EP1245403B1 - Matériau thermographique d'enregistrement avec ton d'image amélioré - Google Patents
Matériau thermographique d'enregistrement avec ton d'image amélioré Download PDFInfo
- Publication number
- EP1245403B1 EP1245403B1 EP20010000095 EP01000095A EP1245403B1 EP 1245403 B1 EP1245403 B1 EP 1245403B1 EP 20010000095 EP20010000095 EP 20010000095 EP 01000095 A EP01000095 A EP 01000095A EP 1245403 B1 EP1245403 B1 EP 1245403B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- recording material
- thermographic recording
- group
- dihydroxyphenyl
- thermosensitive element
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000463 material Substances 0.000 title claims description 72
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 25
- 239000003638 chemical reducing agent Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 239000011241 protective layer Substances 0.000 claims description 14
- 239000011230 binding agent Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- -1 3,4,5-trihydroxyphenyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- UCQUAMAQHHEXGD-UHFFFAOYSA-N 3',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C(O)=C1 UCQUAMAQHHEXGD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid group Chemical group C(CCCC(=O)O)(=O)O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 4
- NUWHYWYSMAPBHK-UHFFFAOYSA-N 3,4-dihydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C=C1O NUWHYWYSMAPBHK-UHFFFAOYSA-N 0.000 claims description 3
- OAYRYNVEFFWSHK-UHFFFAOYSA-N carsalam Chemical compound C1=CC=C2OC(=O)NC(=O)C2=C1 OAYRYNVEFFWSHK-UHFFFAOYSA-N 0.000 claims description 3
- ARWCZKJISXFBGI-UHFFFAOYSA-N (3,4-dihydroxyphenyl)-phenylmethanone Chemical compound C1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 ARWCZKJISXFBGI-UHFFFAOYSA-N 0.000 claims description 2
- YFURRWKTIKKJEF-UHFFFAOYSA-N 7-methoxy-1,3-benzoxazine-2,4-dione Chemical compound O1C(=O)NC(=O)C=2C1=CC(OC)=CC=2 YFURRWKTIKKJEF-UHFFFAOYSA-N 0.000 claims description 2
- HQUVXRFXGBZDNB-UHFFFAOYSA-N 7-methyl-1,3-benzoxazine-2,4-dione Chemical compound O1C(=O)NC(=O)C=2C1=CC(C)=CC=2 HQUVXRFXGBZDNB-UHFFFAOYSA-N 0.000 claims description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 claims description 2
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 23
- 238000010438 heat treatment Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 238000001931 thermography Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- AQRYNYUOKMNDDV-UHFFFAOYSA-M silver behenate Chemical compound [Ag+].CCCCCCCCCCCCCCCCCCCCCC([O-])=O AQRYNYUOKMNDDV-UHFFFAOYSA-M 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- KBPUBCVJHFXPOC-UHFFFAOYSA-N ethyl 3,4-dihydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(O)C(O)=C1 KBPUBCVJHFXPOC-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 150000003378 silver Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
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- 239000011347 resin Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000007651 thermal printing Methods 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 239000004262 Ethyl gallate Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- VFPFQHQNJCMNBZ-UHFFFAOYSA-N ethyl gallate Chemical compound CCOC(=O)C1=CC(O)=C(O)C(O)=C1 VFPFQHQNJCMNBZ-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000006224 matting agent Substances 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000005691 oxidative coupling reaction Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 description 1
- UXTZUUVTGMDXNG-UHFFFAOYSA-N 1,2-benzoxazine-3,4-dione Chemical compound C1=CC=C2C(=O)C(=O)NOC2=C1 UXTZUUVTGMDXNG-UHFFFAOYSA-N 0.000 description 1
- GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical class SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- DFZVZKUDBIJAHK-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid silver Chemical compound [Ag].OC(C(=O)O)CCCCCCCCCCCCCCCC DFZVZKUDBIJAHK-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- QRLHFJSOINAGAU-UHFFFAOYSA-N 3-methoxy-5-(2-methylphenyl)sulfonylbenzene-1,2-diol Chemical compound OC1=C(O)C(OC)=CC(S(=O)(=O)C=2C(=CC=CC=2)C)=C1 QRLHFJSOINAGAU-UHFFFAOYSA-N 0.000 description 1
