US3926825A - Liquid developer composition and process for preparing same - Google Patents
Liquid developer composition and process for preparing same Download PDFInfo
- Publication number
- US3926825A US3926825A US364848A US36484873A US3926825A US 3926825 A US3926825 A US 3926825A US 364848 A US364848 A US 364848A US 36484873 A US36484873 A US 36484873A US 3926825 A US3926825 A US 3926825A
- Authority
- US
- United States
- Prior art keywords
- weight
- liquid developer
- developer composition
- adjusting agent
- liquid
- 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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- 239000007788 liquid Substances 0.000 title claims abstract description 137
- 239000000203 mixture Substances 0.000 title claims abstract description 119
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000002245 particle Substances 0.000 claims abstract description 78
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 49
- -1 alkyl methacrylate-styrene-vinyltriethoxysilane Chemical compound 0.000 claims abstract description 33
- 239000000049 pigment Substances 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 30
- 229920001897 terpolymer Polymers 0.000 claims description 26
- 125000000962 organic group Chemical group 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 17
- 229920001296 polysiloxane Polymers 0.000 claims description 16
- 239000006185 dispersion Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 150000004819 silanols Chemical class 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
- 150000001282 organosilanes Chemical class 0.000 claims description 8
- 238000007259 addition reaction Methods 0.000 claims description 7
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 150000004756 silanes Chemical class 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical class CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 238000005054 agglomeration Methods 0.000 claims description 2
- 230000002776 aggregation Effects 0.000 claims description 2
- HMZBDKFOQYWSOV-UHFFFAOYSA-N ethenyl(triethoxy)silane;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCO[Si](OCC)(OCC)C=C HMZBDKFOQYWSOV-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000003384 imaging method Methods 0.000 abstract description 18
- 229920000642 polymer Polymers 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 description 26
- 239000003086 colorant Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000011161 development Methods 0.000 description 15
- 239000000178 monomer Substances 0.000 description 13
- 229910052710 silicon Inorganic materials 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 11
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 229920000180 alkyd Polymers 0.000 description 7
- 239000003350 kerosene Substances 0.000 description 7
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 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 5
- 238000012644 addition polymerization Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 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 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 239000000944 linseed oil Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 235000010187 litholrubine BK Nutrition 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 229940117958 vinyl acetate Drugs 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- ZXFHYTWKGJWGFM-UHFFFAOYSA-N 1-chloroethenyl acetate Chemical compound CC(=O)OC(Cl)=C ZXFHYTWKGJWGFM-UHFFFAOYSA-N 0.000 description 1
- DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical group CC(=C)CCC(C)=C DSAYAFZWRDYBQY-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
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
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- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
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- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
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- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
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- 229910001370 Se alloy Inorganic materials 0.000 description 1
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- PDAVOLCVHOKLEO-UHFFFAOYSA-N acetyl benzenecarboperoxoate Chemical compound CC(=O)OOC(=O)C1=CC=CC=C1 PDAVOLCVHOKLEO-UHFFFAOYSA-N 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- PGWFQHBXMJMAPN-UHFFFAOYSA-N ctk4b5078 Chemical compound [Cd].OS(=O)(=O)[Se]S(O)(=O)=O PGWFQHBXMJMAPN-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- MAYIDWCWWMOISO-UHFFFAOYSA-N dichloro-bis(ethenyl)silane Chemical compound C=C[Si](Cl)(Cl)C=C MAYIDWCWWMOISO-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- BRDYCNFHFWUBCZ-UHFFFAOYSA-N dodecaneperoxoic acid Chemical compound CCCCCCCCCCCC(=O)OO BRDYCNFHFWUBCZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical group 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000008096 xylene 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
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/12—Developers with toner particles in liquid developer mixtures
- G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
- G03G9/131—Developers with toner particles in liquid developer mixtures characterised by polymer components obtained by reactions only involving carbon-to-carbon unsaturated bonds
Definitions
- ABSTRACT Liquid developer compositions for use in developing a recording surface bearing an electrostatic latent image comprising finely divided colored marking particles substantially homogeneously dispersed in a carrier liquid, the colored marking particles comprising pigment particles substantially completely covered with a positive charge adjusting agent comprising a polymer of alkyl methacrylate-styrene-vinyltriethoxysilane. Imaging processes employing said liquid developer compositions are also disclosed.
- the formation and development of images on the surface of photoconductive materials by electrostatic means is well known.
- the basic electrostatographic process as taught by C. F. Carlson in US. Pat. No. 2,297,691, involves placing a uniform electrostatic charge on a photoconductive insulating layer, exposing the layer to a light and shadow image to dissipate the charge on the areas of the layer exposed to the light and developing the resulting electrostatic latent image by depositing on the image a finely divided electroscopic material referred to in the art as toner.
- the toner will normally be attracted to those areas of the layer which retain a charge, thereby forming a toner image corresponding to the electrostatic latent image.
- This powder image may then be transferred to a support surface such as paper.
- Electrophoretic development of an electrostatic latent image may also be achieved with liquid rather than dry developer materials.
- conventional liquid development more commonly referred to as electrophoretic development
- an insulating liquid vehicle having finely divided solid material dispersed therein contacts the imaging surface in both charged and uncharged areas. Under the influence of the electric field associated with the charged image pattern, the suspended particles migrate toward the charged portions of the imaging surface separating out of the insulating liquid. This electrophoretic migration of charged particles results in the deposition of the charged particles on the imaging surface in image con figuration.
- Electrophoretic development of an electrostatic latent image may, for example, be obtained by flowing the liquid developer over the image bearing surface. by immersing the imaging surface in a pool of the developer or by presenting the liquid developer on a smooth surface roller and moving the roller against the imaging surface.
- the charge adjusting agent is usually first added to the pigment and mixed sufficiently therewith'and the resulting mixture is dispersed in a carrier liquid.
- the charge adjusting agent is soluble in the carrier liquid, the mixture is rather easily dispersed.
- a liquid developer composition prepared as described above usually has poor storage properties, and the charges of the dispersed particles are apt to change with time. The result will be that the charge adjusting agent absorbed on the surface of the particles may be gradually released into the carrier'liquid. This defect may be eliminated by using a charge adjusting agent which is insoluble in the carrier liquid. That is, the charge adjusting agent will remain on thesurface of the pigment. thus the dispersed particles will retain a constant charge as against the carrier liquid since they are always combined with the charge adjusting agent.
- a charge adjusting agent As a method of preparing liquid developer compositions employing a charge adjusting agent, there is one wherein a mixture, for example, composed of a pigment and a charge adjusting agent, generally a resin, is kneaded in a carrier liquid and subsequently pulverized. In such a method, however, dispersed particles of a fine particle size are rarely produced since in the pulverizing process the pigment is exposed and apt to contact directly with the carrier liquid. There is also another method wherein particles of a small particle size in a mixture consisting of a pigment and a charge adjusting agent may be prepared by spray drying and then dispersed in a carrier liquid. However, when employing this method, it is difficult to make the particles themselves and it is also difficult to redisperse the primary particles in the carrier liquid since they tend to mass together and coagulate.
- liquid developer compositions of this invention may be prepared by the following steps:
- a mixture comprising a charge adjusting agent which is insoluble in the carrier liquid and a pigment is prepared using an appropriate solvent; (2) the resulting pasty mixture is dispersed in the carrier liquid by such means as high speed agitation and supersonic wave dispersion.
- the solvent to be used in Step 1 above is preferably one which is a good solvent for both the charge adjusting agent and a resin which is soluble in the carrier liquidz-The solvent should be miscible with the carrier liquid.
- the pigment In preparing the paste in Step (1), the pigment should be dispersed as finely as possible.
- the pigment- preferably exists merely in the state of a primary particle. Pigments prepared by a flushing process are, therefore, preferable.
- the solvent employed therein and a resin soluble in the carrier liquid dissolve into the carrier liquid to result in dividing the paste into fine particles, and simultaneously the pigment particles are individually coated with the charge adjusting agent. Since the solvent used for the preparation of the paste is ultimately mixed into the liquid developer composition, those solvent materials which deteriorate the electrical characteristics of the liquid developer are not preferable. Therefore, it is preferred that the solvent to be used in Step l possess a high electrical resistance.
- terpolymers of methylmethacrylatestyrenevinyltriethoxysilane and their analogs provide a charge adjusting agent which has excellent solubility in nonpolar solvents having high electrical resistances and which have good miscibility with a resin which is soluble in the carrier solvent to provide liquid developer compositions having stable positive charges.
- These terpolymers have been found to have good solubility in aromatic hydrocarbons, chlorinated hydrocarbons, and chloro-fluorinated hydrocarbons; and are insoluble in kerosene, cyclohexane, and isoparaffin which are commonly used as carrier liquids, and further provide strong positive charges in liquid developer compositions.
- any suitable carrier solvent may be used in the liquid developer compositions of the present invention.
- the carrier solvents to be used in the liquid developer compositions of this invention preferably have an electrical resistance greater than about 10" ohmscm and a dielectric constant less than about 3.5. It is preferred not to use an aromatic hydrocarbon alone, though such meets the above requirements, because such a solvent generally dissolves the charge adjusting agent, a terpolymer of alkylmethacrylate-styrene-vinyltriethoxysilane, from the surface-of the coated toner particles.
