EP0159874A2 - Elimination des taches dans un matériel pour l'enregistrement thermique - Google Patents
Elimination des taches dans un matériel pour l'enregistrement thermique Download PDFInfo
- Publication number
- EP0159874A2 EP0159874A2 EP85302573A EP85302573A EP0159874A2 EP 0159874 A2 EP0159874 A2 EP 0159874A2 EP 85302573 A EP85302573 A EP 85302573A EP 85302573 A EP85302573 A EP 85302573A EP 0159874 A2 EP0159874 A2 EP 0159874A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- salts
- acids
- nitrate
- leuco dye
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 230000002265 prevention Effects 0.000 title description 2
- 238000001931 thermography Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 31
- 150000002823 nitrates Chemical class 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims description 36
- 150000007513 acids Chemical class 0.000 claims description 20
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 10
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 150000001721 carbon Chemical class 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 235000013877 carbamide Nutrition 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 150000003003 phosphines Chemical class 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- 150000003672 ureas Chemical class 0.000 claims description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 3
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- 229910001959 inorganic nitrate Inorganic materials 0.000 claims description 3
- 229950000688 phenothiazine Drugs 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- 230000008859 change Effects 0.000 claims description 2
- 150000003140 primary amides Chemical class 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 150000003334 secondary amides Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 150000003511 tertiary amides Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000975 dye Substances 0.000 description 29
- 238000000034 method Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- -1 proton acceptors Chemical class 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000243 solution Substances 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
- 150000001412 amines Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- JLDSOYXADOWAKB-UHFFFAOYSA-N aluminium nitrate Chemical compound [Al+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O JLDSOYXADOWAKB-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- MFUVDXOKPBAHMC-UHFFFAOYSA-N magnesium;dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MFUVDXOKPBAHMC-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- JFOBLRLJJPZPDD-VAWYXSNFSA-N 1,3,3-trimethyl-2-[(e)-2-(2,4,6-trimethoxyphenyl)ethenyl]-2h-indole Chemical compound COC1=CC(OC)=CC(OC)=C1\C=C\C1C(C)(C)C2=CC=CC=C2N1C JFOBLRLJJPZPDD-VAWYXSNFSA-N 0.000 description 1
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- XJKAJOFJNBIRHS-UHFFFAOYSA-N 2-bromo-4-[2-(5-chloro-1,3,3-trimethyl-2h-indol-2-yl)ethenyl]-n,n-dimethylaniline Chemical compound C1=C(Br)C(N(C)C)=CC=C1C=CC1C(C)(C)C2=CC(Cl)=CC=C2N1C XJKAJOFJNBIRHS-UHFFFAOYSA-N 0.000 description 1
- XNDZQQSKSQTQQD-UHFFFAOYSA-N 3-methylcyclohex-2-en-1-ol Chemical compound CC1=CC(O)CCC1 XNDZQQSKSQTQQD-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QKUKWEXDQIBITH-UHFFFAOYSA-N [2,8-bis(diethylamino)-10-phenylphenazin-5-yl]-phenylmethanone Chemical compound C12=CC=C(N(CC)CC)C=C2N(C=2C=CC=CC=2)C2=CC(N(CC)CC)=CC=C2N1C(=O)C1=CC=CC=C1 QKUKWEXDQIBITH-UHFFFAOYSA-N 0.000 description 1
- NGTSXAICYQUMTD-UHFFFAOYSA-N [2,8-bis(dimethylamino)-10-ethylphenazin-5-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2N(CC)C2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 NGTSXAICYQUMTD-UHFFFAOYSA-N 0.000 description 1
- RWPXSXGJVDDPFE-UHFFFAOYSA-N [3,7-bis(diethylamino)phenoxazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2N1C(=O)C1=CC=CC=C1 RWPXSXGJVDDPFE-UHFFFAOYSA-N 0.000 description 1
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000004075 alteration Effects 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
- 238000013459 approach Methods 0.000 description 1
- OSYLPIYJUCCMTQ-UHFFFAOYSA-O azanium;cerium(3+);nitrate Chemical compound [NH4+].[Ce+3].[O-][N+]([O-])=O OSYLPIYJUCCMTQ-UHFFFAOYSA-O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FBXVOTBTGXARNA-UHFFFAOYSA-N bismuth;trinitrate;pentahydrate Chemical compound O.O.O.O.O.[Bi+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FBXVOTBTGXARNA-UHFFFAOYSA-N 0.000 description 1
