US3769021A - Light-sensitive diazotype copying material - Google Patents
Light-sensitive diazotype copying material Download PDFInfo
- Publication number
- US3769021A US3769021A US00115057A US3769021DA US3769021A US 3769021 A US3769021 A US 3769021A US 00115057 A US00115057 A US 00115057A US 3769021D A US3769021D A US 3769021DA US 3769021 A US3769021 A US 3769021A
- Authority
- US
- United States
- Prior art keywords
- chloride
- diazonium
- solution
- light
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000463 material Substances 0.000 title abstract description 15
- 150000001989 diazonium salts Chemical class 0.000 abstract description 22
- 239000012954 diazonium Substances 0.000 abstract description 8
- 230000035945 sensitivity Effects 0.000 abstract description 4
- CVDKUNVLQOHHFZ-UHFFFAOYSA-N 4-(dibenzylamino)benzenediazonium Chemical class C1=CC([N+]#N)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 CVDKUNVLQOHHFZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 34
- -1 pyrrolidino radical Chemical class 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 20
- 239000011592 zinc chloride Substances 0.000 description 17
- 235000005074 zinc chloride Nutrition 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000975 dye Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000001632 sodium acetate Substances 0.000 description 10
- 235000017281 sodium acetate Nutrition 0.000 description 10
- XAQUIOSBVRWKRI-UHFFFAOYSA-M 2-ethoxybenzenediazonium;chloride Chemical compound [Cl-].CCOC1=CC=CC=C1[N+]#N XAQUIOSBVRWKRI-UHFFFAOYSA-M 0.000 description 8
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 7
- 229940073608 benzyl chloride Drugs 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000006193 diazotization reaction Methods 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000006228 supernatant Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 150000001805 chlorine compounds Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 5
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000009835 boiling Methods 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
- 239000011780 sodium chloride Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 description 1
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BSXXBLMYFXGNMT-UHFFFAOYSA-N 2-ethoxybenzenediazonium Chemical compound CCOC1=CC=CC=C1[N+]#N BSXXBLMYFXGNMT-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JDQOQWKEOLQHKB-UHFFFAOYSA-N 4-aminobenzenediazonium Chemical class NC1=CC=C([N+]#N)C=C1 JDQOQWKEOLQHKB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- MHMQGJBUQUDINX-UHFFFAOYSA-N ethoxybenzene Chemical compound [CH2]COC1=CC=CC=C1 MHMQGJBUQUDINX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- KVEDKKLZCJBVNP-UHFFFAOYSA-N n-(4-acetamidophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(NC(C)=O)C=C1 KVEDKKLZCJBVNP-UHFFFAOYSA-N 0.000 description 1
- HMDZGLGPRFBFFU-UHFFFAOYSA-N n-acetyl-n-(4-aminophenyl)acetamide Chemical compound CC(=O)N(C(C)=O)C1=CC=C(N)C=C1 HMDZGLGPRFBFFU-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JVUYWILPYBCNNG-UHFFFAOYSA-N potassium;oxido(oxo)borane Chemical compound [K+].[O-]B=O JVUYWILPYBCNNG-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000004383 yellowing Methods 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
- G03C1/54—Diazonium salts or diazo anhydrides
Definitions
- ABSTRACT A diazotype copying material having a light-sensitive coating containing a diazonium salt selected from the group consisting of 2,5-disubstituted derivatives of 4- dibenzylamino-benzene diazonium salt exhibits a very high sensitivity to light.
- R is selected from the group consisting of a hydroxyl radical, an alkoxy or phenyl-substituted alkoxy radical having from one to four carbon atoms in the alkyl chain, a morpholino radical, a pyrrolidino radical, a piperidino radical, a piperazino radical and wherein R, and R are alkyl radicals having from one to four carbon atoms;
- Y is selected from the group consisting of hydrogen, an alkyl radical having from one to four carbon atoms, an alkoxy radical having from one to four carbon atoms, a hydroxyl-substituted alkoxy radical having from one to four carbon atoms, and a morpholino-, pyrrolidino-, piperidinoor piperazino-substituted alkoxy radical having from one to four carbon atoms;
- n is an integer between 1 and 4;
- X represents an anionic radical
- the diazonium compounds according to the present invention may be applied to one-component copying materials which are developed according to the moistdevelopment method, two-component copying materials which are developed according to the drydevelopment method and also to three-component copying materials which are developed according to the thermal development method.
- these diazonium compounds of the present invention there are obtained copies of images varying in color such as black and blue, depending on the type of the azo coupling component used.
- the light-sensitive copying layer is coated on a support such as paper, precoated paper and plastic foil which is used in ordinary diazotype copying materials.
