US2537001A - Diazotype layers having cyan acetyl amides as azo components - Google Patents
Diazotype layers having cyan acetyl amides as azo components Download PDFInfo
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- US2537001A US2537001A US766875A US76687547A US2537001A US 2537001 A US2537001 A US 2537001A US 766875 A US766875 A US 766875A US 76687547 A US76687547 A US 76687547A US 2537001 A US2537001 A US 2537001A
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- diazotype
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- azo
- light
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- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title 1
- 239000000463 material Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims 1
- 238000000576 coating method Methods 0.000 description 14
- 150000008049 diazo compounds Chemical class 0.000 description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 239000012954 diazonium Substances 0.000 description 11
- 230000007704 transition Effects 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 230000033458 reproduction Effects 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 150000001555 benzenes Chemical class 0.000 description 6
- 239000008199 coating composition Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000238370 Sepia Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 3
- -1 diazo anhydrides Chemical class 0.000 description 3
- 239000003517 fume Substances 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 2
- 229960001553 phloroglucinol Drugs 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical class COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- XOBAIYPLCUTNFV-UHFFFAOYSA-N 4-n,2-dimethylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C(C)=C1 XOBAIYPLCUTNFV-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
Classifications
-
- 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
- G03C1/58—Coupling substances therefor
Definitions
- This invention relates to a diazotype process and more. particularly to the use of organic esters and. nitriles. containing active methylene group as the azo components in the light. sensitive layer of. a diazotypereproduction' medium min a: developing solution for the exposed diazotype image.
- the diazo compound development is effected by passing. the exposed diazotype. through am.- monia vapors, and where. a. one-componentsystem is employed which containsthe diazo come poundv as the only dye component in the light sensitive layer, the image is. developed. by treator'valuable originalwhicl'iz wouldfbeadversely af;- fected, if not destroyed, in the repeatediexposures necessary to make the deslred'number of" copies.
- print depends. upon the opacityof the azo. dye? ing half-tones or too lightlines theydo not proimage produced "upon. such'intermediateor transi.- tion' print to ultraviolet li'ghtta'nd upon .the transparency offthe. background t'oz. such light. It. die.- pen'ds also; upon the visual density of. the. image. produced on the: intermediate-yer transitionv print; since'image's oi.poorivi'sual. ;iinz;.suoh.as li'ghtl. yeilow's; on: a white or: transparent: background',..
- The-azo: dye. component used for the production of transition print images must be such as to producerupomcouplingawith the:
- diazo compound employed a color which will sufficiently absorb the ultraviolet lightinc'ident upon it during exposureto'prevent light-decomposition of the diazo compound in the-areas to-be repro h cuted fromthetransition copies. Colors of good visual density do notneeessarilyhave this property. It is well'known, for instance, that blues, such as" are produced from azo components like phloroglucin, are-very poor in their ultraviolet absorption characteristics.
- Azo component's, sueh-asresorcinol, have heretofore been employed in the production of diazotype prints in order to obtain color images having the necessary light absorption characteristics for transition printing.
- Resorcinoliwill reproduce the:imageron,the:transition print in a sepia or orange-brown color which has good opacity to ultraviolet light and has" sufiicient depth of color orvisualZ-d'ensity to assure detec- 40 tion oi printing flaws and the like in the devel- Other azo components,
- cyanacetylamides containing an active methylene group are especially effective as azo components for di azotype reproduction.
- These cyanacetylamides containing active methylene groups may be represented by the formula lene or Z S-dihydroXynaphthalene sulfonic acid,
- cyanacetylamides having active methylene groups of this class are Cyanacetamide f i 2. Cyanacetanilide err-omoo-nnQ 3. p-I-Iydroxy cyanacetanilide 4. Cyanacetbenzylamide 5. l-1nethyl-2w-cyanacetyliminodihydroquinoline.
- Cyanacetylguanidine I v oN-o Hio o-NH-c-Nm 9.
- Cyanacetylcyanamide CNCH2CONHCN 10.
