KR20040056595A - Method for preparing Poly Propylene(PP) resin containing photochromic compounds, Poly Propylene(PP) yarn and applied Photochromic Resin products Using the Same way - Google Patents

Abstract

PURPOSE: A method for preparing a polypropylene resin containing a photochromic compound, and polypropylene yarn and photochromic product using the polypropylene resin are provided to allow a photochromic compound to be mixed uniformly with a polypropylene resin. CONSTITUTION: The method comprises the steps of dissolving 0.5-3 g of a photochromic compound and a small quantity of a photostabilizer and an antioxidant to an organic solvent mixture comprising 50-200 g of methylene chloride, 100-200 g of ethylene glycol, 100-200 g of xylene, 200-500 g of toluene, 200-400 g of methylethylketone, 50-200 g of n-hexane and 0.1-5 g of an acid; adding 500-1,000 g of a polypropylene resin to the mixture and reacting them at 60-110 deg.C for 6-9 hours; and drying the obtained resin at 50-100 deg.C for 1-4 hours. Preferably the photochromic compound is a spiropyran-based compound.

Description

Method for preparing polypropylene resin containing photochromic compound {Method for preparing Poly Propylene (PP) resin containing photochromic compounds, Poly Propylene (PP) yarn and applied Photochromic Resin products Using the Same way}

The present invention relates to a method of mixing a photochromic compound and a resin, and a photochromic resin molding using the same, and more particularly, to a method for preparing a PP yarn and other PP moldings by synthesizing the photochromic compound into a PP (polypropylene) resin. .

Generally, a photochromic product having a property in which a dye reacts to ultraviolet rays refers to a compound in which a pigment originally possessed reversibly changes from colorless to colored or colored to other colored colors by ultraviolet rays. Blocking ultraviolet rays to the compound in the state is a phenomenon of photochromism showing the characteristic (photochromic) to return to the first color body.

The photochromic material is present in a double-bottom state that absorbs ultraviolet light and visible light strongly, resulting in a color change upon exposure to UV light and reversible color change when the UV light is blocked. Depending on the different colors.

As inorganic compounds, halogen compounds include Hg3, S2, and I2, and organic compounds are based on the isotropy of double bonds (azobenzene and dioindigo) depending on the reaction mode, and based on tautomerism by hydrogen transfer (salicylate). Analilines), pericyclic reactions (prigides), cyclic moieties causing reactions (anthracene), and bond ions (triphenylmethane, spiropyrane).

Benzopyran compound (Korean Patent Application No. 98-18556), naphtopyran compound (Korean Patent Publication No. 99-170432), spiroxazine compound, spiropyran compound (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. 94-7779 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. 99-6814 and 99-48421), such as cosmetics or nail polish (Korean Patent Application No. 99-6813), which focus on photochromic properties of photochromic compounds, The use of compounds is expanding.

On the other hand, until now to provide a variety of colors using such a photochromic compound, in the production of a product using a method of incorporating the photochromic compound in the raw material components, or by dissolving these compounds in a solvent with a polymer coating However, a method of forming a film has been adopted.

For example, in Korean Patent Application No. 2001-1402, 20-30% by weight of resin, 1-3% by weight of camphor, 4-6% by weight of dibutyl phthalate, 4-6% by weight of ethyl acetate, 12-18% by weight of toluene, and butyl 12-18% by weight of acetate, 4-6% by weight of isopropyl alcohol, 10-12% by weight of cellulose acetate butyrate, 0.1-0.3% by weight of polyethylene wax, 8-12% by weight of methyl isobutyl ketone, methyl isoethyl ketone 10 A photochromic trinket accessory coating / printer composition comprising from 15 wt% to 0.5 wt% of a photochromic compound is disclosed, and Korean Patent Laid-Open No. 2001-84405 discloses a mixture of toluene / alcohol with a spiropyrane type photochromic compound. Preparation of the photochromic resin formation in which the solution dissolved in the solvent was infiltrated into the resin granules at 0.05 to 48 hours at 20 to 50 ° C and then heated to 160 to 300 ° C for molding. It has proposed a law.

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. Part, mixed with 0.001 to 5 parts by weight and 0.1 to 20 parts by weight of the photochromic compound, added 50 to 100 parts by weight of resin, immersed for 1 to 24 hours, stirred uniformly, and firstly pulverized by drying the solvent. A method for producing a master batch of a photochromic resin molding which is rapidly cooled after heating is disclosed.

However, despite the excellent discoloration characteristics of the photochromic compound due to the problem that the coating layer of the molding provided by this method is easily peeled off or the particles of the photochromic compound are detached, a better and smoother uniform coating layer is required. There have been many limitations to the use, such that these compounds cannot be used in a wide variety of applications.

