EP0161655B1 - Lichtempfindliches Gemisch und hiermit hergestelltes Zweikomponenten-Diazotypiematerial - Google Patents
Lichtempfindliches Gemisch und hiermit hergestelltes Zweikomponenten-Diazotypiematerial Download PDFInfo
- Publication number
- EP0161655B1 EP0161655B1 EP85105849A EP85105849A EP0161655B1 EP 0161655 B1 EP0161655 B1 EP 0161655B1 EP 85105849 A EP85105849 A EP 85105849A EP 85105849 A EP85105849 A EP 85105849A EP 0161655 B1 EP0161655 B1 EP 0161655B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- mixture
- acid
- diazonium
- film
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 239000000463 material Substances 0.000 title claims description 47
- -1 glycol ethers Chemical class 0.000 claims abstract description 27
- 239000012954 diazonium Substances 0.000 claims abstract description 24
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 20
- 239000003381 stabilizer Substances 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 16
- 239000011230 binding agent Substances 0.000 claims abstract description 13
- 239000011347 resin Substances 0.000 claims abstract description 13
- 229920005989 resin Polymers 0.000 claims abstract description 13
- JDQOQWKEOLQHKB-UHFFFAOYSA-N 4-aminobenzenediazonium Chemical compound NC1=CC=C([N+]#N)C=C1 JDQOQWKEOLQHKB-UHFFFAOYSA-N 0.000 claims abstract description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007791 liquid phase Substances 0.000 claims abstract description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000654 additive Substances 0.000 claims abstract description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001298 alcohols Chemical class 0.000 claims abstract description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002576 ketones Chemical class 0.000 claims abstract description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 4
- 229920003023 plastic Polymers 0.000 claims abstract description 4
- 239000004033 plastic Substances 0.000 claims abstract description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011976 maleic acid Substances 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 claims description 15
- GVVSBXXPMFLAIY-UHFFFAOYSA-N 3-chloro-4-(dimethylamino)benzenediazonium Chemical group CN(C)C1=CC=C([N+]#N)C=C1Cl GVVSBXXPMFLAIY-UHFFFAOYSA-N 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 7
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 229940114055 beta-resorcylic acid Drugs 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- BEVFDVVCEYXZKS-UHFFFAOYSA-N 3-chloro-2-[(4-methylcyclohexyl)amino]benzenediazonium Chemical group C1CC(C)CCC1NC1=C(Cl)C=CC=C1[N+]#N BEVFDVVCEYXZKS-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 5
- TVWBPCCNPTWBCV-UHFFFAOYSA-N 2,5-dichloro-4-(diethylamino)benzenediazonium Chemical group CCN(CC)C1=CC(Cl)=C([N+]#N)C=C1Cl TVWBPCCNPTWBCV-UHFFFAOYSA-N 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- WICYMZBOCOZYPO-UHFFFAOYSA-N 3-chloro-4-[(4-methylcyclohexyl)amino]-2-(trifluoromethyl)benzenediazonium Chemical group C1CC(C)CCC1NC1=CC=C([N+]#N)C(C(F)(F)F)=C1Cl WICYMZBOCOZYPO-UHFFFAOYSA-N 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 3
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 150000002688 maleic acid derivatives Chemical class 0.000 claims 1
- BDZFZYIJGYTQJF-UHFFFAOYSA-N n-(4-chlorophenyl)-6,7-dihydroxynaphthalene-2-sulfonamide Chemical compound C1=C2C=C(O)C(O)=CC2=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1 BDZFZYIJGYTQJF-UHFFFAOYSA-N 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 229920006267 polyester film Polymers 0.000 claims 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 41
