JP2977714B2 - Polyester molding - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polyester molded article, and more particularly, it has excellent transparency, heat resistance, small optical anisotropy, and excellent moldability. The present invention relates to a polyester copolymer suitable as a material for
Polyester containing bis- [4- (2-hydroxyethoxy) phenyl] fluorene as binder
Non-linear optical materials, photosensitizers, photochromic materials
And the like.

[0002]

2. Description of the Related Art In recent years, in order to improve the heat resistance of polyether,
Various components have been copolymerized or made wholly aromatic, such as polyallylate. Various proposals have been made on polyesters using 9,9-bis (4-hydroxyphenyl) fluorene.
9-bis [4- (2-hydroxyethoxy) phenyl]
Polyester copolymer using fluorene
About the polyester molding used as
Absent.

[0003] That is, it is disclosed in US Pat. No. 3,397,095 that a polymer of 9,9-bis (4-hydroxyphenyl) fluorene and terephthalic acid and isophthalic acid can be obtained from the acid chloride method.
546, 165. To improve the moldability of this product, Japanese Patent Publication No. 4-22931 discloses a mixture of 9,9-bis (4-hydroxyphenyl) fluorene, terephthalic acid, isophthalic acid and fatty acid at a specific ratio. Heat resistant polyester is shown. A method for producing a soluble heat-resistant polyarylate is disclosed in JP-A-63-152622, and a copolymer of 9,9-bis (4-hydroxyphenyl) fluorene with a specific composition ratio of terephthalic acid and isophthalic acid. The materials having the specified viscosity are disclosed in JP-A-57-192432 and JP-A-62-292830.
Also disclosed is a polyester using the 9,9-bis (4-hydroxyphenyl) fluorene and a mixture of terephthalic acid, isophthalic acid, and aliphatic dicarboxylic acid.

However, these are all 9,9-bis (4-
(Hydroxyphenyl) fluorene,
The polymerization method at that time also requires special conditions. That is, 9,9
Unlike aliphatic alcohols, the bis- (4-hydroxyphenyl) fluorene has a phenolic group at both ends, so it is very difficult to react. Therefore, the reaction at a higher temperature is required in the melt polymerization method. Conditions are required, and the resulting polymer is likely to be thermally decomposed, colored, and deteriorated in quality. In addition, under the conditions of using a polymerization method of dehydrochlorination in a solvent after the terminal group on the side of the dicarboxylic acid is converted into an acid chloride, a uniform reaction is difficult, and therefore, one having a large molecular weight distribution is generally obtained. In addition, it is necessary to carry out a large amount of post-treatment of the catalyst compound, which complicates the production method and increases the cost. Despite various improvements, the resulting material has too high a glass transition point, making injection molding difficult, and moldability is not yet satisfactory.

Conventionally, transparent resins having excellent mechanical properties have been widely used as optical materials as engineering plastics. For example, polymethyl methacrylate (hereinafter abbreviated as PMMA), polycarbonate (hereinafter abbreviated as PC), amorphous polyolefin, etc. are used as optical materials for compact discs, laser discs, lenses, etc., and for transparent parts of automobiles, etc. Have been. However, problems such as low heat resistance, high hygroscopicity and poor morphological stability, stress distortion and molecular orientation during thermoforming such as injection molding, and the resulting product has large birefringence. Or the material is extremely expensive or not fully satisfactory. Further, in recent years, optical discs for recording and reproducing information such as sound, images, characters and the like using laser light have been rapidly developed, and substrate materials having higher performance optical characteristics have been demanded.

[0006]

DISCLOSURE OF THE INVENTION The present inventors have conducted intensive studies in view of the drawbacks of the prior art, and as a result, have found a polyester polymer having a specific structure, and have completed the present invention. The objective is to use a polyester polymer that has excellent transparency, mechanical properties, and electrical properties and has sufficient heat resistance for practical use as a binder , and reacts to light incident from the outside to function. Machine
An object of the present invention is to provide a polyester molded article in which a functional material is dispersed. Another object of the present invention is to provide a polyester copolymer having low optical anisotropy, excellent moldability and dimensional stability, and suitable for engineering plastics, especially optical materials. Still another object is to provide a polyester molded article that can be easily and inexpensively produced on an industrial scale.

