KR100517066B1 - Method for manufacturing polypropylene resin containing photochromic compound - Google Patents

Abstract

According to the present invention, the photochromic compound is evenly infiltrated, and it is possible to produce a high performance excellent photochromic polypropylene molding with a small amount of the photochromic compound and to produce a photochromic polypropylene yarn of various thicknesses. It relates to a polypropylene resin that can be produced and a method for producing the same.

Description

The polypropylene resin containing a photochromic compound and the manufacturing method of polypropylene company {Method for manufacturing polypropylene resin containing photochromic compound}

The present invention relates to a method for producing a resin containing a photochromic compound, and more particularly, to a polypropylene resin suitable for producing moldings and polypropylene yarns containing a photochromic compound and a photochromic compound prepared therefrom. Polypropylene moldings and polypropylene yarns.

Photochromic refers to a property that discolors due to the action of light (ultraviolet rays) and returns to its original color in a room (where ultraviolet rays are blocked). A photochromic compound is a reversible change in chemical structure caused by ultraviolet rays. , Refers to a compound whose color changes from colorless to colored or from colored to other colored. When the ultraviolet light is irradiated to the photochromic compound in the solution or solid state, the color is changed due to the change of absorption wavelength due to the change of chemical structure, but when the ultraviolet light is blocked, the photochromic phenomenon is returned to the original color again.

That is, the photochromic compound is present in a double bottom state in which it absorbs ultraviolet rays strongly and absorbs visible light strongly. It causes phosphorus color change. As such a photochromic compound, inorganic compounds include silver halides, Hg ₃ , S ₂ , I ₂ , and the like, and organic compounds include those obtained by isomerization of a double bond (azobenzene, dioindigo, etc.) and hydrogen transfer depending on the reaction mode. By tautomerism (salicylicen analiline, etc.), by pericyclic reactions (prigid, etc.), by ring reactions (such as anthracene), by binding ions (triphenylmethane, Spiropyran etc.) etc. are mentioned as an example.

As the photochromic compound already known and widely used, a benzopyran compound (Patent Application No. 98-018556), a naphthopyran system (Patent Publication 99-017042), a spiroxazine compound, a spiropyran compound (Patent Application No. 90-701930).

Until now, such photochromic compounds have been mainly used in the manufacture of glass such as automobiles, buildings, sun glasses, plastic lenses, and the like. For example, Patent Publication No. 94-07779 includes organic photochromic materials. Plastic matrices such as photochromic ophthalmic lenses and automotive roof skylights are described.

In recent years, cosmetics and manicures focused on the photochromic properties of photochromic compounds and cosmetic products such as manicures (Patent Application No. 99-06813) and coating agents (Patent Application Nos. 99-06814 and 99-048421), etc. The use of is expanding.

In the production of a product using such a photochromic compound, a method of incorporating a photochromic compound in a raw material component or dissolving these compounds together with a polymer in a solvent and then forming a coating, a film or the like or using a method for producing a molded article . For example, Patent Application No. 2001-1402 discloses a photochromic accessory accessory coating / printing agent composition, and Patent Publication No. 2001-84405 discloses a photochromic resin molding using a spiropyran type photochromic compound. Doing. In addition, Patent Application No. 2001-29435 discloses a method for producing a master batch of a photochromic resin molding.

However, in the case of the photochromic film or molded article produced by these methods, there is a problem that the coating layer of the molded article is easily peeled off, or the photochromic compound particles are detached, and thus, various other fields are required for a better and smoother uniform coating layer. There have been many limitations on the use, such as not being used. In addition, some mixed organic solvents used to make the photochromic resin may destroy the molecular structure of the photochromic compound used, leading to a decrease in the durability of the photochromic compound, and the photochromic compound may not be uniformly mixed with the resin. There was this.

First of all, the molded product can be manufactured using a resin containing a conventional photochromic compound, but in the manufacture of a fiber (filament yarn) requiring spinning to a fine thickness, the spinneret is blocked by the photochromic compound, Due to problems such as the frequent occurrence of yarn during spinning, spinning for fiber manufacturing was almost impossible. Therefore, when the photochromic compound is conventionally applied to a fabric or the like, the fabric itself is often painted or printed with dyes and coatings containing the photochromic compound on the fabric rather than causing the photochromic phenomenon.

