GB770574A - Colouring compositions containing dyes of the triarylmethane series - Google Patents
Colouring compositions containing dyes of the triarylmethane seriesInfo
- Publication number
- GB770574A GB770574A GB3046/55A GB304655A GB770574A GB 770574 A GB770574 A GB 770574A GB 3046/55 A GB3046/55 A GB 3046/55A GB 304655 A GB304655 A GB 304655A GB 770574 A GB770574 A GB 770574A
- Authority
- GB
- United Kingdom
- Prior art keywords
- leuco
- ethyl
- mixed
- aqueous
- trimethylammonium hydroxide
- 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 6
- 239000000203 mixture Substances 0.000 title abstract 5
- 238000004040 coloring Methods 0.000 title 1
- -1 mononitrophenyl Chemical group 0.000 abstract 11
- 150000001875 compounds Chemical class 0.000 abstract 9
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 abstract 3
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 abstract 3
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 abstract 3
- HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000000908 ammonium hydroxide Substances 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 abstract 2
- 229960001231 choline Drugs 0.000 abstract 2
- JVICFMRAVNKDOE-UHFFFAOYSA-M ethyl violet Chemical compound [Cl-].C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 JVICFMRAVNKDOE-UHFFFAOYSA-M 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000002955 isolation Methods 0.000 abstract 2
- 238000002156 mixing Methods 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 abstract 1
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000004203 carnauba wax Substances 0.000 abstract 1
- 235000013869 carnauba wax Nutrition 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- FQDOXHIOXBSBDS-UHFFFAOYSA-N n,n-dibutyl-4-[[4-(dibutylamino)phenyl]methyl]aniline Chemical compound C1=CC(N(CCCC)CCCC)=CC=C1CC1=CC=C(N(CCCC)CCCC)C=C1 FQDOXHIOXBSBDS-UHFFFAOYSA-N 0.000 abstract 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 abstract 1
- PPHQUIPUBYPZLD-UHFFFAOYSA-N n-ethyl-n-methylaniline Chemical compound CCN(C)C1=CC=CC=C1 PPHQUIPUBYPZLD-UHFFFAOYSA-N 0.000 abstract 1
- IPSIPYMEZZPCPY-UHFFFAOYSA-N new fuchsin Chemical compound [Cl-].C1=CC(=[NH2+])C(C)=CC1=C(C=1C=C(C)C(N)=CC=1)C1=CC=C(N)C(C)=C1 IPSIPYMEZZPCPY-UHFFFAOYSA-N 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
- 239000012188 paraffin wax Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 239000001003 triarylmethane dye Substances 0.000 abstract 1
- 229940099259 vaseline Drugs 0.000 abstract 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 abstract 1
- 125000005023 xylyl group Chemical group 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
-
- 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
- B41M5/025—Duplicating or marking methods; Sheet materials for use therein by transferring ink from the master sheet
- B41M5/0253—Duplicating or marking methods; Sheet materials for use therein by transferring ink from the master sheet using a chemical colour-forming ink, e.g. chemical hectography
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S101/00—Printing
- Y10S101/29—Printing involving a color-forming phenomenon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Color Printing (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