- 150000007528 brønsted-lowry bases Chemical class 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- QOYRNHQSZSCVOW-UHFFFAOYSA-N cadmium nitrate tetrahydrate Chemical compound O.O.O.O.[Cd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O QOYRNHQSZSCVOW-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- QGUAJWGNOXCYJF-UHFFFAOYSA-N cobalt dinitrate hexahydrate Chemical compound O.O.O.O.O.O.[Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O QGUAJWGNOXCYJF-UHFFFAOYSA-N 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- SZQUEWJRBJDHSM-UHFFFAOYSA-N iron(3+);trinitrate;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O SZQUEWJRBJDHSM-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- FGSLWIKEHNEHLX-UHFFFAOYSA-N lanthanum(3+) trinitrate nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[N+](=O)([O-])[O-].[La+3].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-] FGSLWIKEHNEHLX-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001960 metal nitrate Inorganic materials 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- AOPCKOPZYFFEDA-UHFFFAOYSA-N nickel(2+);dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O AOPCKOPZYFFEDA-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 150000002991 phenoxazines Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VAVIMIAZQDNXID-UHFFFAOYSA-N thorium(4+);tetranitrate;tetrahydrate Chemical compound O.O.O.O.[Th+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VAVIMIAZQDNXID-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
Definitions
- This invention relates to thermally imageable compositions and to stabilizers for these compositions.
- the leuco dyes may initially be relatively colorless, but can return to a colored form when oxidized, e.g., by air under acidic conditions or any other suitable oxidizing agent.
- leuco dyes used in color image forming systems include triarylmethanes, xanthenes, styryl dyes, and azine dyes, such as, for example, phenoxazines, phenothiazines, and phenazines.
- thermally sensitive materials of the type wherein at least one leuco dye is in reactive proximity with an inorganic nitrate salt, whereby imagewise application of heat causes said nitrate salt to oxidize said leuco dye to produce a change in color a problem may arise from premature spotting or backgrounding of the thermally sensitive material during the drying step of the manufacturing process.
- the term "spotting” means oxidation of the leuco dye to a colored dye form in random irregular spots;
- backgrounding means oxidation of the leuco dye to a colored dye form in uniform fashion, resulting in an evenly colored background. Either spotting or backgrounding can destroy the usefulness of a transparency film bearing a thermally imageable composition.
- One method for preventing spotting involves drying of the imageable coating at low temperatures. This method, however, requires long drying times, slow coating speeds, ana nigh costs, and in most cases, does not offer a practical solution to the problem.
- thermally imageable transparency films based upon combinations of leuco dyes ano nitrate salts it is essential that the thermally imageable compositions show considerable stability to the thermal effects of the manufacturing process in order to have a useful shelf life.
- This invention involves the prevention of spotting and backgrounding of transparency films bearing thermally imageable compositions that contain combinations of leuco dyes and nitrate salts. Spotting and backgrounding which often occur during the drying step of the manufacturing process can be prevented by the addition of one or more Bronsted-Lowry bases, i.e. proton acceptors, which have conjugate acids with pKa values of zero or higher. These bases have conjugate acids with Ka values equal to or less than one.
- Bronsted-Lowry bases i.e. proton acceptors
- Effective additives include amines; amine oxides; amides; ureas; salts of phosphinic, phosphonic, and phosphoric acids; phosphines; salts of carboxylic acids; oxygen acids, e.g., alcohols and phenols; thioacids, e.g. mercaptans and thiophenols; salts or complexes of carbon acids; and inorganic bases.
- Addition of one or more of those bases which have conjugate acids with pKa values of zero or above results in decreases or elimination of spotting, thus allowing an increase in the drying temperature during the drying step of the manufacturing process, further resulting in faster drying, higher coating rates, decreased moisture sensitivity, and lower manufacturing costs,
- Reduction and elimination of defects in the coated film resulting from premature dye color formation can also be brought about by adding the anti-spotting compounds of the present invention to the imaging compositions.
