US3337549A - 1-[tertiary amino-carbanilido]-3, 5-dihydroxy-4-bromo benzenes - Google Patents
1-[tertiary amino-carbanilido]-3, 5-dihydroxy-4-bromo benzenes Download PDFInfo
- Publication number
- US3337549A US3337549A US440982A US44098265A US3337549A US 3337549 A US3337549 A US 3337549A US 440982 A US440982 A US 440982A US 44098265 A US44098265 A US 44098265A US 3337549 A US3337549 A US 3337549A
- Authority
- US
- United States
- Prior art keywords
- dihydroxy
- formula
- compound
- bromo
- benzene
- 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Definitions
- This invention relates to photoprinting materials and refers more particularly to two-component diazotype photo-printing materials and to the diazo compounds and couplers used therein.
- R for alkyl with 1 to 4 carbon atoms
- R and R for similar or differing alkyl radicals with 1 to 5 carbon atoms
- R and R may also be members of one and the same heterocyclic ring which may carry one or more substituents.
- the known diazo compounds corresponding to this formula are very light sensitive.
- diazotype photoprinting papers which contain, as diazo component in the light sensitive coatin-g, compounds with the Formula I given above and, as a coupling component, salts of 4-bromo- 3,5-dihydroxy benzoic acid anilides corresponding to Formula II in which R and R stand for alkyl with 1 to 3 carbon atoms or are members of one and the same heterocyclic fivemembered or six-membered ring which may carry one or more substituents, and
- Y is a member selected from the group consisting of hydrogen, alkyl, and halide radicals
- the compounds formed by the introduction of a tertiaryalkylamino group into the phenyl portion of the carboxamide group have very good water-solubility if used in the form of their salts. They are also in the form or" their water-soluble salts if applied together with the diazo compound in aqueous solution containing acid additives.
- the group NR R in Formula I or the group NR R in Formula II, or both these groups may stand for heterocyclic groups which may carry one or more substituents, e.g. one or more alkyl groups.
- Suitable groups are the pyrrolidone group, the piperazine group, the morpholine group, the Z-methyl-morpholine group, the 2-ethyl-morpholine group, the 2,3-, the 2,5-, the 2,6-, and the 3,5-dimethylmorpholine groups, the 2,6-diethyl-morpholine group, the 3,5- and the 5,2-methyl-ethyl-morpholine groups, the 2,3,5-trimethyl-morpholine group, and the thio-morpholine group.
- One object of the present invention is to provide a two-component diazotype photoprinting material which does not have the disadvantages of the prior art.
- Another object is to provide a two component diazotype photoprinting material which has a developed image with improved color intensity, improved color shades,
- Another object is to provide a coupler for two-component diazotype photoprinting materials.
- FIGURE 1 is a sectional view of a diazotype photoprinting material of the present invention.
- Example 1 Diazotype base paper support with a precoat of colloidal silicic acid was coated with a solution containing g. 1-[2-din1ethylamino) -carbanilido] 3,5 dihydroxyin 100 cc. of water.
- the sensitized base paper was exposed to light under a transparent pencil drawing and afterwards developed with ammonia. High-contrast copies with bluish-red color and pure white background were obtained. When the copies were dabbed with water the dyestuff did not run, while the dyestuflf obtained by the use of the simple amide of the 3,5-dihydroxy-4 bromobenzoic acid bled out completely.
- the diazotization product from 1-piperidino-2,5-dimethoxy-4-aminobenzene can be used in combination with the compound of Formula III with equal success.
- the melting point was 17 6178 C.
- thionyl chloride e.g., 36.8 g. of diacetyl product with 75 cc. of thionyl chloride, for 2 to 2 /2 hours
- the chloride of acetylated 3,5-dihydroxy-4-bromobenzoic acid (diacetyl-bromo resorcylic acid chloride) was formed, this was isolated by vacuum distillation of the residual thionyl chloride. After purification with petroleum ether, the melting point was 108 C.
- the reaction mixture was heated for 15-20 minutes on the steam bath to 70-80 C. after 150 cc. of hydrochloric acid (about 18%) had been added.
- the resultant solution was filtered over charcoal and, after cooling, the filtrate was neutralized with about 20% sodium hydroxide.
- the resultant crystal slurry was the 1-[(2-dimethylamino)-carbani1ido]3,5 dihydroxy 4 bromo benzene (Formula III).