- Particularly preferred carrier solvents include linear aliphatic hydrocarbons such as kerosene, saturated alicyclic hydrocarbons such as cyclohexane, and branched aliphatic hydrocarbons such as isoparaffin. To reduce the flammability of such solutions, a small amount of chloro-fluorinated hydrocarbon may be added, unless it dissolves the charge adjusting agent.
- a small amount of a dispersion assistant may be added to the carrier solvent system.
- a dispersion assistant may be desirable to aid in redispersing the aforementioned paste.
- various vegetable oils and vegetable oil-modified alkyd resins may be employed.
- the amount of dispersion assistant to be added is generally in the range of from about 0.5 to about 30% by weight based on the carrier liquid. When adding a substantial amount of such a dispersion assistant, the viscosity of the carrier liquid generally increases to delay the speed of development.
- Typical dispersants providing the dual function of dispersing the solid colorant particles and suppress ing background include alkylated polyvinyl pyrrolidones and copolymers of alkyl vinyl ethers and maleic anhydride.
- Typical alkylated polyvinyl pyrrolidones include those wherein there is at least about one alkyl substitution for each monomer unit, the substitution generally being in the pyrrolidone moiety and wherein the alkyl substituent has a carbon chain length of from about to about carbon atoms.
- nonalkylated and alkylated polyvinyl pyrrolidones are also included.
- polymers containing both nonalkylated and alkylated polyvinyl pyrrolidones which may, for example, be prepared by copolymerizing mixtures of the alkylated and nonalkylated monomeric vinyl pyrrolidones.
- the nonalkylated vinyl pyrrolidone units may be present in amounts up to about 80% of the total number of vinyl pyrrolidone units.
- these alkylated polyvinyl pyrrolidones have molecular weights of from about 5,000 to about 300,000.
- the resin to be used as the charge adjusting agent is generally a terpolymer of alkylmethacrylate-styrene-vinyltriethoxy silane.
- alkyl group it has been found that a methyl, ethyl, or butyl group provides satisfactory results concerning solubility and dispersibility.
- the copolymerization ratio of methacrylatecstyrene may be optionally selected in the range of about 30:70 to about 90:10.
- the ratio of vinylalkoxy silane generally cannot be so high and is usually at most about 10% and preferably in the range of about 1 to 5%, all percentages being by weight.
- the ratio of polymerization usually has less influence and may be selected over a wider range.
- the solid terpolymer should comprise from about 5 to about 94.5% by weight of a styrene composition; from about 94.5 to about 5% by weight of an acrylate or methacrylate ester; and from about 0.5 to about 50% by weight of the polymerizable organo silicon composition because optimum properties are obtained.
- solid terpolymers comprising from about 0.5 to about 99% by weight of a styrene composition; from about 99 to about 0.5% by weight of an acrylate or methacrylate ester; and from about 0.5 to about 50% by weight of the polymerizable organo silicon composition.
- These reaction products have a weight average molecular weight of at least about 5,000.
- Optimum results are achieved with a terpolymer formed from the addition polymerization reaction between monomers or prepolymers of styrene, methylmethacrylate, and unsaturated organo silanes, silanols or siloxanes having from 1 to 3 hydrolyzable groups and an organic group attached directly to the silicon atom containing an unsaturated carbon-to-carbon linkage capable of addition polymerization.
- These reaction products have a weight average molecular weight of at least about 5,000.
- These polymers are preferred because they possess especially good triboelectric stability and excellent resistance to physical and chemical degradation. Good results are obtained with other addition reaction products of an unsaturated organo silicon compound and an unsaturated silicon-free compound.
- the unsaturated organic group attached to a silicon atom contains the unsaturation in a non-benzoid group and is preferably an unsaturated hydrocarbon group or derivatives thereof.
- Typical unsaturated organic groups include: vinyl, chlorovinyl, divinyl, styryl, distyryl, allyl, diallyl, triallyl, allylphenyl, dimethallyl, and methacryloxypropyl groups and derivatives thereof.
- Typical hydrolyzable groups include: ethoxy, methoxy, chloro, bromo, propyloxy. acetoxy, and amino groups.
- Suitable silicon-free monomers or prepolymers with which the above organo silicon compounds are particularly adapted to react to form the charge adjusting agents of this invention include the unsaturated compounds which normally form resinous polymers by addition type polymerization.
- Monomers or prepolymers containing the unsaturation in a non-benzoid group may be employed, such unsaturated monomers or prepolymers include those having an ethylenic or acetylenic linkage.
- olefins diolefins, acetylenes and their derivatives, particularly derivatives having substituents such as halogen, alkyl, aryl, unsaturated alicyclic and other types of substituent groups including, for example, nitrile or nitro groups.
- the unsaturated organic monomers containing the unsaturation in a non-benzoid group also include unsaturated hydrocarbons, aliphatic, carbocyclic, and heterocyclic compounds including unsaturated alcohols, aldehydes, ketones, quinones, acids, acid anhydrides, esters, nitriles, or nitro compounds.
- Typical unsaturated monomers include: ethylene, propylene, butenes, isobutylene, pentenes, hexenes, methyl methacrylate, methyl acrylate, vinyl chloride, vinylidene chloride, acrylonitrile, chlorovinyl acetate, styrene, butadiene, chloroprene, cyclopentadiene, divinylbenzene, cyclohexadiene, ethyl methacrylate, vinyl ace tate, vinyl toluene, acetylene, phenylacetylene, ethylvinyl benzene, allyl chloride, allyl benzene, maleic anhydride, ethyl acrylate, diethyl-maleate, butyl acrylate, butyl acrylate, butyl methacrylate, isobutyl methacrylate, methacrylic anhydride, vinyl formate, and mixtures thereof.
- alkyl peroxides such as tert-butyl hydroperoxide, and di-tertbutyl peroxide
- acyl and aroyl peroxides as as di-benzoyl peroxide, perbenzoic acid, dilauroyl peroxide, perlauric acid and acetyl benzoyl peroxide
- azo compounds such as azo-bis-isobutyro nitrile, dimethylazodiisobutyrate,
- the free-radical initiators or catalysts are employed in an amount from about 0.0001 to about 5.0% based on the combined weight of the polymerizable ingredients.
- the polymerization temperature to be employed is generally dependent on the batch size, the amount of catalyst present, the molecular weight to be attained, and the activation energy of the polymerization reaction.
- the rate of polymerization increases with an increase in temperature. Because greater exothermic reactions occur at high temperatures and increase the danger of uncontrollable reactions, high temperatures are preferably employed in processes where the heat of polymerization may be removed under controlled conditions'. e.g., in jacketed tubes through which the polymerizable or partially polymerized material is continuously passed and in stirred kettles.
- the polymerization temperature employed is usually within the range of about 60C to about the reflux temperatures of the monomer mixture at atmospheric pressure. However, economy and operating conditions such as the use of pressure or a vacuum may determine the use of higher or lower temperatures.
- Polymerization may be effectuated by suitable methods such as by bulk or solvent polymerization techniques.
- a solvent can be any suitable true organic solvent, i.e., a liquid unreactive to the system but capable of dissolving the reactive components.
- Typical well-known solvents in clude the chlorinated, ketone, ester, and hydrocarbon solvents such as, for example, xylene, benzene, toluene, hexane, cyclopentane, 1,1,l-trichloroethylene, ethyl acetate, methyl ethyl ketone, and the like.
- the amount of charge adjusting agent to be employed in the liquid developer compositions of this invention is generally that which is at least sufficient to form a continuous coating on the colored marking particles because the coating will then possess sufficient thickness to provide the desired positive charge adjusting properties to the developer composition.
- the colored marking particles may be premixed with any suitable resinous material.
- the premixed marking particles may be employed in the liquid developer in any suitable amount.
- the premixed colorant particles contain from about 20 wt. to about 50 wt. of the colorant particle and from about 50 wt. to about 80 wt. resin all by weight of the premixed colorant particle.
- Superior dispersion of the colorant particles in the liquid developer over an extended period of time is obtained when the proportion of resin is from about 55 wt. to about wt. by weight of the-premixed colorant particle and the amount of the premixed colorant present in the liquid developer is from about 25 to about 50% by weight of the liquid developer.
- resin component which is soluble in the carrier solvent
- resins as various vegetable oils, except castor oil, styrenated alkyd resins, vegetable oil modified alkyd resins, rosin modified alkyd resins, and rosin modified phenol form- 9 aldehyde resins.
- any suitable solid colorant material may be employed in the liquid developer compositions of this invention.
- the coloring materials that may be used in the invention; generally all the materials that are insoluble in the carrier solvent may be employed. Even though a coloring material which generally provides a negative charge in the carrier solvent when used as a pigment alone such as Phthalocyanine Green, it can obtain a positive charge by coating its surface with the positive charge adjusting agent of this invention. To obtain image permanence, it is preferred that the colorant be fast to light.
- the solid colorant may be of any suitable size. Typically, the colored marking particles are from about 0.01 to about 10 microns in size. For superior image resolution, it is preferred that the colored marking particles be from about 0.1 microns to about 1 micron.
