JP2556900B2 - Aliphatic polyester - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to an aliphatic polyester which is preferably used as a material for various molded articles and the like.

(Prior Art) Generally, in order for a material to exhibit rubber elasticity, it is necessary that an amorphous polymer whose molecular chain can easily rotate is partially crosslinked. For example, in elastic rubber, sulfur molecules form a network structure by bridging the molecular chains by chemical bonds. In addition to rubber, materials combining various polymer compounds and crosslinking agents have been proposed. A cross-linking process is required to mold these materials, and since they do not exhibit thermoplasticity after being chemically cross-linked, cross-linked materials cannot be molded by injection molding or extrusion.

In recent years, thermoplastic elastomers that exhibit rubber elasticity at 5 temperatures and are plasticized at high temperatures have been developed, and various types of thermoplastic elastomers have been manufactured and marketed. This thermoplastic elastomer does not require a long-time cross-linking step unlike the conventional rubber, and can be molded by injection molding or extrusion molding. The molecular structure of thermoplastic elastomers is characterized by cross-linking that is not based on strong chemical bonds, that is,
It is in a system that applies some kind of constraint between polymers that is effective only at around room temperature, and a polymer aggregate consisting of soft segments and hard segments is a typical structure of a thermoplastic elastomer. The soft segment and the hard segment have different chemical structures from each other. In the hybrid composition of the two, the homogenous parts agglomerate, and the heterogeneous parts form a micro-unbalanced structure in which the phases are separated from each other. The agglutinated portion shows a binding effect between the molecules.

Examples of the thermoplastic elastomer include styrene type, olefin type, urethane type, ester type and amide type. In the styrene series, polystyrene forms a frozen phase as a hard segment and binds between molecular chains, resulting in rubber elasticity. In the olefin system, the polypropylene crystal phase acts as a hard segment. In the urethane type, the polyurethane segment causes physical crosslinks between molecular chains by hydrogen bonds. Further, the ester-based polybutylene terephthalate chain acts as a hard segment, and the amide-based nylon chain such as 6-nylon or 6,6-nylon acts as a hard segment.

(Problems to be Solved by the Invention) As described above, since the thermoplastic elastomer exhibits rubber elasticity at room temperature and can be molded, it is widely used for automobile parts and various industrial products. However, conventional thermoplastic elastomers have lower heat resistance and poorer creep properties than the cross-linking type rubber because they are restricted by the softening melting point of the part because they are cross-linked by physical restraint. Was becoming. For example, the melting point of Perprene S-9001 manufactured by Toyobo Co., Ltd., which is known as the ester type with the highest heat resistance among thermoplastic elastomers,
223 ℃, heat distortion temperature (low load) 146 ℃, even in the urethane system, its softening point is at most 140 ℃.

The present invention has been made in view of such circumstances, and an object of the present invention is to provide a fat that has properties as a thermoplastic elastomer, is excellent in heat resistance and mechanical properties, and is also excellent in molding processability. To provide group polyester.

(Means for Solving the Problems) The aliphatic polyester of the present invention comprises a monohydroxy compound represented by the general formula [I] below and an aliphatic dicarboxylic acid represented by the general formula [II] below. An acid and an aliphatic diol are the main constituent components, and the content ratio of the monohydroxy compound is 0.1 to 20 mol% in the hydroxy component, and a dilute solution of orthochlorophenol is used.
The intrinsic viscosity as measured by an Ubbelohde viscometer is 0.4 or more and 2.0 or less, thereby achieving the above object.

(In the formula, R ¹ represents an alkylene group, and n is 0 or 1.) HOOC- (CH ₂ ) m-COOH [II] (In the formula, m is an integer of 0 to 10) The above formula [I] The monohydroxy compound represented by is a rigid low molecular weight compound having a paraphenylene skeleton, and the melting point of these compounds is extremely high, reflecting the characteristic molecular structure. Furthermore, the paraphenylene skeleton is known to be effective as a mesogen for low-molecular liquid crystal compounds, and it has a strong cohesive force not only in the solid state but also in the high temperature state (molten state). It means that. Therefore, when the above-mentioned monohydroxy compound [I] is incorporated into the polymer terminal, it brings about very strong physical cross-linking with high heat resistance, and a thermoplastic elastomer excellent in heat resistance is produced.