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- KFIRODWJCYBBHY-UHFFFAOYSA-N 3-nitrophthalic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1C(O)=O KFIRODWJCYBBHY-UHFFFAOYSA-N 0.000 description 1
- CFUJIEQXLCNWHW-UHFFFAOYSA-N 4-methylsulfonylbenzene-1,2-diol Chemical compound CS(=O)(=O)C1=CC=C(O)C(O)=C1 CFUJIEQXLCNWHW-UHFFFAOYSA-N 0.000 description 1
- DKGIOAOFOFWSRW-UHFFFAOYSA-N 5-[1-[2-(3,4,5-trihydroxyphenyl)naphthalen-1-yl]sulfonylnaphthalen-2-yl]benzene-1,2,3-triol Chemical compound OC1=C(O)C(O)=CC(C=2C(=C3C=CC=CC3=CC=2)S(=O)(=O)C=2C3=CC=CC=C3C=CC=2C=2C=C(O)C(O)=C(O)C=2)=C1 DKGIOAOFOFWSRW-UHFFFAOYSA-N 0.000 description 1
- JTKYYVBRIVZKSP-UHFFFAOYSA-N 5-[2-[1-(3,4,5-trihydroxyphenyl)naphthalen-2-yl]sulfonylnaphthalen-1-yl]benzene-1,2,3-triol Chemical compound OC1=C(O)C(O)=CC(C=2C3=CC=CC=C3C=CC=2S(=O)(=O)C=2C(=C3C=CC=CC3=CC=2)C=2C=C(O)C(O)=C(O)C=2)=C1 JTKYYVBRIVZKSP-UHFFFAOYSA-N 0.000 description 1
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- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
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- 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
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
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- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
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- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
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- CCGGDOVGIDSGQN-UHFFFAOYSA-N benzo[f][1,2]benzoxazine-1,2-dione Chemical compound C1=CC=CC2=C(C(C(=O)NO3)=O)C3=CC=C21 CCGGDOVGIDSGQN-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- CBDBLXUJRXZQMK-UHFFFAOYSA-N butyl 3,4-dihydroxybenzoate Chemical compound CCCCOC(=O)C1=CC=C(O)C(O)=C1 CBDBLXUJRXZQMK-UHFFFAOYSA-N 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- JTXUVYOABGUBMX-UHFFFAOYSA-N didodecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCC JTXUVYOABGUBMX-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- OPTDDWCXQQYKGU-UHFFFAOYSA-N diphenyldichloromethane Chemical compound C=1C=CC=CC=1C(Cl)(Cl)C1=CC=CC=C1 OPTDDWCXQQYKGU-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical group CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- JDDMVRLFNBKGOP-UHFFFAOYSA-N ethyl 3-butoxy-4,5-dihydroxybenzoate Chemical compound CCCCOC1=CC(C(=O)OCC)=CC(O)=C1O JDDMVRLFNBKGOP-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 235000019277 ethyl gallate Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- KLZURLSQXDZBTE-UHFFFAOYSA-N methyl 3,4-dihydroxy-5-octoxybenzoate Chemical compound CCCCCCCCOC1=CC(C(=O)OC)=CC(O)=C1O KLZURLSQXDZBTE-UHFFFAOYSA-N 0.000 description 1
- GSYIWPMLTQBAJX-UHFFFAOYSA-N methyl 3,4-dihydroxy-5-propoxybenzoate Chemical compound CCCOC1=CC(C(=O)OC)=CC(O)=C1O GSYIWPMLTQBAJX-UHFFFAOYSA-N 0.000 description 1
- LRTOHZLSIQNKRI-UHFFFAOYSA-N methyl 3-butoxy-4,5-dihydroxybenzoate Chemical compound CCCCOC1=CC(C(=O)OC)=CC(O)=C1O LRTOHZLSIQNKRI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CKVOZFPOBKZYSV-UHFFFAOYSA-N naphthalen-1-yl 3-butoxy-4,5-dihydroxybenzoate Chemical compound OC1=C(O)C(OCCCC)=CC(C(=O)OC=2C3=CC=CC=C3C=CC=2)=C1 CKVOZFPOBKZYSV-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004584 polyacrylic acid Chemical class 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
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000039 preparative column chromatography Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940054334 silver cation Drugs 0.000 description 1
- YRSQDSCQMOUOKO-KVVVOXFISA-M silver;(z)-octadec-9-enoate Chemical compound [Ag+].CCCCCCCC\C=C/CCCCCCCC([O-])=O YRSQDSCQMOUOKO-KVVVOXFISA-M 0.000 description 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
- MNMYRUHURLPFQW-UHFFFAOYSA-M silver;dodecanoate Chemical compound [Ag+].CCCCCCCCCCCC([O-])=O MNMYRUHURLPFQW-UHFFFAOYSA-M 0.000 description 1
- LTYHQUJGIQUHMS-UHFFFAOYSA-M silver;hexadecanoate Chemical compound [Ag+].CCCCCCCCCCCCCCCC([O-])=O LTYHQUJGIQUHMS-UHFFFAOYSA-M 0.000 description 1