- Typical solid colorants include solid finely divided colored materials such as pigments, xerographic toners, and other marking particles.
- Typical pigments include carbon black, charcoal and other forms of finely divided carbon, quinacridones, phthalocyanine blues, iron oxide, ultramarine blues, zinc oxide, titanium dioxide, and benzidine yellow.
- Typical xerographic toners include finely divided thermoplastic resins or blends of thermoplastic resins in which pigments such as carbon black are dispersed.
- liquid developer compositions of the instant invention may be employed to develop an electrostatic latent image present on any suitable electrostatographic imaging surface.
- any surface upon which an electrostatic charge pattern may be formed or developed may be employed.
- Typical electrostatic imaging surfaces include dielectrics such as plastic coated papers, zero printing masters, and photoconductors.
- Typical photoconductors that may be employed 'in include selenium and selenium alloys, cadmium sulfide, cadmium sulfoselenide, phthalocyanine binder coatings, polyvinylcarbazole sensitized with 2,4,7-trinitrofluorinone.
- the electrostatographic imaging surface may be employed in any suitable structure including plates, belts, or drums and may be employed in the form of a binder layer coated on a substrate.
- the imag ing surfaces may be overcoated with suitable dielectric materials in conventional manner.
- Development of electrostatic latent images may be obtained by positioning an applicator surface with liquid developer thereon adjacent to the electrostatographic imaging surface.
- Any suitable applicator surface may be employed.
- Typical applicator surfaces include, among others, porous ceramics, metallic sponge, patterned webs or belts, capillary combs, and cylindrical rolls having surface patterns such as single screw cuts or trihelecoid, pyramidal, or quadrugravure indentations.
- the applicator surface may be loaded with developer in any suitable manner.
- Typical developer loading techniques include applying developer from a roll or sponge roll or immersing the applicator in a bath. Prior to contacting the imaging surface, the applicator surface should be wiped or doctored clean to remove substantially all liquid developer from the applicator surface. Any suitable means may be provided such as a doctoring device. Typical doctoring devices include scraper blades and squeegee rolls. The doctoring in addition to removing liquid developer from raised portions of an applicator surface preferably provides a slight wiping action of the liquid developer in recessed 10 portions of the applicator surface to thereby maintain the level of the liquid developer in the recessed portions slightly below the level of the raised portions. Such a loading of developer on an applicator surface minimizes deposits in the non-image areas.
- a photosensitive layer was prepared from a composition comprising about 120 grams of photoconductive zinc oxide, about 36 grams of the copolymer of vinyl chloride and vinyl acetate, about 4 grams of ethylphtharyl glycolate, about 35 cc of toluene, and about 25 cc of butyl acetate.
- the composition was kneaded for about 20 hours in a ball mill.
- the viscosity of the composition was adjustedwith butyl acetate and the mixture was applied to paper treated by an electroconduc tive process employing a percolator so as to obtain a dry thickness of about 8 microns.
- the photoconductive layer was subjected to dark adaptation by allowing to stand in a dark place for about 20 hours at about 40C.
- the photosensitive layer prepared as described above was then exposed to corona discharge of about 7,000 volts to obtain a surface potential of about 450 volts.
- the charged photosensitive layer was then exposed to a light source having a color temperature of about 2,000 Kelvin for about 5 seconds through a positive original having a continuoustone image.
- the maximum illuminance on the surface of the photosensitive layer was about 5,500 lux.
- the photosensitive layer was treated in kerosene for prebath treatment and then put in the bath of the following liquid developer.
- composition was kneaded for about 40 hours in a ball mill:
- Microris Blue 4G-T Terpolymer of butylmethucrylatest ⁇ 'renevin vl triethoxy silane (copolymerization ratio 60130210) Styrenated alkyd resin Toluene 200 mg 500 mg cc Microris Blue 4G-T is a product of Chiba.
- the pigment is coated with a hydrogenated rosin ester by flushing.
- the hydrogenated rosin ester is soluble in the carrier liquid.
- the thus obtained blue paste was dispersed in the following solvent mixture:
- Phthalocyanine Green 2 grams Terpolymer of methylmethacrylate styrenevinyl triethoxy silane (copolymerization ratio 8():l5:5) 2 grams Soybean oil modified ulkyl resin (oil length 65%) 4 grams Toluene
- EXAMPLE IV present invention.
- steps or modifications may be used if desirable.
- other materials may be incorporated in the system of the present invention 12 which will enhance, synergize, or otherwise desirably affect the properties of the systems for their present use.
- a liquid developer composition for use in developing a recording surface bearing an electrostatic latent image said developer composition consisting essentially of finely divided colored marking particles substantially homogenously dispersed in a carrier liquid, said colored marking particles being substantially completely covered with a positive charge adjusting agent which is substantially insoluble in said carrier liquid, said charge adjusting agent consisting essentially of a solid terpolymer of l from about 5 to about 94.5% by weight of a polymerizable styrene composition, (2) from about 94.5 to about 5% by weight of a composition selected from the group consisting of polymerizable acrylate and methacrylate esters, and (3) from about 0.5 to about 50% by weight of a polymerizable organo silicone composition selected from the group consisting of vorgano silanes, silanols, and siloxanes having from 1 to 3 hydrolyzable groups and an organic group attached directly to a silicone atom containing an unsaturated carbon-to-carbon linkage, said terpolymer having a weight average mo
- a liquid developer composition for use in developing a recording surface bearing an electrostatic latent image said developer composition consisting essentially of finely divided colored marking particles substantially homogenously dispersed in a carrier liquid, said colored marking particles being substantially completely covered with a positive charge adjusting agent which is substantially insoluble in said carrier liquid, said charge adjusting agent consisting essentially of a solid polymeric addition reaction product of 1) from about 99.5 to about 50% by weight of a polymerizable styrene composition and a composition selected from the group consisting of polymerizable acrylate and methacrylate esters, and (2) from about 0.5 to about 50% by weight of a polymerizable organo silicone composition selected from the group consisting of silanes, silanols, and siloxanes having from 1 to 3 hydrolyzable groups and .an organic group attached directly to a silicone atom containing an unsaturated carbon-to-carbon linkage, said solid polymeric addition reaction product having aweight average molecular weight of at 13 least about 5,000.
- a liquid developer composition for use in developing a recording surface bearing an electrostatic latent image said developer composition consisting essentially of finely divided colored marking particles substantially homogenously dispersed in a carrier liquid, said colored marking particles being substantially completely covered with a positive charge adjusting agent which is substantially insoluble in said carrier liquid.
- said charge adjusting agent consisting essentially of a solid terpolymer of( 1 from about to about 94.5% by weight of a polymerizable styrene composition, (2) from about 94.5 to about 5% by weight of a polymerizable methacrylate composition selected from the group consisting of methyl, propyl, ethyl, and butyl methacrylates, and (3) from about 0.5 to about 50% by weight of a polymerizable organo silicone composition selected from the group consisting of silanes. silanols.
- siloxanes having from 1 to 3 hydrolyzable groups and an organic group attached directly to a silicone atom containing an unsaturated carbon-to-carbon linkage, said solid terpolymer having a weight-average molecular weight of at least about 5,000.
- a process for preparing a liquid developer composition according to claim 10 including admixing a resin which is soluble in said carrier liquid.
- a process for preparing a liquid developer composition according to claim 10 including admixing from about 0.5 to about 30% by weight based on the carrier liquid of a dispersion assistant to said liquid developer composition.
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Abstract
Liquid developer compositions for use in developing a recording surface bearing an electrostatic latent image comprising finely divided colored marking particles substantially homogeneously dispersed in a carrier liquid, the colored marking particles comprising pigment particles substantially completely covered with a positive charge adjusting agent comprising a polymer of alkyl methacrylate-styrene-vinyltriethoxysilane. Imaging processes employing said liquid developer compositions are also disclosed.
Description
United States Patent Honjo et al.
LIQUID DEVELOPER COMPOSITION AND PROCESS FOR PREPARING SAME Inventors: Satoru Honjo; Yasuo Tamai; Nobuo Tsuji, all of Tokyo, Japan Assignee: Xerox Corporation, Stamford,
Conn.
Filed: May 29, 1973 Appl. No.: 364,848
US. Cl 252/62.l; 427/17 Int. Cl. G036 9/12 Field of Search 252/621 L References Cited UNITED STATES PATENTS 4/1969 Wagner 252/62.l 6/1971 Machida et al. 252/62.l
3,668,127 6/1972 Machida et al. 252/621 3,729,419 4/1973 Honjo et al. 252/621 3,819,367 6/1974 Chatterji et 252/611 X Primary Examiner-Richard D. Levering 5 7] ABSTRACT Liquid developer compositions for use in developing a recording surface bearing an electrostatic latent image comprising finely divided colored marking particles substantially homogeneously dispersed in a carrier liquid, the colored marking particles comprising pigment particles substantially completely covered with a positive charge adjusting agent comprising a polymer of alkyl methacrylate-styrene-vinyltriethoxysilane. Imaging processes employing said liquid developer compositions are also disclosed.
