JPH08100053A - Polyester polymer and its molding - Google Patents

Abstract

PURPOSE: To obtain a polyester polymer excellent in optical characteristics, heat resistance, solubility in org. solvents, and moldability and esp. suitable for an optical material by synthesizing a polymer from a dicarboxylic acid or its ester-forming deriv. and a diol component contg. specific dihydroxy compds. CONSTITUTION: This polyester polymer is synthesized from a diccarboxylic acid and/or its ester-forming deriv. and a diol component contg. at least two dihydroxy compds. selected from among compds. represented by formulas I to VI (wherein R1 is a 2-4C alkylene; R2 to R5 are each H, a 1-7C alkyl, aryl, etc.;R6 is a 1-4C alkylene; R7 to R11 are each H, a 1-7C alkyl, aryl, etc.; R12 is a 1-4C alkylene; R13 to R16 are each H, a 1-7C alkyl, aryl, etc.; R17 and R18 are each a 1-4C alkylene; R19 and R20 are each H, a 1-7C alkyl, aryl, etc. (l) and (m) are each 1-8; R21 is a 1-4C alkylene; R22 to R27 are each H, a 1-7C alkyl, aryl, etc.; (n) is 0-5; R28 is a 1-4C alkylene; R29 and R30 are each a 1-10C alkyl; and R31 to R34 are each H, a 1-7C alkyl, or aryl).

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polyester polymer and a molded product thereof, and more specifically, it has excellent optical properties, heat resistance, and solubility in an organic solvent and has good moldability, and not only engineering plastics. Particularly, it relates to a polyester polymer suitable as an optical material and a molded product thereof.

[0002]

2. Description of the Related Art Polycarbonate (hereinafter referred to as PC) has been most practically used as an optical plastic.
Abbreviated as)), compact disc substrate and lens,
It has been put to practical use in automobile parts, etc. However, since PC has a large intrinsic birefringence of the molecule itself and is poor in moldability, the birefringence becomes large when formed into a molded body. This is a property unfavorable as an optical material, such as causing a signal reading or writing error when used for an optical disk substrate. Further, PC has a low hardness and has a defect that the surface is easily scratched when formed into a molded body. In addition, when PC is used as a binder for dyes and pigments, the solubility in organic solvents, especially when it has a high molecular weight, becomes a serious problem. That is, the binder is required to have high abrasion resistance, and this abrasion resistance generally becomes higher as the polymer molecular weight increases. On the other hand, in order to mold the binder, good solubility in an organic solvent is required. Since PC has a low solubility in organic solvents when it has a high molecular weight, it is limited in abrasion resistance when it is used as a binder, and therefore has a limited abrasion resistance. However, it has abrasion resistance exceeding this. Demand for binder is very high.

Polymethylmethacrylate (hereinafter abbreviated as PMMA) is known as a plastic having a small intrinsic birefringence, and is practically used as a laser disk substrate or a special lens which requires higher optical characteristics than a compact disk. Has been converted. However, PMMA has poor heat resistance. Further, since the hygroscopicity is high, there is a drawback that the molded body is easily deformed. As mentioned above, what meets all the properties required for optical plastics is:
It has not been found yet.

[0004]

DISCLOSURE OF THE INVENTION The inventors of the present invention have made extensive studies in view of the drawbacks of the prior art, and as a result, have found that the novel polyester polymer can solve these drawbacks and completed the present invention. The object of the invention is to provide an engineering plastic excellent in optical properties, heat resistance, solubility in an organic solvent, and moldability, particularly a polyester polymer suitable for optical materials.
Still another object is to provide a polyester polymer and a molded product thereof which can be easily manufactured at low cost by industrial production.

[0005]

Means for Solving the Problems The above-mentioned object is to comprise a dicarboxylic acid and / or an ester-forming derivative thereof and a diol, wherein the diol is represented by the following general formulas (1) to (6): It is achieved by a polyester polymer containing at least two kinds of dihydroxy compounds and a molded product obtained by molding the polyester polymer.

[0006]

[Chemical 7]

(R ₁ is an alkylene group having 2 to 4 carbon atoms, R ₂ , R ₃ , R ₄ and R ₅ are hydrogen or 1 carbon atom.
The alkyl groups, aryl groups and aralkyl groups of 1 to 7 may be the same or different. )

[0008]

Embedded image

(R ₆ is an alkylene group having 1 to 4 carbon atoms, R ₇ , R ₈ , R ₉ , R ₁₀ and R ₁₁ are hydrogen or an alkyl group having 1 to 7 carbon atoms, an aryl group or aralkyl. Represents a group and may be the same or different. K is a natural number from 1 to 4.)

[0010]

[Chemical 9]

(R ₁₂ represents an alkylene group having 1 to 4 carbon atoms, R ₁₃ , R ₁₄ , R ₁₅ and R ₁₆ represent hydrogen or an alkyl group having 1 to 7 carbon atoms, an aryl group or an aralkyl group. , They may be the same or different.)

[0012]

[Chemical 10]

(R ₁₇ and R ₁₈ represent an alkylene group having 1 to 4 carbon atoms and may be the same or different.
R ₁₉ and R ₂₀ represent hydrogen or an alkyl group having 1 to 7 carbon atoms, an aryl group, or an aralkyl group, and may be the same or different. l and m are natural numbers from 1 to 8. )

[0014]

[Chemical 11]

(R ₂₁ is an alkylene group having 1 to 4 carbon atoms, R ₂₂ , R ₂₃ , R ₂₄ , R ₂₅ , R ₂₆ and R ₂₇ are hydrogen or an alkyl group having 1 to 7 carbon atoms; -Ru group,
It represents an aralkyl group and may be the same or different. n is a natural number from 0 to 5. )

[0016]

[Chemical 12]

[0017] (R ₂₈ represents an alkylene group having a carbon number of 1 to up to 4, R ₂₉ and R ₃₀ represents an alkyl group having a carbon number of 1 to up to 10, it may be the same or different from each other .R _31,
R ₃₂ , R _33, and R ₃₄ are hydrogen or an alkyl group having 1 to 7 carbon atoms, an aryl group, or an aralkyl group, and may be the same or different. )

The present invention will be described in detail below.

[0019]

BEST MODE FOR CARRYING OUT THE INVENTION The polyester polymer of the present invention is
As described above, the substance is composed of a dicarboxylic acid and / or its ester-forming derivative and a diol, and the diol contains at least two or more dihydroxy compounds in the compound group represented by the general formulas (1) to (6). It is a linear polyester polymer.

