US2354088A - Stabilized diazx-type sensitive - Google Patents
Stabilized diazx-type sensitive Download PDFInfo
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- US2354088A US2354088A US2354088DA US2354088A US 2354088 A US2354088 A US 2354088A US 2354088D A US2354088D A US 2354088DA US 2354088 A US2354088 A US 2354088A
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- light
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- 238000000576 coating method Methods 0.000 description 29
- 239000011248 coating agent Substances 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 16
- 230000008878 coupling Effects 0.000 description 15
- 238000010168 coupling process Methods 0.000 description 15
- 238000005859 coupling reaction Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 12
- 150000008049 diazo compounds Chemical class 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 125000004076 pyridyl group Chemical group 0.000 description 10
- -1 amino aniline compound Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- 239000000987 azo dye Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000005493 quinolyl group Chemical group 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 3
- YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical compound CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241001050985 Disco Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000012360 testing method Methods 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
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- YEPACHVPVZZBRT-UHFFFAOYSA-N 3-phenyl-2-sulfoprop-2-enoic acid Chemical compound S(=O)(=O)(O)C(C(=O)O)=CC1=CC=CC=C1 YEPACHVPVZZBRT-UHFFFAOYSA-N 0.000 description 1
- 241001448862 Croton Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009937 brining Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical class NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- G03C1/61—Compositions containing diazo compounds as photosensitive substances with non-macromolecular additives
Definitions
- This invention relates to the stabilization ol light-sensitive layers which are produced by the incor ration or a dlazo compound as the llghu sensitive medium onto the surlac 0! a suitable carrier base. More particularly. it refers to the stabilization of so-called dry development or two component dlazo type lightscnsitivc layers wherein the diazo compound is 0. disco compound derived from ortho or para aminonaphthol or from N-mono or di-substltuted aromatic persdiamines such 8.5 para amino aniline compounds, which diazo compound is incorporated into the light-sensitive layer. together with an azo dyc stufi coupling component.
- the develo ment or the dyestufl iorming the image i flected by brin ing the exposed light-sensitive layer into contact with ammonia gas This is known as the dry developing process.
- the dyestufl components, as applied on the carrier, are relatively unstable and cannot be stored for long periods prior to use.
- the light-sensitive layers which carry the coupling component as well as the dlazo compound in the light-sensitive layer are subject to premature coupling of the said dyestufl components as well as decomposition of the dlazo compound upon long storage.
- Many attempts have been made to obtain more stable coating solutions and to render the light-sensitive layers produced therefrom less sensitive to deterioration without impairin the light-sensitive qualities oi the diazo compound upon which the production 01' accurate images from the original depends. These attempts have hitherto been relatively unsuccess- Iul. It is therefore the object of this invention to provide coating solutions and light-sensitive it coon wherein R stands for a radical of the group consisting of alkyl. phenyl, pyridyl, quinolyl, and
- Diazotype light-sensitive layers which have been stabilized by addition or compounds selected from the above group show greatly improved keeping qualitles and are stable against decomposition or deterioration ior much longer periods of storage than has been possible with the same dlazo lightsensitive compositions lacking this stabilizing ii'ibound ii'n which previously SUgEELLEd sta- 50 cc. isopropanol are added.
- the stability of billzing compounds have been used.
- the ioiiow the coating made according to this example was ing examples illustrate the invention but they found to be superior to that of a comparison coatui'e not intended to limit it thereto.
- the pa t irig made from a similar coating solution but conare by weight unless otherwise stated. taining no acrylic acid stabilizer.
- cori'diti'onsflior the so me -iignt-seri sitive laser 5i 'thrs' i'tampie'butkiierittirig lehgtho'! timei 1 Th bsck'grouiid'a'h'ri oo'n'sequ'ent"- the sulio -cinnsi riivabld ad'dlti'o'h; It-lfia' ' ⁇ Qdti'q iy the contrast of the image reproduced on the thdtthe'liizht slensitivelayersdiddeili sttiidifdfati'de iightsensltive layer made in accordance with this with this example shovt iflr'ieg'liig'ifilia"arii'odnt.