In the monohydroxy compound [I], R ¹ is preferably an ethylene group or a propylene group, n is 0 or 1, and examples thereof include 4-hydroxy-p-terphenyl and 4- (2-hydroxyethoxy) -p-terphenyl. Etc.
The synthesis method of 4-hydroxy-p-terphenyl and 4- (2-hydroxyethoxy) -p-terphenyl is shown below.

The above monohydroxy compounds [I] may be used alone or in combination.

Polyester is obtained by polycondensing equimolar amounts of dicarboxylic acid and diol. In the aliphatic polyester of the present invention, in addition to the above monohydroxy compound [I], the kind of compound as a constituent component and the compounding ratio of the compound By changing, the properties of the aliphatic polyester and the physical properties of the molded product obtained from the aliphatic polyester can be freely changed.

An aliphatic polyester suitable as a thermoplastic elastomer contains a monohydroxy compound [I], the above-mentioned aliphatic dicarboxylic acid [II], and an aliphatic diol as main constituent components.

Examples of the aliphatic dicarboxylic acids of the general formula _{HOOC- (CH 2) m-COOH} (m is an integer of 0) is a dicarboxylic acid represented by, the use of dicarboxylic acids in which the carbon number exceeds 10, polyester The physical properties of the molded product obtained from are deteriorated. As the dicarboxylic acid, for example, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, sebacic acid are preferably used.

Examples of the aliphatic diol include glycol and / or polyalkylene oxide. Examples of the glycol include ethylene glycol, propylene glycol, trimethylene glycol, 1,4-butanediol, 1,3-butanediol, 1,5-pentanediol, 1,6-
Hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, cyclopentane-1,2-diol, cyclohexane-1,2-diol, cyclohexane- 1,3-diol, cyclohexane-1,4-diol, cyclohexane-1,4-
Examples include dimethanol and the like, which may be used alone or in combination of two or more kinds.

Examples of the polyalkylene oxide include polyethylene oxide, polypropylene oxide, polytetramethylene oxide, polyhexamethylene oxide and the like, and these may be used alone or in combination of two or more kinds.

The number average molecular weight of the polyalkylene oxide is preferably 100 to 20,000, because the ability to impart flexibility to the resulting polyester decreases as the number average molecular weight decreases, and the physical properties such as thermal stability of the resulting polyester decrease when the number average molecular weight becomes too large. ，
It is more preferably 500 to 5,000.

The aliphatic polyester of the present invention may further contain a dihydroxy compound represented by the above formula [II] as a constituent component. These two types of rigid monomers [I]
In the aliphatic polyester in which [III] and (III) are introduced into the polymer chain and at the polymer terminal, more physical crosslinks are formed, and the properties as a thermoplastic elastomer having heat resistance are remarkably improved.

If you expect the outstanding effects described above, [II
The number of benzene rings in [I] must be at least three. Furthermore, as the number of benzene rings increases, the physical crosslink becomes stronger and the melting point rises remarkably. However, considering the ease of handling during polymerization and the difficulty of synthesis, the number of benzene rings in [III] is 3 or 4, ie paraterphenyl or paraquaterphenyl skeletons are used.

The dihydroxy compound represented by the above formula [III] is a low molecular weight compound exhibiting liquid crystallinity, the alkylene groups R ² and R ³ are preferably ethylene groups or propylene groups, and q and r are preferably 0 or 1, 4,4 "-dihydroxy-p-terphenyl represented by the formula [A] and 4,4" represented by the following formula [B]
-Dihydroxy-p-quaterphenyl and 4,4-di (2-hydroxyethoxy) -p-quaterphenyl represented by the following formula [C] are preferably used.

