CA2504995C - Method for forming temporary image - Google Patents
Method for forming temporary image Download PDFInfo
- Publication number
- CA2504995C CA2504995C CA002504995A CA2504995A CA2504995C CA 2504995 C CA2504995 C CA 2504995C CA 002504995 A CA002504995 A CA 002504995A CA 2504995 A CA2504995 A CA 2504995A CA 2504995 C CA2504995 C CA 2504995C
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- carbon atoms
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- image
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- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 55
- 239000000463 material Substances 0.000 claims abstract description 143
- 239000000758 substrate Substances 0.000 claims abstract description 52
- 238000003384 imaging method Methods 0.000 claims abstract description 35
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 28
- 230000001747 exhibiting effect Effects 0.000 claims abstract description 15
- 230000008859 change Effects 0.000 claims abstract description 12
- 230000031700 light absorption Effects 0.000 claims description 50
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229920003023 plastic Polymers 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 299
- 239000011358 absorbing material Substances 0.000 description 69
- 239000000123 paper Substances 0.000 description 53
- 239000011230 binding agent Substances 0.000 description 52
- 125000001424 substituent group Chemical group 0.000 description 51
- 230000009102 absorption Effects 0.000 description 43
- 238000010521 absorption reaction Methods 0.000 description 43
- 125000003118 aryl group Chemical group 0.000 description 42
- 239000010410 layer Substances 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 33
- 239000000243 solution Substances 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 29
- -1 aryl disulfide compounds Chemical class 0.000 description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 28
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 27
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 27
- 125000003545 alkoxy group Chemical group 0.000 description 27
- 125000004093 cyano group Chemical group *C#N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 125000003172 aldehyde group Chemical group 0.000 description 26
- 125000004414 alkyl thio group Chemical group 0.000 description 26
- 125000003368 amide group Chemical group 0.000 description 26
- 125000003277 amino group Chemical group 0.000 description 26
- 125000005110 aryl thio group Chemical group 0.000 description 26
- 125000004104 aryloxy group Chemical group 0.000 description 26
- 125000002843 carboxylic acid group Chemical group 0.000 description 26
- 125000004185 ester group Chemical group 0.000 description 26
- 150000004820 halides Chemical group 0.000 description 26
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
- 125000000468 ketone group Chemical group 0.000 description 26
- 150000003141 primary amines Chemical class 0.000 description 26
- 150000003335 secondary amines Chemical class 0.000 description 26
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 26
- 125000000542 sulfonic acid group Chemical group 0.000 description 26
- 150000003512 tertiary amines Chemical class 0.000 description 26
- 125000003710 aryl alkyl group Chemical group 0.000 description 25
- 238000000862 absorption spectrum Methods 0.000 description 24
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- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 16
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 16
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- 239000004926 polymethyl methacrylate Substances 0.000 description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 13
- 125000006165 cyclic alkyl group Chemical group 0.000 description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 13
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 13
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
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- 238000001035 drying Methods 0.000 description 8