- 239000010410 layer Substances 0.000 description 30
- 239000000523 sample Substances 0.000 description 28
- 238000003860 storage Methods 0.000 description 25
- 238000011161 development Methods 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 18
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 16
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 14
- 230000008878 coupling Effects 0.000 description 13
- 238000010168 coupling process Methods 0.000 description 13
- 238000005859 coupling reaction Methods 0.000 description 13
- 230000003595 spectral effect Effects 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000003973 paint Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 230000000007 visual effect Effects 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 8
- 239000004922 lacquer Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000011592 zinc chloride Substances 0.000 description 8
- 235000005074 zinc chloride Nutrition 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical compound N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000008199 coating composition Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 150000008049 diazo compounds Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000004377 microelectronic Methods 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
- 238000002360 preparation method Methods 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 2
- DWFCHZICMJZWLA-UHFFFAOYSA-M 2,5-dichloro-4-(diethylamino)benzenediazonium;chloride Chemical compound [Cl-].CCN(CC)C1=CC(Cl)=C([N+]#N)C=C1Cl DWFCHZICMJZWLA-UHFFFAOYSA-M 0.000 description 2
- SMUQBZWEOVOJBT-UHFFFAOYSA-M 3-chloro-2-[(4-methylcyclohexyl)amino]benzenediazonium;chloride Chemical compound [Cl-].C1CC(C)CCC1NC1=C(Cl)C=CC=C1[N+]#N SMUQBZWEOVOJBT-UHFFFAOYSA-M 0.000 description 2
- BSWUZGFRQRJZHF-UHFFFAOYSA-M 5-chloro-2-(4-chlorophenoxy)-4-(dimethylamino)benzenediazonium;chloride Chemical compound [Cl-].C1=C(Cl)C(N(C)C)=CC(OC=2C=CC(Cl)=CC=2)=C1[N+]#N BSWUZGFRQRJZHF-UHFFFAOYSA-M 0.000 description 2
- JSJWPZQTZMQSNU-UHFFFAOYSA-N 5-chloro-3-[(4-methylcyclohexyl)amino]-2-(trifluoromethyl)benzenediazonium Chemical class C1CC(C)CCC1NC1=CC(Cl)=CC([N+]#N)=C1C(F)(F)F JSJWPZQTZMQSNU-UHFFFAOYSA-N 0.000 description 2
- UYDCTZQIQKGSFR-UHFFFAOYSA-M 5-chloro-3-[(4-methylcyclohexyl)amino]-2-(trifluoromethyl)benzenediazonium;chloride Chemical compound [Cl-].C1CC(C)CCC1NC1=CC(Cl)=CC([N+]#N)=C1C(F)(F)F UYDCTZQIQKGSFR-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229920001079 Thiokol (polymer) Polymers 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001808 coupling effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011265 semifinished product Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical class CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- HHSJOVPBCHTADG-UHFFFAOYSA-N 2,4-dihydroxy-n-(2-hydroxyethyl)benzamide Chemical compound OCCNC(=O)C1=CC=C(O)C=C1O HHSJOVPBCHTADG-UHFFFAOYSA-N 0.000 description 1
- IIUJCQYKTGNRHH-UHFFFAOYSA-N 2,4-dihydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C=C1O IIUJCQYKTGNRHH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
- YZBOVSFWWNVKRJ-UHFFFAOYSA-M 2-butoxycarbonylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C([O-])=O YZBOVSFWWNVKRJ-UHFFFAOYSA-M 0.000 description 1