- Cyanacetylethylurethane cn-onzco-mncoocgml 11. 1 w cyanacetylimino 2 methyl-E-ethoxydihydrobenzothiazole Y
- a suitable transparent base such as transparentized paper, cellulose acetate film or other transparent material, iscoatedby means known to the art with a light sensitive composition containing suitable diazo compounds.
- the azo component is also incorporated into the coating composition.
- the azo component is added to an alkaline developing solution and after exposure of the diazotype, the exposed image is developed by contacting with the alkaline developing solution by means known to the art.
- the coating solution may also contain such other materials as are ordinarily used in the preparation of diazotype twoeoinponent light sensitive coating compositions.
- stabilizing materials such as citric acid, phosphoric acid and thiourea
- swelling agents for cellulose acetate and other cellulosic ester bases such as isopropanol
- shade intensifying agents such as nickel sulfate.
- a two-component coating composition which will contain one or more dark tone producing azo components, preferably such as will produce blue shades with the diazo compounds employed in combination with the nitrile acetyl, amide azo components of this invention.
- any suitable light sensitive diazo compound which will couple with the azo components to reproduce a colored image may be employed.
- diazo compounds derived from p-diamines of the bon zene series particularly when two-component coating compositions are employed.
- this class of diazo compounds is especiall suitable for the production of twocomponent diazotype photosensitized papers.
- diazo compounds have been found suitable for use, such as diazo anhydrides of aminohyethyl N-ethylaminoA aminobenzene p phe'riyl- 4-ami-no-N,:N-dihydroxyethylaniene :diamine: line; p- (4 -ethoxyphenyl) -.a'm'ino -i2,'5-diethoxyaniline; 1-N-ethylamino-2-methyl-4-aminoben zene; 1-dimethyl-amino-3-methoxy-4-aminobenacne; N;N-dimethyam'ino-p-aminobenzenej 1-'d 'i-" methylamin-o 3 methyl-4-aminobenzene-; -'p-' .aminophenyl morpholine and 2-amino-1-naph- 'thol-S-Sulfon-ic acid.
- -"-*irans parentized paper is coated with a coating solution containing the following ingredients per 100 cc. of water containing 5% of alcohol:
- the print therefore, can be :used as :a transition or intermediate print for the reproduction of further diazotype copies or other photo -reproductions.
- diazotype materials having the same properties and reproducing the original in images of the same color as above are obtained.
- Example A diazotype---co.ating solution containingthefollowingaingredients per 1-00 cc. of a 5% aqueous solution of alcohol is made up:
- Example 5 Transparentized diazotype paper stock is coated with a coating solution containing the following ingredients per 100 cc. of water containing 5% of alcohol:
- the resulting coated paper or diazotype material has good precoupling stability during prolonged storage. After drying the coating in the usual manner, the diazotype is exposed to light under a pattern or other original to be reproduced and the image is developed with ammonia fumes. The image of the original is thus obtained in a sepia colored positive print. The dye or color areas reproducing the density areas of the original have good fade and wash-fastness properties and excellent capacity to ultraviolet light. The print, therefore, can be used as a transition or intermediate print for the reproduction of further diazotype copies or other photoreproductions.
- a diazotype photoprinting material comprising a light sensitive diazonium salt of a p-diamine of. the benzene series and as an azo component cyanacetanilide having the structural formula 3.
- a diazotype photoprinting material comprising a light sensitive diazonium salt of a p-diamine of the benzene series and as an azo component cyanacetylurea having the structural formula 4.
- a diazotype photoprinting material comprising a light sensitive diazonium salt of a p-diamine of th benzene series and as an azo component cyanacetbenzylamide having the structural formula ON-CHzC ONHCHT 5.
- a diazotype photoprintlng material comprising a light sensitive diazonium salt of a p-diamine of the benzene series and as an azo component cyanacetamide having the structural formula 6.