Accordingly, the present invention is to solve the above problems, an object of the present invention by using a polypropylene resin that is widely used in a variety of applications, excellent photochromic properties of a uniform concentration in which the photochromic compound is not separated or detached from the resin It is to provide a polypropylene resin having and a method for producing the same.

Still another object of the present invention is to provide a high-quality molded article by using such a photochromic polypropylene resin, as well as a polypropylene resin capable of spinning a photochromic polypropylene yarn without clogging a spinneret or breaking a fiber. It is to provide a method for producing the same and a photochromic polypropylene yarn prepared therefrom.

According to the present invention, the photochromic compound is uniformly infiltrated and has a uniform concentration, and it is possible to produce a high performance excellent photochromic polypropylene molded product with a small amount of photochromic compound, and to produce a photochromic polypropylene yarn of various thicknesses. It relates to a polypropylene resin that can be produced and a method for producing the same.

The present invention comprises dissolving a photochromic compound in a mixed organic solution containing toluene, methyl ethyl ketone and normal hexane, and then reacting by adding a polypropylene resin to the mixed solution, and drying the reacted polypropylene resin. Characterized by a method for producing a photochromic polypropylene resin comprising the step.

Preferably, a mixed organic solvent including 20 to 70 parts by weight of toluene, 20 to 65 parts by weight of methyl ethyl ketone, and 5 to 35 parts by weight of normal hexane may be used, and a light stabilizer or antioxidant may be used as necessary. The additives may be mixed and dissolved.

As the photochromic compound used in the present invention, a spiropyran-based compound having less physical destruction by the mixed organic solvent and having superior durability and light fastness to other kinds of photochromic properties is preferred, but is not particularly limited thereto.

The polypropylene resin used in the present invention is not particularly limited, such as resin for extrusion and injection, but it is preferable to use a pellet type for uniform reaction with the photomodified compound, and when producing polypropylene yarn It is better to use general-purpose polypropylene with good physical properties.

After dissolving an appropriate amount in consideration of the concentration with respect to the amount of the polypropylene resin to use the photochromic compound in the mixed organic solvent, the polypropylene resin is added and immersed to react. According to the present invention, a satisfactory effect can be obtained even when the photochromic compound is used in a small amount of 0.0005 to 0.005% by weight based on the polypropylene resin used.

The polypropylene resin is immersed in the mixed organic solvent in which the photochromic compound is dissolved, and reacted with stirring at a high temperature of 60-95 ° C. for 6-9 hours. At this time, when the immersion time is within 6 hours, the color density of the photochromic compound is low, and the uniform penetration of color tends to be difficult.

In addition, in order to promote penetration of the photochromic compound into the polypropylene resin during the reaction, electromagnetic waves or ultrasonic waves may be used, and the inside of the reaction tank may be maintained at a vacuum or a constant pressure.

After the reaction, the polypropylene resin containing the photochromic compound is dried in a drier at 50-85 ° C. for 1-4 hours. In the case of producing the polypropylene yarn, it is preferable to completely dry the polypropylene resin reacted in the mixed organic solvent for at least 1 hour, otherwise it may cause a breakage of the yarn during spinning in the actual process.

According to the present invention as described above, it is possible to obtain a photochromic polypropylene resin having a uniform and effective penetration of a photochromic compound and having excellent photochromic properties. Using the photochromic polypropylene resin according to the present invention, a desired molding can be produced by a general injection method. The photochromic polypropylene resin of the present invention can be applied to all moldings that can be made using general polypropylene resins such as various office containers, sporting goods and lighters.

In addition, when the photochromic polypropylene resin according to the present invention is used, polypropylene yarns having photochromic properties can be obtained by spinning and yarn manufacturing processes of general polypropylene.

At this time, a general polypropylene resin may be added and mixed with the photochromic polypropylene resin obtained by the above method.

The present invention will be described in more detail with reference to the following examples.

<Example 1>

In a 500 L Henschel mixer, a mixed organic solvent consisting of 200-500 g of toluene, 200-400 g of methyl ethyl ketone, and 50-200 g of normal hexane was prepared, and then 0.5-3.0 g of spiropyrane photochromic compound was added to a small amount of a light stabilizer and an antioxidant. Dissolve with. 500-1000 g of polypropylene resin pellets were added thereto, reacted for 6-9 hours at a high temperature of 60-90 ° C., under stirring at 2.0 bar, and then dried at 70-80 ° C. for 1-4 hours. To dry.

