JP2003155374A - Ultraviolet light absorber for thermoplastic polymer - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an ultraviolet light absorber for a thermoplastic polymer, itself excellent in preservability and heat resistance, inherently having transparency and, even when added to or kneaded with polyethylene terephthalate or polycarbonate each requiring a high kneading temperature and a high molding temperature, providing a inherently transparent molding product. SOLUTION: This ultraviolet light absorber for a thermoplastic polymer is obtained by compounding, as a substantial component, a specified cyclic imino ester compound having 1×10<-1> -1×10<+3> ppm chloride ion concentration.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an ultraviolet absorber for thermoplastic polymers. Various molded products such as films and casings manufactured from thermoplastic polymers generally undergo deterioration of quality such as discoloration and fading and strength deterioration due to exposure to ultraviolet rays. In order to prevent such deterioration in quality, a wide variety of ultraviolet absorbers are used in thermoplastic polymers and their molded products. Such an ultraviolet absorber has excellent preservability in relation to the fact that it is stored for a long time until use, and in particular, when it is added to and kneaded with a thermoplastic polymer, it itself has a heat resistance. It is required to have excellent properties and not to deteriorate the original characteristics of the thermoplastic polymer such as transparency. The present invention relates to an ultraviolet absorber for thermoplastic polymers that meets such requirements.

[0002]

2. Description of the Related Art Conventionally, benzophenone type ultraviolet absorbers, benzotriazole type ultraviolet absorbers, salicylic acid compound type ultraviolet absorbers and the like have been generally used as ultraviolet absorbers for thermoplastic polymers. However, these ultraviolet absorbers generally have a problem that they are inferior in heat resistance. Therefore, conventionally, a cyclic iminoester compound has been proposed as an ultraviolet absorber for improving such problems (Japanese Patent Publication Nos. 62-5944 and 62-31027).
However, although this ultraviolet absorber itself has excellent heat resistance, it is inferior in storability, and when it is added to and kneaded with a thermoplastic polymer such as polyethylene terephthalate or polycarbonate, the heat There is a problem that the original properties of the plastic polymer, such as transparency, are reduced.

[0003]

The problem to be solved by the present invention is that it has excellent storage stability and heat resistance, and that even if it is used by adding and kneading it to a thermoplastic polymer, There is an object of providing an ultraviolet absorber for a thermoplastic polymer, which is capable of obtaining a molded article having the original characteristics of the polymer, for example, transparency.

[0004]

However, the present inventors have
As a result of research to solve the above-mentioned problems, it was found that a compound prepared by using a specific cyclic iminoester compound as a substantial component and having a chloride ion concentration within a predetermined range is correct and suitable.

That is, the present invention was prepared so that the cyclic iminoester compound represented by the following formula 1 was a substantial component and the chloride ion concentration was in the range of 1 × 10 ⁻¹ to 1 × 10 ³ ppm. It relates to an ultraviolet absorber for a thermoplastic polymer, which is characterized by comprising

[0006]

[Formula 1]

The ultraviolet absorber for thermoplastic polymers of the present invention is a cyclic iminoester compound represented by the formula (1)
(A cyclic iminoester compound) as a substantial component, and has a chloride ion concentration of 1 × 10 ⁻¹ to 1 × 10 ³ p.
It was prepared to be in the pm range. Here, the chlorine ion concentration means a value measured by the mercury thiocyanate color development method.

The present invention does not particularly limit the method for preparing the ultraviolet absorbent for thermoplastic polymers of the present invention,
For this purpose, for example, 1) a step of producing a cyclic iminoester compound in which the chlorine ion concentration of the product is kept within a predetermined range in conjunction with the production, and 2) formation of a chlorine ion in the cyclic iminoester compound. Add chloride,
Examples of the method include controlling the chlorine ion concentration within a predetermined range, and the method 1) is preferable from the viewpoint of manufacturing cost.