- a diazotype photoprinting material comprising a light sensitive diazonium salt of a p-diamine of the benzene series and as an azo component cyanacetylthiourea having the structural formula WILLIAM H. VON GLAI-IN. LESTER N. STANLEY.
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- Chemical & Material Sciences (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)
Description
Patented Jan. 2, 1 951 UNITED STATES DIAZOTYPE LAYERS HAVING CYAN'AGETYIJ AMIDES AS AZO COMPONENTS William H..von Glahn, Loudonville, and Lester N. Stanley, Delmar,.-N. Y., assignors to Generazb Aniline & Film Corporation,.New. York Nr-Y a corporation of Delaware.
No. Drawing. Application Au SerialNo. 766,875
6" Claims.
This invention relates toa diazotype process and more. particularly to the use of organic esters and. nitriles. containing active methylene group as the azo components in the light. sensitive layer of. a diazotypereproduction' medium min a: developing solution for the exposed diazotype image.
Inv the reproduction of mechanical drawings, printed material, pictures or other originals to be copied, it is of particular advantage in many cases to make first an intermediate print or transition print on a transparentdiazotypev copying material by exposingthe. transparent sensitized. diazotype material. to actinicrays, such as. ultra. violet light; by either. the. printing through. 01'. reflex process andithen developing the'diazotype material. The development of. such diazotype prints may be carried out-by any of the develop.-
ing methods known to the artrfor development" ofv exposed diazoty-pe materials. Thus,. where a. two-component: system is employed containing. the azo component in. the. light sensitivelayer.
with the diazo compound; development is effected by passing. the exposed diazotype. through am.- monia vapors, and where. a. one-componentsystem is employed which containsthe diazo come poundv as the only dye component in the light sensitive layer, the image is. developed. by treator'valuable originalwhicl'iz wouldfbeadversely af;- fected, if not destroyed, in the repeatediexposures necessary to make the deslred'number of" copies.
It is essential inthe so-called reflex process; where; i
Q such'as phloroglucinol andaresorcinol... Thesesazo. components are acetoacetyl" derivatives ofmonothe diazotype copy material"v is superimposed on the opaque original to be copied and" the. light. for exposure of the diazotype' material passes through; it and is reflected. by the surface oithe. original.-'- The efii'ciency. ofithe; processinvolving the production of a transition or intermediate.
print depends. upon the opacityof the azo. dye? ing half-tones or too lightlines theydo not proimage produced "upon. such'intermediateor transi.- tion' print to ultraviolet li'ghtta'nd upon .the transparency offthe. background t'oz. such light. It. die.- pen'ds also; upon the visual density of. the. image. produced on the: intermediate-yer transitionv print; since'image's oi.poorivi'sual. ;iinz;.suoh.as li'ghtl. yeilow's; on: a white or: transparent: background',..
though; they may have" the; desired degree: or
opacity-to-ultravioleh light, nevertheless have-thedisadvantages of renderingdifiicult the detection of flaws: in the intermediate image.- Withsuch prints it isr'necessary to-make a contrastprint. i
goodavisualidensity from the intermediate: before suchiflaws canebe detectedthereby introducing: an. additional and unnecessary step;
Prints? of: adeep-cclorhaving good, visual :den.--
l0 sity; can-.b'e obtained vfrom. diazotypes using" azodensity of the colorreproducing the image, its
actinic opacity or photographic density isnotsufe ficient to reproduce the image satisfactorily in subsequent copies. The-azo: dye. component used for the production of transition print images must be such as to producerupomcouplingawith the:
diazo compound employed a color which will sufficiently absorb the ultraviolet lightinc'ident upon it during exposureto'prevent light-decomposition of the diazo compound in the-areas to-be repro h duced fromthetransition copies. Colors of good visual density do notneeessarilyhave this property. It is well'known, for instance, that blues, such as" are produced from azo components like phloroglucin, are-very poor in their ultraviolet absorption characteristics.
