US2783227A - Naphthoyl leuco methylene blue - Google Patents
Naphthoyl leuco methylene blue Download PDFInfo
- Publication number
- US2783227A US2783227A US518332A US51833255A US2783227A US 2783227 A US2783227 A US 2783227A US 518332 A US518332 A US 518332A US 51833255 A US51833255 A US 51833255A US 2783227 A US2783227 A US 2783227A
- Authority
- US
- United States
- Prior art keywords
- naphthoyl
- blue
- methylene blue
- leuco methylene
- 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 - Lifetime
Links
- -1 Naphthoyl leuco methylene blue Chemical compound 0.000 title description 4
- GNIWEHRVQPUXAB-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-naphthalen-1-ylmethanone Chemical compound C1(=CC=CC2=CC=CC=C12)C(=O)N1C2=CC=C(C=C2SC=2C=C(C=CC1=2)N(C)C)N(C)C GNIWEHRVQPUXAB-UHFFFAOYSA-N 0.000 claims 1
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 239000000376 reactant Substances 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
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 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
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-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
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 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 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 229910052621 halloysite Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 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
- the known leucomethylene blue compound IO-benzoyl- 3,7-bis(dimethylamino)phenothiazine has been used as a color reactant in connection with manifold sheets such as those described in the United States Patent No. 2,646,367, which issued on the application of Chester Davis and Ned A. Thacker on July 21, 1953.
- a manifold sheet having a colorless transfer coating on one side, the coating being made of wax and an oil having dissolved in it the colorless color reactant crystal violet lactone, which is 3,3-bis- (p-dimethylaminophenyl)-6-dimethylaminophthalide, and the beforementioned benzoyl leucomethylene blue.
- the benzoyl leucomethylene blue has one characteristic in its disfavor, and that is that it slowly decomposes to the blue-green color on exposure to light, which means that, if the transfer coating is exposed to light for a long time, it turns to an undesirable blue-green color.
- the manufacture of l0-(2-naphthoyl)-3,7-bis (dimethylamino)phenothiazine may be started with the commercially available zinc chloride double salt of leucomethylene blue, having the structure
- To 35 grams (0.0706 mole) of the zinc chloride double salt of leucomethylene blue is added 97 grams (1.25 moles) of pyridine in a three-necked, round-bottom flask fitted with a mechanical stirrer, a thermometer, and a reflux condenser.
- To the above mixture is added slowly 25 grams (0.131 mole) of 2-naphthoyl chloride while 2,783,227 Patented Feb. 26, 1957 2 stirring.
- the reaction mixture is refluxed gently for one hour.
- the resultant hot reaction mixture then is poured into one liter of cold water andmechanically stirred for one half hour.
- the brown semi-solid precipitate which forms is washed with water and thereafter stirred with 17.5 grams of sodium hydroxide dissolved in one half liter of water for one half hour.
- the alkaline solution then is decanted ofi, and the semi-solid residue is washed with water and extracted with 2.2 liters of hot benzene.
- the dark benzene solution then is treated with fullers earth and filtered.
- the resultant amber filtrate is concentrated to 400 milliliters and precipitated with petroleum ether.
- the resulting final product, l0-(2-naphthoyl)-3,7-bis- (dimethylamino)phenothiazine, is a light yellow crystalline material having the following structure:
- IO-(I-naphthoyl)-3,7-bis(dimethylamino)phenothiazine having the i in which R is taken from the group consisting of l-naphthoyl and 2-naphthoyl.
- the substantially light-stable leucomethylene blue derivative 10 (2-naphthoyl) 3,7 bis(dimethylamino)- phenothiazine having the following structure:
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 |
|---|---|---|---|
| NL94594D NL94594C (enrdf_load_stackoverflow) | 1955-06-27 | ||
| NL208241D NL208241A (enrdf_load_stackoverflow) | 1955-06-27 | ||
| US518332A US2783227A (en) | 1955-06-27 | 1955-06-27 | Naphthoyl leuco methylene blue |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US518332A US2783227A (en) | 1955-06-27 | 1955-06-27 | Naphthoyl leuco methylene blue |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2783227A true US2783227A (en) | 1957-02-26 |
Family
ID=24063470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US518332A Expired - Lifetime US2783227A (en) | 1955-06-27 | 1955-06-27 | Naphthoyl leuco methylene blue |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2783227A (enrdf_load_stackoverflow) |
| NL (2) | NL208241A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909520A (en) * | 1959-10-20 | Process for making acylated | ||
| US2915415A (en) * | 1957-06-19 | 1959-12-01 | Caribonum Ltd | Leucauramine derivate of benzoyl leuco methylene blue and transfer sheet coated therewith |
| US3873340A (en) * | 1972-07-27 | 1975-03-25 | Hodogaya Chemical Co Ltd | Pressure-sensitive copying paper containing phenoxazine compounds |
| US4237281A (en) * | 1978-10-13 | 1980-12-02 | Ciba-Geigy Aktiengesellschaft | Dyestuffs containing amino or imino groups |
| 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 NL94594D patent/NL94594C/xx active
- NL NL208241D patent/NL208241A/xx unknown
-
1955
- 1955-06-27 US US518332A patent/US2783227A/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 |
|---|---|---|---|---|
| US2909520A (en) * | 1959-10-20 | Process for making acylated | ||
| US2915415A (en) * | 1957-06-19 | 1959-12-01 | Caribonum Ltd | Leucauramine derivate of benzoyl leuco methylene blue and transfer sheet coated therewith |
| US3873340A (en) * | 1972-07-27 | 1975-03-25 | Hodogaya Chemical Co Ltd | Pressure-sensitive copying paper containing phenoxazine compounds |
| US4237281A (en) * | 1978-10-13 | 1980-12-02 | Ciba-Geigy Aktiengesellschaft | Dyestuffs containing amino or imino groups |
| 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 |
|---|---|
| NL94594C (enrdf_load_stackoverflow) | |
| NL208241A (enrdf_load_stackoverflow) |
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