- compositions which are imageable by thermal energy, e.g. infrared radiation, and coated substrates prepared therefrom, which compositions comprise (1) at least one leuco dye, (2) at least one inorganic nitrate salt, (3) a polymeric binder, (4) an optional acid, and (5) at least one antispotting compound selected from the group consisting of
- R l , R 2 , and R 3 can be the same or different and represent a member of the group selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl groups having from 1 to 16 carbon atoms, substituted or unsubstituted aryl groups having up to 3 fused rings.
- the tertiary amine can have the following structure: wherein R 1 is as defined above and represents, for example, where 1 is an integer from 0 to 6, inclusive, m is an integer from 0 to 6, inclusive, and n is an integer from 0 to 6, inclusive; where 1 and m are as defined above and n' is 0 or 4; where 1 and m are as defined above, and n" is an integer from 0 to 4, inclusive; where 1' is 0 or 4, m and n" are as defined above.
- the tertiary amine can also have the following structure: wherein R l is as defined above, and R 4 represents CR 5 R 6 where R 5 and R 6 represents a member of the class from which R 1 , R 2 , and R 3 are selected, with the proviso that R 5 and R 6 need not be the same as R l , R 2, or R 3.
- the tertiary amine can further have the following structure: wherein represents, for example, where x is 0, 1, or 2, y is an integer from 0 to 8, inclusive, and z is 0, 1, or 2, and R 7 represents a member of the class from which R 1 , R 2 , and R 3 are selected, with the proviso that R 7 need not be the same as R l, R 2, R 3; wherein R l and R 2 are as defined above. wherein R 1 and R 2 are as defined above. wherein R 1 is as defined above. wherein R 1 and R 2 are as defined above. wherein R 1 , R 2 , and R 3 are as defined above. wherein R 1 , R 2 and R 3 are as defined above.
- R 1 , R 2 , and R 3 are as defined above, and R 8 represents a member of the class from which R 1 , R 2 , and R 3 are selected, with the proviso that R 8 need not be the same as R 1 , R 2 , or R 3 .
- R 1 is as defined above, and A+ represents a metallic cation, e.g. Li + , Na + , K + , Mg +2 , Ca +2 , Mn +2 , Fe +3 , Ni +2 , Cu +2 , Zn +2 .. wherein R 1 and A+ are as defined above. wherein R 1 and A+ are as defined above.
- R 9 , R 10 , and R 11 can be the same or different and represent a member of the group selected from H, -NO 2 , -CN, -COR 12 , -COOR 12 , and -SO 2 R 12 where R 12 is selected from the group consisting of phenyl group, naphthyl group, alkyl group having 1 to 4 carbon atoms, and A+ is as defined above.
- the salts or complexes of carbon acids can also include the following structures wherein R 9 and A+ are as defined above and represent, for example, wherein a is 2, 3, or 4; where b is 0 or 4.
- the salts or complexes of carbon acids can further include the following structure wherein A+ is as defined above, and R 1 3 represents the phenyl or naphthyl group. wherein R 1 , R 2 , and A + are as defined above. wherein R l , R 2 , and A+ are as defined above. wherein R 1 , R 2 , and A+ are as defined above. wherein R 1 , R 2 , and R 3 are as defined above. wherein A+ is as defined above, and Y - represents a member of the group selected from - OH , S , HS , C03 , HC 0 3.
- R l , R 2 , or R 3 is a substituted alkyl or aryl group
- substituents can be any which do not deleteriously affect the function of the thermographic system.
- Suitable substituents include halo groups, e.g. chloro, bromo, iodo, fluoro; hydroxyl group; cyano group; nitro group; alkoxy group having, for example, 1 to 20 carbon atoms; alkyl carbonyl group having, for example, 1 to 20 carbon atoms; alkylsulfonyl group, having, for example, 1 to 20 carbon atoms.
- R 1 , R 2 , or R 3 is a substituted aryl group
- the substituent can be alkylthio, having, for example, from 1 to 20 carbon atoms.
- R 1 , R 2 , R 3 can be mono-, di-, tri-, or tetra- substituted.
- Dye classes which can be stabilized by the bases include styryl, phenoxazine, phenothiazine, and phenazine.