Azo component's, sueh-asresorcinol, have heretofore been employed in the production of diazotype prints in order to obtain color images having the necessary light absorption characteristics for transition printing. Resorcinoliwill" reproduce the:imageron,the:transition print in a sepia or orange-brown color which has good opacity to ultraviolet light and has" sufiicient depth of color orvisualZ-d'ensity to assure detec- 40 tion oi printing flaws and the like in the devel- Other azo components,
oped intermediate print. have. been suggested which will produce images of, good opacity-on covering" power when used in combination witir polyhydroxy azo components,
as shaders for other" colorswhich may lack the necessary-i covering powerr,. particularly inv copy? duce satisfactory images when used as self colors, that is, when the acetoacetyl derivatives of 5 mono-amines, such. assthe cyclohexyl acetoacetic 'acid iamide and. the like disclosed in Patent 7 1,98 9,065,,ares.used as. the" onl'yazo' components for thie'develbpment' of a diazotype printy'the image produced does not have a satisfactory shade or tone value. a
It has now been found that certain cyanacetylamides containing an active methylene groupare especially effective as azo components for di azotype reproduction. These cyanacetylamides containing active methylene groups may be represented by the formula lene or Z S-dihydroXynaphthalene sulfonic acid,
excellent neutral blacks having improved opacity to ultraviolet light are obtained. Examples of cyanacetylamides having active methylene groups of this class are Cyanacetamide f i 2. Cyanacetanilide err-omoo-nnQ 3. p-I-Iydroxy cyanacetanilide 4. Cyanacetbenzylamide 5. l-1nethyl-2w-cyanacetyliminodihydroquinoline.
en meled-um 6. Cyanacetylurea CN-CHzCO-NHCONH:
7. Cyanacetylthiourea oN-omc ONH (ll-NH:
Cyanacetylguanidine I v oN-o Hio o-NH-c-Nm 9. Cyanacetylcyanamide CNCH2CONHCN 10. Cyanacetylethylurethane cn-onzco-mncoocgml 11. 1 w cyanacetylimino 2 methyl-E-ethoxydihydrobenzothiazole Y In the preparation of diazotype materials in tended for useas intermediate or transition print media in accordance with this invention, a suitable transparent base, such as transparentized paper, cellulose acetate film or other transparent material, iscoatedby means known to the art with a light sensitive composition containing suitable diazo compounds. Where it is desired to make a twmcomponent diazotype layer on the support or base material for development by the dry developing method. the azo component is also incorporated into the coating composition. Where one-component diazotype layers are desired, the azo component is added to an alkaline developing solution and after exposure of the diazotype, the exposed image is developed by contacting with the alkaline developing solution by means known to the art. In the preparation of coating compositions for two-component diazotype layers, the coating solution may also contain such other materials as are ordinarily used in the preparation of diazotype twoeoinponent light sensitive coating compositions. These include stabilizing materials, such as citric acid, phosphoric acid and thiourea; swelling agents for cellulose acetate and other cellulosic ester bases, such as isopropanol, and shade intensifying agents, such as nickel sulfate. In preparation of light sensitive layers on paper for the production of neutral black images or dark tone images which may or may not be intended for reproduction of further copies, it is preierable to employ a two-component coating composition which will contain one or more dark tone producing azo components, preferably such as will produce blue shades with the diazo compounds employed in combination with the nitrile acetyl, amide azo components of this invention. The diazo compound or compounds and. other ad juvants are added to the coating composition and the paper used as a carrier for the light sensitive layer is coated in the same manner as the trans parentized paper or oellulosic film base material in the case of the transition print media. As diazo compounds, any suitable light sensitive diazo compound which will couple with the azo components to reproduce a colored image, may be employed. We prefer, however, to use diazo compounds derived from