[0007]

That is, the object of the present invention is to provide an aromatic dicarboxylic acid or an ester-forming derivative thereof with a compound represented by the general formula (1):

Wherein R ₁ is an alkylene group having 2 to 4 carbon atoms, R ₂ ,
R ₃ , R ₄ , and R ₅ are hydrogen or an alkyl group, an aryl group, or an aralkyl group having 1 to 4 carbon atoms, which may be the same or different); A substantially linear polyester polymer comprising 2 to 4 aliphatic glycols, wherein the intrinsic viscosity of the polyester polymer (phenol 60% by weight,
(Measured at 20 ° C. in a mixed solution of 40% by weight of 1,1,2,2-tetrachloroethane) is at least 0.3, which is achieved by a molded article using a polyester polymer as a binder. You.

Hereinafter, the present invention will be described in detail. As described above, the polyester molded article of the present invention comprises an aromatic dicarboxylic acid or an ester-forming derivative thereof and a compound represented by the general formula (1):

Embedded image (R ₁ is an alkylene group having 2 to 4 carbon atoms, R ₂ , R ₃ ,
R ₄ and R ₅ are hydrogen or an alkyl group, an aryl group, or an aralkyl group having 1 to 4 carbon atoms, which may be the same or different), and a dihydroxy compound represented by the following formula: A substantially linear polyester polymer composed of 2 to 4 aliphatic glycols is used as a binder and reacts and functions with light incident from outside.
Is a polyester molded article in which an optical functional material is dispersed.

The polyester molded article of the present invention has a glass transition temperature (Tg) of 90 ° C. to 160 ° C. and an intrinsic viscosity of 0.3.
The degree of polymerization is as described above, and the fluidity of the melt is excellent. By changing the composition of 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene depending on the use, an appropriate molded article can be obtained. When the ratio of the dihydroxy compound is small relative to the total dihydroxy component, the molded body is easily deformed by heat, the heat resistance is reduced, the optical anisotropy is slightly large, and the stability of the molded body tends to be reduced. There is.

The polyester represented by the general formula (1)

The use of a dihydroxy compound represented by the following formula as a copolymerization component is a key part of the present invention. By using this, the heat resistance can be improved without impairing the moldability of the polyethylene terephthalate resin. Have been found to improve and reduce optical anisotropy. Although the reason for the latter is particularly unknown, it is presumed that the latter has a special molecular structure, that is, a structure in which a fluorene group is arranged in a plane perpendicular to the main chain direction in which two phenol groups are present. It is considered to be caused. The fact that the optical anisotropy is small can be known by measuring the birefringence of a molded article molded using a polymer material. For example, the principle and measurement method of the difference between the birefringence in the vertical direction and the birefringence from an inclined angle on an optical disk substrate are described in detail in Japanese Patent Application Laid-Open No. 63-163163. Was found to be significantly reduced. This small difference is a particularly important condition when an optical disk substrate as a high-density recording medium, particularly a magneto-optical disk, is used, and the C / N ratio (C is a carrier :: recording signal) after the recording medium is used. , N can reduce noise.

The polyester molded article of the present invention has an intrinsic viscosity of 0 in a mixed solution of 60% by weight of phenol and 40% by weight of 1,1,2,2-tetrachloroethane at 20 ° C. 0.3 or more, preferably 0.4 to 0.8. When the intrinsic viscosity is 0.3 or less, the mechanical strength of the molded product becomes insufficient. However, when the intrinsic viscosity is 0.3 or more, a molded product having sufficient mechanical strength can be obtained. As the intrinsic viscosity increases, stress distortion and molecular orientation tend to occur at the time of molding, and the birefringence of the molded article tends to increase.
A material suitable for the intended use may be appropriately selected, for example, 55 or a material as high as 0.6 to 0.8 for blow molding. The polyester polymer having the intended intrinsic viscosity can be easily obtained by adjusting polymerization conditions such as a molecular weight regulator, a polymerization time and a polymerization temperature.