- composition or the coatlpg solution is the i r same as in mample I except that in place or the crotonic acid as a stabilizer, 15.15 grams of betatalpha-pyridyl)acrylic acid per liter are exoe t that-jnr la r.is l nnam cii employed.
- Example X 2 methyl 4 amlnobenzene 9.8 Citric acid 50 Resorclne 6.5 'Ihiourea 45 The sodium salt oi the naphthalene-1,3,6,
- Example II To this solution there are added 25.5 grams of suliocinnamic acid per liter. The coating. storage and testing procedures are the same as in Example I. The stability oi the coating made according to this example was iound to be superior to that of a coating made from a solution not containing an acrylic acid stabilizer.
- Aluminum suliate are dissolved in 1000 cc. of
- test pieces are then exposed to light under a suitable diaposltlve and the images developed by application oi an alkali solution of a suitable azo component such as phloroglucine, resorcine, or 2-3-dihydroxy-naphthalene.
- a suitable azo component such as phloroglucine, resorcine, or 2-3-dihydroxy-naphthalene.
- the resulting image produced on the light-sensitive layer containing the sulio-cinnamic acid showed a much higher color contrast of the image: indicating the prevention of the decomposition and the consequent discoloration of the disco-compound while at storage under the some length or time.
- a diazotype light-sensitive layer containing a suitable diazo compound which comprises adding to the coating solution on alpha-bcta-unsatureted acrylic acid or the tollowing formula:
- R stands for a radical selected from the group consisting of alkyl, phenyl, pyridyl. quinolyl and substituted phenyl, pyridyl and quin olyl radicals, and coating a suitable base with said solution.
- the process oi increasing the stability of a diazotype light-sensitive layer containing a diam compound obtained from a para amino aniline compound and an arc dye coupling component, which comprises adding sulfo-cinnamic acid to the coating solution and coating a suitable base with said solution.
- Light-sensitive layers on a suitable base comprising a diazo compound suitable for forming a stable two component diazotype layer.
- a diazo compound suitable for forming a stable two component diazotype layer comprising a diazo compound suitable for forming a stable two component diazotype layer.
- R stands for a. radical selected from the group consisting of alkyl hony], pyridyl. quinoiyi and substituted henyi, pyridyi and quinolyi radicals 8.
- Light-sensitive layers on a suitable base comprising n dinzo compound obtained from a para amino aniline compound. an azo dye coupling component. and an aipha-beta-unsaturated acrylic acid or the 'oiiowing iormuiat wherein R stands for a radical selected from the group consisting or alkyl, phcnyl, pyridyl, quinclyi ond substituted phenyi, pyridyi and quinoiyl rsdioais.
- Liam-sensitive layers on a. suitable bue comprising a dim compound obtained irom 4i para amino aniline compound, an azo dye coupling component and sulio-cinnamic acid.
- Light-sensitive layers on a suitable blue comprising a diazo compound obtained from a para amino aniline compound, an azo dye coupiin: component and pentenic acid.
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Description
Patented July 18, 1944 UNITED STATES PATENT OFFICE STABILIZED DIAZO-TYPE- SEN SITIVE MATERIAL No Drawing.
Application December 4, 1942,
Serial No. 467,901
11 Claims.
This invention relates to the stabilization ol light-sensitive layers which are produced by the incor ration or a dlazo compound as the llghu sensitive medium onto the surlac 0! a suitable carrier base. More particularly. it refers to the stabilization of so-called dry development or two component dlazo type lightscnsitivc layers wherein the diazo compound is 0. disco compound derived from ortho or para aminonaphthol or from N-mono or di-substltuted aromatic persdiamines such 8.5 para amino aniline compounds, which diazo compound is incorporated into the light-sensitive layer. together with an azo dyc stufi coupling component.
