US3271155A - Thermo-developable diazo coatings employing dicyandiamide compositions - Google Patents
Thermo-developable diazo coatings employing dicyandiamide compositions Download PDFInfo
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- US3271155A US3271155A US247513A US24751362A US3271155A US 3271155 A US3271155 A US 3271155A US 247513 A US247513 A US 247513A US 24751362 A US24751362 A US 24751362A US 3271155 A US3271155 A US 3271155A
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- US
- United States
- Prior art keywords
- dicyandiamide
- diazo
- compositions
- composition
- diazonium
- 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.)
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- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 title claims description 80
- 239000000203 mixture Substances 0.000 title claims description 72
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 34
- 238000000576 coating method Methods 0.000 title description 22
- 239000012954 diazonium Substances 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 21
- 150000001989 diazonium salts Chemical class 0.000 claims description 16
- -1 DIAZO Chemical class 0.000 claims description 9
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 9
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 9
- 229920002866 paraformaldehyde Polymers 0.000 claims description 9
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 8
- 230000000087 stabilizing effect Effects 0.000 claims description 7
- 239000000758 substrate Substances 0.000 description 23
- 239000011248 coating agent Substances 0.000 description 15
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 3
- 229960001553 phloroglucinol Drugs 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 description 2
- 229960001748 allylthiourea Drugs 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LRUJNDUWNJTRHJ-UHFFFAOYSA-N 4-(4-diazo-2,5-diethoxycyclohexa-1,5-dien-1-yl)morpholine Chemical compound C1=C(OCC)C(=[N+]=[N-])CC(OCC)=C1N1CCOCC1 LRUJNDUWNJTRHJ-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- BKPQWCJHNZHKNU-UHFFFAOYSA-K C1(=CC=CC2=CC=CC=C12)S(=O)(=O)[O-].[Na+].[Na+].[Na+].C1(=CC=CC2=CC=CC=C12)S(=O)(=O)[O-].C1(=CC=CC2=CC=CC=C12)S(=O)(=O)[O-] Chemical compound C1(=CC=CC2=CC=CC=C12)S(=O)(=O)[O-].[Na+].[Na+].[Na+].C1(=CC=CC2=CC=CC=C12)S(=O)(=O)[O-].C1(=CC=CC2=CC=CC=C12)S(=O)(=O)[O-] BKPQWCJHNZHKNU-UHFFFAOYSA-K 0.000 description 1
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 239000005041 Mylar™ Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- BJLPUZSEAOIKNG-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].[Na].[Na].C1=CC=CC2=CC=CC=C21 BJLPUZSEAOIKNG-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- BERQWQSQOIEUMA-UHFFFAOYSA-M sodium;5,7-disulfonaphthalene-2-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 BERQWQSQOIEUMA-UHFFFAOYSA-M 0.000 description 1
- JFXDYPLHFRYDJD-UHFFFAOYSA-M sodium;6,7-dihydroxynaphthalene-2-sulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C=C2C=C(O)C(O)=CC2=C1 JFXDYPLHFRYDJD-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B7/00—Mixing; Kneading
- B29B7/74—Mixing; Kneading using other mixers or combinations of mixers, e.g. of dissimilar mixers ; Plant
- B29B7/7438—Mixing guns, i.e. hand-held mixing units having dispensing means
- B29B7/7452—Mixing guns, i.e. hand-held mixing units having dispensing means for mixing components by spraying them into each other; for mixing by intersecting sheets
-
- 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
- G03C1/61—Compositions containing diazo compounds as photosensitive substances with non-macromolecular additives
- G03C1/615—Substances generating bases
Definitions
- the present invention relates to a light sensitive, heatdevelopable diazonium composition and elements including such compositions. More specifically, this invention relates to diazonium compositions and products which may be developed by heat without the application of any discrete developing material.
- the diazo compositions most widely employed in conventional diazo coatings comprise a light decomposable diazonium salt, an organic coupling component and an acid.
- An element coated with this type of composition is exposed to light through a negative or positive and the diazonium salt is decomposed only in those areas exposed to the light.
- the unexposed areas remain undecomposed and are subject to further reaction in the presence of an alkaline reagent to produce a colored image with the coupler, whereas the exposed areas potential for being developed have been destroyed.
- the color producing reaction is produced by an alkaline compound, generally ammonia, either as a gas or in a solution.
- the prior art heat developable diazo types also have relatively poor shelf life under high humidity and temperature conditions.
- An object of this invention is to provide a light sensitive diazonium composition that is developable by heat.
- Another object of this invention is to provide for a diazo composition which may be employed in relatively simple azo copying devices where no means for generating developing fluids or evacuating noxious by-product vapors need be provided.