The polyester polymer of the present invention has an intrinsic viscosity (phenol 60% by weight, 1,1,2,2-tetrachloroethane 40) from the viewpoints of fluidity of the melt and heat resistance of the molded product.
It is preferable that the glass transition temperature (Tg) is 0.3 or more and the glass transition temperature (Tg) is 80 ° C. or more in a wt% mixed solution at 20 ° C.). Then, by changing the type and composition of the dihydroxy compound depending on the application, a proper molded product can be obtained.

It is a key part of the present invention to use at least two kinds of dihydroxy compounds as copolymerization components among the compounds represented by the above general formulas (1) to (6). Excellent optical characteristics in combination
It has been found that heat resistance, moldability, and good solubility in organic solvents are exhibited.

The terminal groups of the dihydroxy compounds represented by the general formulas (1) to (6) are not phenolic hydroxyl groups,
An aliphatic hydroxyl group is also a key part of the present invention. That is, this allows the polymer to be obtained by the melt polycondensation method, and the foreign substances in the polyester polymer can be minimized. Further, when the phenolic hydroxyl group is used, the moldability of the obtained polyester polymer is extremely deteriorated and the mechanical strength is also deteriorated. Furthermore, the solubility in an organic solvent, which is one of the major features of the polyester polymer of the present invention, becomes extremely poor. On the other hand, in the polyester polymer of the present invention, since the terminals of the dihydroxy compounds represented by the general formulas (1) to (6) are aliphatic hydroxyl groups, the obtained polyester polymer has extremely good moldability,
It also has extremely high solubility in organic solvents.

The reason for the reduction of birefringence, which is one of the optical properties, is considered to be due to their molecular structure, although the reason is not clear. That is, the birefringence increases as the molecular polarizability anisotropy increases, but the general formulas (1), (2),
In the dihydroxy compounds represented by (3), (5) and (6), the two phenyl groups in the main chain direction do not have a horizontal three-dimensional structure, and the polarizability in the main chain direction is extremely small. Furthermore, the dihydroxy compounds represented by the general formulas (1) and (5) have an aromatic ring in the side chain, and thus have a large polarizability in the side chain direction. The dihydroxy compound represented by the general formula (4) has a structure having no aromatic ring and has essentially no polarizability anisotropy.

From the above, in order to reduce the birefringence, when an aromatic dicarboxylic acid such as terephthalic acid or 2,6-naphthalenedicarboxylic acid is used as the dicarboxylic acid, the polarizability in the main chain direction is large. Dihydroxy compounds represented by the general formulas (1) and (5) having an aromatic ring in the side chain are particularly preferable, and when an aliphatic dicarboxylic acid such as succinic acid is used as the dicarboxylic acid, the aromatic ring is included in the main chain. The dihydroxy compound represented by the general formula (4) which does not have is particularly preferable.

The dihydroxy compounds represented by the general formulas (1), (2), (3), (5) and (6) are effective for improving the refractive index because they have an aromatic ring. Among them, the compound represented by the general formula (1) having a large number of aromatic rings is most preferable.

Further, regarding the improvement of heat resistance, the dihydroxy compounds represented by the general formulas (1), (2), (3), (5) and (6) are generally added to the phenyl group in the main chain direction. The dihydroxy compound represented by the formula (4) is derived from the tricyclodecane ring. To improve the heat resistance, the compounds represented by the general formulas (1) and (3) having a structure in which a phenyl ring in the main chain direction is fixed are particularly preferable.

The improvement in the solubility in organic solvents is due to the dihydroxy compounds represented by the general formulas (1) to (6) having a relatively large side chain. That is, due to the influence of this large side chain, the intermolecular interaction is weakened and the solubility in the organic solvent is improved. Regarding the solubility in this organic solvent, general formulas (1), (2) having a large side chain,
The compounds represented by (5) and (6) are particularly preferable.

The polyester polymer of the present invention has an intrinsic viscosity of 0.3 or more measured at 20 ° C. in a mixed solution of 60% by weight of phenol and 40% by weight of 1,1,2,2-tetrachloroethane. Is preferred. Intrinsic viscosity is 0.3
With the above, a molded product having sufficient mechanical strength can be obtained. On the other hand, as the intrinsic viscosity is smaller, stress strain and molecular orientation are less likely to occur during molding, and the birefringence of the molded product can be reduced,
For example, 0.3 to 0.6 having a lower intrinsic viscosity is particularly preferable for molding an optical disk substrate. In addition, an intrinsic viscosity of 0.4 to 0.7 is particularly preferable for lens applications requiring high mechanical strength and precision moldability, and binders such as dyes and pigments have high abrasion resistance. Since it is necessary, those having a high intrinsic viscosity of 0.7 to 1.2 are particularly preferable.
As described above, a polyester polymer having an intrinsic viscosity suitable for the intended use may be appropriately selected. The polyester polymer having the desired intrinsic viscosity can be easily adjusted by the polymerization conditions such as the molecular weight modifier, the polymerization time and the polymerization temperature.

Examples of the dicarboxylic acid used for the polyester polymer of the present invention include dicarboxylic acids usually used for optical plastics. Examples thereof include terephthalic acid, isophthalic acid, 2,6-naphthalenedicarboxylic acid, and the like.
1,8-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,2-naphthalenedicarboxylic acid, 1,
3-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 1,6-naphthalenedicarboxylic acid, 1,7-
Aromatic aromatics such as naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 2,2'-biphenyldicarboxylic acid, 3,3'-biphenyldicarboxylic acid, 4,4'-biphenyldicarboxylic acid Dicarboxylic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, methylmalonic acid, ethylmalonic acid, methylsuccinic acid, 2,2-
Aliphatic dicarboxylic acids such as dimethylsuccinic acid, 2,3-dimethylsuccinic acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 1,4-cyclohexanedicarboxylic acid, 2,5-dimethyl-1,4- Examples thereof include alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid and 2,3,5,6-tetramethyl-1,4-cyclohexanedicarboxylic acid. Depending on the type of dihydroxy compound to be copolymerized, among these, succinic acid is used when low birefringence is important, and succinic acid is used when high refractive index and high heat resistance are important.
6-naphthalenedicarboxylic acid, and terephthalic acid are particularly preferred when moldability is important. These may be used alone or in combination of two or more if necessary.