12 Claims, No Drawings LIQUID DEVELOPER COMPOSITION AND PROCESS FOR PREPARING SAME BACKGROUND OF THE INVENTION This invention relates to imaging systems and more particularly to improved electrophotographic developer materials.
The formation and development of images on the surface of photoconductive materials by electrostatic means is well known. The basic electrostatographic process, as taught by C. F. Carlson in US. Pat. No. 2,297,691, involves placing a uniform electrostatic charge on a photoconductive insulating layer, exposing the layer to a light and shadow image to dissipate the charge on the areas of the layer exposed to the light and developing the resulting electrostatic latent image by depositing on the image a finely divided electroscopic material referred to in the art as toner. The toner will normally be attracted to those areas of the layer which retain a charge, thereby forming a toner image corresponding to the electrostatic latent image. This powder image may then be transferred to a support surface such as paper. The transferred image may be subsequently permanently affixed to a support surface as by heat. Instead of latent image formation by uniformly charging the photoconductive layer and then exposing the layer to a light and shadow image, one may form the latent image directly by charging the layer in image configuration. The powder image may be fixed to the photoconductive layer if elimination of the powder image transfer step is desired. Other suitable fixing means such as solvents or overcoating treatment may be substituted.
Similar methods are known for applying the electroscopic particles to the electrostatic latent image to be developed. Included within this group are the cascade" development techniques disclosed by E. N. Wise in US. Pat. No. 2,618,552; the powder cloud technique disclosed by C. F. Carlson in US, Pat. No. 2,221,776; and the magnetic brush process disclosed, for example, in US. Pat. No. 2,874,063.
Development of an electrostatic latent image may also be achieved with liquid rather than dry developer materials. In conventional liquid development, more commonly referred to as electrophoretic development, an insulating liquid vehicle having finely divided solid material dispersed therein contacts the imaging surface in both charged and uncharged areas. Under the influence of the electric field associated with the charged image pattern, the suspended particles migrate toward the charged portions of the imaging surface separating out of the insulating liquid. This electrophoretic migration of charged particles results in the deposition of the charged particles on the imaging surface in image con figuration. Electrophoretic development of an electrostatic latent image may, for example, be obtained by flowing the liquid developer over the image bearing surface. by immersing the imaging surface in a pool of the developer or by presenting the liquid developer on a smooth surface roller and moving the roller against the imaging surface.
Thus, in an electrophoretic development system, the entire imaging surface is contacted with the liquid developer with the charged particles separating from the carrier liquid and migrating to the charged field or image portions. The particles strongly adhere to the imaging surface by means of vanderWaals forces since the particles frequently come within about 500 angstroms of the imaging surface. Consequently, electrophoretic liquid development is particularly suitable for reproduction of continuoustone images to produce images of high quality. Further, electrophoretic development methods may provide excellent results when applying various liquid developers of different colors successively to an electrophotographic photosensitive layer comprised of, for example, photoconductive zinc oxide which is subsequently developed to produce a multi-colored image.
In general, liquid developer compositions are prepared by suspending finely divided particles having charges of the appropriate polarity and magnitude in a highly dielectric carrier solution. To obtain excellent electrophotographic characteristics, it is generally re quired that the magnitude of the charges on the suspended particles does not vary with respect to the carrier solution or that the polarity of the charges is not reversed even during a prolonged storage period. Therefore, when finely divided particles in a liquid developer composition have positive charges and the developer composition is applied to an electrostatic latent image bearing negative charges, positive development results, and when applying such a composition to a positively charged latent image, reversal development results.
When finely divided toner particles made of a composition which is insoluble in a carrier solution are dispersed in the carrier liquid, these particles generally have some potential against the carrier liquid. The polarity and the magnitude of charges are usually determined depending upon the conditions of the particle surface, the molecules absorbed onto the particle surface, and the like. When particles are dispersed in a solvent such as a hydrocarbon, their polarity is usually specific to themselves. For example, pigments such as Phthalocyanine Blue, Brilliant Carmine 6B, Hansa Yellow, natural and synthetic resins such as rosin, gelatin,
albumin, casein, cellulose acetate, polyvinyl acetate,
polyamides, nylon, and polymethylmethacrylate have positive charges. On the other hand, pigments such as sulphur, selenium, Phthalocyanine Green, lead chromate, nitrocellulose, copolymers of vinyl chloride, polyvinylidene chloride, polyvinylidene fluoride, chlorinated polypropylene, and phenolmodified alkyd resins provide negative charges on contact with solvents of hydrocarbon systems. It has been found experimentally that the polarities of these charges are almost coincidental with the materials in a triboelectric series.
It is preferable when preparing liquid developer compositions having positive polarities for development of negative electrostatic latent images borne on a zinc oxide photosensitive layer to employ pigments or resin materials which provide positive polarities as described above. For instance, when preparing a carmine developer, it is preferable to disperse Brilliant Carmine 6B into kerosene. However, in liquid developer compositions prepared by suspending and dispersing only a pigment, the charges of the particles are often unstable under storage conditions for a prolonged period. Moreover, when developing a multi-colored image with'developer compositions having different colors, it is very difficult to provide developer compositions prepared by suspending only pigments and to provide equal magnitudes of charges and to the suspended particles. Consequently, a charge adjusting agent is usually added to these compositions.
The charge adjusting agent is usually first added to the pigment and mixed sufficiently therewith'and the resulting mixture is dispersed in a carrier liquid. When the charge adjusting agent is soluble in the carrier liquid, the mixture is rather easily dispersed. However, a liquid developer composition prepared as described above usually has poor storage properties, and the charges of the dispersed particles are apt to change with time. The result will be that the charge adjusting agent absorbed on the surface of the particles may be gradually released into the carrier'liquid. This defect may be eliminated by using a charge adjusting agent which is insoluble in the carrier liquid. That is, the charge adjusting agent will remain on thesurface of the pigment. thus the dispersed particles will retain a constant charge as against the carrier liquid since they are always combined with the charge adjusting agent. When employing a charge adjusting agent which is insoluble in a carrier solvent, it is rather difficult, however. to prepare dispersed particles which are sufficiently finely divided.
As a charge adjusting agent which is insoluble in a carrier liquid and provides a positive polarity, ethylcellulose has been so employed. However, even though ethylcellulose provides somewhat stable positive charges in a carrier liquid, there are certain disadvantages in employing this material. That is, it is sparingly soluble in solvents such as aromatic or chlorinated hydrocarbons and even when it dissolves, it frequently results in high viscosities. Thus, the viscosity of a paste or mixture comprising such a charge adjusting agent and pigment particles is increased to result in difficulty in dispersing the paste into a carrier liquid.
As a method of preparing liquid developer compositions employing a charge adjusting agent, there is one wherein a mixture, for example, composed of a pigment and a charge adjusting agent, generally a resin, is kneaded in a carrier liquid and subsequently pulverized. In such a method, however, dispersed particles of a fine particle size are rarely produced since in the pulverizing process the pigment is exposed and apt to contact directly with the carrier liquid. There is also another method wherein particles of a small particle size in a mixture consisting of a pigment and a charge adjusting agent may be prepared by spray drying and then dispersed in a carrier liquid. However, when employing this method, it is difficult to make the particles themselves and it is also difficult to redisperse the primary particles in the carrier liquid since they tend to mass together and coagulate.
It is, therefore, clear that there is a continuing need for an improved liquid developer composition.
SUMMARY OF THE INVENTION It is, therefore, an object of this invention to provide liquid developer compositions which overcome the above noted deficiencies.
It is another object of this invention to provide novel liquid developer compositions containing a positive charge adjusting agent.
It is another object of this invention to provide liquid developer compositions which provide stable positive charges under prolonged storage conditions.
It is another object of this invention to provide liquid developer compositions which produce images having improved resolution and density.
It is another object of this invention to provide liquid developer compositions whichare superior to known liquid developer compositions.
The above objects and others are accomplished, gen erally speaking, by providing a liquid developer composition for electrophotography (wherein) finely divided toner particles are substantially completely covered with a positive charge adjusting agent which is insoluble in the carrier liquid and wherein the toner particles are homogenously dispersed in the carrier liquid.
Generally speaking, the liquid developer compositions of this invention may be prepared by the following steps:
l. a mixture comprising a charge adjusting agent which is insoluble in the carrier liquid and a pigment is prepared using an appropriate solvent; (2) the resulting pasty mixture is dispersed in the carrier liquid by such means as high speed agitation and supersonic wave dispersion.
The solvent to be used in Step 1 above is preferably one which is a good solvent for both the charge adjusting agent and a resin which is soluble in the carrier liquidz-The solvent should be miscible with the carrier liquid. In preparing the paste in Step (1), the pigment should be dispersed as finely as possible. For this purpose, the pigment-preferably exists merely in the state of a primary particle. Pigments prepared by a flushing process are, therefore, preferable. When adding the paste obtained in Step (1) to the carrier liquid, the solvent employed therein and a resin soluble in the carrier liquid dissolve into the carrier liquid to result in dividing the paste into fine particles, and simultaneously the pigment particles are individually coated with the charge adjusting agent. Since the solvent used for the preparation of the paste is ultimately mixed into the liquid developer composition, those solvent materials which deteriorate the electrical characteristics of the liquid developer are not preferable. Therefore, it is preferred that the solvent to be used in Step l possess a high electrical resistance.
