KR100438930B1 - Method for Mixing Photochromic Compound and Resin, and Photochromic resin Forms Using the Same - Google Patents

Abstract

In the mixing method of a photochromic compound and resin, this invention is 60 degreeC-80 degreeC, stirring 1 g-2 g and 500 g-1000 g resins of a photochromic compound in presence of the mixed organic solvent which does not contain lower alcohols and lower acetates. The present invention relates to a method for mixing a photochromic compound and a resin and a photochromic resin molded product using the same.

The method of the present invention uses a mixed organic solvent containing no lower alcohols and lower acetates in the mixed organic solvent used as the solvent of the photochromic compound, and uniformly infiltrates the photochromic compound into the resin through a stirring heating process. Highly concentrated colors can be expressed simultaneously with one distribution.

In addition, the photochromic resin according to the present invention has an advantage of excellent appearance of the molded article and uniformly penetrating the high concentration of the photochromic compound into the resin, and can produce a molded article desired by the consumer.

Description

Method for Mixing Photochromic Compound and Resin, and Photochromic Resin Forms Using the Same}

The present invention relates to a method of mixing a photochromic compound and a resin and a photochromic resin molded article using the same. More specifically, the photochromic compound is uniformly mixed with a resin stably at a temperature to use a small amount of an expensive photochromic compound. The present invention also relates to a method of mixing a photochromic compound with a resin and a photochromic resin molded article using the same so as to obtain the addition effect.

In general, "photochromic" refers to a reversible photochromic phenomenon caused by a compound that changes color under ultraviolet light, such as sunlight or artificial light including ultraviolet light, and returns to a colorless and transparent color under ultraviolet light protection or in the dark.

These photochromic materials exist in a double-bottom state that absorbs ultraviolet light strongly and absorbs visible light strongly. Thus, the photochromic material is colored when exposed to ultraviolet rays and then converted into a colorless transparent state when blocked by ultraviolet rays. It is a compound that provides a variety of colors depending on the presence or absence of ultraviolet rays, as a kind of benzopyran-based compound (Korean Patent Application No. 98-018556), naphthopyran-based compound (Korean Patent Publication No. 99-0170432), Spiroxazine-based compounds and spiropyran-based compounds (Korean Patent Application No. 90-701930).

Until now, such photochromic compounds have been mainly used in glass such as automobiles and buildings, or have been used in the manufacture of ophthalmic glass such as sunglass or glass or plastic lenses. For example, Korean Patent Publication No. 94-07779 provides a product having an organic photochromic material in a plastic matrix such as a photochromic ophthalmic lens and a car roof skylight.

Recently, cosmetic products and coating agents (Korean Patent Application Nos. 99-06814 and 99-048421), such as cosmetics or nail polish (Korean Patent Application No. 99-06813), which focus on photochromic properties of photochromic compounds, The use of compounds is expanding.

Meanwhile, until now, such photochromic compounds are used to provide various colors. In the manufacture of products, the photochromic compounds are incorporated into raw materials, or these compounds are dissolved in a solvent together with a polymer and then coated. It has been used by a method of forming a film.

For example, in Korean Patent Application No. 2001-1402, 20 to 30% by weight of resin, 1 to 3% by weight of camphor, 4 to 6% by weight of dibutyl phthalate, 4 to 6% by weight of ethyl acetate, 12 to 18% by weight of toluene , 12-18 wt% butyl acetate, 4-6 wt% isopropyl alcohol, 10-12 wt% cellulose acetate butyrate, 0.1-0.3 wt% polyethylene wax, 8-12 wt% methyl isobutyl ketone, methyl isoethyl ketone 10 Discloses a photochromic trinket accessory coating / printer composition comprising from 15% by weight to 0.5% by weight of a photochromic compound,

In Korean Patent Laid-Open No. 2001-84405, a solution in which a spiropyrane type photochromic compound is dissolved in a toluene / alcohol mixed solvent is infiltrated into a resin granule at 0.05 to 48 hours at 20 to 50 ° C, and then heated to 160 to 300 ° C. The manufacturing method of the photochromic resin molding to shape | mold is disclosed.

In addition, Korean Patent Application No. 2001-29435 discloses 30 to 50 parts by weight of methyl ethyl ketone, 10 to 20 parts by weight of toluene, 10 to 20 parts by weight of xylene, 5 to 10 parts by weight of ethyl acetate, and 5 to 10 parts by weight of isopropyl alcohol. After mixing the fragrance 0.001-5 parts by weight and the photochromic compound 0.1-20 parts by weight, 50-100 parts by weight of the resin was added and immersed for 1 to 24 hours, and after stirring uniformly, the solvent was dried and primary grinding Then, a method for producing a master batch of a photochromic resin molding which is rapidly cooled after heating is disclosed.