In the process of producing a cyclic iminoester compound, there are the following methods 1) and 2) for keeping the chloride ion concentration of the product within a predetermined range in conjunction with the production thereof. The method of 1) is a method of producing a cyclic iminoester compound through an amidation reaction of anthranilic acid and terephthalic acid dichloride, and the method of 2) is a method of producing a cyclic iminoester compound with isatoic anhydride and terephthalic acid dichloride. This is a method for producing via an imino esterification reaction. 1) First, two molecules of anthranilic acid and one molecule of terephthalic acid dichloride were subjected to an amidation reaction in the presence of a solvent and an alkali, and a solid content containing the produced N, N'-bis (o-carboxyphenyl terephthalamide) was separated. After that, it is washed with water and dried. Next, N, N'-bis (o-carboxyphenyl terephthalamide) in the dried solid content and a dehydrating agent are subjected to an imino esterification reaction in the presence of a solvent to obtain a solid content containing the produced cyclic imino ester compound. To separate. Finally, the separated solid content is prepared so as to have a chlorine ion concentration within a predetermined range by a combined treatment of an alkali treatment and a water washing treatment. 2) First, 2 molecules of isatoic anhydride and 1 molecule of terephthalic acid dichloride are subjected to an imino esterification reaction in the presence of a solvent and an alkali to separate a solid content containing the produced cyclic imino ester compound.
Next, the separated solid content is prepared so as to have a chlorine ion concentration within a predetermined range by a combined treatment of an alkali treatment and a water washing treatment. In both of the method 1) and the method 2) described above, the main part is that the solid content containing the cyclic iminoester compound is adjusted to a chloride ion concentration within a predetermined range by a combined treatment of an alkali treatment and a water washing treatment. It is in the process of being prepared.

The combination of the alkali treatment and the water washing treatment for the solid content containing the cyclic iminoester compound includes 1) a method of treating the solid content containing the cyclic iminoester compound with an alkaline solution, and then a water washing treatment, 2)
Examples include a method in which a solid content containing a cyclic iminoester compound is treated with an alkaline solution and then washed with water, which is repeated.

The combined treatment of the alkali treatment and the water washing treatment on the solid content containing the cyclic iminoester compound will be described more specifically. Solid matter containing a cyclic iminoester compound, separated by using a filter such as a Nutsche filter, an Oliver filter or a filter press, or a centrifuge such as a basket centrifuge or a decanter centrifuge, water, acetone An aqueous organic solvent such as methanol or methanol, or a mixed solvent thereof is added so that the solid content concentration becomes 20 to 30% by weight to obtain a slurry. Then, first, in order to facilitate the removal of chlorine ions in the subsequent water washing treatment, a required amount of alkali is added, and the mixture is stirred at 10 to 40 ° C. for 1 to 2 hours for alkali treatment. Next, after separating the solid content containing the cyclic iminoester compound from the alkali-treated slurry, the separated solid content is washed with water.

The alkali used in the alkali treatment is not particularly limited, and examples thereof include 1) sodium methoxide,
Alkali metal alkoxides such as sodium ethoxide and potassium methoxide 2) Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide 3) Alkali metal carbonates such as sodium carbonate and potassium carbonate 4)
Examples thereof include hydrogencarbonates of alkali metals such as sodium hydrogencarbonate and potassium hydrogencarbonate, 5) ammonia water, and 6) lower alkyl quaternary ammonium hydroxides such as tetramethylammonium hydroxide and tetraethylammonium hydroxide. Of these, inorganic alkali metal salts such as sodium hydroxide and sodium carbonate are preferable.

The conditions for washing treatment are not particularly limited, but the amount of water used is preferably 3 to 20 times, more preferably 5 to 10 times, the weight of the solid content. The water temperature is preferably 20 to 80 ° C.

As described above, the combination of the alkali treatment and the water washing treatment is performed on the solid content containing the cyclic iminoester compound. After the water washing treatment, the solid content is separated and dried to measure the chloride ion concentration. Then, confirm that the chloride ion concentration is within the predetermined range. When the chlorine ion concentration is high, the above-mentioned combination treatment is repeated.

