WO2015045888A1 - 電子写真トナー用ポリエステル樹脂組成物及び電子写真トナー - Google Patents
電子写真トナー用ポリエステル樹脂組成物及び電子写真トナー Download PDFInfo
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- WO2015045888A1 WO2015045888A1 PCT/JP2014/074111 JP2014074111W WO2015045888A1 WO 2015045888 A1 WO2015045888 A1 WO 2015045888A1 JP 2014074111 W JP2014074111 W JP 2014074111W WO 2015045888 A1 WO2015045888 A1 WO 2015045888A1
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- Prior art keywords
- polyester resin
- electrophotographic toner
- acid
- resin composition
- compound
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- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
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- XVBXJBGOQQLLAO-UHFFFAOYSA-J [Ti+4].C=C.OCC([O-])=O.OCC([O-])=O.OCC([O-])=O.OCC([O-])=O Chemical compound [Ti+4].C=C.OCC([O-])=O.OCC([O-])=O.OCC([O-])=O.OCC([O-])=O XVBXJBGOQQLLAO-UHFFFAOYSA-J 0.000 description 1
- XHEFTAKYQGYNNZ-UHFFFAOYSA-N [Ti].P(O)O Chemical compound [Ti].P(O)O XHEFTAKYQGYNNZ-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- CUSQEGUGRNCRHL-UHFFFAOYSA-N benzene-1,3-diol;propan-2-one Chemical compound CC(C)=O.OC1=CC=CC(O)=C1 CUSQEGUGRNCRHL-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 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
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- BYYQOWAAZOHHFN-UHFFFAOYSA-N dioctylphosphane Chemical compound CCCCCCCCPCCCCCCCC BYYQOWAAZOHHFN-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- BYRBYEZLJWXGTQ-UHFFFAOYSA-N ethene;phosphane Chemical group P.C=C BYRBYEZLJWXGTQ-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000006233 lamp black 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
- 150000002611 lead compounds Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 1
- QTDSLDJPJJBBLE-PFONDFGASA-N octyl (z)-octadec-9-enoate Chemical compound CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC QTDSLDJPJJBBLE-PFONDFGASA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- JPYKDIMLXREUBW-UHFFFAOYSA-N phosphane titanium Chemical class P.[Ti] JPYKDIMLXREUBW-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- HMXCZSOLWMJNGA-UHFFFAOYSA-N titanium(4+);tetraphosphite Chemical class [Ti+4].[Ti+4].[Ti+4].[O-]P([O-])[O-].[O-]P([O-])[O-].[O-]P([O-])[O-].[O-]P([O-])[O-] HMXCZSOLWMJNGA-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 150000003755 zirconium compounds Chemical class 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
- G03G9/087—Binders for toner particles
- G03G9/08742—Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08755—Polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08742—Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08753—Epoxyresins
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08797—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature
Definitions
- the present invention relates to a polyester resin composition capable of obtaining an electrophotographic toner excellent in charge amount, charge stability, low-temperature fixability and offset resistance, and an electrophotographic toner containing the same.
- electrophotographic toner that is used in such an electrophotographic method and has excellent chargeability and charge stability
- an electrophotographic toner for example, a polybasic acid, a polyhydric alcohol, and a plurality of epoxy compounds having different epoxy group contents are used in combination.
- An electrophotographic toner using a polyester resin is known (for example, see Patent Documents 1 and 2).
- Patent Documents 1 and 2 do not have a good balance of low-temperature fixability, offset resistance, chargeability, and charge stability. Fixability has been demanded, and it is not enough to meet such demands.
- an object of the present invention is to provide a polyester resin composition that can provide an electrophotographic toner that is excellent in low-temperature fixability and offset resistance, and has good charge amount and charge stability, and an electron that contains the same. It is to provide photographic toner.
- the present invention relates to a monobasic acid (a1), a polybasic acid (a2), a polyhydric alcohol (a3), a monoepoxy compound (a4), and a polyepoxy compound (a5) having four or more epoxy groups.
- the present invention provides a polyester resin composition for an electrophotographic toner, which contains a polyester resin (A) obtained by reacting the above.
- the present invention also provides an electrophotographic toner comprising the polyester resin composition for an electrophotographic toner.
- the electrophotographic toner obtained using the composition of the present invention has a well-balanced balance of fixability at lower temperatures, anti-offset properties, chargeability and charge stability, and the required level of toner is increased. It can be used suitably in the application which has come.
- the polyester resin (A) used in the present invention includes a monobasic acid (a1), a polybasic acid (a2), a polyhydric alcohol (a3), a monoepoxy compound (a4), and a polyepoxy having four or more epoxy groups. It is obtained by reacting compound (a5).
- the molecular weight distribution is widened, or the terminal of the polyfunctional epoxy compound as a crosslinking agent and the terminal hydroxyl group of the polyester are blocked with the monobasic acid (a1).
- the crosslinking density can be further improved (a gel content can be obtained while suppressing an increase in melt viscosity), and a polyester resin containing a gel content (a component that does not dissolve in tetrahydrofuran) can be easily obtained.
- an electrophotographic toner having both a fixing property at a temperature lower than that of the prior art and a high-temperature offset resistance and a good charging property.