- ORYURPRSXLUCSS-UHFFFAOYSA-M silver;octadecanoate Chemical compound [Ag+].CCCCCCCCCCCCCCCCCC([O-])=O ORYURPRSXLUCSS-UHFFFAOYSA-M 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
- G03C1/498—Photothermographic systems, e.g. dry silver
- G03C1/4989—Photothermographic systems, e.g. dry silver characterised by a thermal imaging step, with or without exposure to light, e.g. with a thermal head, using a laser
-
- 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
- G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
- G03C1/498—Photothermographic systems, e.g. dry silver
- G03C1/49827—Reducing agents
-
- 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
- G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
- G03C1/498—Photothermographic systems, e.g. dry silver
- G03C1/49836—Additives
- G03C1/49845—Active additives, e.g. toners, stabilisers, sensitisers
-
- 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
- B41M5/32—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers one component being a heavy metal compound, e.g. lead or iron
Definitions
- the present invention relates to thermographic recording materials whose prints have improved thermal development efficiency.
- Thermal imaging or thermography is a recording process wherein images are generated by the use of thermal energy.
- direct thermal thermography a visible image pattern is formed by image-wise heating of a recording material.
- thermographic recording materials with improved thermal development efficiency i.e. improved D max /(organic silver salt coverage) ratios without significant deterioration in archivability of the prints obtained therewith.
- thermosensitive element containing a substantially light-insensitive organic silver salt, a 1,2-dihydroxyphenyl-compound in thermal working relationship therewith and a binder
- said 1,2-dihydroxyphenyl-compound is represented by formula (I) : R 1 SO 2 R 2 , wherein R 1 is an optionally substituted aryl group and R 2 is selected from the group consisting of a 3,4,5-trihydroxyphenyl group, a 3-alkoxy-4,5-dihydroxyphenyl group and a 3-aryloxy-4,5-dihydroxyphenyl group; or said 1,2-dihydroxyphenyl-compound is represented by formula (II): R 3 COOR 4 , wherein R 3 is a 3-alkoxy-4,5-dihydroxyphenyl group or a 3-aryloxy-4,5-dihydroxyphenyl group; and R 4 is an
- thermographic recording process for a monosheet black and white substantially light-insensitive thermographic recording material according to any of the preceding claims comprising the steps of: (i) providing the thermographic recording material; (ii) bringing the thermographic recording material into the proximity of a heat source; (iii) applying heat imagewise from the heat source to the thermographic recording material; and (iv) removing the thermographic recording material from the proximity of the heat source.
- the heat source is a thermal head.
- the heat source is a thin film thermal head.
- alkyl means all variants possible for each number of carbon atoms in the alkyl group i.e. for three carbon atoms: n-propyl and isopropyl; for four carbon atoms: n-butyl, isobutyl and tertiary-butyl; for five carbon atoms: n-pentyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl and 2-methyl-butyl etc.
- substantially light-insensitive is meant not intentionally light sensitive.
- substantially water-free condition means heating at a temperature of 80 to 250°C.
- substantially water-free condition means that the reaction system is approximately in equilibrium with water in the air, and water for inducing or promoting the reaction is not particularly or positively supplied from the exterior to the element. Such a condition is described in T.H. James, "The Theory of the Photographic Process", Fourth Edition, Macmillan 1977, page 374.
- R 1 in the compound according to formula (I) is a phenyl group optionally substituted with a chlorine or a bromine atom or an alkyl, an aryl, an alkoxy, an aryloxy, a cyano, or a nitro group.
- the alkoxy group in the 3-alkoxy-4,5-dihydroxyphenyl group option of R 2 is a methoxy, an ethoxy, a n-propoxy, an isopropoxy, a n-butoxy or a t-butoxy group.