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- 239000011248 coating agent Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 238000005286 illumination Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- SOXAGEOHPCXXIO-DVOMOZLQSA-N menthyl anthranilate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1N SOXAGEOHPCXXIO-DVOMOZLQSA-N 0.000 description 4
- 229960002248 meradimate Drugs 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920002050 silicone resin Polymers 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000001060 yellow colorant Substances 0.000 description 4
- YBMDPYAEZDJWNY-UHFFFAOYSA-N 1,2,3,3,4,4,5,5-octafluorocyclopentene Chemical compound FC1=C(F)C(F)(F)C(F)(F)C1(F)F YBMDPYAEZDJWNY-UHFFFAOYSA-N 0.000 description 3
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical compound C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 150000008371 chromenes Chemical class 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 230000004224 protection Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 235000021286 stilbenes Nutrition 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- PSXPTGAEJZYNFI-UHFFFAOYSA-N 1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole] Chemical compound O1C2=CC=C([N+]([O-])=O)C=C2C=CC21C(C)(C)C1=CC=CC=C1N2C PSXPTGAEJZYNFI-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 2
- IZDVWQPIYXTGIF-UHFFFAOYSA-N 8-methoxy-1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole] Chemical compound CN1C2=CC=CC=C2C(C)(C)C11C=CC(C=C(C=C2OC)[N+]([O-])=O)=C2O1 IZDVWQPIYXTGIF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000006750 UV protection Effects 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000002144 chemical decomposition reaction Methods 0.000 description 2
- 239000013626 chemical specie Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 150000001988 diarylethenes Chemical class 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000007606 doctor blade method Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
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- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 150000004053 quinones Chemical class 0.000 description 2
- 238000002310 reflectometry Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000006748 scratching Methods 0.000 description 2
- 230000002393 scratching effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000001629 stilbenes Chemical class 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- DBRIJAFRMPUNTG-UHFFFAOYSA-N (2-chlorophenyl)-phenyldiazene Chemical compound ClC1=CC=CC=C1N=NC1=CC=CC=C1 DBRIJAFRMPUNTG-UHFFFAOYSA-N 0.000 description 1
- JDNOCURWWICHSA-UHFFFAOYSA-N (2-methoxyphenyl)-phenyldiazene Chemical compound COC1=CC=CC=C1N=NC1=CC=CC=C1 JDNOCURWWICHSA-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- NLMRETTUBWEWAY-UHFFFAOYSA-N (3-methoxyphenyl)-phenyldiazene Chemical compound COC1=CC=CC(N=NC=2C=CC=CC=2)=C1 NLMRETTUBWEWAY-UHFFFAOYSA-N 0.000 description 1
- VCCPFNMAICRKLQ-UHFFFAOYSA-N (3-methylphenyl)-phenyldiazene Chemical compound CC1=CC=CC(N=NC=2C=CC=CC=2)=C1 VCCPFNMAICRKLQ-UHFFFAOYSA-N 0.000 description 1
- YDVWTPOYERGSCU-UHFFFAOYSA-N (3-nitrophenyl)-phenyldiazene Chemical compound [O-][N+](=O)C1=CC=CC(N=NC=2C=CC=CC=2)=C1 YDVWTPOYERGSCU-UHFFFAOYSA-N 0.000 description 1
- DTWXDGGIWRHTLM-FYWRMAATSA-N (3e)-3-[1-(2,5-dimethylfuran-3-yl)-2-methylpropylidene]-4-propan-2-ylideneoxolane-2,5-dione Chemical compound C1=C(C)OC(C)=C1/C(C(C)C)=C1/C(=O)OC(=O)C1=C(C)C DTWXDGGIWRHTLM-FYWRMAATSA-N 0.000 description 1
- WZSVOUYPNAGMPC-UHFFFAOYSA-N (4-ethoxyphenyl)-phenyldiazene Chemical compound C1=CC(OCC)=CC=C1N=NC1=CC=CC=C1 WZSVOUYPNAGMPC-UHFFFAOYSA-N 0.000 description 1
- PMQVUAPJLIZXCL-UHFFFAOYSA-N (4-ethylphenyl)-phenyldiazene Chemical compound C1=CC(CC)=CC=C1N=NC1=CC=CC=C1 PMQVUAPJLIZXCL-UHFFFAOYSA-N 0.000 description 1
- FZGGOXVHDTXWIK-UHFFFAOYSA-N (4-iodophenyl)-phenyldiazene Chemical compound C1=CC(I)=CC=C1N=NC1=CC=CC=C1 FZGGOXVHDTXWIK-UHFFFAOYSA-N 0.000 description 1