However, the coating layer provided by this method is easily peeled off, or due to problems such as desorption of the photochromic compound particles, in spite of the excellent discoloration characteristics of the photochromic compound, these compounds are required to form a better and smoother uniform coating layer. There have been many limitations on its use, such as its inability to use in a wide variety of other fields.

In addition, the resin molding provided by the above method was not only poor in durability, but also had a disadvantage that the photochromic compound did not penetrate uniformly into the resin.

Therefore, in the present invention, as a result of extensive research in order to solve the above problems, lower alcohols and lower acetates in the mixed organic solvent used as the solvent of the photochromic compound destroys the molecular structure of the photochromic compound, thereby causing problems in durability. In addition, when the mixing temperature of the photochromic resin molding is maintained at room temperature, it was found that the speed of the manufacturing process was decreased and the concentration of color could not penetrate deeply. In addition, by the appearance of a wave pattern on the surface of the injection molding, it was confirmed that the photochromic compound did not penetrate uniformly, and was completed based on the present invention.

Accordingly, it is an object of the present invention to provide a method of mixing a photochromic compound and a resin which is excellent in the durability of the photochromic resin molding and can uniformly penetrate the photochromic compound into the resin.

Another object of the present invention is to provide a photochromic resin molding obtained from the above method.

The method for mixing the photochromic compound and the resin of the present invention for achieving the above object comprises 1 g to a photochromic compound in the presence of a mixed organic solvent containing no lower alcohols and lower acetates in the method for mixing the photochromic compound and the resin. 2 g and 500 g to 1000 g of the resin are infiltrated at 60 DEG C to 80 DEG C with stirring for 4 to 8 hours, followed by drying.

The photochromic resin molding for achieving another object of the present invention is obtained from the above method is a writer, ballpoint pen, CD case, pile case, sunglasses, goggles, cosmetic containers, hat window, beverage containers, buttons, artificial nails, automotive products Or motorcycle articles.

Looking at the present invention in more detail as follows.

As described above, the mixing method of the present invention penetrates and dries the photochromic compound and the resin for an appropriate temperature and time in the presence of a mixed organic solvent containing no lower alcohols and lower acetates.

According to the present invention, lower alcohols such as isopropyl alcohol, and lower acetates such as ethyl acetate, butyl acetate and the like in the mixed organic solvent used as the solvent of the photochromic compound are molecules of the photochromic compound. By destroying the structure to reduce the color durability of the photochromic resin molding, the present invention eliminated the use of the mixed organic solvent.

In the present invention, a preferred mixed organic solvent for dissolving 1 g to 2 g of the photochromic compound is at least two selected from the group consisting of methyl ethyl ketone 100 g to 600 g, toluene 100 g to 700 g, xylene 100 g to 200 g and methylene chloride 400 g to 700 g. Solvent.

Particularly, in the present invention, 400 g to 700 g of methylene chloride may be used as a mixed organic solvent, and the methylene chloride has not been used as a solvent for a photochromic compound.

If the amount of the methylene chloride is less than 400g, there is a tendency to color the surface of the resin due to supersaturation of the color, and if it exceeds 700g, the concentration of the color is low and it is difficult to penetrate uniformly.

The photochromic compound suitable for the present invention is preferably a naphthopyran-based compound, and a suitable resin is preferably polypropylene or polyethylene, but is not limited thereto.

The mixing ratio of the photochromic compound and the resin is usually 1 g to 2 g of the photochromic compound and 500 g to 1000 g of the resin. In addition to the above components, light stabilizers, antioxidants, fragrances and / or dyes may be added in small amounts as necessary.

According to the present invention, in the presence of a mixed organic solvent containing no lower alcohols and lower acetates, the photochromic compound and the resin are permeated and dried at 60 ° C to 80 ° C for 4 to 8 hours.

Conventionally, the mixing temperature of the photochromic compound and the resin was mainly performed at room temperature, but the mixing process was slow and the color density could not penetrate deeply, and the scratches such as wave patterns appeared on the surface of the injection molded product. And infiltrated at 60 ° C. to 80 ° C. for 4 to 8 hours and dried.