The aromatic dicarboxylic acid to be provided to the polyester molded article of the present invention or the dicarboxylic acid which forms an ester-forming derivative such as an alkyl ester or phenol ester thereof includes terephthalic acid, isophthalic acid, 2,6-naphthalenedicarboxylic acid, 1,8 naphthalenedicarboxylic acid, 1,4 naphthalenedicarboxylic acid, 1,2 naphthalenedicarboxylic acid, 1,3 naphthalenedicarboxylic acid, 1,5 naphthalenedicarboxylic acid, 1,6 naphthalenedicarboxylic acid, 1,6 naphthalenedicarboxylic acid, 1, 7 naphthalenedicarboxylic acid,
2,3 naphthalenedicarboxylic acid, 2,7 naphthalenedicarboxylic acid, 2,2′-biphenyldicarboxylic acid, 3,
Aromatic dicarboxylic acids such as 3'-biphenyldicarboxylic acid, 4,4'-biphenyldicarboxylic acid, and 9,9-bis (4-carboxyphenylene) fluorene, and ester-forming derivatives thereof are exemplified. Each of them may be used alone, or two or more of them may be used as needed. Of these, terephthalic acid, isophthalic acid, 2,6-naphthalenedicarboxylic acid, and 4,4′-biphenyldicarboxylic acid are preferably used. Particularly, terephthalic acid and isophthalic acid are more preferably used from the viewpoint of optical characteristics. If necessary, at least one aliphatic dicarboxylic acid such as maleic acid, adipic acid, sebacic acid, decamethylene dicarboxylic acid or an ester-forming derivative thereof may be used in a small amount up to 10 mol% of the total acid component. can do.

In the present invention, as the dihydroxy compound represented by the general formula (1), for example, 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene, 9,9-bis [4- ( 2-hydroxyethoxy) -3-
Methylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3,
5-dimethylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-
Ethylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3,
5-diethylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-
Propylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3,
5-dipropylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-
Isopropylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3,
5-diisopropylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-
n-butylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3,
5-di-n-butylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-
Isobutylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3,
5-diisobutylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-
(1-methylpropyl) phenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3,
5-bis (1-methylpropyl) phenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-
Phenylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3,
5-diphenylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-
Benzylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3,
5-dibenzylphenyl] fluorene, 9,9-bis [4- (3-hydroxypropoxy) phenyl] fluorene 9,9-bis [4- (4-hydroxybutoxy) phenyl] fluorene and the like. Alternatively, two or more types may be used in combination. Among these, 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene is preferred in terms of optical properties and moldability.

9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene is obtained, for example, by adding ethylene oxide (hereinafter referred to as EO) to 9,9-bis (4-hydroxyphenyl) fluorene. . At this time, in addition to the 2EO adduct (9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene) in which ethylene oxide is added one molecule at a time to both hydroxyl groups of phenol, a few molecules were added in excess. Impurities such as 3EO adduct and 4EO adduct may be included. When impurities such as 3EO and 4EO are increased, the heat resistance of the polyester polymer is lowered. At this time, the purity of the 2EO adduct was 8
5% or more is sufficient, but preferably 95% or more.

In the present invention, as the aliphatic glycol, ethylene glycol, 1,3-propanediol,
1,2-propanediol, 1,4-butanediol,
1,2-butanediol, 1,3-butanediol,
Glycols such as 1,5-pentanediol, 1,4-pentanediol, and 1,3-pentanediol, and alicyclic dimethanols such as cyclohexane dimethanol and cyclopentane dimethanol, among which ethylene glycol, 1,4-butylene glycol is preferred, and ethylene glycol is particularly preferred from the viewpoint of heat resistance. These may be used alone or in combination of two or more.

