KR101160237B1 - Polyester resin for toner binder and method for preparing the same, and toner comprising the same - Google Patents

Abstract

The present invention relates to a polyester resin for a toner binder, a method of manufacturing the same, and a toner including the same, and more particularly, to include isosorbide and aromatic diol in an appropriate amount in a reactant, and to control the pressure reduction conditions during the polycondensation reaction. And, by specifying the glass transition temperature, number average molecular weight and softening temperature of the polyester resin to be produced in an appropriate range, a polyester resin for toner binder, which can ensure excellent durability and low temperature fixability, a manufacturing method and the same It relates to toner.

Description

Polyester resin for toner binder, manufacturing method thereof, and toner comprising the same {POLYESTER RESIN FOR TONER BINDER AND METHOD FOR PREPARING THE SAME, AND TONER COMPRISING THE SAME}

The present invention relates to a polyester resin for a toner binder, a method of manufacturing the same, and a toner including the same, and more particularly, to include isosorbide and aromatic diol in an appropriate amount in a reactant, and to control the pressure reduction conditions during the polycondensation reaction. And, by specifying the glass transition temperature, number average molecular weight and softening temperature of the polyester resin to be produced in an appropriate range, a polyester resin for toner binder, which can ensure excellent durability and low temperature fixability, a manufacturing method and the same It relates to toner.

In recent years, developing toners capable of providing high-speed and high-quality images in image forming apparatuses such as laser printers, facsimile machines, and copiers have attracted attention. Among various methods for fixing the toner image to the sheet at high speed and high quality, the most commonly used one is the hot pressing method. The hot pressing method has an advantage of fast and accurate fixing of an image because the heating roller directly presses the toner to contact it, and the binder resin included in the toner fixes the image to a sheet such as paper in the hot pressing method. do. Conventionally, styrene / acrylic copolymers were mainly used as binders for forming high speed and high quality images, but polyester resins are frequently used.

The performance required as a binder importantly includes blocking resistance, fixability, and charging characteristics affecting image formation, etc., related to durability in toner storage. Among them, in terms of blocking resistance, even when the toner is stored at a high temperature, it is required that the toner does not block and have a relatively high glass transition temperature as a binder. Low temperature fixability, which is a performance of fixing to a film, is required.

Various methods have been proposed to achieve this performance required as a binder. In particular, a method of improving low temperature fixability of a toner has been proposed by using a polyester resin having a low softening temperature (also called a softening point) as a binder to form a high speed image. However, when the molecular weight is lowered to prepare a polyester resin having a lower softening temperature, the glass resin has a sharply lowered glass transition temperature due to the low molecular weight, which causes a significant decrease in durability such as an offset during long-term use. there is a problem.

On the other hand, as a method of improving the blocking resistance for improving durability, a method of using a single functional isocyanate (Japanese Patent Laid-Open No. 2000-275902) and a method of using a single functional amine (Japanese Patent Laid-Open No. Hei 11-92533) has been proposed. However, the polyester resins produced by these methods increase the molecular weight by increasing the molecular weight due to the crosslinking composition in the polyester, but the fixing of the toner is deteriorated, so that when the toner is manufactured in this way, the high speed printing and the high speed fixing Problems occur with image quality.

Japanese Laid-Open Patent Publication 2000-275902 Japanese Laid-Open Patent Publication No. 11-92533

The present invention has been made to solve the problems of the prior art as described above, to provide a polyester resin for a toner binder, a method of manufacturing the same and a toner including the same which can ensure excellent durability and low temperature fixability at the same time Shall be.

In order to achieve the above technical problem, the present invention is a reaction comprising 100 molar equivalents of aromatic divalent acid, 5 to 30 molar equivalents of isosorbide, 10 to 50 molar equivalents of aliphatic diol and 30 to 70 molar equivalents of aromatic diol The mixture is prepared by polycondensation reaction, and has a glass transition temperature of 60 to 80 ° C., a number average molecular weight of 2500 to 5500 g / mol, and a softening temperature of 95 to 115 ° C. to provide a polyester resin for a toner binder.