- styryl dyes are (a) 2,3-dihydro-1,3,3-trimethyl-2-[2-(2,4,6-trimethoxyphenyl)ethenyl]-1H-Indole; (b) 2-bromo-4-[2-(5-chloro-2,3-dihydro-1,3,3-trimethyl-lH-indol-2-yl)ethenyl]-N,N-dimethylbenzenamine; (c) 2,3-dihydro-1,3,3-trimethyl-2-[2-(4-dimethylamino)-phenyl-ethenyl]-lH-Indole; (d) 2,3-dihydro-1,3,3-trimethyl-2-[2-(4-N-morpholino-)phenyl-ethenyl]
- phenoxazine and phenothiazine dyes are: (f) 3,7-bis-(N,N-diethylamino)-10-benzoyl-phenoxazine and (g) 3,7-bis-(N,N-dimethylamino)-10-benzoyl-phenothiazine, respectively.
- phenazine dyes are; (h) 5,10-di- hydro-5-phenyl-10-benzoyl-3,7-bis-(N,N-diethylamino)phenazine and (i) 5,10-dihydro-5-ethyl-10-benzoyl-3,7-bis-(N,N-dimethylamino)phenazine.
- Nitrate salts suitable for this invention are themselves well known. They may be supplied as various chemical compounds, but are desirably provided as a metal salt, and most preferably provided as a hydrated metal salt. Most means of supplying the nitrate salt into the imaging composition are satisfactory. For example, organic salts, metal salts, acid salts, mixtures of acids and salts, and other means of supplying the ion are useful. Nitrates of zinc, cadmium, potassium, calcium, zirconyl (zr0 2 ), nickel, aluminum, chromium, iron, copper, tin, magnesium, lead, and cobalt, ammonium nitrate, and cerous ammonium nitrate can be used.
- the nitrate salt component of the present invention must be present in a form within the imaging composition so that oxidant (i.e., decomposition products of the nitrate) will be provided within the composition when it is heated to a temperature no greater than 200°F (93°C) for 60 seconds and preferably no greater than 160°F (71°C) for 60 or most preferably 30 seconds.
- the salt must be chosen so that the cation thereof is non-reactive with the leuco dye.
- non-reactive salts are defined as those salts the cations of which do not spontaneously oxidize the dyes that they are associated with at room temperature.
- Preferred salts are the hydrated metal salts such . as nickel nitrate hexahydrate, magnesium nitrate hexahydrate, aluminum nitrate nonahydrate, ferric nitrate nonahydrate, cupric nitrate trihydrate, zinc nitrate hexahydrate, cadmium nitrate tetrahydrate, bismuth nitrate pentahydrate, thorium nitrate tetrahydrate, cobalt nitrate hexahydrate, gadolinium or lanthanum nitrate nonahydrate, and mixtures of these hydrated nitrates.
- Nonhydrated or organic nitrates may be admixed therewith.
- nitrate ion per mole of dye It is preferred to have at least 0.10 mole of nitrate ion per mole of dye. It is more preferred to have at least 0.30 or 0.50 mole of nitrate ion per mole of dye.
- the bases described in this invention can be used at as low a concentration as 0.05 equivalent of base per equivalent of nitrate ion, or as high as 1.0 equivalent of base per equivalent of nitrate ion.
- the preferred range is from about 0.3 to about 0.6 equivalent of base per equivalent of nitrate ion.
- the thormally stimulated oxidation of the leuco dye by the nitrate salt can be facilitated by the presence of an acid.
- the acids optionally useful in the thermographic system of this invention are acids as generally known to the skilled chemist.
- Organic acids, preferably those having carboxylic groups, such as phthalic acid, are preferred, but inorganic acids can also be used.
- the acid can be present in a ratio of from 0 to 10 times the amount of the nitrate ion.
- the binder be selected from polymeric materials.
- Such resins as polyvinyl acetals, e.g., polyvinyl butyral, polyVinyl resins: polyvinylpyrrolidone, polyesters, polycarbonates, polyamides, polyacrylates, cellulose esters, copolymers and blends of these classes of resins, can be used. Saran, a vinyl chloride-vinylidene chloride copolymer, is particularly preferred. Natural polymeric materials such as gelatin and gum arabic can also be used.
- the leuco dye should be present at a concentration of at least 0.3% by weight, based on the weight of the binder, preferably at a concentration of at least 1% by weight, based on the weight of the binder, and most preferably at a concentration of from 2 to 10% or more by weight, based on the weight of the binder.