Thus, the ultraviolet absorber for thermoplastic polymer of the present invention is obtained. The ultraviolet absorbent for a thermoplastic polymer of the present invention is prepared by using a cyclic iminoester compound as a main component and a chloride ion concentration within a range of 1 × 10 ⁻¹ to 1 × 10 ³ ppm. However, it is preferable that the cyclic iminoester compound is contained in the range of 99.5% by weight or more and less than 100% by weight, and 99.9% by weight or more and 10% by weight or more.
It is more preferable that the content is within the range of less than 0% by weight.
In addition, the chlorine ion concentration is 1.5 × 10 ^{−1 to} 5 × 10 ² p
What was prepared so that it might be in the range of pm is preferable.

The thermoplastic polymer to which the ultraviolet absorber for thermoplastic polymers of the present invention is applied is not particularly limited, and examples thereof include 1) thermoplastic polyesters such as polyethylene terephthalate, polyethylene naphthalate and polybutylene terephthalate; 2) polycarbonate, 3) polystyrene, styrene-acrylonitrile-butadiene copolymer, styrene polymers such as high-impact polystyrene,
4) acrylic polymer, 5) amide polymer, 6) polyphenylene ether, 7) polyethylene, polypropylene,
Polyolefin such as polyvinyl chloride, 8) polyoxymethylene, 9) polyphenylene sulfide, 10) lactic acid polymer, and 11) any mixture of these thermoplastic polymers can be mentioned. Among them, the ultraviolet absorber for thermoplastic polymer of the present invention has a high degree of transparency, and requires a high kneading temperature and molding temperature, polyethylene terephthalate, when adding and kneading to polycarbonate, Highly effective. The ultraviolet absorber for thermoplastic polymer according to the present invention is excellent in storage stability and heat resistance itself,
Even when polyethylene terephthalate or polycarbonate, which is inherently transparent and requires high kneading temperature and molding temperature, is added and kneaded, a molded article having the inherent transparency can be obtained. is there.

The amount of the ultraviolet absorber for thermoplastic polymer of the present invention used with respect to the thermoplastic polymer is not particularly limited,
When adding it to a thermoplastic polymer and kneading it,
The ratio is 0.1 to 5 parts by weight per 100 parts by weight of the thermoplastic polymer.

[0018]

BEST MODE FOR CARRYING OUT THE INVENTION Embodiments of the ultraviolet absorbent for thermoplastic polymers of the present invention include the following 1) to 4). 1) An ultraviolet absorber for a thermoplastic polymer, which comprises 99.99% by weight of a cyclic iminoester compound and has a chloride ion concentration adjusted to 1.5 × 10 ⁻¹ ppm.

2) The cyclic imino ester compound is 99.9.
9% by weight and chloride ion concentration of 2 × 10 ⁻¹ p
An ultraviolet absorber for thermoplastic polymers, which is prepared to pm.

3) The cyclic imino ester compound is 99.9.
Contains 0% by weight and has a chlorine ion concentration of 4 × 10 ² pp
An ultraviolet absorber for a thermoplastic polymer, which is prepared in m.

4) The cyclic imino ester compound is 99.9.
Contains 4% by weight and has a chloride ion concentration of 9.5 × 10 ^2.
An ultraviolet absorber for a thermoplastic polymer, which is prepared to ppm.

Examples will be given below to make the constitution and effects of the ultraviolet absorbent for thermoplastic polymers of the present invention more concrete, but the present invention is not limited to these examples. . In the following Examples and Comparative Examples, “part” means “part by weight” and “%” means “% by weight”.

[0023]

