JP5018084B2 - Resin composition - Google Patents

Description

  The present invention relates to a composition in which fine fillers are dispersed with a hyperbranched polymer, for example, suitable for adhesives, paints, and various coating agents.

  In order to improve the properties of a polymer compound, it is often performed to combine a polymer compound and a filler into a resin composition. The purpose of utilizing fillers is to improve physical properties such as mechanical properties, thermal properties, and electrical properties, to provide functions such as conductivity, magnetism, flame retardancy, and vibration control properties, to adjust viscosity and improve anti-blocking properties, etc. In addition, there is an effect of reducing the cost as an inexpensive extender depending on the filler.

  When the filler particles become finer and the surface area of the particles increases, the interaction with the matrix resin becomes stronger, and the tensile strength and impact resistance as the resin increase. In that case, the effect of the finer filler not only appears in the mechanical properties but also improves the surface smoothness of the molded product. Furthermore, the improvement of the characteristic resulting from a filler is recognized by refinement | miniaturization of a filler. For example, conductivity is improved by using carbon black, magnetic properties are improved by using magnetic particles, flame retardancy is improved by using aluminum hydroxide, and ultraviolet absorption is improved by using titanium oxide or zinc oxide. To do. Therefore, submicron-order ultrafine particles have been put into practical use, and fine particles (nanoparticles) of 100 nm or less have been applied to fillers. For example, it is known that a highly transparent coating film can be obtained by a paint in which these nanoparticles are dispersed (see Non-Patent Document 1).

Conventionally, polymers having functional groups such as carboxylic acid groups and amino groups have been used as binder resins for dispersing fine fillers. For the dispersion of magnetic particles where it is relatively difficult to obtain a good dispersion state, it is effective to use, for example, a linear polyester resin or polyurethane resin containing a sulfonic acid metal salt in the molecule as a binder resin. (See, for example, Patent Documents 1 and 2).

However, since the nanoparticles easily aggregate, even if the binder resin is dissolved in a solvent and the nanoparticles are dispersed, the fluidity of the dispersion is poor. Moreover, since the nanoparticles are immediately aggregated in the dispersion or the coating film, the function of the nanoparticles cannot be sufficiently exhibited. Therefore, the surface smoothness and transparency of the coating film using the dispersion often deteriorate. For example, even if a dispersion is prepared using a linear polymer containing a sulfonic acid metal base described in Patent Documents 1 and 2, it is insufficient to exhibit the characteristics inherent to the nanoparticles.

Japanese Patent Publication No.57-3134 Japanese Patent Publication No.58-41565 Isao Soma, Plastic, 49 (10), 20 (1998)

  An object of the present invention is to provide a dispersion in which the dispersibility of the nanoparticles is good and aggregation of the nanoparticles hardly occurs.

  As a result of intensive studies on the resin for dispersing nanoparticles, the present inventors have reached the present invention. That is, the present invention is a resin composition in which a filler having an average particle size of 0.1 μm or less is dispersed in a hyperbranched polymer. Preferably, the above-mentioned resin composition has a number average molecular weight of the hyperbranched polymer of 500 to 50,000 and a hyperbranched polymer dispersion ratio of 4 or less.

  The resin composition of the present invention is excellent in dispersion of nanofillers, and can fully draw out the functions of the nanofillers. Therefore, it is expected to obtain a coating film having unprecedented physical properties in applications of paints, adhesives and coating agents.

  The filler used in the present invention is effective when the average particle size is 0.1 μm or less. If it exceeds 0.1 μm, the dispersion with the hyperbranched polymer is deteriorated, or the difference from the linear polymer is not recognized. The effect of improving the dispersion of the nanofiller by the hyperbranched polymer seems to be due to the small entanglement structure of the hyperbranched polymer. Although the minimum of the average particle diameter of a filler is not specifically limited, A dispersion effect becomes high at 0.001 micrometer or more.

  In the present invention, the average particle diameter of the filler can be obtained by observing with an electron microscope and averaging 100 samples of arbitrary measurement results. For example, when the shape of the filler is an ellipse, both the major axis and the minor axis must be 0.1 μm or less. Even if there are fine irregularities, the average particle diameter is calculated based on the longest diameter.

