CA2773805C - Polyester resin comprising a biopolyol - Google Patents
Polyester resin comprising a biopolyol Download PDFInfo
- Publication number
- CA2773805C CA2773805C CA2773805A CA2773805A CA2773805C CA 2773805 C CA2773805 C CA 2773805C CA 2773805 A CA2773805 A CA 2773805A CA 2773805 A CA2773805 A CA 2773805A CA 2773805 C CA2773805 C CA 2773805C
- Authority
- CA
- Canada
- Prior art keywords
- toner
- acid
- resin
- toner composition
- poly
- 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 - Fee Related
Links
- 229920001225 polyester resin Polymers 0.000 title claims abstract description 53
- 239000004645 polyester resin Substances 0.000 title claims abstract description 53
- 239000000203 mixture Substances 0.000 claims abstract description 89
- 238000004132 cross linking Methods 0.000 claims abstract description 16
- 239000002245 particle Substances 0.000 claims description 131
- 229920005989 resin Polymers 0.000 claims description 83
- 239000011347 resin Substances 0.000 claims description 83
- 238000000034 method Methods 0.000 claims description 41
- 229920005862 polyol Polymers 0.000 claims description 38
- 150000003077 polyols Chemical class 0.000 claims description 36
- 238000004220 aggregation Methods 0.000 claims description 24
- 230000002776 aggregation Effects 0.000 claims description 23
- 239000000839 emulsion Substances 0.000 claims description 22
- 238000003384 imaging method Methods 0.000 claims description 22
- 229920000728 polyester Polymers 0.000 claims description 22
- 239000003086 colorant Substances 0.000 claims description 21
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 18
- 239000004094 surface-active agent Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 15
- 230000004931 aggregating effect Effects 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 12
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 235000010355 mannitol Nutrition 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
- 229930195725 Mannitol Natural products 0.000 claims description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 8
- 239000000539 dimer Substances 0.000 claims description 8
- CDAISMWEOUEBRE-UHFFFAOYSA-N inositol Chemical compound OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 8
- 239000000594 mannitol Substances 0.000 claims description 8
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 7
- 239000008103 glucose Substances 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- 229920006127 amorphous resin Polymers 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 5
- ODEHMIGXGLNAKK-OESPXIITSA-N 6-kestotriose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 ODEHMIGXGLNAKK-OESPXIITSA-N 0.000 claims description 5
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims description 5
- MUPFEKGTMRGPLJ-OBAJZVCXSA-N Gentianose Natural products O(C[C@@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@H](O)[C@@H](CO)O2)O1)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-OBAJZVCXSA-N 0.000 claims description 5
- FLDFNEBHEXLZRX-DLQNOBSRSA-N Nystose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(O[C@@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 FLDFNEBHEXLZRX-DLQNOBSRSA-N 0.000 claims description 5
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 claims description 5
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 5
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 5
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 5
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 claims description 5
- MUPFEKGTMRGPLJ-WSCXOGSTSA-N gentianose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-WSCXOGSTSA-N 0.000 claims description 5
- 239000000832 lactitol Substances 0.000 claims description 5
- 235000010448 lactitol Nutrition 0.000 claims description 5
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 claims description 5
- 229960003451 lactitol Drugs 0.000 claims description 5
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 claims description 5
- 239000000845 maltitol Substances 0.000 claims description 5
- 235000010449 maltitol Nutrition 0.000 claims description 5
- 229940035436 maltitol Drugs 0.000 claims description 5
- FLDFNEBHEXLZRX-UHFFFAOYSA-N nystose Natural products OC1C(O)C(CO)OC1(CO)OCC1(OCC2(OC3C(C(O)C(O)C(CO)O3)O)C(C(O)C(CO)O2)O)C(O)C(O)C(CO)O1 FLDFNEBHEXLZRX-UHFFFAOYSA-N 0.000 claims description 5
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 claims description 5
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 claims description 5
- 235000000346 sugar Nutrition 0.000 claims description 5
- 239000000811 xylitol Substances 0.000 claims description 5
- 235000010447 xylitol Nutrition 0.000 claims description 5
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 5
