US3416925A - Diazotype reproduction material - Google Patents

Diazotype reproduction material Download PDF

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Publication number
US3416925A
US3416925A US380126A US38012664A US3416925A US 3416925 A US3416925 A US 3416925A US 380126 A US380126 A US 380126A US 38012664 A US38012664 A US 38012664A US 3416925 A US3416925 A US 3416925A
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United States
Prior art keywords
chloride
diazonium
dimethylamino
methoxy
benzene
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Expired - Lifetime
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US380126A
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English (en)
Inventor
Sus Oskar
Schafer Heinz
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Keuffel and Esser Co
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Keuffel and Esser Co
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Assigned to CONTINENTAL ILLINOIS NATIONAL BANK & TRUST CO., OF CHICAGO, A NATIONAL BANKING ASSOCIATION, BANK OF CALIFORNIA N.A. THE; A NATIONAL BANKING ASSOCIATION, CHASE MANHATTAN BANK, N.A. THE; A NATIONAL BANKING ASSOCIATION, SECURITY NATIONAL BANK, A NATIONAL BANKING ASSOCIATION FOR ITSELF AND AS AGENT FOR CITIBANK, N.A. A NATIONAL BANKING ASSOCIATION, CHEMICAL BANK, A BANKING INSTITUTION OF reassignment CONTINENTAL ILLINOIS NATIONAL BANK & TRUST CO., OF CHICAGO, A NATIONAL BANKING ASSOCIATION SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KEUFFEL & ESSER COMPANY A.N.J. CORP
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/54—Diazonium salts or diazo anhydrides