- the monobasic acid (a1) used in the present invention is not particularly limited, and examples thereof include benzoic acid, p-substituted benzoic acid, o-substituted benzoic acid, acetic acid, propionic acid, and butyric acid. From the standpoint that the toner can have a higher molecular weight and good low-temperature fixability, has better crushability, and can further improve the chargeability and charge stability of the resulting toner, Acids are preferred, benzoic acid and p-substituted benzoic acid are particularly preferred, and paratertiary butylbenzoic acid is most preferred.
- polybasic acid (a2) used in the present invention a saturated polybasic acid, an unsaturated polybasic acid, etc., their acid anhydrides, and lower alkyl esters thereof can be used.
- saturated polybasic acid, saturated polybasic acid and lower alkyl ester of saturated polybasic acid include, for example, adipic acid, sebacic acid, orthophthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, succinic acid, succinic anhydride, Dibasic acids such as alkyl succinic acid having 8 to 18 carbon atoms, alkyl succinic anhydride, alkenyl succinic acid, alkenyl succinic anhydride; trimellitic acid, trimellitic anhydride, cyanuric acid, pyromellitic acid, pyromellitic anhydride And polybasic acids.
- unsaturated polybasic acid include maleic acid, maleic anhydride, fumaric acid, etc., and these may be used alone or in combination of two or more.
- polybasic acids (a2) one or more compounds selected from the group consisting of divalent basic acids, anhydrides thereof, and lower alkyl esters thereof can be obtained because a toner excellent in offset resistance and low-temperature fixability can be obtained.
- the polybasic acid containing is preferable, and isophthalic acid and terephthalic acid are more preferable among the one or more compounds selected from the group consisting of the divalent basic acid, its anhydride, and these lower alkyl esters.
- polybasic acid (a2) those in which part or all of the carboxy group is alkenyl ester or allyl ester can also be used.
- the use ratio of the monobasic acid (a1) and the polybasic acid (a2) is such that (a1) / (a2) is 1/99 to 30 / from the viewpoint of obtaining an electrophotographic toner having better low-temperature fixability. 70 (mass ratio) is preferable, and 2/98 to 26/74 is particularly preferable.
- Examples of the polyhydric alcohol (a3) used in the present invention include divalent alcohols and trivalent or higher alcohols.
- divalent alcohols examples include aliphatic diols such as linear aliphatic diols and cycloaliphatic diols, and aromatic diols.
- linear aliphatic diol examples include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, butanediol, pentanediol, hexanediol, 2-ethyl-4-butylhexanediol, Butylethylpropanediol, 2,4-diethyl 3,5-pentadiol, polyethylene glycol, polypropylene glycol, ethylene oxide-propylene oxide random copolymer diol, ethylene oxide-propylene oxide block copolymer diol, ethylene oxide-tetrahydro Examples include furan copolymer diol and polycaprolactone diol.
- cycloaliphatic diol examples include 1,4-cyclohexanedimethanol and hydrogenated bisphenol A.
- aromatic diols examples include diols having a bisphenol skeleton.
- diols having a bisphenol skeleton include bisphenols such as bisphenol A and bisphenol F; bisphenols such as an ethylene oxide adduct of bisphenol A and a propylene oxide adduct of bisphenol A. A-alkylene oxide adduct and the like.
- trivalent or higher alcohols examples include glycerin, trimethylolethane, trimethylolpropane, pentaerythritol, dipentaerythritol, 2-methylpropanetriol, and the like.
- the polyhydric alcohol (a3) may be used alone or in combination of two or more. Moreover, you may use monoalcohols, such as a stearyl alcohol, as needed within the range which does not impair the effect of this invention.
- Examples of the monoepoxy compound (a4) used in the present invention include phenyl glycidyl ether, alkylphenyl glycidyl ether, alkyl glycidyl ether, alkyl glycidyl ester, glycidyl ether of alkylphenol alkylene oxide adduct, ⁇ -olefin oxide, monoepoxy fatty acid alkyl.
- esters and the like are examples of esters and the like.
- alkylphenyl glycidyl ether examples include cresyl glycidyl ether, butyl glycidyl ether, and nonyl glycidyl ether.
- alkyl glycidyl ether examples include butyl glycidyl ether and 2-ethylhexyl glycidyl ether.
- alkyl glycidyl ester for example, the following general formula (1)
- R is an alkyl group having 1 to 25 carbon atoms, preferably an alkyl group having 10 to 15 carbon atoms. ] And the like.
- examples of the glycidyl ether of the alkylphenol alkylene oxide adduct include a glycidyl ether of a compound obtained by adding an alkylene oxide such as ethylene oxide or propylene oxide to a lower alkylphenol such as butylphenol, and specific examples include ethylene glycol monophenyl.
- Glycidyl ether of ether glycidyl ether of polyethylene glycol monophenyl ether, glycidyl ether of propylene glycol monophenyl ether, glycidyl ether of polypropylene glycol monophenyl ether, glycidyl ether of propylene glycol mono (pt-butyl) phenyl ether, ethylene glycol
- ⁇ -olefin oxide examples include compounds obtained by oxidizing olefins such as alpha olefin oxide-168 [Adeka Argus Chemical Co., Ltd. product] and alpha olefin oxide-124 [Adeka Argus Chemical Co., Ltd. product].