- Suitable compounds according to formula (I) for use in the thermographic recording materials of the present invention are: R01 4-methyl-3',4',5'-trihydroxy-diphenylsulphone R02 4-ethyl-3',4',5'-trihydroxy-diphenylsulphone R03 4-n-propyl-3',4',5'-trihydroxy-diphenylsulphone R04 4-isopropyl-3',4',5'-trihydroxy-diphenylsulphone R05 3,4,5-trihydroxyphenyl-1-naphthyl-sulphone R06 3,4,5-trihydroxyphenyl-2-naphthyl-sulphone R07 4-methyl-3'-methoxy-4' ,5'-dihydroxy-diphenylsulphone R08 4-methyl-3'-methoxy-4' ,5'-dihydroxy-diphenylsulphone R09 4-ethyl-3'-methoxy-4' ,5'-dihydroxy-diphen
- the alkoxy group in the 3-alkoxy-4,5-dihydroxyphenyl group option of R 3 is a methoxy, an ethoxy, a n-propoxy, an isopropoxy, a n-butoxy, a t-butoxy or a n-octoxy group.
- the alkoxy group in the 3-aryloxy-4,5-dihydroxyphenyl group option of R 3 is substituted with an alkenyl, an ether or a sulfoaryl group.
- Suitable compounds according to formula (II) for use in the thermographic recording materials of the present invention are: R21 ethyl 3-n-butoxy-4,5-dihydroxybenzoate R22 methyl 3-n-propoxy-4,5-dihydroxybenzoate R23 methyl 3-allyloxy-4,5-dihydroxybenzoate R24 methyl 3-n-butoxy-4,5-dihydroxybenzoate R25 methyl 3-n-octoxy-4,5-dihydroxybenzoate R26 methyl 3-[2'-(phenylsulfo)]ethoxy-4,5-dihydroxybenzoate R27 n-propyl 3-allyloxy-4,5-dihydroxybenzoate R28 ethyl 3-allyloxy-4,5-dihydroxybenzoate R29 methyl 3-(2'-methoxy)ethoxy-4,5-dihydroxybenzoate R30 phenyl 3-allyloxy-4,5-dihydroxybenzoate R31 1-naphthyl 3-n-butoxy-4,5-di
- thermosensitive element as used herein is that element which contains all the ingredients which contribute to image formation.
- the thermosensitive element contains a substantially light-insensitive organic silver salt, a 1,2-dihydroxyphenyl-compound as a reducing agent therefor in thermal working relationship therewith and a binder.
- the element may comprise a layer system in which the above-mentioned ingredients may be dispersed in different layers, with the proviso that the substantially light-insensitive organic silver salt is in reactive association with the reducing agent i.e. during the thermal development process the reducing agent must be present in such a way that it is able to diffuse to the particles of substantially light-insensitive organic silver salt so that reduction to silver can occur.
- the organic silver salt is not a double organic salt containing a silver cation associated with a second cation e.g. magnesium or iron ions.
- the organic silver salt is a substantially light-insensitive silver salt of an organic carboxylic acid.
- the organic silver salt is a substantially light-insensitive silver salt of an aliphatic carboxylic acids known as a fatty acid, wherein the aliphatic carbon chain has preferably at least 12 C-atoms, e.g. silver laurate, silver palmitate, silver stearate, silver hydroxystearate, silver oleate and silver behenate, which silver salts are also called "silver soaps".
- Other silver salts of an organic carboxylic acid as described in GB-P 1,439,478, e.g. silver benzoate may likewise be used to produce a thermally developable silver image.
- Combinations of different silver salt of an organic carboxylic acids may also be used in the present invention, as disclosed in EP-A 964 300.
- Organic silver salts may be dispersed by standard dispersion techniques e.g. using ball mills, bead mills, microfluidizers, ultrasonic apparatuses, rotor stator mixers etc. have been found to be useful in this regard. Mixtures of organic silver salt dispersions produced by different techniques may also be used to obtain the desired thermographic properties e.g. of coarser and a more finely ground dispersions of organic silver salts.
- Combinations of compounds according formula (I) or formula (II) with a further reducing agent may also be used that on heating become reactive partners in the reduction of the substantially light-insensitive organic silver salt.
- thermosensitive element contains a reducing agent in addition to a compound according to formula (I) or formula (II).