[Examples] Test Category 1 (Preparation of UV absorber for thermoplastic polymer) -Example 1 First, 13.7 g of anthranilic acid was placed in a four-necked flask equipped with a thermometer, a stirrer, a reflux condenser and a dropping funnel.
(0.1 mol), 5.19 g of anhydrous sodium carbonate (0.
049 mol) and 100 ml of water were added, and the mixture was stirred for 10 minutes to dissolve. Into this four-necked flask, 10.2 g (0.05 mol) of terephthalic acid dichloride was added 300 ml of acetone.
The solution dissolved in was added dropwise at room temperature over 1 hour using a dropping funnel, and then subjected to an amidation reaction for 1 hour under reflux,
A solid content slurry containing N, N'-bis (o-carboxyphenyl terephthalamide) was obtained. The solid content was separated from this slurry by filtration, washed with 300 ml of water and dried to obtain 19.7 g of solid content. Next, dry solids 1
9.7 g, acetic anhydride 102 g (1 mol) and toluene 1
00 ml was placed in a four-necked flask, iminoesterification reaction was carried out under reflux for 6 hours, and after cooling to room temperature, solid content was separated by filtration. The filtered solid matter was washed with 100 ml of acetone and then dried to obtain 17.2 g of a solid matter containing a cyclic iminoester compound. Finally, 17 g of this solid content and 6 parts of water
8 g was placed in a flask, 2.42 g of 1% sodium hydroxide aqueous solution was added under stirring, and the mixture was stirred at 25 ° C. for 30 minutes for alkali treatment. The alkali-treated solids are filtered off,
It was washed with 160 g of warm water at 60 ° C. The solid content washed with water was dried for 2 hours with a hot air dryer at 100 ° C. to obtain 16.7 g of a slightly yellow powder. When this slightly yellow powder was analyzed, it contained 99.99% of a cyclic iminoester compound and had a chloride ion concentration of 1.5 × 10 ⁻¹ ppm. This was designated as a UV absorber for thermoplastic polymer (P-1).

The chlorine ion concentration was measured by the mercury thiocyanate color development method as follows. To an Erlenmeyer flask, 10.0 g of the ultraviolet absorber for thermoplastic polymer (P-1) is precisely weighed, and 10 ml of ion-exchanged water is added. An air-cooled tube is attached to this Erlenmeyer flask and heated at 90 ° C. for 1 hour while occasionally shaking. After cooling to room temperature, it is filtered to obtain a filtrate. Collect 10 ml of the filtrate in a test tube, add 2 ml of the following ferric nitrate-nitric acid solution and 1 ml of the following mercuric thiocyanate solution, and shake. 1 after adding the mercuric thiocyanate solution
After 0 minutes, the absorbance at 460 nm is measured with a spectrophotometer. Separately, a calibration curve is prepared using a standard solution of reagent grade sodium chloride, and the concentration of chloride ion contained in the ultraviolet absorber for thermoplastic polymer (P-1) is determined from this calibration curve.・ Ferric nitrate-nitric acid solution: 200 g of ferric nitrate dissolved in 500 ml of 5N nitric acid Mercury thiocyanate solution: 1 g of mercuric thiocyanate
Dissolved in 250 ml of methyl alcohol

Example 2 First, in a four-neck flask similar to that of Example 1, 13.7 g (0.1 mol) of anthranilic acid and 7.74 g of pyridine were added.
(0.098 mol) and 200 ml of acetone were added and 10
It was dissolved by stirring for a minute. A solution prepared by dissolving 10.2 g (0.05 mol) of terephthalic acid dichloride in 100 ml of acetone was added dropwise to the four-necked flask at room temperature over 1 hour by using a dropping funnel, and then amide was refluxed for 1 hour. The solidification reaction was performed to obtain a slurry of solid content containing N, N′-bis (o-carboxyphenyl terephthalamide). The solid content was separated from this slurry by filtration, washed with 300 ml of water, and then dried to obtain a solid content of 17.8 g. Next, 17.8 g of dried solid matter, 102 g (1 mol) of acetic anhydride and 100 ml of toluene were placed in a four-necked flask, and the mixture was refluxed at 6
After iminoesterification reaction for a period of time and cooling to room temperature,
The solid content was filtered off. The solid content filtered off is 100 ml of acetone.
After that, it was dried and dried to obtain 14.7 g of a solid content containing the cyclic imino ester compound. Finally, this solids 14
g and 68 g of methanol are put in a flask and stirred,
1.71 g of 1% sodium methoxide methanol solution
Was added, and the mixture was stirred at 25 ° C. for 30 minutes for alkali treatment.
Alkali-treated solids are filtered off, and warm water at 40 ° C 140
It was washed with water. The solid content washed with water was dried for 2 hours with a hot air dryer at 100 ° C. to obtain 13.6 g of a slightly yellow powder. Analysis of this slightly yellow powder revealed that it contained 99.99% of a cyclic iminoester compound and had a chloride ion concentration of 2 × 10 ⁻¹ ppm. This was designated as a UV absorber for thermoplastic polymer (P-2).

