JP3236978B2 - UV absorbent-containing resin molded article and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a molded article made of a polyester resin in which a benzotriazole-based or benzophenone-based ultraviolet absorber is incorporated so as not to be volatilized and disappears, and the weather resistance is greatly improved. About the method.

[0002]

2. Description of the Related Art Polyester resins are excellent in strength and the like, but have a drawback of poor weather resistance. Therefore, when manufacturing a roofing material or other exterior building materials by melting and molding a polyester resin such as polycarbonate, an ultraviolet absorber is mixed into the resin to suppress deterioration of the resin due to ultraviolet rays and improve weather resistance. Is being planned.

[0003]

However, even if the conventionally used ultraviolet absorber is physically mixed into the polyester resin, the ultraviolet absorber does not chemically bond to the polymer molecules of the resin. There is a problem that the ultraviolet absorber is liable to volatilize and disappear during the melting and molding of the resin, and gradually volatilizes and disappears even after molding. For this reason, the conventional polyester resin molded article containing an ultraviolet absorber is still unsatisfactory in that weather resistance is maintained for a long period of time.

[0004] Under these circumstances, recently, research has been conducted on high-molecular-weight ultraviolet absorbers that are difficult to volatilize, and for example, ultraviolet absorbers made of a copolymer of a benzophenone-based compound and an acrylic monomer have been developed. However, such a high molecular weight ultraviolet absorber may have poor compatibility with the polyester resin, and when added to a polycarbonate resin or the like having a good transparency, a problem of a decrease in transparency or a problem of coloring occurs. There was a case.

The present invention has been made in view of the above-mentioned problems, and has as its object to minimize the volatilization and disappearance of an ultraviolet absorber, and to maintain the ultraviolet absorption ability for a long period of time. An object of the present invention is to provide an agent-containing polyester resin molded article and a method for producing the same.

[0006]

In order to achieve the above object, the resin molded article of the present invention is characterized in that a benzotriazole-based or benzophenone-based ultraviolet absorber undergoes a transesterification reaction with a polyester resin polymer molecule of the molded article. An ester bond, an unreacted ultraviolet absorber, and a molded article of a polyester resin containing an amine compound or a transition metal halide which is a transesterification catalyst,
The ultraviolet absorber is a derivative of a 2- (2'-hydroxyphenyl) benzotriazole derivative in which hydrogen attached to the carbon at the 4'-position of the hydroxyphenyl group is substituted with a functional group having a hydroxyl group, or A hydroxybenzophenone derivative wherein hydrogen attached to the carbon at position 4 of the benzene ring is substituted with a functional group having a hydroxyl group. Further, the production method of the present invention, before heating and melting the polyester-based resin into a predetermined shape, with a benzotriazole-based or benzophenone-based ultraviolet absorber, an amine-based compound or a transition metal as a transesterification catalyst. A method for producing a resin molded product, in which a halide is added and an ultraviolet absorber is subjected to a transesterification reaction with a polymer molecule of a polyester resin in a heat-melted state, wherein the ultraviolet absorber is 2- (2'-hydroxyphenyl) A benzotriazole derivative in which the hydrogen attached to the carbon at the 4'-position of the hydroxyphenyl group is substituted with a functional group having a hydroxyl group, or a hydrogen attached to the carbon at the 4-position of the benzene ring in a 2-hydroxybenzophenone derivative Is a derivative in which is substituted with a functional group having a hydroxyl group.

[0007] Preferably, as an ultraviolet absorber,
An ultraviolet absorbent in which the functional group having a hydroxyl group is -ROH (where R is any one of an alkylene chain, an alkylene oxide chain, and a polyalkylene oxide chain) is used.