  Examples of the function imparted by the filler in the present invention and the filler used therefor include the following. In order to impart conductivity and antistatic function, carbon black such as ketjen black, stannic oxide, zinc oxide, or fine particles such as silver and nickel can be used. For imparting magnetism, various ferrites, magnetic iron oxides, niobium-iron-boron alloys can be used. Alumina, aluminum nitride, and boron nitride can be used for imparting thermal conductivity. In order to impart piezoelectricity, barium titanate and lead zirconate titanate can be used. For imparting damping properties, mica, graphite, potassium titanate, zonolite, and ferrite can be used. Lead powder, iron powder, and barium sulfate can be used to provide sound insulation. For imparting slidability, graphite, hexagonal boron nitride, molybdenum sulfate, polyfluorinated ethylene powder, and talc can be used. Examples of the friction material include mica, asbestos, zonotlite, and potassium titanate. Examples of anti-blocking include silica and ultrafine calcium carbonate. Glass baluns, shirasu baluns, and various plastic baluns are included for heat insulation and weight reduction. For imparting electromagnetic wave absorption, ferrite, graphite, charcoal powder, and lead zirconate titanate can be used. For light scattering reflection, glass beads, silica, calcium carbonate, titanium oxide, aluminum powder, pearl mica can be used. Magnesium oxide, hydrotalcite alumina, and charcoal powder can be used to impart heat radiation. For imparting flame retardancy, aluminum hydroxide, magnesium hydroxide, antimony oxide, zinc borate, and zinc carbonate can be used. Titanium oxide, zinc oxide, cerium oxide can be used for imparting ultraviolet absorptivity. Lead powder and barium sulfate can be used for imparting radiation absorption. For imparting antibacterial properties, silver powder, copper ion-supporting zeolite, zinc oxide, copper phthalocyanine can be used. Examples of the dehydrating agent include calcium oxide, magnesium oxide, silica gel, and zeolite. Examples of the deodorizer include chi zeolite, ceviolite, activated clay, and charcoal. Among these, the present invention is suitable for applications in which the better the dispersion of the filler and the smaller the particle size of the filler, the better the performance. An example of such an application is a color filter.

  The resin composition of the present invention can be used for forming pixels of color filters used in liquid crystal displays. As pigments for color filters, organic pigments include phthalocyanine, azo, indico, anthraquinone, perylene, and quinacridone, and inorganic pigments include cadmium red, cadmium yellow, cobalt green, cobalt blue, chromium oxide, and ultramarine blue. The red pixel is preferably anthraquinone, and the green and blue are preferably phthalocyanine. As a pigment for a pigment dispersion resist of a color filter, a filler having a smaller primary particle is required from the viewpoint of transparency.

In the present invention, a hyperbranched polymer is used as a binder component.
A hyperbranched polymer is a polymer having a highly branched structure obtained by reacting a polyfunctional monomer having three or more functional groups capable of reacting with each other in a molecule. A polymer having a structure different from that of a polymer. For example, conventionally, hyperbranched polymers of polyester, polyamide, polyurethane, polyether, polyethersulfone, and polycarbonate have been synthesized.

  The hyperbranched polymer referred to in the present invention is not particularly limited in its structure, but a polymer of ABx (x is an integer of 2 or more) type molecule is preferable.

The hyperbranched polymer will be described. This hyperbranched polymer can be synthesized by polymerization of ABx (x is an integer of 2 or more) type molecules. Here, A and B represent different functional groups, which are functional groups that do not self-condensate but can be condensed between AB. Examples of the combination of A and B or B and A include hydroxyl group and carboxylic acid group, amino group and carboxylic acid group, halogen and phenolic hydroxyl group, acetoxy group and carboxylic acid group, acetyl group and hydroxyl group, and the like. Derivatives and carboxylic acid groups or derivatives thereof are desirable. A molecule of ABx (x is an integer of 2 or more) type is a reaction of A2 (a compound having two functional groups of A in one molecule) and B3 (a compound having three functional groups of B in one molecule), A2 and B′B2 (a compound having one B ′ functional group and two B functional groups in one molecule, B ′ does not react with B, but reacts with A. B ′ and B with respect to A Can be obtained from the reaction.

