WO2008111726A1 - Polyester resin composition for toner and toner containing the same - Google Patents
Polyester resin composition for toner and toner containing the same Download PDFInfo
- Publication number
- WO2008111726A1 WO2008111726A1 PCT/KR2008/000312 KR2008000312W WO2008111726A1 WO 2008111726 A1 WO2008111726 A1 WO 2008111726A1 KR 2008000312 W KR2008000312 W KR 2008000312W WO 2008111726 A1 WO2008111726 A1 WO 2008111726A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- toner
- resin composition
- polyester
- end group
- polyester resin
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 229920001225 polyester resin Polymers 0.000 title claims abstract description 17
- 239000004645 polyester resin Substances 0.000 title claims abstract description 17
- 229920000728 polyester Polymers 0.000 claims abstract description 18
- 229920001634 Copolyester Polymers 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 7
- YXTFRJVQOWZDPP-UHFFFAOYSA-M sodium;3,5-dicarboxybenzenesulfonate Chemical compound [Na+].OC(=O)C1=CC(C(O)=O)=CC(S([O-])(=O)=O)=C1 YXTFRJVQOWZDPP-UHFFFAOYSA-M 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000007259 addition reaction Methods 0.000 claims abstract description 5
- 230000009477 glass transition Effects 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011342 resin composition Substances 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 6
- 239000011230 binding agent Substances 0.000 abstract description 6
- 239000006185 dispersion Substances 0.000 description 11
- 239000002245 particle Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- -1 aliphatic diols Chemical class 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000654 additive Substances 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
- 230000004931 aggregating effect Effects 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010438 heat treatment Methods 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
- 238000005259 measurement Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000010309 melting process Methods 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
- 239000000049 pigment Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- VNGLVZLEUDIDQH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;2-methyloxirane Chemical class CC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 VNGLVZLEUDIDQH-UHFFFAOYSA-N 0.000 description 1
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical class C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KWORKYDIARWARF-UHFFFAOYSA-N N-(4-chloro-2-methylphenyl)-4-[(4-chloro-2-methylphenyl)diazenyl]-3-hydroxynaphthalene-2-carboxamide Chemical compound Cc1cc(Cl)ccc1NC(=O)c1cc2ccccc2c(N=Nc2ccc(Cl)cc2C)c1O KWORKYDIARWARF-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 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
- C08G63/66—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
-
- 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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—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
- G03G9/0802—Preparation methods
- G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
-
- 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
- G03G9/08771—Polymers having sulfur in the main chain, with or without oxygen, nitrogen or carbon only
-
- 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
- G03G9/08791—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by the presence of specified groups or side chains
-
- 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
- polyester resin Due to svch requirements for toner, polyester resin has been used as a binder for full- color toner, because it has excellent low-temperature fixing properties and excellent transparency. However, the resolution of images for full-color applications has been further required.
- the present invention provides a polyester resin composition for toner, which is obtained by adding a compound, which can undergo an addition reaction with the OH end group and COOH end group of polyester, to a straight-chain copolyester comprising a divalent alcohol component, containing a bisphenol A alkylene oxide adduct, and a dibasic acid component, containing sodium 5-sulfoisophthalate, and allowing the mixture to react, as well as a toner containing the polyester resin composition.
- a polyester resin composition for toner which is obtained by adding a compound, which can undergo an addition reaction with the OH end group and COOH end group of polyester, to a straight-chain copolyester comprising a divalent alcohol component, containing a bisphenol A alkylene oxide adduct, and a dibasic acid component, containing sodium 5-sulfoisophthalate, and allowing the mixture to react, as well as a toner containing the polyester resin composition.
- divalent alcohol component examples include aliphatic diols, such as ethyleneglycol, 1,2-propanediol, 1,4-butanediol and neopentylglycol, and aromatic diols, sirh as bisphenol A propylene oxide adducts and bisphenol A ethylene oxide adducts.
- dibasic acid component examples include, in addition to sodium 5-sulfoisophthalate as an essential component, aromatic di- carboxylic acids, such as terephthalic acid, isophthalic acid and phthalic acid, and aliphatic dicarboxylic acids, such as adipic acid and surinic acid.
- aromatic di- carboxylic acids such as terephthalic acid, isophthalic acid and phthalic acid
- aliphatic dicarboxylic acids such as adipic acid and surinic acid.