Definitions

  • the present invention relates to reproduction materials, more particularly referring to the diazotype reproduction materials and diazonium compounds for use thereon.
  • diazo compounds derivatives of the unilaterally diazotized p phenylene diamine are used among other basic diazo compounds as light-sensitive substances for the preparation of reproduction coatings.
  • These diazo compounds have attained great technical importance for the so-called dry-development process, as well as for the socalled semi-dry process.
  • diazo compounds containing alkyl groups with a low number of carbon atoms on the basic nitrogen atom are particularly well-suited for the dry-development process, whereas the compounds having groups with long-chain or cyclic hydrocarbon radicals on the nitrogen atom are suitable for the semi-dry process.
  • the hue of the 'dyestuff obtainable through coupling with the azo components known for diazotype processes is influenced through substitution on the nitrogen atom.
  • the light sensitivity and stability of the diazo compounds or rather of the light-sensitive coatings prepared therefrom can also be influenced by variation of the substituents on the nitrogen atom.
  • the above-mentioned properties of the p-amino-diazo compounds can be influenced to an even stronger degree through substituents in the benzene ring carrying the diazo group.
  • a substituent in ortho position to the diazo group such as a methyl, methoxy, or carboxylic acid group causes a considerable increase in stability, and also a shift in hue toward the blue, whereas the light-sensitive property is decreased.
  • an alkoxy group is introduced in meta-position to the diazo group, the diazo compound is substantially more light sensitive as compared with the unsubstituted compound, but the stability is decreased.
  • this group of diazo compounds has a cetrain technical importance in view of its high light sensitivity, for example, for producing quick copies of letter originals merely for information purposes.
  • the stability of the diazo molecules can be improved by introducing a substituent, such as alkyl, alkoxy, or halogen, in the ortho-position to the alkoxy group which in turn is in the meta-position in relation to the diazo group, and that the high light sensitivity of the type of p-amino diazo compound characterized by an alkoxy group in the meta-position is not essentially alfected.
  • a substituent such as alkyl, alkoxy, or halogen
  • one object of the present invention is to provide diazonium compounds having improved light sensitivity and improved stability.
  • Another object is to provide methods for preparing diazonium compounds having improved light sensitivity and improved stability.
  • Another object is to provide a diazotype reproduction material having thereon a diazonium compound of improved light sensitivity and improved stability.
  • Diazotype reproduction materials comprise a support, such as paper, other cellulose material, cellulose derivatives, or plastic material, having as the light-sensitive substance a diazonium salt according to the general formula:
  • R and R are members selected from one of the two groups consisting of:
  • R and R are members selected from one of the two groups consisting of:
  • R is alkyl and R is a member selected from the group consisting of alkyl, alkoxy, and halogen, and
  • X is the anion of the diazonium salt.
  • R R R and R represent the above mentioned groups, in acid solution with nitrous acid and precipitating them as salts, or, if desired, as double salts with the aid of a salt of a heavy metal.
  • the above mentioned 2,3-substituted para-aminodiazo compounds in which R, and R are alkyl groups, R is an alkyl group and R is an alkoxy group, alkyl group, or a halogen may be prepared from -amino-l-alkoxybenzene, which is substituted in the 2-position by an alkoxyalkyl, or halogen group by di-alkylating the amino group, for example, with dirnethyl sulphate, then by providing the obtained tertiary amino compound with an azo group in the para-position to the tertiary amino group by coupling with a diazo compound, then by finally changing this into an amino group by reduction.
  • the sensitized paper was exposed imagewise and developed according to the semi-dry process, using the following developer:
  • Example 2 A photocopying base paper g./s.m.) was coated with the following solution:
  • diazo compound according to Formula 2 l-methoxy 2 methyl-6-dimethylamino-benzene-3-diazonium chloride (cadmium chloride double salt), was prepared as follows:
  • the reduction of the dyestutf to the amine was effected catalytically with the aid of nickel. After evaporation of the solvent, the oily residue was agitated with water, thereby dissolving the separated p-phenylene-diamine.
  • the Z-methyl-3-amino-6-dimethylamino-anisole remained as a water insoluble oil. Its boiling point was 153155 C. at 15 torr.
  • the amine was diazotized in hydrochloric acid with a 2 N sodium nitrite solution.
  • the diazo compound was precipitated as a cadmium chloride double salt. It crystallized with one half mol of cadmium chloride. Its decomposition point was 126 C.
  • the diazo compound according to Formula 5 the 1- methyl 2 methoxy-3-morpholino-benzene-6-diazoniumhexafluoro-phosphate, was prepared as follows:
  • the base was converted into 3-morpholino-1-amino-2-rnethoxy-toluene having a melting point of 130 C.
  • Diazotization was carried out conventionally in a hydrochloric solution.
  • the diazo compound was precipitated as a salt of the hexahydrofluorophosphoric acid. It melted and decomposed at 129 C.
  • Example 3 The following solution was applied to paper and dried.
  • diazo compound according to Formula 3 1,2-dimethoxy-3-dimethylamino-benzene-6-diaz0nium chloride (stannic chloride double salt), was prepared as follows:
  • 3-arninoveratrole was converted into 3-dimethylaminoveratrole by dialkylation with dimethyl sulphate in the presence of sodium bicarbonate in a methanol-water mixture between 210 C.
  • the base thus obtained was an oil with a boiling point of 107-109 C. at 9 torr.
  • the azo dyestuff 6-(4-nitrophenyl-azo)-3-dimethylaminoveratrole was produced by coupling the base with diazotized p-nitroaniline. The dyestuif melted at 120-121 C.
  • the reduction of the dye to the amine was effected catalytically with the aid of nickel in a solvent. After evaporation of the solvent, the oily residue was agitated with water. The 6-amino-3-dimethylaminoveratrole remained as a water-insoluble oil. It boiled at 161 C. under a pressure of 14 torr.
  • Diazotization was carried out conventionally in hydrochloric acid with a 2 N sodium nitrite solution.
  • the diazo compound was precipitated as a tin tetrachloride double salt. It crystallized with one half mol stannic chloride. Decomposition point: 139 C.
  • Example 4 A photocopying base paper was provided with a lightsensitive coating prepared according to the following formula:
  • the diazo compound according to Formula 4 the l-ethoxy 2 methoxy 6 dimethylamino benzene 3- diazonium chloride (tin tetrachloride double salt), was prepared as follows:
  • 3nitro-2-hydroxy-anisole was ethylated to 3-nitro-2 ethoxyanisole with diethyl sulfate in alkaline solution.
  • I was obtained as a yellow oil with a boiling point of 162- 164 C. (10 torr). It was converted into 3-arnino-2 ethoxy-anisole by catalytic reduction. Boiling point: 134- 136 C. (9 torr).
  • This base was dimethylated with dimethyl sulfate ii the presence of sodium hydrogen carbonate in a methanol-water mixture between 420 C.
  • the 3-dimethyl amino-2-ethoxy-anisole boiled at C. (8 mm.).
  • Diazotization was carried out conventionally in the hydrochloric acid with a 40% sodium nitrite solution.
  • the diazo compound crystallized with one half mol stannic chloride. Its decomposition point was 140 C.
  • Example 5 A photocopying base paper was coated with the following solution:
  • the diazo compound according to Formula 6 the 5 dimethylamino-benzodioxane 8 diazonium chloride (cadmium chloride double salt) was prepared as follows:
  • the obtained amino compound was diazotized in hydrochloric acid solution with a 40% sodium nitrite solution.
  • the diazo compound was precipitated from the solution as the cadmium chloride double salt. It crystallized with one half mol cadmium chloride. It decomposition point was C.
  • R and R are lower alkyl groups, or are members of the same morpholino heterocyclic ring;
  • R is a lower alkyl;
  • R; is a lower alkyl, lower alkoxy, or halogen, or R and R are members of the same dioxane ring, and
  • X is the anion of the diazonium salt.
  • a photosensitive diazonium compound selected from the group consisting of:
  • a diazotype reproduction material comprising a support and a photosensitive diazonium compound having the general formula:
  • R and R are lower alkyl groups, or members of the same morpholino heterocyclic ring;
  • R is a lower alkyl;
  • R; is a lower alkyl, lower alkoxy, or halogen, or R and R are members of the same dioxane ring; and
  • X is the anion of the diazonium salt.
  • a diazotype reproduction material comprising a support having a layer containing a photosensitive diazonium compound selected from the group consisting of:
  • a diazotype reproduction material comprising a support having a layer containing the photosensitive diazo compound 1-methoxy-2-chloro-6-dimethylamino-bcnzene- 3-diazonium chloride, cadmium chloride double salt.
  • a diazotype reproduction material comprising the support having a layer containing a photosensitive diazonium compound 1-methoxy-2-methyl-6-dimethylaminobenzene-3diazonium chloride, cadmium chloride double salt.
  • a diazotype reproduction material Comprising a support having a layer containing the photosensitive diazonium compound 1,2-dimethoxy-3-dimethylamino-benzene-6-diazonium chloride, stannic chloride double salt.
  • a diazotype reproduction material comprising a support having a layer containing the photosensitive diazoniumcompound l-ethoxy-2-methoXy-6-dimethylaminobenzene-3-diazonium chloride, tin tetrachloride double salt.
  • a diazotype reproduction material comprising the support having a layer containing a photosensitive diazonium compound 1-methyl-2-methoxy-3-morpholin0-benzene-6-diazonium-hexafluorophosphate.
  • a diazotype reproduction material comprising a support having a layer containing the photosensitive diazonium compound S-dimethylamino-benzodioxane-8-diazonium chloride, cadmium chloride double salt.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US380126A 1963-07-06 1964-07-03 Diazotype reproduction material Expired - Lifetime US3416925A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEK0050151 1963-07-06