[0008]

The benzotriazole-based or benzophenone-based ultraviolet absorber does not substantially cause a transesterification reaction when it is mixed with a polyester resin in a heat-melted state before molding, but a transesterification catalyst is added. Then, the benzotriazole-based ultraviolet absorber causes a transesterification reaction at an ester-bonded portion of the polymer molecule of the polyester-based resin, and is immobilized by ester-bonding. This transesterification reaction can be carried out by using 2- (2'-
(Hydroxyphenyl) benzotriazole derivatives in which the hydrogen attached to the carbon at the 4'-position of the hydroxyphenyl group is substituted with a functional group having a hydroxyl group, or 4-hydroxybenzophenone derivatives, When a derivative obtained by substituting a hydrogen attached to a carbon at a position with a functional group having a hydroxyl group is used, the reaction rate increases. Then, the unreacted ultraviolet absorber and the transesterification catalyst are mixed in a dispersed state between the polymer molecules.

As described above, when the benzotriazole-based or benzophenone-based ultraviolet absorber is ester-bonded to the polymer molecule of the polyester resin of the molded product, the ultraviolet absorber does not volatilize or disappear from the resin molded product. If the exchange catalyst is other than an amine compound or a transition metal halide, the reaction may be remarkably reduced, or the reaction may turn yellow. For example, when an alkali metal salt such as sodium methoxide is used as a transesterification catalyst, the reaction rate is high, but the ultraviolet absorber is affected by the alkali metal. The polyester resin molded product turns yellow. However, when an amine-based compound or a halide of a transition metal is used as a transesterification catalyst as in the present invention, it exhibits excellent ultraviolet absorbing ability for a long period of time without causing any of the above-mentioned disadvantages, and yellowing. And the weather resistance can be greatly improved.

[0010]

Embodiments of the present invention will be described below with reference to the drawings.

FIG. 1 is a schematic explanatory view showing one embodiment of the production method of the present invention, and illustrates a case where a plate-like molded product (resin plate) is produced by melt-extrusion molding a polyester resin. is there.

In FIG. 1, 1 is a melt extruder, 1a
Is a resin input hopper provided at the rear of the molding machine, 1b is a hopper provided in the middle of the molding machine, 1c is a screw incorporated in the molding machine, 1d is a molding die provided at the tip of the molding machine, and 2 is A pair of upper and lower cooling rolls, 3 is a conveyor belt, 4
Is a cutting machine.

According to this embodiment, the polyester resin 5 as a raw material dried by preheating is introduced into the molding machine 1 from the hopper 1a at the rear of the molding machine, and the polyester resin 5 is melted at a temperature higher than the melting temperature (excluding the decomposition temperature). The mixture is kneaded with the screw 1c while being heated and melted as described below. Then, a mixture 6 of a benzotriazole-based or benzophenone-based ultraviolet absorber and a transesterification catalyst is placed in a hopper 1 in the middle of a molding machine.
b), uniformly kneaded with the heated and melted polyester resin 5 with a screw 1c, and extruded into a plate shape from a mold 1d.

When the benzotriazole-based or benzophenone-based ultraviolet absorber and the transesterification catalyst are kneaded in this way, the ultraviolet absorber causes a transesterification reaction at the ester bond portion in the polymer molecule of the polyester resin 5, and the molecular end To form polymer molecules in which an ultraviolet absorber is ester-bonded. This transesterification reaction is performed in a state where the polyester resin 5 is molten.

A polyester resin molded product 50 extruded into a plate shape from the mold 1d is taken off while being cooled by a pair of upper and lower cooling rolls 2 and 2, and is conveyed to a cutting machine 4 by a conveyor belt 3. And cut to a predetermined length.

The ultraviolet absorbent-containing polyester resin plate (molded article) produced by the above method is immobilized by the ester bond of the benzotriazole- or benzophenone-based ultraviolet absorbent to the terminal of the polyester resin polymer molecule. Therefore, it does not volatilize and disappear from the resin plate over time.

As the polyester resin 5 as a raw material, a resin having a relatively high melting temperature and easily causing a transesterification reaction is suitable. For example, thermoplastic polyesters such as polycarbonate, polyethylene terephthalate, polybutylene terephthalate, polyarylate, and polycaprolactone are suitable. A series resin is used.

As the ultraviolet absorber, those having any one of a carboxyl group, a hydroxyl group and an amino group at the molecular terminal are used. In particular, benzotriazole having a molecular structure as shown in the following [Chemical Formula 1] is used. UV absorbers or benzophenone UV absorbers having a molecular structure as shown in the following [Chemical Formula 2] are preferably used.