The transition temperature of 4,4 ″ -dihydroxy-p-terphenyl [A] from the crystalline state to the liquid crystal state is about 260 ° C., and that of 4,4-dihydroxy-p-quaterphenyl [B] is 33 ° C.
6 ° C, that of 4,4-di (2-hydroxyethoxy) -p-quaterphenyl [C] is 403 ° C. Further, the liquid crystal state means a state in which the compound is in a molten state and the molecules maintain the alignment state.

The above dihydroxy compounds [III] may be used alone or in combination. 4,4-dihydroxy-p-quaterphenyl [B] can be obtained, for example, by the method described in Journal of Chemical Society, 1379-85 (1940), or by using 4-hydroxy-4′-bromobiphenyl in the presence of an alkali catalyst as a palladium catalyst. The dimer can be synthesized by heating and pressurizing to react with the dimer, and then by acid precipitation. 4,4-Di (2-hydroxyethoxy) -p-quaterphenyl [C] can be obtained by adding ethylene oxide to 4,4-dihydroxy-p-quaterphenyl [B]. Also 4,4-
Dihydroxy-p-quaterphenyl [B] and 4,4
-Di (2-hydroxyethoxy) -p-quaterphenyl [C] is acetylated when it is polycondensed with dicarboxylic acid to give polyester, and 4,4-dihydroxy-p-quaterphenyl and 4,4 It may also be used as -di (2-acetoxyethoxy) -p-quaterphenyl.

Liquid crystal molecules generally have high crystallinity, and as described above,
4,4 "-dihydroxy-p-terphenyl [A], 4,4
-Dihydroxy-p-quaterphenyl [B] and 4,
Since 4-di (2-hydroxyethoxy) -p-quarterphenyl [C] has a high transition point from its crystal to the liquid crystal state, when these dihydroxy compounds [III] are incorporated in the polymer chain, Polymers show unique properties.

That is, since the dihydroxy compound [III] exhibits crystallinity and its transition point is high, a strong and heat-resistant physical crosslink is formed even when the amount of the dihydroxy compound [III] is small. As a result, it is presumed that a thermoplastic elastomer having high heat resistance can be obtained without impairing the flexibility derived from the soft segment.

Further, a three-component aliphatic polyester comprising the above monohydroxy compound [I], an aliphatic diol and an aliphatic dicarboxylic acid [II], or a monohydroxy compound [I], a dihydroxy compound [III], an aliphatic diol and a fat A quaternary aliphatic polyester composed of a group dicarboxylic acid [II] may contain other reaction components, for example, a poly-silicone having two hydroxyl groups, a lactone, or an aromatic hydroxycarboxylic acid as a constituent component. .

The above-mentioned polysilicone has two hydroxyl groups, and dimethylpolysiloxane, diethylpolysiloxane, diphenylpolysiloxane having two hydroxyl groups at the molecular ends are preferable. The number average molecular weight of polysilicone is
When it becomes smaller, the ability to impart flexibility to the polyester produced decreases, and when it becomes larger, it becomes difficult to produce the polyester, so 100 to 20,000 is preferable, and 500 to 5,000 is more preferable.

The lactone is a compound that opens a ring and reacts with an acid and a hydroxyl group to add an aliphatic chain, which imparts flexibility to the polyester, and which has 4 or more carbon atoms in the ring. It is preferably a 5-membered to 8-membered ring, and examples thereof include ε-caprolactone, δ-valerolactone, γ-butyrolactone and the like.

The aromatic hydroxycarboxylic acid imparts rigidity and liquid crystallinity to the polyester, and includes salicylic acid, metahydroxybenzoic acid, parahydroxybenzoic acid, 3-chloro-4-hydroxybenzoic acid, 3-bromo-4-hydroxyl. Benzoic acid, 3-methoxy-4-hydroxybenzoic acid, 3-
Methyl-4-hydroxybenzoic acid, 3-phenyl-4-hydroxybenzoic acid, 2-hydroxy-6-naphthoic acid, 4-
Examples thereof include hydroxy-4′-carboxybiphenyl, and preferred are parahydroxybenzoic acid, 2-hydroxy-6-naphthoic acid, and 4-hydroxy-4′-carboxybiphenyl.