Publications (1)

Publication Number Publication Date
US3416925A true US3416925A (en) 1968-12-17

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Country Status (7)

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US (1) US3416925A (enrdf_load_stackoverflow)
AT (1) AT250777B (enrdf_load_stackoverflow)
BE (1) BE650109A (enrdf_load_stackoverflow)
CH (1) CH439961A (enrdf_load_stackoverflow)
GB (1) GB1005899A (enrdf_load_stackoverflow)
NL (1) NL140992B (enrdf_load_stackoverflow)
SE (1) SE326369B (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3868255A (en) * 1969-07-23 1975-02-25 Gaf Corp Diazonium salts and diazotype materials
US20060160845A1 (en) * 2005-01-10 2006-07-20 Nathalie Schlienger Aminophenyl derivatives as selective androgen receptor modulators
US20060173037A1 (en) * 2005-01-10 2006-08-03 Nathalie Schlienger Aminophenyl derivatives as selective androgen receptor modulators
US20070004679A1 (en) * 2004-05-17 2007-01-04 Nathalie Schlienger Androgen receptor modulators and methods of treating disease using the same
US20080009489A1 (en) * 2004-05-17 2008-01-10 Acadian Pharmaceuticals, Inc. Androgen receptor modulators and method of treating disease using the same

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL128326C (enrdf_load_stackoverflow) * 1965-03-12
NL130247C (enrdf_load_stackoverflow) * 1965-03-12
NL128126C (enrdf_load_stackoverflow) * 1965-03-24
NL132069C (enrdf_load_stackoverflow) * 1965-07-02
DE3913477A1 (de) * 1989-04-24 1990-10-25 Henkel Kgaa Haarfaerbemittel

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1840333A (en) * 1927-07-21 1932-01-12 Kalle & Co Ag Solid stable diazo compounds and process of preparing them
US2405523A (en) * 1944-08-09 1946-08-06 Du Pont Light-sensitive photographic compositions and elements
GB867630A (en) * 1958-06-04 1961-05-10 Grinten Chem L V D Diazotype material
US2990281A (en) * 1956-12-17 1961-06-27 Monsanto Chemicals Photosensitive resinous compositions and photographic elements
US3113022A (en) * 1959-02-26 1963-12-03 Gevaert Photo Prod Nv Electrophotographic process

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1840333A (en) * 1927-07-21 1932-01-12 Kalle & Co Ag Solid stable diazo compounds and process of preparing them
US2405523A (en) * 1944-08-09 1946-08-06 Du Pont Light-sensitive photographic compositions and elements
US2990281A (en) * 1956-12-17 1961-06-27 Monsanto Chemicals Photosensitive resinous compositions and photographic elements
GB867630A (en) * 1958-06-04 1961-05-10 Grinten Chem L V D Diazotype material
US3113022A (en) * 1959-02-26 1963-12-03 Gevaert Photo Prod Nv Electrophotographic process

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3868255A (en) * 1969-07-23 1975-02-25 Gaf Corp Diazonium salts and diazotype materials
US20070004679A1 (en) * 2004-05-17 2007-01-04 Nathalie Schlienger Androgen receptor modulators and methods of treating disease using the same
US20080009489A1 (en) * 2004-05-17 2008-01-10 Acadian Pharmaceuticals, Inc. Androgen receptor modulators and method of treating disease using the same
US20060160845A1 (en) * 2005-01-10 2006-07-20 Nathalie Schlienger Aminophenyl derivatives as selective androgen receptor modulators
US20060173037A1 (en) * 2005-01-10 2006-08-03 Nathalie Schlienger Aminophenyl derivatives as selective androgen receptor modulators
US7585877B2 (en) 2005-01-10 2009-09-08 Acadia Pharmaceuticals, Inc. Aminophenyl derivatives as selective androgen receptor modulators

Also Published As

Publication number Publication date
BE650109A (enrdf_load_stackoverflow) 1965-01-04
GB1005899A (en) 1965-09-29
NL6407303A (enrdf_load_stackoverflow) 1965-01-07
CH439961A (de) 1967-07-15
NL140992B (nl) 1974-01-15
SE326369B (enrdf_load_stackoverflow) 1970-07-20
DE1693195B2 (de) 1976-05-26
AT250777B (de) 1966-11-25
DE1693195A1 (de) 1971-08-12

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