In another aspect of the present invention, there is also provided a reaction mixture comprising, in relative content, 100 molar equivalents of aromatic divalent acid, 5-30 molar equivalents of isosorbide, 10-50 molar equivalents of aliphatic diol, and 30-70 molar equivalents of aromatic diol. It includes the step of polycondensation reaction, and provides a polyester resin manufacturing method for a toner binder, characterized in that the reaction pressure during the polycondensation reaction is reduced at a rate of 4 to 8mmHg per minute to a final vacuum pressure of 40 to 50mmHg.

In addition, another aspect of the present invention provides a toner comprising the polyester resin as a binder.

The polyester resin for toner binder of the present invention can secure excellent durability, low temperature fixability and offset characteristics at the same time, and can be usefully used as a toner binder of a laser printer or a copier for high speed and high quality images.

Hereinafter, the present invention will be described in detail.

The polyester resin for toner binder of the present invention is a polyester resin prepared by polycondensation of a reaction mixture containing an aromatic divalent acid, isosorbide, aliphatic diol and aromatic diol, wherein the reaction mixture is relative The content includes 100 molar equivalents of aromatic divalent acid, 5-30 molar equivalents of isosorbide, 10-50 molar equivalents of aliphatic diol and 30-70 molar equivalents of aromatic diol, and has a glass transition temperature (Tg) of 60-80 ° C. The number average molecular weight (Mn) is 2500 to 5500 g / mol, and the softening temperature is 95 to 115 ° C.

In general, the following method is mainly used to improve the durability of the polyester resin for toner binder.

1) Use of aromatic monomer

2) increase molecular weight

3) Use of cross link agent

However, since the method of 1) requires the use of an aromatic monomer having low reactivity, low molecular weights required for low temperature fixing due to low reaction rate have a disadvantage in that the glass transition temperature is improved and durability is lowered. In addition, the method of 2) increases the molecular weight of the resin by increasing the reaction rate, but the glass transition temperature is partially increased, but the effect of improving the durability is insignificant above a certain level of molecular weight, and the high molecular weight tends to adversely affect the low temperature fixability. . On the other hand, the method of 3) has improved durability through the cross-linked structure formed by the additional new monomer, but there is a fear that the low temperature fixability is limited and adversely affect other physical properties such as charging characteristics.

Therefore, in the present invention, instead of the above method, an aromatic divalent acid is used as an acid component, and an aliphatic diol, an aromatic diol, and an isosorbide are used as a diol component in a specific content range. Provided is a polyester resin for a toner binder having excellent durability and low temperature fixing property by controlling polymerization conditions such as pneumatic pressure, polymerization temperature and catalyst amount. Hereinafter, the present invention will be described by dividing the reactant for polycondensation, the production of a polyester resin, and the physical properties of the produced polyester resin.

[ Polycondensation  Reactant]

Aromatic divalent acid

The aromatic divalent acid contained in the polycondensation reactant is a component that increases the glass transition temperature of the polyester resin and contributes to the improvement of durability.

The aromatic divalent acid is one selected from the group consisting of terephthalic acid, isophthalic acid, dimethyl terephthalate, dimethyl isophthalate, diethyl terephthalate, diethyl isophthalate, dibutyl terephthalate, dibutyl isophthalate and acid anhydrides thereof. Although the above can be used, it is not necessarily limited thereto.

Isosorbide ( isosorbide )

Isosorbide contained in the polycondensation reactant is a component that can ensure high glass transition temperature and durability while lowering the molecular weight of the polyester resin.

In the present invention, isosorbide is used in an amount of 5 to 30 molar equivalents based on 100 molar equivalents of aromatic divalent acid. If the content is less than 5 molar equivalents, the glass transition temperature of the polyester resin to be produced is lowered and the durability improvement effect is insignificant. If it exceeds 30 molar equivalents, the durability is improved by increasing the glass transition temperature of the polyester resin produced but isosorbide Due to its thermal stability, the softening temperature of the polyester resin produced is high, thereby lowering the low temperature fixability.

