GB990971A - Permanent reproductions and their preparation - Google Patents
Permanent reproductions and their preparationInfo
- Publication number
- GB990971A GB990971A GB14060/61A GB1406061A GB990971A GB 990971 A GB990971 A GB 990971A GB 14060/61 A GB14060/61 A GB 14060/61A GB 1406061 A GB1406061 A GB 1406061A GB 990971 A GB990971 A GB 990971A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dye
- formula
- prepared
- tetramethylthiourea
- reacting
- 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
- 230000033458 reproduction Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 9
- 239000000987 azo dye Substances 0.000 abstract 8
- 239000000975 dye Substances 0.000 abstract 8
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical class [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 abstract 2
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-UHFFFAOYSA-N 0.000 abstract 1
- ZJKASTDHVMFBIE-UHFFFAOYSA-N 1-(4-aminophenyl)ethanone;sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O.CC(=O)C1=CC=C(N)C=C1 ZJKASTDHVMFBIE-UHFFFAOYSA-N 0.000 abstract 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 abstract 1
- BJTQKRCFMBXXIJ-UHFFFAOYSA-N 2-(chloromethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1CCl BJTQKRCFMBXXIJ-UHFFFAOYSA-N 0.000 abstract 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 abstract 1
- XRZDIHADHZSFBB-UHFFFAOYSA-N 3-oxo-n,3-diphenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)C1=CC=CC=C1 XRZDIHADHZSFBB-UHFFFAOYSA-N 0.000 abstract 1
- YQUWPZHFELAURW-UHFFFAOYSA-N 4-(chloromethyl)-N-tetradecylbenzenesulfonamide Chemical compound C(CCCCCCCCCCCCC)NS(=O)(=O)C1=CC=C(C=C1)CCl YQUWPZHFELAURW-UHFFFAOYSA-N 0.000 abstract 1
- JXVJGPMIPPKYAS-UHFFFAOYSA-N 4-(chloromethyl)benzenesulfonyl chloride Chemical compound ClCC1=CC=C(S(Cl)(=O)=O)C=C1 JXVJGPMIPPKYAS-UHFFFAOYSA-N 0.000 abstract 1
- RCOVTJVRTZGSBP-UHFFFAOYSA-N 4-(chloromethyl)benzoyl chloride Chemical compound ClCC1=CC=C(C(Cl)=O)C=C1 RCOVTJVRTZGSBP-UHFFFAOYSA-N 0.000 abstract 1
- NHWQHAUDYCYZMY-UHFFFAOYSA-N 4-amino-N-tetradecylbenzenesulfonamide Chemical compound CCCCCCCCCCCCCCNS(=O)(=O)C1=CC=C(N)C=C1 NHWQHAUDYCYZMY-UHFFFAOYSA-N 0.000 abstract 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 abstract 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 abstract 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 150000001412 amines Chemical class 0.000 abstract 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 abstract 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 abstract 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 abstract 1
- 235000011056 potassium acetate Nutrition 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/12—Recording members for multicolour processes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G13/00—Electrographic processes using a charge pattern
- G03G13/01—Electrographic processes using a charge pattern for multicoloured copies
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G13/00—Electrographic processes using a charge pattern
- G03G13/26—Electrographic processes using a charge pattern for the production of printing plates for non-xerographic printing processes
- G03G13/28—Planographic printing plates
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G17/00—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process
- G03G17/02—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process with electrolytic development
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0525—Coating methods
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/09—Sensitisors or activators, e.g. dyestuffs
Abstract
Thiourmium salt of N-tetradecyl-p chloromethylbenzenesulphonamide is prepared by reacting tetradecylamine with p-chloromethylbenzene-sulphonyl chloride in alcoholic solution containing potassium acetate to give N - tetradecyl - p - chloromethylbenzenesulphonamide. This is reacted with N,N,N1,N1-tetramethylthiourea to give the thiouronium salt. The thiouronium salt of formula IIIE <FORM:0990971/C2/1> is prepared by reacting cyanuric chloride with N1 - tetradecylsulphanilamide in cold acetone with sodium carbonate present and reacting the product with N,N,N1,N1-tetramethylthiourea. Specifications 864,474, 864,475 and 963,433 are referred to.ALSO:Thiouronium salt of an azo dye of formula IB2 <FORM:0990971/C4-C5/1> is prepared by coupling Naphthol AS-LG (C.I. 37615) and Fast Red Salt FRN (C.I. 37075). This compound is dissolved in sulphuric acid, chloromethyl methyl ether added and heated. This chloromethylated compound is