The photochromic polypropylene resin obtained by the above method is melt-spun in the same manner as the spinning method of the general propylene company to produce the photochromic polypropylene yarn.

Comparative Example 1

After preparing a mixed organic solvent composed of 100-300 g of xylene, 400-800 g of methyl ethyl ketone, and 50-200 g of ethyl acetate in a 500 L Henschel mixer, a photochromic polypropylene resin was prepared in the same manner as in the above example. However, the reaction time of polypropylene was 15 hours.

In order to obtain the photochromic polypropylene yarn by spinning the photochromic polypropylene resin thus obtained, it failed to obtain a polypropylene yarn.

Table 1 shows the results of observing the discoloration rate and the discoloration degree when the photochromic polypropylene resins prepared according to Example 1 and Comparative Example 1 were exposed to sunlight by sensory inspection.

TABLE 1

Example 1 Comparative Example 1 UV discoloration rate speed usually UV discoloration color Dark usually

In addition, as a result of performing an ultraviolet ray blocking performance test (AATCC 183-1998) on a fabric sample made of the photochromic polypropylene yarn prepared in Example 1, the ultraviolet ray blocking rate was very satisfactory. In addition, the results of the measurement of daylight fastness (KS K 0218), it was confirmed that it is suitable for use in clothing, etc., the results are shown in Table 2.

TABLE 2

UV protection rate ¹⁾ (%)  UV-A  84.6  UV-B  92.3 UV Protection Index (SPF)  11.2 Daylight Fastness ²⁾ (Gray Scale)    4

¹⁾ Light Source-Xenon Arc, Test Equipment-Ultraviolet transmittance Analyzer

²⁾ Light source-Xenon Arc, 20 hours dimming

1A is a photograph showing the state before the photochromic polypropylene yarn (150D / 48f) prepared in Example 1 receives ultraviolet rays, and FIG. 1B shows the polypropylene yarn in purple after irradiation with sun rays (ultraviolet rays). It is a photograph showing the change.

According to the present invention, even when only a small amount of an expensive photochromic compound is used, a photochromic polypropylene resin having excellent photochromic properties and uniform color density can be produced. In addition, in the production of the conventional photochromic polypropylene resin, the photochromic compound was mixed with the resin in the form of a powder or mixed and produced in a masterbatch. In this case, the uniform penetration and distribution of the photochromic compound is difficult, and Due to the development, it was difficult to produce polypropylene yarn, but according to the present invention, even without a separate master batch process, the photochromic compound can be effectively uniformly distributed in the polypropylene resin, and the degree of radiation for the polypropylene yarn It is possible to develop and produce even microfiber.

According to the present invention, it is possible to manufacture moldings of various high-quality polypropylene resins having excellent photochromic properties, and by using photochromic polypropylene yarns, as well as embroidery threads for wigs and clothes, swimwears having photochromic properties and Various products such as sportswear, curtains and mass production fabrics can be developed and produced.

1A and 1B are photographs showing changes in color before and after irradiating sunlight (ultraviolet rays) to the photochromic polypropylene yarn according to the present invention.

Claims (7)

Preparing a mixed organic solution containing toluene, methyl ethyl ketone and normal hexane, Dissolving a photochromic compound in the mixed organic solution; Reacting the solution by adding a polypropylene resin in a solid phase; Method for producing a photochromic polypropylene resin comprising the step of drying the reacted polypropylene resin. The method of claim 1, The mixed organic solvent is 20 to 70 parts by weight of toluene, 20 to 65 parts by weight of methyl ethyl ketone, and 5 to 35 parts by weight of normal hexane. The method for producing a photochromic polypropylene resin according to claim 1, wherein the polypropylene resin is reacted at 60-95 ° C for 6-9 hours. The method for producing a photochromic polypropylene resin according to claim 1, wherein the reacted polypropylene resin is dried at 50-85 ° C for 1-4 hours. Photochromic polypropylene resin by the manufacturing method of any one of Claims 1-4. A molded article using the photochromic polypropylene resin according to any one of claims 1 to 4.   A photochromic polypropylene yarn produced by spinning using the photochromic polypropylene resin according to any one of claims 1 to 4.