Aliphatic Dior

Aliphatic diols contained in the polycondensation reactant are components that increase the reactivity and facilitate molecular weight control.

Aliphatic diols include ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, 1,4-butanediol, 1,4-butenediol, neopentin glycol, 2,3-butanediol, 1,5-pentane Diol, 2,3-pentanediol, 1,6-hexanediol, 2,3-hexanediol, 3,4-hexanediol, 1,7-heptanediol, dodecanediol, 1,4-cyclohexane dimethanol, One or more selected from the group consisting of 1,4-cyclohexanediol and neopentyl glycol may be used, but is not necessarily limited thereto.

The content of aliphatic diol is 10 to 50 molar equivalents relative to 100 molar equivalents of aromatic divalent acid. If the content is less than 10 molar equivalents may cause a decrease in reaction rate, and if the content exceeds 50 molar equivalents, the glass transition temperature is lowered, thereby lowering thermal stability and durability.

Aromatic Dior

Aromatic diols contained in the polycondensation reactants are durable and low temperature fixability of the polyester resin. It is an ingredient that contributes to improvement.

Aromatic diols include polyoxyethylene- (2,0) -2,2-bis (4-hydroxyphenyl) propane, including bisphenol A derivatives (e.g., bisphenol A derivatives added with ethylene oxide and propylene oxide), Polyoxypropylene- (2,0) -2,2-bis (4-hydroxyphenyl) propane, polyoxypropylene- (2,2) -polyoxyethylene- (2,0) -2,2-bis ( 4-hydroxyphenyl) propane, polyoxyethylene- (2,3) -2,2-bis (4-hydroxyphenyl) propane, polyoxypropylene- (6) -2,2-bis (4-hydroxy Phenyl) propane, polyoxypropylene- (2,3) -2,2-bis (4-hydroxyphenyl) propane, polyoxypropylene- (2,4) -2,2-bis (4-hydroxyphenyl) Propane, polyoxypropylene- (3,3) -3,3-bis (4-hydroxyphenyl) propane, polyoxyethylene- (3,0) -2,2-bis (4-hydroxyphenyl) propane and One selected from the group consisting of polyoxyethylene- (6) -2,2-bis (4-hydroxyphenyl) propane But can use the image, it is not limited thereto.

In the present invention, the aromatic diol is used in an amount of 30 to 70 molar equivalents based on 100 molar equivalents of aromatic divalent acid. If the content is less than 30 molar equivalents, the reaction rate is increased, but the thermal stability, storage stability and low temperature fixability are lowered, and if it exceeds 70 molar equivalents, the reaction rate is significantly reduced.

In addition to the above components, the polycondensation reactant may further include a trivalent or higher polyhydric alcohol, a trivalent or higher polyhydric acid, or a mixture thereof as necessary. Trivalent or higher polyhydric alcohols and polyhydric acids are components that contribute to improving the glass transition temperature, thermal stability, durability and low temperature fixability of the polyester resin produced.

The trihydric or higher polyhydric alcohols include trimethylolethane, trimethylolpropane, 2-methylpropanetriol, glycerol, 1,2,5-pentanetriol, 1,2,4-butanetriol, pentaerytriol, di Pentaerythritol, tripentaerythritol, sorbitol, 2-hydroxymethylpropane-1,3-diol, 2-methyl-1,2,4-butanetriol, 1,3,5-trihydroxymethylbenzene, 1,2,3,6-hexanetetrol, 1,4-sorbitan and the like may be used alone or in combination of two or more, but is not necessarily limited thereto. Examples of the trivalent or higher polyvalent acid include trimellitic acid, pyromellitic acid, 1,2,4-cyclohexane tricarboxylic acid, benzophenone tetracarboxylic acid, 2,5,7-naphthalene tricarboxylic acid, 1,2 , 4-naphthalenetricarboxylic acid, 1,2,4-butanetricarboxylic acid, 1,2,5-hexanetricarboxylic acid, 1,3-dicarboxy-2-methyl-2-methylenecarboxypropane Or the like may be used alone or in combination of two or more, but is not necessarily limited thereto.