At this time, if the temperature is less than 60 ℃ the solubility of the photochromic compound is difficult to express the color, if the temperature exceeds 80 ℃ it is difficult to penetrate the compound into the resin due to the melt phenomenon of the resin, the color density of less than 4 hours Is low, uniform penetration of color is difficult, and when it exceeds 8 hours, uniform color penetration tends to be difficult due to melting of the resin surface.

As described above, in the present invention, the mixed organic solvent and the photochromic compound are liquefied and uniformly mixed in the resin, and then heated at a temperature of 60 ° C. to 80 ° C. so that the photochromic compound can be uniformly infiltrated into the resin, while the color heat resistance and color of the resin are Since the durability can be maintained, an excellent molding can be produced.

That is, the molded article can be obtained by molding the photochromic resin obtained from the above method at 160 ° C to 220 ° C.

The molded article is preferably used as a lighter, a ballpoint pen, a CD case, a pile case, sunglasses, goggles, a cosmetic container, a hat window, a beverage container, a button, an artificial nail, an automobile article, a motorcycle article, and the like, but is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to the following Examples, but the scope of the present invention is not limited to the following Examples.

Example 1

After mixing 500g Henschel mixer with 300g of methyl ethyl ketone, 400g of toluene, 2g of photochromic compounds (Japan, Prism, Photochromic) and 300g of dye (Blue Sky), 1000g of polypropylene and 0.05g of light stabilizer (Japan Seikaplen 100) 0.03 g of antioxidant (Sanol LS76, Japan) was mixed again and mixed at 500 rpm for 1 minute and then infiltrated at about 70 ° C. for about 5 hours.

The infiltrated resin was dried in a drying stand for about 3 hours to remove the solvent, the dried resin was pulverized, put into an injection molding machine, and injection molded at about 200 ° C. to prepare a molded product.

When the molded product is exposed to ultraviolet light, the concentration can be directly identified by the naked eye, and the density of the color and the durability of the color were measured.

Example 2

In Example 1, the dye was red, the solvent was 150 g of xylene and 550 g of MC (methylene chloride), and the resin was replaced with polyethylene. Color durability was measured and the results are shown in Table 1 below.

Comparative Example 1

In Example 1, 40 g of methyl ethyl ketone, 15 g of toluene, 15 g of xylene, 10 g of ethyl acetate, and 5 g of isopropyl alcohol were used, except that the permeation temperature was performed at room temperature (about 25 ° C.). .

When the molded product is exposed to ultraviolet light, the concentration can be directly identified by naked eye, and the density and color durability of the color were measured, and the results are shown in Table 1 below.

Comparative Example 2

Except that polyethylene was used as the copolymer resin in Comparative Example 1 was carried out in the same manner, the color durability and the concentration of the color of the molding was measured and the results are shown in Table 1 below.

Properties Example 1 Example 2 Comparative Example 1 Comparative Example 2 Yield Tensile Strength (kg / ㎠) 300 310 280 290 Density of colors Thick Very thick Thin usually Color durable No change No change Color decay Color decay

In Table 1, the color durability was determined by visually determining the color change after exposing the molding to ultraviolet rays 300 times at 1 hour intervals.

As described above, the method of the present invention uses a mixed organic solvent containing no lower alcohols and lower acetates in the mixed organic solvent used as the solvent of the photochromic compound, and the photochromic compound is added to the resin through a stirring heating process. By penetrating uniformly, high concentration color can be expressed simultaneously with uniform distribution.

In addition, the photochromic resin according to the present invention has the advantage of excellent appearance of the molded article and the production of the desired molded article by the consumer while uniformly penetrating the high concentration of the photochromic compound into the resin.

Claims (6)

In the mixing method of a photochromic compound and resin, Does not contain lower alcohols and lower acetates, 400 g to 700 g of methylene chloride as an essential ingredient, 1 g to 2 g and 500 g to 1,000 of photochromic compounds A method of mixing a photochromic compound and a resin, wherein the resin is infiltrated at 60 ° C. to 80 ° C. for 4 to 8 hours with stirring, followed by drying. delete The method according to claim 1, wherein the photochromic compound is a naphthopyran-based compound. The method of mixing a photochromic compound and a resin according to claim 1, wherein the resin is polypropylene or polyethylene. The photochromic resin molding obtained from the method of any one of Claims 1, 3, or 4. The molded article according to claim 5, wherein the molded article is a writer, a ballpoint pen, a CD case, a pile case, sunglasses, goggles, a cosmetic container, a hat window, a beverage container, a button, an artificial nail, an automotive article or a motorcycle article.