- the monoepoxy fatty acid alkyl ester for example, a compound obtained by epoxidizing an unsaturated group of an alcohol ester of an unsaturated fatty acid, such as an epoxidized oleic acid butyl ester, the following structural formula (2)
- the monoepoxy compound represented by the general formula (1) is more preferable because the obtained polyester resin (A) has good affinity with wax.
- the polyepoxy compound (a5) having four or more epoxy groups used in the present invention is mainly used to increase the crosslinking density in the polyester resin.
- a novolac type epoxy resin a dicyclopentadiene type epoxy is used.
- polyepoxy compounds (a5) having four or more epoxy groups used in the present invention an electrophotographic toner having excellent low-temperature fixability and high-temperature offset resistance, and good charge amount and charge stability can be obtained.
- a novolac type epoxy resin is preferred.
- novolac type epoxy resins for example, cresol novolac type epoxy resin, phenol novolac type epoxy resin, bisphenol A novolac type epoxy resin, bisphenol A alkylene oxide adduct type novolac type epoxy resin, bisphenol F alkylene oxide adduct type
- One or more novolac epoxy resins selected from the group consisting of novolac epoxy resins, naphthalene type novolac epoxy resins and dicyclopentadiene type novolac epoxy resins are preferred.
- a cresol novolac type epoxy resin, a bisphenol A novolak type epoxy resin, and a phenol novolak type epoxy resin are more desirable.
- the polyepoxy compound (a5) having 4 or more epoxy groups used in the present invention is preferably a novolak type epoxy resin having 4 to 15 epoxy groups.
- the total mass of the monoepoxy compound (a4) and the polyepoxy compound (a5) having 4 or more epoxy groups when used in a range of 0.5 to 10% by mass with respect to the total mass of all charged raw materials, it is preferable because an electrophotographic toner having excellent low-temperature fixability and high-temperature offset resistance and good charging stability can be obtained, and more preferably used in the range of 0.6 to 9% by mass.
- polyester resin (A) used in the present invention a monobasic acid (a1), a polybasic acid (A1)
- the basic acid (a2), the polyhydric alcohol (a3), the monoepoxy compound (a4), and the polyepoxy compound (a5) having four or more epoxy groups are added to the total mass of (a1) to (a5).
- Polyester resins obtained by using 0.5 to 8 parts by weight, 25 to 75 parts by weight, 20 to 75 parts by weight, 0.1 to 2 parts by weight and 0.4 to 8 parts by weight, respectively, are preferable, Polyester resins obtained by using 1 to 7 parts by weight, 30 to 70 parts by weight, 20 to 65 parts by weight, 0.1 to 2 parts by weight and 0.5 to 7 parts by weight, respectively, based on the total weight of (a5) Is more preferable.
- a polyester resin (A) used by this invention a monoepoxy compound (a4) and 4 or more with respect to the said monobasic acid (a1) from a viewpoint of the balance of low-temperature fixability and high temperature offset resistance.
- the total mass ratio [a1 / [a4 + a5]] of the polyepoxy compound (a5) having an epoxy group is preferably in the range of 3/97 to 70/30.
- the polyester resin (A) used in the present invention is arbitrarily produced by a known polycondensation reaction method.
- a known polycondensation reaction method for example, in the presence of an esterification catalyst (tin compound, titanium compound, zirconium compound, etc.) or in the presence of a transesterification catalyst (lead compound, tin compound, zinc compound, titanium compound, etc.), lower alkyl such as dicarboxylic acid methyl ester
- the transesterification reaction using an ester, normal pressure dehydration reaction, reduced pressure and vacuum dehydration reaction, solution polycondensation method, solid phase polycondensation reaction and any other production method may be used.
- the polyesterification reaction at this time can be traced by measuring the acid value, hydroxyl value, viscosity or softening point.
- a batch production apparatus such as a reaction vessel equipped with a nitrogen inlet, a thermometer, a stirrer, a rectifying tower, and the like can be suitably used, and a deaeration port is provided.
- An extruder, a continuous reaction apparatus, a kneader or the like can also be used.
- the esterification reaction can be promoted by reducing the pressure of the reaction system as necessary.
- the monobasic acid (a1) which is a raw material from the viewpoint of excellent balance between low-temperature fixability, high-temperature offset resistance and chargeability, and capable of efficiently obtaining a polyester resin having a gel fraction and viscoelasticity described later.
- the polybasic acid (a2), the polyhydric alcohol (a3), the monoepoxy compound (a4), and the polyepoxy compound (a5) having four or more epoxy groups are dissolved and mixed, and an esterification catalyst is added thereto. It is preferable that the temperature is raised before the reaction (so-called batch charging method).
- polyester resin (A) used in the present invention polycondensation is performed in the presence of a titanium compound in which a phosphorus compound is covalently bonded and / or a titanium compound in which a phosphorus compound is coordinated as a titanium compound. ) Is preferable because it becomes a transparent polyester resin in which coloring is suppressed.
- the titanium compound is a titanium compound covalently bonded to a phosphorus compound and a titanium compound coordinated to a phosphorus compound.
