (en) | 2007-11-21 | 2012-01-03 | Glumetrics, Inc. | Use of an equilibrium intravascular sensor to achieve tight glycemic control |
| US8467843B2 (en) | 2009-11-04 | 2013-06-18 | Glumetrics, Inc. | Optical sensor configuration for ratiometric correction of blood glucose measurement |
| US8512245B2 (en) | 2008-04-17 | 2013-08-20 | Glumetrics, Inc. | Sensor for percutaneous intravascular deployment without an indwelling cannula |
| US8715589B2 (en) | 2009-09-30 | 2014-05-06 | Medtronic Minimed, Inc. | Sensors with thromboresistant coating |
| US8738107B2 (en) | 2007-05-10 | 2014-05-27 | Medtronic Minimed, Inc. | Equilibrium non-consuming fluorescence sensor for real time intravascular glucose measurement |
| US8838195B2 (en) | 2007-02-06 | 2014-09-16 | Medtronic Minimed, Inc. | Optical systems and methods for ratiometric measurement of blood glucose concentration |
| CN120925108A (en) * | 2025-10-16 | 2025-11-11 | 江苏恒力化纤股份有限公司 | A DTY fiber and its preparation method |
-
1966
- 1966-02-17 AT AT145666A patent/AT267017B/en active
- 1966-02-18 CH CH242166A patent/CH479679A/en not_active IP Right Cessation
- 1966-03-11 SE SE327866A patent/SE320449B/xx unknown
- 1966-03-26 DE DE19661544461 patent/DE1544461A1/en active Pending
- 1966-04-01 BE BE678839D patent/BE678839A/xx unknown
- 1966-04-01 GB GB1448066A patent/GB1123094A/en not_active Expired
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512246A (en) * | 1989-09-21 | 1996-04-30 | Anthony P. Russell | Method and means for detecting polyhydroxyl compounds |
| US7481522B2 (en) | 2002-06-07 | 2009-01-27 | Fujifilm Imaging Colorants Limited | Compositions and inks containing disazo dyes |
| WO2003104332A1 (en) * | 2002-06-07 | 2003-12-18 | Avecia Limited | Compositions and inks containing disazo dyes |
| EP1872122A4 (en) * | 2005-04-19 | 2011-03-09 | Specialty Assays Inc | Use of phosphonazo iii for the measurement of calcium, magnesium and sodium in analytical samples |
| JP2008537144A (en) * | 2005-04-19 | 2008-09-11 | スペシャルティー アッセイズ，インコーポレーテッド | Method using phosphonazo III for the determination of calcium, magnesium and sodium in analytical samples |
| US7288414B2 (en) * | 2005-04-19 | 2007-10-30 | Specialty Assays, Inc. | Use of phosphonazo III for the measurement of calcium, magnesium and sodium in analytical samples |
| WO2006113477A3 (en) * | 2005-04-19 | 2007-05-10 | Specialty Assays Inc | Use of phosphonazo iii for the measurement of calcium, magnesium and sodium in analytical samples |
| US8838195B2 (en) | 2007-02-06 | 2014-09-16 | Medtronic Minimed, Inc. | Optical systems and methods for ratiometric measurement of blood glucose concentration |
| US9839378B2 (en) | 2007-02-06 | 2017-12-12 | Medtronic Minimed, Inc. | Optical systems and methods for ratiometric measurement of blood glucose concentration |
| US8738107B2 (en) | 2007-05-10 | 2014-05-27 | Medtronic Minimed, Inc. | Equilibrium non-consuming fluorescence sensor for real time intravascular glucose measurement |
| US8088097B2 (en) | 2007-11-21 | 2012-01-03 | Glumetrics, Inc. | Use of an equilibrium intravascular sensor to achieve tight glycemic control |
| US8535262B2 (en) | 2007-11-21 | 2013-09-17 | Glumetrics, Inc. | Use of an equilibrium intravascular sensor to achieve tight glycemic control |
| US8979790B2 (en) | 2007-11-21 | 2015-03-17 | Medtronic Minimed, Inc. | Use of an equilibrium sensor to monitor glucose concentration |
| US8512245B2 (en) | 2008-04-17 | 2013-08-20 | Glumetrics, Inc. | Sensor for percutaneous intravascular deployment without an indwelling cannula |
| US8715589B2 (en) | 2009-09-30 | 2014-05-06 | Medtronic Minimed, Inc. | Sensors with thromboresistant coating |
| US8700115B2 (en) | 2009-11-04 | 2014-04-15 | Glumetrics, Inc. | Optical sensor configuration for ratiometric correction of glucose measurement |
| US8467843B2 (en) | 2009-11-04 | 2013-06-18 | Glumetrics, Inc. | Optical sensor configuration for ratiometric correction of blood glucose measurement |
| CN120925108A (en) * | 2025-10-16 | 2025-11-11 | 江苏恒力化纤股份有限公司 | A DTY fiber and its preparation method |
Also Published As
| Publication number | Publication date |
|---|---|
| CH479679A (en) | 1969-10-15 |
| SE320449B (en) | 1970-02-09 |
| AT267017B (en) | 1968-12-10 |
| BE678839A (en) | 1966-09-16 |
| DE1544461A1 (en) | 1970-04-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1123094A (en) | A process for the production of substituted 2,7-bis(phenylazc) derivatives of chromotropic acid | |
| US4014866A (en) | Barium laked phenylazonaphthalene dye containing sulfonic acid groups | |
| US901675A (en) | Yellow azo dye and process of making same. | |
| US733280A (en) | Red azo dye and process of making same. | |
| US2174501A (en) | Sodium salt of lithol red as a dry toner | |
| Bogert et al. | THE SYNTHESIS OF AMINOFLAVONES, OF FLAVONE-AZOBETA-NAPHTHOL DYES, AND OF OTHER FLAVONE DERIVATIVES. | |
| US3527749A (en) | Heterocyclic 2,7-bisazo derivatives of chromotropic acid | |
| US2092796A (en) | Azo dyes and pigments derived therefrom | |
| US741029A (en) | Red azo lake. | |
| US1126413A (en) | Azo dyestuff. | |
| US826279A (en) | Ortho-oxyazo dye. | |
| US2280072A (en) | Substituted phthalocyanines | |
| US1848650A (en) | of basel | |
| DE609928C (en) | Process for the preparation of 2-amino-1-oxynaphthalene-8-sulfonic acid | |
| US1234994A (en) | Copper compounds of orthooxyazo dyestuffs and a process of making same. | |
| US683119A (en) | Blue monoazo dye. | |
| CH273303A (en) | Process for the preparation of a metal-containing monoazo dye. | |
| US1358007A (en) | Colors | |
| US316036A (en) | The-main | |
| US2083311A (en) | Diazonium salts | |
| US839605A (en) | Yellow azo dye. | |
| US826280A (en) | Ortho-oxymonoazo dye. | |
| US795058A (en) | Bisulfite compound of a tetrazo dye and process of making same. | |
| US1485814A (en) | Dyestuffs capable of being chromed and process of making same | |
| US806415A (en) | Blue azo dye and process of making same. |