  Specific examples of the ABx (x is an integer of 2 or more) type molecule include 2,2-dimethylolpropionic acid, 2,2-dimethylolbutanoic acid, diphenolic acid, and 5- (2-hydroxyethoxy). Isophthalic acid, 5-acetoxyisophthalic acid, 3,5-bis (2-hydroxyethoxy) benzoic acid, 3,5-bis (2-hydroxyethoxy) benzoic acid methyl ester, 5- (bromomethyl) -1,3-dihydroxy Examples thereof include polycondensates using benzene, 3,5-diaminobenzoic acid, phenol-3,5-diglycidyl ether, a one-to-one reaction product of isophorone diisocyanate and diisopropanolamine, and the like.

  AB type compounds such as glycolic acid, hydroxypivalic acid and aminobenzoic acid may be used as the branch point of the hyperbranched polymer or for adjusting the end group. The polymerization conditions for the hyperbranched polymer are appropriately selected according to the raw materials used and the characteristics of the polymer obtained.

Next, a hyperbranched polymer using an equimolar reaction product of the reaction of A2 (a compound having two functional groups of A in one molecule) and B3 (a compound having three functional groups of B in one molecule) will be described. To do. An example of this is the reaction of p-phenylenediamine with 1,3,5-benzenetricarboxylic acid. These equimolar reactants include compounds having one amino group and two carboxyl groups. By purifying only this, it becomes the raw material of the piper branch polymer. Therefore, if this purified product is used for polymerization, a hyperbranched polymer can be obtained.

  Further, A2 and B′B2 (a compound having one B ′ functional group and two B functional groups in one molecule, B ′ does not react with B, but reacts with A. B ′ with respect to A and The hyperbranched polymer that can be produced from the reaction product of B) is different. An example of this is the reaction of hexamethylene diisocyanate with N-diethanolamine. N-diethanolamine has an amino group and a hydroxyl group, both react with an isocyanate group, but the reaction rate is overwhelmingly higher in the case of an amino group. In an equimolar reaction product of hexamethylene diisocyanate and N-diethanolamine, a compound having two hydroxyl groups and one isocyanate group is preferentially produced. When this is used as a raw material, a hyperbranched polymer is obtained.

  The number average molecular weight of the hyperbranched polymer used in the present invention is preferably 500 to 50,000, more preferably 2,000 to 20,000. If the number average molecular weight is less than 500, the durability of the coating film may be poor, and if it exceeds 50,000, the solubility of the general-purpose solvent may decrease.

  The dispersion ratio (weight average molecular weight / number average molecular weight) of the hyperbranched polymer is preferably 4 or less. When 4 is exceeded, aggregation of a filler may occur.

The resin composition of the present invention contains a hyperbranched polymer and a fine filler. The ratio of the hyperbranched polymer to the fine filler is preferably used in the range of 1: 0.1 to 1:10 by mass ratio. If outside this range, the function of the fine filler may not be exhibited.

  In addition to the hyperbranched polymer and the fine filler, the resin composition of the present invention can be used as a coating agent or a paint to form a paint-like dispersion by using an organic solvent in combination. Such a dispersion is very useful in that it has a very good stability, there is little aggregation of fillers over time, and the viscosity of the paint does not easily rise, so that the usable life is long. The content of the organic solvent can be set in the range of preferably 30 to 97% by weight with respect to the total amount of the resin composition.

Organic solvents used include aromatic hydrocarbons such as toluene, xylene and solvesso, esters such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate and dibasic acid esters, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and isophorone. And the like, and ethers such as n-butyl cellosolve and t-butyl cellosolve, and the like, which are selected in consideration of solubility, evaporation rate and the like.

Moreover, you may mix | blend a hardening | curing agent with the resin composition of this invention as needed. Examples of the curing agent that can be used in the present invention include a phenol resin, an amino resin, an isocyanate compound, and an epoxy resin, and one or two or more of these can be arbitrarily selected and used. The amount used is preferably in the range of 1 to 50% by weight with respect to the hyperbranched polymer.

  Examples of the phenol resin include phenol, o-cresol, p-cresol, m-cresol, p-tert-butylphenol, p-ethylphenol, 2,3-xylenol, 2,5-xylenol, m-ethylphenol, 3, Resol-type phenol resin obtained by methylolation of phenol compounds such as 5-xylenol, m-methoxyphenol, bisphenol-A, bisphenol-F, etc. with formalin, paraformaldehyde or trioxane, and the like, methanol, ethanol, n-propanol, n -Resol type phenol resin alkyl etherified with butanol or isobutanol may be mentioned, and one or more of these may be used in combination.