Embedded image

Embedded image

That is, the ultraviolet absorber of Chemical Formula 1 is 2-
Of the (2'-hydroxyphenyl) benzotriazole derivatives, 3 ', 4', 5 ',
The hydrogen absorber of 6 ′ or the hydrogen of 3, 4, 5, or 6 of the benzene ring of the benzotriazole group is substituted with a functional group having a hydroxyl group —ROH. Of the 2-hydroxybenzophenone derivatives, 3, 4, 5, 6 hydrogens or 2 'of the benzene ring,
Any of 3 ', 4', 5 ', and 6' hydrogens is substituted with a hydroxyl group-containing functional group -ROH. The benzotriazole-based UV absorber or benzophenone-based UV absorber having such a molecular structure causes a transesterification reaction with the polyester resin polymer at a higher conversion rate than the UV absorbers having other molecular structures.

In particular, R in the functional group is an alkylene chain, an alkylene oxide chain or a polyalkylene oxide chain as exemplified in [Chemical Formula 1] and [Chemical Formula 2], and the functional group -RO
A benzotriazole-based ultraviolet absorber in which H is substituted with hydrogen attached to the carbon at the 4'-position of the hydroxyphenyl group, and a benzophenone-based ultraviolet absorber in which the functional group -ROH is substituted with hydrogen attached to the carbon at the 4-position of the benzene ring, Very preferably used. Specific examples of such a benzotriazole-based ultraviolet absorber include 2- (2'-hydroxy-4 '
-Hydroxyethoxyphenyl) benzotriazole,
2- (2'hydroxy-4'-hydroxymethoxyphenyl) benzotriazole and the like. Specific examples of the benzophenone-based ultraviolet absorber include 2-hydroxy-4
-Hydroxyethoxybenzophenone and the like.

In the present invention, in addition to the above, a benzotriazole-based or benzophenone-based ultraviolet absorber whose functional group is simply a hydroxyl group can be used.

The above-mentioned benzotriazole-based or benzophenone-based ultraviolet absorbers are added to the polyester resin alone or in an appropriate mixture. The amount of addition is 0.01 to 100 parts by weight of the polyester resin. ~ 1
Desirably, the ratio is 0.0 parts by weight. When the amount of the ultraviolet absorber added is less than 0.01 part by weight, the amount of the ultraviolet absorber contained and retained in the obtained resin molded product is small, so that it becomes difficult to impart excellent ultraviolet absorbing ability, Conversely, when the amount is more than 10.0 parts by weight, the molecular weight of the polymer is significantly reduced, and the commercial value is reduced.

On the other hand, it is necessary to use an amine compound or a halide of a transition metal as a transesterification catalyst, and other catalysts are not suitable for the present invention. When an amine compound or a halide of a transition metal is used as in the present invention, the transesterification reaction rate is increased to 80% or more as shown in the experimental data described later, and therefore, benzotriazole-based or benzophenone-based ultraviolet rays that are ester-bonded. As the amount of absorber increases, and these catalysts do not adversely affect the ultraviolet absorber, it is possible to maintain excellent ultraviolet absorption capacity over a long period of time, suppress yellowing and significantly improve weather resistance Becomes On the other hand, if another catalyst, for example, an alkali metal salt such as sodium methoxide is used, the transesterification reaction rate is high, but the ultraviolet absorber is hardly able to exhibit a sufficient ultraviolet absorbing ability under the influence of the alkali metal. Therefore, the polyester resin molded article is disadvantageously yellowed, which is not preferable.

Examples of the transition metal halide include tin chloride, zinc chloride, ferric chloride, and lead chloride.
Among them, ferric chloride having the highest transesterification rate is particularly preferably used. Examples of the amine compound include triethylamine and trimethylamine.
A secondary amine such as a secondary amine or dimethylamine is preferably used. These transesterification catalysts are used in an amount of 0.0005 to 0.5 with respect to 100 parts by weight of the polyester resin.
Suitably, it is added in a proportion of 5 parts by weight.