p-diamines of the bon zene series, particularly when two-component coating compositions are employed. As is well known in the art, this class of diazo compounds is especiall suitable for the production of twocomponent diazotype photosensitized papers. Other diazo compounds have been found suitable for use, such as diazo anhydrides of aminohyethyl N-ethylaminoA aminobenzene p phe'riyl- 4-ami-no-N,:N-dihydroxyethylaniene :diamine: line; p- (4 -ethoxyphenyl) -.a'm'ino -i2,'5-diethoxyaniline; 1-N-ethylamino-2-methyl-4-aminoben zene; 1-dimethyl-amino-3-methoxy-4-aminobenacne; N;N-dimethyam'ino-p-aminobenzenej 1-'d 'i-" methylamin-o 3 methyl-4-aminobenzene-; -'p-' .aminophenyl morpholine and 2-amino-1-naph- 'thol-S-Sulfon-ic acid. The diazo derivatives 'of Example 1 Transparentized paper is coated with a coating solution containing the following ingredients per 10000. of water containing 5% of alcohol:
4.0grams cyanacetanilide 3.3 grams N-methyl-N-hydroxyethyl-p-benzene diazonium chloride-ZnClz double salt 4.0 grams thiourea 8.0 grams citric acid 2.0 grams phosphoric acid. 5.20 grams ZnCla [The resulting coated paper or diazotype good precoupling stability during prolonged stor-' age. After drying the coating in the usual manner, the diazotyp'e is exposed to light under a positive and the image developed with ammonia fumes. The image of the positive original is thus obtained .in a light brown colored positive print. The dye or color areas reproducing the image have good fade and 'wa'sh-fastness properties and excellent opacity to ultra-violet light. The print can be used as a transition print for the reproduction of further diazotype copies or other photo reproductions.
Example .2
-"-*irans parentized paper is coated with a coating solution containing the following ingredients per 100 cc. of water containing 5% of alcohol:
2.8 grams cyanacetylurea 3.8 grams .N-methyl-N-hydroxyethyl-Pebenzene Example 3 I Transparentized paper is coated with a diazotype coating solution containing the following ingredients per -:cc.-nf water containing 5% of alcohol:
34) grams cyanacetamide 32 grams l-iitil -ethy1amino) -'2-'methyl-&-1benzene diazonium chloride-ZnCh double salt 4.0 grams thiourea 8.0 grams citric acid 2.0 grams phosphoric acid 5.0 grams ZnCla The resulting coated paper-tor .diazot-ype mate-' rial has good precoupling stability during pro- After drying the coating in the' longed storage. usual manner, the diazotype is exposed .to light under a pattern, design or picture to be reproduced and the image .is developed with ammoniafumes... A positive image of the original is thus obtained in a Sepia color. The dye :or color areas reproducing the density sections of;
the original have good fade and wash-fastne's's properties and show excellentopacity to ultraviolet .light. The print, therefore, can be :used as :a transition or intermediate print for the reproduction of further diazotype copies or other photo -reproductions.
Upon substituting 3.5 grams cyanacetbenzyl-- amide,, 3.6 grams .1-iN ethyl-N hydroxyethyleamino) -3-methyl-4-benzene diazonium chloride ZnGlz-double salt or 3.3 grams cyanacetylethylurethane and 3.5 grams N-ethyl-N-hydroxye'thylp-benzene diaaonium chloride-ZnClz' double .salt
for the coupling component and .diazo compound of this example, respectively, diazotype materials having the same properties and reproducing the original in images of the same color as above are obtained.
Example A diazotype---co.ating solution containingthefollowingaingredients per 1-00 cc. of a 5% aqueous solution of alcohol is made up:
.Upon .using this coating solution to produce a diazotype coating on transparentized diazotype paper stock-and upon drying the coating in the usual manner, a-diazotype layer having excellent precouplingstability is obtained. Upon exposing "tne thus sensitized .transpa-rentized paper to light under a pattern, design or picture to .be reproduced and developing with ammonia fumes, a reproduction of the original in a black shade on "a' clear' background is obtained. This'dy'e image has good fade and wash-fastness properties and excellent opacity to ultraviolet light. Therefore, it can be used as a transition or intermediate print in the reproduction of further diazotype copies or other photoprint copies.