- 229960002675 xylitol Drugs 0.000 claims description 5
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- 150000005846 sugar alcohols Chemical class 0.000 claims description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 239000004386 Erythritol Substances 0.000 claims description 3
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- 239000000701 coagulant Substances 0.000 claims description 3
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 3
- 235000019414 erythritol Nutrition 0.000 claims description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 3
- 229940009714 erythritol Drugs 0.000 claims description 3
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims description 3
- 229920000223 polyglycerol Polymers 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004220 glutamic acid Substances 0.000 claims description 2
- 235000013922 glutamic acid Nutrition 0.000 claims description 2
- SERLAGPUMNYUCK-DCUALPFSSA-N 1-O-alpha-D-glucopyranosyl-D-mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SERLAGPUMNYUCK-DCUALPFSSA-N 0.000 claims 4
- 239000004382 Amylase Substances 0.000 claims 4
- 102000013142 Amylases Human genes 0.000 claims 4
- 108010065511 Amylases Proteins 0.000 claims 4
- 235000019418 amylase Nutrition 0.000 claims 4
- 239000000905 isomalt Substances 0.000 claims 4
- 235000010439 isomalt Nutrition 0.000 claims 4
- HPIGCVXMBGOWTF-UHFFFAOYSA-N isomaltol Natural products CC(=O)C=1OC=CC=1O HPIGCVXMBGOWTF-UHFFFAOYSA-N 0.000 claims 4
- 125000004185 ester group Chemical group 0.000 claims 1
- -1 rapeseed Chemical class 0.000 description 105
- 229920000642 polymer Polymers 0.000 description 73
- 239000001993 wax Substances 0.000 description 40
- 239000003513 alkali Substances 0.000 description 36
- 239000000049 pigment Substances 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 239000003153 chemical reaction reagent Substances 0.000 description 29
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 29
- 239000000654 additive Substances 0.000 description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 238000004581 coalescence Methods 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 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 18
- 229910052799 carbon Inorganic materials 0.000 description 16
- 230000008569 process Effects 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 12
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 229930185605 Bisphenol Natural products 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 229940116351 sebacate Drugs 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000001384 succinic acid Substances 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 229920006038 crystalline resin Polymers 0.000 description 8
- 229910052725 zinc Inorganic materials 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 229960002479 isosorbide Drugs 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 229910000420 cerium oxide Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002736 nonionic surfactant Substances 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 6
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011164 primary particle Substances 0.000 description 5
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 5
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- SZLIWAKTUJFFNX-UHFFFAOYSA-N dihydrocitronellol benzoate Natural products CC(C)CCCC(C)CCOC(=O)C1=CC=CC=C1 SZLIWAKTUJFFNX-UHFFFAOYSA-N 0.000 description 4
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 4
- 229960000367 inositol Drugs 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
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- 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
- G03G9/09—Colouring agents for toner particles
-
- 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
- G03G9/093—Encapsulated toner particles
- G03G9/09307—Encapsulated toner particles specified by the shell material
- G03G9/09314—Macromolecular compounds
- G03G9/09328—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- G03G9/093—Encapsulated toner particles
- G03G9/0935—Encapsulated toner particles specified by the core material
- G03G9/09357—Macromolecular compounds
- G03G9/09371—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G2215/00—Apparatus for electrophotographic processes
- G03G2215/00953—Electrographic recording members
- G03G2215/00957—Compositions
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/088,324 | 2011-04-15 | ||
| US13/088,324 US8518624B2 (en) | 2011-04-15 | 2011-04-15 | Polyester resin comprising a biopolyol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2773805A1 CA2773805A1 (en) | 2012-10-15 |
| CA2773805C true CA2773805C (en) | 2015-04-07 |
Family