- Another object of this invention is the provision of a diazonium composition which may be employed as coatings on various substrates to produce highly useful photosensitive copying means.
- Another object of this invention is to provide heat developable diazo papers that have improved shelf life.
- the alkaline reagent does not enter into the coupling reaction. Its function is to neutralize the acid present and change the environment from acidic to neutral or basic. The coupling mechanism then takes place in the neutral or basic environment and the desired color formation takes place.
- diazo compositions which contain compounds capable of yielding alkaline developing products when decomposed by heat.
- the present invention comprises the in situ formation of an alkaline developing product which avoids the use of a separate alkaline treating step.
- dicyandiamide and analogous compounds or dicyandiamide and analogous compounds condensed with aldehydes will decompose when exposed to heat in the presence of an acid to yield alkaline decomposition products.
- the dicyandiamide or analogous compounds are combined with a diazo salt, coupler, acid, and stabilizer in one coating composition and applied to a substrate to produce a photosensitive heat developable coating.
- the prior art discloses the use of resin or semi-resinous condensation product of dicyandiamide and formaldehyde in diazo-type layers to improve their stability to decomposition on storage and improve fastness to washing of the image.
- resin or semi-resinous condensation product of dicyandiamide and formaldehyde in diazo-type layers to improve their stability to decomposition on storage and improve fastness to washing of the image.
- such systems do not rely upon the dicyandiamide compounds for the situ formation of basic decomposition products upon heating, thus avoiding the need for a separate alkaline treatment for developing the diazo composition.
- compositions used in heat developable diazo coatings comprising the reaction product of hydroxyl amine and phloroglucinol i.e. triketohexamethylenetrioxime. This compound decomposes when heated to yield phloroglucinol triketohexamethylene and ammonium hydroxide.
- the diazonium system of the present invention is much less complex in that a heat decomposable acid or strong salt of a weak acid need not be employed.
- the alkaline environment generated by the heat decomposition of dicyandiamide compounds is sufficient to promote the coupling reaction in the presence of acids less volatile and more stable to heat than those contemplated in prior techniques.
- the thermal decomposition products of dicyandiamide or its derivatives do not act as couplers in the present system, whereas the decomposition of triketohexamethylenetrioxime, according to the prior art, does produce a coupler.
- the present invention relates to heat developable, light sensitive diazonium compositions comprising light sensitive diazonium salts, diazonium couplers, an acid and a dicyandiamide composition which decomposes when heated to furnish alkaline decomposition products.
- the alkaline products reduce the acidity of the system and enable the diazonium salt and coupler to undergo a color forming reaction.
- dicyandiamide composition is intended to include dicyandiamide, its derivatives and mixtures thereof which decompose into alkaline products under the influence of heat.
- dicyandiamide is a correct chemical term
- cyanoguanidine gives a better description of the compound. Both terms designate the same material and can be used interchangeably.
- Dicyandiamide in the absence of citric or malonic acid, does not form a coupler. Its only purpose is to neutralize the acid upon thermal reaction. In the absence of an acid, slow decomposition of dicyandiamide starts at C. or above. Decomposition becomes rapid only above the melting point 206 C.
- the preferred embodiment of this invention incorporates an acid with the dicyandiamide composition although it is Within the scope of this disclosure to omit the acidic material should higher developing temperatures present no problem.
- shelf life is better than previously described formulations employing urea as a base generator.
- the urea compounds last for one Week, Whereas under the same conditions, the formulations described and disclosed by this invention last for 2-3 weeks, which is a substantial improvement over the prior art.
- the compositions of this invention can be differentiated by the different compounds employed.
- compositions are coated on paper.
- dicyandiamide compositions which Example Diazonium Salt Number Gin. Acid Gm. Dieyandiamide Composition Gm.
- the low molecular weight condensation products are soluble in water. Upon standing, a white precipitate of higher molecular weight material develops which can be redissolved upon heating. Molecular weights of the condensates have not been precisely determined. However, generally speaking, they are water soluble at ambient temperatures. Variations of heating time (up to one hour or more) or ratios of the initial materials change the reaction products somewhat. Addition of an alkaline catalyst (KOH) increases the rate of reaction, thus causing the formation of higher molecular weight condensation products.
- KOH alkaline catalyst
- Water ml 100 by definition include the dicyandiamide compositions listed in the examples, cyclohexyl dicyandiamide, o-tolyl dicyandiamide, p-tolyl dicyandiamide as well as aldehyde condensation products thereof with formaldehyde, acetaldehyde, paraformaldehyde and benzaldehyde and optionally a film forming material, any chemical or physical mixture thereof and any combination thereof including individual components recited above.