- examples of the titanium compound to which the phosphorus compound is covalently bonded include a titanium compound having a structure in which the phosphorus compound is bonded to the titanium compound through an ether bond of the phosphorus compound.
- examples of the titanium compound in which the phosphorus compound is coordinate-bonded include a titanium compound having a structure bonded to the titanium compound via an unshared electron pair of the phosphorus compound.
- Examples of such compounds include phosphate titanium compounds, phosphite titanium compounds, phosphonic acid titanium compounds, phosphonic acid titanium compounds, phosphinic acid titanium compounds, phosphinic acid titanium compounds, Examples include phosphine oxide acid titanium compounds and phosphine titanium compounds.
- Examples of the phosphate titanium compound include a monophosphate titanium compound, a bisphosphate titanium compound, and a trisphosphate titanium compound.
- Examples of the monophosphate titanium compound include triisopropoxy titanium / dioctyl phosphate, triisopropoxy titanium / dioctyl pyrophosphate, tributoxy titanium / dioctyl phosphate, tributoxy titanium / dioctyl pyrophosphate, tri-2-ethylhexyloxytitanium / Examples include dioctyl phosphate, tri-2-ethylhexyloxytitanium / dioctylpyrophosphate, tristearoxytitanium / dioctylphosphate, tristealkoxytitanium / dioctylpyrophosphate, and the like.
- bisphosphate titanium compound examples include diisopropoxy titanium / bisdioctyl phosphate, diisopropoxy titanium / bisdioctyl pyrophosphate, dibutoxy titanium / bisdioctyl phosphate, dibutoxy titanium / bisdioctyl pyrophosphate, Ethylhexyloxytitanium / bisdioctylphosphate, G-2-ethylhexyloxytitanium / bisdioctylpyrophosphate, distearoxytitanium / bisdioctylphosphate, distearoxytitanium / bisdioctylpyrophosphate, bisdioctylphosphate ethylene glycolatotitanium, bisdioctylpyro Phosphate / ethylene glycolato titanium, titanium / bisdioctyl pyrophosphate oxyacetate,
- trisphosphate titanium compound examples include isopropoxy titanium / trisoctyl phosphate, isopropoxy titanium / tris dioctyl pyrophosphate, butoxy titanium / tris dioctyl phosphate, butoxy titanium / tris dioctyl pyrophosphate, 2-ethylhexyloxy titanium / tris dioctyl phosphate. 2-ethylhexyloxytitanium / trisdioctylpyrophosphate, stearoxytitanium / trisdioctylphosphate, stearoxytitanium / trisdioctylpyrophosphate, and the like.
- Examples of the phosphite-based titanium compound include a monophosphite-based titanium compound, a bisphosphite-based titanium compound, and a trisphosphite-based titanium compound.
- Examples of the monophosphite-based titanium compound include triisopropoxy titanium / dioctyl phosphite, tributoxy titanium / dioctyl phosphite, tri-2-ethylhexyloxy titanium / dioctyl phosphite, and tristearoxy titanium / dioctyl phosphite. It is done.
- the bisphosphite-based titanium compound examples include diisopropoxy titanium / bisdioctyl phosphite, dibutoxy titanium / bisdioctyl phosphite, di-2-ethylhexyloxytitanium / bisdioctyl phosphite, distearoxy titanium / bisdioctyl.
- examples thereof include phosphite, bisdioctyl phosphite ethylene glycolate titanium, titanium / bisdioctyl phosphite oxyacetate, and tetraisopropoxytitanium / bisdioctyl phosphite.
- trisphosphite-based titanium compound examples include isopropoxy titanium / trisoctyl phosphite, butoxy titanium / tris dioctyl phosphite, 2-ethylhexyloxy titanium / tris dioctyl phosphite, stearoxy titanium / tris dioctyl phosphite, Examples include propoxy titanium and trisdioctyl phosphite.
- Examples of the phosphonic acid-based titanium compound include isopropoxytitanium / trisdioctylphosphonic acid, bisdioctylphosphonic acid ethylene glycolatotitanium, isopropoxytitanium / bisdioctylphosphonic acid, and the like.
- Examples of the phosphonous acid titanium compound include isopropoxy titanium / trisdioctyl phosphonous acid, bisdioctyl phosphonous acid ethylene glycolato titanium, isopropoxy titanium / bisdioctyl phosphonous acid, and the like.
- phosphinic acid titanium compound examples include isopropoxy titanium / tris octyl phosphinic acid, bisoctyl phosphinic acid ethylene glycolato titanium, isopropoxy titanium / bis octyl phosphinic acid, and the like.
- phosphinic acid titanium compound examples include isopropoxy titanium / trisoctyl phosphinic acid, bisoctyl phosphinic acid ethylene glycolate titanium, isopropoxy titanium / bisoctyl phosphinic acid, and the like.
- Examples of the phosphine oxide acid-based titanium compound include isopropoxy titanium / trisdioctyl phosphine oxide, isopropoxy titanium / trisdioctyl phosphine oxide, bisdioctyl phosphine oxide ethylene glycolato titanium, bisdioctyl phosphine oxide ethylene glycolato titanium, isopropoxy.
- Examples include titanium / bisdioctylphosphine oxide, isopropoxytitanium / bisdioctylphosphine oxide, and the like.