In accordance with the present invention, it has been found that terpolymers of methylmethacrylatestyrenevinyltriethoxysilane and their analogs provide a charge adjusting agent which has excellent solubility in nonpolar solvents having high electrical resistances and which have good miscibility with a resin which is soluble in the carrier solvent to provide liquid developer compositions having stable positive charges. These terpolymers have been found to have good solubility in aromatic hydrocarbons, chlorinated hydrocarbons, and chloro-fluorinated hydrocarbons; and are insoluble in kerosene, cyclohexane, and isoparaffin which are commonly used as carrier liquids, and further provide strong positive charges in liquid developer compositions.
Any suitable carrier solvent may be used in the liquid developer compositions of the present invention. The carrier solvents to be used in the liquid developer compositions of this invention preferably have an electrical resistance greater than about 10" ohmscm and a dielectric constant less than about 3.5. It is preferred not to use an aromatic hydrocarbon alone, though such meets the above requirements, because such a solvent generally dissolves the charge adjusting agent, a terpolymer of alkylmethacrylate-styrene-vinyltriethoxysilane, from the surface-of the coated toner particles. Particularly preferred carrier solvents include linear aliphatic hydrocarbons such as kerosene, saturated alicyclic hydrocarbons such as cyclohexane, and branched aliphatic hydrocarbons such as isoparaffin. To reduce the flammability of such solutions, a small amount of chloro-fluorinated hydrocarbon may be added, unless it dissolves the charge adjusting agent.
A small amount of a dispersion assistant may be added to the carrier solvent system. Such a dispersion assistant may be desirable to aid in redispersing the aforementioned paste. As dispersion assistants, various vegetable oils and vegetable oil-modified alkyd resins may be employed. The amount of dispersion assistant to be added is generally in the range of from about 0.5 to about 30% by weight based on the carrier liquid. When adding a substantial amount of such a dispersion assistant, the viscosity of the carrier liquid generally increases to delay the speed of development.
The dispersants are incorporated to provide substantially uniform dispersion 'of the colorant material in the liquid developer. The dispersants further function to reduce colorant agglomerates and sedimentation and serve to maintain the colorant material in stable suspension without flocculation. A further function of the dispersant is to suppress the deposition of deposits in the background or nonimage areas of the imaging surface. The dispersant is generally miscible with the developer liquid in order to provide an integral developer wherein during development, there is no phase separation. The precise mechanism by which the dispersant inhibits the deposition of background deposits is not fully understood. It is clear, however, that in the ab sence of the presence of a dispersant, considerable background is usually present. Any suitable dispersant may be employed that is miscible with the developer vehicle. Typical dispersants providing the dual function of dispersing the solid colorant particles and suppress ing background include alkylated polyvinyl pyrrolidones and copolymers of alkyl vinyl ethers and maleic anhydride. Typical alkylated polyvinyl pyrrolidones include those wherein there is at least about one alkyl substitution for each monomer unit, the substitution generally being in the pyrrolidone moiety and wherein the alkyl substituent has a carbon chain length of from about to about carbon atoms. Also included are polymers containing both nonalkylated and alkylated polyvinyl pyrrolidones, which may, for example, be prepared by copolymerizing mixtures of the alkylated and nonalkylated monomeric vinyl pyrrolidones. In these polymers the nonalkylated vinyl pyrrolidone units may be present in amounts up to about 80% of the total number of vinyl pyrrolidone units. Generally, these alkylated polyvinyl pyrrolidones have molecular weights of from about 5,000 to about 300,000. Typical specific materials include decalated polyvinyl pyrrolidone, dodecalated polyvinyl pyrrolidone, tridecalated polyvinyl pyrrolidone, tetradecalated polyvinyl pyrrolidone, pentadecalated polyvinyl pyrrolidone, hexadecalated polyvinyl pyrrolidone and octodecylated polyvinyl pyrrolidone.
In accordance with this invention, the resin to be used as the charge adjusting agent is generally a terpolymer of alkylmethacrylate-styrene-vinyltriethoxy silane. As the alkyl group, it has been found that a methyl, ethyl, or butyl group provides satisfactory results concerning solubility and dispersibility. The copolymerization ratio of methacrylatecstyrene may be optionally selected in the range of about 30:70 to about 90:10. The ratio of vinylalkoxy silane generally cannot be so high and is usually at most about 10% and preferably in the range of about 1 to 5%, all percentages being by weight. The ratio of polymerization usually has less influence and may be selected over a wider range. In general, the charge adjusting agents of this invention are the products of an addition polymerization reaction between monomers or prepolymers of l) organo silanes, silanols, or siloxanes having from 1 to b 3 hydrolyzable groups and an organic group attached directly to the silicon atom containing an unsaturated carbon to carbon linkage capable of addition polymeri zation; and (2) one or more silicon free types of unsaturated polymerizable organic compounds. The resinous polymers of this invention have a weight average molecular weight of at least about 5,000. Optimum results have been obtained with polymers having a weight average molecular weight ranging from about 50,000 to about 1,250,000. Preferably, the organo silicon constituent of the polymer should be present in an amount at from about 0.5% to about 50% by weight for maximum properties. The polymers may comprise random, block or graft copolymers, terpolymers, and high mixed polymer systems.
Excellent results are obtained with a charge adjusting agent containing the solid polymeric reaction product of monomers or prepolymers of l) styrene; (2) acrylate or methacrylate esters; and (3) organo-silanes, silanols, or siloxanes having from 1 to 3 hydrolyzable groups and an organic group attached directly to the silicon atom containing an unsaturated carbon-to-carbon linkage capable of addition polymerization.
Preferably, the solid terpolymer should comprise from about 5 to about 94.5% by weight of a styrene composition; from about 94.5 to about 5% by weight of an acrylate or methacrylate ester; and from about 0.5 to about 50% by weight of the polymerizable organo silicon composition because optimum properties are obtained. However, satisfactory results are obtained with solid terpolymers comprising from about 0.5 to about 99% by weight of a styrene composition; from about 99 to about 0.5% by weight of an acrylate or methacrylate ester; and from about 0.5 to about 50% by weight of the polymerizable organo silicon composition. These reaction products have a weight average molecular weight of at least about 5,000. Optimum results are achieved with a terpolymer formed from the addition polymerization reaction between monomers or prepolymers of styrene, methylmethacrylate, and unsaturated organo silanes, silanols or siloxanes having from 1 to 3 hydrolyzable groups and an organic group attached directly to the silicon atom containing an unsaturated carbon-to-carbon linkage capable of addition polymerization. These reaction products have a weight average molecular weight of at least about 5,000. These polymers are preferred because they possess especially good triboelectric stability and excellent resistance to physical and chemical degradation. Good results are obtained with other addition reaction products of an unsaturated organo silicon compound and an unsaturated silicon-free compound.
The unsaturated organic group attached to a silicon atom contains the unsaturation in a non-benzoid group and is preferably an unsaturated hydrocarbon group or derivatives thereof. Typical unsaturated organic groups include: vinyl, chlorovinyl, divinyl, styryl, distyryl, allyl, diallyl, triallyl, allylphenyl, dimethallyl, and methacryloxypropyl groups and derivatives thereof. Typical hydrolyzable groups include: ethoxy, methoxy, chloro, bromo, propyloxy. acetoxy, and amino groups. Examples of typical unsaturated organo silanes having hydrolyzable groups attached to a silicon atom include: vinyltriethoxy silane, vinyltrimethoxy silane, vinyl-tris (betamethoxyethoxy) silane, gamma-methacryloxypropyltrimethoxy silane, vinyl trichlorosilane, vinyl triacetoxy silane, divinyl dichloro silane, and dimethylvinylchloro silane. Suitable corresponding polymerizable hydrolysis products and the corresponding siloxanes may be substituted for the foregoing unsaturated organo silanes. If more than one organic group is attached to a silicon atom, only one of the organic groups need be usaturated to enter into a polymerization reaction with other unsaturated monomers. Hence, compounds such as dimethyl vinyl cholorosilane are suitable. When more than one unsaturated group attached to the silicon atom is present, these unsaturated groups need not be identical. For example. vinyl allyl silicon chlorides and bromides may be employed. Partially condensed siloxanes in the liquid state having reactive unsaturated organic groups attached to a silicon atom may be employed as a component of the polymers of this invention.