- the crystals were filtered off with suction, washed with water, and further purified by recrystallization from the smallest possible quantity of methanol.
- the purified product was colorless and melted at 222 C.
- Example 2 The procedure of Example 1 was followed but instead of the compound corresponding to Formula III the equiv alent quantity of the compound 1-[(2'-diethylamino)- carbanilido]-3,5-dihydroxy-4-bromo-benzene corresponding to Formula IV is used in the coating solution as coupler. From the photoprinting paper prepared therewith prints with violet red color Were obtained. The dyestutf was water-resistant. In comparison with commercially available photoprinting papers from which copies with red colors can be prepared, the paper prepared in accordance with this invention was characterized by considerably improved contrast.
- the 1- 2-dipropylamino -carbanilido] -3,5-dihydroxy-4- bromobenzene corresponding to Formula V or the 1-[ (3'- dimethylarnino)-carbanilido]-3,5 dihydroxy 4 bromobenzene corresponding to Formula VI can be used with equally good results with a slight color displacement to the red-violet in the lines of the prints.
- the compound corresponding to Formula IV can be prepared in analogous manner to that described in Example 1 for the compound with Formula III or it can be prepared as follows:
- Example 3 In the same manner as in Example 1, paper was coated with a solution containing g. 1-[(2'-dimethylamino)-carbanilido] 3,5 dihydroxy- 4-bromo-benzene corresponding to Formula III 2.0 Diazo compound from 1-dimethylamino-2,S-diethoxy- -amino-benzene (in the form of the zinc chloride double salt) 2.4 Citric acid 6.0 Thiourea 5.0
- the diazo compound from I-dimethylamino- 2,5-diethoxy-4amino-benzene instead of the diazo compound from 1-diethylamin0-2,S-diethoxy-4-amino-benzene or from 1- diethylamino-2,5-dimethoxy-4-amino-benzene, in the form of the zinc chloride double salts, can be used with equally good results.
- Example 4 In accordance with the instructions given in Example 1, diazotype base paper was coated with a solution which contained 2 g. of 1-[(4-diethylamino)-carbanilido]-3,5- dihydroxy-4-bromo-benzene corresponding to Formula VII or 2 g. of 1-[(4'-dimethylamino)-carbanilido]-3,5- dihydroxy-4-bromo-benzene corresponding to Formula VIII and 2.3 g. of the diazo compound from l-(N-methylpiperazino)-2,5-diethoxy-4-amino-benzene (in the form of the zinc chloride double salt).
- Example 5 In accordance with the instructions given in Example 1 and with the additives therein mentioned a solution was prepared which contained 2.1 g. of 1-[(3'-diethylamino- 4-methyl)-carbanilido]-3,5-dihydroxy 4 bromo-benzene corresponding to Formula IX and 2.2 g. of. the diazo compound from 1-morpholino-2,5-dibutoxy-4-amino benzene (in the form of the zinc chloride double salt) and Was coated upon diazotype base paper. When the sensitized paper was exposed to light under a transparent master and developed, prints were obtained with deep brownred lines.
- Example 6 diethoxy-4-amino-benzene (in the form of the zinc chloride double salt). This was applied to diazotype base paper and dried. The copies obtained by exposure to light under a master and development were of a more bluish red than the prints obtained in the previous examples.
- Example 7 For the preparation of a solution for the sensitization of diazotype base paper the procedure described in Example 1 was followed but 1.9 g. of 1-[ (4'-morpholino)- carbanilido] -3,S-dihydroxy-4-bromo-benzene correspond- HO OH i III-H Rs Y N
- R and R are alkyl of 1 to 3 carbon atoms or together with the nitrogen atom form (X) 'pyrrolidino, (X) -piperidino, (IX) -piperazino, (X) -morpholino or (X) -thiomorpholino wherein X is alkyl of1to2andnis0to3;and
- Y is a member selected from the group consisting of hydrogen, chloro and methyl.
- a compound according to claim 1 said compound being 1 [(2' diethylamino) carbanilido] 3,5 dihydroxy-4-bromo-benzene.
- a compound according to claim 1, said compound being 1 [(2. dipropylamino) carbanilido] 3,5 dihydroXy-4-bromo-benzene.
- a compound according to claim 1 said compound being 1 [(3 dimethylamino) carbanilido] 3,5 dihydroXy-4-bromo-benzene.