Examples of the dihydroxy compound represented by the general formula (1) to be used for the polyester polymer of the present invention include 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-n-dibutylphenyl] -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-di (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- (2-Hydroxypropoxy) phenyl] -fluorene and the like can be mentioned. Among these, 9,9-bis- [4- (2-hydroxyethoxy) phenyl] -fluorene is optical properties, heat resistance and molding. It has the best balance of properties and is particularly preferable because it has a great effect on the improvement of the solubility in an organic solvent. These may be used alone or in combination of two or more if necessary.

Examples of the dihydroxy compound represented by the general formula (2) for use in the polyester polymer of the present invention include 1,1-bis [4- (2-hydroxyethoxy) phenyl] cyclohexane and 1,1-bis [ 4- (2-hydroxyethoxy) -3-methylphenyl] cyclohexane, 1,1-bis [4- (2-hydroxyethoxy)]
-3,5-Dimethylphenyl] cyclohexane, 1,1
-Bis [4- (2-hydroxyethoxy) -3-ethylphenyl] cyclohexane, 1,1-bis [4- (2-
Hydroxyethoxy) -3,5-diethylphenyl] cyclohexane, 1,1-bis [4- (2-hydroxyethoxy) -3-propylphenyl] cyclohexane,
1,1-bis [4- (2-hydroxyethoxy) -3,
5-dipropylphenyl] cyclohexane, 1,1-bis [4- (2-hydroxyethoxy) -3-isopropylphenyl] cyclohexane, 1,1-bis [4- (2
-Hydroxyethoxy) -3,5-diisopropylphenyl] cyclohexane, 1,1-bis [4- (2-hydroxyethoxy) -3-n-butylphenyl] cyclohexane, 1,1-bis [4- (2-hydroxy) Ethoxy) -3,5-di-n-butylphenyl] cyclohexane, 1,1-bis [4- (2-hydroxyethoxy)-
3-isobutylphenyl] cyclohexane, 1,1-bis [4- (2-hydroxyethoxy) -3,5-diisobutylphenyl] cyclohexane, 1,1-bis [4-
(2-Hydroxyethoxy) -3- (1-methylpropyl) phenyl] cyclohexane, 1,1-bis [4-
(2-Hydroxyethoxy) -3,5-bis (1-methylpropyl) phenyl] cyclohexane, 1,1-bis [4- (2-hydroxyethoxy) -3-phenylphenyl] cyclohexane, 1,1-bis [ 4- (2-hydroxyethoxy) -3,5-diphenylphenyl] cyclohexane, 1,1-bis [4- (2-hydroxyethoxy) -3-benzylphenyl] cyclohexane, 1,
1-bis [4- (2-hydroxyethoxy) -3,5-
Dibenzylphenyl] cyclohexane, 1,1-bis [4- (2-hydroxyethoxy) phenyl] -4-methylcyclohexane, 1,1-bis [4- (2-hydroxyethoxy) phenyl] -2,4,6 -Trimethylcyclohexane, 1,1-bis [4- (2-hydroxypropoxy) phenyl] cyclohexane, 1,1-bis [4- (2-hydroxybutoxy) phenyl] cyclohexane, and 1-4 hydrogens of these cyclohexanes. Are substituted with an alkyl group having 1 to 7 carbon atoms, an aryl group, an aralkyl group, and the like. Among these, 1,
1-bis [4- (2-hydroxyethoxy) phenyl]
Cyclohexane is particularly preferred because it is effective in improving mechanical strength and solubility in organic solvents. These may be used alone or in combination of two or more as needed.

Examples of the dihydroxy compound represented by the general formula (3) for use in the polyester polymer of the present invention include bis- [4- (2-hydroxyethoxy) phenyl] -sulfone and bis- [4- (2- Hydroxyethoxy) -3-methylphenyl] -sulfone, bis-
[4- (2-hydroxyethoxy) -3,5-dimethylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy) -3-ethylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy) ) -3,5-Diethylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy) -3-propylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy) -3,5
-Dipropylphenyl] -sulfone, bis- [4-
(2-Hydroxyethoxy) -3-isopropylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy) -3,5-diisopropylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy) -3. -N
-Butylphenyl] -sulfone, bis- [4- (2-
Hydroxyethoxy) -3,5-di-n-butylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy) -3-isobutylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy)- 3,5-diisobutylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy) -3- (1-methylpropyl) phenyl] -sulfone, bis- [4- (2-hydroxyethoxy) -3,5 -Di (1-methylpropyl) phenyl] -sulfone, bis- [4- (2-hydroxyethoxy) -3-phenylphenyl] -sulfone, bis-
[4- (2-hydroxyethoxy) -3,5-diphenylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy) -3-benzylphenyl] -sulfone, bis- [4- (2-hydroxyethoxy) ) -3,5
-Dibenzylphenyl] -sulfone, bis- [4-
(2-Hydroxypropoxy) phenyl] -sulfone, bis- [4- (2-hydroxybutoxy) phenyl] -sulfone and the like can be mentioned, and among these, bis- [4- (2-hydroxyethoxy) phenyl] -sulfone. Is particularly preferable because it has a great effect on improving heat resistance and does not impair moldability and mechanical strength. These may be used alone or in combination of two or more as required.

Examples of the dihydroxy compound represented by the general formula (4) for use in the polyester polymer of the present invention include tricyclodecane dimethylol, tricyclodecane diethylol, tricyclodecane dipropyrrole, tricyclodecane dibutyrol. , Dimethyltricyclodecane dimethylol, diethyltricyclodecane dimethylol, diphenyltricyclodecane dimethylol, dibenzyltricyclodecane dimethylol, tetramethyltricyclodecane dimethylol, hexamethyltricyclodecane dimethylol, octamethyltricyclo Decanedimethylol and the like can be mentioned. Among these, tricyclodecanedimethylol is particularly preferable because it has an effect of reducing birefringence and has good heat resistance and moldability. These may be used alone or in combination of two or more as needed.

