GB1027620A - New leuco triphenylmethane derivatives - Google Patents
New leuco triphenylmethane derivativesInfo
- Publication number
- GB1027620A GB1027620A GB34785/64A GB3478564A GB1027620A GB 1027620 A GB1027620 A GB 1027620A GB 34785/64 A GB34785/64 A GB 34785/64A GB 3478564 A GB3478564 A GB 3478564A GB 1027620 A GB1027620 A GB 1027620A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- leuco
- ethyl
- formula
- hydroxyethyl
- 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
- 150000004961 triphenylmethanes Chemical class 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkyl radical Chemical class 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- 239000001993 wax Substances 0.000 abstract 2
- ULUZGMIUTMRARO-UHFFFAOYSA-N (carbamoylamino)urea Chemical compound NC(=O)NNC(N)=O ULUZGMIUTMRARO-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 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
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000005215 alkyl ethers Chemical class 0.000 abstract 1
- 150000003935 benzaldehydes Chemical class 0.000 abstract 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 239000004203 carnauba wax Substances 0.000 abstract 1
- 235000013869 carnauba wax Nutrition 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000012170 montan wax Substances 0.000 abstract 1
- 239000000025 natural resin Substances 0.000 abstract 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/14—Preparation from aromatic aldehydes, aromatic carboxylic acids or derivatives thereof and aromatic amines
-
- 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
- B41M5/1366—Organic colour formers, e.g. leuco dyes characterised solely by tri (aryl or hetaryl)methane derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Color Printing (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
The invention comprises leuco derivatives of polyaminotriphenylmethanes of the formula <FORM:1027620/C4-C5/1> wherein x is 2 or 3, R1 and R2 are each methyl or ethyl, R3 is chlorine, bromine, methyl or ethyl, and R4 is hydrogen, dialkylamino, or N - hydroxyalkyl - N - alkylamino wherein each alkyl radical contains not more than two carbon atoms. The compounds are made by reacting two moles of an N-alkanol-N-alkyl-aniline of the formula <FORM:1027620/C4-C5/2> with one mole of an ortho-substituted benzaldehyde of the formula <FORM:1027620/C4-C5/3> The condensation is preferably effected at a temperature of at least 50 DEG C. in the presence of an inert solvent and a strong, water-soluble, non-oxidizing acid, as catalyst, e.g. sulphuric, phosphoric, hydrochloric, formic, trichloracetic, or p-toluene sulphonic acid. The reaction rate is increased by the presence of at least 0.5 mol of urea, thiourea, biuret, nitrourea or biurea. Alcoholic solvents or lower alkyl ethers of ethylene glycol or mixtures thereof may be used as solvents. The reaction mass is cooled, neutralized by addition of alkali, filtered, diluted with water and allowed to stand whereupon the leuco product crystallizes from solution. Examples describe the preparation of leuco 2 - chloro - N1,N11 - bis - (b - hydroxyethyl) - N,N,N1,N11 - tetramethyl - 4,41,411-triaminotriphenylmethane, leuco 2-methyl-N,N-diethyl - N1,N11 - dimethyl - N1,N11 - bis - (b -hydroxyethyl) - 4,41,411 - triaminotriphenyl-methane, and leuco 2 - chloro - N1,N11 - bis - (b - hydroxyethyl) - N1,N11 - dimethyl - 41,411-diaminotriphenylmethane.ALSO:An impact sensitive manifold copy paper comprises as the chromogenic electron donor a lenco derivative of polyaminotriphenyl-methanes having the formula: <FORM:1027620/D1-D2/1> wherein x is 2 or 3, R1 and R2 are each methyl or ethyl, R3 is chlorine, bromine, methyl or ethyl, and R4 is hydrogen, dialkylamino, or N-hydroxyalkyl-N-alkylamino, wherein each alkyl radical contains not more than two carbon atoms. The chromogen may be coated on to the paper as a wax emulsion using any of the waxes commonly used in the art, e.g. carnauba wax and montan wax. In addition, natural and synthetic resin binders can be used, e.g. polyvinyl alcohol or cellulose acetate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30463163A | 1963-08-26 | 1963-08-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1027620A true GB1027620A (en) | 1966-04-27 |
Family
ID=23177314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34785/64A Expired GB1027620A (en) | 1963-08-26 | 1964-08-25 | New leuco triphenylmethane derivatives |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3429900A (en) |
| CH (1) | CH445694A (en) |
| GB (1) | GB1027620A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2478086A1 (en) * | 1980-02-14 | 1981-09-18 | Ciba Geigy Ag | PROCESS FOR THE PREPARATION OF TRIARYLMETHANE COMPOUNDS |
| EP0057661A2 (en) * | 1981-01-22 | 1982-08-11 | Ciba-Geigy Ag | Process for the production of leuco triaryl methane compounds |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5194390A (en) * | 1988-07-05 | 1993-03-16 | Miles Inc. | Composition for the assay of albumin |
| US5278023A (en) * | 1992-11-16 | 1994-01-11 | Minnesota Mining And Manufacturing Company | Propellant-containing thermal transfer donor elements |
| TW201922942A (en) * | 2017-10-12 | 2019-06-16 | 美商美力肯及公司 | Triarylmethane leuco compounds and compositions comprising the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191413604A (en) * | 1914-06-04 | 1915-08-05 | Philip Arthur Newton | Manufacture and Production of New Dyes of the Triphenylmethane Series. |
| US2755203A (en) * | 1954-02-03 | 1956-07-17 | Du Pont | Process of converting a polyamino-triarylmethane dye coating on a base from a stabilized leuco form to a colored form |
| US2726252A (en) * | 1954-08-25 | 1955-12-06 | Du Pont | Process for preparing leuco-triaryl-methane compounds |
-
1963
- 1963-08-26 US US304631A patent/US3429900A/en not_active Expired - Lifetime
-
1964
- 1964-08-25 GB GB34785/64A patent/GB1027620A/en not_active Expired
- 1964-08-26 CH CH1116564A patent/CH445694A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2478086A1 (en) * | 1980-02-14 | 1981-09-18 | Ciba Geigy Ag | PROCESS FOR THE PREPARATION OF TRIARYLMETHANE COMPOUNDS |
| EP0057661A2 (en) * | 1981-01-22 | 1982-08-11 | Ciba-Geigy Ag | Process for the production of leuco triaryl methane compounds |
| EP0057661A3 (en) * | 1981-01-22 | 1982-08-25 | Ciba-Geigy Ag | Process for the production of leuco triaryl methane compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| US3429900A (en) | 1969-02-25 |
| CH445694A (en) | 1967-10-31 |
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