The preferred content of the trivalent or higher polyhydric alcohol is 0.1 to 20 molar equivalents relative to 100 molar equivalents of the aromatic divalent acid, and the preferred content of the trivalent or higher polyhydric acid is 0.1 to 20 molar equivalents relative to 100 molar equivalents of the total diol. If the content of the trivalent or higher polyhydric alcohol and polyhydric acid is less than the above preferred lower limit, it may be difficult to expect the effect of improving the thermal stability and durability according to the addition of the present component, and if it exceeds the above preferred upper limit, the gelation of the resin is promoted to obtain a polymerized product. It is difficult and fixability can be reduced.

In one embodiment, 100 molar equivalents of aromatic divalent acid, 5-30 molar equivalents of isosorbide, 10-50 molar equivalents of aliphatic diol, 30-70 molar equivalents of aromatic diol, 0.1-20 molar equivalents of trivalent or more polyhydric alcohol, and ( A polycondensation reaction mixture containing 0.1 to 20 molar equivalents of trivalent or more polyvalent acid can be used with respect to 100 molar equivalents of total diol.

[Production of Polyester Resin]

Manufacture overview

The polyester resin for toner binder according to the present invention comprises 100 molar equivalents of aromatic divalent acid, 5 to 30 molar equivalents of isosorbide, 10 to 50 molar equivalents of aliphatic diol, 30 to 70 molar equivalents of aromatic diol, and optional components under a suitable catalyst. It is prepared by esterification and polycondensation of a trivalent or higher polyhydric alcohol and / or polyhydric acid.

Polycondensation  catalyst

As the polycondensation catalyst used in the production of the present invention, a titanium-based catalyst, a zinc-based acetate catalyst or a mixed catalyst thereof may be used. The polycondensation catalyst is preferably added at a concentration of 500 to 1100 ppm based on the total acid content. If the catalyst concentration is less than 500ppm, the polyester resin may not be polymerized to the desired molecular weight. If the catalyst concentration is higher than 1100ppm, the catalyst precipitates as a precipitate, thereby reducing the polymerization reaction rate and lowering the transparency of the polyester resin. Becomes difficult, gelation is promoted, and fixability can be reduced.

Polymerization conditions

In order to prepare a polyester resin for toner binder having excellent durability and low temperature fixing property of the present invention, the above polycondensation reaction product is first esterified in the presence of an esterification catalyst to obtain a prepolymer, and then the polycondensation reaction is performed. In one embodiment, the reaction temperature of the esterification reaction is maintained at 200 to 220 ° C. for about 2 hours, the resulting by-products are removed while maintaining at 220 to 230 ° C. for about 1 hour, and then the polycondensation reaction is performed. The reaction temperature in the polycondensation reaction is preferably maintained at 230 to 250 ℃ until the reactant reaches the desired viscosity. If the reaction temperature is maintained below 230 ℃, the reaction time is long, the degree of polymerization is lowered, the durability may be lowered. If the reaction temperature is maintained above 250 ℃, the reaction proceeds rapidly, difficult to control and promotes gelation to improve low temperature fixability It may be difficult to form low molecular weight.

In the present invention, the reaction pressure during the polycondensation reaction is reduced to a final vacuum pressure, preferably at a rate of 4 to 8 mmHg per minute, more preferably at a rate of 5 to 7 mmHg. Reducing the reaction pressure at a rate of less than 4 mmHg / min reduces the productivity because the reaction time is too long, while reducing the pressure at a rate exceeding 8 mmHg / min causes the vacuum tube to be removed while the low-molecular weight reactant is removed. The problem arises. To this end, the reaction pressure during the polycondensation reaction is reduced from 760 mmHg to 50 mmHg over preferably 90 minutes to 170 minutes, more preferably 100 minutes to 140 minutes, even more preferably 100 minutes to 120 minutes.

In addition, in the present invention, the final vacuum pressure is maintained at 40 mmHg or more, specifically 40 to 50 mmHg. If the final vacuum pressure is less than 40mmHg, the reaction proceeds rapidly, making it difficult to control the reaction, the gelation is promoted, the acid value is excessively high, and if it exceeds 50mmHg, the reaction time is too long, productivity is lowered.