Examples of the dihydroxy compound represented by the general formula (5) for use in the polyester polymer of the present invention include 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1-phenylethane, 1, 1-bis [4-
(2-Hydroxyethoxy) -3-methylphenyl]-
1-phenylethane, 1,1-bis [4- (2-hydroxyethoxy) -3,5-dimethylphenyl] -1-phenylethane, 1,1-bis [4- (2-hydroxyethoxy) -3- Ethylphenyl] -1-phenylethane, 1,1-bis [4- (2-hydroxyethoxy)-
3,5-diethylphenyl] -1-phenylethane,
1,1-bis [4- (2-hydroxyethoxy) -3-
Propylphenyl] -1-phenylethane, 1,1-bis [4- (2-hydroxyethoxy) -3,5-dipropylphenyl] -1-phenylethane, 1,1-bis [4- (2-hydroxy) Ethoxy) -3-isopropylphenyl] -1-phenylethane, 1,1-bis [4-
(2-Hydroxyethoxy) -3,5-diisopropylphenyl] -1-phenylethane, 1,1-bis [4-
(2-Hydroxyethoxy) -3-n-butylphenyl] -1-phenylethane, 1,1-bis [4- (2-
Hydroxyethoxy) -3,5-n-dibutylphenyl] -1-phenylethane, 1,1-bis [4- (2-
Hydroxyethoxy) -3-isobutylphenyl] -1
-Phenylethane, 1,1-bis [4- (2-hydroxyethoxy) -3,5-diisobutylphenyl] -1-
Phenylethane, 1,1-bis [4- (2-hydroxyethoxy) -3- (1-methylpropyl) phenyl]-
1-phenylethane, 1,1-bis [4- (2-hydroxyethoxy) -3,5-di (1-methylpropyl) phenyl] -1-phenylethane, 1,1-bis [4-
(2-Hydroxyethoxy) -3-phenylphenyl]
-1-Phenylethane, 1,1-bis [4- (2-hydroxyethoxy) -3,5-diphenylphenyl] -1
-Phenylethane, 1,1-bis [4- (2-hydroxyethoxy) -3-benzylphenyl] -1-phenylethane, 1,1-bis [4- (2-hydroxyethoxy) -3,5-di Benzylphenyl] -1-phenylethane, 1,1-bis [4- (2-hydroxyethoxy)
Phenyl] -1- (4-methylphenyl) ethane, 1,
1-bis [4- (2-hydroxyethoxy) phenyl]
-1- (2,4,6-trimethylphenyl) ethane,
1,1-bis [4- (2-hydroxyethoxy) phenyl] -1-phenylpropane, 1,1-bis [4- (2
-Hydroxyethoxy) phenyl] -1-phenyl-n
-Butane, 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1-phenyl-2-methylpropane,
1,1-bis [4- (2-hydroxyethoxy) phenyl] -1-phenyl-2-methylbutane, 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1-phenyl-2-ethylbutane, 1,1-bis [4- (2-
Hydroxyethoxy) phenyl] -diphenylmethane,
1,1-bis [4- (2-hydroxyethoxy) phenyl] -1,2-diphenylethane, 1,1-bis [4-
(2-Hydroxypropoxy) phenyl] -1-phenylethane, 1,1-bis [4- (2-hydroxybutoxy) phenyl] -1-phenylethane, etc., and side chain phenyl groups attached to their central carbons. In which 1 to 4 hydrogen atoms of 1 to 4 are substituted with an alkyl group, an aryl group, or an aralkyl group having 1 to 7 carbon atoms.
-Bis [4- (2-hydroxyethoxy) phenyl]-
1-Phenylethane is particularly preferable because it has a great effect on reducing birefringence and improving solubility in an organic solvent, and does not impair moldability and mechanical strength. These may be used alone or in combination of two or more as needed.

Examples of the dihydroxy compound represented by the general formula (6) for use in the polyester polymer of the present invention include 2,2-bis [4- (2-hydroxyethoxy) phenyl] propane and 2,2-bis [ 4- (2-hydroxyethoxy) phenyl] butane, 2,2-bis [4-
(2-hydroxyethoxy) phenyl] pentane, 2,
2-bis [4- (2-hydroxyethoxy) phenyl]
-3-methylbutane, 2,2-bis [4- (2-hydroxyethoxy) phenyl] hexane, 2,2-bis [4
-(2-hydroxyethoxy) phenyl] -3-methylpentane, 2,2-bis [4- (2-hydroxyethoxy) phenyl] -3,3-dimethylbutane, 2,2-bis [4- (2- Hydroxyethoxy) phenyl] heptane, 2,2-bis [4- (2-hydroxyethoxy) phenyl] -3-methylhexane, 2,2-bis [4-
(2-Hydroxyethoxy) phenyl] -4-methylhexane, 2,2-bis [4- (2-hydroxyethoxy) phenyl] -5-methylhexane, 2,2-bis [4- (2-hydroxyethoxy) Phenyl] -3,3
-Dimethylpentane, 2,2-bis [4- (2-hydroxyethoxy) phenyl] -3,4-dimethylpentane, 2,2-bis [4- (2-hydroxyethoxy) phenyl] -4,4-dimethyl Pentane, 2,2-bis [4- (2-hydroxyethoxy) phenyl] -3-ethylpentane, 2,2-bis [4- (2-hydroxyethoxy) phenyl] octane, 2,2-bis [4- (2
-Hydroxyethoxy) phenyl] nonane, 2,2-bis [4- (2-hydroxyethoxy) phenyl] decane, 2,2-bis [4- (2-hydroxyethoxy) phenyl] dodecane, 3,3-bis [ 4- (2-hydroxyethoxy) phenyl] -5-methylhexane, 4,4
-Bis [4- (2-hydroxyethoxy) phenyl]-
6-methylheptane, 5,5-bis [4- (2-hydroxyethoxy) phenyl] -7-methyloctane, 6,
6-bis [4- (2-hydroxyethoxy) phenyl]
-8-Methylnonane, 7,7-bis [4- (2-hydroxyethoxy) phenyl] -9-methyldecane, 8,8
-Bis [4- (2-hydroxyethoxy) phenyl]-
10-methyl dodecane, 2,2-bis [4- (2-hydroxyethoxy) -3-methylphenyl] -4-methylpentane, 2,2-bis [4- (2-hydroxyethoxy) -3,5- Dimethylphenyl] -4-methylpentane, 2,2-bis [4- (2-hydroxyethoxy)-
3-Ethylphenyl] -4-methylpentane, 2,2-
Bis [4- (2-hydroxyethoxy) -3,5-diethylphenyl] -4-methylpentane, 2,2-bis [4- (2-hydroxyethoxy) -3-propylphenyl] -4-methylpentane, 2,2-bis [4- (2
-Hydroxyethoxy) -3,5-dipropylphenyl] -4-methylpentane, 2,2-bis [4- (2-
Hydroxyethoxy) -3-isopropylphenyl]-
4-methylpentane, 2,2-bis [4- (2-hydroxyethoxy) -3,5-diisopropylphenyl]-
4-methylpentane, 2,2-bis [4- (2-hydroxyethoxy) -3-butylphenyl] -4-methylpentane, 2,2-bis [4- (2-hydroxyethoxy) -3,5- Dibutylphenyl] -4-methylpentane, 2,2-bis [4- (2-hydroxyethoxy)-
3-isobutylphenyl] -4-methylpentane, 2,
2-bis [4- (2-hydroxyethoxy) -3,5-
Diisobutylphenyl] -4-methylpentane, 2,2
-Bis [4- (2-hydroxyethoxy) -3- (1-
Methylpropyl) phenyl] -4-methylpentane,
2,2-bis [4- (2-hydroxyethoxy) -3,
5-bis (1-methylpropyl) phenyl] -4-methylpentane, 2,2-bis [4- (2-hydroxyethoxy) -3-phenylphenyl] -4-methylpentane, 2,2-bis [4 -(2-hydroxyethoxy)-
3,5-diphenylphenyl] -4-methylpentane,
2,2-bis [4- (2-hydroxyethoxy) -3-
Benzylphenyl] -4-methylpentane, 2,2-bis [4- (2-hydroxyethoxy) -3,5-dibenzylphenyl] -4-methylpentane, 2,2-bis [4- (2-hydroxy) Propoxy) phenyl] -4-
Examples thereof include methylpentane and 2,2-bis [4- (2-hydroxybutoxy) methylphenyl] -4-methylpentane. Among these, 2,2-bis [4- (2-
Hydroxyethoxy) phenyl] -4-methylpentane is particularly preferable because it has an appropriately large branched side chain, has a large effect of improving the solubility in an organic solvent, and does not impair heat resistance. In addition, 2,2-bis [4
-(2-Hydroxyethoxy) phenyl] -propane is particularly preferable because it has excellent heat resistance and mechanical strength and does not impair the solubility in organic solvents. These may be used alone or in combination of two or more as needed.