A dihydroxy compound having an aromatic ring in the main chain and side chain, such as 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1-phenylethane, bis [4- ( At least one compound having an aromatic ring and sulfur in the main chain, such as 2-hydroxyethoxy) phenyl] sulfone, or another dihydroxy compound can be used in combination at a limit of 10 mol% of the total diol component.

The polyester molded article of the present invention is , for example,
It can be produced by selecting an appropriate method from known methods such as a melt polymerization method such as a transesterification method and a direct polymerization method, a solution polymerization method, and an interfacial polymerization method. The reaction conditions for the polymerization catalyst and the like at this time may be the same as those in the related art, and a known method can be used.

When a solution polymerization method, an interfacial polymerization method, or the like is employed for producing the polyester molded article of the present invention, an acid chloride is generally used as an active species of an acid component, or a solvent is used. Methylene chloride, chloroform, etc. are used as the polymer, but chlorides and catalyst compounds as by-products remain in the polymer, which are generally inferior in product quality. Must be removed. These are sheets, films, plates,
It reduces the operability in the molding process of fibers and the like, and also reduces the quality of the obtained molded body. For example, a large amount of thermal decomposition occurs during high-temperature heating. When used as an optical material, a metal thin film such as a reflective film or a recording film is fixed to a plate or a substrate by a method such as evaporation or sputtering. Therefore, it is necessary to perform a sufficient process of removing residual foreign substances such as washing and filtration, since the corrosion and the life of the product are reduced.

The polyester molded article of the present invention is particularly good when a melt polymerization method is used. That is, the compound of 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene has a terminal group very similar to that of an aliphatic glucose, and has high reactivity. This is 9,9-bis (4-
It is significantly different from (hydroxyphenyl) fluorene. For this reason, it is not necessary to use a raw material called acid chloride, and therefore, a production method in which chlorine is not essentially mixed is possible, and the amount of catalyst used can be reduced under high-temperature reaction conditions, and a method of reducing residual foreign substances is possible. It became.

In order to produce the polyester molded article of the present invention by the transesterification method of the melt polymerization method, the dihydroxy component represented by the general formula (1) is one of the glycol components in the resin.
It is preferably from 0 to 95 mol%. This is 95
If the amount is more than mol%, there may be a problem that the melt polymerization reaction does not proceed or the polymerization time becomes extremely long. When it is more than 95 mol%, there is a problem in the above-mentioned process, but it can be produced by a solution polymerization method or an interfacial polymerization method.

[0021] The polyester molded article of the present invention may contain a lubricant, a heat-resistant agent, an antistatic agent, an ultraviolet absorber,
A pigment or the like is blended. Further, the polyester molded article of the present invention
In the case of supplying to the optical material, care should be taken to prevent dust from entering, such as the step of charging the raw materials, the polymerization step, the step of pelletizing the polymer, the step of injection molding, the step of molding into a sheet or a film, etc. Is preferred. In such a case, it is generally preferable to use a class of 1000 or less for a compact disk (hereinafter referred to as a CD), and a class of 100 or less for more advanced information recording.

Since the polyester molded article of the present invention is amorphous, it is excellent in transparency, has a glass transition temperature of 90 ° C. or more, has excellent heat resistance, and has excellent melt viscoelastic properties. It is excellent in processability, hardly causes residual stress distortion and molecular orientation at the time of molding, and has a characteristic that even if it remains, the optical anisotropy is extremely small. Therefore, transparent materials and optical materials are very useful and well suited resins.

The polyester molded article of the present invention is
The terpolymer can be obtained by a conventionally known molding method, for example, an injection molding method, an injection compression molding method, a transfer molding method, a blow molding method, an extrusion molding method, a pressure molding method, a casting molding method, or the like. . When molding, a more suitable molding method may be selected from these molding methods.For example, for an optical disk substrate, a lens, a general molded part, etc., an injection molding method and an injection compression molding method are well suited, and a film, a sheet, an optical fiber, Extrusion molding is suitable for fibers and the like. In addition, a blow molding method is suitable for bottles and bags, and a pressure molding method and a transfer molding method are suitable for molding. Among them, the excellent properties of the polyester polymer of the present invention, transparency, low optical anisotropy, molded articles that require heat resistance, that is,
In order to obtain a molded article for optical use, an injection compression molding method and an extrusion molding method are preferred.