In one embodiment, the reaction pressure during the polycondensation reaction after the esterification reaction is slowly reduced over 2 hours from 760mmHg to 50mmHg, and then remove the diol component produced while maintaining the reaction to reach the desired viscosity at 50 to 40mmHg do.

[Physical Properties of Manufactured Polyester Resins]

The polyester resin for toner binder of the present invention has a glass transition temperature of 60 to 80 ° C, a number average molecular weight of 2500 to 5500 g / mol, and a softening temperature of 95 to 115 ° C.

If the glass transition temperature of the polyester resin is less than 60 ℃, the durability is lowered, adversely affects the crushing efficiency due to the fine powder generation, and if it exceeds 80 ℃, low temperature fixability. In addition, when the number average molecular weight of the polyester resin is less than 2500 g / mol, the glass transition temperature is lowered, durability is significantly lowered, hot offset occurs in the toner image, and if it exceeds 5500 g / mol, low temperature fixability is reduced. The cold offset is generated in the toner image. In addition, if the softening temperature of the polyester resin is less than 95 ℃ glass transition temperature is lowered, durability is lowered, offset occurs, and if it exceeds 115 ℃ low temperature fixability is lowered.

According to another aspect of the present invention, there is provided a toner comprising the polyester resin of the present invention as described above as a binder. The toner may further include components commonly used in toner production, such as colorants, charge control agents, and waxes, in addition to the polyester resin binder of the present invention. The content of the binder and other conventional ingredients can be easily determined by those skilled in the art, and the toner can be prepared according to conventional manufacturing methods known in the art.

The toner of the present invention can be applied to various image forming apparatuses for providing images by using toner, and are particularly suitable as toners for laser printers or copiers.

The toner containing the polyester resin of the present invention as described above can provide excellent durability and low temperature fixability at the same time.

Hereinafter, the present invention will be described in more detail with reference to Examples. However, these examples are only for the understanding of the present invention, and the scope of the present invention in any sense is not limited to these examples.

Example

Example  1 to 5

The reaction mixture and esterification catalyst of the components and contents shown in the following [Table 1] were charged to a 15 liter melt condensation reactor. The temperature of the reactor was maintained at 200 to 220 ° C. for 2 hours, and the produced alcohol was removed while maintaining at 220 to 230 ° C. for 1 hour. Subsequently, after adding the titanium-based polycondensation catalyst at a concentration of 700 ppm based on the total acid content, the pressure of the reactor was reduced in pressure from 760 mmHg to 50 mmHg over 120 minutes while raising the temperature of the reactor to 250 ° C., thereby reducing the polyester resin for the toner binder. Was prepared.

Example  6

A polyester resin for a toner binder was prepared in the same manner as in Example 1 except that the pressure of the reactor was reduced in pressure from 760 mmHg to 50 mmHg over 100 minutes.

Example  7

A polyester resin for a toner binder was prepared in the same manner as in Example 1 except that the pressure of the reactor was reduced in pressure from 760 mmHg to 50 mmHg over 130 minutes.

Example  8

A polyester resin for a toner binder was prepared in the same manner as in Example 1 except that the pressure of the reactor was reduced in pressure from 760 mmHg to 50 mmHg over 140 minutes.

Comparative example

Comparative example  1 to 6

The reaction mixture and esterification catalyst of the components and contents shown in the following [Table 1] were charged to a 15 liter melt condensation reactor. The temperature of the reactor was maintained at 200 to 220 ° C. for 2 hours, and the produced alcohol was removed while maintaining at 220 to 230 ° C. for 1 hour. Subsequently, after adding the titanium-based polycondensation catalyst at a concentration of 700 ppm based on the total acid content, the pressure of the reactor was reduced in pressure from 760 mmHg to 50 mmHg over 120 minutes while raising the temperature of the reactor to 250 ° C., thereby reducing the polyester resin for the toner binder. Was prepared.