Examples of the diol used for the polyester polymer of the present invention, other than the dihydroxy compounds represented by the general formulas (1) to (6), include diols usually used in optical plastics. For example, ethylene glycol, 1,3-propanediol,
1,2-propanediol, 1,4-butanediol,
Aliphatic glycols such as 1,3-butanediol and 1,2-butanediol, 1,4-cyclohexanedimethanol, 2,5-dimethyl-1,4-cyclohexanedimethanol, 2,3,5,6- Alicyclic glycols such as tetramethyl-1,4-cyclohexanedimethanol and 1,3-cyclopentanedimethanol, 1,4-benzenedimethanol, 1,3-benzenedimethanol, 4,
Aromatic diols such as 4'-diphenyldimethanol and the like can be mentioned. Among these, ethylene glycol, which has good reactivity and moldability, is particularly preferable. These may be used alone or in combination of two or more.

The polyester polymer of the present invention can be produced by selecting an appropriate method from known methods such as a transesterification method, a melt polymerization method such as a direct polymerization method, a solution polycondensation method and an interfacial polymerization method. Further, the reaction conditions such as the polymerization catalyst at that time may be the same as conventional ones, and a known method can be used.

By the way, when a solution polymerization method, an interfacial polymerization method or the like is adopted in producing the polyester polymer of the present invention, generally, an acid chloride is used as an active species of an acid component, or methylene chloride is used as a solvent. Chloroform is used, but chlorides and catalyst compounds that are by-products remain in the polymer, and these reduce the operability in the molding process of sheets, films, plates, fibers, etc. Also reduces the quality of. 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 on a plate or a substrate by a method such as vapor deposition or sputtering. Corrosion reduces the life and reliability of the product.

The polyester polymer of the present invention is particularly good when the melt polymerization method is used. That is, the general formula (1)
Since the terminal group of the dihydroxy compound represented by (6) to (6) has a property very similar to that of an aliphatic compound, the reactivity is high. For this reason, it is not necessary to use a raw material called acid chloride, and therefore a production method essentially free of chlorine is possible, and it is possible to reduce the amount of catalyst used under the reaction conditions at high temperature and to reduce the amount of residual foreign matter in the polyester polymer. Obtainable.

In order to produce the polyester polymer of the present invention by the transesterification method of the melt polymerization method, at least two or more dihydroxy compounds in the compound group represented by the general formulas (1) to (6) are used together. It is used as a polymerization component, and the total amount of dihydroxy compounds used is particularly preferably 10 mol% or more and 95 mol% or less of the diol. 10
When it is at least mol%, the optical properties, heat resistance, and solubility in organic solvents will be further improved. When it is 95 mol% or less, the melt polymerization reaction sufficiently proceeds, and the polyester polymer can be polymerized by freely adjusting the molecular weight. However, 9
Even if it is more than 5 mol%, the polymerization time can be shortened by polymerizing by the solution polymerization method or the interfacial polymerization method.

As described above, the dihydroxy compounds represented by the general formulas (1) to (6) provided for the polyester polymer of the present invention have different effects on the optical properties, heat resistance and solubility in organic solvents. Therefore, by changing the copolymerization ratio of the two, it is possible to obtain a polyester polymer having properties suitable for the intended use.

The polyester polymer of the present invention may be blended with a lubricant, a heat-resistant agent, an antistatic agent, an ultraviolet absorber, a pigment and the like depending on the purpose of molding.

Examples of the molded product obtained by molding the polyester polymer of the present invention include optical disk substrates, lenses, sheets, films, fibers, and binders such as organic dyes and pigments.

When the polyester polymer of the present invention is used as an optical material, it includes a raw material charging step, a polymerization step, a pelletizing step of the polymer, injection molding, a sheet shape,
It is preferable to manufacture in an environment in which dust is not mixed in in the step of forming into a film. In such a case, a class of 1000 or less is usually preferable for compact discs, and a class of 100 or less is preferable for more advanced information recording.

Since the polyester polymer of the present invention is amorphous, it has excellent transparency, and since it has excellent melt viscoelastic properties, it has excellent moldability, and residual stress strain and molecular orientation occur during molding. In addition to being difficult, even if they remain, the birefringence of the molded article is extremely small because the intrinsic birefringence of the molecule itself is small. Therefore,
Very well suited for optical materials.

Further, the polyester polymer of the present invention has a feature that the solubility in an organic solvent such as chloroform, tetrahydrofuran, dioxane, etc. does not decrease due to its molecular structure even when the molecular weight becomes considerably high. Therefore, it is suitable for binders such as dyes and pigments.