- a formulation which can be applied by conventional coating techniques can be produced by dissolving the leuco dye, the metal nitrate, and the polymeric binder, together with an organic acid, and, optionally, a conventional stabilizing compound, e.g. catechol, phenidone, along with the base whose conjugate acid has the required pKa in an inert organic solvent, such as, for example, acetone, methyl ethyl ketone, or tetrahydrofuran.
- a conventional stabilizing compound e.g. catechol, phenidone
- the formulation can be coated onto a support by methods well known in the art, such as, for example, wire-wound rod, knife, or extrusion coating.
- Typical wet thickness of the layer can range from about 10 to about 100 micrometers ( m), and the layer can be dried in forced air at temperatures ranging from 20°C to 50°C. It is preferred that the coating thickness be selected to provide maximum image densities greater than 0.2, and more preferably in the range of 0.5 to 1.5, as measured on a MacBeth Color Densitometer Model TD 504 using the color filter complementary to the dye color.
- the support material can be selected from a wide range of materials, including paper, glass, polymeric film, and the like, depending upon the particular imaging requirement.
- Preferred materials include polymers having good heat stability, such as polyesters.
- a particularly preferred polyester is polyethylene terephthalate.
- the additive is less effective as an antispotting agent.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US60047484A | 1984-04-16 | 1984-04-16 | |
US600474 | 1990-10-19 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0159874A2 true EP0159874A2 (fr) | 1985-10-30 |
EP0159874A3 EP0159874A3 (en) | 1986-06-04 |
EP0159874B1 EP0159874B1 (fr) | 1991-07-24 |
Family
ID=24403749
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP85302573A Expired - Lifetime EP0159874B1 (fr) | 1984-04-16 | 1985-04-12 | Elimination des taches dans un matériel pour l'enregistrement thermique |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0159874B1 (fr) |
JP (1) | JPH0671823B2 (fr) |
AU (1) | AU580034B2 (fr) |
BR (1) | BR8501734A (fr) |
CA (1) | CA1236299A (fr) |
DE (1) | DE3583524D1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994009992A1 (fr) * | 1992-10-23 | 1994-05-11 | Polaroid Corporation | Milieu et procede d'enregistrement d'image thermosensible |
EP2033801A1 (fr) * | 2007-09-10 | 2009-03-11 | Mitsubishi HiTec Paper Flensburg GmbH | Matériau d'enregistrement sensible à la chaleur |
Citations (12)
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US3460964A (en) * | 1964-11-19 | 1969-08-12 | Eastman Kodak Co | Heat-sensitive recording element and composition |
US3767449A (en) * | 1970-09-28 | 1973-10-23 | Fuji Photo Film Co Ltd | Recording sheet |
DE2355184A1 (de) * | 1972-11-08 | 1974-05-16 | Mitsubishi Paper Mills Ltd | Waermeempfindliches aufzeichnungsmaterial |
US4032690A (en) * | 1975-01-24 | 1977-06-28 | Mitsubishi Paper Mills, Ltd. | Thermosensitive recording material |
WO1981001757A1 (fr) * | 1979-12-07 | 1981-06-25 | Minnesota Mining & Mfg | Systeme photographique en couleur |
FR2494707A1 (fr) * | 1980-11-27 | 1982-05-28 | Pilot Ink Co Ltd | Matieres thermochromiques |
JPS5798392A (en) * | 1980-12-10 | 1982-06-18 | Toppan Printing Co Ltd | Thermosensitive recording |
FR2503729A1 (fr) * | 1981-04-08 | 1982-10-15 | Pilot Ink Co Ltd | Substances thermochroiques |
AT372910B (de) * | 1980-10-28 | 1983-11-25 | Manuel Ing Cespon | Beschichtungsmassen zur herstellung eines druck- empfindlichen aufzeichungsmaterials |
US4423139A (en) * | 1980-12-22 | 1983-12-27 | Minnesota Mining And Manufacturing Company | Stabilizer combination for dye oxidation |
FR2538309A1 (fr) * | 1982-12-27 | 1984-06-29 | Pilot Ink Co Ltd | Materiau d'enregistrement thermosensible reversible |