Example 3 First, in a four-necked flask similar to that of Example 1, 16.3 g (0.1 mol) of isatoic anhydride and 7.74 g of pyridine were prepared.
(0.098 mol) and 200 ml of acetone were added and 10
It was dissolved by stirring for a minute. A solution prepared by dissolving 10.2 g (0.05 mol) of terephthalic acid dichloride in 100 ml of acetone was added dropwise to the four-necked flask at room temperature over 1 hour by using a dropping funnel, and then imino was refluxed for 1 hour. The esterification reaction was performed to obtain a slurry of solid content containing the cyclic imino ester compound. The solid content containing the cyclic iminoester compound was separated from this slurry by filtration, washed with 300 ml of water and dried to obtain 16.0 g of solid content. next,
Add 15 g of dried solids and 48 g of water to the flask,
Under stirring, 4.24 g of a 1% sodium carbonate aqueous solution was added, and the mixture was stirred at 30 ° C. for 30 minutes for alkali treatment. The alkali-treated solid was filtered off and washed with 100 g of warm water at 60 ° C. The water-washed solid was dried for 2 hours with a hot air dryer at 100 ° C. to obtain 14.7 g of a slightly yellow powder.
Analysis of this slightly yellow powder revealed that it contained 99.90% of a cyclic iminoester compound and had a chloride ion concentration of 4 × 10 ² ppm. This was used as a UV absorber for thermoplastic polymer (P-3).

Example 4 First, in the same four-necked flask as in Example 1, 13.7 g (0.1 mol) of anthranilic acid and 5.3 potassium hydroxide were added.
2 g (0.095 mol) and 100 ml of water were added, and the mixture was stirred for 10 minutes and dissolved. A solution prepared by dissolving 10.2 g (0.05 mol) of terephthalic acid dichloride in 200 ml of acetone was added dropwise to this four-necked flask at room temperature over 1 hour using a dropping funnel, and then under reflux for 1 hour. The solidification reaction was performed to obtain a slurry of solid content containing N, N′-bis (o-carboxyphenyl terephthalamide). The solid content was separated from this slurry by filtration, washed with 300 ml of water and dried to obtain 19.7 g of solid content. Next, 19.7 g of dried solid matter, 102 g (1 mol) of acetic anhydride and 100 ml of toluene were placed in a four-necked flask, and the mixture was refluxed for 6 times.
After iminoesterification reaction for a period of time and cooling to room temperature,
The solid content was filtered off. The solid content filtered off is 100 ml of acetone.
After being washed with, and dried, 15.3 g of a solid content containing a cyclic iminoester compound was obtained. Finally, this solids 15
g and 35 g of water were placed in a flask, 7.46 g of a 1% potassium hydroxide aqueous solution was added with stirring, and the mixture was stirred at 25 ° C. for 30 minutes for alkali treatment. The alkali-treated solid was filtered off and washed with 160 g of warm water at 60 ° C. The solid content washed with water was dried with a hot air dryer at 100 ° C. for 2 hours to obtain 14.5 g of a slightly yellow powder. Analysis of this slightly yellow powder revealed that the cyclic iminoester compound was 99.94.
%, The chlorine ion concentration is 9.5 × 10 ² pp
It was m. This is a UV absorber for thermoplastic polymers (P
-4).

Comparative Example 1 The ultraviolet absorber for thermoplastic polymer (P
-1) 10 g and 1000 ml of ^{1x10 -2} % sodium hydroxide aqueous solution were put into a beaker and stirred with a homomixer for 1 hour, and then the solid content was separated by filtration. The filtered solid content and 1000 ml of water were placed in a beaker and further stirred with a homomixer for 1 hour, and then the solid content was filtered off. The above operation is 3 in total
The solid content separated by filtration was dried repeatedly at 100 ° C. for 1 hour to obtain a pale yellow powder. Analysis of this slightly yellow powder revealed that the cyclic imino ester compound was 100.00
%, Chlorine ion concentration is 5 × 10 ^-2 ppm
Met. This is a UV absorber for thermoplastic polymers (R-
1).

