US3028240A - Light sensitive diazotype materials - Google Patents
Light sensitive diazotype materials Download PDFInfo
- Publication number
- US3028240A US3028240A US786920A US78692059A US3028240A US 3028240 A US3028240 A US 3028240A US 786920 A US786920 A US 786920A US 78692059 A US78692059 A US 78692059A US 3028240 A US3028240 A US 3028240A
- Authority
- US
- United States
- Prior art keywords
- light sensitive
- compound
- diazotype
- double salt
- light
- 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
Links
- 239000000463 material Substances 0.000 title claims description 33
- 150000008049 diazo compounds Chemical class 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 13
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 38
- 239000002585 base Substances 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 19
- 239000011592 zinc chloride Substances 0.000 description 19
- 235000005074 zinc chloride Nutrition 0.000 description 19
- -1 diethyl amino 2,5 di-n-butoxybenzene Chemical compound 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000012954 diazonium Substances 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 125000000217 alkyl group Chemical group 0.000 description 4
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- MJXACADUQMBDHU-UHFFFAOYSA-N 1,4-dibutoxy-2-chloro-3-nitrobenzene Chemical compound CCCCOC1=CC=C(OCCCC)C([N+]([O-])=O)=C1Cl MJXACADUQMBDHU-UHFFFAOYSA-N 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-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
- 206010034960 Photophobia Diseases 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 208000013469 light sensitivity Diseases 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002757 morpholinyl group Chemical group 0.000 description 3
- 229910017604 nitric acid Inorganic materials 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
- 125000005936 piperidyl group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- MEQYDWSLOAIEQT-UHFFFAOYSA-N 2,5-dibutoxy-1-N,1-N-diethylbenzene-1,4-diamine Chemical compound NC1=CC(=C(N(CC)CC)C=C1OCCCC)OCCCC MEQYDWSLOAIEQT-UHFFFAOYSA-N 0.000 description 2
- KGHVJZBVGOZVPN-UHFFFAOYSA-N 2,5-dibutoxyaniline Chemical compound CCCCOC1=CC=C(OCCCC)C(N)=C1 KGHVJZBVGOZVPN-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- NQBCHMBXULVRMJ-UHFFFAOYSA-N 1,4-bis(3-methylbutoxy)benzene Chemical compound CC(C)CCOC1=CC=C(OCCC(C)C)C=C1 NQBCHMBXULVRMJ-UHFFFAOYSA-N 0.000 description 1
- ZROGCHDPRZRKTI-UHFFFAOYSA-N 1,4-dibutoxybenzene Chemical compound CCCCOC1=CC=C(OCCCC)C=C1 ZROGCHDPRZRKTI-UHFFFAOYSA-N 0.000 description 1
- DJUNTUXIERFOPO-UHFFFAOYSA-N 1-(2,5-dibutoxy-4-nitrophenyl)piperidine Chemical compound [N+](=O)([O-])C1=CC(=C(C=C1OCCCC)N1CCCCC1)OCCCC DJUNTUXIERFOPO-UHFFFAOYSA-N 0.000 description 1
- GWBBWCJLQQFINH-UHFFFAOYSA-N 1-(4-nitro-2,5-dipropoxyphenyl)piperidine Chemical compound [N+](=O)([O-])C1=CC(=C(C=C1OCCC)N1CCCCC1)OCCC GWBBWCJLQQFINH-UHFFFAOYSA-N 0.000 description 1
- KUOKHAYLVCTERN-UHFFFAOYSA-M 2,5-dibutoxy-4-piperidin-1-ylbenzenediazonium chloride Chemical compound [Cl-].N1(CCCCC1)C1=CC(=C(C=C1OCCCC)[N+]#N)OCCCC KUOKHAYLVCTERN-UHFFFAOYSA-M 0.000 description 1
- LQARFKMUOUIPJD-UHFFFAOYSA-M 2-propoxybenzenediazonium chloride Chemical compound [Cl-].C(CC)OC1=C(C=CC=C1)[N+]#N LQARFKMUOUIPJD-UHFFFAOYSA-M 0.000 description 1
- MKVBADWWJFSRRK-UHFFFAOYSA-N 4-(2,5-dibutoxy-4-nitrophenyl)morpholine Chemical compound CCCCOC1=CC([N+]([O-])=O)=C(OCCCC)C=C1N1CCOCC1 MKVBADWWJFSRRK-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- CGAVVSDFUOLEJN-UHFFFAOYSA-N C(CC(C)C)OC1=C(C=C(OCCC(C)C)C=C1)Cl Chemical compound C(CC(C)C)OC1=C(C=C(OCCC(C)C)C=C1)Cl CGAVVSDFUOLEJN-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 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 1