EP0124296A1 (fr) * | 1983-04-05 | 1984-11-07 | Minnesota Mining And Manufacturing Company | Système thermographique utilisant des colorants leucophénazine naphtoylés |
Family Cites Families (2)
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US4423137A (en) * | 1980-10-28 | 1983-12-27 | Quixote Corporation | Contact printing and etching method of making high density recording medium |
US4379835A (en) * | 1980-12-22 | 1983-04-12 | Minnesota Mining And Manufacturing Company | Black image from a thermographic imaging system |
-
1985
- 1985-03-07 CA CA000475897A patent/CA1236299A/fr not_active Expired
- 1985-03-13 AU AU39800/85A patent/AU580034B2/en not_active Ceased
- 1985-04-12 EP EP85302573A patent/EP0159874B1/fr not_active Expired - Lifetime
- 1985-04-12 BR BR8501734A patent/BR8501734A/pt not_active IP Right Cessation
- 1985-04-12 DE DE8585302573T patent/DE3583524D1/de not_active Expired - Fee Related
- 1985-04-15 JP JP60080044A patent/JPH0671823B2/ja not_active Expired - Lifetime
Patent Citations (12)
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US3460964A (en) * | 1964-11-19 | 1969-08-12 | Eastman Kodak Co | Heat-sensitive recording element and composition |
US3767449A (en) * | 1970-09-28 | 1973-10-23 | Fuji Photo Film Co Ltd | Recording sheet |
DE2355184A1 (de) * | 1972-11-08 | 1974-05-16 | Mitsubishi Paper Mills Ltd | Waermeempfindliches aufzeichnungsmaterial |
US4032690A (en) * | 1975-01-24 | 1977-06-28 | Mitsubishi Paper Mills, Ltd. | Thermosensitive recording material |
WO1981001757A1 (fr) * | 1979-12-07 | 1981-06-25 | Minnesota Mining & Mfg | Systeme photographique en couleur |
AT372910B (de) * | 1980-10-28 | 1983-11-25 | Manuel Ing Cespon | Beschichtungsmassen zur herstellung eines druck- empfindlichen aufzeichungsmaterials |
FR2494707A1 (fr) * | 1980-11-27 | 1982-05-28 | Pilot Ink Co Ltd | Matieres thermochromiques |
JPS5798392A (en) * | 1980-12-10 | 1982-06-18 | Toppan Printing Co Ltd | Thermosensitive recording |
US4423139A (en) * | 1980-12-22 | 1983-12-27 | Minnesota Mining And Manufacturing Company | Stabilizer combination for dye oxidation |
FR2503729A1 (fr) * | 1981-04-08 | 1982-10-15 | Pilot Ink Co Ltd | Substances thermochroiques |
FR2538309A1 (fr) * | 1982-12-27 | 1984-06-29 | Pilot Ink Co Ltd | Materiau d'enregistrement thermosensible reversible |
EP0124296A1 (fr) * | 1983-04-05 | 1984-11-07 | Minnesota Mining And Manufacturing Company | Système thermographique utilisant des colorants leucophénazine naphtoylés |
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Title |
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PATENT ABSTRACTS OF JAPAN, vol. 6, no. 190 (M-159) [1068], 29th September 1982; & JP - A - 57 98 392 (TOPPAN INSATSU K.K.) 10-12-1980 * |
PATENTS ABSTRACTS OF JAPAN, vol. 6, no. 190 (M-159) [1068], 29th September 1982; & JP-A-57 098 392 (TOPPAN INSATSU K.K.) 18-06-1982 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994009992A1 (fr) * | 1992-10-23 | 1994-05-11 | Polaroid Corporation | Milieu et procede d'enregistrement d'image thermosensible |
EP2033801A1 (fr) * | 2007-09-10 | 2009-03-11 | Mitsubishi HiTec Paper Flensburg GmbH | Matériau d'enregistrement sensible à la chaleur |
WO2009033589A1 (fr) * | 2007-09-10 | 2009-03-19 | Mitsubishi Hitec Paper Flensburg Gmbh | Matériau d'enregistrement thermosensible |
Also Published As
Publication number | Publication date |
---|---|
DE3583524D1 (de) | 1991-08-29 |
CA1236299A (fr) | 1988-05-10 |
EP0159874A3 (en) | 1986-06-04 |
JPH0671823B2 (ja) | 1994-09-14 |
JPS60234885A (ja) | 1985-11-21 |
EP0159874B1 (fr) | 1991-07-24 |
AU3980085A (en) | 1985-10-24 |
AU580034B2 (en) | 1988-12-22 |
BR8501734A (pt) | 1985-12-10 |
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