The transesterification reaction between the polyester resin and the benzotriazole or benzophenone ultraviolet absorber occurs when the polyester resin is heated to a temperature higher than the melting temperature and lower than the decomposition temperature to be in a molten state as described above. . Therefore, when a polycarbonate resin is used as the polyester resin, for example, about 2
What is necessary is just to heat to a temperature of 30 to 330 ° C. to melt. The time required for the transesterification reaction varies somewhat depending on the type of the ultraviolet absorber, the type of the polyester resin, and the like, but the reaction is almost completed in about 1 to 15 minutes. Therefore, when extruding a resin plate as in the above embodiment, a mixture 6 of an ultraviolet absorbent and a transesterification catalyst is charged into the molten polyester resin 5 in the molding machine 1 and kneaded for about 1 to 15 minutes. After that, it is necessary to set the position of the intermediate hopper 1b, the screw design and other extrusion conditions so that the resin is extruded from the die 1d at the tip, and to sufficiently perform the transesterification reaction. In that case, a twin-screw extruder or kneader is preferably used.

In the above embodiment, the polyester resin 5 is fed into the molding machine 1 from the hopper 1a, and the mixture 6 of the ultraviolet absorbent and the transesterification catalyst is fed into the molding machine 1 from the hopper 1b. The polyester resin 5 and the mixture 6 may be charged together, or the ultraviolet absorber and the catalyst may be charged separately.

Further, in the above-described embodiment, the molten polyester-based resin subjected to the transesterification reaction with the ultraviolet absorber was used in the mold 1
The resin plate is manufactured by extrusion molding in a single layer from d. Of course, extruded products of various shapes, such as sheets, films, odd-shaped products, etc. can be manufactured by changing the mold 1d, Using a co-extrusion molding machine or the like, the upper layer is made of a molten polyester resin having an ultraviolet absorber ester-bonded thereto, and the upper and lower layers are made of a molten polyester resin or another resin containing little or no ultraviolet absorber. Of course, it is also possible to produce a resin plate having a two-layer or three-layer structure in which a polyester resin layer containing an ultraviolet absorber is laminated on the surface by co-extrusion molding into layers or three layers.

Even in the case of injection molding, before the molten polyester resin is injected into the mold of the injection molding machine,
If a benzotriazole-based or benzophenone-based ultraviolet absorber and a transesterification catalyst are added and a transesterification reaction is performed, similarly, a resin molded product in which the ultraviolet absorber is less volatilized can be obtained.

Next, more specific examples of the present invention will be described.

Example 1 Polycarbonate was used as a polyester resin, and 2- (2'-hydroxy-4'-hydroxyethoxyphenyl) benzotriazole was used as an ultraviolet absorber in an amount of 1.0 part by weight, based on 100 parts by weight of the polycarbonate, and an ester. Dry blending was performed in advance with 0.001 part by weight of triethylamine as a replacement catalyst. This blend was put into an extruder and added to the extruder.
The mixture was heated and melted and kneaded at 0 ° C., transesterified for about 3 minutes, and extruded from a mold of a molding machine to obtain a film having a thickness of 0.1 mm. Then, a test piece (1) was prepared from this film.

With respect to this test piece (1), the quantitative ratio (reaction rate) of the ultraviolet absorber in an ester bond and the unabsorbed ultraviolet absorber was determined by the test method described below. It was found that the UV absorber had a transesterification reaction at a reaction rate of about 80%.

Further, the test piece (1) was subjected to an accelerated weather resistance test, and the relationship between the irradiation time, the residual ratio of the ultraviolet absorbent, and the degree of yellowing (ΔYI) was examined. The results are shown in Table 1 below. The accelerated weathering test was carried out using a xenon weatherometer (manufactured by Atlas) for 100 hours and 500 hours.
hr, 1000 hr irradiation accelerated test, ΔYI
Is a value obtained by measuring with a # 90 color measuring system (manufactured by Nippon Denshoku Co., Ltd.). Further, the residual ratio of the ultraviolet absorber was determined by using a visible-ultraviolet spectrophotometer UV-3100.
(Shimazu Seisakusho Co., Ltd.) was used to measure the UV absorbance of the test piece at each irradiation time, and the change in the absorbance of the maximum absorption wavelength of the UV absorber was calculated with the residual ratio at the irradiation time of 0 hr as 100. It is.