- thermosensitive element further contains at least one reducing agent disclosed in EP-B 692 733 or a reducing agent disclosed in EP-A 903 625.
- the thermosensitive element further contains at least one reducing agent selected from the group consisting of 3,4-dihydroxybenzoate alkyl and aryl esters (such as ethyl 3,4-dihydroxybenzoate or n-butyl 3,4-dihydroxybenzoate), 3,4-dihydroxybenzophenone, 3,4-dihydroxy-acetophenone and 3,4-dihydroxybenzonitrile.
- a reducing agent selected from the group consisting of 3,4-dihydroxybenzoate alkyl and aryl esters (such as ethyl 3,4-dihydroxybenzoate or n-butyl 3,4-dihydroxybenzoate), 3,4-dihydroxybenzophenone, 3,4-dihydroxy-acetophenone and 3,4-dihydroxybenzonitrile.
- thermosensitive element Binder of the thermosensitive element
- the film-forming binder of the thermosensitive element may be all kinds of natural, modified natural or synthetic resins or mixtures of such resins, in which the substantially light-insensitive organic silver salt can be dispersed homogeneously either in aqueous or solvent media: e.g. cellulose derivatives such as ethylcellulose, cellulose esters, e.g.
- cellulose nitrate carboxymethylcellulose, starch ethers, galactomannan
- polymers derived from ⁇ , ⁇ -ethylenically unsaturated compounds such as polyvinyl chloride, after-chlorinated polyvinyl chloride, copolymers of vinyl chloride and vinylidene chloride, copolymers of vinyl chloride and vinyl acetate, polyvinyl acetate and partially hydrolyzed polyvinyl acetate, polyvinyl alcohol, polyvinyl acetals that are made from polyvinyl alcohol as starting material in which only a part of the repeating vinyl alcohol units may have reacted with an aldehyde, preferably polyvinyl butyral, copolymers of acrylonitrile and acrylamide, polyacrylic acid esters, polymethacrylic acid esters, polystyrene and polyethylene or mixtures thereof.
- the thermosensitive element contains a binder which does not contain additives or impurities which adversely affect the thermographic properties of the thermographic recording materials in which they are used.
- thermosensitive element further contains a so-called toning agent organic silver salt in order to obtain a neutral black image tone in the higher densities and neutral grey in the lower densities.
- Suitable toning agents are described in US 3,074,809, US 3,446,648 and US 3,844,797 and US 4,082,901.
- Other particularly useful toning agents are the heterocyclic toning compounds of the benzoxazine dione or naphthoxazine dione type as disclosed in GB 1,439,478, US 3,951,660 and US 5,599,647.
- the thermosensitive element further contains one or more toning agents selected from the group consisting of phthalazinone, benzo[e] [1,3]oxazine-2,4-dione, 7-methyl-benzo[e][1,3]oxazine-2,4-dione, 7-methoxy-benzo[e][1,3]oxazine-2,4-dione and 7-(ethylcarbonato)-benzo[e][1,3]oxazine-2,4-dione.
- phthalazinone benzo[e] [1,3]oxazine-2,4-dione
- 7-methyl-benzo[e][1,3]oxazine-2,4-dione 7-methoxy-benzo[e][1,3]oxazine-2,4-dione
- 7-(ethylcarbonato)-benzo[e][1,3]oxazine-2,4-dione
- Stabilizers may be incorporated into the substantially light-insensitive thermographic recording materials of the present invention in order to obtain improved shelf-life and reduced fogging.
- the thermosensitive element further contains at least one stabilizer selected from the group consisting of benzotriazole; substituted benzotriazoles; tetrazoles; mercaptotetrazoles, such as 1-phenyl-5-mercapto-tetrazole; and aromatic polycarboxylic acids, such as ortho-phthalic acid, 3-nitro-phthalic acid, tetrachlorophthalic acid, mellitic acid, pyromellitic acid and trimellitic acid, and anhydrides thereof.
- benzotriazole substituted benzotriazoles
- tetrazoles mercaptotetrazoles, such as 1-phenyl-5-mercapto-tetrazole
- aromatic polycarboxylic acids such as ortho-phthalic acid, 3-nitro-phthalic acid, tetrachlorophthalic acid, mellitic acid, pyromellitic acid and trimellitic acid, and anhydrides thereof.