- the other coating or coatings will be referred to as a diazo composition, which will by definition include a diazonium salt, acid and couplers as given by the examples and specification and equivalents thereof and optionally a resinous film forming material, solvents and stabilizers given by the examples, specification and equivalents thereof, any physical or chemical mixture thereof and any combination thereof including individual components recited above.
- a diazo composition which will by definition include a diazonium salt, acid and couplers as given by the examples and specification and equivalents thereof and optionally a resinous film forming material, solvents and stabilizers given by the examples, specification and equivalents thereof, any physical or chemical mixture thereof and any combination thereof including individual components recited above.
- the application of the ingredients of the dicyandiamide composition, individually or any combination thereof, and the ingredients of the diazo composition individually or any combination thereof to either both or one side or any combination thereof of a substrate will be defined as a substrate contiguous to the diazo composition and dicyandiamide composition or a process of applying a diazo composition and dicyandiamide composition contiguous to a substrate.
- This contiguous relation is also one where the compositions will be on the substrate where the viscosity of the compositions are high or the substrate is non-porous or both, and in the substrate where the viscosity of the compositions are low and the substrate is porous or both.
- diazo composition and the dicyanadiamide composition will be considered contiguous with the substrate for purposes of definition, such as a separate dicyandiamide composition formed as a first layer over which the diazo composition is separately coated.
- the diazo composition can be the first coating and the dicyandiamide composition can be used as the second coating.
- Alternate layers of a dicyandiamide composition and diazo composition or diazo compositions can be used such as three coatings of different or the same diazo compositions.
- One, two, three and more than three diazo compositions can be used to produce different effects.
- Several layers of the diazo compositions can be used with one coating of a dicyandiamide composition on the bottom or top layer of the diazo compositions. When a porous or permeable substrate is used, a coating of dicyandiamide composition on the reverse side of the substrate containing the diazo composition can be used.
- the dicyandiamide compositions of this invention include not only those listed in the examples but also cyclohexyl dicyandiamide, o-tolyl dicyandiamide, p-tolyl dicyandiamide, as well as aldehyde condensation products of these dicyandiamides such as for example formaldehyde, acetaldehyde, paraformaldehyde, benzaldehyde condensation products, as well as other cyanoguanidines and aldehydes known to those skilled in the art.
- the above reactants are illustrative and not to be taken as limiting the disclosure. Any chemical or physical combination of the above are also to be considered dicyandiamide compositions.
- Non-limiting examples of diazonium salts in addition to those given in the examples include:
- p-diazo-dimethyl aniline zinc chloride p-diazo-diethyl aniline zinc chloride p-diazo-ethyl-hydroxyethyl aniline /2 zinc chloride p-diazo-Z,5-diethoxy-benzoylaniline /a zinc chloride p-diazo-ethyl-benzylaniline /2 zinc chloride p-diazo-l-morpholinobenzene /2 zinc chloride p-diazo-2,5-dibutoxy-l-morpholinobenzene /2 zinc chloride p-diazo-2,5-diethoxy-l-morpholinobenzene zinc chloride p-diazo-N-ethyl-O-toluidine zinc chloride, etc.
- Non-limiting examples of the diazo couplers include those given in the examples as well as:
- Non-limiting examples of the diazo stabilizer include those given in the examples as well as:
- 1,3,6-naphthalene-trisulfonic acid sodium salt allylthiourea hydroxy allylthiourea Any combination of the above are considered to be diazo stabilizers within the scope of this invention.
- the film forming resinous material referred to in the specification and claims of this application include cellulose nitrate, cellulose acetate, cellulose acetate butyrate,
- porous or non-porous substrates are also within the broad scope of this invention:
- glass fiber, glass, metal plastic film such as cellulose acetate, propionate, acetate butyrate polyethylene terephthalate (Mylar) paper, wood, composition board, etc.
- a light-sensitive heat-developable diazonium composition comprising a light-sensitive diazonium salt, a diazo coupler, a diazonium stabilizing acid and a dicyandiamide composition selected from at least one member of the group consisting of dicyandiamide, dodecyldicyandiamide, cyclohexyldicyandiamide, o-tolyldicyandiamide, p-tolyldicyandiamide, dicyandiamide formaldehyde, dicyandiamide acetaldehyde, dicyandiamide paraformaldehyde, and dicyandiamide benzaldehyde.
