US2783228A - Nitro derivatives of benzoyl leuco methylene blue - Google Patents
Nitro derivatives of benzoyl leuco methylene blue Download PDFInfo
- Publication number
- US2783228A US2783228A US518333A US51833355A US2783228A US 2783228 A US2783228 A US 2783228A US 518333 A US518333 A US 518333A US 51833355 A US51833355 A US 51833355A US 2783228 A US2783228 A US 2783228A
- Authority
- US
- United States
- Prior art keywords
- color
- blue
- methylene blue
- nitro derivatives
- leuco methylene
- 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 - Lifetime
Links
- 150000002828 nitro derivatives Chemical class 0.000 title description 3
- 229960000907 methylthioninium chloride Drugs 0.000 title 1
- -1 10 -NITROBENZOYL -3,7-BIS(DIMETHYLAMINO)PHENOTHIAZINE Chemical compound 0.000 claims description 4
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 5
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical class C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 4
- 229960000892 attapulgite Drugs 0.000 description 4
- 229910052621 halloysite Inorganic materials 0.000 description 4
- 229910052625 palygorskite Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 2
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- CEZVAZTZKUQHGY-UHFFFAOYSA-N n,n-dimethyl-10h-phenothiazin-1-amine Chemical compound S1C2=CC=CC=C2NC2=C1C=CC=C2N(C)C CEZVAZTZKUQHGY-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- DDCCHUHICUGJCF-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazine Chemical compound S1C2=CC(N(C)C)=CC=C2N=C2C1C=C(N(C)C)C=C2 DDCCHUHICUGJCF-UHFFFAOYSA-N 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 description 1
- 235000012745 brilliant blue FCF Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
Definitions
- This invention relates to the light-stable leucomethylene blue derivative 10 (nitrobenzoyl) -"3,7 bis(dimethylamino)phenothiazine, having the structure S (ormmgsgmcmn 10 N and in which R is taken from the group consisting of 4-nitro and 3-nitro.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Color Printing (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL94595D NL94595C (enrdf_load_stackoverflow) | 1955-06-27 | ||
| NL208242D NL208242A (enrdf_load_stackoverflow) | 1955-06-27 | ||
| US518333A US2783228A (en) | 1955-06-27 | 1955-06-27 | Nitro derivatives of benzoyl leuco methylene blue |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US518333A US2783228A (en) | 1955-06-27 | 1955-06-27 | Nitro derivatives of benzoyl leuco methylene blue |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2783228A true US2783228A (en) | 1957-02-26 |
Family
ID=24063475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US518333A Expired - Lifetime US2783228A (en) | 1955-06-27 | 1955-06-27 | Nitro derivatives of benzoyl leuco methylene blue |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2783228A (enrdf_load_stackoverflow) |
| NL (2) | NL94595C (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2915415A (en) * | 1957-06-19 | 1959-12-01 | Caribonum Ltd | Leucauramine derivate of benzoyl leuco methylene blue and transfer sheet coated therewith |
| US3427180A (en) * | 1965-03-31 | 1969-02-11 | Ncr Co | Pressure-sensitive record system and compositions |
| US3447944A (en) * | 1965-12-06 | 1969-06-03 | Sterling Drug Inc | Thermographic copying system |
| US3873340A (en) * | 1972-07-27 | 1975-03-25 | Hodogaya Chemical Co Ltd | Pressure-sensitive copying paper containing phenoxazine compounds |
| US4563415A (en) * | 1983-04-05 | 1986-01-07 | Minnesota Mining And Manufacturing Company | Thermographic system using naphthoylated leuco phenazine dyes |
| US4647525A (en) * | 1984-10-01 | 1987-03-03 | Minnesota Mining And Manufacturing Company | Stabilized leuco phenazine dyes and their use in an imaging system |
| US4889932A (en) * | 1984-10-01 | 1989-12-26 | Minnesota Mining And Manufacturing Company | Stabilized leuco phenazine dyes and their use in an imaging system |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE512300A (enrdf_load_stackoverflow) * | 1951-06-23 | |||
| DE113721C (de) * | 1899-06-01 | 1900-09-28 | Verfahren zur Darstellung von Acidylderivaten der Leukothioninfarbstoffe |
-
0
- NL NL208242D patent/NL208242A/xx unknown
- NL NL94595D patent/NL94595C/xx active
-
1955
- 1955-06-27 US US518333A patent/US2783228A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE113721C (de) * | 1899-06-01 | 1900-09-28 | Verfahren zur Darstellung von Acidylderivaten der Leukothioninfarbstoffe | |
| BE512300A (enrdf_load_stackoverflow) * | 1951-06-23 |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2915415A (en) * | 1957-06-19 | 1959-12-01 | Caribonum Ltd | Leucauramine derivate of benzoyl leuco methylene blue and transfer sheet coated therewith |
| US3427180A (en) * | 1965-03-31 | 1969-02-11 | Ncr Co | Pressure-sensitive record system and compositions |
| US3447944A (en) * | 1965-12-06 | 1969-06-03 | Sterling Drug Inc | Thermographic copying system |
| US3873340A (en) * | 1972-07-27 | 1975-03-25 | Hodogaya Chemical Co Ltd | Pressure-sensitive copying paper containing phenoxazine compounds |
| US4563415A (en) * | 1983-04-05 | 1986-01-07 | Minnesota Mining And Manufacturing Company | Thermographic system using naphthoylated leuco phenazine dyes |
| US4647525A (en) * | 1984-10-01 | 1987-03-03 | Minnesota Mining And Manufacturing Company | Stabilized leuco phenazine dyes and their use in an imaging system |
| US4889932A (en) * | 1984-10-01 | 1989-12-26 | Minnesota Mining And Manufacturing Company | Stabilized leuco phenazine dyes and their use in an imaging system |
Also Published As
| Publication number | Publication date |
|---|---|
| NL94595C (enrdf_load_stackoverflow) | |
| NL208242A (enrdf_load_stackoverflow) |
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