Comparative example  7

A polyester resin for a toner binder was prepared in the same manner as in Example 1 except that the pressure of the reactor was reduced in pressure from 760 mmHg to 50 mmHg over 60 minutes.

Comparative example  8

A polyester resin for a toner binder was prepared in the same manner as in Example 1 except that the pressure of the reactor was reduced in pressure from 760 mmHg to 35 mmHg over 210 minutes.

[Table 1]

* BHPP: polyoxypropylene- (n) -2,2-bis (4-hydroxyphenyl) propane

* BHEP: polyoxyethylene- (n) -2,2-bis (4-hydroxyphenyl) propane

Isosorbide: 1,4: 3,6-dianhydro-D-sorbitol

* TMA: trimellitic anhydride

* TMP: trimethylolpropane

Property measurement

The softening temperature, glass transition temperature (Tg), and number average molecular weight (Mn) of the polyester resin for toner binders prepared according to Examples and Comparative Examples were measured and shown in the following [Table 2]. Meanwhile, 93% by weight of the polyester resin for toner binder, 3% by weight of carbon black, 1.5% by weight of charge control agent, and 2.5% by weight of carnauba wax, prepared according to Examples and Comparative Examples, were mixed in a Henkel mixer for two minutes. Melt kneading with an extruder to prepare a toner composition. The prepared toner composition was pulverized to an average particle size of 8.5 μm using a jet mill-type 100AFG grinder (PULVERIZER), and then evaluated at low temperature fixing property, durability, and offset characteristics of the toner. Shown in

The softening temperature of the physical properties was measured by using a flow tester (CFT-500D) 1.5g sample at a load of 20kgf and a temperature increase rate of 6 ℃ per minute using a nozzle of 1mm in diameter, 1mm in height. The glass transition temperature was measured by using a differential scanning calorimeter (DSC) at a temperature rising rate of 10 ° C. per minute, cooling, and then increasing the temperature again. Low temperature fixability was evaluated by toner remaining when 3M tape was attached to an image paper printed at 35 ppm on a roller at 120 ° C., 130 ° C. and 140 ° C., rubbed a weight of 500 g 10 times, and the tape was removed. For durability, 10 g of pulverized toner particles were placed in a 20 ml vial, and then left in a 60 ° C. oven for 24 hours to evaluate the degree of aggregation and wax blooming. The offset characteristics were evaluated based on the change in density of the printed image when the 1000-sheet printing test was performed using a laser printer.

[Table 2]

1) Low temperature fixability

5: remaining 95% or more, 4: remaining 90-95%, 3: remaining 85-90%,

2: 80-85% remaining amount, 1: less than 80% remaining amount

Hot (hot offset): Toner melts excessively inside the fuser and contaminates the fixing roller.

Cold (cold offset): The toner is not sufficiently melted in the fixing unit and is not fixed by the fixing roller.

2) durable

5: no aggregation, 4: fine surface aggregation / dispersion in 1 ~ 2 vibrations,

3: fine coagulation / dispersion during 3-4 vibrations, 2: partial coagulation / fine dispersion during vibration,

1: full aggregate formation

3) Offset Characteristics

◎: excellent, △: normal, X: hot and cold

(Hot property: Causes burn contamination, Cold property: Unshaven appearance)

As can be seen from the results in Table 2, the toner prepared according to the embodiment was excellent in all low-temperature fixability, durability, and offset characteristics at 120 to 140 ° C.

However, if the content of isosorbide is less than 5 molar equivalents as in Comparative Example 1 or is not included at all as in Comparative Example 6, the Tg is low and the durability is lowered. This was bad. In addition, when the content of isosorbide exceeds 30 molar equivalents as in Comparative Examples 3 and 4, the durability increased due to the increase in Tg, but the low temperature fixability decreased due to excessive durability. Because of its coldness, print quality was poor.

In addition, when the content of the aromatic diol is less than 30 molar equivalents as in Comparative Example 2 or not included at all as in Comparative Example 5, both low temperature fixability and durability are deteriorated. This was bad.