- 238000007792 addition Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229960003116 amyl nitrite Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- G03C1/54—Diazonium salts or diazo anhydrides
Definitions
- diazotype processes used for the-reproduction of documents two methods of development are used, the so-called dry development with gaseous ammonia and the so-called semi-wet development with alkaline solutions containing among other things the azo-dye coupling component or coupler. Consequently, there are also two types of light sensitivematerial suitable for the diazotype reproduction processes, namely, two component material for the dry development process and one component material for the wet development process. It is understood that the two essential components are the light sensitive diazo compound and the azo dye coupling component. In the case of the semi-wet materials, the azo dye coupling component is present in the developer but not in the light sensitive material. Principally, only four groups of the many classes of diazo compounds proposed for the wet development process have become of practical importance. These are the following:
- one-component diazotype material has been found which is admirably suited to the wet-development process. It includes a diazo compound which has a suitably high light sensitivity about twice as high as the types included under 1, 2 and 4 above as well as a suitably high coupling capacity and a relative low water solubility so it will not run or bleed in the developing solution.
- a diazo compound of the class of the present invention can be used to form the m'uchpreferred blackline. prints.
- diazo compounds of the present invention are those corresponding to one of the following general formulae:
- R represents an alkyl residue with straight or branched chain with, at least three carbon atoms and CH CH 0R O fir-C OR GHQ-CH2 HN N H:
- contrast of the copies produced with the papers according to the invention can be made even better by known additions to the light sensitive coating or by pretreatment of the paper with synthetic resin emulsions and/or finely divided silica or with casein and starch.
- Examples 1 Base paper of the kind commonly used for diazotype paper is coated with a solution containing in each liter of water 3 g. of gelatine g. of citric acid 5 g. of aluminum sulphate g. of glycol 10 cc. of alcohol g. of the zinc chloride double salt of the compound 4- diethylamino-2, S-di-n-butoxy-benzene-ldiazonium chloride and is then dried.
- the zinc chloride double salt of 4-diethyl-amino- 2, 5- di-n-butoxy-benzene-l-diazonium chloride is obtained as follows: I i
- Aminohydroquinone-di-n-butylether is twice directly ethylated with diethyl sulphate, consecutively, without solvent.
- the oily diethylamino-bydroquinone-di-n-butylether thus obtained boils at 182-l85 C. under 9 mm. of mercury.
- This base is coupled in glacial acetic acid.
- the dyestufi' produced is isolated and subjected to reduction with sodium carbonate and hydrosulphite.
- the 4- amino-2,5-di-n-butoxy-diethylaniline thus obtained is diazotised and can be satisfactorily isolated in the form of, for example, the zinc double salt.
- hydroquinone-di-n-butylether is nitrated in aqueous nitric acid.
- the nitro compound separates as a yellow oil, which is subjected to a vacuum distillation and which boils at a temperature of 208 to 209 C. at a pressure of a 12 mm. mercury.
- the corresponding amino compound is obtained, which boils in a vacuum at a temperature of 190 to 191 C. (9 mm. mercury).
- the dipropyl compound is coupled in glacial acetic acid with a suitable diazotized aromatic amine, e.g. diazotized sulphanilic acid, to give a dyestufi.