Suitable silicon-free monomers or prepolymers with which the above organo silicon compounds are particularly adapted to react to form the charge adjusting agents of this invention include the unsaturated compounds which normally form resinous polymers by addition type polymerization. Monomers or prepolymers containing the unsaturation in a non-benzoid group may be employed, such unsaturated monomers or prepolymers include those having an ethylenic or acetylenic linkage. Thus, there are included olefins, diolefins, acetylenes and their derivatives, particularly derivatives having substituents such as halogen, alkyl, aryl, unsaturated alicyclic and other types of substituent groups including, for example, nitrile or nitro groups. The unsaturated organic monomers containing the unsaturation in a non-benzoid group also include unsaturated hydrocarbons, aliphatic, carbocyclic, and heterocyclic compounds including unsaturated alcohols, aldehydes, ketones, quinones, acids, acid anhydrides, esters, nitriles, or nitro compounds. Typical unsaturated monomers include: ethylene, propylene, butenes, isobutylene, pentenes, hexenes, methyl methacrylate, methyl acrylate, vinyl chloride, vinylidene chloride, acrylonitrile, chlorovinyl acetate, styrene, butadiene, chloroprene, cyclopentadiene, divinylbenzene, cyclohexadiene, ethyl methacrylate, vinyl ace tate, vinyl toluene, acetylene, phenylacetylene, ethylvinyl benzene, allyl chloride, allyl benzene, maleic anhydride, ethyl acrylate, diethyl-maleate, butyl acrylate, butyl acrylate, butyl methacrylate, isobutyl methacrylate, methacrylic anhydride, vinyl formate, and mixtures thereof.
The polymerizable unsaturated monomers or prepolymers with any free-radical initiator or catalyst capable of polymerizing the monomers or prepolymers. By a free-radical initiator or catalyst is meant a compound which is capable of producing free-radicals under the polymerization conditions employed, such as compounds having an -OOor an -N=Nlinkage. Examples of the more commonly employed freeradical initiators or catalysts include: alkyl peroxides, such as tert-butyl hydroperoxide, and di-tertbutyl peroxide; acyl and aroyl peroxides, as as di-benzoyl peroxide, perbenzoic acid, dilauroyl peroxide, perlauric acid and acetyl benzoyl peroxide, azo compounds, such as azo-bis-isobutyro nitrile, dimethylazodiisobutyrate,
LII
azo-bis-l-phenylethane and alkali metal azo-disulfonates; and the like. In general, the free-radical initiators or catalysts are employed in an amount from about 0.0001 to about 5.0% based on the combined weight of the polymerizable ingredients.
The polymerization temperature to be employed is generally dependent on the batch size, the amount of catalyst present, the molecular weight to be attained, and the activation energy of the polymerization reaction. The rate of polymerization increases with an increase in temperature. Because greater exothermic reactions occur at high temperatures and increase the danger of uncontrollable reactions, high temperatures are preferably employed in processes where the heat of polymerization may be removed under controlled conditions'. e.g., in jacketed tubes through which the polymerizable or partially polymerized material is continuously passed and in stirred kettles. The polymerization temperature employed is usually within the range of about 60C to about the reflux temperatures of the monomer mixture at atmospheric pressure. However, economy and operating conditions such as the use of pressure or a vacuum may determine the use of higher or lower temperatures. Polymerization may be effectuated by suitable methods such as by bulk or solvent polymerization techniques. If a solvent is employed, it can be any suitable true organic solvent, i.e., a liquid unreactive to the system but capable of dissolving the reactive components. Typical well-known solvents in clude the chlorinated, ketone, ester, and hydrocarbon solvents such as, for example, xylene, benzene, toluene, hexane, cyclopentane, 1,1,l-trichloroethylene, ethyl acetate, methyl ethyl ketone, and the like.
The amount of charge adjusting agent to be employed in the liquid developer compositions of this invention is generally that which is at least sufficient to form a continuous coating on the colored marking particles because the coating will then possess sufficient thickness to provide the desired positive charge adjusting properties to the developer composition.
Exceptional dispersion of the pigment particles in the liquid developer accompanied by substantially no background deposition is obtained when the colorant particles have been previously mixed with a resin. This premixing of the colorant particles enables the liquid developer to be rapidly formed and facilitates the maintenance of a substantially uniform dispersion of the colorant particles in the liquid vehicle without the formation of agglomerates. The colored marking particles may be premixed with any suitable resinous material. The premixed marking particles may be employed in the liquid developer in any suitable amount. Typically, the premixed colorant particles contain from about 20 wt. to about 50 wt. of the colorant particle and from about 50 wt. to about 80 wt. resin all by weight of the premixed colorant particle. Superior dispersion of the colorant particles in the liquid developer over an extended period of time is obtained when the proportion of resin is from about 55 wt. to about wt. by weight of the-premixed colorant particle and the amount of the premixed colorant present in the liquid developer is from about 25 to about 50% by weight of the liquid developer.
As the resin component, which is soluble in the carrier solvent, there may be employed such resins as various vegetable oils, except castor oil, styrenated alkyd resins, vegetable oil modified alkyd resins, rosin modified alkyd resins, and rosin modified phenol form- 9 aldehyde resins.
Any suitable solid colorant material may be employed in the liquid developer compositions of this invention. There is no particular limit as to the coloring materials that may be used in the invention; generally all the materials that are insoluble in the carrier solvent may be employed. Even though a coloring material which generally provides a negative charge in the carrier solvent when used as a pigment alone such as Phthalocyanine Green, it can obtain a positive charge by coating its surface with the positive charge adjusting agent of this invention. To obtain image permanence, it is preferred that the colorant be fast to light. The solid colorant may be of any suitable size. Typically, the colored marking particles are from about 0.01 to about 10 microns in size. For superior image resolution, it is preferred that the colored marking particles be from about 0.1 microns to about 1 micron. Typical solid colorants include solid finely divided colored materials such as pigments, xerographic toners, and other marking particles. Typical pigments include carbon black, charcoal and other forms of finely divided carbon, quinacridones, phthalocyanine blues, iron oxide, ultramarine blues, zinc oxide, titanium dioxide, and benzidine yellow. Typical xerographic toners include finely divided thermoplastic resins or blends of thermoplastic resins in which pigments such as carbon black are dispersed.
The liquid developer compositions of the instant invention may be employed to develop an electrostatic latent image present on any suitable electrostatographic imaging surface. Basically, any surface upon which an electrostatic charge pattern may be formed or developed may be employed. Typical electrostatic imaging surfaces include dielectrics such as plastic coated papers, zero printing masters, and photoconductors. Typical photoconductors that may be employed 'include selenium and selenium alloys, cadmium sulfide, cadmium sulfoselenide, phthalocyanine binder coatings, polyvinylcarbazole sensitized with 2,4,7-trinitrofluorinone. The electrostatographic imaging surface may be employed in any suitable structure including plates, belts, or drums and may be employed in the form of a binder layer coated on a substrate. The imag ing surfaces may be overcoated with suitable dielectric materials in conventional manner. Development of electrostatic latent images may be obtained by positioning an applicator surface with liquid developer thereon adjacent to the electrostatographic imaging surface. Any suitable applicator surface may be employed. Typical applicator surfaces include, among others, porous ceramics, metallic sponge, patterned webs or belts, capillary combs, and cylindrical rolls having surface patterns such as single screw cuts or trihelecoid, pyramidal, or quadrugravure indentations.
The applicator surface may be loaded with developer in any suitable manner. Typical developer loading techniques include applying developer from a roll or sponge roll or immersing the applicator in a bath. Prior to contacting the imaging surface, the applicator surface should be wiped or doctored clean to remove substantially all liquid developer from the applicator surface. Any suitable means may be provided such as a doctoring device. Typical doctoring devices include scraper blades and squeegee rolls. The doctoring in addition to removing liquid developer from raised portions of an applicator surface preferably provides a slight wiping action of the liquid developer in recessed 10 portions of the applicator surface to thereby maintain the level of the liquid developer in the recessed portions slightly below the level of the raised portions. Such a loading of developer on an applicator surface minimizes deposits in the non-image areas.
DESCRIPTION OF THE PREFERRED EMBODIMENTS The following preferred non-limiting examples further define, describe, and compare preferred materials and techniques of the present invention. In the examples, all parts and percentages are by weight unless otherwise specified.
EXAMPLE I A photosensitive layer was prepared from a composition comprising about 120 grams of photoconductive zinc oxide, about 36 grams of the copolymer of vinyl chloride and vinyl acetate, about 4 grams of ethylphtharyl glycolate, about 35 cc of toluene, and about 25 cc of butyl acetate. The composition was kneaded for about 20 hours in a ball mill. The viscosity of the composition was adjustedwith butyl acetate and the mixture was applied to paper treated by an electroconduc tive process employing a percolator so as to obtain a dry thickness of about 8 microns. After drying sufficiently, the photoconductive layer was subjected to dark adaptation by allowing to stand in a dark place for about 20 hours at about 40C. The photosensitive layer prepared as described above was then exposed to corona discharge of about 7,000 volts to obtain a surface potential of about 450 volts. The charged photosensitive layer was then exposed to a light source having a color temperature of about 2,000 Kelvin for about 5 seconds through a positive original having a continuoustone image. The maximum illuminance on the surface of the photosensitive layer was about 5,500 lux. After exposing, the photosensitive layer was treated in kerosene for prebath treatment and then put in the bath of the following liquid developer.
The following composition was kneaded for about 40 hours in a ball mill:
Carbon black 2 grams Terpolymer of methylmethacrylatestyrene-vinyl triethoxy silane (copolymerization ratio 5024515) 2 grams Styrenated alkyd resin 4 grams Toluene 50 cc One part of the resulting black paste was added to the following solventmixture with a supersonic dispersing apparatus:
Cyclohexane parts Kerosene 20 parts Linseed oil 5 parts After addition of the paste to the solvent mixture, the paste was dispersed for about 10 minutes with supersonic dispersion and the resulting black liquid developer was packed in a closed bottle for preservation.