If a non-transparentized diazotype paper stock is used in the coating step and the usual diazotype procedure followed of drying and exposing under a pattern followed by ammonia development, an
ground results.
Example 5 Transparentized diazotype paper stock is coated with a coating solution containing the following ingredients per 100 cc. of water containing 5% of alcohol:
3.2 grams of cyanacetylthiourea 3.5 grams N,N-dihydroxyethyl-p-benzene diazonium ChIOIidG-CdClz double salt 4.0 grams thiourea 8.0 grams citric acid 2.0 grams phosphoric acid 5.0 grams ZnClz The resulting coated paper or diazotype material has good precoupling stability during prolonged storage. After drying the coating in the usual manner, the diazotype is exposed to light under a pattern or other original to be reproduced and the image is developed with ammonia fumes. The image of the original is thus obtained in a sepia colored positive print. The dye or color areas reproducing the density areas of the original have good fade and wash-fastness properties and excellent capacity to ultraviolet light. The print, therefore, can be used as a transition or intermediate print for the reproduction of further diazotype copies or other photoreproductions.
Upon substituting for the 3.2 grams cyanacetylthiourea coupling component and the 3.5
grams N,N-dihydroxyethyl-p-benzene diazonium chloride-CdClz double salt diazo compound of this example, th following combinations of coupling components and diazo compounds, diazotype coatings having the same properties as the coatings of this example are obtained:
(1) 3.3 grams cyanacetylguanidine 3.2 grams N-phenylamino-p-benzene diazonium acid sulfate 3.1 grams cyanacetylcyanamide 3.5 grams l- (N-ethyl N hydroxyethylamino) -3-methyl benzene-p a diazonium chloride-ZnClz double salt 3.4 grams cyanacetylethylurethane 3.8 grams N,N-cliethylamino benzene-pdiazonium chloride-ZnClz double salt 3.4 grams 1-w-cyanacetylimino-2-methyl-5- of the benzene series and an azo component selected from the class consisting of cyanacetylamides of the following formula CNCH2COR wherein R is a nitrogen containing radical of the class consisting of amino, arylamino, aralkylamino, a-iminodihydroheterocyclic, carbamido, thiocarbamido, carbamidino, cyanimido, and carboalkoxyimido radicals.
2. A diazotype photoprinting material comprisinga light sensitive diazonium salt of a p-diamine of. the benzene series and as an azo component cyanacetanilide having the structural formula 3. A diazotype photoprinting material comprising a light sensitive diazonium salt of a p-diamine of the benzene series and as an azo component cyanacetylurea having the structural formula 4. A diazotype photoprinting material comprising a light sensitive diazonium salt of a p-diamine of th benzene series and as an azo component cyanacetbenzylamide having the structural formula ON-CHzC ONHCHT 5. A diazotype photoprintlng material compris ing a light sensitive diazonium salt of a p-diamine of the benzene series and as an azo component cyanacetamide having the structural formula 6. A diazotype photoprinting material comprising a light sensitive diazonium salt of a p-diamine of the benzene series and as an azo component cyanacetylthiourea having the structural formula WILLIAM H. VON GLAI-IN. LESTER N. STANLEY.