- a light-sensitive heat-developable diazonium composition comprising 0.5% to 10% by weight of a diazonium salt, from 1% to 10% by weight of a diazo coupler, from 1% to 20% by weight of a diazonium stabilizing acid, and from 3% to 25% by weight of a dicyandiamide composition selected from at least one member of the group consisting of dicyandiamide, dodecyldicyandiamide, cyclohexyldicyandiamide, o-tolyldicyandiamide, p-tolyldicyandiamide, dicyandiamide formaldehyde, dicyandiamide acetyldehyde, dicyandiamide paraformaldehyde, and dicyandiamide benzaldehyde.
- a dicyandiamide composition selected from at least one member of the group consisting of dicyandiamide, dodecyldicyandiamide, cyclohexyldic
- a light-sensitive heat-developable element comprising a substrate coated with a light-sensitive diazonium salt, a diazonium stabilizing acid, a diazonium coupler, a filmforming material, and a dicyandiamide composition selected from at least one member of the group consisting of dicyandiamide, dodecyldicyandiamide, cyclohexyldicyandiamide, o-tolyldicyandiamide, p-tolyldicyandiamide, dicyandiamide formaldehyde, dicyandiamide acetaldehyde, dicyandiamide paraformaldehyde, dicyandiamide benzalidehyde.
- a light-sensitive heat-developable element comprising a heat stable substrate, a dicyandiamide coating on said substrate selected from at least one member of the group consisting of dicyandiamide, dodecyldicyandiamide, cyclohexyldicyandiamide, o-tolyldicyan-diamide, p-tolyldicyandiamide, dicyandiamide formaldehyde, dicyandiamide acetaldehyde, dicyandiamide paraformaldehyde and dicyandiamide benzaldehyde, and a second discrete coating on such substrate contiguous with the first coating comprising a light-sensitive diazonium salt, a diazonium coupler and a diazonium stabilizing acid.
- a light-sensitive heat-developable element comprising a heat stable substrate, one coating on said substrate comprising from 3 to 25% by weight of a dicyandiamide composition selected from at least one member of the group consisting of dicyandiamide, dodecyldicyandiamide, cyclohexyldicyandiamide, o-tolyldicyandiamide, p-tolyldicyandiamide, dicyandiamide formaldehyde, dicyandiamide acetaldehyde, dicyandiamide paraformaldehyde and dicyandiamide benzaldehyde, and a second discrete coating on said substrate contiguous with said first coating com- 7 prising a light-sensitive diazonium salt, a diazon-iurn icoupler and a diazonium stabilizing acid.
- a dicyandiamide composition selected from at least one member of the group consisting of dicyandiamide, dodecyl
- a dicyandiamide composition selected from at least one member of the group consisting of dicyandiamide, dodecyldicyandiamide, cyclohexyldicyandiamide, o-tolyldicy
- a light-sensitive heat-developable diazotype composition comprising an aqueous solution of a light-sensitive diazonium compound, an azo dye coupler and dicyandi- 1 amide, said solution being stabilized at an acidic pH.
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- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Mechanical Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL301316D NL301316A (enrdf_load_stackoverflow) | 1962-12-27 | ||
| US247513A US3271155A (en) | 1962-12-27 | 1962-12-27 | Thermo-developable diazo coatings employing dicyandiamide compositions |
| GB47448/63A GB1023078A (en) | 1962-12-27 | 1963-12-02 | Thermo-developable diazo compositions |
| CH1561763A CH451700A (de) | 1962-12-27 | 1963-12-18 | Wärmeentwickelbares, lichtempfindliches Diazotypiematerial |
| SE14193/63A SE313734B (enrdf_load_stackoverflow) | 1962-12-27 | 1963-12-19 | |
| DE19631447713 DE1447713A1 (de) | 1962-12-27 | 1963-12-23 | Diazotypieverfahren |
| FR958322A FR1385702A (fr) | 1962-12-27 | 1963-12-24 | Couches diazoïques à développement thermique et utilisant des compositions de dicyanodiamide |
| BE641904A BE641904A (enrdf_load_stackoverflow) | 1962-12-27 | 1963-12-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US247513A US3271155A (en) | 1962-12-27 | 1962-12-27 | Thermo-developable diazo coatings employing dicyandiamide compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3271155A true US3271155A (en) | 1966-09-06 |
Family
ID=22935200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US247513A Expired - Lifetime US3271155A (en) | 1962-12-27 | 1962-12-27 | Thermo-developable diazo coatings employing dicyandiamide compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3271155A (enrdf_load_stackoverflow) |