The photosensitive layer prepared as described above EXAMPLE [I The following composition was mixed by high speed agitation.
Microris Blue 4G-T Terpolymer of butylmethucrylatest \'renevin vl triethoxy silane (copolymerization ratio 60130210) Styrenated alkyd resin Toluene 200 mg 500 mg cc Microris Blue 4G-T is a product of Chiba. The pigment is coated with a hydrogenated rosin ester by flushing. The hydrogenated rosin ester is soluble in the carrier liquid. The thus obtained blue paste was dispersed in the following solvent mixture:
Cyclohexane 75 parts Kerosene parts Linseed oil 5 parts The photosensitive layer of Example I green an electrostatic latent image was treated with the liquid developer composition described herein and a clear blue positive image was obtained.
EXAMPLE. m
The following composition was kneaded in a ball mill:
Phthalocyanine Green 2 grams Terpolymer of methylmethacrylate styrenevinyl triethoxy silane (copolymerization ratio 8():l5:5) 2 grams Soybean oil modified ulkyl resin (oil length 65%) 4 grams Toluene One part of the thus obtained green paste was dispersed in the following solvent mixture:
40 parts Cyclohexane Kerosene 55 parts Linseed oil 5 parts The photosensitive layer of Example I bearing an electrostatic latent image was treated with the thus obtained green liquid developer and a clear green positive image was obtained. It is to be noted that in the absence of the terpolymer, Phthalocyanine Green gave a negativecharge to produce a negative image.
EXAMPLE IV present invention. other steps or modifications may be used if desirable. In addition, other materials may be incorporated in the system of the present invention 12 which will enhance, synergize, or otherwise desirably affect the properties of the systems for their present use.
Anyone skilled in the art will have other modifications occur to him based on the teachings of the present invention. These modifications are intended to be encompassed within the scope of this invention.
What is claimed is:
l. A liquid developer composition for use in developing a recording surface bearing an electrostatic latent image, said developer composition consisting essentially of finely divided colored marking particles substantially homogenously dispersed in a carrier liquid, said colored marking particles being substantially completely covered with a positive charge adjusting agent which is substantially insoluble in said carrier liquid, said charge adjusting agent consisting essentially of a solid terpolymer of l from about 5 to about 94.5% by weight of a polymerizable styrene composition, (2) from about 94.5 to about 5% by weight of a composition selected from the group consisting of polymerizable acrylate and methacrylate esters, and (3) from about 0.5 to about 50% by weight of a polymerizable organo silicone composition selected from the group consisting of vorgano silanes, silanols, and siloxanes having from 1 to 3 hydrolyzable groups and an organic group attached directly to a silicone atom containing an unsaturated carbon-to-carbon linkage, said terpolymer having a weight average molecular weight of -at least about 5,000.
2. A liquid developer composition according to claim 1 wherein said terpolymer consists essentially of styrenealkyl methacrylate-vinyltriethoxysilane.
. 3.A liquid developer composition according to claim 1 wherein said colored marking particles have an average particle size from between about 0.01 to about 10 microns.
4. A liquid developer composition according to claim 1 wherein the amount of said charge adjusting agent is at least sufficient to form a continuous coating on said colored marking particles.
5. A liquid developercomposition according to claim 1 wherein said colored marking particles consist essentially of a pigment predispersed in a resin.
6. A liquid developer composition according to claim 1 wherein said liquid developer composition is substantially free of particle agglomeration.
7. A liquid developer composition for use in developing a recording surface bearing an electrostatic latent image, said developer composition consisting essentially of finely divided colored marking particles substantially homogenously dispersed in a carrier liquid, said colored marking particles being substantially completely covered with a positive charge adjusting agent which is substantially insoluble in said carrier liquid, said charge adjusting agent consisting essentially of a solid polymeric addition reaction product of 1) from about 99.5 to about 50% by weight of a polymerizable styrene composition and a composition selected from the group consisting of polymerizable acrylate and methacrylate esters, and (2) from about 0.5 to about 50% by weight of a polymerizable organo silicone composition selected from the group consisting of silanes, silanols, and siloxanes having from 1 to 3 hydrolyzable groups and .an organic group attached directly to a silicone atom containing an unsaturated carbon-to-carbon linkage, said solid polymeric addition reaction product having aweight average molecular weight of at 13 least about 5,000.
8. A liquid developer composition according to claim 7 wherein said polymeric addition reaction product is a copolymer.
9. A liquid developer composition for use in developing a recording surface bearing an electrostatic latent image, said developer composition consisting essentially of finely divided colored marking particles substantially homogenously dispersed in a carrier liquid, said colored marking particles being substantially completely covered with a positive charge adjusting agent which is substantially insoluble in said carrier liquid. said charge adjusting agent consisting essentially of a solid terpolymer of( 1 from about to about 94.5% by weight of a polymerizable styrene composition, (2) from about 94.5 to about 5% by weight of a polymerizable methacrylate composition selected from the group consisting of methyl, propyl, ethyl, and butyl methacrylates, and (3) from about 0.5 to about 50% by weight of a polymerizable organo silicone composition selected from the group consisting of silanes. silanols. and siloxanes having from 1 to 3 hydrolyzable groups and an organic group attached directly to a silicone atom containing an unsaturated carbon-to-carbon linkage, said solid terpolymer having a weight-average molecular weight of at least about 5,000.
10. A process for preparing a liquid developer composition for use in developing a recording surface bearing an electrostatic latent image, said process comprising the steps of mixing colored marking particles with a positive charge adjusting agent which is insoluble in a carrier liquid, the amount of said positive charge adjusting agent being sufficient to substantially completely cover said colored marking particles, and said charge adjusting agent consisting essentially of a solid terpolymer of (1) from about 5 to about 94.5% by weight, of a polymerizable styrene composition. (2) from about 94.5 to about 5% by weight of a composition selected from the group consisting of polymerizable acrylate and methacrylate esters, and (3) from about 0.5 to about 50% by weight of a polymerizable organo silicone composition selected from the group consisting of organo silanes. silanols, and siloxanes having from 1 to 3 hydrolyzable groups and an organic group attached directly to a silicone atom containing an unsaturated carbon-to-carbon linkage, said terpolymer having a weight average molecular weight of at least about 5,000, and dispersing said mixture in a carrier liquid having an electrical resistance greater than about 10" ohms-cm and a dielectric constant less than about 3.5.
11. A process for preparing a liquid developer composition according to claim 10 including admixing a resin which is soluble in said carrier liquid.
12. A process for preparing a liquid developer composition according to claim 10 including admixing from about 0.5 to about 30% by weight based on the carrier liquid of a dispersion assistant to said liquid developer composition.
Claims (12)
1. A PROCESS FOR PREPARING A LIQUID DEVELOPER COMPOSITION FOR USE IN DEVELOPING A RECORDING SURFACE BEARING AN ELECTROSTATIC LATENT IMAGE, SAID PROCESS COMPRISING THE STEPS OF MIXING COLORED MARKING PARTICLES WITH A POSITIVE CHARGE ADJUSTING AGENT WHICH IS INSOLUBLE IN A CARRIER LIQUID, THE AMOUNT OF SAID POSITIVE CHARGE ADJUSTING AGENT BEING SUFFICIENT TO SUBSTANTIALLY COMPLETELY COVER SAID COLORED MARKING PARTICLES, AND SAID CHARGE ADJUSTING AGENT CONSISTING ESSENTIALLY OF A SOLID TERPOLYMER OF (1) FROM ABOUT 5 TO ABOUT 94.5% BY WEIGHT, OF A POLYMERIZABLE STYRENE COMPOSITION, (2) FROM ABOUT 94.5 TO ABOUT 5% BY WEIGHT OF A COMPOSITION SELECTED FROM THE GROUP CONSISTSISTING OFF POLYMERIZABLE ACRYLATE AND METHACRYLATE ESTERS, AND (3) FROM ABOUT 0.5 TO ABOUT 50% BY WEIGHT OF A POLYMERIZABLE ORGANO SILICONE COMPOSITION SELECTED FROM THE GROUP CONSISTING OF ORGANO SILANES, SILANOLS, AND SILOXANES HAVING FROM 1 TO 3 HYDROLYZABLE GROUPS AND AN ORGANIC GROUP ATTACHED DIRECTLY TO A SILICONE ATOM CONTAINING AN UNSATURATED CARBON-TO-CARBON LINKAGE, SAID TERPOLYMER HAVING A WEIGHT AVERAGE MOLECULAR WEIGHT OF AT LEAST ABOUT 5,000, AND DISPERSING SAID MIXTURE IN A CARRIER LIQUID HAVING AN ELECTRICAL RESISTANCE GREATER THAN ABOUT 10**10 OHMS-CM AND A DIELECTRIC CONSTANT LESS THAN ABOUT 3.5.