- these dibasic acids are used in the form of glycolester or lower alkylester.
- the polyester resin composition of the present invention should be used for the preparation of toner without any melting process in order to maintain the excellent melting behavior thereof.
- the polyester resin composition is applied in a method of preparing toner by an energy aggregation process.
- the polyester resin composition is dispersed in dilute ammonia water to make an emulsion.
- wax, a pigment, a charge-controlling agent, etc. are added, and the mixture is mixed with an aggregating agent at high speed to obtain microspherical toner particles.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Disclosed herein are a binder resin composition for toner, which can provide a toner having excellent sharp melt properties and low-temperature fixing properties, and a toner containing the binder resin composition. The polyester resin composition for toner is obtained by obtained by adding a compound, which can undergo an addition reaction with the OH end group and COOH end group of polyester, to a straight-chain copolyester comprising a divalent alcohol component, containing a bisphenol A alkylene oxide adduct, and a dibasic acid component, containing sodium 5-sulfoisophthalate, and allowing the mixture to react.
Description
Description
POLYESTER RESIN COMPOSITION FOR TONER AND TONER CONTAINING THE SAME
Technical Field
[1] The present invention relates to a resin composition, which is used in developing toners in electrophotographic devices, such as photocopiers, printers and facsimiles, which employ electrophotographic processes, and to a toner containing the resin composition. Background Art
[2] In methods for obtaining images by electrophotographic printing processes and electrostatic charge development processes, an electrostatic charge image formed on a pho- tocondvctor is developed with a toner previously charged by friction, followed by fixation. Meanwhile, as the high-speed and energy-saving trends of electrophotographic devices progress, it is required to fix toner images in a shorter time at a lower temperature. Also, due to the recent diffusion of full-color electrophotographic systems, a toner that forms more clear and brilliant images is required.
[3] Due to svch requirements for toner, polyester resin has been used as a binder for full- color toner, because it has excellent low-temperature fixing properties and excellent transparency. However, the resolution of images for full-color applications has been further required.
[4] Meanwhile, for high-speed fixation, it has been required that binder resin melts as soon as possible (sharp melt property). Polyester resin is prepared by the melt poly condensation of dibasic acid with divalent alcohol, and for this reason, the molecular weight of the polymer has specific distribution ( most reliable distribution ), and thus the softening point (SP) thereof also has distribution. For this reason, the sharp melt property of the polyester resin has been problematic.
[5] Patent Documents 1 and 2 disclose polyester resins, comprising bisphenol A alkylene oxide and sodium 5-sulfoisophthalate. However, such polymers still have a problem in terms of sharp melt properties. Patent Document 1: Japanese Patent Laid-Open Publication No. Hei 4-86744; and Patent Document: Japanese Patent Laid-Open Publication No. 2007-4Q33> Disclosure of Invention Technical Problem
[6] It is an object of the present invention to provide a binder resin composition for toner, which can provide a toner having excellent sharp melting properties and low- temperature fixing properties, and a toner containing the binder resin composition. Technical Solution
[7] To achieve the above object, the present invention provides a polyester resin composition for toner, which is obtained by adding a compound, which can undergo an addition reaction with the OH end group and COOH end group of polyester, to a straight-chain copolyester comprising a divalent alcohol component, containing a bisphenol A alkylene oxide adduct, and a dibasic acid component, containing sodium 5-sulfoisophthalate, and allowing the mixture to react, as well as a toner containing the polyester resin composition. Mode for the Invention
[8] Hereinafter, preferred embodiments of the present invention will be described.
However, it is to be understood, however, that these embodiments are illustrative only and the scope of the present invention are not limited thereto.
[9] Examples of the divalent alcohol component that is used in the present invention include aliphatic diols, such as ethyleneglycol, 1,2-propanediol, 1,4-butanediol and neopentylglycol, and aromatic diols, sirh as bisphenol A propylene oxide adducts and bisphenol A ethylene oxide adducts.
[10] Examples of the dibasic acid component that is used in the present invention include, in addition to sodium 5-sulfoisophthalate as an essential component, aromatic di- carboxylic acids, such as terephthalic acid, isophthalic acid and phthalic acid, and aliphatic dicarboxylic acids, such as adipic acid and surinic acid. For polyester polymerization, these dibasic acids are used in the form of glycolester or lower alkylester.