- NKLBYYMGOBDYTD-UHFFFAOYSA-M 2-chloro-4-(diethylamino)benzenediazonium;chloride Chemical compound [Cl-].CCN(CC)C1=CC=C([N+]#N)C(Cl)=C1 NKLBYYMGOBDYTD-UHFFFAOYSA-M 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- IDKVEVLVFDDQNC-UHFFFAOYSA-N 3-chloro-4-(diethylamino)benzenediazonium Chemical compound CCN(CC)C1=CC=C([N+]#N)C=C1Cl IDKVEVLVFDDQNC-UHFFFAOYSA-N 0.000 description 1
- QWLGFENJLDJBTA-UHFFFAOYSA-M 3-chloro-4-(dimethylamino)benzenediazonium;chloride Chemical compound [Cl-].CN(C)C1=CC=C([N+]#N)C=C1Cl QWLGFENJLDJBTA-UHFFFAOYSA-M 0.000 description 1
- BEEXFCOGVZELQD-UHFFFAOYSA-M 3-chloro-4-(dimethylamino)benzenediazonium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CN(C)C1=CC=C([N+]#N)C=C1Cl BEEXFCOGVZELQD-UHFFFAOYSA-M 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- ZROJVECWKBBTAE-UHFFFAOYSA-M 4-aminobenzenediazonium;hydrogen sulfate Chemical class OS([O-])(=O)=O.NC1=CC=C([N+]#N)C=C1 ZROJVECWKBBTAE-UHFFFAOYSA-M 0.000 description 1
- GCNIEGHLVCGBRA-UHFFFAOYSA-N 4-bromo-3,5-dihydroxybenzamide Chemical compound NC(=O)C1=CC(O)=C(Br)C(O)=C1 GCNIEGHLVCGBRA-UHFFFAOYSA-N 0.000 description 1
- FQQJPMJXWNRARD-UHFFFAOYSA-N 5-chloro-2-(4-chlorophenoxy)-4-(dimethylamino)benzenediazonium Chemical compound C1=C(Cl)C(N(C)C)=CC(OC=2C=CC(Cl)=CC=2)=C1[N+]#N FQQJPMJXWNRARD-UHFFFAOYSA-N 0.000 description 1
- DKJVSIITPZVTRO-UHFFFAOYSA-N 6,7-dihydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(O)C(O)=CC2=C1 DKJVSIITPZVTRO-UHFFFAOYSA-N 0.000 description 1
- 125000005330 8 membered heterocyclic group Chemical group 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- IXVISLDFEAWETN-UHFFFAOYSA-N CC1CCC(CC1)NC=1C(=C(C=C(C1)Cl)[N+]#N)Cl Chemical class CC1CCC(CC1)NC=1C(=C(C=C(C1)Cl)[N+]#N)Cl IXVISLDFEAWETN-UHFFFAOYSA-N 0.000 description 1
- DRBIBWDOKYVNDE-UHFFFAOYSA-O CN(C1=C(C(=C(C=C1Cl)[N+]#N)C1=CC=C(C=C1)C)S)C Chemical compound CN(C1=C(C(=C(C=C1Cl)[N+]#N)C1=CC=C(C=C1)C)S)C DRBIBWDOKYVNDE-UHFFFAOYSA-O 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- MEBCDIQIDFWCIL-UHFFFAOYSA-N S(=O)(=O)(O)[O-].CN(C1=C(C(=C(C=C1Cl)[N+]#N)C1=CC=C(C=C1)C)S)C Chemical compound S(=O)(=O)(O)[O-].CN(C1=C(C(=C(C=C1Cl)[N+]#N)C1=CC=C(C=C1)C)S)C MEBCDIQIDFWCIL-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 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
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical class [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- WOLATMHLPFJRGC-UHFFFAOYSA-N furan-2,5-dione;styrene Chemical compound O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 WOLATMHLPFJRGC-UHFFFAOYSA-N 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 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
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000010421 pencil drawing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/58—Coupling substances therefor
-
- 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
-
- 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
- G03C1/60—Compositions containing diazo compounds as photosensitive substances with macromolecular additives
Definitions
- the invention relates to a light-sensitive mixture of diazonium salt, coupler, resin binder, acid stabilizer, customary additives and a liquid phase and two-component diazotype material produced therewith.
- the couplers of formula B yellow dyes are obtained which absorb only very weakly in the visual spectral range, but absorb very strongly in the ultraviolet spectral range between 330 and 450 nm. Because of this absorption behavior, the azo components of the formula B are particularly suitable for the production of two-component diazo type intermediate original materials.