ID=47006617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2773805A Expired - Fee Related CA2773805C (en) | 2011-04-15 | 2012-04-10 | Polyester resin comprising a biopolyol |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8518624B2 (enExample) |
| JP (1) | JP5795545B2 (enExample) |
| KR (1) | KR20120117655A (enExample) |
| BR (1) | BR102012008595A2 (enExample) |
| CA (1) | CA2773805C (enExample) |
| MX (1) | MX336450B (enExample) |
| RU (1) | RU2570816C2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9290615B2 (en) * | 2012-06-13 | 2016-03-22 | Mitsubishi Rayon Co., Ltd. | Toner polyester resin, method for producing same, and toner |
| EP2930566B1 (en) | 2012-12-07 | 2019-07-31 | Mitsubishi Chemical Corporation | Polyester resin for toners, method for producing same, and toner |
| EP2935395A2 (en) * | 2012-12-20 | 2015-10-28 | Dow Global Technologies LLC | Ndca-based polyesters made with isosorbide |
| US9580594B2 (en) | 2012-12-20 | 2017-02-28 | Dow Global Technologies Llc | FDCA-based polyesters |
| CN104968716A (zh) | 2012-12-20 | 2015-10-07 | 陶氏环球技术有限责任公司 | 乙交酯基聚酯 |
| US9394402B2 (en) | 2012-12-20 | 2016-07-19 | Dow Global Technologies Llc | Glycolide-based polyesters made with isosorbide |
| EP2934890B1 (en) | 2012-12-20 | 2018-09-26 | Dow Global Technologies LLC | Multilayer films of fdca-based polyesters |
| US9909013B2 (en) * | 2016-04-13 | 2018-03-06 | Xerox Corporation | Silver nanoparticle-sulfonated polyester composite powders and methods of making the same |
| US9877485B2 (en) * | 2016-04-13 | 2018-01-30 | Xerox Corporation | Silver polyester-sulfonated nanoparticle composite filaments and methods of making the same |
| US9908977B2 (en) * | 2016-04-13 | 2018-03-06 | Xerox Corporation | Styrenic-based polymer coated silver nanoparticle-sulfonated polyester composite powders and methods of making the same |
| US9863065B2 (en) * | 2016-04-13 | 2018-01-09 | Xerox Corporation | Polymer coated sulfonated polyester—silver nanoparticle composite filaments and methods of making the same |
| JP7024946B2 (ja) * | 2017-11-29 | 2022-02-24 | 花王株式会社 | トナー用縮重合樹脂の製造方法 |
| CN115850950B (zh) * | 2022-12-21 | 2024-06-11 | 安徽远征传导科技股份有限公司 | 一种新能源汽车用移动抗曲挠交流充电枪电缆 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58100139A (ja) * | 1981-12-09 | 1983-06-14 | Canon Inc | 熱ロ−ル定着用トナ− |
| JPH0354574A (ja) * | 1989-07-21 | 1991-03-08 | Mitsubishi Rayon Co Ltd | トナー用ポリエステル樹脂及びその製造方法 |
| JP3060588B2 (ja) * | 1990-05-31 | 2000-07-10 | ミノルタ株式会社 | 一成分現像用トナー |
| US6692802B1 (en) * | 1997-08-27 | 2004-02-17 | Reichhold, Inc. | Resins for lining surfaces |
| JP3984335B2 (ja) | 1997-09-17 | 2007-10-03 | 三菱レイヨン株式会社 | トナー用ポリエステル樹脂、その製造方法およびそれを用いたトナー |
| CA2458116C (en) * | 2002-06-13 | 2011-12-13 | Dainippon Ink And Chemicals, Inc. | Aqueous resin composition |
| AU2006227196B2 (en) | 2005-03-18 | 2010-11-25 | Battelle Memorial Institute | Toner |
| US8007978B2 (en) * | 2006-03-03 | 2011-08-30 | Dow Global Technologies Llc | Aqueous dispersions for use as toners |
| JP5111956B2 (ja) * | 2006-07-31 | 2013-01-09 | 花王株式会社 | 樹脂乳化液 |
| US7858285B2 (en) * | 2006-11-06 | 2010-12-28 | Xerox Corporation | Emulsion aggregation polyester toners |
| JP4760690B2 (ja) * | 2006-12-04 | 2011-08-31 | 富士ゼロックス株式会社 | 静電荷像現像用トナー及びその製造方法、並びに静電荷像現像剤、トナーカートリッジ、プロセスカートリッジ及び画像形成装置 |
| US7754406B2 (en) * | 2007-02-08 | 2010-07-13 | Xerox Corporation | Ultra low melt emulsion aggregation toners having a charge control agent |
| US20080197283A1 (en) * | 2007-02-16 | 2008-08-21 | Xerox Corporation | Emulsion aggregation toner compositions and developers |
| JP5473252B2 (ja) | 2008-06-02 | 2014-04-16 | 株式会社リコー | トナー、現像剤、及び画像形成方法 |
| US8962228B2 (en) | 2008-09-19 | 2015-02-24 | Xerox Corporation | Low melt color toners with fluorescence agents |
-
2011
- 2011-04-15 US US13/088,324 patent/US8518624B2/en active Active
-
2012
- 2012-03-21 JP JP2012063659A patent/JP5795545B2/ja active Active
- 2012-04-09 MX MX2012004181A patent/MX336450B/es unknown
- 2012-04-10 CA CA2773805A patent/CA2773805C/en not_active Expired - Fee Related
- 2012-04-10 KR KR1020120037173A patent/KR20120117655A/ko not_active Ceased
- 2012-04-12 BR BRBR102012008595-0A patent/BR102012008595A2/pt not_active Application Discontinuation
- 2012-04-13 RU RU2012114695/04A patent/RU2570816C2/ru not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2570816C2 (ru) | 2015-12-10 |
| CA2773805A1 (en) | 2012-10-15 |
| JP5795545B2 (ja) | 2015-10-14 |
| US20120264047A1 (en) | 2012-10-18 |
| MX336450B (es) | 2016-01-20 |
| RU2012114695A (ru) | 2013-10-20 |
| KR20120117655A (ko) | 2012-10-24 |
| MX2012004181A (es) | 2012-10-29 |
| JP2012226318A (ja) | 2012-11-15 |
| BR102012008595A2 (pt) | 2013-06-04 |
| US8518624B2 (en) | 2013-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20210412 |