Various processes are known for the preparation of light-sensitive layers which depend upon the use of a diazo compound as the llght-sensltive medium, and various materials have been employed for the carrier of the light-sensitive layer, including textiles, paper, celluloslc films, and glass and metal surfaces. The sensitized carrier is exposed to light under a transparent original which it is desired to reproduce and the disco compound is decomposed in th areas unprotected by the outline of the original. The undecomposed diazo compound in the protected areas is then used to develop the image or the original by coupling the said dlazo compound in alkaline atmosphere with an em dyestufl coupling component. In the two component layers which contemplate the incorporation of the coupling component into the light-sensitive layer with the dlszo compound, the develo ment or the dyestufl iorming the image i flected by brin ing the exposed light-sensitive layer into contact with ammonia gas. This is known as the dry developing process.
The dyestufl components, as applied on the carrier, are relatively unstable and cannot be stored for long periods prior to use.
The light-sensitive layers which carry the coupling component as well as the dlazo compound in the light-sensitive layer are subject to premature coupling of the said dyestufl components as well as decomposition of the dlazo compound upon long storage. Many attempts have been made to obtain more stable coating solutions and to render the light-sensitive layers produced therefrom less sensitive to deterioration without impairin the light-sensitive qualities oi the diazo compound upon which the production 01' accurate images from the original depends. These attempts have hitherto been relatively unsuccess- Iul. It is therefore the object of this invention to provide coating solutions and light-sensitive it coon wherein R stands for a radical of the group consisting of alkyl. phenyl, pyridyl, quinolyl, and
substituted phenyl. pyridyl and qulnolyl radicals. Examples oi such compounds are:
Crotonic acid CHJCH=CHCOOH Pentenic acid CsHsCH=CHCOOH Sulio-cinnsmic acid CB=CHCOOU soul Betai alpha-pyridyl) -acrylic acid N CH==CH-COOR Beta-Z-methyl-quinolyl (5) -acryllc acid noocnc==cn The compounds of this group can exist in both the cisand transform, either of which is suitable for the purposes oi this invention. Diazotype light-sensitive layers which have been stabilized by addition or compounds selected from the above group show greatly improved keeping qualitles and are stable against decomposition or deterioration ior much longer periods of storage than has been possible with the same dlazo lightsensitive compositions lacking this stabilizing ii'ibound ii'n which previously SUgEELLEd sta- 50 cc. isopropanol are added. The stability of billzing compounds have been used. The ioiiow the coating made according to this example was ing examples illustrate the invention but they found to be superior to that of a comparison coatui'e not intended to limit it thereto. The pa t irig made from a similar coating solution but conare by weight unless otherwise stated. taining no acrylic acid stabilizer.
g xqnip I. ample Vt 2-1-diazo -hydroxy-rihi h hillEIfQ-iJ-BUUDIHC" Parts a id prirts 14.0 Zinc chloride double salt or the diazo-com- Conc. hydrochloric acid -i0 pound obtained from N-cthanol-ethyl parts by v9 w n 1 i7 0, ammo qq i gql 10.5 Nickel sulphate ;-1 m't.; its. Qitric 50 Pmorogiucine -do 4.9 2-Q-dihydroxy-naphthalene 5.0 Thiourea -22 l LliLsdox- 20.0? 'LhibQieaL-Q UIs't z'ME- 45 .i-Jl I il u 1! Cl NB] U L were dissolved in 1000 cc. 0! v ste r. Befor t r} fiiifi jg gfii gfti:fff f i f 6 32 5 ing there were added 8.74 grams per liter of cro-Mfmmqmmgmwkpmw 0 6.9
