EP0324180A2 - Matériau d'enregistrement électrophotographique - Google Patents
Matériau d'enregistrement électrophotographique Download PDFInfo
- Publication number
- EP0324180A2 EP0324180A2 EP88121872A EP88121872A EP0324180A2 EP 0324180 A2 EP0324180 A2 EP 0324180A2 EP 88121872 A EP88121872 A EP 88121872A EP 88121872 A EP88121872 A EP 88121872A EP 0324180 A2 EP0324180 A2 EP 0324180A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- recording material
- polyvinylphenol
- photoconductive layer
- binder
- material according
- 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
- 239000000463 material Substances 0.000 title claims abstract description 25
- 229920001665 Poly-4-vinylphenol Polymers 0.000 claims abstract description 18
- 239000011230 binding agent Substances 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000000654 additive Substances 0.000 claims abstract description 5
- 239000005011 phenolic resin Substances 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims description 11
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims description 10
- 229920001568 phenolic resin Polymers 0.000 claims description 4
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 2
- 230000036211 photosensitivity Effects 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 231100000489 sensitizer Toxicity 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical group OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- -1 Hydroxy, amino Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZPANWZBSGMDWON-UHFFFAOYSA-N 1-[(2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 ZPANWZBSGMDWON-UHFFFAOYSA-N 0.000 description 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- TZXATTMVGZDPHM-UHFFFAOYSA-N 2-[4-[(2-chloro-4-nitrophenyl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium Chemical compound C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl TZXATTMVGZDPHM-UHFFFAOYSA-N 0.000 description 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- ZRUOTKQBVMWMDK-UHFFFAOYSA-N 2-hydroxy-6-methylbenzaldehyde Chemical compound CC1=CC=CC(O)=C1C=O ZRUOTKQBVMWMDK-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 1
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical compound [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 1
- MPVDXIMFBOLMNW-ISLYRVAYSA-N 7-hydroxy-8-[(E)-phenyldiazenyl]naphthalene-1,3-disulfonic acid Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1\N=N\C1=CC=CC=C1 MPVDXIMFBOLMNW-ISLYRVAYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DOLKKDJAWDNAMU-UHFFFAOYSA-N [4-[bis[4-(diethylamino)phenyl]methylidene]naphthalen-1-ylidene]-(4-methylphenyl)azanium;chloride Chemical compound [Cl-].C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=C(C)C=C1 DOLKKDJAWDNAMU-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000002048 anodisation reaction Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical group C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical group 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0532—Macromolecular bonding materials obtained by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0535—Polyolefins; Polystyrenes; Waxes
Definitions
- the invention relates to an electrophotographic recording material comprising an electrically conductive layer support, particularly suitable for the production of printing forms or printed circuits, and a photoconductive layer which contains organic photoconductor, phenolic resin as a binder, sensitizer and conventional additives.
- Recording material of the type described is known (DE-PS 25 26 720 corresponding to US-PS 4,063,948). It contains binders in the photoconductive layer which are soluble in aqueous or alkaline solvent systems. These include high-molecular substances which carry alkali-solubilizing groups such as acid, anhydride, carboxyl, phenol, sulfonic acid, sulfonamide or sulfonimide groups. Binders with high acid numbers are particularly suitable. With good electrophotographic properties, however, the solubility of the layer is not yet adjusted to meet the highest requirements for reproducing small details.
- mixtures which contain photosensitive compounds such as o-quinonediazides and phenol condensation products such as novolak. After UV exposure, they experience a change in their solubility in an aqueous alkaline solution through the decomposition reaction of the photosensitive compounds.
- photosensitive compounds such as o-quinonediazides and phenol condensation products such as novolak.
- novolak component polymers or copolymers can be used which have vinylphenol units (DE-PS 23 22 230 corresponding to US-PS 3,869,292). Their use for electrophotographic purposes could not be deduced from this.
- the solution to this problem is based on a material of the type mentioned at the outset, and it is characterized in that an optionally substituted polyvinylphenol is present in the photoconductive layer as a binder.
- an optionally substituted polyvinylphenol is present in the photoconductive layer as a binder.
- a polyvinylphenol with a molecular weight between 1500 and 60,000 is present.
- the polyvinylphenol according to the invention is preferably a polymer of p-vinylphenol.
- the polyvinylphenol can preferably be halogen-substituted.
- chlorinated or brominated, in particular brominated, polymers are preferably used as halogenated vinylphenol polymers.
- copolymers of vinylphenols and other vinyl compounds such as styrene or acrylic acid esters can also be used.
- the homopolymers of p-vinylphenol are preferred.
- the halogen content of the halogenated polyvinylphenol is generally between 20 and 60, preferably 40-60 percent by weight.