- a suitable diazotized aromatic amine e.g. diazotized sulphanilic acid
- the oily diazo compound is dissolved in water and separated by means of zinc chloride as a crystalline yellow zinc chloride double salt.
- chloronitro hydroquinone di n-butylether is heated for 5 hours with an excess of dimethylamine to a temperature of C. in an autoclave.
- the reaction product is transformed into the corresponding hydrochloride, reconverted into the free base and finally recrystallized from alcohol.
- the purified reaction product melts at a temperature of 63 to 64 C.
- the nitro group is catalytically reduced in an autoclave and an oily base (boiling point 202 to 204 C. at 9 mm. mercury) is obtained.
- This base is diazotized in a solution of hydrochloric acid and by adding zinc chloride, the zinc chloride double salt is separated as a yellow powder.
- the diazo compound containing two butoxy groups instead of the two propoxy groups in the 2,5 positions can be used with equally good results for the preparation of the one-component coating.
- 4 morpholino 2,5 di-n-butoxy-benzene-l-diazonium chloride can be prepared in analogous manner.
- the nitro component obtainable from the chlorhydroquinonedi-n-butylether by nitration with aqueous nitric acid melts at 8l-82 C.
- the morpholine ring is introduced by simple heating of the chlornitro-hydroquinone-di-n-butylether with the base.
- the melting point of the 4-nitro-2,5-di-n-butoxyphenyl morpholine is about 101-102" C. Reduction and diazotisation follow.
- the chloronitro-hydroquinone-di n propyl ether is boiled for several hours with aqueous piperidine until the reaction is quantitatively complete (about 10 hours).
- the 4-nitro-2,5- di-n-propoxyphenyl-piperidine which had been separated by diluting the reaction mixture with water, melts at a temperature of 80 to 81 C.
- the compound is reduced in hydrochloric acid to which a small quantity of ethyl alcohol has been added by means oi'zinc dust.
- the diazotisation takes place in aknown manner and results the crystallization of beautiful crystals of the zinc chloride double salt of the diazo compound.
- the 4-nitro-2,5-di-(isoamyloxy-phenyl)-morpholine that crystallizes out is isolated, reduced and diazotised.
- This compound is preferably precipitated in the form of the hydrochloride because the zinc salt is insufiiciently soluble.
- either of the homologous diazo compounds may be used, which in the 2,5 positions contain two isobutoxy groups or two isopropoxy groups, respectively, instead of the two isoamyloxy groups. Both compounds are prepared analogously to the preparation of the isoamyl compound described above.
- R is alkyl containing 3 to 5 carbon atoms
- R and R are alkyl groups containing 1 to 3 carbon atoms
- V c is a saturated heterocyclic group selected from the group consisting of morpholinyl and piperidyl.
- a light sensitive diazotype material of the single component type comprising a base material coated with a. light sensitive composition including a light sensitive diazo compound formed from a p-phenylene diamine of the general formula:
- R is alkyl containing 3 to 5 carbon atoms
- I l o is a saturated heterocyclic group selected from the group consisting of morpholinyl and piperidyl.
- a light-sensitive one component diazotype material comprising a base material coated with a light'sensitive composition including a light-sensitive diazo compound which is the product of diazotization of a compound of the formula where is a saturated heterocyclic group selected from the group consisting of morpholinyl and piperidyl.
- a light sensitive diazotype material of the single component type comprising a base material coated with a. light sensitive composition including a light sensitive diazo compound formed from a p-phenylenediamine of the general formula:
- a light sensitive diazotype material of the single component type comprising a base material coated with a light sensitive composition including a light sensitive diazo compound of 4-morpholine-2,5-di-iso-butoXy-benzene-l-amine.
- a light sensitive diazotype material of the single component type comprising a base material coated with a light sensitive composition including a light sensitive diazo compound of 4-morpholine-2,S-di-iso-propoxybenzene-l-amine.