- thermosensitive element may comprise in addition at least one optionally substituted aliphatic (saturated as well as unsaturated aliphatic and also cycloaliphatic) polycarboxylic acid and/or anhydride thereof in a molar percentage of at least 15 with respect to all the organic silver salt(s) present and in thermal working relationship therewith.
- the polycarboxylic acid may be used in anhydride form or partially esterified form on the condition that at least two free carboxylic acids remain or are available in the heat recording step.
- thermosensitive element further contains glutaric acid.
- thermographic recording materials of the present invention may contain one or more surfactants, which may be anionic, non-ionic or cationic surfactants and/or one or more dispersants.
- the recording material may contain in addition to the ingredients mentioned above other additives such as levelling agents e.g. BAYSILON TM MA (from BAYER AG, GERMANY).
- levelling agents e.g. BAYSILON TM MA (from BAYER AG, GERMANY).
- the support for the thermosensitive element according to the present invention may be transparent, translucent or opaque and is a thin flexible carrier made of transparent resin film, e.g. made of a cellulose ester, cellulose triacetate, polypropylene, polycarbonate or polyester, e.g. polyethylene terephthalate.
- transparent resin film e.g. made of a cellulose ester, cellulose triacetate, polypropylene, polycarbonate or polyester, e.g. polyethylene terephthalate.
- the support may be in sheet, ribbon or web form and subbed if need be to improve the adherence to the thereon coated thermosensitive element. It may be pigmented with a blue pigment as so-called blue-base.
- One or more backing layers may be provided to control physical properties such as curl and static.
- thermosensitive element is provided with a protective layer to avoid local deformation of the thermosensitive element and to improve resistance against abrasion.
- thermosensitive element is provided with a protective layer comprising a binder, which may be solvent-soluble, solvent-dispersible, water-soluble or water- dispersible.
- a binder which may be solvent-soluble, solvent-dispersible, water-soluble or water- dispersible.
- thermosensitive element is provided with a protective layer comprising solvent-soluble polycarbonates as binders as described in EP-A 614 769.
- the thermosensitive element is provided with a protective layer comprising a water-soluble or water-dispersible binder, as coating can be performed from an aqueous composition and mixing of the protective layer with the immediate underlayer can be avoided by using a solvent-soluble or solvent-dispersible binder in the immediate underlayer.
- the protective layer according to the present invention may be crosslinked. Crosslinking can be achieved by using crosslinking agents such as described in WO 95/12495. Solid or liquid lubricants or combinations thereof are suitable for improving the slip characteristics of the thermographic recording materials according to the present invention.
- thermosensitive element is provided with a protective layer comprising a solid thermomeltable lubricant such as those described in WO 94/11199.
- the protective layer of the thermographic recording material according to the present invention may comprise a matting agent.
- the thermosensitive element is provided with a protective layer comprising a matting agent such as described in WO 94/11198, e.g. talc particles, and optionally protrude from the protective layer.
- any layer of the recording material of the present invention may proceed by any coating technique e.g. such as described in Modern Coating and Drying Technology, edited by Edward D. Cohen and Edgar B. Gutoff, (1992) VCH Publishers Inc. 220 East 23rd Street, Suite 909 New York, NY 10010, U.S.A.
- Thermographic imaging is carried out by the image-wise application of heat either in analogue fashion by direct exposure through an image or by reflection from an image, or in digital fashion pixel by pixel either by using an infra-red heat source, for example with a Nd-YAG laser or other infra-red laser, with a substantially light-insensitive thermographic material preferably containing an infra-red absorbing compound, or by direct thermal imaging with a thermal head.
- thermal printing image signals are converted into electric pulses and then through a driver circuit selectively transferred to a thermal printhead.
- the thermal printhead consists of microscopic heat resistor elements, which convert the electrical energy into heat via Joule effect.
- the operating temperature of common thermal printheads is in the range of 300 to 400°C and the heating time per picture element (pixel) may be less than 1.0ms, the pressure contact of the thermal printhead with the recording material being e.g. 200-500g/cm 2 to ensure a good transfer of heat.
- the image-wise heating of the recording material with the thermal printing heads may proceed through a contacting but removable resin sheet or web wherefrom during the heating no transfer of recording material can take place.
- Activation of the heating elements can be power-modulated or pulse-length modulated at constant power.
- EP-A 654 355 discloses a method for making an image by image-wise heating by means of a thermal head having energizable heating elements, wherein the activation of the heating elements is executed duty cycled pulsewise.