[11] Catalysts for use in the synthesis of the straight-chain copolyester include conventional catalysts for polyester polymerization, such as titanium tetraalkoxide, aluminum chelate compounds, antimony trioxide, germanium oxide, and calcium acetate. As anti-colorants, those conventionally used in polyester polymerization, for example, phosphorous acid and triphenyl phosphate, are used.
[12] The use of the combination of diol and dicarboxylic acid can provide a polyester, which contains sodium 5-sulfoisophthalate and has a glass transition temperature (Tg) of 50-70 0C and a softening temperature (SP) higher than 90-140 0C.
[13] The straight-chain copolyester of the present invention is synthesized in the same manner as conventional polyesters. Specifically, esterification or transesterification is
conducted at a temperature of 100-220 0C. Then, the reaction temperature is increased to about 290 0C and the reaction pressure is lowered to about 1 mmHg, and in such conditions, polymerization is conducted while glycols generated are distilled. After a given degree of polymerization is reached, the vacuum pressure of the reaction system is returned to atmospheric pressure.
[14] The compound capable of addition-reacting with the OH end group and COOH end group of polyester is added to and mixed with the straight-chain copolyester returned to atmospheric pressure, and the mixture is stirred. As the compound capable of addition-reacting with the OH end group and COOH end group of polyester, an oxazoline-containing polymer or polycarboxyimide is used. A polyester molecule having a lower molecular weight has a larger number of end groups, and the addition reaction between the end groups thereof and the above compound occurs faster. As a result, the specific molecular weight distribution (so called most reliable distribution) of polyester is greatly changed, resulting in a polyester having a sharper molecular weight distribution and a sharper melting behavior. The sharper molecular weight distribution and sharper melting behavior of the polyester are maintained without change as long as the polyester is not subsequently subjected to a melting process.
[15] The polyester resin composition of the present invention should be used for the preparation of toner without any melting process in order to maintain the excellent melting behavior thereof. Preferably, the polyester resin composition is applied in a method of preparing toner by an energy aggregation process. Specifically, the polyester resin composition is dispersed in dilute ammonia water to make an emulsion. To the emulsion, wax, a pigment, a charge-controlling agent, etc., are added, and the mixture is mixed with an aggregating agent at high speed to obtain microspherical toner particles.
[16] Examples
[17] Hereinafter, the present invention will be described in further detail with reference to examples. Also, the evaluation of performance in examples and comparative examples was performed in the following manner.
[18] Glass transition temperature (Tg)
[19] The intersection between the baseline of a chart and the tangent line of an en- dothermic curve around glass transition temperature, as measured using differential scanning calorimeter DSC-60 (manufactured by Shimadzu, Japan) at a heating rate of 5 °C/min, was taken as glass transition temperature (Tg).
[20] Softening point (SP)
[21] Softening point was determined by measuring the temperature at which 1/2 of 1.0 g of a sample flowed out, at a load of 294N (30kgf) and a constant heating rate of 3 °C/min using a 1 mmΦ x 10 mm nozzle and the flow tester CFT-500 (manufactured by Shimadzu, Japan).
[22] The difference between the flow-out initiation temperature (T1) and flow-out termination temperature (T2) of the sample, that is, ΔT = T2- T1, was used as a measure of sharp melt properties.
[23] Number-average molecular weight (Mn) and weight-average molecular weight (Mw)
[24] HLC- 802A (manufactured by Toyo Soda, Japan);
[25] Column: two TSK GEL GMH6 columns (manufactured by Toyo Soda, Japan);
[26] Measurement temperature: 25 0C;
[27] Sample solution: Q5wt% THF solution;
[28] Amount of solution injected: 200 micro-cc;
[29] Detector: refractive index detector.
[30] Low-temperature fixing property of toner
[31] Printing was conducted using a printer (SPEEDIA N4-614 manufactured by Casio,
Japan) with a fixing roller not applied with silicone oil, at a roller speed of 100 mm/ sec. The lowest temperature at which toner started to be fixed to paper was taken as fixing temperature, and measurement and evaluation were performed according to the following criteria:
[32] © (very good): a fixing temperature lower than 120 0C;
[33] O (good): a fixing temperature of 120-130 0C;
[34] Δ (usable) : a fixing temperature of 130- 160 0C;
[35] X (bad): a fixing temperature higher than 16O0C.