1. A LIQUID DEVELOPER COMPOSITION FOR USE IN DEVELOPING A RECORDING SURFACE BEARING AN ELECTROSTATIC LATENT IMAGE, SAID DEVELOPER COMPOSITION CONSISTING ESSENTIALLY OF FINELY DIVIDED COLORED MARKING PARTICLES SUBSTANTIALLY HOMOGENEOUSLY DISPERSED IN A CARRIER LIQUID, SAID COLORED MARKING PARTICLES BEING SUBSTANTIALLY COMPLETELY COVERED WITH A POSITIVE CHARGE ADJUSTING AGENT WHICH IS SUBSTANTIALLY INSOLUBLE IN SAID CARRIER LIQUID, SAID CHARGE ADJUSTING AGENT CONSISTING ESSENTIALLY OF A SOLID TERPOLYMER OF (1) FROM ABOUT 5 TO ABOUT 94.5% BY WEIGHT OF A POLYMERIZABLE STYRENE COMPOSITION, (2) FROM ABOUT 94.5 TO ABOUT 5% BY WEIGHT OF A COMPOSITION SELECTED FROM THE GROUP CONSISTING OF POLYMERIZABLE ACRYLATE AND METHACRYLATE ESTERS, AND (3) FROM ABOUT 0.5 TO ABOUT 50% BY WEIGHT OF A POLYMERIZABLE ORGANO SILICONE COMPOSITION SELECTED FROM THE GROUP CONSISTING OF ORGANO SILANES, SILANOLS, AND SILOXANES HAVING FROM 1) TO 3 HYDROLYZABLE GROUPS AND AN ORGANIC GROUP ATTACHED DIRECTLY TO A SILICONE ATOM CONTAINING AN UNSATURATED CARBON-TO-CARBON LINKAGE, SAID TERPOLYMER HAVING A WEIGHT AVERAGE MOLECULAR WEIGHT OF AT LEAST ABOUT 5,000.
2. A liquid developer composition according to claim 1 wherein said terpolymer consists essentially of styrenealkyl methacrylate-vinyltriethoxysilane.
3. A liquid developer composition according to claim 1 wherein said colored marking particles have an average particle size from between about 0.01 to about 10 microns.
4. A liquid developer composition according to claim 1 wherein the amount of said charge adjusting agent is at least sufficient to form a continuous coating on said colored marking particles.
5. A liquid developer composition according to claim 1 wherein said colored marking particles consist essentially of a pigment predispersed in a resin.
6. A liquid developer composition according to claim 1 wherein said liquid developer composition is substantially free of particle agglomeration.
7. A liquid developer composition for use in developing a recording surface bearing an electrostatic latent image, said developer composition consisting essentially of finely divided colored marking particles substantially homogenously dispersed in a carrier liquid, said colored marking particles being substantially completely covered with a positive charge adjusting agent which is substantially insoluble in said carrier liquid, said charge adjusting agent consisting essentially of a solid polymeric addition reaction product of (1) from about 99.5 to about 50% by weight of a polymerizable styrene composition and a composition selected from the group consisting of polymerizable acrylate and methacrylate esters, and (2) from about 0.5 to about 50% by weight of a polymerizable organo silicone composition selected from the group consisting of silanes, silanols, and siloxanes having from 1 to 3 hydrolyzable groups and an organic group attached directly to a silicone atom containing an unsaturated carbon-to-carbon linkage, said solid polymeric addition reaction product having a weight average molecular weight of at least about 5,000.
8. A liquid developer composition according to claim 7 wherein said polymeric addition reaction product is a copolymer.
9. A liquid developer composition for use in developing a recording surface bearing an electrostatic latent image, said developer composition consisting essentially of finely divided colored marking particles substantially homogenously dispersed in a carrier liquid, said colored marking particles being substantially completely covered with a positive charge adjusting agent which is substantially insoluble in said carrier liquid, said charge adjusting agent consisting essentially of a solid terpolymer of (1) from about 5 to about 94.5% by weight of a polymerizable styrene composition, (2) from about 94.5 to about 5% by weight of a polymerizable methacrylate composition selected from the group consisting of methyl, propyl, ethyl, and butyl methacrylates, and (3) from about 0.5 to about 50% by weight of a polymerizable organo silicone composition selected from the group consisting of silanes, silanols, and siloxanes having from 1 to 3 hydrolyzable groups and an organic group attached directly to a silicone atom containing an unsaturated carbon-to-carbon linkage, said solid terpolymer having a weight-average molecular weight of at least about 5,000.
11. A process for preparing a liquid developer composition according to claim 10 including admixing a resin which is soluble in said carrier liquid.
12. A process for preparing a liquid developer composition according to claim 10 including admixing from about 0.5 to about 30% by weight based on the carrier liquid of a dispersion assistant to said liquid developer composition.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US364848A US3926825A (en) | 1973-05-29 | 1973-05-29 | Liquid developer composition and process for preparing same |
US05/579,339 US3976808A (en) | 1973-05-29 | 1975-05-21 | Imaging systems |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US364848A US3926825A (en) | 1973-05-29 | 1973-05-29 | Liquid developer composition and process for preparing same |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/579,339 Division US3976808A (en) | 1973-05-29 | 1975-05-21 | Imaging systems |
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US3926825A true US3926825A (en) | 1975-12-16 |
Family
ID=23436354
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US364848A Expired - Lifetime US3926825A (en) | 1973-05-29 | 1973-05-29 | Liquid developer composition and process for preparing same |
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US (1) | US3926825A (en) |
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US4070186A (en) * | 1974-08-26 | 1978-01-24 | Xerox Corporation | Tribo modified toner materials via silylation and electrostatographic imaging process |
US4525446A (en) * | 1983-01-20 | 1985-06-25 | Agfa-Gevaert, N.V. | Liquid developer for development of electrostatic images comprising onium salt polymer and an anion |
US4886729A (en) * | 1988-07-15 | 1989-12-12 | Xerox Corporation | Positively charged liquid developer compositions |
US20050069806A1 (en) * | 2003-09-30 | 2005-03-31 | Qian Julie Y. | Charge adjuvant delivery system and methods |
US20050153226A1 (en) * | 2003-12-17 | 2005-07-14 | Samsung Electronics Co., Ltd. | Liquid toner for electrophotography and method of preparing the same |
US20050244736A1 (en) * | 2004-04-29 | 2005-11-03 | Samsung Electronics Co., Ltd. | Liquid toner composition and preparation method of the same |
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US3438904A (en) * | 1966-01-10 | 1969-04-15 | Scm Corp | Liquid toner |
US3585140A (en) * | 1967-07-10 | 1971-06-15 | Ricoh Kk | Liquid developer for use in electrophotography containing a terpolymer |
US3668127A (en) * | 1968-07-01 | 1972-06-06 | Ricoh Kk | Liquid developer for electrophotography |
US3729419A (en) * | 1970-03-12 | 1973-04-24 | Xerox Corp | Liquid developer |
US3819367A (en) * | 1970-05-20 | 1974-06-25 | Xerox Corp | Imaging system |
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Publication number | Priority date | Publication date | Assignee | Title |
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US3438904A (en) * | 1966-01-10 | 1969-04-15 | Scm Corp | Liquid toner |
US3585140A (en) * | 1967-07-10 | 1971-06-15 | Ricoh Kk | Liquid developer for use in electrophotography containing a terpolymer |
US3668127A (en) * | 1968-07-01 | 1972-06-06 | Ricoh Kk | Liquid developer for electrophotography |
US3729419A (en) * | 1970-03-12 | 1973-04-24 | Xerox Corp | Liquid developer |
US3819367A (en) * | 1970-05-20 | 1974-06-25 | Xerox Corp | Imaging system |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4070186A (en) * | 1974-08-26 | 1978-01-24 | Xerox Corporation | Tribo modified toner materials via silylation and electrostatographic imaging process |
US4525446A (en) * | 1983-01-20 | 1985-06-25 | Agfa-Gevaert, N.V. | Liquid developer for development of electrostatic images comprising onium salt polymer and an anion |
US4886729A (en) * | 1988-07-15 | 1989-12-12 | Xerox Corporation | Positively charged liquid developer compositions |
US20050069806A1 (en) * | 2003-09-30 | 2005-03-31 | Qian Julie Y. | Charge adjuvant delivery system and methods |
EP1521131A2 (en) * | 2003-09-30 | 2005-04-06 | Samsung Electronics Co., Ltd. | Charge adjuvant delivery system and methods |
EP1521131A3 (en) * | 2003-09-30 | 2006-01-25 | Samsung Electronics Co., Ltd. | Charge adjuvant delivery system and methods |
US7118842B2 (en) | 2003-09-30 | 2006-10-10 | Samsung Electronics Company | Charge adjuvant delivery system and methods |
US20050153226A1 (en) * | 2003-12-17 | 2005-07-14 | Samsung Electronics Co., Ltd. | Liquid toner for electrophotography and method of preparing the same |
US7371496B2 (en) * | 2003-12-17 | 2008-05-13 | Samsung Electronics Co., Ltd. | Liquid toner for electrophotography and method of preparing the same |
US20050244736A1 (en) * | 2004-04-29 | 2005-11-03 | Samsung Electronics Co., Ltd. | Liquid toner composition and preparation method of the same |
US7374852B2 (en) * | 2004-04-29 | 2008-05-20 | Samsung Electronics Co., Ltd. | Liquid toner composition and preparation method of the same |
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