Comparative Example 2 17.0 g of a pale yellow powder was obtained in the same manner as in Example 1 except that the alkali treatment was not carried out. Analysis of this slightly yellow powder revealed that the cyclic iminoester compound was 98.7.
Contains 9%, chloride ion concentration is 2 × 10 ³ ppm
Met. This is a UV absorber for thermoplastic polymers (R-
2).

Test Category 2 (Evaluation of UV Absorbing Capacity and Preservability of UV Absorbing Agent for Thermoplastic Polymer) ・ UV absorbing agent for thermoplastic polymer (1.0 mg) prepared in UV absorbing capacity test category 1 Dissolved in 200 ml of 1,1,2,2-tetrachloroethane, and the transmittance at 350 nm was measured using a spectrophotometer (Spectrophotometer U-2000 manufactured by Hitachi, Ltd.) and evaluated according to the following criteria. did. The results are summarized in Table 1. Evaluation criteria ⊚: Transmittance is less than 25% ○: Transmittance is 25% or more and less than 26% Δ: Transmittance is 26% or more

・ Ultraviolet absorbent 1 for thermoplastic polymer prepared in storage stability test category 1
0 g was put in a petri dish and stored in a thermo-hygrostat having a temperature of 40 ° C. and a humidity of 50% for 6 months. The acid value of the ultraviolet absorber for thermoplastic polymer before and after storage was measured, and the increased acid value was evaluated according to the following criteria. Evaluation criteria ⊚: Increased acid value is less than 1 × 10 ⁻² ◯: Increased acid value is 1 × 10 ⁻² or more and less than 1 × 10 ⁻¹ Δ: Increased acid value is 1 × 10 ⁻¹ or more and less than 1 × : Increased acid value is 1 or more

Test Category 3 (Evaluation when Adding and Kneading UV Absorbent for Thermoplastic Polymer to Polyethylene Terephthalate) Polyethylene terephthalate having an intrinsic viscosity of 0.70 for the UV absorber for thermoplastic polymer prepared in Test Category 1 The heat resistance and transparency when added and kneaded to were evaluated by the following methods. The results are summarized in Table 1.

100 parts of heat-resistant polyethylene terephthalate chip and 2 parts of UV absorber for thermoplastic polymer prepared in test section 1 were dry blended and 280 using a biaxial extruder.
While kneading at ℃, melt-extruded, water-cooled into pellets, vacuum dried, put 10 g of vacuum dried pellets into a test tube, and heat and melt in an oven at 300 ℃ for 10 minutes (B) , Melted by heating for 60 minutes (T)
And prepared. Both appearances were visually observed and evaluated according to the following criteria. Evaluation Criteria A: There is no difference between B and T, and no abnormality such as burning is observed on T. Δ: T is slightly yellowed compared to B, but T has no abnormality such as burning. X: T is clearly yellowed more than B, and a part of T is burnt.

Dry blend of 100 parts of transparent polyethylene terephthalate chip and 2 parts of UV absorber for thermoplastic polymer prepared in test section 1 and 280 using a biaxial extruder
While kneading at ℃, melt extruded from T die, about 50 ℃
It was cooled with a cooling roll of No. 1 to produce an amorphous sheet having a thickness of about 1 mm. Separately, a sheet prepared in the same manner without blending the ultraviolet absorber for thermoplastic polymer was used as a blank and evaluated according to the following criteria. Evaluation Criteria ⊚: Has transparency equivalent to blank. ◯: It is slightly clouded compared to the blank. Δ: Slightly cloudy compared with the blank. X: Clearly cloudy compared with the blank.

Test Category 4 (Evaluation when UV Absorbent for Thermoplastic Polymer is Added and Kneaded in Polycarbonate) The UV absorber for thermoplastic polymer prepared in Test Category 1 was used as a polycarbonate chip (a product manufactured by Teijin Chemicals Ltd. The heat resistance and transparency when added to and kneaded with (Panlite) were evaluated by the following methods. The results are summarized in Table 1.