The polyester polymer molding of the present invention is obtained by molding the above-mentioned polyester polymer by a conventionally known molding method such as injection molding, injection compression molding, transfer molding, blow molding, extrusion molding or pressure molding. Method, casting molding method, dipping method and the like. Upon molding, a more suitable molding method may be selected from these, for example, optical disk substrates, lenses, general molded parts, etc. are well compatible with injection molding method and injection compression molding method, and films, sheets, optical fibers, fibers, etc. Extrusion method is compatible. The blow molding method is suitable for bottles, bags, etc., the pressure molding method and transfer molding method are suitable for molding, and the casting molding method is suitable for binders. Among them, the excellent properties of the polyester polymer of the present invention, transparency, low birefringence, a molded body that requires heat resistance,
That is, in order to obtain a disc substrate and a lens, an injection molding method,
The injection compression molding method and the extrusion molding method are preferably the dipping and casting molding methods in order to take advantage of high solubility in an organic solvent.

Injection compression molding is well suited for molding an optical disk substrate, which is an example of an optical molded body, and by appropriately selecting molding conditions such as resin temperature, mold temperature, and holding pressure, birefringence of the disk substrate can be obtained. It is small, and the birefringence in the diameter direction of the disk substrate, the thickness, the transferability, etc. are extremely uniform and excellent without warping. Such molding conditions cannot be unconditionally specified depending on the composition, molecular weight, etc., but the mold temperature is particularly preferably 20 ° C. or more lower than the heat distortion temperature of the resin. The resin temperature is particularly preferably 240 ° C. or higher and 330 ° C. or lower. If it is 240 ° C. or higher, the fluidity and transferability of the resin are good. Further, if the temperature is 330 ° C. or lower, the resin is less likely to undergo thermal decomposition.

[0049]

EXAMPLES The present invention will be specifically described with reference to the following examples. The refractive index, birefringence index, glass transition temperature, intrinsic viscosity, moldability, Izod impact strength and solubility in organic solvents in the examples were evaluated by the following methods.

(1) Refractive index The refractive index was measured with an Abbe refractometer.

(2) Birefringence Index A non-oriented film having a length of 40 mm, a width of 2 mm and a thickness of 0.1 mm is heat-stretched at a temperature of Tg + 10 ° C. and a stretching rate of 20% / sec. Birefringence was measured with an ellipsometer using a 630 nm light source.

(3) Glass Transition Temperature About 10 mg of a sample was used in a differential scanning calorimeter (Rigaku Denki DSC-8230) and heated at a heating rate of 10 ° C./min for measurement.

(4) Intrinsic Viscosity Using a mixed solvent of phenol and 1,1,2,2-tetrachloroethane (mixing weight ratio 60:40), dissolution at 80 ° C. and measurement in a 20 ° C. constant temperature bath did.

(4) Moldability Using a small injection molding machine, 100 disc-shaped plates having a diameter of 40 mm and a thickness of 1.2 mm were continuously molded. As a result, when the ratio of defective products with cracks or defects within 10% is ○, 10
When it exceeded%, it was defined as x.

(5) Izod impact strength It was measured according to JIS K-7110.

(6) Solubility in organic solvent Tetrahydrofuran, chloroform and dioxane were subjected to a melting test under the conditions of 30% by weight and room temperature.
The evaluation was made in 3 grades: soluble, poorly soluble, and insoluble.

Example 1 2,6-naphthalenedicarboxylic acid dimethyl ester 1.
0 mol, 9,9-bis [4- (2-hydroxyethoxy) phenyl] -fluorene 0.8 mol, 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1-phenylethane 0.1 Molar and ethylene glycol 3.0
Using 0.008 mol of calcium acetate and 0.0002 mol of manganese acetate as a transesterification catalyst, the starting materials were added to a reaction tank and gradually heated from 170 ° C. to 240 ° C. according to a conventional method with stirring. Transesterification was performed. After extracting a predetermined amount of methanol out of the system, 0.0008 mol of germanium oxide as a polymerization catalyst and 0.0012 mol of phosphoric acid triethyl ester as a coloring and antioxidant were added, and the temperature was raised and the pressure was gradually reduced. While removing the generated ethylene glycol, the heating bath temperature is set to 290 ° C. and the vacuum degree is set to 1 Torr or less. While maintaining this condition, waiting for the increase in viscosity, the reaction was terminated when the torque applied to the stirrer reached a predetermined value, and the mixture was extruded into water to obtain pellets.

The polymer had a very high refractive index of 1.65, a low birefringence of 0.0030 and a glass transition temperature of 170 ° C. The intrinsic viscosity was 0.45, the Izod impact strength was 4.2 Kgf · cm / cm ² , and the moldability was good.

Example 2 0.5 mol of terephthalic acid dimethyl ester as a raw material,
2,6-naphthalenedicarboxylic acid dimethyl ester 0.
5 mol, 9,9-bis [4- (2-hydroxyethoxy) phenyl] -fluorene 0.8 mol, 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1-phenylethane 0.1 Molar and ethylene glycol 3.0
Pellets were obtained in the same manner as in Example 1 except that mol was used.

The polymer had an extremely high refractive index of 1.64, a low birefringence of 0.0019 and a glass transition temperature of 155 ° C. The intrinsic viscosity was 0.48 and the Izod impact strength was 4.8 Kgf · cm / cm ² . Also, the moldability was good.

Examples 3 to 9 and Comparative Example 1 Pellets were obtained in the same manner as in Example 1 except that the raw material composition was changed as shown in Table 1, and the physical properties of the polymer were evaluated. Table 1 shows the evaluation results.

Comparative Example 2 Pellets were obtained by changing the composition of raw materials and changing the polymerization method to interfacial polymerization, and evaluated the physical properties of the polymer. Table 1 shows the evaluation results.

Comparative Example 3 A commercially available PC was evaluated. The evaluation results are shown in Table 1.

[0064]

[Table 1]

As is clear from Table 1, Comparative Example 1 has a large birefringence, a low glass transition temperature and poor moldability. Comparative Example 2 has poor moldability and low Izod impact strength. Comparative Example 3 has a large birefringence. On the other hand, the polyester polymers of Examples 1 to 3 of the present invention have an extremely high refractive index, and are particularly suitable for fields such as lenses that require a high refractive index. Further, the polyester polymers of the present invention of Examples 4 to 6 use succinic acid as the dicarboxylic acid, and therefore have a very low birefringence, and are particularly suitable for fields such as optical disk substrates that require low birefringence. is there. In addition, Example 1
All of the polyester polymers of the present invention Nos. 1 to 9 have a high refractive index, a small birefringence and a glass transition temperature of 80.
It is extremely superior in terms of optical properties, heat resistance, moldability, and mechanical strength, such as high temperature above ℃, excellent moldability, and high impact strength.