- LGCRPKOHRIXSEG-UHFFFAOYSA-N (4-methoxyphenyl)-phenyldiazene Chemical compound C1=CC(OC)=CC=C1N=NC1=CC=CC=C1 LGCRPKOHRIXSEG-UHFFFAOYSA-N 0.000 description 1
- GIJSVMOPNUOZBC-UHFFFAOYSA-N (4-methylphenyl)-phenyldiazene Chemical compound C1=CC(C)=CC=C1N=NC1=CC=CC=C1 GIJSVMOPNUOZBC-UHFFFAOYSA-N 0.000 description 1
- TZTDJBMGPQLSLI-UHFFFAOYSA-N (4-nitrophenyl)-phenyldiazene Chemical compound C1=CC([N+](=O)[O-])=CC=C1N=NC1=CC=CC=C1 TZTDJBMGPQLSLI-UHFFFAOYSA-N 0.000 description 1
- ZISCOWXWCHUSMH-VOTSOKGWSA-N (E)-4-nitrostilbene Chemical compound C1=CC([N+](=O)[O-])=CC=C1\C=C\C1=CC=CC=C1 ZISCOWXWCHUSMH-VOTSOKGWSA-N 0.000 description 1
- FVZHKULSULGLQK-UHFFFAOYSA-N 1',3',3'-trimethyl-5',6-dinitrospiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound C1=CC=CC2=C(N=CC3(C(C)(C)C4=CC(=CC=C4N3C)[N+]([O-])=O)O3)C3=CC([N+]([O-])=O)=C21 FVZHKULSULGLQK-UHFFFAOYSA-N 0.000 description 1
- UQSKYJFCTIZVKF-UHFFFAOYSA-N 1',3',3'-trimethyl-5'-nitrospiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound C1=CC=CC2=C(N=CC3(C(C)(C)C4=CC(=CC=C4N3C)[N+]([O-])=O)O3)C3=CC=C21 UQSKYJFCTIZVKF-UHFFFAOYSA-N 0.000 description 1
- AZZVYIDATNYVSN-UHFFFAOYSA-N 1',3',3'-trimethyl-8-nitrospiro[chromene-2,2'-indole] Chemical compound O1C(C(=CC=C2)[N+]([O-])=O)=C2C=CC21C(C)(C)C1=CC=CC=C1N2C AZZVYIDATNYVSN-UHFFFAOYSA-N 0.000 description 1
- CQTRKDFIQFOAQV-UHFFFAOYSA-N 1',3',3'-trimethylspiro[benzo[f][1,4]benzoxazine-3,2'-indole] Chemical compound C1=CC=CC2=C(N=CC3(C(C)(C)C4=CC=CC=C4N3C)O3)C3=CC=C21 CQTRKDFIQFOAQV-UHFFFAOYSA-N 0.000 description 1
- BVKXCOMITBBOBL-UHFFFAOYSA-N 1',3',3'-trimethylspiro[chromene-2,2'-indole]-6-carbonitrile Chemical compound O1C2=CC=C(C#N)C=C2C=CC21C(C)(C)C1=CC=CC=C1N2C BVKXCOMITBBOBL-UHFFFAOYSA-N 0.000 description 1
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- RBGUKBSLNOTVCD-UHFFFAOYSA-N methylanthraquinone Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 description 1
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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
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
-
- 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
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/136—Coating process making radiation sensitive element
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/163—Radiation-chromic compound
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/835,518 US7300727B2 (en) | 2004-04-29 | 2004-04-29 | Method for forming temporary image |
| US10/835,518 | 2004-04-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2504995A1 CA2504995A1 (en) | 2005-10-29 |
| CA2504995C true CA2504995C (en) | 2008-11-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002504995A Expired - Fee Related CA2504995C (en) | 2004-04-29 | 2005-04-22 | Method for forming temporary image |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7300727B2 (enExample) |
| EP (1) | EP1591829A1 (enExample) |
| JP (1) | JP2005316481A (enExample) |
| CN (1) | CN1702546A (enExample) |
| CA (1) | CA2504995C (enExample) |
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| US7300727B2 (en) * | 2004-04-29 | 2007-11-27 | Xerox Corporation | Method for forming temporary image |
| US7709164B2 (en) * | 2005-08-30 | 2010-05-04 | Xerox Corporation | Solvent-less process for producing transient documents |
| US7381506B2 (en) * | 2005-09-08 | 2008-06-03 | Xerox Corporation | Reimageable paper |
| AU2011253667B2 (en) * | 2005-12-14 | 2013-08-29 | Google Llc | Detecting and rejecting annoying media |
| US7971137B2 (en) * | 2005-12-14 | 2011-06-28 | Google Inc. | Detecting and rejecting annoying documents |
| US7488132B2 (en) * | 2005-12-21 | 2009-02-10 | Palo Alto Research Center Incorporated | Portable marking device for use with transient document media |
| US7875408B2 (en) * | 2007-01-25 | 2011-01-25 | International Business Machines Corporation | Bleachable materials for lithography |
| US7564030B2 (en) * | 2007-02-13 | 2009-07-21 | Palo Alto Research Center Incorporated | Method and system for forming temporary images |
| US7553603B2 (en) * | 2007-06-13 | 2009-06-30 | Xerox Corporation | Inkless printing paper and method |