REFERENCES CITED Thefollowing references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,989,065 Schmidt et a1 Jan. 22, 1935 2;1 08,602 Mannes et a1 Feb. 15, 1938 2,217,189 Sus Oct. 8, 1940 2312,040 Kendall et a1 Feb. 23, 1943 2,436,007 Kendall et al. Feb. 17, 1948: 2,453,661 Glass Nov. 9, 1948
Claims (2)
1. A DIAZOTYPE PHOTPRINTING MATERIAL COMPRIS-
1. A PROCESS FOR RECOVERING THE COMPONENTS OF OF THE BENZENE SERIES AND AN AZO COMPONENT SEA COMPLEX OF HYDROGEN FLUORIDE WITH POLYOLEFINIC LECTED FROM THE CLASS CONSISTING OF CYANACETYLCYCLIC HYDROCARBONS CONTAINING CONJUGATED AND AMIDES OF THE FOLLOWING FORMULA NON-CONJUGATED UNSATURATION, WHICH COMPRISES IN-
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US766875A US2537001A (en) | 1947-08-06 | 1947-08-06 | Diazotype layers having cyan acetyl amides as azo components |
| GB15164/48A GB644186A (en) | 1947-08-06 | 1948-06-04 | Diazotype photoprinting layers having cyan acetyl amides as azo coupling components |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US766875A US2537001A (en) | 1947-08-06 | 1947-08-06 | Diazotype layers having cyan acetyl amides as azo components |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2537001A true US2537001A (en) | 1951-01-02 |
Family
ID=25077788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US766875A Expired - Lifetime US2537001A (en) | 1947-08-06 | 1947-08-06 | Diazotype layers having cyan acetyl amides as azo components |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2537001A (en) |
| GB (1) | GB644186A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971663A (en) * | 1974-04-11 | 1976-07-27 | Bialczak Edward C | Light-sensitive diazotype with yellow diazo couplers |
| EP0001617A1 (en) * | 1977-10-17 | 1979-05-02 | Hoechst Aktiengesellschaft | Diazotype material |
| US4304831A (en) * | 1978-08-08 | 1981-12-08 | Ricoh Co., Ltd. | Black-color forming two-component type diazo copying material |
| US4642383A (en) * | 1982-09-30 | 1987-02-10 | James River Graphics, Inc. | Fast coupling lemon-yellow phenolic couplers |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1989065A (en) * | 1932-07-02 | 1935-01-22 | Kalle & Co Ag | Process for preparing diazo-types and light-sensitive layers therefor |
| US2108602A (en) * | 1935-03-21 | 1938-02-15 | Eastman Kodak Co | Photographic color-forming compounds |
| US2217189A (en) * | 1938-12-05 | 1940-10-08 | Kalle & Co Ag | Process of preparing photographic prints |
| US2312040A (en) * | 1938-07-22 | 1943-02-23 | Ilford Ltd | Production of colored photographic images by color development and composition therefor |
| US2436007A (en) * | 1944-05-12 | 1948-02-17 | Ilford Ltd | Dye intermediates for colour photography |
| US2453661A (en) * | 1944-05-03 | 1948-11-09 | Eastman Kodak Co | Colored couplers |
-
1947
- 1947-08-06 US US766875A patent/US2537001A/en not_active Expired - Lifetime
-
1948
- 1948-06-04 GB GB15164/48A patent/GB644186A/en not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1989065A (en) * | 1932-07-02 | 1935-01-22 | Kalle & Co Ag | Process for preparing diazo-types and light-sensitive layers therefor |
| US2108602A (en) * | 1935-03-21 | 1938-02-15 | Eastman Kodak Co | Photographic color-forming compounds |
| US2312040A (en) * | 1938-07-22 | 1943-02-23 | Ilford Ltd | Production of colored photographic images by color development and composition therefor |
| US2217189A (en) * | 1938-12-05 | 1940-10-08 | Kalle & Co Ag | Process of preparing photographic prints |
| US2453661A (en) * | 1944-05-03 | 1948-11-09 | Eastman Kodak Co | Colored couplers |
| US2436007A (en) * | 1944-05-12 | 1948-02-17 | Ilford Ltd | Dye intermediates for colour photography |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971663A (en) * | 1974-04-11 | 1976-07-27 | Bialczak Edward C | Light-sensitive diazotype with yellow diazo couplers |
| EP0001617A1 (en) * | 1977-10-17 | 1979-05-02 | Hoechst Aktiengesellschaft | Diazotype material |
| US4304831A (en) * | 1978-08-08 | 1981-12-08 | Ricoh Co., Ltd. | Black-color forming two-component type diazo copying material |
| US4642383A (en) * | 1982-09-30 | 1987-02-10 | James River Graphics, Inc. | Fast coupling lemon-yellow phenolic couplers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB644186A (en) | 1950-10-04 |
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