- the compounds of the formulas C, D, E and F which couple to form red or blue azo dyes can be added to the azo components of the formula B.
- plastics containing acid groups with an acid number of at least 100 are used as resin binders. They are known from German Patent 2,652,942 and are copolymers, such as poly (methyl vinyl ether / maleic anhydride), poly (methyl vinyl ether / maleic acid) monoethyl ester, monoisopropyl ester, monobutyl ester or poly (styrene / maleic anhydride).
- Suitable solvents are, for example, lower alcohols, such as methanol, ethanol, isopropanol, n-butanol and / or glycol ethers, such as methyl glycol, ethyl glycol, propyl glycol, methyl triglycol, butyl triglycol, methoxybutanol, and also ketones, such as acetone, methyl ethyl ketone, methyl propyl ketone, diethyl ketone and others. and mixtures of these solvents and water.
- lower alcohols such as methanol, ethanol, isopropanol, n-butanol and / or glycol ethers, such as methyl glycol, ethyl glycol, propyl glycol, methyl triglycol, butyl triglycol, methoxybutanol
- ketones such as acetone, methyl ethyl ketone, methyl propyl ket
- a stock solution with the following composition is divided into 12 paint samples, each 50 g.
- Example 2 Is coated and dried as described in Example 1.
- the layer weight is 7.6 g / m 2 .
- the pre-coupling can be significantly reduced.
- the disadvantage of the film sample (G) thus produced is that the storage of the unprocessed film material and its development under moist, warm conditions (40 ° C./80% relative humidity of the unprocessed film and approx. 70 ° C./80% relative humidity) development) forms a clearly visible coating on the surface of the layer ("sweating").
- a glass plate is sensitized on one side with a coating composition of the following composition:
- the layer weight of each diazofilm pattern is 8 to 9 g / m 2 .
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Photoreceptors In Electrophotography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Liquid Developers In Electrophotography (AREA)
- Mirrors, Picture Frames, Photograph Stands, And Related Fastening Devices (AREA)
- Reinforcement Elements For Buildings (AREA)
- Inorganic Insulating Materials (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT85105849T ATE39771T1 (de) | 1984-05-18 | 1985-05-13 | Lichtempfindliches gemisch und hiermit hergestelltes zweikomponenten-diazotypiematerial. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843418469 DE3418469A1 (de) | 1984-05-18 | 1984-05-18 | Lichtempfindliches gemisch und hiermit hergestelltes zweikomponenten-diazotypiematerial |
| DE3418469 | 1984-05-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0161655A2 EP0161655A2 (de) | 1985-11-21 |
| EP0161655A3 EP0161655A3 (en) | 1987-05-27 |
| EP0161655B1 true EP0161655B1 (de) | 1989-01-04 |
Family
ID=6236196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP85105849A Expired EP0161655B1 (de) | 1984-05-18 | 1985-05-13 | Lichtempfindliches Gemisch und hiermit hergestelltes Zweikomponenten-Diazotypiematerial |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0161655B1 (xx) |
| JP (1) | JPS60256140A (xx) |
| AT (1) | ATE39771T1 (xx) |
| AU (1) | AU578094B2 (xx) |
| BR (1) | BR8502350A (xx) |
| CA (1) | CA1270142A (xx) |
| DE (2) | DE3418469A1 (xx) |