Dyestuff compositions for duplicating and typewriting comprise at least one leuco triarylmethane dye as defined below together with a quaternary ammonium hydroxide in quantity sufficient to stabilize the leuco compound against photochemical oxidation, oxidation to the dye taking place after the compositions have been applied to a stratum. The leuco compounds have the formula:- <FORM:0770574/IV(b)/1> wherein X is H or methyl, R represents phenyl, tolyl, xylyl, mononitrophenyl, mono- and dichlorphenyl, 1 - p - phenylamino - naphthyl, 1 - p - monoalkylamino-or dialkylamino - naphthyl, or an aminophenyl or aminotolyl radical, said aminophenyl or aminotolyl radical may have one or both of the hydrogen atoms of their amino groups substituted by alkyl of less than 5 carbon atoms, acetyl, 2 - hydroxyethyl, 2 -cyanoethyl, benzyl, or phenyl, and R1, R2, R3, and R4 represent hydrogen, alkyl of less than five carbon atoms, 2 - hydroxyethyl 2 - cyanoethyl, benzyl or phenyl, said leuco compounds being devoid of sulpho, carboxy, or phenolic hydroxy groups. Preferably, sufficient quaternary ammonium hydroxide is added to give a pH of not less than 8 to a 1 per cent solution of the composition in ethanol at room temperature. The two ingredients are mixed by (1) stirring a solution of the purified leuco compound in an organic solvent with an aqueous solution of the base, (2) mixing both in an organic solvent and precipitating by cooling or diluting with a non-solvent for the leuco compound. (3) forming the leuco compound by alkaline reduction of the dye or by synthesis and mixing with an aqueous solution of the base without isolation. In examples:- (1) the leuco compounds of ethyl violet and crystal violet, prepared by reduction of the commercial colour, are each mixed in ethanol with aqueous benzyl trimethylammonium hydroxide; (2) the neutralized synthesis reaction mixtures from p-diethylaminobenzaldehyde and diethylaniline or N-diethyl - o - toluidine are each mixed with aqueous choline and those from p - diethylaminobenzaldehyde and N - ethyl -N - benzylaniline or N - ethyl - N - (b - hydroxyethyl) - o - toluidine or N - (b - cyanoethyl) - N - methyl - aniline (in this latter case p - dimethylaminobenzaldehyde may replace p-diethylaminobenzaldehyde) are each mixed with aqueous benzyl trimethylammonium hydroxide; (3) di (p-dimethylamino - phenyl) hydrol is condensed with diethylaniline and the separated leuco compound recrystallized from isopropanol in presence of benzyl trimethylammonium hydroxide; (4) di (p - di - n - butylaminophenyl) - methane is converted to the hydrol by action of lead peroxide and this hydrol is condensed with di - n - butylaniline, diethylaniline, N - ethyl - N - methyl - aniline, or N - b - cyanoethyl - N - methyl aniline and the neutralized product is mixed with benzyl trimethylammonium hydroxide; (5) Victoria Blue BO, Brilliant Green, New fuchsine and paraleucaniline, are reduced to their leuco compounds with zinc dust and sodium hydrosulphite and without isolation are admixed with aqueous benzyl trimethylammonium hydroxide, and fuchsine is similarly reduced and admixed with choline; (6) the neutralized condensation products from benzaldehyde and N - ethyl - N - benzylaniline, o - chlorbenzaldehyde and N.N - diethylaniline, p -chlorbenzaldehyde and N.N - dimethylani line, and p - chlorbenzaldehyde and N - ethyl - N - benzylaniline are mixed with benzyl trimethylammonium hydroxide. Other dyes and bases are listed. Examples describe the preparation of colourless transfer sheets for single or multiple reproduction, which may be developed with a chloranil - dioxane - alcohol solution, using compositions comprising the stabilized dyes of the invention, octadecyl and hexadecyl amines, paraffin wax, aluminium stearate, carnauba wax, and "Vaseline" (Registered Trade Mark) and if desired other non-smudging azo dyes.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US456880A US2755203A (en) | 1954-02-03 | 1954-02-03 | Process of converting a polyamino-triarylmethane dye coating on a base from a stabilized leuco form to a colored form |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB770574A true GB770574A (en) | 1957-03-20 |