In addition, the resin molding provided by the above method has a disadvantage in that durability is not only poorly synthesized in the resin of the photochromic compound.

The present invention has been proposed as part of a solution to the above problems, that is, the mixed organic solvent used as a solvent of the photochromic compound destroys the molecular structure of the photochromic compound can be confirmed that the durability problem is caused. Therefore, the inventors focused on the discovery of a mixed organic solvent and a synthesis method which can be synthesized in a uniform concentration in a PP resin among the organic solvents except for this.

Through this method, a predetermined product can be provided by synthesizing and drying (masterbatching) a photochromic compound and an organic solvent mixture in a general PP resin by a technique of making embroidery yarn for wig yarn, clothing logo and label by using PP yarn. .

Accordingly, it is an object of the present invention to provide a method for producing a PP resin that can be uniformly synthesized with excellent durability and photochromic compound PP in developing a PP photochromic resin.

Another object of the present invention is to develop a PP company using the photochromic PP resin obtained from the above method and to manufacture an application product.

The method for producing PP containing the photochromic compound of the present invention for achieving the above object is methylene chloride 50g to 200g, ethylene glycol 100g to 200g, xylene 100g to 200g, toluene 200g to 500g and methyl ethyl ketone 200g to 400g, normal In a mixed organic solvent consisting of 50 g to 200 g of hexane and 0.1 g to 5 g of acid, 0.5 g to 3 g of a photochromic compound, a light stabilizer and an antioxidant are dissolved in small amounts, and 500 g to 1000 g of a PP resin is added to the solution. A PP resin containing a photochromic compound was prepared, which was reacted at a high temperature of 6 to 9 hours and then dried in a drier at 50 to 100 ° C for 1 to 4 hours.

At this time, if the synthesis time is less than 6 hours, the density of the color is low, the uniform penetration of color tends to be difficult, and especially when the PP yarn is completely dried for more than 1 hour, this may prevent the yarn from boiling during the spinning process. Will be.

Molded article for achieving this purpose is possible to develop injection products and PP yarn application products and embroidery yarn applications and fabrics and fabric applications using PP resin obtained from the above method.

The manufacturing method of PP resin and the good reproducibility of the product can be made clear through the following description.

Looking at the process for producing a PP resin according to the present invention, a mixed organic solvent consisting of methylene chloride, ethylene glycol, xylene, toluene and methyl ethyl ketone, normal hexane, acid 0.5g to 3g and a light stabilizer and antioxidant The mixed organic solvent and the PP resin are synthesized and dried at a proper temperature and for a predetermined time.

According to the present invention, the mixed organic solvent for synthesizing the PP resin which is a photochromic compound is 50 g to 200 g, ethylene glycol 100 g to 200 g, xylene 100 g to 200 g, toluene 200 g to 500 g and methyl ethyl ketone 200 g to 400 g. , A solvent consisting of normal hexane 50 g to 200 g and acid 0.1 g to 5 g is selected.

As the photochromic compound suitable for the present invention, a spiropyran-based compound is preferable, and as a suitable resin, there is no particular limitation to a PP resin for extrusion and injection.

In the case of producing PP yarn, it is possible to use general-purpose PP with good flow property in the physical property itself.

When the photochromic compound is not a spiropyrane compound (Spirooxazine Dye), the physical properties of the mixed organic solvent, the durability of the photochromic properties, and the light fastness are superior to other photochromic compounds.

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

Example 1

In a 500 L Henschel mixer, a mixed organic solvent consisting of 50 g to 200 g of methylene chloride, 100 g to 200 g of ethylene glycol, 100 g to 200 g of xylene, 200 g to 500 g of toluene, 200 g to 400 g of methyl ethyl ketone, 50 g to 200 g of normal hexane, and 0.1 g to 5 g of acid. 0.5 g to 3 g of a photochromic compound, a small amount of a light stabilizer and an antioxidant are dissolved, and 500 g to 1000 g of a PP resin is added to the solution, and then synthesized at a high temperature of 60 to 110 ° C. for 6 to 9 hours, and then 1 to 50 ° C. at 100 ° C. A PP resin containing a photochromic compound which is dried on a drying stand for 4 hours is synthesized.

Example 2

Photochromic PP yarn using photochromic PP resin

Comparative Example 1

The method of incorporating the organic solvent used in Example 1 was changed to permeate the PP resin in the same manner to the mixed organic solvent consisting of 100 g to 300 g of xylene, 400 g to 800 g of methyl ethyl ketone, and 50 g to 200 g of ethyl acetate.