- Examples of the phosphinic acid titanium compound include isopropoxy titanium / trisdioctyl phosphine, isopropoxy titanium / tris dioctyl phosphine, bisdioctyl phosphine ethylene glycolato titanium, bis dioctyl phosphine ethylene glycolato titanium, isopropoxy titanium / bis dioctyl.
- Examples include phosphine, isopropoxytitanium / bisdioctylphosphine, and the like.
- a polyester resin obtained by using a phosphate-based titanium compound and a phosphite-based titanium compound because an electrophotographic toner having excellent glossiness can be obtained by suppressing coloration more and becoming a highly transparent polyester resin.
- Resins are preferred, polyester resins obtained using bisphosphate titanium compounds and bisphosphite titanium compounds are more preferred, and polyester resins obtained using pyrophosphate titanium compounds are even more preferred.
- polyester resin (A) used in the present invention a polyester resin obtained by using a titanium compound having an alkylene oxide chain as a titanium compound covalently bonded to a phosphorus compound and / or a titanium compound coordinated to a phosphorus compound.
- a titanium compound having an alkylene oxide chain as a titanium compound covalently bonded to a phosphorus compound and / or a titanium compound coordinated to a phosphorus compound.
- the alkylene oxide chains an alkylene oxide chain having 2 to 22 carbon atoms is preferable.
- titanium / bisdioctyl pyrophosphate oxyacetate and diisopropoxytitanium / bisdioctyl phosphate are more preferable.
- the titanium compound covalently bonded to the phosphorus compound and / or the titanium compound coordinated to the phosphorus compound is used in an amount of 1 to 5000 ppm based on the total mass of the raw materials constituting the polyester resin (A). However, it is preferable because the polyester resin has good reaction efficiency and little coloration, and more preferably 10 to 1000 ppm.
- the mass ratio (gel fraction) of components insoluble in tetrahydrofuran at 25 ° C. is in the range of 10 to 70 mass%. In particular, the range of 20 to 60% by mass is preferable.
- the difference between the tan ⁇ value at 250 ° C. and the tan ⁇ value at 100 ° C. is preferably 1.00 or less, and more preferably 0.60 or less.
- the tan ⁇ value here is obtained by [loss elastic modulus G ′′ / storage elastic modulus G ′] in viscoelasticity measurement, that is, expressed by the following expressions (1) and (2).
- the storage elastic modulus and the loss elastic modulus are values measured by the following method.
- Measuring instrument HAAKE RS600 Measurement conditions: Strain control mode Temperature increase rate 4 ° C / min, Frequency 1Hz, Strain 5%, Measurement temperature 80-250 ° C
- the glass transition temperature (Tg) of the polyester resin (A) is preferably in the range of 45 to 90 ° C., more preferably in the range of 55 to 85 ° C.
- a polyester resin having a softening point (T1 / 2) of 90 to 210 ° C. is preferable, and a polyester resin having a temperature of 100 to 180 ° C. is more preferable, because better high temperature offset resistance can be obtained.
- a polyester resin having a glass transition temperature (Tg) of 50 to 90 ° C. and a softening point (T1 / 2) of 90 to 210 ° C. is preferable, and a glass transition temperature (Tg) of 55 to 85 ° C.
- a polyester resin having a softening point (T1 / 2) of 100 to 180 ° C. is more preferable.
- the glass transition temperature is a value measured under the following conditions.
- Measuring device Seiko Electronics Co., Ltd.
- DSC220C Measurement conditions 10 ° C./min, Sample: About 10 mg of sample is put in an aluminum container and the lid is closed.
- Measuring method DSC (Suggested scanning calorimetry) method
- the softening point (T1 / 2) was measured under the following conditions. Measuring instrument: CFT-500D manufactured by Shimadzu Corporation Measurement conditions: temperature rising rate 6 ° C./min, nozzle 1.0 mm ⁇ ⁇ 10 mm, load 10 kgf, sample amount 1.5 g
- the softening point (T1 / 2) is the temperature at which the plunger (piston) reaches the intermediate point in the process from the start of the outflow to the end of the outflow in the Koka flow tester (CFT-500D manufactured by Shimadzu Corporation).
- the resin composition for an electrophotographic toner of the present invention may contain the polyester resin, but a release agent, a colorant, a charge control agent, and the like can be added as necessary.
- release agent examples include various waxes.
- natural waxes such as montan wax, carnauba wax, candelilla wax and rice wax
- synthetic waxes such as polypropylene wax and polyethylene wax can be used.
- a release agent can be used for the purpose of preventing troubles caused by toner heat roller adhesion contamination (offset).
- a release agent include various waxes.
- natural waxes such as montan wax, carnauba wax, candelilla wax and rice wax
- synthetic waxes such as polypropylene wax and polyethylene wax
- Suitable waxes include, for example, biscol 660P and biscol 550P (manufactured by Sanyo Chemical Industries, Ltd.), which are synthetic polypropylene waxes.
- the mass ratio of the release agent in the resin composition for an electrophotographic toner of the present invention is not particularly limited, but is usually 0.3 to 15 parts by mass, preferably 1 per 100 parts by mass of the toner resin composition. Is 5 parts by mass.