[36] Examples of preparing resins are shown in Table 1 below.
[37] [Table 1]
[38]
[39]
[40] Herein, SIPM means 5-sodium sulfodimethyl isophthalate. [41] Table 2 below shows Examples in which a compound capable of addition-reacting with the OH end group and COOH end group of polyester was added to and allowed to react with the prepared resin.
[42] [Table 2] [43]
[44] Herein, additive A indicates HMV- 8CA (manufactured by Nisshinbo, Japan), and additive B indicates EPOCROS RPS- 105 (manufactured by Nippon Shokubai). [45] Toners were prepared using the resin compositions of Table 2, and the evaluation results thereof are shown in Table 3 below.
[46] [Table 3] [47]
[48] The preparation of the toners was performed in the following manner.
[49] 1000 cc (Q3%) of dilute ammonia water was placed in a diffuser, and 300 g of a molten polyester resin compositions was added slowly thereto over 20 minutes while the liquid was maintained at 80 0C with intensive stirring. Also, the mixture continued to be stirred for 10 minutes, thus obtaining a white polyester resin emulsion. A portion of the emulsion was filtered and dried. The resulting dispersion had a particle diameter of about 200 μm as observed with a microscope. (Polyester dispersion A).
[50] 50 g of polypropylene wax (Biscol 660P, manufactured by Sanyo Chemical Industry
Co., Ltd., Japan), 5 g of an anionic surfactant (Neogen RK, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) and 200 g of ion-exchanged water were placed in a diffuser, in which they were mixed at 80 0C for 10 minutes. A portion of the mixture was filtered and dried. The resulting dispersion had a particle diameter of about 05 μm as measured with a microscope. (Wax dispersion B).
[51] 100 g of Permanent Carmine 3810 (red, manufactured by Sanyo Color Works, Ltd.,
Japan), 15 g of an anionic surfactant (Neogen RK, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) and 900 g of ion-exchanged water were placed in a diffuser, in which they were mixed 80 0C for 10 minutes. A portion of the mixture was filtered and dried. The resulting dispersion had a particle diameter of about 05 μm as measured with a microscope. (Pigment dispersion C).
[52] 560 g of the dispersion A, 50 g of the dispersion B, 25 g of the dispersion C and 05 g of a non-ionic surfactant (Igepal CA897) were stirred in a stirrer (Ultraturrax, 8000 rpm) under high shear conditions for 30 minutes. Then, Q 13 g of an aggregating agent (polyaluminium chloride, 10% nitrate) was added thereto. The pH of the mixture was adjusted to 4.2-4.5 by the addition of Q3N nitric acid and IN caustic soda. The
mixture was transferred into a polymerization reactor, in which polymer particles were aggregated and prepared. The particles had a diameter of about 5 μm as observed with a microscope.
[53] Then, 220 g of the dispersion A was added slowly thereto at 50 0C. After the mixture was stirred for 6 hours at a pH of 9.0, it was returned to a pH of 65 and room temperature, and then filtered and dried. The resulting dispersion had a particle diameter of about 6 μm as observed with a microscope.
[54] Also, 100 g of the red-color toner particles were immersed in water (50 0C and pH
4.0) containing 2 g of a cation dye (Cation Red 7BNH 200%) dissolved therein, followed by stirring for 10 minutes.
[55] Although the preferred embodiment of the present invention has been described for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims. Industrial Applicability
[56] As described above, the use of the polyester resin composition for toner according to the present invention can provide a toner having excellent sharp melt properties and low-temperature fixing properties.
Claims
[1] A polyester resin composition for toner, which is obtained by adding a compound, which can undergo an addition reaction with the OH end group and COOH end group of polyester, to a straight-chain copolyester comprising a divalent alcohol component, containing a bisphenol A alkylene oxide addvct, and a dibasic add component, containing sodium 5-sulfoisophthalate, and allowing the mixture to react.
[2] The composition of Claim 1, wherein the amount of the bisphenol A alkylene oxide adduct in the divalent alcohol component of the copolyester is 10-80 mol%.
[3] The composition of Claim 1, wherein the amount of the sodium
5-sulfoisophthalate in the dibasic add component of the copolyester is 1-10 mol%.