On the other hand, when the reaction pressure was reduced at a rate exceeding 8 mmHg per minute as in Comparative Example 7, a problem occurred in the process of clogging the vacuum tube while removing some reactants in an unreacted state. The printing quality was poor due to hotness. In addition, when the pressure was reduced to a final vacuum pressure of less than 40 mmHg as in Comparative Example 8, it was difficult to control the reaction and the softening temperature was high, thereby lowering the low temperature fixability of the manufactured toner.

Claims (10)

It is prepared by polycondensation reaction of a reaction mixture comprising 100 molar equivalents of aromatic divalent acid, 5-30 molar equivalents of isosorbide, 10-50 molar equivalents of aliphatic diol and 30-70 molar equivalents of aromatic diol, and the glass transition. The polyester resin for toner binders whose temperature is 60-80 degreeC, number average molecular weights 2500-5500g / mol, and softening temperature is 95-115 degreeC. The group according to claim 1, wherein the aromatic divalent acid consists of terephthalic acid, isophthalic acid, dimethyl terephthalate, dimethyl isophthalate, diethyl terephthalate, diethylisophthalate, dibutyl terephthalate, dibutyl isophthalate and acid anhydrides thereof. Polyester resin for toner binder, characterized in that at least one selected from. The method of claim 1, wherein the aliphatic diol is ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, 1,4-butanediol, 1,4-butenediol, neopentin glycol, 2,3-butanediol, 1,5-pentanediol, 2,3-pentanediol, 1,6-hexanediol, 2,3-hexanediol, 3,4-hexanediol, 1,7-heptanediol, dodecanediol, 1,4- A polyester resin for a toner binder, characterized in that at least one selected from the group consisting of cyclohexane dimethanol, 1,4-cyclohexanediol and neopentyl glycol. The method of claim 1, wherein the aromatic diol is polyoxyethylene- (2,0) -2,2-bis (4-hydroxyphenyl) propane, polyoxypropylene- (2,0) -2,2-bis (4 -Hydroxyphenyl) propane, polyoxypropylene- (2,2) -polyoxyethylene- (2,0) -2,2-bis (4-hydroxyphenyl) propane, polyoxyethylene- (2,3) -2,2-bis (4-hydroxyphenyl) propane, polyoxypropylene- (6) -2,2-bis (4-hydroxyphenyl) propane, polyoxypropylene- (2,3) -2,2 -Bis (4-hydroxyphenyl) propane, polyoxypropylene- (2,4) -2,2-bis (4-hydroxyphenyl) propane, polyoxypropylene- (3,3) -3,3-bis (4-hydroxyphenyl) propane, polyoxyethylene- (3,0) -2,2-bis (4-hydroxyphenyl) propane and polyoxyethylene- (6) -2,2-bis (4-hydroxy Roxyphenyl) propane polyester resin for toner binder, characterized in that at least one selected from the group consisting of. The reaction mixture of claim 1, wherein the reaction mixture contains at least one of 0.1 to 20 molar equivalents of a trivalent or higher polyhydric alcohol with respect to 100 molar equivalents of an aromatic divalent acid and 0.1 to 20 molar equivalents of a trivalent or higher polyhydric acid relative to 100 molar equivalents of the total diol. A polyester resin for toner binder, characterized in that it further comprises. Polycondensing a reaction mixture comprising, in relative content, 100 molar equivalents of aromatic divalent acid, 5-30 molar equivalents of isosorbide, 10-50 molar equivalents of aliphatic diol, and 30-70 molar equivalents of aromatic diol, In the polycondensation reaction, the reaction pressure is reduced to 4 to 8mmHg per minute to a final vacuum pressure of 40 to 50mmHg polyester resin manufacturing method for a toner binder. The method of claim 6, wherein the reaction pressure during the polycondensation reaction is reduced in pressure from 760 mmHg to 50 mmHg over 90 to 170 minutes. The method of claim 6, wherein the reaction temperature during the polycondensation reaction is maintained at 230 to 250 ℃ polyester resin manufacturing method for a toner binder. A toner comprising the polyester resin according to any one of claims 1 to 5 as a binder. 10. The toner according to claim 9, wherein the toner is for a laser printer or a copier.