- the colorant examples include various non-magnetic organic pigments and inorganic pigments, such as carbon black, aniline blue, calcoil blue, chrome yellow, ultramarine blue, phthalocyanine blue, lamp black, rose bengara, quinacridone red, A watching red etc. can be mentioned, It can use by 1 type, or 2 or more types of combination.
- the mass ratio with the colorant in the resin composition for electrophotographic toner of the present invention is not particularly limited, but usually 1 to 60 parts by mass, preferably 3 to 30 parts by mass of the colorant per 100 parts by mass of the resin composition for toner. Part.
- charge control agent examples include charge control agents such as nigrosine dyes, quaternary ammonium salts, trimethylethane dyes, copper phthalocyanine, perylene, quinacridone, azo pigments, metal complex acid dyes such as azo dyes. 1 type or 2 or more types can be used in combination.
- the mass ratio of the charge control agent in the electrophotographic toner resin composition of the present invention is not particularly limited, but preferably 0.5 to 3 charge control agent per 100 parts by mass of the toner resin composition. Part by mass is desirable.
- the resin composition for an electrophotographic toner of the present invention includes various resins such as a styrene resin, a styrene-acrylic copolymer resin, an epoxy resin, and other polyester resins as long as the effects of the present invention are not lost.
- a proper amount of silicone resin, polyurethane resin, or the like can be blended. The blending amount is usually about 1 to 30 parts by mass with respect to 100 parts by mass of the polyester resin.
- the electrophotographic toner obtained by using the electrophotographic toner resin composition of the present invention can be obtained by any production method.
- it can be obtained by melt-kneading the polyester resin and the colorant at a temperature equal to or higher than the melting point of the polyester resin, pulverizing and classifying.
- you may manufacture by a method other than this.
- various auxiliary agents such as a fluidity improver can be further added in any step of the production. It is effective to attach the fluidity improver to the surface of the electrophotographic toner.
- the toner powder obtained in the present invention can be used as it is as it is, but by adding silica externally, the powder fluidity can be further improved, which is practically preferable.
- Silica includes those having a relatively large average particle diameter and those having a relatively small average particle diameter, and these may be used alone or in combination.
- the external addition amount of silica the charge amount is necessary and sufficient, and the photosensitive drum is not damaged and the environmental characteristics of the toner are not deteriorated. From about 5.0 parts by weight is practically preferable.
- the electrophotographic toner of the present invention is excellent in charging stability.
- the electrophotographic toner of the present invention has a charge amount of ⁇ 30 ⁇ C / g to ⁇ 70 ⁇ C / g.
- the charge amount was measured according to the following conditions.
- Measuring instrument 210HS-2A blow-off charge measuring instrument manufactured by Trek Japan Co., Ltd.
- Measuring condition 25 ° C./RH 60%
- Measuring method A mixture of 1.5 g of resin and 48.5 g of ferrite carrier MF-100 (manufactured by Nippon Iron Powder Co., Ltd.) is mixed in a 50 ml plastic container for 1 minute, 10 minutes, 30 minutes, 60 minutes and charged. Measured with a measuring instrument.
- Synthesis examples 2 to 3 [same as above] Polyester resins (A2 to A3) were obtained in the same manner as in Synthesis Example 1 except that the raw materials used in Synthesis Example 1 were changed to the raw materials and amounts charged in Table 1.
- Synthesis Examples 4 to 8 [Synthesis of Comparative Polyester Resin (A ′)] Comparative polyester resins (A′1 to A′5) were obtained in the same manner as in Synthetic Example 1, except that the raw materials used in Synthesis Example 1 were changed to the raw materials and amounts charged in Table 1.
- Example 1 90 parts of polyester resin (A-1), 5 parts of carbon black MA-11 (Mitsubishi Chemical), 1 part of Bontron S34 (charge control agent made by Orient Chemical) and 4 parts of Carnauba wax are mixed with a Henschel mixer. After obtaining the polyester resin composition for an electrophotographic toner of the invention, the mixture was kneaded with a biaxial kneader to obtain a kneaded product. The kneaded material thus obtained was finely pulverized and classified with an AFG100 / ATP50 (jet mill / classifier manufactured by Hosokawa Micron).
- AFG100 / ATP50 jet mill / classifier manufactured by Hosokawa Micron
- Examples 2 and 3 and Comparative Examples 1 to 5 The electrophotographic toners of Examples 2-3 and Comparative Examples 1-5 are the same as Example 1 except that the polyester resins obtained in Synthesis Examples 2-8 are used instead of the polyester resin (A-1). Were prepared and evaluated for each item. The results are shown in Table 2.
- the fastness test was conducted using a Gakushin type friction fastness tester (load: 200 g, rubbing operation: 5 strokes).
- the fixing start temperature and offset resistance were evaluated under the following heat roller fixing machine conditions.
- Roll material Upper; Polytetrafluoroethylene, Lower; Silicone Upper roll load: 7Kg / 350mm Nip width: 4mm Paper threading speed: 90mm / sec
- the difference between the maximum charge amount and the minimum charge amount is obtained for the charge amount measured by a charge amount measuring device after mixing for 10 minutes, 30 minutes and 60 minutes with a tumbler shaker mixer, and this value is evaluated for charge stability. It was. It represents that it is excellent in charging stability, so that this value is small.