Family
ID=26711218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3046/55A Expired GB770574A (en) | 1954-02-03 | 1955-02-02 | Colouring compositions containing dyes of the triarylmethane series |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2755203A (en) |
| CH (1) | CH346568A (en) |
| DE (1) | DE1036278B (en) |
| GB (1) | GB770574A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996000272A1 (en) * | 1994-06-27 | 1996-01-04 | Basf Aktiengesellschaft | Use of leucotriarylmethanes for marking hydrocarbons |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2935938A (en) * | 1956-04-17 | 1960-05-10 | Eugene Lefebure | Methods of copy reproduction |
| US2934007A (en) * | 1957-05-29 | 1960-04-26 | Caribonum Ltd | Duplicating machines |
| US2978352A (en) * | 1957-07-25 | 1961-04-04 | Du Pont | Production of triarylmethane colors |
| US2927040A (en) * | 1957-08-13 | 1960-03-01 | Davis Chester | Non-staining triarylmethane color base and method of printing therewith |
| US2927041A (en) * | 1957-08-13 | 1960-03-01 | Davis Chester | Non-staining transfer sheet |
| US2949377A (en) * | 1957-10-30 | 1960-08-16 | Steinhardt Amos | Transfer composition containing a triphenylcarbinol compound and precipitated calcium carbonate |
| US2999026A (en) * | 1958-04-03 | 1961-09-05 | Davis Chester | Nonstaining pigments and their use |
| US3021344A (en) * | 1959-08-19 | 1962-02-13 | Du Pont | Triphenylmethane dyes |
| DE1128870B (en) * | 1960-05-18 | 1962-05-03 | Wilhelm Ritzerfeld | Process for the production of copies or printing forms by photothermal means |
| NL277913A (en) * | 1961-05-03 | |||
| NL120357C (en) * | 1961-05-03 | |||
| NL292921A (en) * | 1963-05-17 | 1900-01-01 | ||
| US3449379A (en) * | 1963-06-26 | 1969-06-10 | Du Pont | Triphenylmethane derivatives |
| US3429900A (en) * | 1963-08-26 | 1969-02-25 | Allied Chem | Stable triphenyl-methane dye leucos |
| US3447944A (en) * | 1965-12-06 | 1969-06-03 | Sterling Drug Inc | Thermographic copying system |
| JPS5030088B2 (en) * | 1973-04-16 | 1975-09-29 | ||
| CH626568A5 (en) * | 1977-06-10 | 1981-11-30 | Ciba Geigy Ag | |
| USRE30803E (en) * | 1977-11-09 | 1981-11-24 | Scott Paper Company | Colorless recording paper |
| USRE30797E (en) * | 1977-11-09 | 1981-11-17 | Scott Paper Company | Associated dye salts and method of forming colored indicia therewith |
| US4398753A (en) * | 1980-12-26 | 1983-08-16 | Mitsui Toatsu Chemicals, Incorporated | Pressure sensitive recording unit |
| EP3292173A1 (en) * | 2015-05-04 | 2018-03-14 | Milliken & Company | Leuco triphenylmethane colorants as bluing agents in laundry care compositions |
| US20180119056A1 (en) * | 2016-11-03 | 2018-05-03 | Milliken & Company | Leuco Triphenylmethane Colorants As Bluing Agents in Laundry Care Compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2548365A (en) * | 1948-07-13 | 1951-04-10 | Ncr Co | Process for making pressure sensitive record materials |
| BE492062A (en) * | 1948-11-16 | |||
| BE500662A (en) * | 1950-01-18 |
-
1954
- 1954-02-03 US US456880A patent/US2755203A/en not_active Expired - Lifetime
-
1955
- 1955-02-01 DE DEP13479A patent/DE1036278B/en active Pending
- 1955-02-02 GB GB3046/55A patent/GB770574A/en not_active Expired
- 1955-02-02 CH CH346568D patent/CH346568A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996000272A1 (en) * | 1994-06-27 | 1996-01-04 | Basf Aktiengesellschaft | Use of leucotriarylmethanes for marking hydrocarbons |
Also Published As
| Publication number | Publication date |
|---|---|
| US2755203A (en) | 1956-07-17 |
| DE1036278B (en) | 1958-08-14 |
| CH346568A (en) | 1960-05-31 |
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