Further, the above aliphatic polyester may contain an aromatic diol other than the dihydroxy compound [III] or an aromatic dicarboxylic acid as a constituent component in order to improve the mechanical properties of the polyester.

Examples of the aromatic diol include hydroquinone, resorcin, chlorohydroquinone, bromohydroquinone, methylhydroquinone, phenylhydroquinone, methoxyhydroquinone, phenoxyhydroquinone, 4,4′-dihydroxybiphenyl, 4,4′-dihydroxydiphenyl ether, 4,4′- Dihydroxydiphenyl sulfide, 4,4 '
-Dihydroxydiphenyl sulfone, 4,4'-dihydroxybenzophenone, 4,4'-dihydroxydiphenylmethane, bisphenol A, 1,1-di (4-hydroxyphenyl) cyclohexane, 1,2-bis (4-hydroxyphenoxy) ethane, Examples thereof include 1,4-dihydroxynaphthalene and 2,6-dihydroxynaphthalene.

Examples of the aromatic dicarboxylic acid include terephthalic acid, isophthalic acid, metal salts of 5-sulfoitophthalic acid, 4,4'-dicarboxybiphenyl, 4,4'-dicarboxydiphenyl ether, 4,4'-dicarboxydiphenyl. Sulfide, 4,4'-dicarboxydiphenyl sulfone, 3,3'-dicarboxybenzophenone, 4,4'-dicarboxybenzophenone, 1,2-bis (4-carboxyphenoxy) ethane, 1,4-dicarboxynaphthalene , Or 2,6-dicarboxynaphthalene.

The monohydroxy compound [I] used in the present invention is introduced at the polymer terminal, and its content is preferably 0.1 to 20 mol% in the hydroxy component used. Here, the hydroxy component includes an aliphatic diol, a monohydroxy compound, and optionally a dihydroxy compound. The molar ratio of the monohydroxy compound [I] is
If it is less than 0.1 mol%, physical cross-linking by the hard segment will be insufficient and sufficient physical properties and heat resistance will not be reached. On the other hand, if it exceeds 20 mol%, the molecular weight does not rise sufficiently, and only those with inferior physical properties are obtained. When the monohydroxy compound [I], the aliphatic diol, and the dihydroxy compound [III] are used as the hydroxy components, the monohydroxy compound [I] and the dihydroxy compound [III] among the hydroxy components are used. ], The molar ratio of the hydroxy compound is preferably 0.1 to 30 mol% in the total hydroxy component. If the molar ratio of [I] + [III] in the hydroxy component is less than 0.1 mol%, physical crosslinking by the hard segment will be insufficient, and sufficient physical properties and heat resistance will be difficult to develop. Further, when the molar ratio of the hydroxy compound [I] + [III] in the hydroxy component exceeds 30 mol%, the elastic modulus of the aliphatic polyester tends to be high and the elastomer tends to be unsuitable. However, this has high heat resistance and can be suitably used as a thermoplastic resin having excellent mechanical properties.

As the method for polymerizing the aliphatic polyester of the present invention, any method can be adopted. First, the case where the monohydroxy compound [I] is used alone without using the dihydroxy compound [III] will be described. For example, after esterifying an aliphatic dicarboxylic acid [II], about 2
React with a molar equivalent of aliphatic diol at 100 ℃ ~ 250 ℃,
An aliphatic diol adduct of an aliphatic dicarboxylic acid is produced by dealcoholization reaction, and then the adduct and the above monohydroxy compound [I] are produced at 200 ° C. to 350 ° C. with an aliphatic diol to produce an aliphatic polyester. Method, method of esterifying aliphatic dicarboxylic acid [II] as a constituent, reacting with hydroxy component ([I] + aliphatic diol), and polymerizing by dealcoholization, halogen compound of aliphatic dicarboxylic acid [II] And a hydroxy component ([I] + aliphatic diol) are reacted in a suitable solvent such as pyridine, and a metal salt of the hydroxy component ([I] + aliphatic diol) is halogenated with an aliphatic dicarboxylic acid [II]. The aliphatic polyester can be obtained by a conventional reaction between a dicarboxylic acid and an alcohol, such as a method of reacting with a compound.