- Evaluation standard for charging stability Difference between maximum charge amount and minimum charge amount is less than -3 ⁇ C / g ⁇ : Difference between maximum charge amount and minimum charge amount is -3 ⁇ C / g or more and less than -6 ⁇ C / g ⁇ : Maximum charge The difference between the maximum charge amount and the minimum charge amount is -6 ⁇ C / g or more and less than -9 ⁇ C / g ⁇ : The difference between the maximum charge amount and the minimum charge amount is -9 ⁇ C / g or more
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Abstract
Description
・tanδ250=[250℃における損失弾性率G”]/[250℃における貯蔵弾性率G’] (1)
・tanδ100=[100℃における損失弾性率G”]/[100℃における貯蔵弾性率G’] (2)
測定機器:HAAKE RS600
測定条件:歪制御モード
昇温速度4℃/min、周波数1Hz、Strain5%、測定温度80~250℃
測定機器:セイコー電子工業株式会社製DSC220C
測定条件:10℃/min,試料:アルミ容器に試料を10mg程度入れ、ふたをする。
測定方法:DSC(示唆走査熱量分析)法
測定機器:株式会社島津製作所製CFT-500D
測定条件:昇温速度6℃/min、ノズル1.0mmΦ×10mm、荷重10kgf、試料量1.5g
ここで、軟化点(T1/2)とは高化式フローテスター〔株式会社島津製作所製CFT-500D〕においてプランジャー(ピストン)が流出開始から流出終了までの工程において中間点にきたときの温度をいう。
測定機器:トレックジャパン株式会社製 210HS-2A ブローオフ帯電量測定機器
測定条件:25℃/RH60%
測定方法:樹脂1.5gとフェライトキャリアMF-100(日本鉄粉社製)48.5gの混合物を50mlのポリ容器にて1分間、10分間、30分間、60分間ミキサーにて混合し帯電量測定機器によって測定した。
エチレングリコール512g、ネオペンチルグリコール809g、ネオデカン酸グリシジルエステル(一分子あたりのエポキシ基の平均の数:1)4g、およびクレゾールノボラック型エポキシ樹脂(一分子あたりのエポキシ基の平均の数:7.6)60gを5リットルの4つ口フラスコに入れ、加熱溶解させた後、テレフタル酸2478g、アジピン酸:77g、およびパラターシャルブチル安息香酸60gを加え、ジイソプロポキシチタン・ビスジオクチルホスフェート2gを投入し窒素気流下にて徐々に昇温させ250℃で7時間反応させて、系内がクリアであることを確認した後、更に減圧下、5時間反応させ、酸価:10、軟化点(T1/2):149℃、ガラス転移点:58℃、ゲル分率:41%のポリエステル樹脂(A-1)を得た。なお、酸価は滴定法、ガラス転移点(Tg)、軟化点(T1/2)および粘弾性値は本文記載の方法で測定した。
合成例1で用いた原料を第1表の原料および仕込み量にした以外は合成例1と同様にしてポリエステル樹脂(A2~A3)を得た。
合成例1で用いた原料を第1表の原料および仕込み量にした以外は合成例1と同様にして比較対照用ポリエステル樹脂(A’1~A’5)を得た。
ポリエステル樹脂(A-1)90部、カーボンブラックMA-11(三菱化学製)5部、ボントロンS34(オリエント化学製 帯電制御剤)1部及びカルナウバワックス4部をヘンシェルミキサ-で混合し、本発明の電子写真トナー用ポリステル樹脂組成物を得た後、2軸混練機で混練し、混練物を得た。このようにして得られた混練物をAFG100/ATP50(ホソカワミクロン社製 ジェットミル兼分級機)で微粉砕、分級した。分級後のトナーにシリカR972(日本アエロジル製)1部をヘンシェルミキサーで混合後、篩かけをして混合物を得た。得られた混合物5部とキャリア(シリコン樹脂被覆フェライトキャリア)95部を混合攪拌して電子写真用トナー(1)を調製した。電子写真用トナー(1)について、下記評価方法に従って評価した。評価結果を表に示す。
ポリエステル樹脂(A-1)の代わりに、合成例2~8で得られたポリエステル樹脂を用いる以外は、実施例1と同様にして、実施例2~3、比較例1~5の電子写真トナーを調製し、各項目について評価した。結果を表2に示す。
熱ロールの設定温度を5℃きざみに120℃から140℃まで変化させ、ベタ印刷を行った。ベタ印刷部分に堅牢度試験を行い試験前後の画像濃度をマクベス濃度計(RD-918)で測定し、その試験前の値に対する剥離後の濃度値の比率を%で表示した場合に、その値が80%以上となる温度を定着開始温度とした。この温度が低いほど低温定着性の良好な電子写真用トナーである。低温定着性の評価基準は下記の通りとした。尚、堅牢度試験は学振型摩擦堅牢度試験機(荷重:200g、擦り操作:5ストローク)を用いて行った。