An injection compression molding machine is well suited for molding an optical disk substrate, which is an example of an optical molded product, and by appropriately selecting molding conditions such as resin temperature, mold temperature, holding pressure, etc. An excellent product having low birefringence, extremely uniform birefringence in the radial direction of the disk substrate, thickness, transferability, and no warpage can be obtained. Such molding conditions cannot be specified unconditionally depending on the composition, the degree of polymerization, and the like, but the mold temperature is preferably 20 ° C. or less of the heat distortion temperature, and is therefore 70 ° C. or more and 130 ° C. or less. The resin temperature is 270 ° C or higher and 3
The temperature is preferably 60 ° C. or lower. If the temperature is lower than 270 ° C., the fluidity and transferability of the resin deteriorate, and stress strain remains during molding to increase birefringence. On the other hand, when the temperature exceeds 360 ° C., thermal decomposition of the resin is liable to occur, which may cause a reduction in the strength and coloring of the molded product, a stain on the mirror surface of the mold and the stamper, and a deterioration in the releasability.

As described above, the polyester molded article of the present invention is amorphous and transparent. For this reason, a transparent binder
It is useful to. Thus, applications requiring transparency of the resin include, for example, non-linear optical materials, photosensitizers, and photochromic materials. These optically functional materials function by reacting to light incident from the outside. Therefore, the material in which these materials are dispersed must be transparent. here
Binders are non-linear optical materials, photosensitizers, photochromic
Material that can be effectively mixed and dispersed. Minute
The method of dispersing depends on the material.
In a solution in which the ester resin is dissolved in an organic solvent,
Optical functional materials can be mixed with appropriate surfactants
It is possible. The resin of the present invention dissolves very easily in an organic solvent, and is suitable for using this solution mixing method.

The present invention will be specifically described below with reference to examples. The intrinsic viscosity, glass transition temperature, birefringence, and total light transmittance of the copolymers in the examples were measured by the following methods.

1. Intrinsic viscosity The copolymer 0.1 was added to 50 ml of a mixed solution of 60% by weight of phenol and 40% by weight of 1,1,2,2-tetrachloroethane.
After dissolving 15 to 0.5 g at 80 ° C, the viscosity was measured and determined at 20 ° C.

2. Glass transition temperature About 10 mg of a sample was measured using a differential scanning calorimeter (Rigaku Denki DSC-8230) at a heating rate of 10 ° C./min. The glass transition temperature Tmg was determined as defined in JIS K 7121-1987.

3. Birefringence With a polarizing microscope manufactured by Carl Zeiss, Cermon, Berek, and Brace Keller type compensator were attached.
The measurement was performed using monochromatic light of 46 nm. Measurement piece is 260 ~
Melting at 300 ° C. and extrusion molding to produce a disc-shaped test piece having a diameter of 30 mm and a thickness of 1 mm, and press-forming the formed test piece at 160 to 240 ° C.
A 0μ film was obtained. The obtained film is 4 × 40 m
m to obtain a measurement test piece. Tmg + 1
The test specimen was stretched 40% at 20% / sec at a temperature of 0 ° C., and then rapidly cooled to obtain a stretched film. The birefringence of these films was measured.