Furthermore, the structure of the aliphatic polyester can be regulated by changing the addition order of the monohydroxy compound [I] during the polymerization. For example, in the method of (1), since the reaction occurs only at the terminal, it is preferable to add the monohydroxy compound (I) after the reaction between the aliphatic dicarboxylic acid [II] and the aliphatic diol has sufficiently proceeded.

On the other hand, in the case of 1, since the reaction takes place even in the polymer chain, there is no particular limitation on the addition timing of the monohydroxy compound [I], and a polymer having a high degree of polymerization can be obtained. Further, a pre-synthesized aliphatic polyester is kneaded with a monohydroxy compound [I] or an acetylated product of the monohydroxy compound under reduced pressure heating, and the molecular chain is based on the monohydroxy compound [I] by dealiphatic diol or transesterification reaction. It is also possible to introduce segments.

Next, the case where the monohydroxy compound [I] and the dihydroxy compound [III] are used in combination will be described.

The polymerization method of the aliphatic polyester is the same as that of the method described above except that both the monohydroxy compound [I] and the dihydroxy compound [III] are used in place of the monohydroxy compound [I]. The same method as in, except that the aliphatic dicarboxylic acid [III] is added to the component ([I] + aliphatic diol), the halide of the aliphatic dicarboxylic acid [II] and the hydroxy component (aliphatic diol + [III]) ) In a suitable solvent such as pyridine, and finally reacting with a monohydroxy compound [I], wherein a metal alcoholate of a hydroxy component (aliphatic diol + [III]) is replaced with an aliphatic dicarboxylic acid [II]. Dicarbohydrates, which are conventionally known, such as a method of reacting with a metal alcoholate of a monohydroxy compound [I] after reacting with a halide It is possible to obtain an aliphatic polyester by reaction of the acid with an alcohol.

Further, the previously synthesized aliphatic polyester is kneaded with the above-mentioned dihydroxy compound, monohydroxy compound or dihydroxy compound, and an acetylated product of the monohydroxy compound under reduced pressure heating, and the aliphatic hydroxy diol or the dihydroxy compound is added to the molecular chain by a transesterification reaction. It is also possible to introduce segments based on monohydroxy compounds.

In the polycondensation, a catalyst generally used in producing polyester may be used. The catalyst includes metals such as lithium, sodium, potassium, cesium, magnesium, calcium, barium, strontium, zinc, aluminum, titanium, cobalt, germanium, tin, lead, antimony, arsenic, cerium, boron, cadmium, and manganese. The organic metal compounds, organic acid salts, metal alkoxides, metal oxides and the like can be mentioned.

Particularly preferred catalysts are calcium acetate, diacyl stannous tin, tetraacyl stannic tin, dibutyltin oxide, dibutyltin dilaurate, dimethyltin malate, tin dioctanoate, tin tetraacetate, triisobutylaluminum, tetrabutyltitanate, germanium dioxide, and trisodium. It is antimony oxide. Two or more of these catalysts may be used in combination. In addition, water, alcohol, glycol, etc., which are by-products of polymerization, are efficiently distilled off,
In order to obtain a high molecular weight polymer, the reaction system is
It is preferable to reduce the pressure to 1 mmHg or less. The reaction temperature is generally between 150 and 350 ° C.