◎;定着開始温度が120℃未満の場合
○;定着開始温度が120℃以上、125℃未満の場合
△;定着開始温度が125℃以上、130℃未満の場合
×;定着開始温度が130℃以上の場合
熱ロールの設定温度を5℃きざみに160℃から210℃まで変化させたときに、ベタ印刷部分が再び同じ用紙にオフセットし、目視で確認できる最低の温度で表示した。この温度が高いほど耐オフセット性が良好であることを示す。
◎;オフセット開始温度が230℃以上の場合
○;オフセット開始温度が215℃以上、230℃未満の場合
△;オフセット開始温度が190℃以上、215℃未満の場合
×;オフセット開始温度が190℃未満の場合
ただし、高温でオフセットしない場合でも、樹脂自体がワックスとして作用し印刷媒体への定着性が悪いものは×の評価とした。
ロール材質:上;ポリテトラフルオロエチレン、下;シリコーン
上ロール荷重:7Kg/350mm
ニップ幅:4mm
紙通し速度:90mm/sec
トレックジャパン株式会社製210HS-2Aブローオフ帯電量測定機器を用い、AFG100/ATP50(ホソカワミクロン社製 ジェットミル兼分級機)で微粉砕、分級したポリエステル樹脂1.5gとフェライトキャリアMF-100(日本鉄粉社製)48.5gの混合物を50mlのポリ容器にて1分間、10分間、30分間、60分間ターブラシェイカーミキサーにて混合し帯電量測定機器によって測定した。それらの平均値をとったものを帯電量とした。また、前記10分間、30分間及び60分間ターブラシェイカーミキサーにて混合し帯電量測定機器によって測定した帯電量において、最大帯電量と最小帯電量の差を求め、この値を帯電安定性の評価とした。この値が小さいほど帯電安定性に優れることを表す。
帯電量の評価基準
◎:-50μC/g以上
○:-45μC/g以上、-50μC/g未満
△:-40μC/g以上、-45μC/g未満
×:-35μC/g以上、-40μC/g未満
××:-35μC/g未満
◎:最大帯電量と最小帯電量の差が-3μC/g未満
○:最大帯電量と最小帯電量の差が-3μC/g以上、-6μC/g未満
△:最大帯電量と最小帯電量の差が-6μC/g以上、-9μC/g未満
×:最大帯電量と最小帯電量の差が-9μC/g以上
Claims (11)
- 一塩基酸(a1)、多塩基酸(a2)、多価アルコール(a3)、モノエポキシ化合物(a4)、及び4個以上のエポキシ基を有するポリエポキシ化合物(a5)と、を反応して得られるポリエステル樹脂(A)を含有することを特徴とする電子写真トナー用ポリエステル樹脂組成物。
- 前記一塩基酸(a1)が芳香族モノカルボン酸である請求項1記載の電子写真トナー用ポリエステル樹脂組成物。
- 前記芳香族モノカルボン酸が、安息香酸又はp-置換安息香酸である請求項2記載の電子写真トナー用ポリエステル樹脂組成物。
- 前記ポリエステル樹脂(A)のゲル分率が10~70質量%の範囲である請求項1~3の何れか1項記載の電子写真トナー用ポリエステル樹脂組成物。
- 前記ポリエステル樹脂(A)の粘弾性測定結果において、
下記式(1)
tanδ250=[250℃における損失弾性率G”]/[250℃における貯蔵弾性率G’] (1)
で表される250℃におけるtanδ値(tanδ250)と、
下記式(2)
tanδ100=[100℃における損失弾性率G”]/[100℃における貯蔵弾性率G’] (2)
で表される100℃におけるtanδ値(tanδ100)
との差〔tanδ250-tanδ100〕が1.00以下である請求項1~4の何れか1項記載の電子写真トナー用ポリエステル樹脂組成物。 - 前記一塩基酸(a1)と前記多塩基酸(a2)との使用割合(a1)/(a2)が1/99~30/70(質量比)である請求項1~5の何れか1項記載の電子写真トナー用ポリエステル樹脂組成物。
- 前記4個以上のエポキシ基を有するポリエポキシ化合物(a5)が、4~10個のエポキシ基を有するノボラック型エポキシ樹脂である請求項1~6の何れか1項記載の電子写真トナー用ポリエステル樹脂組成物。
- 前記モノエポキシ化合物(a4)と4個以上のエポキシ基を有するポリエポキシ化合物(a5)の合計質量が、全仕込み原料の総質量に対して0.5~10質量%の範囲である請求項1~7の何れか1項記載の電子写真トナー用ポリエステル樹脂組成物。
- 前記一塩基酸(a1)に対し、モノエポキシ化合物(a4)及び4個以上のエポキシ基を有するポリエポキシ化合物(a5)の合計質量の比〔a1/[a4+a5]〕が3/97~70/30の範囲である請求項1~8の何れか1項記載の電子写真トナー用ポリエステル樹脂組成物。
- 前記ポリエステル樹脂(A)が、原料である一塩基酸(a1)、多塩基酸(a2)、多価アルコール(a3)、モノエポキシ化合物(a4)、及び4個以上のエポキシ基を有するポリエポキシ化合物(a5)を溶解混合した後、ここにエステル化触媒を加えてから昇温して反応させて得られるものである請求項1~9の何れか1項記載の電子写真トナー用ポリエステル樹脂組成物。
- 請求項1~10の何れか1項記載の電子写真トナー用ポリエステル樹脂組成物を含有することを特徴とする電子写真トナー。
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