Comparative Example 2

Existing PP Company

According to Example 1 and Comparative Example 1, the discoloration rate and the degree of discoloration were determined by the sensory test when the PP was exposed to indoors and sunlight, and the results of UV discoloration are shown in Table 1 below.

The difference between the existing PP yarn and other synthetic resin yarns is shown in Table 2 below.

Table 3 lists the differences between the photochromic PP yarn of Example 2 and the conventional PP yarn of Comparative Example 2.

Table 1

Table 2

The function of the existing PP company of Comparative Example 2 is as follows.

1. Release moisture and sweat.

2. It is the only fabric that floats because it has a specific gravity smaller than water.

3. Excellent heat retention and cold storage.

4. No static electricity generated.

5. It is resistant to acid, so the fabric is not easily damaged.

6. Non-toxic, hygienic and environmentally friendly recycled fiber.

Table 3

However, although PP is cheaper than other synthetic resins and has high strength, excellent resilience, wear resistance, and high melting point, FINE's production of multifilament yarns and staple fibers has not been expected to grow as expected. .

The photochromic PP of Example 2 can be said to be a useful technique that reinforces the disadvantages of PP yarn ultraviolet light (UV) deterioration and has a fashion function of changing color by ultraviolet rays.

[Figure 1] Effect of UV reaction on photochromic powder

UV measurement equipment: PERKIN-elmer., Colambda9, UV / vis / nir spectrophotometer

As described above, according to the method for preparing the PP resin of the present invention, a mixed organic solvent composed of methylene chloride, ethylene glycol, xylene, toluene and methyl ethyl ketone, normal hexane, and acid is composed of 0.5 g to 3 g of a photochromic compound and a light stabilizer. The mixed organic solvent and PP resin can be uniformly infiltrated for a proper temperature and time to express uniform distribution and high concentration color.

In addition, the present invention by adding a small amount of expensive photochromic powder to make a photochromic resin (1Kg), and maintains a low cost, high efficiency and high added value that can be produced a photochromic PP company in a low ratio with the general PP resin.

Basically, when color is colored in general PP yarn, general dye mixing method or masterbatch is used to make PP resin and mixed product (primary yarn), but the present invention synthesizes photochromic dye in general PP resin to separate master It does not require a batch process, and it has advantages of using existing production equipment, process improvement effect, and cost reduction effect, so that each product has superior competitiveness compared to competitors. By manufacturing high value-added PP yarn products such as various wigs, embroidery thread for garments, general compressors and injection machines are used for all processes except the aging machine and drying rack to control the synthetic concentration, thereby simplifying the process.

Moreover, general photochromic PP is not uniformly distributed when produced in a powder or masterbatch, it is difficult to radiate due to the formation of a yarn phenomenon, it is useful in the present invention that such problems can be solved.

Claims (4)

Photochromic compound 0.5 in a mixed organic solvent consisting of 50 g to 200 g of methylene chloride, 100 g to 200 g of ethylene glycol, 100 g to 200 g of xylene, 200 g to 500 g of toluene, 200 g to 400 g of methyl ethyl ketone, 50 g to 200 g of normal hexane, and 0.1 g to 5 g of acid. dissolving g to 3 g, a light stabilizer and an antioxidant in a small amount; After adding 500 g to 1000 g of PP resin to the solution and reacting at a high temperature of 60 to 110 ° C. for 6 to 9 hours, the photochromic compound was prepared by drying the completed resin at 50 to 100 ° C. for 1 to 4 hours. A method for producing a polypropylene resin containing a photochromic compound, characterized in that a PP resin containing is produced. The method of claim 1, A method for producing a polypropylene resin containing a photochromic compound, characterized in that a spiropyran-based compound is provided as the photochromic compound. The method of claim 1, When the molded product is a PP yarn, the method of producing a polypropylene resin containing a photochromic compound, characterized in that to prevent the boiling of the yarn during spinning to undergo a drying process for at least 1 hour. Photochromic compound 0.5 in a mixed organic solvent consisting of 50 g to 200 g of methylene chloride, 100 g to 200 g of ethylene glycol, 100 g to 200 g of xylene, 200 g to 500 g of toluene, 200 g to 400 g of methyl ethyl ketone, 50 g to 200 g of normal hexane, and 0.1 g to 5 g of acid. After dissolving g-3g, a light stabilizer and an antioxidant in a small amount, 500g-1000g of PP resin was added to the solution, and reacted at a high temperature of 60-95 ° C for 6-9 hours, and then the reaction was completed at 50-100 ° C. PP resin containing a photochromic compound was formed by drying for 1 to 4 hours at The molding includes a polypropylene yarn and a photochromic product containing a photochromic compound, characterized in that the injection product using PP resin and yarn application product using PP yarn, embroidery thread application product, fabric and fabric application product are all included.