CA1156084A - Toner magnetique comprenant une resine qui est le produit d'esterification polymerique d'un acide dicarboxylique et d'un diphenol - Google Patents

Toner magnetique comprenant une resine qui est le produit d'esterification polymerique d'un acide dicarboxylique et d'un diphenol

Info

Publication number: CA1156084A
Authority: CA; Canada
Prior art keywords: toner; magnetic; bis; carbon atoms; phenyl
Prior art date: 1980-01-28
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

Application number

CA000369282A

Other languages

English (en)

Inventor

Stephen L. Gaudioso

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Xerox Corp

Original Assignee

Xerox Corp

Priority date (The priority date 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 date listed.)

1980-01-28

Filing date

1981-01-26

Publication date

1983-11-01

1980-01-28 Priority claimed from US06/115,973 external-priority patent/US4271248A/en

1980-06-03 Priority claimed from US06/155,974 external-priority patent/US4336556A/en

1981-01-26 Application filed by Xerox Corp filed Critical Xerox Corp

1983-11-01 Application granted granted Critical

1983-11-01 Publication of CA1156084A publication Critical patent/CA1156084A/fr

Status Expired legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title claims abstract description 27
239000011347 resin Substances 0.000 title claims abstract description 27
XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 title claims abstract description 12
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims abstract description 12
230000032050 esterification Effects 0.000 title claims abstract description 8
238000005886 esterification reaction Methods 0.000 title claims abstract description 8
239000000463 material Substances 0.000 title description 19
150000002009 diols Chemical class 0.000 claims abstract description 9
239000000696 magnetic material Substances 0.000 claims abstract description 8
238000000034 method Methods 0.000 claims description 27
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
238000003384 imaging method Methods 0.000 claims description 21
239000002245 particle Substances 0.000 claims description 19
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 16
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 11
239000001294 propane Substances 0.000 claims description 11
239000000758 substrate Substances 0.000 claims description 11
239000001530 fumaric acid Substances 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
239000003086 colorant Substances 0.000 claims description 8
239000000047 product Substances 0.000 claims description 8
SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
239000007859 condensation product Substances 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
229910045601 alloy Inorganic materials 0.000 claims description 3
239000000956 alloy Substances 0.000 claims description 3
150000002739 metals Chemical class 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
SXONZCYCWKRIEM-UHFFFAOYSA-N 4-[2-(4-hydroxy-2-propan-2-yloxyphenyl)propan-2-yl]-3-propan-2-yloxyphenol Chemical compound CC(C)OC1=CC(O)=CC=C1C(C)(C)C1=CC=C(O)C=C1OC(C)C SXONZCYCWKRIEM-UHFFFAOYSA-N 0.000 claims 4
BKSQGEDXPJHIKI-UHFFFAOYSA-N 4-[2-[2-[2-(4-hydroxybutoxy)phenyl]propan-2-yl]phenoxy]butan-1-ol Chemical compound C=1C=CC=C(OCCCCO)C=1C(C)(C)C1=CC=CC=C1OCCCCO BKSQGEDXPJHIKI-UHFFFAOYSA-N 0.000 claims 4
229910044991 metal oxide Inorganic materials 0.000 claims 2
150000004706 metal oxides Chemical class 0.000 claims 2
229910000859 α-Fe Inorganic materials 0.000 claims 2
KQTPNPSLJIPAGS-UHFFFAOYSA-N 3-ethoxy-4-[2-(2-ethoxy-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound CCOC1=CC(O)=CC=C1C(C)(C)C1=CC=C(O)C=C1OCC KQTPNPSLJIPAGS-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
-1 alkylene radicals Chemical class 0.000 description 21
239000000049 pigment Substances 0.000 description 10
239000000155 melt Substances 0.000 description 7
229930185605 Bisphenol Natural products 0.000 description 6
125000002947 alkylene group Chemical group 0.000 description 6
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
150000001991 dicarboxylic acids Chemical class 0.000 description 5
238000002156 mixing Methods 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
125000000732 arylene group Chemical group 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000002411 adverse Effects 0.000 description 3
125000001118 alkylidene group Chemical group 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
238000001694 spray drying Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
238000005054 agglomeration Methods 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000001273 butane Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
229940090961 chromium dioxide Drugs 0.000 description 2
IAQWMWUKBQPOIY-UHFFFAOYSA-N chromium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Cr+4] IAQWMWUKBQPOIY-UHFFFAOYSA-N 0.000 description 2
AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium(IV) oxide Inorganic materials O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
ZHQLTKAVLJKSKR-UHFFFAOYSA-N homophthalic acid Chemical compound OC(=O)CC1=CC=CC=C1C(O)=O ZHQLTKAVLJKSKR-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
125000005702 oxyalkylene group Chemical group 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000001384 succinic acid Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
CXENHBSYCFFKJS-OXYODPPFSA-N (Z,E)-alpha-farnesene Chemical compound CC(C)=CCC\C(C)=C\C\C=C(\C)C=C CXENHBSYCFFKJS-OXYODPPFSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000164466 Palaemon adspersus Species 0.000 description 1
241001307210 Pene Species 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
238000013019 agitation Methods 0.000 description 1
238000007605 air drying Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
238000000889 atomisation Methods 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
NVIVJPRCKQTWLY-UHFFFAOYSA-N cobalt nickel Chemical compound [Co][Ni][Co] NVIVJPRCKQTWLY-UHFFFAOYSA-N 0.000 description 1
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
230000001419 dependent effect Effects 0.000 description 1
DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
238000012674 dispersion polymerization Methods 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000007970 homogeneous dispersion Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 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
238000011068 loading method Methods 0.000 description 1
239000006249 magnetic particle Substances 0.000 description 1
230000005415 magnetization Effects 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
238000003801 milling Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000006353 oxyethylene group Chemical group 0.000 description 1
229910000889 permalloy Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
SIBIBHIFKSKVRR-UHFFFAOYSA-N phosphanylidynecobalt Chemical compound [Co]#P SIBIBHIFKSKVRR-UHFFFAOYSA-N 0.000 description 1
108091008695 photoreceptors Proteins 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229940051841 polyoxyethylene ether Drugs 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229940116353 sebacic acid Drugs 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000004381 surface treatment Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
MAZWDMBCPDUFDJ-UHFFFAOYSA-N trans-Traumatinsaeure Natural products OC(=O)CCCCCCCCC=CC(O)=O MAZWDMBCPDUFDJ-UHFFFAOYSA-N 0.000 description 1
MAZWDMBCPDUFDJ-VQHVLOKHSA-N traumatic acid Chemical compound OC(=O)CCCCCCCC\C=C\C(O)=O MAZWDMBCPDUFDJ-VQHVLOKHSA-N 0.000 description 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical group OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 1