- EP-A 622 217 discloses a method for making an image using a direct thermal imaging element producing improvements in continuous tone reproduction.
- Image-wise heating of the recording material can also be carried out using an electrically resistive ribbon incorporated into the material.
- Image- or pattern-wise heating of the recording material may also proceed by means of pixel-wise modulated ultra-sound.
- Thermographic imaging can be used for the production of reflection type prints and transparencies, in particular for use in the medical diagnostic field in which black-imaged transparencies are widely used in inspection techniques operating with a light box.
- thermosensitive element Preparation of the thermosensitive element
- thermosensitive elements of COMPARATIVE EXAMPLES 1 to 3 and INVENTION EXAMPLES 1 to 3 were produced by coating a dispersion with the following ingredients in 2-butanone onto a subbed 168 ⁇ m thick blue-pigmented polyethylene terephthalate support to produce layers with the compositions given in Table 1.
- Table 1 Invention AgB Reducing agent BL5HP T01 T02 S01 S02 S03 Oil Example nr.
- thermosensitive elements of the thermographic recording materials of COMPARATIVE EXAMPLES 1 to 3 and INVENTION EXAMPLES 1 to 3 were then coated with an aqueous composition with the following composition: * polyvinylalcohol (Polyviol TM WX 48 20 from Wacker Chemie): 2.1g/m 2 * colloidal silica (Levasil TM VP AC 4055 from Bayer AG, a 15% aqueous dispersion of colloidal silica): 1.05g/m 2 * Ultravon TM W (dispersion agent from Ciba Geigy) converted into acid form by passing through an ion exchange column: 0.075g/m 2 * silica (Syloid TM 72 from Grace) : 0.09 g/m 2 * mono[isotridecyl polyglycolether (3 EO)] phosphate Servoxyl TM VPDZ 3/100 from Servo Delden B.V.): 0.075g/m 2 * mixture of monolauryl and dilau
- thermographic recording materials COMPARATIVE EXAMPLES 1 to 3 and INVENTION EXAMPLES 1 to 3.
- thermographic recording materials of COMPARATIVE EXAMPLES 1 to 3 and INVENTION EXAMPLES 1 to 3 were printed using a DRYSTAR® 2000 printer from AGFA-GEVAERT equipped with a thin film thermal head with a resolution of 300 dpi adapted to operate with a line time of 12 ms and a maximum printing power of 82 mW/pixel (the line time being the time needed for printing one line). During this line time the print head received constant power.
- the thermal head resistors were power-modulated to produce different image densities.
- thermographic recording materials of INVENTION EXAMPLES 1 to 3 compared with those of the thermographic recording materials of COMPARATIVE EXAMPLES 1 to 3.
- Table 3 Invention Example nr.
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Claims (8)
- Matériau d'enregistrement thermographique monofeuille en noir et blanc essentiellement non photosensible comprenant un élément thermosensible et un support, ledit élément thermosensible contenant un sel d'argent organique essentiellement non photosensible, un composé de 1,2-dihydroxyphényle en relation de travail thermique avec lui et un liant, caractérisé en ce que ledit composé de 1,2-dihydroxyphényle répond à la formule (I) : R1SO2R2 dans laquelle R1 représente un groupe aryle le cas échéant substitué et R2 est choisi parmi le groupe constitué par un groupe 3,4,5-trihydroxyphényle, un groupe 3-alcoxy-4,5-dihydroxyphényle et un groupe 3-aryloxy-4,5-dihydroxyphényle ; ou bien ledit composé de 1,2-dihydroxyphényle répond à la formule (II) : R3COOR4 dans laquelle R3 représente un groupe 3-alcoxy-4,5-dihydroxyphényle ; R4 représente un groupe alkyle ou un groupe aryle.
- Matériau d'enregistrement thermographique selon la revendication 1, dans lequel ledit élément thermosensible comprend en outre un agent de réduction choisi parmi le groupe constitué par des esters alkyliques et aryliques du 3,4-dihydroxybenzoate, la 3,4-dihydroxy-benzophénone, la 3,4-dihydroxy-acétophénone et le 3,4-dihydroxy-benzonitrile.