- a compound according to claim 1, said compound being 1 [(4' diethylamino) carbanilido] 3,5 dihydroxy-4-bromo-benzene.
- a compound according to claim 1, said compound being 1 [(4 dimethylamino) carbanilido] 3,5 dihydroXy-4-br0mo-benzene.
- a compound according to claim 1 said compound being 1 [(3 diethylamino 4 methyl) carbanilido1- 3,5-dihydroXy-4-bromo-benzene.
- a compound according to claim 1 said compound being 1 [(4 diethylamino -3' chloro) carbanilido]- 3,5-dihydroXy-4-bromo-benzene.
- a compound according to claim 1 said compound being 1 [(4 morpholino) carbanilido] 3,5 dihydroXy-4-bromo-benzene.
Description
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US440982A US3337549A (en) | 1962-11-08 | 1965-02-10 | 1-[tertiary amino-carbanilido]-3, 5-dihydroxy-4-bromo benzenes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US236191A US3186845A (en) | 1961-11-11 | 1962-11-08 | Two-component diazotype material |
US440982A US3337549A (en) | 1962-11-08 | 1965-02-10 | 1-[tertiary amino-carbanilido]-3, 5-dihydroxy-4-bromo benzenes |
Publications (1)
Publication Number | Publication Date |
---|---|
US3337549A true US3337549A (en) | 1967-08-22 |
Family
ID=26929535
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US440982A Expired - Lifetime US3337549A (en) | 1962-11-08 | 1965-02-10 | 1-[tertiary amino-carbanilido]-3, 5-dihydroxy-4-bromo benzenes |
Country Status (1)
Country | Link |
---|---|
US (1) | US3337549A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05345738A (en) * | 1983-12-21 | 1993-12-27 | Fidia Spa | Halogenoresorcin derivative |
-
1965
- 1965-02-10 US US440982A patent/US3337549A/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
None * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05345738A (en) * | 1983-12-21 | 1993-12-27 | Fidia Spa | Halogenoresorcin derivative |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2859112A (en) | Quinoline-quinone-(3, 4) diazide plates | |
US2672417A (en) | Production of color photographic images | |
US3028240A (en) | Light sensitive diazotype materials | |
US2459226A (en) | Production of pyrazole-5-ones | |
US3186845A (en) | Two-component diazotype material | |
US3171740A (en) | Process for the production of colored photographic non-transparent or transparent images | |
US2846307A (en) | Isoxazolone couplers in color photography | |
US2277409A (en) | Chemical composition | |
US3337549A (en) | 1-[tertiary amino-carbanilido]-3, 5-dihydroxy-4-bromo benzenes | |
US4492749A (en) | Diazotype materials with 2-hydroxy-naphthalene having sulfonamide substituent as coupler | |
US4334004A (en) | Light-sensitive diazotype material with 2-hydroxy-3-naphthoic acid amides having 6-sulfonic acid amide substitution | |
US3432301A (en) | Reproduction material | |
US2665985A (en) | Light-sensitive diazo compounds and photoprint material prepared therefrom | |
US2930694A (en) | Optical sensitization of direct positive emulsions | |
US4174221A (en) | Yellow 2:1 chrome complexed dye developers | |
US3255010A (en) | Two-component diazotype material | |
US2946684A (en) | Diazotype copying processes | |
US2150565A (en) | Production of diazo prints | |
US3639421A (en) | Diazotype materials | |
US2899443A (en) | Process of preparing certain halogen- | |
US2618641A (en) | Arylidene-bis-pyrazolones | |
US3281246A (en) | Diazotype reproduction material | |
US3429900A (en) | Stable triphenyl-methane dye leucos | |
US3970460A (en) | Diazotype composition | |
US2705713A (en) | Production of cyanine dyestuffs |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: SECURITY NATIONAL BANK, A NATIONAL BANKING ASSOCIA Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 Owner name: CHASE MANHATTAN BANK, N.A. THE; A NATIONAL BANKING Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 Owner name: CHEMICAL BANK, A BANKING INSTITUTION OF NY. Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 Owner name: CONTINENTAL ILLINOIS NATIONAL BANK & TRUST CO., OF Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 Owner name: BANK OF CALIFORNIA N.A. THE; A NATIONAL BANKING AS Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 Owner name: CHEMICAL BANK, A BANKING INSTITUTION OF, NEW YORK Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 |