- a light sensitive diazotype material of the single component type comprising a base material coated with a light sensitive composition including a light sensitive diazo compound of 4-piperidino-Z,S-di-n-butoxy-benzenel-amine.
- a light sensitive diazotype material of the single component type comprising a base material coated with a light sensitive composition including a light sensitive cliazo compound of 4-dimethylamino 2,5-di-n-butoxybenzene-l-amine.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK33853A DE1086123B (de) | 1958-01-18 | 1958-01-18 | Einkomponenten-Diazotypiematerial |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3028240A true US3028240A (en) | 1962-04-03 |
Family
ID=7219855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US786920A Expired - Lifetime US3028240A (en) | 1958-01-18 | 1959-01-15 | Light sensitive diazotype materials |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3028240A (en)) |
| BE (1) | BE574785A (en)) |
| CH (1) | CH373956A (en)) |
| DE (1) | DE1086123B (en)) |
| FR (1) | FR1220984A (en)) |
| GB (1) | GB853020A (en)) |
| IT (1) | IT601676A (en)) |
| NL (2) | NL113082C (en)) |
| NO (1) | NO98358A (en)) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3113025A (en) * | 1960-03-02 | 1963-12-03 | Gen Aniline & Film Corp | Diazotype materials for the production of black images |
| US3139341A (en) * | 1960-12-09 | 1964-06-30 | Keuffel & Esser Co | Two component diazotype layers comprising a di-alkyl [piperazino-methyl]-phenol coupling compound |
| US3199981A (en) * | 1959-07-29 | 1965-08-10 | Azoplate Corp | Light sensitive layers |
| US3281245A (en) * | 1962-03-09 | 1966-10-25 | Keuffel & Esser Co | Diazotype material |
| US3353984A (en) * | 1963-04-18 | 1967-11-21 | Landau Raphael | Method for the preparation of lightsensitive diazotype materials and improved materials prepared by such method |
| US3382070A (en) * | 1964-01-02 | 1968-05-07 | Gen Aniline & Film Corp | Black-line moist diazotype process |
| US3404005A (en) * | 1963-10-01 | 1968-10-01 | Ind Dyestuff Company | Diazo light-sensitive composition and element |
| US3406072A (en) * | 1964-12-21 | 1968-10-15 | Gaf Corp | One-component diazotypes |
| US3407066A (en) * | 1963-06-18 | 1968-10-22 | Gaf Great Britain Ltd | Light sensitive diazonium compounds and diazotype materials |
| US3497355A (en) * | 1968-01-11 | 1970-02-24 | Gaf Corp | Diazotype reproduction material comprising a diazonium compound and method of use |
| US3520692A (en) * | 1965-07-02 | 1970-07-14 | Grinten Chem L V D | Diazonium compounds and diazotype materials containing them |
| US3868255A (en) * | 1969-07-23 | 1975-02-25 | Gaf Corp | Diazonium salts and diazotype materials |
| US3970460A (en) * | 1973-03-28 | 1976-07-20 | Multitec Ag | Diazotype composition |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE600885A (en)) * | 1960-03-04 | |||
| US3401038A (en) * | 1964-03-06 | 1968-09-10 | Gaf Corp | Diazotype materials containing polycyclic light-sensitive fluorene diazonium salts |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2113944A (en) * | 1933-09-11 | 1938-04-12 | Dietzgen Eugene Co | Production of photographic diazotype prints |
| US2215739A (en) * | 1938-01-07 | 1940-09-24 | Dietzgen Co Eugene | Light sensitive diazo-type layers and method of use and production |
| US2405523A (en) * | 1944-08-09 | 1946-08-06 | Du Pont | Light-sensitive photographic compositions and elements |