| US7718325B2 (en) * | 2007-06-13 | 2010-05-18 | Xerox Corporation | Photochromic material, inkless reimageable printing paper, and methods |
| US7572569B2 (en) * | 2007-06-13 | 2009-08-11 | Xerox Corporation | Inkless printing paper and method |
| US7588878B2 (en) * | 2007-06-13 | 2009-09-15 | Xerox Corporation | Inkless printing paper and method |
| US7867672B2 (en) * | 2007-06-13 | 2011-01-11 | Xerox Corporation | Reimageable paper protected against UV light |
| US7645558B2 (en) * | 2007-06-13 | 2010-01-12 | Xerox Corporation | Inkless reimageable printing paper and method |
| US7852366B2 (en) * | 2007-06-13 | 2010-12-14 | Xerox Corporation | System and method for printing reimageable transient documents |
| US7655366B2 (en) | 2007-06-13 | 2010-02-02 | Xerox Corporation | Inkless reimageable printing paper and method |
| US7666558B2 (en) | 2007-06-13 | 2010-02-23 | Xerox Corporation | Inkless reimageable printing paper and method |
| US7572560B2 (en) * | 2007-06-13 | 2009-08-11 | Xerox Corporation | Inkless reimageable printing paper and method |
| US7541119B2 (en) | 2007-06-13 | 2009-06-02 | Xerox Corporation | Inkless reimageable printing paper and method |
| US7582398B2 (en) * | 2007-06-13 | 2009-09-01 | Xerox Corporation | Inkless reimageable printing paper and method |
| US7569316B2 (en) * | 2007-06-13 | 2009-08-04 | Xerox Corporation | Inkless reimageable printing paper and method |
| US7992959B2 (en) * | 2007-07-30 | 2011-08-09 | Lexmark International, Inc. | Printing system with transient and permanent imaging means |
| US20090080955A1 (en) * | 2007-09-26 | 2009-03-26 | Xerox Corporation | Content-changing document and method of producing same |
| US20090097898A1 (en) * | 2007-10-16 | 2009-04-16 | Xerox Corporation | Hand held photochromic marking implement |
| US7964271B2 (en) * | 2008-06-24 | 2011-06-21 | Xerox Corporation | Photochromic medium with erase-on-demand capability |
| US7678515B2 (en) * | 2008-08-12 | 2010-03-16 | Xerox Corporation | Thermally gated photochromic medium |
| US7645560B1 (en) | 2008-09-08 | 2010-01-12 | Xerox Corporation | Inkless reimageable printing paper and method |
| US7811741B2 (en) | 2009-02-24 | 2010-10-12 | Xerox Corporation | Reverse write erasable paper |
| US8344854B2 (en) * | 2009-02-26 | 2013-01-01 | Palo Alto Research Center Incorporated | Transient routing slips and inter-office envelopes |
| US8113646B2 (en) | 2009-03-09 | 2012-02-14 | Xerox Corporation | Combined inkjet and photochromic reusable paper personal printer |
| US7935463B2 (en) * | 2009-03-09 | 2011-05-03 | Xerox Corporation | Reusable paper media with compatibility markings and printer with incompatible media sensor |
| US8216765B2 (en) * | 2009-03-09 | 2012-07-10 | Xerox Corporation | Reimageable and reusable medium and method of producing and using the reimageable and reusable medium |
| US8441668B2 (en) * | 2009-04-08 | 2013-05-14 | Palo Alto Research Center Incorporated | Permanence estimation and policy enforcement for transient printing |
| US8670140B2 (en) * | 2009-04-08 | 2014-03-11 | Palo Alto Research Center Incorporated | Workflow management bridging virtual and transient-paper documents |
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2004
- 2004-04-29 US US10/835,518 patent/US7300727B2/en not_active Expired - Fee Related
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2005
- 2005-04-18 EP EP05103063A patent/EP1591829A1/en not_active Withdrawn
- 2005-04-22 CA CA002504995A patent/CA2504995C/en not_active Expired - Fee Related
- 2005-04-27 JP JP2005129033A patent/JP2005316481A/ja active Pending
- 2005-04-29 CN CNA2005100684026A patent/CN1702546A/zh active Pending
- 2005-08-30 US US11/215,950 patent/US7498122B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1591829A1 (en) | 2005-11-02 |
| CA2504995A1 (en) | 2005-10-29 |
| US7300727B2 (en) | 2007-11-27 |
| JP2005316481A (ja) | 2005-11-10 |
| US20050287475A1 (en) | 2005-12-29 |
| US20050244744A1 (en) | 2005-11-03 |
| CN1702546A (zh) | 2005-11-30 |
| US7498122B2 (en) | 2009-03-03 |
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