- Matériau d'enregistrement thermographique selon l'une quelconque des revendications précédentes, dans lequel ledit élément thermosensible comprend en outre un ou plusieurs agents influençant le ton d'image choisis parmi le groupe constitué par la phtalazinone, la benzo[e][1,3]oxazine-2,4-dione, la 7-méthyl-benzo[e][1,3]oxazine-2,4-dione, la 7-méthoxy-benzo[e][1,3]oxazine-2,4-dione et la 7-(éthylcarbonato)-benzo[e][1,3]oxazine-2,4-dione.
- Matériau d'enregistrement thermographique selon l'une quelconque des revendications précédentes, dans lequel ledit élément thermosensible comprend en outre au moins un acide polycarboxylique aliphatique le cas échéant substitué et/ou un de ses anhydrides dans un pourcentage molaire d'au moins 15 par rapport à la totalité du sel/des sels d'argent organique présents et en relation de travail thermique avec ce(s) dernier(s).
- Matériau d'enregistrement thermographique selon la revendication 4, dans lequel ledit acide polycarboxylique aliphatique le cas échéant substitué et/ou ledit anhydride est l'acide glutarique.
- Matériau d'enregistrement thermographique selon l'une quelconque des revendications précédentes, dans lequel ledit sel d'argent organique n'est pas un double sel.
- Matériau d'enregistrement thermographique selon l'une quelconque des revendications précédentes, dans lequel ledit élément thermosensible est muni d'une couche de protection.
- Procédé d'enregistrement thermographique pour un matériau d'enregistrement thermographique monofeuille en noir et blanc essentiellement non photosensible selon l'une quelconque des revendications précédentes, comprenant les étapes consistant à : (i) procurer ledit matériau d'enregistrement thermographique ; (ii) amener ledit matériau d'enregistrement thermographique à proximité d'une source de chaleur ; (iii) appliquer de la chaleur en forme d'image à partir de ladite source de chaleur sur ledit matériau d'enregistrement thermographique ; et (iv) éloigner ledit matériau d'enregistrement thermographique de ladite source de chaleur.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2001625711 DE60125711T2 (de) | 2001-03-29 | 2001-03-29 | Thermographisches Aufzeichnungsmaterial mit verbessertem Bildton |
EP20010000095 EP1245403B1 (fr) | 2001-03-29 | 2001-03-29 | Matériau thermographique d'enregistrement avec ton d'image amélioré |
US10/106,172 US6774084B2 (en) | 2001-03-29 | 2002-03-26 | Thermographic recording material with improved image tone |
JP2002091930A JP3807731B2 (ja) | 2001-03-29 | 2002-03-28 | 向上した画像トーンを有するサーモグラフィ記録材料 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP20010000095 EP1245403B1 (fr) | 2001-03-29 | 2001-03-29 | Matériau thermographique d'enregistrement avec ton d'image amélioré |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1245403A1 EP1245403A1 (fr) | 2002-10-02 |
EP1245403B1 true EP1245403B1 (fr) | 2007-01-03 |
Family
ID=8176029
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP20010000095 Expired - Lifetime EP1245403B1 (fr) | 2001-03-29 | 2001-03-29 | Matériau thermographique d'enregistrement avec ton d'image amélioré |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1245403B1 (fr) |
JP (1) | JP3807731B2 (fr) |
DE (1) | DE60125711T2 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7179768B2 (en) | 2004-11-05 | 2007-02-20 | Agfa-Gevaert | Toning agents for use in thermographic recording materials |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5672560A (en) * | 1996-06-17 | 1997-09-30 | Labelon Corporation | Stabilized heat-sensitive imaging material |
EP0903625B1 (fr) * | 1997-09-17 | 2003-05-14 | Agfa-Gevaert | Matériaux d'enregistrements thermographiques |
EP0978760B1 (fr) * | 1998-08-07 | 2003-07-02 | Agfa-Gevaert | Matériaux d'enregistrements thermographiques |
-
2001
- 2001-03-29 EP EP20010000095 patent/EP1245403B1/fr not_active Expired - Lifetime
- 2001-03-29 DE DE2001625711 patent/DE60125711T2/de not_active Expired - Fee Related
-
2002
- 2002-03-28 JP JP2002091930A patent/JP3807731B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP1245403A1 (fr) | 2002-10-02 |
DE60125711D1 (de) | 2007-02-15 |
JP2002326461A (ja) | 2002-11-12 |
JP3807731B2 (ja) | 2006-08-09 |
DE60125711T2 (de) | 2007-10-25 |
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