| US2551133A (en) * | 1946-08-29 | 1951-05-01 | Du Pont | Photographic light-sensitive diazo element |
| US2792303A (en) * | 1951-09-19 | 1957-05-14 | Grinten Chem L V D | Process for the production of diazotype copies |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE832396C (de) * | 1950-01-17 | 1952-02-25 | Kalle & Co Ag | Lichtempfindliche Schichten fuer die Diazotypie |
-
0
- NO NO98358D patent/NO98358A/no unknown
- NL NL235161D patent/NL235161A/xx unknown
- BE BE574785D patent/BE574785A/xx unknown
- IT IT601676D patent/IT601676A/it unknown
- NL NL113082D patent/NL113082C/xx active
-
1958
- 1958-01-18 DE DEK33853A patent/DE1086123B/de active Pending
-
1959
- 1959-01-12 GB GB1114/59A patent/GB853020A/en not_active Expired
- 1959-01-13 CH CH6827259A patent/CH373956A/de unknown
- 1959-01-15 FR FR784068A patent/FR1220984A/fr not_active Expired
- 1959-01-15 US US786920A patent/US3028240A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2113944A (en) * | 1933-09-11 | 1938-04-12 | Dietzgen Eugene Co | Production of photographic diazotype prints |
| US2215739A (en) * | 1938-01-07 | 1940-09-24 | Dietzgen Co Eugene | Light sensitive diazo-type layers and method of use and production |
| US2405523A (en) * | 1944-08-09 | 1946-08-06 | Du Pont | Light-sensitive photographic compositions and elements |
| US2551133A (en) * | 1946-08-29 | 1951-05-01 | Du Pont | Photographic light-sensitive diazo element |
| US2792303A (en) * | 1951-09-19 | 1957-05-14 | Grinten Chem L V D | Process for the production of diazotype copies |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3199981A (en) * | 1959-07-29 | 1965-08-10 | Azoplate Corp | Light sensitive layers |
| US3113025A (en) * | 1960-03-02 | 1963-12-03 | Gen Aniline & Film Corp | Diazotype materials for the production of black images |
| US3139341A (en) * | 1960-12-09 | 1964-06-30 | Keuffel & Esser Co | Two component diazotype layers comprising a di-alkyl [piperazino-methyl]-phenol coupling compound |
| US3281245A (en) * | 1962-03-09 | 1966-10-25 | Keuffel & Esser Co | Diazotype material |
| US3353984A (en) * | 1963-04-18 | 1967-11-21 | Landau Raphael | Method for the preparation of lightsensitive diazotype materials and improved materials prepared by such method |
| US3407066A (en) * | 1963-06-18 | 1968-10-22 | Gaf Great Britain Ltd | Light sensitive diazonium compounds and diazotype materials |
| US3404005A (en) * | 1963-10-01 | 1968-10-01 | Ind Dyestuff Company | Diazo light-sensitive composition and element |
| US3382070A (en) * | 1964-01-02 | 1968-05-07 | Gen Aniline & Film Corp | Black-line moist diazotype process |
| US3406072A (en) * | 1964-12-21 | 1968-10-15 | Gaf Corp | One-component diazotypes |
| US3520692A (en) * | 1965-07-02 | 1970-07-14 | Grinten Chem L V D | Diazonium compounds and diazotype materials containing them |
| US3497355A (en) * | 1968-01-11 | 1970-02-24 | Gaf Corp | Diazotype reproduction material comprising a diazonium compound and method of use |
| US3868255A (en) * | 1969-07-23 | 1975-02-25 | Gaf Corp | Diazonium salts and diazotype materials |
| US3970460A (en) * | 1973-03-28 | 1976-07-20 | Multitec Ag | Diazotype composition |
Also Published As
| Publication number | Publication date |
|---|---|
| NL235161A (en)) | |
| NO98358A (en)) | |
| DE1086123B (de) | 1960-07-28 |
| FR1220984A (fr) | 1960-05-30 |
| CH373956A (de) | 1963-12-15 |
| NL113082C (en)) | |
| BE574785A (en)) | |
| GB853020A (en) | 1960-11-02 |
| IT601676A (en)) |
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