tonic acid. This solution wts tnerr-apieqgt, paper, fabric, film or the like by the usual coat ivere'dissoived in 1000 cc. oi water. Before coating method, using a doctor blade to insure srgthlrt. ,llliliihere were added 255 grams oi sulio-cinnilmic even coating. Alter storage at room temperature acid. This solutlon was spread on a suitable peso. sevfal: months imasmmmy i mig mze such as paperfiidbriciflin'i or the'lil'r'e: by the usual material cont-aiding the' drotonic acid was tiesbcd coatir fl it hod lll't'il 'saine marit er s iti'diesteq byexposing lde'st' piebe to-ilght Under-a suitable -in'-Fi1xam'ple '12"The"1igliU BBIiSiLMKE-Ipij h thus dlupositive and deveicpirrg the-ima e by appli prouuceti was thetist orefd ailroomj triiperatri'rerbr eation or ammonia'gasf 'lh'e resliltlri image fro- 26 'severai rn'onths ahdits stsbiiltv t ei-iit'etdby produced ctr-the lightkseh'sltlve layer coht'aiznirig observin the ap eeriinee or" win; m 'tii' 1 tig i w g m t u mgg sensitive'lbiye'r due to premature coupling'of'the r produce'd under thsamecondit ns 118W: ,P 'and' *bycdfiiba'ris'dii difi lihtsensltive'lflyer madeiroflfithsiflmi materials out senaltlve qiis.iitieo mm those" 'of" si*t'es'tfsm;ii containing-no--erot mic tteid 'wmen had-{been propared ah'dt'reatedirithtz'sanie satisfies mm titdred uhier mettle? cori'diti'onsflior the so me -iignt-seri sitive laser 5i 'thrs' i'tampie'butkiiriittirig lehgtho'! timei 1 Th bsck'grouiid'a'h'ri oo'n'sequ'ent"- the sulio -cinnsi riivabld ad'dlti'o'h; It-lfia' '{Qdti'q iy the contrast of the image reproduced on the thdtthe'liizht slensitivelayersdiddeili sttiidifdfati'de iightsensltive layer made in accordance with this with this example shovt iflr'ieg'liig'ifilia"arii'odnt. of example was superior to that of the sample which coloring due to refnh'tu're coppliii'g -ofithfi does not contain th'croton'ic acid in the lightoompong it 5mg. ain'kh fly' ers rmiad'e sensitive l ve irom' theit'mjri seiutib'r'iiii'ilt'fhpt a i g; m g; "maps H m weete Wtbe c' fidrili Th p eiisthesamessinwmamnlo-rl s consieeese 'anieairitoi siciini 'diiw rhia except that in place of the crownic acid as a curco'upliiigi it' wii jiisd fmjfi flihe fitig 55 stabilizer 10.0 grams or ente i acid per liter mt q ht iihder a iiitstii-siabbgit te fia are used. The stability 'or the qoqt in pa s de utmp mrimgq twg ,iinm g i amg w 4. w i a es fler id i rawji similar coating solution but oontainingno acrylic 19 buckgro "fi n w m ri g t i 't i ing to this example was ioundto be superior to stabilizer'fi'ilfflamd ol cioto'r'iic said'sei tei si that of a comparison coating made from a similar 55 usadi-fl rho starbilitroi thef cbit'tihiz'hihde iiccofd coating solution but containing no acrylic acid in]; w this exam'ple wsb' fbundwobiitifiiidito stabilizer. that of a. comparison coating mi'iciei'frorr igsif fllsr Example IV I 4 r nagging bolutlohitiut do'rimm{fig fl l yn kq The composition or the coatlpg solution is the i r same as in mample I except that in place or the crotonic acid as a stabilizer, 15.15 grams of betatalpha-pyridyl)acrylic acid per liter are exoe t that-jnr la r.is l nnam cii employed. Toi acilitqte solution cc. of alcohol muu nqo g gm m mi g. mg 81'! added to t h waterT,The stability of the COBta mecbq qfh wbunyi 6p i-PW. s w/teem iilisrwmle JYMJ RM w cording w thlsfhxh'rfrblE wsi gc imd'tai' s'e' s11 has be u or. o l t-,9! A ome isen cmi z made to that ium esmsaiisaa ethiti ii iiia yi is shoot-mi r. (Dhoisprocadure 11s .lthe 'samtr as in mehifawv rg tion 50 cc. of alcohol are added. The stability oi the coating made according to this example was iound to be superior to that oi a comparison coating made from a similar coating solution but containing no acrylic acid stabilizer.