| DK (1) | DK161113C (xx) |
| ES (1) | ES8607574A1 (xx) |
| FI (1) | FI851954L (xx) |
| IE (1) | IE56665B1 (xx) |
| NO (1) | NO168213C (xx) |
| ZA (1) | ZA853737B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4550069A (en) * | 1984-06-11 | 1985-10-29 | American Hoechst Corporation | Positive photoresist compositions with o-quinone diazide, novolak, and propylene glycol alkyl ether acetate |
| US10034690B2 (en) | 2014-12-09 | 2018-07-31 | John A. Heflin | Spine alignment system |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3203803A (en) * | 1964-01-20 | 1965-08-31 | Tecnifax Corp | Light-sensitive diazo hexafluoro-phosphate compositions |
| US3591381A (en) * | 1967-07-31 | 1971-07-06 | Eastman Kodak Co | Stabilized diazotype composition |
| US3857896A (en) * | 1967-09-13 | 1974-12-31 | R Desjarlais | Substituted diresorcyl sulfide and sulfoxide compounds |
| US3619191A (en) * | 1967-09-13 | 1971-11-09 | Tecnifax Corp The | Diazo-type materials |
| DE2747412A1 (de) * | 1976-10-22 | 1978-04-27 | Scott Paper Co | Lichtempfindliche diazomasse fuer die diazotypie |
| DE2652942C3 (de) * | 1976-11-22 | 1979-05-31 | Hoechst Ag, 6000 Frankfurt | Zweikomponenten-Diazotypiematerial |
| DE2811981A1 (de) * | 1978-03-18 | 1979-09-27 | Hoechst Ag | 2-hydroxy-3-naphthoesaeureamide |
| DE2907446A1 (de) * | 1979-02-26 | 1980-09-04 | Hoechst Ag | Zweikomponenten-diazotypiematerial |
-
1984
- 1984-05-18 DE DE19843418469 patent/DE3418469A1/de not_active Withdrawn
-
1985
- 1985-05-10 ES ES543035A patent/ES8607574A1/es not_active Expired
- 1985-05-13 DE DE8585105849T patent/DE3567291D1/de not_active Expired
- 1985-05-13 AT AT85105849T patent/ATE39771T1/de not_active IP Right Cessation
- 1985-05-13 EP EP85105849A patent/EP0161655B1/de not_active Expired
- 1985-05-14 CA CA000481444A patent/CA1270142A/en not_active Expired - Fee Related
- 1985-05-15 NO NO851973A patent/NO168213C/no unknown
- 1985-05-16 FI FI851954A patent/FI851954L/fi not_active Application Discontinuation
- 1985-05-17 BR BR8502350A patent/BR8502350A/pt not_active IP Right Cessation
- 1985-05-17 AU AU42626/85A patent/AU578094B2/en not_active Ceased
- 1985-05-17 IE IE1243/85A patent/IE56665B1/en not_active IP Right Cessation
- 1985-05-17 ZA ZA853737A patent/ZA853737B/xx unknown
- 1985-05-17 DK DK219485A patent/DK161113C/da not_active IP Right Cessation
- 1985-05-17 JP JP60104156A patent/JPS60256140A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60256140A (ja) | 1985-12-17 |
| NO168213C (no) | 1992-01-22 |
| FI851954A0 (fi) | 1985-05-16 |
| DK219485A (da) | 1985-11-19 |
| DE3567291D1 (en) | 1989-02-09 |
| DK219485D0 (da) | 1985-05-17 |
| DE3418469A1 (de) | 1985-11-21 |
| ES543035A0 (es) | 1986-06-01 |
| BR8502350A (pt) | 1986-01-21 |
| EP0161655A3 (en) | 1987-05-27 |
| AU4262685A (en) | 1985-11-21 |
| NO168213B (no) | 1991-10-14 |
| AU578094B2 (en) | 1988-10-13 |
| CA1270142A (en) | 1990-06-12 |
| NO851973L (no) | 1985-11-19 |
| IE56665B1 (en) | 1991-10-23 |
| IE851243L (en) | 1985-11-18 |
| DK161113B (da) | 1991-05-27 |
| EP0161655A2 (de) | 1985-11-21 |
| ES8607574A1 (es) | 1986-06-01 |
| ZA853737B (en) | 1986-01-29 |
| FI851954L (fi) | 1985-11-19 |
| ATE39771T1 (de) | 1989-01-15 |
| DK161113C (da) | 1991-11-11 |
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