100 parts of heat-resistant polycarbonate chips and 2 parts of UV absorber for thermoplastic polymer prepared in test section 1 are dry blended and melt-extruded while kneading at 290 ° C. using a twin-screw extruder. After cooling with water and making pellets,
It was vacuum dried at 100 ° C. for 5 hours. Then, in the following, evaluation was performed in the same manner as in Test Category 3.

Dry blend of 100 parts of transparent polycarbonate chip and 2 parts of UV absorber for thermoplastic polymer prepared in Test Category 1, and kneading at 290 ° C. using a twin-screw extruder and melting from T-die It was extruded and cooled with a cooling roll at about 50 ° C. to prepare a sheet having a thickness of about 1 mm. Then, in the following, evaluation was performed in the same manner as in Test Category 3.

[0038]

[Table 1]

In Table 1, content: content of cyclic iminoester compound in ultraviolet absorber for thermoplastic polymer (%) PET: polyethylene terephthalate PC: polycarbonate

As is clear from the results shown in Table 1, each of the ultraviolet absorbers for thermoplastic polymers of Examples 1 to 4 was
It satisfies all of UV absorption, storability, heat resistance and transparency. Among them, Examples 1 to 3 in which the content of the cyclic iminoester compound is 99.9% by weight or more and less than 100% by weight and the chloride ion concentration is in the range of 1.5 × 10 ^{−1 to} 5 × 10 ² ppm. The above-mentioned UV absorbers for thermoplastic polymers are excellent. On the other hand, the ultraviolet absorber for thermoplastic polymers of Comparative Example 1 is substantially pure cyclic iminoester compound containing almost no chlorine ions, but has poor storage stability and transparency. Further, the ultraviolet absorbent for thermoplastic polymers of Comparative Example 2 contains a large amount of chloride ions, and therefore, the content of the cyclic iminoester compound is so low that the ultraviolet absorbent is poor in the first place, and the heat resistance and Poor transparency.

[0041]

Industrial Applicability As is apparent from the above, the present invention described above is a polyethylene which itself has excellent storage stability and heat resistance, is inherently transparent, and requires high kneading and molding temperatures. Even when it is added to and kneaded with terephthalate or polycarbonate, there is an effect that a molded article having its original transparency can be obtained.

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Tetsuo Ichihashi             3-37-19 Oyama, Sagamihara City, Kanagawa Prefecture             People DuPont Films Co., Ltd. Sagamihara Research Center             In the center F term (reference) 4J002 AA011 BB031 BB121 BC031                       BD031 BG041 BN151 CB001                       CF061 CF071 CF081 CG001                       CH071 CL001 CN011 EU236                       FD056

Claims (8)

[Claims] 1. A cyclic iminoester compound represented by the following formula 1 as a substantial component and a chloride ion concentration of 1 ×.
An ultraviolet absorber for a thermoplastic polymer, which is prepared so as to be in the range of 10 ⁻¹ to 1 × 10 ³ ppm. [Formula 1] 2. The ultraviolet absorber for a thermoplastic polymer according to claim 1, which contains the cyclic iminoester compound represented by the formula 1 in the range of 99.5% by weight or more and less than 100% by weight. 3. The ultraviolet absorber for a thermoplastic polymer according to claim 1, which contains the cyclic iminoester compound represented by the formula 1 in a range of 99.9% by weight or more and less than 100% by weight. 4. The chlorine ion concentration is 1.5 × 10 ^{−1 to} 5
The ultraviolet absorber for thermoplastic polymers according to any one of claims 1 to 3, which is prepared so as to be in a range of x10 ² ppm. 5. The high thermoplasticity according to claim 1, wherein the cyclic iminoester compound represented by the formula 1 is obtained through an amidation reaction of anthranilic acid and terephthalic acid dichloride. UV absorber for molecules. 6. The cyclic iminoester compound represented by formula 1 is obtained through an iminoesterification reaction between isatoic anhydride and terephthalic acid dichloride.
4. The ultraviolet absorber for thermoplastic polymer according to any one of items 4 to 4. 7. The ultraviolet absorber for a thermoplastic polymer according to claim 1, which is for polyethylene terephthalate. 8. The ultraviolet absorber for thermoplastic polymers according to claim 1, which is used for polycarbonate.