heated with N,N,N1,N1-tetramethylthiourea to give the azo dye. Thiouronium salt of a dye of formula IB3 <FORM:0990971/C4-C5/2> is prepared by chloromethylating Indigo Yellow (C.I. 73100) in sulphuric acid with bis(chloromethyl) ether. The product is added to molten N,N,N1,N1-tetramethylthiourea and heated to give the azo dye. An azo dye is prepared by coupling the benzoylacetanilide produced by condensation of ethyl benzoyl-acetate and 2,5-dimethoxyaniline with the diazo compound obtained from the amine which is produced by condensing p-acetyl-aminobenzene sulphonyl chloride with N,N-diethyl-ethylenediamine followed by hydrolysis of the acetyl group. This dye is reacted with phenacyl bromide in alkali to give the dye of the formula IB4(a) <FORM:0990971/C4-C5/3> Alternatively the azo dye may be reacted with bis(chloro-methyl) ether in acid and this product reacted with N,N,N1,N1-tetramethylthiourea to give a dye of formula IB4(b) <FORM:0990971/C4-C5/4> A thiouronium salt of dye of formula IC1 <FORM:0990971/C4-C5/5> is prepared by reacting Basolan Chrome Brilliant Red 3BM with thionyl chloride and then reacting the chlorinated product with p-nitro-aniline. This nitro compound is reduced with iron and reacted with chloracetyl chloride. This product is reacted with N,N,N1,N1-tetramethylthiourea to give the dye of the formula Thiouronium salt of a dye of formula IC2 <FORM:0990971/C4-C5/6> is prepared by chloromethylating Anthrogen Red Violet RHC (C.I. 73385) and reacting with N,N,N1,N1-tetramethylthiourea. Similarly the thiouronium salt of Naphthol AS azo dye of formula II <FORM:0990971/C4-C5/7> is prepared from the azo dye. The azo dye of formula III A <FORM:0990971/C4-C5/8> is prepared by reacting Naphthol AS-LG (C.I. 37615) with Fast Red Salt ITRN (C.I. 37150). The thiouronium salt of the dye of formula III F <FORM:0990971/C4-C5/9> is prepared by refluxing p-chloromethylbenzoyl chloride and 1,5-diamino-anthraquinone and then reacting with N,N,N1,N1-tetramethylthiourea. Specifications 864,474, 864,475 and 963,433 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2293160A | 1960-04-18 | 1960-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB990971A true GB990971A (en) | 1965-05-05 |
Family
ID=21812164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14060/61A Expired GB990971A (en) | 1960-04-18 | 1961-04-18 | Permanent reproductions and their preparation |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3172826A (en) |
| BE (1) | BE602732A (en) |
| CH (1) | CH415301A (en) |
| DK (1) | DK105632C (en) |
| ES (1) | ES266308A1 (en) |
| GB (1) | GB990971A (en) |
| NL (1) | NL263728A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3436321A (en) * | 1966-09-13 | 1969-04-01 | Minnesota Mining & Mfg | Developer compositions and their use in electrolytic electrophotography |
| US4002475A (en) * | 1975-05-05 | 1977-01-11 | Eastman Kodak Company | Photoconductive process for making electrographic masters |
| US6194108B1 (en) * | 1996-10-17 | 2001-02-27 | Fuji Xerox Co., Ltd. | Image forming method and image forming device using same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2297691A (en) * | 1939-04-04 | 1942-10-06 | Chester F Carlson | Electrophotography |
| US2874101A (en) * | 1952-09-17 | 1959-02-17 | Farnsworth Res Corp | Method of making double-sided mosaic |
| US2862816A (en) * | 1954-03-26 | 1958-12-02 | Rca Corp | Method of and means for reducing triboelectric forces in electrophotography |
| US2857271A (en) * | 1954-09-28 | 1958-10-21 | Rca Corp | Electrostatic printing process for producing photographic transparencies |
| US2854386A (en) * | 1955-02-07 | 1958-09-30 | Aladdin Ind Inc | Method of photographically printing conductive metallic patterns |
| US2955035A (en) * | 1956-01-03 | 1960-10-04 | Haloid Xerox Inc | Raised xerographic images |
| BE561403A (en) * | 1956-03-30 |
-
0
- US US3172826D patent/US3172826A/en not_active Expired - Lifetime
- NL NL263728D patent/NL263728A/xx unknown
-
1961
- 1961-04-05 ES ES0266308A patent/ES266308A1/en not_active Expired
- 1961-04-17 CH CH452061A patent/CH415301A/en unknown
- 1961-04-17 DK DK156661AA patent/DK105632C/en active
- 1961-04-18 GB GB14060/61A patent/GB990971A/en not_active Expired
- 1961-04-18 BE BE602732A patent/BE602732A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK105632C (en) | 1966-10-17 |
| ES266308A1 (en) | 1961-12-01 |
| NL263728A (en) | |
| BE602732A (en) | 1961-10-18 |
| US3172826A (en) | 1965-03-09 |
| CH415301A (en) | 1966-06-15 |
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