- an o-quinonediazide is preferred in the photoconductive layer according to the invention an o-naphthoquinonediazide is present. It is hereby achieved that the photoconductive layer can be subjected to a post-exposure with UV light after the development (emphasis), which results in a particularly good solubility of the exposed areas during the stripping. The applied toner image can not be fixed. It was completely surprising that the addition of the light-sensitive substance does not adversely change the electrophotographic properties of the photoconductive layer and exhibits good charging behavior with little dark discharge. The recording material also has a good shelf life.
- the photoconductive layer can generally contain 5-40 percent by weight of o-quinonediazide. Preferably 15 to 25 percent by weight is present.
- the reproduction of fine picture elements, such as fine raster, is made possible in excellent quality.
- cellulose products such as special papers, cellulose hydrate, cellulose acetate
- plastics such as polyamides in film form or metal-coated films, are also suitable as layer supports.
- the surface refinement consists in mechanical or electrochemical roughening and, if appropriate, in a subsequent anodization and treatment with polyvinylphosphonic acid according to DE-OS 16 21 478 in accordance with US Pat. No. 4,153,461. This results in a higher print run and less susceptibility to oxidation.
- the organic photoconductors used for the photoconductive layer can be regarded as known in principle. The following are possible:
- Triphenylamine derivatives more highly condensed aromatic compounds, such as anthracene, benzo-fused heterocycles, such as benzothiazoles, pyrazoline, imidazole or triazole derivatives, oxdiazole derivatives such as 2,5-bis- (4'-diethylaminophenyl) oxdiazole-1,3,4), oxazole derivatives such as 2 -Phenyl-4- (2'-chlorophenyl) -5- (4 ⁇ -diethylaminophenyl) oxazole, further vinyl aromatic polymers such as polyvinylanthracene, polyacenaphthylene or polyvinyl carbazole and their copolymers, provided that they are compatible with polyvinylphenol and are suitable for differentiation in solubility.
- aromatic polymers such as polyvinylanthracene, polyacenaphthylene or polyvinyl carbazole and their copolymers, provided that they are compatible
- Preferred o-quinonediazides to be added are preferably o-naphthoquinonediazides, such as the di- or tri-esters of 2,3,4-trihydroxybenzophenone and naphthoquinone- (1,2) -diazide- (2) -5-or 4-sulfonic acid, esters , especially the diester of bis (2-hydroxynaphthyl) methane and naphthoquinone (1,2) diazide- (2) -5-sulfonic acid and esters from 2-phenyl-2- (4'-hydroxyphenyl) propane and naphthoquinone (1,2) diazide- (2) -4- sulfonic acid.
- Esters from hydroxyl-containing polymers and naphthoquinonediazide sulfonic acids are also suitable. Mixtures of the quinonediazide sulfonic acid esters mentioned can also be used with good success.
- Additional binders can also be contained in the photoconductive layer. Their addition serves to improve the film properties of the layer, its adhesive strength on the substrate and to increase the print run.
- Suitable binders are, for example, copolymers of styrene and maleic anhydride and their partial esterification products, polyvinyl acetates and copolymers with crotonic acid, phenolic resins, coumarone-indene resins, polyacrylates and copolymers with acrylic acid, rosin and its conversion products, maleate resins and phthalate resins.
- Electrophotographic recording material contains at least one sensitizing dye to expand the spectral sensitivity range.
- Suitable sensitizing dyes are, for example, malachite green (Color Index (CI) 42 000), crystal violet (CI 42 555), methyl violet (CI No. 42 535), night blue (CI No. 44 085), Victoria blue (CI No. 44 045 or No. 52595: 2), Rhodamine B, Rhodamine FB (CI No. 45 170), Capri Blue (CI No. 51 015), Methy len blue (CI No. 52 015), fuchsin (CI No. 42 500), Rose Bengal (CI No. 45 440), polymethine dyes such as astrazone orange G (CI No.
- the recording material according to the invention can contain leveling agents and plasticizers as conventional additives in the photoconductive layer and / or adhesion promoter between layer support and layer.
- the presence of the additive does not significantly affect the interaction between the photoconductor and any o-quinonediazide present.
- the solution is thus applied to a 300 ⁇ m thick, electrochemically roughened, anodized aluminum plate pretreated with polyvinylphosphonic acid wear that a photoconductor layer with a thickness of 5.5 microns is formed after the solvent has evaporated.
- the light sensitivity of the layer is determined by charging it to -500 V and exposing it to white incandescent light until it is discharged to a residual voltage of -60 V.
- the energy density required for this is 320 ⁇ J / cm2.
- the photoconductor layer is charged with a corona to a surface potential of -500 V and exposed to images in a repro camera with 8 halogen lamps of 500 watts for 20 seconds.
- the resulting latent charge image is developed using a magnetic roller with a commercially available toner / carrier development mixture.