Example X 2 methyl 4 amlnobenzene 9.8 Citric acid 50 Resorclne 6.5 'Ihiourea 45 The sodium salt oi the naphthalene-1,3,6,
trisulionic acid 32,6 Aluminum sulfate are dissolved in 1000 cc. of
water 6.9
To this solution there are added 25.5 grams of suliocinnamic acid per liter. The coating. storage and testing procedures are the same as in Example I. The stability oi the coating made according to this example was iound to be superior to that of a coating made from a solution not containing an acrylic acid stabilizer.
Aluminum suliate are dissolved in 1000 cc. of
water To this solution there are added 255 grams of sulio-cinnamlc acid per liter. The solution is then spread on a suitable base, such as paper, iabric, him or the like by the usual coating method in the same manner as described in Example I. The light-sensitive layer thus produced is then stored at room temperature ior several months, and its stability is then tested by observing the appearance of color in the light-sensitive layer due to decomposition of the dimcompound and by comparison with that or a test sample prepared and treated in the same manner as the light-sensitive layer of this example but omitting the suiio-cinnamic acid. The test pieces are then exposed to light under a suitable diaposltlve and the images developed by application oi an alkali solution of a suitable azo component such as phloroglucine, resorcine, or 2-3-dihydroxy-naphthalene. The resulting image produced on the light-sensitive layer containing the sulio-cinnamic acid showed a much higher color contrast of the image: indicating the prevention of the decomposition and the consequent discoloration of the disco-compound while at storage under the some length or time.
Various changes may be made in the details oi my invention as described in the foregoing specidcation within the scope of the claims appended hereto without sacrificing the advantages oi myinvention.
I claim:
1. The process or increasing the stability 0! a diazotype light-sensitive layer containing a suitable diazo compound which comprises adding to the coating solution on alpha-bcta-unsatureted acrylic acid or the tollowing formula:
wherein it stands for a radical selected from the group consisting oi allryl, phenyl, pyridyl, quinolyl and substituted phenyl, pyridyl and quinolyl radicals. and coating is suitable base with said solution.
2. The process of increasing the stability of a dlazotype light-sensitive layer containing a diazo compound suitable for iomiing a stable two component diazotype layer and an am dye coupling component, which comprises adding to the coating solution an alpha-beta-Lmsaturated acrylic acid of the following formula:
wherein R stands for a radical selected from the group consisting of alkyl, phenyl, pyridyl. quinolyl and substituted phenyl, pyridyl and quin olyl radicals, and coating a suitable base with said solution.
3. The process of increasing the stability oi a diazotype light-sensitive layer containing a diazo compound derived from a para amino aniline compound and an azo dye coupling component, which comprises adding to the coating solution containing the said diazo compound an alphabeta-unsaturated acrylic acid or the following wherein R stands for a radical selected from a group consisting of alkyl, phenyl, pyridyl, quinolyl and substituted phony], pyridyl and quinolyl radicals, and coating a suitable base with said solution.
4. The process oi increasing the stability of a diazotype light-sensitive layer containing a diazo compound obtained from an ortho amino naphthol compound and an azo dye coupling component. which comprises adding crotonlc acid to the coating solution and coating a suitable base with said solution.
5. The process oi increasing the stability of a diazotype light-sensitive layer containing a diam compound obtained from a para amino aniline compound and an arc dye coupling component, which comprises adding sulfo-cinnamic acid to the coating solution and coating a suitable base with said solution.
8. The process of increasing the stabilit at a diaz-otype light-sensitive layer containing a diam compound obtained lrom a para amino aniline compound and an azo dye coupling component, which comprises adding pentenic acid to the coating solution and coating a suitable base with said solution.