- This copying layer may contain an additive such as an anti-yellowing agent and a stabilizer.
- the diazonium compounds used in the present invention are prepared, in many cases, in the form of diazonium chloride or double salt of diazonium chloride and metal chloride, and in particular, they are obtained in the form of double salts of diazonium chloride and zinc chloride or double salts of diazonium chloride and cadmium chloride.
- the type of anion which is coupled to the diazonium cation is not critical.
- Diazonium compounds in the form of, for example, bromides, sulfates and fluoroborates may also be used in the present invention.
- the preferred alkyl radicals include methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl.
- the preferred alkoxy radicals include methoxy, ethoxy, n-propoxy, iso-propoxy and n-butoxy.
- the preferred N R2 radicals include N-methylamino, N-ethylamino, N,N- dimethylamino, N,N-diethylamino and, N,N-npropylamino.
- the diazonium compounds of the present invention may be applied to one-component, two-component and three-component copying materials.
- the diazonium compounds show an increased coupling velocity and such compounds are particularly suitable for both one-component and two-component copying materials.
- diazonium compounds which are used in the present invention. It should be understood, however, that the diazonium compounds which are usable in the present invention are not restricted to these compounds alone.
- Formula 1 Formula 2 h C 1H4 O H2- Formula 3
- Formula 4 Formula 5 CH3 i gag O C2H4N (C2115) HCl (124-129 C.) [4l0-415 m (l28-132 c.) 410 115 mu] (105-111 C.) [410-415 mp] (119-122 C.) [400-405 mp]
- This distillate was coupled to a diazonium compound of p-nitroaniline to produce a dyestuff, with the yield being 57 g (The resulting substance has a melting point between 202C. and 204C).
- This dyestuff was then reduced with hydrogen gas to an amino compound.
- This latter compound was reacted with acetic anhydride to cause N,N-diacetyl-pdiaminobenzene to separate out.
- the obtained acetyl compound was subjected to hydrolysis, followed by diazotization in a known manner.
- the resulting diazonium compound was salted out with zinc chloride.
- acetyl compound was neutralized with additional sodium acetate, thereby producing a dyestuff, with the yield being 106 g (The resulting substance had a melting point between 210C. and 212C.).
- This dyestuff was then reduced with hydrogen gas to an amino compound.
- This latter compound was reacted with acetic anhydride to cause N,N-diacetyl-pdiaminobenzene to separate out.
- the obtained acetyl compound was subjected to hydrolysis, followed by diazotization by known manner, and salted out by zinc chloride.
- This distillate was coupled to a diazonium compound of p-nitroaniline to produce a dyestuff, with the yield being 68 g (The resulting substance had a melting point between 197C. and 199C)
- This dyestuff was then reduced with hydrogen gas to an amino compound.
- This latter compound was reacted with acetic anhydride to cause N,N'-diacetyl-pdiaminobenzene to separate out.
- the obtained acetyl compound was subjected to hydrolysis, followed by diazotization by known manner, and was salted out by zinc chloride.
- acetyl compound was subjected to hydrolysis, followed by diazotization by known manner, and salted out by zinc chloride.
- zinc chloride double salt which was yellow in color were obtained.
- This double salt has a decomposition point between 128C. and 132C. and a peak of ultraviolet absorption within the range of 410 mg to 415 mu.
- FORMULA 8 One hundred eleven grams of Z-methyl-S-(B- morpholino) ethoxyaniline and 82 g of sodium acetate were dissolved in 50 ml of water. While maintaining the temperature of this solution between C. and C., 127 g of benzyl chloride were added, in drops, to the solution while stirring. After the mixture was left to react for about six hours, the supernatant oil layer was removed and dissolved in 400 ml of toluene. The resulting solution was subjected to washing with water two or three times and to dehydration with anhydrous sodium sulfate.
- the developing solution had a pH of about 5.9.
- the development was carried out rapidly, and the obtained copy had an image of black in color.
- the half tone areas of the image obtained were consistent in color with the maximum density areas of this reproduced im age.
- EXAMPLE-2 A support for use in ordinary diazotype lightscnsitive copying materials was coated with a sensitizing solution of the following composition:
- Ethyleneglycol monomethylether 20 Formic acid 3 g Water 35 g Iso-propanol 40 g Citric acid 3 g Cresyl glutaric acid 2 g 4-dibenzylamino-2-methyl-S-(B-ethoxy) ethoxy benzene diazonium compound, zinc chloride double salt (Refer to Formula 6) 4 g was applied to an acetyl cellulose sheet and was dried. Development was conducted with an ammonia gas in a manner similar to that of Example 2, and a copy yellow in color was obtained. This copy could be used as a good intermediate original since it has a property to intensively absorb ultraviolet rays and the rays locating in the regions near thereof.