- the developed image is fixed with the help of thermal radiation.
- the plate For conversion into a printing form, the plate is immersed for 2 minutes in a solution which is obtained by dissolving 20 g Na2SiO3 ⁇ 9H2O and 2 g NaOH in a mixture of 728 g water, 100 g n-propanol and 150 g ethylene diglycol.
- the layer parts not covered by the toner image are removed with a water jet with gentle rubbing.
- the printing form obtained is characterized by good raster and full tone reproduction.
- the plate prints well over 100,000 prints in a sheetfed offset press.
- the 50 g poly-p-vinylphenol resin is replaced by a novolak made from m-cresol and Formaldehyde (Alnovol® 429 K from HOECHST AG) gives a printing plate which requires an energy density of 520 ⁇ J / cm2 to discharge from -500 V to -60V and which has to be exposed in the repro camera for 30 seconds.
- the residence time in the stripping solution described above is 6 minutes.
- 35 g of 2-vinyl-4- (2'-chlorophenyl) -5- (4 ⁇ -diethylaminophenyl) oxazole and 40 g of polyvinylphenol are dissolved in a mixture of 160 ml of ethylene glycol monomethyl ether, 270 ml of tetrahydrofuran and 60 ml of butyl acetate and the solution is added 440 mg astrazone orange R (CI 48 040) and 350 mg astrazone red violet 3 RN (CI 48 013).
- the solution is used to coat an anodized aluminum plate which has been roughened by wet brushing and pretreated with polyvinylphosphonic acid in such a way that the photoconductor layer has a weight per unit area of 5.5 g / m 2.
- the plate is charged (-500 V) and exposed as described in Example 1, the exposure time being only 14 seconds in order to achieve a high-contrast, base-free image.
- the latent electrostatic image has been made visible with a dry developer and the toner image has been fixed by means of heat radiation
- the plate is passed through a commercially available stripping device to remove the non-image areas at a throughput speed of 1.1 m / min.
- the plate is charged to -500 V and imagewise exposed in a repro camera for 18 seconds with 10 halogen lamps of 600 watts, developed and fixed in a known manner.
- the photoconductor layer is removed at the areas not covered by toner with the solution described in Example 1.
- the printing result achieved with the plate is excellent.
- a 300 ⁇ m thick, electrochemically roughened, anodized and treated with polyvinylphosphonic acid-treated aluminum foil is coated with the solution in such a way that a 5 ⁇ m thick photoconductor layer remains after the solvents have evaporated.
- the layer is charged to -500 V and exposed in a repro camera as described in Example 1.
- the toner image created after development is not fixed.
- the concrete plate is exposed for 2 minutes in a commercially available automatic copying machine under a 5 KW metal halogen lamp (Violight).
- the toner image is then removed by rinsing with water and the plate is immersed in a stripping solution described in Example 1 for 1/2 minute, rinsed with water and rubbed off.
- a printing form is obtained in which, in particular, a rastered image is better reproduced than with the plates described in Examples 1-3.
- An anodized aluminum foil is coated with the solution as described in Example 4.
- a toner image that is not fixed is produced on the coated film by electrophotography.
- the toner image is rinsed off with water.
- the plate is immersed in a decoater solution described in Example 1 for 30 seconds and rinsed with water while rubbing. You get a planographic printing form with very good image reproduction and high print run quality.