(Reaction rate test method)
This is performed using a C (gel permeation chromatography) device. UV absorber 2- (2 ′) used in Example 1
-Hydroxy-4'-hydroxyethoxyphenyl) benzotriazole has a maximum ultraviolet absorption wavelength (λmax),
325 nm. Therefore, the polycarbonate and the catalyst blended together with the ultraviolet absorber adjust the detection wavelength of the GPC ultraviolet detector to 325 nm which is not detected at the measurement sample concentration. For comparison with Example 1, as shown in Comparative Example 1 below, the UV absorber of Example 1 was melt-kneaded with polycarbonate at the same compounding ratio and extruded without adding a catalyst, and no transesterification reaction was performed. The film is used as a test piece (1 ') for comparison. This test piece (1 ')
The molecular weight distribution curve of GPC is as shown in FIG. 2, and the peak (a) of the ultraviolet absorbent appears on the low molecular weight side (right side of the horizontal axis). On the other hand, the molecular weight distribution curve of the GPC of the test piece (1) prepared in Example 1 is as shown in FIG. It appears at the same elution time as peak (a), but the detection intensity decreases, and the attenuated peak (b) appears shifted to peak (c) on the polymer side (left side on the horizontal axis). That is, when the ultraviolet absorber reacts with the terminal of the polycarbonate, the ultraviolet absorber has a high molecular weight and the peak shifts. (C) shows the peak of the reacted part, and (b) shows the peak of the unreacted part. The conversion is determined from the ratio of the sum of the areas of the peak (b) and the peak (c) to the area of the peak (c) in the molecular weight distribution curve. Next, the test piece (1) prepared in Example 1 was purified to remove the unreacted ultraviolet absorber, and the ultraviolet absorber was ester-bonded to the terminal by FT-IR, ¹ H-NMR, and ¹³ C-NMR. Make sure you are. From this, it can be confirmed that the peak (c) is not homopolymerization of only the ultraviolet absorber.

Example 2 Polycarbonate as a polyester resin and 2- (2'-hydroxy-4'-hydroxyethoxyphenyl) benzotriazole as an ultraviolet absorber in an amount of 1.0 part by weight based on 100 parts by weight of the polycarbonate, catalyst A test piece (2) was prepared in the same manner as in Example 1 except that dry blending was performed in advance with ferric chloride in a mixing ratio of 0.001 part by weight.

When the reaction rate of the ultraviolet absorber of this test piece (2) was determined by the above-described test method, it was found that the transesterification of the ultraviolet absorber occurred at a reaction rate of about 90%. Further, the test piece (2) was used in Example 1
An accelerated weather resistance test was performed in the same manner as in Example 1 to examine the relationship between the irradiation time and the residual ratio of the ultraviolet absorbent and the degree of yellowing (ΔYI). The results are shown in Table 1 below.

Example 3 Polycarbonate as a polyester resin and 2-hydroxy- as an ultraviolet absorber
The same procedure as in Example 1 was carried out except that the 4-hydroxyethoxybenzophenone was preliminarily dry-blended in a mixing ratio of 1.0 part by weight to 100 parts by weight of polycarbonate and 0.001 part by weight of ferric chloride as a catalyst. To prepare a test piece (3).

When the reaction rate of the ultraviolet absorbent of this test piece (3) was determined by the test method described above, it was found that the transesterification of the ultraviolet absorbent occurred at a reaction rate of about 90%. Further, the test piece (3) of Example 1 was used.
An accelerated weather resistance test was performed in the same manner as in Example 1 to examine the relationship between the irradiation time and the residual ratio of the ultraviolet absorbent and the degree of yellowing (ΔYI). The results are shown in Table 1 below.