[4] The composition of Claim 1, wherein the straight-chain copolyester has a glass transition temperature (Tg) of 50-70 0C and a softening point (SP) of 90-140 0C.
[5] The composition of Claim 1, wherein the compound, which can undergo an addition reaction with the OH end group and COOH end group of polyester, is an oxazoline -containing polymer or polycarboxyimide.
[6] A toner containing a polyester resin composition as set forth in Claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020070024033A KR20080083452A (en) | 2007-03-12 | 2007-03-12 | Polyester resin composition for toner and the toner thereof |
| KR10-2007-0024033 | 2007-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2008111726A1 true WO2008111726A1 (en) | 2008-09-18 |
Family
ID=39759648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2008/000312 WO2008111726A1 (en) | 2007-03-12 | 2008-01-18 | Polyester resin composition for toner and toner containing the same |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR20080083452A (en) |
| WO (1) | WO2008111726A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2365393A1 (en) * | 2010-03-10 | 2011-09-14 | Ricoh Company, Ltd. | Toner and developer |
| US10088767B2 (en) * | 2016-05-12 | 2018-10-02 | Kyocera Document Solutions Inc. | Electrostatic latent image developing toner |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6028584B2 (en) * | 2013-01-17 | 2016-11-16 | Dic株式会社 | Method for producing toner for developing electrostatic image |
| KR101685547B1 (en) | 2015-02-04 | 2016-12-12 | (주) 파워텍 | Polyester resin composition for toner binder, and method of preparing the same |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0486744A (en) * | 1990-07-30 | 1992-03-19 | Toyobo Co Ltd | Electrophotographic toner |
| JPH04273255A (en) * | 1991-02-28 | 1992-09-29 | Dainippon Ink & Chem Inc | Electrostatic charge image developing toner |
| US6054242A (en) * | 1998-07-16 | 2000-04-25 | Tomogawa Paper Co., Ltd. | Electrophotographic toner |
| US6544710B2 (en) * | 1998-12-23 | 2003-04-08 | Lexmark International, Inc. | Reactive compatibilization of polymeric components such as siloxane polymers with toner resins |
| KR20050095504A (en) * | 2004-03-26 | 2005-09-29 | 김효성 | Highly functional resin recycled polyester and polyamide hybrid waste and its manufacturing method |
| JP2007004033A (en) * | 2005-06-27 | 2007-01-11 | Fuji Xerox Co Ltd | Toner for electrostatic image development, method for manufacturing same, electrostatic image developer, and image forming method |
-
2007
- 2007-03-12 KR KR1020070024033A patent/KR20080083452A/en not_active Application Discontinuation
-
2008
- 2008-01-18 WO PCT/KR2008/000312 patent/WO2008111726A1/en active Application Filing
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0486744A (en) * | 1990-07-30 | 1992-03-19 | Toyobo Co Ltd | Electrophotographic toner |
| JPH04273255A (en) * | 1991-02-28 | 1992-09-29 | Dainippon Ink & Chem Inc | Electrostatic charge image developing toner |
| US6054242A (en) * | 1998-07-16 | 2000-04-25 | Tomogawa Paper Co., Ltd. | Electrophotographic toner |
| US6544710B2 (en) * | 1998-12-23 | 2003-04-08 | Lexmark International, Inc. | Reactive compatibilization of polymeric components such as siloxane polymers with toner resins |
| KR20050095504A (en) * | 2004-03-26 | 2005-09-29 | 김효성 | Highly functional resin recycled polyester and polyamide hybrid waste and its manufacturing method |
| JP2007004033A (en) * | 2005-06-27 | 2007-01-11 | Fuji Xerox Co Ltd | Toner for electrostatic image development, method for manufacturing same, electrostatic image developer, and image forming method |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2365393A1 (en) * | 2010-03-10 | 2011-09-14 | Ricoh Company, Ltd. | Toner and developer |
| CN102193355A (en) * | 2010-03-10 | 2011-09-21 | 株式会社理光 | Toner and developer |
| CN102193355B (en) * | 2010-03-10 | 2013-05-01 | 株式会社理光 | Toner and developer |
| US10088767B2 (en) * | 2016-05-12 | 2018-10-02 | Kyocera Document Solutions Inc. | Electrostatic latent image developing toner |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20080083452A (en) | 2008-09-18 |
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