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3800617A DE3800617A1 (de) | 1988-01-12 | 1988-01-12 | Elektrophotographisches aufzeichnungsmaterial |
DE3800617 | 1988-01-12 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0324180A2 true EP0324180A2 (fr) | 1989-07-19 |
EP0324180A3 EP0324180A3 (en) | 1990-01-17 |
EP0324180B1 EP0324180B1 (fr) | 1993-07-21 |
Family
ID=6345116
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88121872A Expired - Lifetime EP0324180B1 (fr) | 1988-01-12 | 1988-12-30 | Matériau d'enregistrement électrophotographique |
Country Status (4)
Country | Link |
---|---|
US (1) | US4933248A (fr) |
EP (1) | EP0324180B1 (fr) |
JP (1) | JPH01216362A (fr) |
DE (2) | DE3800617A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0470729A1 (fr) * | 1990-07-26 | 1992-02-12 | Matsushita Electric Industrial Co., Ltd. | Matériau photosensible pour l'électrophotographie et procédé pour le préparer |
EP0720060A1 (fr) | 1994-12-21 | 1996-07-03 | Hoechst Aktiengesellschaft | Procédé pour développer des matériaux d'enregistrement sensibles aux rayonnements exposés |
US6190825B1 (en) | 1998-01-30 | 2001-02-20 | Agfa-Gevaert N.V. | Polymers containing N-substituted maleimide units and their use in radiation-sensitive mixtures |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5437952A (en) * | 1992-03-06 | 1995-08-01 | Konica Corporation | Lithographic photosensitive printing plate comprising a photoconductor and a naphtho-quinone diazide sulfonic acid ester of a phenol resin |
JPH05323682A (ja) * | 1992-05-18 | 1993-12-07 | Konica Corp | 印刷版の製版方法 |
TW425637B (en) * | 1993-01-18 | 2001-03-11 | Semiconductor Energy Lab | Method of fabricating mis semiconductor device |
US6214502B1 (en) | 1998-07-21 | 2001-04-10 | Lexmark International, Inc. | Charge generation layers comprising binder blends and photoconductors including the same |
US6376144B1 (en) | 2000-08-03 | 2002-04-23 | Kodak Polychrome Graphics, Llc | Organic photoconductive composition |
US20040043314A1 (en) * | 2002-08-30 | 2004-03-04 | Nusrallah Jubran | Organophotoreceptors with a fluoran-based compound |
KR100916656B1 (ko) | 2002-10-22 | 2009-09-08 | 삼성전자주식회사 | 레이저 조사 장치 및 이를 이용한 다결정 규소 박막트랜지스터의 제조 방법 |
JP4506583B2 (ja) * | 2005-06-24 | 2010-07-21 | 富士ゼロックス株式会社 | コーティング剤組成物、電子写真感光体及びその製造方法、画像形成装置 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1447008A1 (de) * | 1962-09-22 | 1969-01-23 | Kalle Ag | Verfahren zur elektrophotographischen Herstellung von Druckformen |
FR2183748A1 (fr) * | 1972-05-05 | 1973-12-21 | Oce Van Der Grinten Nv | |
EP0125481A1 (fr) * | 1983-04-15 | 1984-11-21 | Hoechst Aktiengesellschaft | Matériau d'enregistrement électrophotographique |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE625567A (fr) * | 1961-12-04 | |||
ZA6807938B (fr) * | 1967-12-04 | |||
JPS51105389A (en) * | 1975-03-01 | 1976-09-17 | Kenji Kanezaki | Kojundo pp binirufuenoorujugotaino seizohoho |
AU507694B2 (en) * | 1975-06-14 | 1980-02-21 | Hoechst Aktiengesellschaft | Electrophotographic reproduction |
GB2014748B (en) * | 1978-02-07 | 1982-06-16 | Konishiroku Photo Ind | Electrophotographic material for obtaining toner image and process for forming printing plate by using the same |
JPS5730829A (en) * | 1980-08-01 | 1982-02-19 | Hitachi Ltd | Micropattern formation method |
US4439516A (en) * | 1982-03-15 | 1984-03-27 | Shipley Company Inc. | High temperature positive diazo photoresist processing using polyvinyl phenol |
-
1988
- 1988-01-12 DE DE3800617A patent/DE3800617A1/de not_active Withdrawn
- 1988-12-30 DE DE8888121872T patent/DE3882509D1/de not_active Expired - Fee Related
- 1988-12-30 EP EP88121872A patent/EP0324180B1/fr not_active Expired - Lifetime
-
1989
- 1989-01-11 US US07/295,759 patent/US4933248A/en not_active Expired - Fee Related
- 1989-01-12 JP JP1003883A patent/JPH01216362A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1447008A1 (de) * | 1962-09-22 | 1969-01-23 | Kalle Ag | Verfahren zur elektrophotographischen Herstellung von Druckformen |
FR2183748A1 (fr) * | 1972-05-05 | 1973-12-21 | Oce Van Der Grinten Nv | |
EP0125481A1 (fr) * | 1983-04-15 | 1984-11-21 | Hoechst Aktiengesellschaft | Matériau d'enregistrement électrophotographique |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0470729A1 (fr) * | 1990-07-26 | 1992-02-12 | Matsushita Electric Industrial Co., Ltd. | Matériau photosensible pour l'électrophotographie et procédé pour le préparer |
EP0720060A1 (fr) | 1994-12-21 | 1996-07-03 | Hoechst Aktiengesellschaft | Procédé pour développer des matériaux d'enregistrement sensibles aux rayonnements exposés |
US6190825B1 (en) | 1998-01-30 | 2001-02-20 | Agfa-Gevaert N.V. | Polymers containing N-substituted maleimide units and their use in radiation-sensitive mixtures |
Also Published As
Publication number | Publication date |
---|---|
EP0324180A3 (en) | 1990-01-17 |
DE3882509D1 (de) | 1993-08-26 |
EP0324180B1 (fr) | 1993-07-21 |
JPH01216362A (ja) | 1989-08-30 |
US4933248A (en) | 1990-06-12 |
DE3800617A1 (de) | 1989-07-20 |
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