Comparative Example 1 1.0 part by weight of an ultraviolet absorber 2- (2'-hydroxy-4'-hydroxyethoxyphenyl) benzotriazole was mixed with 100 parts by weight of polycarbonate, and a transesterification catalyst was not mixed. A test piece (1 ′) for comparison was prepared from a film having a thickness of 0.1 mm extruded in the above. And this test piece (1 ')
Was subjected to an accelerated weather resistance test in the same manner as in Example 1 to examine the relationship between the irradiation time, the residual ratio of the ultraviolet absorbent, and the yellowing degree (ΔYI). The results are shown in Table 1 below.

[Comparative Example 2] A 0.1 mm thick film extruded with 100 parts by weight of polycarbonate and 1.0 part by weight of an ultraviolet absorber 2-hydroxy-4hydroxyethoxybenzophenone was used as a test piece for comparison. (2 ') was prepared.

Then, an accelerated weathering test was performed on the test piece (2 ') in the same manner as in Example 1 to examine the relationship between the irradiation time, the residual ratio of the ultraviolet absorbent, and the degree of yellowing (ΔYI). The results are shown in Table 1 below.

[Comparative Example 3] Extrusion molding was conducted by mixing 1.0 part by weight of an ultraviolet absorber 2-hydroxy-4hydroxyethoxybenzophenone and 0.001 part by weight of sodium methoxide as an ultraviolet absorber with respect to 100 parts by weight of polycarbonate. A test piece (3 ') for comparison was prepared from the thus-formed film having a thickness of 0.1 mm.

With respect to this test piece (3 '), the reaction rate of the ultraviolet absorber was determined by the above-mentioned test method.
At the reaction rate, it was found that the ultraviolet absorber had undergone a transesterification reaction. Further, the test piece (3 ') was subjected to an accelerated weathering test in the same manner as in Example 1, and the relationship between the irradiation time, the residual ratio of the ultraviolet absorbent, and the degree of yellowing (ΔYI) was examined. The results are shown in Table 1 below.

[0043]

[Table 1]

It can be seen from Table 1 that a comparative test piece (1 ') containing only a benzotriazole-based UV absorber without using a transesterification catalyst and a comparative test piece containing only a benzophenone-based UV absorber. Test piece (2 ')
Is easy to volatilize over time because the ultraviolet absorber hardly forms an ester bond with the polycarbonate polymer molecule.
It can be seen that the residual ratio of the ultraviolet absorbent after irradiation for 000 hours is reduced to 69% or less, the deterioration of the test piece is advanced, and the yellowing degree is increased to 3.9 or more. On the other hand, the test pieces (1) and (2) of the present invention mixed with a benzotriazole-based ultraviolet absorber and a transesterification catalyst (triethylamine, ferric chloride), and a benzophenone-based ultraviolet absorber and a transesterification catalyst In the test piece (3) of the present invention containing (ferric chloride), most of the ultraviolet absorber is fixed by ester bonding with the polymer molecules of the polycarbonate, and the unreacted ultraviolet absorber volatilizes with time. Is only 100
The residual ratio of the ultraviolet absorbent after irradiation for 0 hours is as high as 93% or more, and the yellowing degree is as low as 2.1 or less, indicating that excellent weather resistance is maintained.

Also, a benzophenone-based ultraviolet absorber,
A comparative test piece (3 ') in which sodium methoxide, which is not so preferable as a transesterification catalyst, was mixed with an ultraviolet absorber to form an ester bond, had a high reaction rate of 80%, and the ultraviolet absorption after irradiation for 1,000 hours. The residual ratio of the agent is also 92.
%, But it is difficult for the UV absorber to exhibit sufficient UV absorption capacity under the influence of sodium methoxide.
The yellowing degree after irradiation for 1000 hours is relatively high at 2.9, which indicates that the test piece (3 ') is deteriorated to some extent.