Example 10 2,6-Naphthalenedicarboxylic acid dimethyl ester 1.
0 mol, 1,1-bis [4- (2-hydroxyethoxy) phenyl] -cyclohexane 0.6 mol, 2,2-
Bis [4- (2-hydroxyethoxy) phenyl] -4
-Methyl pentane (0.2 mol) and ethylene glycol (3.0 mol) were used as raw materials, and zinc acetate (0.0003 mol) was used as a transesterification catalyst.
Transesterification was carried out by gradually heating from 140 ° C. to 240 ° C. according to a conventional method while stirring. After extracting a predetermined amount of methanol out of the system, 0.0012 mol of germanium oxide as a polymerization catalyst and 0.0015 mol of phosphoric acid triethyl ester as a coloring and antioxidant were added, and the temperature was raised and the pressure was gradually reduced. , While removing the generated ethylene glycol, heating tank temperature 290 ℃, vacuum degree 1 Tor
reach r or less. While maintaining this condition, waiting for the increase in viscosity, the reaction was terminated when the torque applied to the stirrer reached a predetermined value, and the mixture was extruded into water to obtain pellets.

Although this polymer has a high intrinsic viscosity of 0.82, tetrahydrofuran, chloroform,
It rapidly dissolved in both dioxane. The glass transition temperature was as high as 135 ° C.

Example 11 0.3 mol of dimethyl terephthalate as a raw material,
2,6-naphthalenedicarboxylic acid dimethyl ester 0.
7 mol, 1,1-bis [4- (2-hydroxyethoxy) phenyl] -cyclohexane 0.6 mol, 2,2-
Bis [4- (2-hydroxyethoxy) phenyl] -4
Pellets were obtained in the same manner as in Example 10 except that 0.2 mol of methylpentane and 3.0 mol of ethylene glycol were used.

Examples 12 to 19 and Comparative Example 4 Pellets were obtained in the same manner as in Example 10 except that the composition of the raw materials was changed as shown in Table 2, and the physical properties of the polymer were evaluated.
Table 2 shows the evaluation results.

Comparative Examples 5 to 6 The modified polycarbonates (PC-Z-TYPE 1, 2) for binders such as commercially available organic dyes and pigments were evaluated in the same manner as in Examples 10 to 19. Table 2 shows the evaluation results
Shown in

[0071]

[Table 2]

As is apparent from Table 2, Comparative Example 4,
6 is insoluble in all of tetrahydrofuran, chloroform and dioxane, and Comparative Example 5 also has extremely poor solubility.
On the other hand, the polyester polymers of the present invention of Examples 10 to 19 have extremely high solubility in tetrahydrofuran, chloroform and dioxane and are particularly suitable for the field of binders such as organic dyes and pigments.

Example 20 1.0 mol of dimethyl terephthalate, 0.6 mol of 9,9-bis [4- (2-hydroxyethoxy) phenyl] -fluorene, bis [4- (2-hydroxyethoxy) phenyl] Starting from 0.2 mol of sulfone and 3.0 mol of ethylene glycol, 0.0008 mol of calcium acetate and manganese acetate of 0.004 as transesterification catalyst.
Using 0002 mol, these were put into a reaction tank and, while stirring, were gradually heated from 140 ° C. to 240 ° C. according to a conventional method to perform transesterification. After extracting a predetermined amount of methanol out of the system, 0.0008 mol of germanium oxide as a polymerization catalyst and 0.0012 mol of phosphoric acid triethyl ester as a coloring and antioxidant were added, and the temperature was raised and the pressure was gradually reduced. While heating ethylene glycol generated, the temperature of the heating bath is set to 270 ° C. and the degree of vacuum is set to 1 Torr or less. While maintaining this condition, waiting for the increase in viscosity, the reaction was terminated when the torque applied to the stirrer reached a predetermined value, and the mixture was extruded into water to obtain pellets.

The polymer had a very high refractive index of 1.65, a low birefringence of 0.0021 and a high glass transition temperature of 147 ° C. Further, the intrinsic viscosity was 0.45 and the molecular weight was in a practical range.

Examples 21 to 26 Pellets were obtained in the same manner as in Example 20 except that the composition of the raw materials was changed as shown in Table 3, and the physical properties of the polymer were evaluated.
The evaluation results are shown in Table 3.

Comparative Example 7 A commercially available polymethylmethacrylate (PMMA) was evaluated in the same manner as in Examples 20 to 26. The evaluation results are shown in Table 3.

[0077]

[Table 3]

As is clear from Table 3, Comparative Example 1 has a large birefringence and a low glass transition temperature. Comparative Example 3 has a large birefringence. Comparative Example 7 has a low refractive index. On the other hand, the polyester polymers of Examples 20 to 26 of the present invention have a high refractive index, a low birefringence index, and a high glass transition temperature, and thus have a very good balance of optical properties and heat resistance. Therefore, it is suitable for optical fields such as optical disc substrates, lenses, sheets, films, fibers or binders such as organic dyes and pigments.

Next, a molded product molded from the polyester polymer of the present invention will be specifically described with reference to examples of an optical disk substrate, a lens and an organic photosensitive drum. Incidentally, vertical birefringence in the examples, tilt birefringence,
The total light transmittance, drum formability, and abrasion resistance were measured by the methods described below.

(7) Vertical Birefringence A disk substrate was molded and the retardation in the direction perpendicular to the substrate surface was measured with an ellipsometer.

(8) Inclined birefringence A disk substrate was formed, the substrate surface was inclined at 30 degrees, and the retardation was measured with an ellipsometer.

(9) Total light transmittance Measured according to JIS K-7105.

(10) Drum moldability A resin was dissolved in tetrahydrofuran at a concentration of 40% by weight together with a dye and applied on an aluminum drum by a dipping method to form a simple organic photoreceptor drum. The moldability at this time was evaluated in three grades of ◯, Δ, and ×.

(11) Abrasion resistance: The degree of reduction of the film on the surface after a 2000-sheet copying test was carried out using the drum molded according to (10) was evaluated as 3 for ○, Δ, and ×.
The grade was evaluated.