Landscapes

Developing Agents For Electrophotography (AREA)

CA000369282A 1980-01-28 1981-01-26 Toner magnetique comprenant une resine qui est le produit d'esterification polymerique d'un acide dicarboxylique et d'un diphenol Expired CA1156084A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US155,974		1980-01-28
US115,973		1980-01-28
US06/115,973 US4271248A (en)	1980-01-28	1980-01-28	Magnetic latent image toner material and process for its use in flash fusing developing
US06/155,974 US4336556A (en)	1979-06-08	1980-06-03	Solid-state image pick-up device

Publications (1)

Publication Number	Publication Date
CA1156084A true CA1156084A (fr)	1983-11-01

Family

ID=26813774

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000369282A Expired CA1156084A (fr)	1980-01-28	1981-01-26	Toner magnetique comprenant une resine qui est le produit d'esterification polymerique d'un acide dicarboxylique et d'un diphenol

Country Status (1)

Country	Link
CA (1)	CA1156084A (fr)

1981
- 1981-01-26 CA CA000369282A patent/CA1156084A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-11-01	MKEX	Expiry

Publication	Publication Date	Title
US4600675A (en)	1986-07-15	Magnetic carrier for electrostatic latent image development
JPH0713752B2 (ja)	1995-02-15	電子写真用トナ−
JPH0363065B2 (fr)	1991-09-27
US4271248A (en)	1981-06-02	Magnetic latent image toner material and process for its use in flash fusing developing
US4288516A (en)	1981-09-08	Polyester resin containing magnetic toner material and process for its use in flash fuser
CA1155699A (fr)	1983-10-25	Toners magnetiques contenant de la magnetite cubique
US4847176A (en)	1989-07-11	Binder-type carrier
US4293627A (en)	1981-10-06	Process of developing magnetic images and dry magnetic toner compositions
JPS6357785B2 (fr)	1988-11-14
CA1156084A (fr)	1983-11-01	Toner magnetique comprenant une resine qui est le produit d'esterification polymerique d'un acide dicarboxylique et d'un diphenol
JPH0673024B2 (ja)	1994-09-14	電子写真用トナ−
KR910007723B1 (ko)	1991-09-30	정전하상 현상용 토너
JPS5929257A (ja)	1984-02-16	熱定着性乾式トナ−
US4822709A (en)	1989-04-18	Binder-type carrier suitable for a developing method of electrostatic latent images
EP0033248A1 (fr)	1981-08-05	Toner magnétique et procédé de développement l'utilisant
US5296327A (en)	1994-03-22	Toner powder for the development of latent electrostatic or magnetic images and a process for forming fixed images on an image receiving material
JP4116534B2 (ja)	2008-07-09	磁性トナー
JP3356548B2 (ja)	2002-12-16	静電荷像現像用トナー
JPS61284772A (ja)	1986-12-15	熱定着性乾式現像剤
JPH0685092B2 (ja)	1994-10-26	電子写真用トナ−
JPH09146295A (ja)	1997-06-06	現像方法及び電子写真用トナー
US4282296A (en)	1981-08-04	High speed magnetographic imaging process
JPS62195679A (ja)	1987-08-28	電子写真用現像剤組成物
JPH03212653A (ja)	1991-09-18	静電潜像現像用トナー
JPH09152742A (ja)	1997-06-10	トナーバインダー用ポリエステル樹脂およびこれを用いたトナー