| BE (1) | BE641904A (enrdf_load_stackoverflow) |
| CH (1) | CH451700A (enrdf_load_stackoverflow) |
| DE (1) | DE1447713A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1023078A (enrdf_load_stackoverflow) |
| NL (1) | NL301316A (enrdf_load_stackoverflow) |
| SE (1) | SE313734B (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3386826A (en) * | 1964-05-08 | 1968-06-04 | Ibm | Process for producing improved diazotype elements |
| US3389995A (en) * | 1964-09-15 | 1968-06-25 | Gen Aniline & Film Corp | Two-component heat developable diazotypes containing amidine compounds |
| US3642483A (en) * | 1966-11-07 | 1972-02-15 | Ricoh Kk | Thermally developable diazotype copying materials |
| US4275137A (en) * | 1974-09-13 | 1981-06-23 | Oce-Van Der Grinten N.V. | Light-sensitive diazotype material |
| US6280913B1 (en) | 2000-06-13 | 2001-08-28 | Eastman Kodak Company | Photographic element comprising an ion exchanged photographically useful compound |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1882065A (en) * | 1928-05-26 | 1932-10-11 | Marie D Cody | Fruit juice extractor |
| US2593911A (en) * | 1948-12-31 | 1952-04-22 | Gen Aniline & Film Corp | Diazotypes containing a condensation product of dicyandiamide with formaldehyde and a salt of ammonia or an aromatic amine |
| US2662013A (en) * | 1951-07-18 | 1953-12-08 | Gen Aniline & Film Corp | Diazotype photoprinting material |
| US2709655A (en) * | 1952-06-28 | 1955-05-31 | Gen Aniline & Film Corp | Diazotype photoprinting material |
| GB816601A (en) * | 1954-07-09 | 1959-07-15 | Arnold Tanenbaum | Improvements in or relating to diazotype processes |
| FR1249913A (fr) * | 1959-11-23 | 1961-01-06 | Bauchet & Cie Ets | Produit diazotype développable par la chaleur |
| US3046128A (en) * | 1958-07-03 | 1962-07-24 | Dietzgen Co Eugene | Thermally developable diazotype photoprinting material and production thereof |
-
0
- NL NL301316D patent/NL301316A/xx unknown
-
1962
- 1962-12-27 US US247513A patent/US3271155A/en not_active Expired - Lifetime
-
1963
- 1963-12-02 GB GB47448/63A patent/GB1023078A/en not_active Expired
- 1963-12-18 CH CH1561763A patent/CH451700A/de unknown
- 1963-12-19 SE SE14193/63A patent/SE313734B/xx unknown
- 1963-12-23 DE DE19631447713 patent/DE1447713A1/de active Pending
- 1963-12-27 BE BE641904A patent/BE641904A/xx unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1882065A (en) * | 1928-05-26 | 1932-10-11 | Marie D Cody | Fruit juice extractor |
| US2593911A (en) * | 1948-12-31 | 1952-04-22 | Gen Aniline & Film Corp | Diazotypes containing a condensation product of dicyandiamide with formaldehyde and a salt of ammonia or an aromatic amine |
| US2662013A (en) * | 1951-07-18 | 1953-12-08 | Gen Aniline & Film Corp | Diazotype photoprinting material |
| US2709655A (en) * | 1952-06-28 | 1955-05-31 | Gen Aniline & Film Corp | Diazotype photoprinting material |
| GB816601A (en) * | 1954-07-09 | 1959-07-15 | Arnold Tanenbaum | Improvements in or relating to diazotype processes |
| US3046128A (en) * | 1958-07-03 | 1962-07-24 | Dietzgen Co Eugene | Thermally developable diazotype photoprinting material and production thereof |
| FR1249913A (fr) * | 1959-11-23 | 1961-01-06 | Bauchet & Cie Ets | Produit diazotype développable par la chaleur |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3386826A (en) * | 1964-05-08 | 1968-06-04 | Ibm | Process for producing improved diazotype elements |
| US3389995A (en) * | 1964-09-15 | 1968-06-25 | Gen Aniline & Film Corp | Two-component heat developable diazotypes containing amidine compounds |
| US3642483A (en) * | 1966-11-07 | 1972-02-15 | Ricoh Kk | Thermally developable diazotype copying materials |
| US4275137A (en) * | 1974-09-13 | 1981-06-23 | Oce-Van Der Grinten N.V. | Light-sensitive diazotype material |
| US6280913B1 (en) | 2000-06-13 | 2001-08-28 | Eastman Kodak Company | Photographic element comprising an ion exchanged photographically useful compound |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1447713A1 (de) | 1969-01-09 |
| GB1023078A (en) | 1966-03-16 |
| CH451700A (de) | 1968-05-15 |
| NL301316A (enrdf_load_stackoverflow) | |
| SE313734B (enrdf_load_stackoverflow) | 1969-08-18 |
| BE641904A (enrdf_load_stackoverflow) | 1964-04-16 |
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