[0029]

5. Tensile strength was measured according to JIS K7113. 6. Tensile modulus was measured according to JIS K7113. 7. Tensile elongation at break was measured in accordance with JIS K7113. 8. Flexural modulus Measured according to JIS K7203. 9. Flexural strength Measured according to JIS K7203. 10. Izod strength Measured according to JIS K7110. A test piece having a width of 1/2 inch was used. 11. Rockwell strength Measured according to JIS K7202. The M scale was used. 12. Water absorption After drying at 100 ° C. for 10 hours or more, it was immersed in ion-exchanged water at 23 ° C. for 24 hours and measured. 13. Refractive index Measured according to JIS K7105. 14． Total light transmittance Measured according to JIS K7105. 15. Thermal expansion coefficient Measured according to JIS K7197. 16. Specific heat Measured according to JIS K7123. 17． Heat distortion temperature Measured according to JIS K7207. Load is 18.5
It was measured in kgf / cm2. 18. Specific gravity was measured at 25 ° C. using a specific gravity bottle. 19. Molding Shrinkage A sample injection-molded with a mold having a length of 178 mm, a width of 20 mm, and a thickness of 3 mm was used. The length of the molded product relative to the length of the mold was measured, and the ratio was shown. 20. Heat Shrinkage Rate The rate of change in length after the test piece was treated at 80 ° C. for 48 hours is shown.

Hereinafter, "parts" in the examples means parts by weight. Example 1 Starting from 38 parts of dimethyl terephthalate, 35 parts of 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene and 27 parts of ethylene glycol,
As a catalyst, 0.042 parts of calcium acetate was used.
The ester exchange reaction was performed by gradually heating from 0 ° C to 230 ° C. After extracting a predetermined amount of methanol from the system, 0.012 parts of germanium oxide as a polymerization catalyst and 0.03 parts of trimethyl phosphate 0.03 in order to prevent coloring.
3 parts, and the temperature was gradually increased and reduced, and the temperature of the heating bath was increased to 280 while removing ethylene glycol generated.
° C and the degree of vacuum to 1 Torr or less. These conditions were maintained, the viscosity was increased, the reaction was terminated after reaching a predetermined stirring torque (after about 2 hours), and the reaction product was extruded into water to obtain pellets.

Table 1 shows the physical properties of the copolymer. This resin was melt molded at 290 ° C. to obtain a sample on a disk, and then pressed at 220 ° C. to obtain a 120 μm thick film. When stretched at 136 ° C., the birefringence becomes 40 × 10 ^−4.
Met.

[Table 1]

[0033]

[0034]

[0035]

Comparative Example 1 Terephthalic acid dimethyl ester 100 parts, isophthalic acid dimethyl ester 25 parts, ethylene glycol 96
Parts, calcium sulfate 0.19 parts, germanium oxide
Pellets were obtained in the same manner as in Example 1, except that 0.054 parts and 0.17 parts of trimethyl phosphate were used. Table 2 shows the evaluation results of this polymer.
Heat resistance is not good. In addition, it was found that the birefringence was large and it was not suitable for optical applications.

Comparative Example 2 Instead of ethanol, 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene, 9,9-bis-
The reaction was carried out in the same manner as in Example 1 except that (4-hydroxyphenyl) -fluorene was used. However, no increase in the viscosity of the reaction solution was observed, and the viscosity did not increase even after 4 hours from the start of the polymerization. . The reaction was poured into water but did not form a pellet. This material cannot be used in the methods of the present invention such as extrusion molding and injection molding.

Comparative Example 3 100 parts of dimethyl terephthalate, 77 parts of ethylene glycol, 0.15 part of calcium acetate, 0.043 part of germanium oxide, and 0.13 part of trimethyl phosphate were used as the raw material composition and additives. Otherwise, pellets were obtained in the same manner as in Example 1. Table 2 shows the physical properties of the obtained polymer. The film was similarly evaluated for birefringence, but the film became cloudy and could not be measured. Although this polymer can be used for special purposes, it is not suitable for the heat-resistant and optically transparent purpose of the present invention.

Comparative Example 4 In Example 1, when the stirring torque was low (1 Torr)
(About 30 minutes after the reaction reached), the reaction was extruded into water, but did not become pellets. When the intrinsic viscosity of this resin was measured, it was 0.25. Such pellets are not suitable for the purpose of the present invention, as shown in Comparative Example 2. Further, as a comparative example, a film was prepared in the same manner as in Example 1 using a commercially available polycarbonate (NOVAREX AD3 manufactured by Mitsubishi Kasei Kogyo Co., Ltd.), and the result of evaluating the birefringence was evaluated. The results are shown in Table 2. Comparison of these examples with comparative examples showed that the products of the present invention were optically transparent, had low birefringence, and were excellent in heat resistance, moldability, and the like.