Example 27 1.0 mol of terephthalic acid, 0.8 mol of 9,9-bis [4- (2-hydroxyethoxy) phenyl] -fluorene, 1,1-bis [4- (2-hydroxyethoxy)] A polyester polymer composed of 0.1 mol of phenyl] -cyclohexane and 0.1 mol of ethylene glycol was injection-compressed and molded at a resin temperature of 300 ° C. and a mold temperature of 110 ° C. to obtain an optical disk substrate. The vertical birefringence of this optical disk substrate was as small as 10 nm and the tilt birefringence was as small as 30 nm. Further, the glass transition temperature was as high as 150 ° C., which showed excellent heat resistance.

Example 28, Comparative Examples 8-9 Example 27 except that the type of resin was changed as shown in Table 4.
An optical disk substrate was obtained in the same manner as above, and the characteristics were evaluated.
Table 4 shows the evaluation results.

[0087]

[Table 4]

As is clear from Table 4, Comparative Example 8 has a large birefringence, particularly a large gradient birefringence and a low glass transition temperature, and Comparative Example 9 has a large birefringence, particularly a large gradient birefringence. On the other hand, the optical discs of Examples 27 and 28 have extremely small birefringence, that is, they have extremely excellent signal reading and writing capabilities. It also has high heat resistance.

Example 29 2,6-naphthalenedicarboxylic acid 1.0 mol, 9,9-
Bis [4- (2-hydroxyethoxy) phenyl] -fluorene 0.8 mol, 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1-phenylethane 0.1
A polyester polymer of the present invention consisting of 1 mol of ethylene glycol and 0.1 mol of ethylene glycol was injection-molded at a resin temperature of 300 ° C. and a mold temperature of 120 ° C. to obtain a lens. The refractive index of this lens is extremely high at 1.65, and the birefringence is 0.0030.
Was small. Moreover, the total light transmittance was excellent at 90%, and the glass transition temperature was also high at 170 ° C.

Example 30, Comparative Examples 10-12 Example 29 except that the kind of resin was changed as shown in Table 5.
A lens was obtained in the same manner as in 1. and its characteristics were evaluated. The evaluation results are shown in Table 5.

[0091]

[Table 5]

As is clear from Table 5, Comparative Example 1
0 and 11 have a high birefringence, and Comparative Example 12 has a low refraction index. On the other hand, Examples 29 and 30 have extremely high refractive index, small birefringence, high total light transmittance, and very excellent optical characteristics. Furthermore, the heat resistance is also good.

Example 31 0.3 mol of terephthalic acid, 0.7 mol of 2,6-naphthalenedicarboxylic acid, 0.6 mol of 1,1-bis [4- (2-hydroxyethoxy) phenyl] -cyclohexane,
A polyester polymer of the present invention consisting of 0.2 mol of 2,2-bis [4- (2-hydroxyethoxy) phenyl] -4-methylpentane and 0.2 mol of ethylene glycol was dissolved in 40% by weight of tetrahydrofuran together with an organic dye. Then, a simple organic photoconductor drum was formed by the dipping method. Its moldability was extremely good. Again 2000
The surface film loss after copying was extremely small and the abrasion resistance was excellent.

Examples 32 to 33, Comparative Examples 13 to 15 Example 31 except that the type of resin was changed as shown in Table 6.
A drum was molded in the same manner as in. The evaluation results are shown in Table 6.

[0095]

[Table 6]

As is clear from Table 6, Comparative Example 13
Nos. 15 to 15 have poor drum formability and low abrasion resistance. On the other hand, Examples 31 to 33 have extremely good drum moldability,
Extremely high abrasion resistance.

[0097]

As described above, the polyester polymer of the present invention is excellent in optical properties, heat resistance, moldability and mechanical properties, and has very good solubility in organic solvents. Therefore, it is possible to provide a polyester polymer suitable for optical applications such as optical disk substrates, lenses, sheets, films, tubes, fibers and binders such as organic dyes and pigments, and molded products thereof.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Office reference number FI Technical display location D01F 6/84 K 306 D 309 G02B 1/04 G11B 7/24 526 J 7215-5D

Claims (2)

[Claims] 1. A dicarboxylic acid and / or an ester-forming derivative thereof and a diol, wherein the diol is at least two dihydroxy compounds selected from the group of compounds represented by the following general formulas (1) to (6). A polyester polymer comprising. Embedded image (R ₁ is an alkylene group having 2 to 4 carbon atoms, R ₂ ,
R ₃ , R ₄ , and R ₅ represent hydrogen or an alkyl group having 1 to 7 carbon atoms, an aryl group, or an aralkyl group, and may be the same or different. ) (R ₆ is an alkylene group having 1 to 4 carbon atoms, R ₇ ,
R ₈ , R ₉ , R ₁₀ and R ₁₁ represent hydrogen or an alkyl group having 1 to 7 carbon atoms, an aryl group or an aralkyl group, and may be the same or different. k is a natural number from 1 to 4. ) [Chemical 3] (R ₁₂ is an alkylene group having 1 to 4 carbon atoms, R ₁₃ ,
R ₁₄ , R ₁₅ and R ₁₆ represent hydrogen or an alkyl group having 1 to 7 carbon atoms, an aryl group or an aralkyl group, and may be the same or different. ) [Chemical 4] (R ₁₇ and R ₁₈ represent an alkylene group having 1 to 4 carbon atoms and may be the same or different. R ₁₉ and R _18
20 represents hydrogen or an alkyl group having 1 to 7 carbon atoms, an aryl group or an aralkyl group, which may be the same or different. l and m are natural numbers from 1 to 8. ) [Chemical 5] (R ₂₁ is an alkylene group having 1 to 4 carbon atoms, R ₂₂ ,
R ₂₃ , R ₂₄ , R ₂₅ , R ₂₆ and R ₂₇ represent hydrogen or an alkyl group having 1 to 7 carbon atoms, an aryl group or an aralkyl group, and may be the same or different. n is a natural number from 0 to 5. ) [Chemical 6] (R ₂₈ represents an alkylene group having 1 to 4 carbon atoms, R ₂₉ and R ₃₀ represent an alkyl group having 1 to 10 carbon atoms,
They may be the same or different. R ₃₁ , R ₃₂ , R ₃₃ and R ₃₄ are hydrogen or an alkyl group having 1 to 7 carbon atoms, an aryl group or an aralkyl group, and may be the same or different. ) 2. A molded product obtained by molding the polyester polymer according to claim 1.