'7. Light-sensitive layers on a suitable base comprising a diazo compound suitable for forming a stable two component diazotype layer. an azo dyestufl coupling component and an alpha-betaunsaturaicd acrylic acid of the foilowma formulo:
wherein R stands for a. radical selected from the group consisting of alkyl hony], pyridyl. quinoiyi and substituted henyi, pyridyi and quinolyi radicals 8. Light-sensitive layers on a suitable base comprising n dinzo compound obtained from a para amino aniline compound. an azo dye coupling component. and an aipha-beta-unsaturated acrylic acid or the 'oiiowing iormuiat wherein R stands for a radical selected from the group consisting or alkyl, phcnyl, pyridyl, quinclyi ond substituted phenyi, pyridyi and quinoiyl rsdioais.
9. Liam-sensitive layers on a suitable base com prising a diam-compound obtained from an ortho amino naphthoi compound, an azo dye coupiinl component and crotonic acid.
10. Liam-sensitive layers on a. suitable bue comprising a dim compound obtained irom 4i para amino aniline compound, an azo dye coupling component and sulio-cinnamic acid.
11. Light-sensitive layers on a suitable blue comprising a diazo compound obtained from a para amino aniline compound, an azo dye coupiin: component and pentenic acid.
MAXINHLIAN K. REICHZEL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46790142A | 1942-12-04 | 1942-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2354088A true US2354088A (en) | 1944-07-18 |
Family
ID=23857604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2354088D Expired - Lifetime US2354088A (en) | 1942-12-04 | Stabilized diazx-type sensitive |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2354088A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2495827A (en) * | 1947-08-06 | 1950-01-31 | Gen Aniline & Film Corp | Diazotype materials stabilized with an alpha-alkylidene-polymethylene dicarboxylic acid |
| US2537097A (en) * | 1945-08-18 | 1951-01-09 | Gen Aniline & Film Corp | Dyeing of textile materials by the use of light-sensitive diazo salts |
| US2649221A (en) * | 1951-08-30 | 1953-08-18 | Wagner | Taping machine |
| US2996381A (en) * | 1957-07-02 | 1961-08-15 | Kalvar Corp | Photographic materials and procedures for using same |
| US3064562A (en) * | 1959-01-12 | 1962-11-20 | Lithoplate Inc | Acrylic acid monomer coatings for metal bases |
| FR2373812A1 (en) * | 1976-12-10 | 1978-07-07 | Oce Van Der Grinten Nv | DEVELOPMENT LIQUID FOR DIAZOTYPIA MATERIAL |
| US4149888A (en) * | 1972-06-26 | 1979-04-17 | Gaf Corporation | Transparent photographic masks |
| US4403028A (en) * | 1981-01-26 | 1983-09-06 | Andrews Paper & Chemical Co., Inc. | Light sensitive diazonium salts and diazotype materials |
-
0
- US US2354088D patent/US2354088A/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2537097A (en) * | 1945-08-18 | 1951-01-09 | Gen Aniline & Film Corp | Dyeing of textile materials by the use of light-sensitive diazo salts |
| US2495827A (en) * | 1947-08-06 | 1950-01-31 | Gen Aniline & Film Corp | Diazotype materials stabilized with an alpha-alkylidene-polymethylene dicarboxylic acid |
| US2649221A (en) * | 1951-08-30 | 1953-08-18 | Wagner | Taping machine |
| US2996381A (en) * | 1957-07-02 | 1961-08-15 | Kalvar Corp | Photographic materials and procedures for using same |
| US3064562A (en) * | 1959-01-12 | 1962-11-20 | Lithoplate Inc | Acrylic acid monomer coatings for metal bases |
| US4149888A (en) * | 1972-06-26 | 1979-04-17 | Gaf Corporation | Transparent photographic masks |
| FR2373812A1 (en) * | 1976-12-10 | 1978-07-07 | Oce Van Der Grinten Nv | DEVELOPMENT LIQUID FOR DIAZOTYPIA MATERIAL |
| US4403028A (en) * | 1981-01-26 | 1983-09-06 | Andrews Paper & Chemical Co., Inc. | Light sensitive diazonium salts and diazotype materials |
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