The polyester of the present invention is as described above, and is an inorganic material such as glass fiber, carbon fiber, boron fiber, silicon carbide fiber, alumina fiber, amorphous fiber, silicon-titanium-carbon fiber, etc. within a range not impairing its practical use. Fiber, organic fiber such as aramid fiber, calcium carbonate, titanium oxide,
Inorganic fillers such as mica, talc, triphenylphosphite, trilaurylphosphite, trisnonylphenylphosphite, 2-tert-butyl-α- (3-tert-butyl-4-hydroxyphenyl) -p-cumenylbis ( Heat stabilizers such as p-nonylphenyl) phosphite, flame retardants such as hexabromocyclododecane, tris- (2,3-dichloropropyl) phosphate, pentabromophenylallyl ether, p-tert-butylphenyl salicylate, 2- Hydroxy-4-methoxybenzophenone, 2-
UV absorbers such as hydroxy-4-methoxy-2'-carboxybenzophenone, 2,4,5-trihydroxybutyrophenone, butylhydroxyanisole, butylhydroxytoluene, distearylthiodipropionate, dilaurylthiodipropionate, hinder Antioxidants such as dephenol antioxidants, N, N-bis (hydroxyethyl) alkylamines, alkylallyl sulfonates,
Antistatic agents such as alkylsulfanates, inorganic substances such as barium sulfate, alumina and silicon oxide, higher fatty salts such as sodium stearate, barium stearate and sodium palmitate; organic compounds such as benzyl alcohol and benzophenone; high crystallization A crystallization accelerator such as polyethylene terephthalate or polytrans-cyclohexanedimethanol terephthalate may be added. The aliphatic polyester of the present invention is used by mixing it with another thermoplastic resin such as polyolefin, modified polyolefin, polystyrene, polyamide, polycarbonate, polysulfone, polyester, or by mixing with a rubber component to modify its properties. You may.

The aliphatic polyester of the present invention is formed into a molded product by press molding, extrusion molding, injection molding, blow molding or the like. The physical properties of the molded article can be arbitrarily changed depending on its constituent components, its compounding ratio and the like. The molded products are flexible molded products such as automobile parts, hoses, belts, packings, paints,
It is suitable for use as an adhesive.

(Example) Below, this invention is demonstrated based on an Example.

<4,4-dihydroxy-p-quaterphenyl> To 60.0 g of 4-hydroxy-4'-bromobiphenyl,
Methanol 100g, 10wt% sodium hydroxide aqueous solution 300g, 5w
The disodium salt of 4,4-dihydroxy-p-quaterphenyl was obtained by adding 13% of t% palladium / carbon and reacting at 120 ° C. and 5 atm for 4 hours. N, N-Dimethylformamide was added to this solid, and the catalyst was separated by heating and filtration, and the filtrate was acidified with dilute sulfuric acid and washed with methanol to give 4,4-dihydroxy-white crystalline powder. p-Quaterphenyl (hereinafter referred to as DHQ) was obtained. The liquid crystal transition temperature of DHQ was 336 ° C.

Examples 1 and 2 <Synthesis of bis (2-hydroxyethyl) adipate (BHEA)> Dimethyl adipate was placed in a glass flask having an inner volume of 1 equipped with a stirrer, a thermometer, a gas blowing port and a distillation port.
87.1g (0.5mol), ethylene glycol 74.4g (1.2mo
l), as a catalyst, calcium acetate and a small amount of antimony trioxide were added. After replacing the inside of the flask with nitrogen, the inside of the flask was heated and reacted at 180 ° C. for 2 hours. Along with the reaction, methanol began to distill from the flask, and bis (2
-Hydroxyethyl) adipate (hereinafter referred to as BHEA)
Was generated.

<Preparation of Aliphatic Polyester> 4-Hydroxy-p-terphenyl (hereinafter referred to as HT) was added to the above flask in a molar ratio shown in Table 1, and the temperature of the flask was raised to 300 ° C. The reaction was continued for about 1 hour. Next, the distillation port was connected to a vacuum device, and the reaction was carried out for 2 hours while the pressure inside the flask was reduced to 1 mmHg or less. With the reaction, ethylene glycol was distilled out, and an extremely viscous liquid was produced in the flask.