- a light-sensitive copying material for the diazotype process comprising a support and a photosensitive layer coated on said support, said layer comprising a diazonium compound having the formula:
- R is selected from the group consisting of hydroxyl, alkoxy having from one to four carbon atoms, a group of the formula in which R, is alkylene having from one to four car- 5 bon atoms, aryloxy,
- N and n is an integer between one and four;
- X represents an anionic radical
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5581966 | 1966-08-26 | ||
| JP7776166 | 1966-11-29 | ||
| JP7776266 | 1966-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3769021A true US3769021A (en) | 1973-10-30 |
Family
ID=27295716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00115057A Expired - Lifetime US3769021A (en) | 1966-08-26 | 1971-02-12 | Light-sensitive diazotype copying material |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3769021A (enrdf_load_stackoverflow) |
| DE (1) | DE1597621A1 (enrdf_load_stackoverflow) |
| NL (1) | NL6711736A (enrdf_load_stackoverflow) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB867630A (en) * | 1958-06-04 | 1961-05-10 | Grinten Chem L V D | Diazotype material |
| GB919037A (en) * | 1958-11-10 | 1963-02-20 | Grinten Chem L V D | Diazotype material |
| GB957838A (en) * | 1959-09-17 | 1964-05-13 | Grinten Chem L V D | Diazotype materials |
| US3272630A (en) * | 1962-09-26 | 1966-09-13 | Keuffel & Esser Co | Light-sensitive reproduction material containing unilaterally diazotized p-phenylene-diamine derivatives as the light sensitive substance |
| US3281246A (en) * | 1964-11-30 | 1966-10-25 | Keuffel & Esser Co | Diazotype reproduction material |
| US3379531A (en) * | 1965-03-30 | 1968-04-23 | Gen Aniline & Film Corp | Two-component heat developing diazotypes |
| GB1110835A (en) * | 1966-03-11 | 1968-04-24 | Admel Internat Ltd | One component diazotype material |
| US3442652A (en) * | 1965-03-24 | 1969-05-06 | Grinten Chem L V D | Diazonium compounds and diazotype material |
-
1967
- 1967-08-25 NL NL6711736A patent/NL6711736A/xx unknown
- 1967-08-25 DE DE19671597621 patent/DE1597621A1/de active Pending
-
1971
- 1971-02-12 US US00115057A patent/US3769021A/en not_active Expired - Lifetime
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB867630A (en) * | 1958-06-04 | 1961-05-10 | Grinten Chem L V D | Diazotype material |
| GB919037A (en) * | 1958-11-10 | 1963-02-20 | Grinten Chem L V D | Diazotype material |
| GB957838A (en) * | 1959-09-17 | 1964-05-13 | Grinten Chem L V D | Diazotype materials |
| US3272630A (en) * | 1962-09-26 | 1966-09-13 | Keuffel & Esser Co | Light-sensitive reproduction material containing unilaterally diazotized p-phenylene-diamine derivatives as the light sensitive substance |
| US3432301A (en) * | 1962-09-26 | 1969-03-11 | Keuffel & Esser Co | Reproduction material |
| US3459551A (en) * | 1962-09-26 | 1969-08-05 | Keuffel & Esser Co | Diazotype material |
| US3462271A (en) * | 1962-09-26 | 1969-08-19 | Keuffel & Esser Co | Diazotype material |
| US3281246A (en) * | 1964-11-30 | 1966-10-25 | Keuffel & Esser Co | Diazotype reproduction material |
| US3442652A (en) * | 1965-03-24 | 1969-05-06 | Grinten Chem L V D | Diazonium compounds and diazotype material |
| US3379531A (en) * | 1965-03-30 | 1968-04-23 | Gen Aniline & Film Corp | Two-component heat developing diazotypes |
| GB1110835A (en) * | 1966-03-11 | 1968-04-24 | Admel Internat Ltd | One component diazotype material |
Non-Patent Citations (2)
| Title |
|---|
| Landau, R., Fascicules 1a8 (Les diazo) , Distributed by Andrews Papers & Chem. Co. Inc., 1960, p. 30 relied on. * |
| Reproduction Paper News Bulletin, Andrew Paper & Chem. Co. Inc. No. 26, Sept. 1960. * |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6711736A (enrdf_load_stackoverflow) | 1968-02-27 |
| DE1597621A1 (de) | 1970-06-25 |
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