[Table 2]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

Example 30 A polymer obtained in the same manner as in Example 1 and a compound of the formula (2)

The amino-substituted anthantrone represented by the following formula and tetrahydrofuran are each 10: 1 by weight.
After mixing at 0: 150 and mixing in a ball mill for 20 minutes, a film thickness of 1 mm was deposited on an aluminum evaporated PET film.
To form a carrier generation layer. Next, 4, 4 '
-Dimethyl-4 '-(4-methyl) styryl-triphenylamine and a polymer obtained in the same manner as in Example 1.
And tetrahydrofuran were mixed at a weight ratio of 10: 10: 150 and mixed in a ball mill for 20 minutes, and then applied on the carrier generation layer at a thickness of 1 micrometer to form a carrier transport layer.

The half-life exposure of the above-mentioned photoreceptor was measured. Using an electrostatic copying paper tester from Kawaguchi Electric Works for measurement, -6
A voltage of 6 kV was applied for 6 seconds, and then exposure was performed at 300 lux for 16 seconds using tungsten light as a light source to obtain a half-reduction exposure amount.
Table 8 shows the results.

[Table 8]

As described above, the polyester of the present invention
The molded product has good transparency, heat resistance, small optical anisotropy, and can provide a molding material with excellent moldability, dimensional stability, and chemical resistance. Industrially useful for applications such as printing and transparent binders.

Continuation of the front page (51) Int.Cl. ⁶ Identification symbol FI D01F 6/84 301 D01F 6/84 301K G11B 7/24 526 G11B 7/24 526J // B29K 67:00 Examiner Koji Okuma (56) References JP-A-6-322087 (JP, A) JP-A-6-192408 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) C08L 67/00-67/08 C08G 63/00 -63/91 C08K 3/00-13/08 D01F 6/62 D01F 6/78-6/94 G11B 7/24 526

Claims (7)

(57) [Claims] 1. An aromatic dicarboxylic acid or an ester-forming derivative thereof and a compound represented by the general formula (1): (R ₁ is an alkylene group having 2 to 4 carbon atoms, R ₂ , R ₃ ,
R ₄ and R ₅ are hydrogen or an alkyl group having 1 to 4 carbon atoms, an aryl group, or an aralkyl group, which may be the same or different);
A substantially linear polyester polymer comprising an aliphatic glycol having 2 to 4 carbon atoms, wherein the intrinsic viscosity of the polyester polymer (phenol 60% by weight, 1, 1
1,2,2, - using a mixed solution of 40% by weight tetrachloroethane, a polyester polymer, characterized in that measured at 20 ° C.) is 0.3 or more as a binder, an external
A polyester molded article in which an optical functional material that functions in response to incident light is dispersed. 2. The method according to claim 1, wherein the aromatic dicarboxylic acid or its ester-forming derivative is at least one aromatic dicarboxylic acid selected from terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, biphenyldicarboxylic acid or its ester-forming derivative. The polyester molded article according to claim 1, which is an ester-forming derivative . 3. The polyester according to claim 1, wherein the dihydroxy compound represented by the general formula (1) is 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene. Molded body. 4. The polyether according to claim 1, wherein the aliphatic glycol is ethylene glycol.
Steal molded body. 5. The polyether according to claim 1, wherein the aliphatic glycol is butylene glycol.
Steal molded body. 6. The resin according to claim 1, wherein the molar ratio of the dihydroxy compound represented by the general formula (1) to the aliphatic glycol having 2 to 4 carbon atoms in the resin is 10:90 or more. 5. The molded polyester of 5 . 7. The molding process is a disk substrate, lens, sheet, film, tube, or fiber formed by an injection molding machine, an extrusion molding machine, or a pressure molding machine.
The molded polyester article according to claim 6.