The melting point of the aliphatic polyester thus obtained was measured, and the results are shown in Table 1. The intrinsic viscosity of the obtained aliphatic polyester measured by a Ubbelohde viscometer at 30 ° C. using a dilute solution of orthochlorophenol was 1.10.

Example 2 149.1 g of BHEA (0.5 mo, synthesized in the same manner as in Example 1)
l), 4,4 "-dihydroxy-p-terphenyl (0.025mo
l) and HT (0.025mol) were added to the flask and the temperature was raised to 300 ° C, and the reaction was continued for about 1 hour in this state. Then, the distillation port was connected to a vacuum chamber and the flask pressure was reduced to 1 mmHg or less for 2 hours. Let With the reaction, ethylene glycol was distilled out, and an extremely viscous liquid was obtained in the flask.

The melting point of the aliphatic polyester thus obtained was measured, and the results are shown in Table 1. The limiting viscosity of the obtained aliphatic polyester measured by a Ubbelohde viscometer at 30 ° C. using a dilute solution of orthochlorophenol was 1.15.

Comparative Example 1 The melting point of a polymer obtained by polymerizing BHEA alone was measured, and the results are shown in Table 1. Using a dilute solution of the obtained aliphatic polyester, orthochlorophenol
The intrinsic viscosity measured by an Ubbelohde viscometer at 30 ° C is 0.
Was eight.

Comparative Examples 2 and 3 Perprene S-9001 commercially available from Toyobo Co., Ltd.
(Comparative Example 2) and Hytrel 7247 manufactured by Toray DuPont
The melting point of (Comparative Example 3) was measured, and the results are shown in Table 1.

From the results shown in Table 1, the aliphatic polyester containing the monohydroxy compound [I] in the molecular chain has a higher melting point and excellent heat resistance than a polymer containing no compound or a commercially available thermoplastic elastomer. I understand. In addition, by including the dihydroxy compound [III] in the molecular chain,
Further, the melting point can be increased.

(Effects of the Invention) The aliphatic polyester of the present invention comprises an aliphatic polyester mainly composed of an aliphatic dicarboxylic acid and an aliphatic diol, and a segment based on a dihydroxy compound or a monohydroxy compound having high crystallinity and a high melting point. Since it has been introduced, it not only has the performance as a thermoplastic elastomer, but also has excellent heat resistance, mechanical properties, and moldability.

Front Page Continuation (72) Inventor Toranosuke Saito 5-17-21 Yamatedai, Ibaraki City, Osaka Prefecture (72) Inventor Hiroki Kadomachi 7-20 Otemachi, Ibaraki City, Osaka Prefecture (72) Inventor Daishiro Kishimoto Osaka 2-11-20 Mishimaoka, Ibaraki-shi, Ume Umeyama Mansion 102 (56) Reference JP-A-2-212449 (JP, A) JP-A-2-212516 (JP, A) JP-A-2-311524 ( JP, A) Soviet patent invention 186124 (SU, A) Plastic, 38 [9] (1987) P. 14

Claims (2)

(57) [Claims] 1. A main constituent component is a monohydroxy compound represented by the following formula [I], an aliphatic dicarboxylic acid represented by the following formula [II], and an aliphatic diol. The content ratio of the monohydroxy compound is 0.1 to 20 mol% in the hydroxy component, and the intrinsic viscosity measured by an Ubbelohde viscometer at 30 ° C. using a dilute solution of orthochlorophenol is 0.4 or more and 2.0 or less. Aliphatic polyester. (In the formula, R ₁ represents an alkylene group, and n is 0 or 1.) HOOC- (CH ₂ ) m-COOH [II] (In the formula, m is an integer of 0 to 10) 2. A dihydroxy compound having a general formula represented by the following formula [III] as a main constituent component, and the content ratio of the hydroxy compound in which the monohydroxy compound and the dihydroxy compound are combined is within the entire hydroxy component. 0.1
The aliphatic polyester according to claim 1, which is -30 mol%. (In the formula, R ² and R ³ independently represent an alkylene group, and p is 3
Or 4, and q and r are independently 0 or 1. )