As is clear from the above description and the test results, the resin molded product of the present invention is characterized in that the hydrogen attached to the carbon at the 4'-position of the hydroxyphenyl group in the 2- (2'-hydroxyphenyl) benzotriazole derivative. A benzotriazole-based ultraviolet absorber composed of a derivative substituted with a functional group having a hydroxyl group, or benzophenone composed of a derivative of a 2-hydroxybenzophenone derivative in which hydrogen attached to the carbon at position 4 of the benzene ring has been substituted with a functional group having a hydroxyl group Since the system-based ultraviolet absorber is immobilized by ester bonding with the polymer molecule of the polyester-based resin at a high reaction rate by the catalysis of an amine compound or a transition metal halide added as a transesterification catalyst, the Less volatilization over time, and the above catalyst has a bad effect on UV absorbers Since no decrease ultraviolet absorbing ability is given to maintain an excellent ultraviolet absorbing ability over a long period, a marked effect such weather resistance is greatly improved.

In the production method of the present invention, a conventional versatile molding machine is used, and a benzotriazole-based or benzophenone-based ultraviolet absorber and a specific transesterification catalyst are added before molding to form a polyester melt in a heated and molten state. The process can be carried out simply by adding the step of transesterification with the polymer molecules of the resin, so there is no need to newly install special molding machines and equipment, so it is economical and efficiently mass-produces molded products with excellent weather resistance. It has the effect of being able to.

[Brief description of the drawings]

FIG. 1 is a schematic explanatory view showing one embodiment of a manufacturing method of the present invention.

FIG. 2 is a molecular weight distribution curve of a test piece (1 ′) for comparison by GPC.

FIG. 3 is a molecular weight distribution curve of the test piece (1) by GPC.

[Explanation of symbols]

REFERENCE SIGNS LIST 1 Extruder 5 Polyester resin 6 Mixture of benzotriazole or benzophenone UV absorber and transesterification catalyst 50 Resin molded product

────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁷ Identification symbol FI C08L 67/00 C08L 67/00 // C08L 67:00 67:00 (56) References JP-A-4-103626 (JP, A JP-A-2-133460 (JP, A) JP-A-63-278927 (JP, A) JP-A-7-126404 (JP, A) JP-A-6-107805 (JP, A) JP-A-1- 201330 (JP, A) JP-A-49-99596 (JP, A) JP-A-60-51181 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C08J 5/00 C08G 63 / 00-63/91 C08L 67/00-87/08 CA (STN) REGISTRY (STN)

Claims (4)

(57) [Claims] 1. A benzotriazole-based or benzophenone-based ultraviolet absorber is transesterified with a polymer molecule of a polyester resin of a molded article to form an ester bond, and is reacted with an unreacted ultraviolet absorber and an amine as a transesterification catalyst. A molded article of a polyester resin containing a halide of a transition compound or a transition metal, wherein the ultraviolet absorber is a 4- (2′-hydroxyphenyl) benzotriazole derivative of a 4 ′ of a hydroxyphenyl group Or a derivative in which hydrogen attached to the carbon at the 4-position is substituted with a functional group having a hydroxyl group, or a derivative of a 2-hydroxybenzophenone derivative in which the hydrogen attached to the carbon at the 4-position of the benzene ring is substituted with a functional group having a hydroxyl group. A resin molded product characterized in that: 2. The functional group having a hydroxyl group is —ROH (where R is any one of an alkylene chain, an alkylene oxide chain and a polyalkylene oxide chain).
The resin molded product according to the above. 3. A benzotriazole-based or benzophenone-based ultraviolet absorber and an amine-based compound or a transition metal halide as a transesterification catalyst are added before heating and melting the polyester-based resin into a predetermined shape. A method for producing a resin molded product, comprising subjecting an ultraviolet absorbent to a transesterification reaction with a polymer molecule of a polyester resin in a heat-melted state, wherein the ultraviolet absorbent is a 2- (2'-hydroxyphenyl) benzotriazole derivative. Of these, a derivative in which the hydrogen attached to the carbon at the 4'-position of the hydroxyphenyl group is substituted with a functional group having a hydroxyl group, or a 2-hydroxybenzophenone derivative having the hydrogen attached to the carbon at the 4-position of the benzene ring having a hydroxyl group. A method for producing a resin molded product, which is a derivative substituted with a functional group. 4. The functional group having a hydroxyl group is —ROH (where R is any one of an alkylene chain, an alkylene oxide chain and a polyalkylene oxide chain).
The production method described in 1.