  Amino resins include methylolated amino obtained by reaction of amino components such as melamine, urea, benzoguanamine, acetoguanamine, steroguanamine, spiroguanamine, dicyandiamide, and aldehyde components such as formaldehyde, paraformaldehyde, acetaldehyde, and benzaldehyde. Resin. Those obtained by etherifying the methylol group of this methylolated amino resin with an alcohol having 1 to 6 carbon atoms are also included in the amino resin.

  Examples of amino resins using benzoguanamine include methylether benzoguanamine resins obtained by etherifying methylol groups of methylolated benzoguanamine resins partly or entirely with methyl alcohol, butyl etherified benzoguanamine resins butyl etherified with butyl alcohol, or methyl alcohol. Methyl ether etherified with both butyl alcohol and mixed etherified benzoguanamine resin with butyl ether are preferred. As said butyl alcohol, isobutyl alcohol and n-butyl alcohol are preferable.

  As the amino resin using melamine, a methylol group of the methylolated melamine resin is partially or entirely etherified with methyl alcohol, methyl etherified melamine resin, butyl etherified butyl etherified with butyl alcohol, or methyl alcohol Preference is given to methyl ether etherified with both butyl alcohol and mixed etherified melamine resin with butyl ether. One of these or two or more may be used in combination.

Examples of the isocyanate compound include aromatic, alicyclic, and aliphatic diisocyanate compounds, and trivalent or higher polyisocyanate compounds, which may be either low molecular compounds or high molecular compounds. For example, tetramethylene diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, or a trimer of these isocyanate compounds, and an excess of these isocyanate compounds For example, low molecular active compounds such as ethylene glycol, propylene glycol, trimethylolpropane, glycerin, sorbitol, ethylenediamine, monoethanolamine, diethanolamine, triethanolamine or various polyester polyols, polyether polyols, polymer active hydrogens of polyamides Terminals obtained by reacting with compounds, etc. Isocyanate group-containing compound. You may use 1 type, or 2 or more types from these.

  Moreover, when a pot life is required, a blocked isocyanate compound can be used as the isocyanate compound. Examples of the isocyanate blocking agent include phenols such as phenol, thiophenol, methylthiophenol, cresol, xylenol, resorcinol, nitrophenol, chlorophenol, oximes such as acetooxime, methylethyl ketoxime, cyclohexanone oxime, methanol, ethanol, propanol, Alcohols such as butanol, halogen-substituted alcohols such as ethylene chlorohydrin and 1,3-dichloro-2-propanol, tertiary alcohols such as t-butanol and t-pentanol, and lactams such as ε-caprolactam In addition, aromatic methylene compounds such as aromatic amines, imides, acetylacetone, acetoacetic acid ester, malonic acid ethyl ester, mercaptans, imi S, ureas, and also such as diaryl compounds sodium bisulfite. The blocked isocyanate compound is obtained by reacting the isocyanate compound and the blocking agent by a conventionally known method, and each can be used alone or in combination.

  Examples of the epoxy resin include bisphenol-A diglycidyl ether and oligomers thereof, orthophthalic acid diglycidyl ester, isophthalic acid diglycidyl ester, terephthalic acid diglycidyl ester, p-hydroxybenzoic acid diglycidyl ester, and tetrahydrophthalic acid. Diglycidyl ester, hexahydrophthalic acid diglycidyl ester, succinic acid diglycidyl ester, adipic acid diglycidyl ester, sebacic acid diglycidyl ester, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl Ethers, 1,6-hexanediol diglycidyl ether, and polyalkylene glycol diglycidyl ethers, trimellitic acid Diglycidyl ester, triglycidyl isocyanurate, 1,4-glycidyloxybenzene, diglycidyl propylene urea, glycerol triglycidyl ether, trimethylol ethane glycidyl ether, trimethylol propane triglycidyl ether, pentaerythritol tetraglycidyl ether, glycerol alkylene oxide addition The triglycidyl ether of a thing can be mentioned. These can be used alone or in combination.

  A curing catalyst can be used in the resin composition of the present invention depending on the type of curing agent. For example, when a phenol resin or an amino resin is used, organic sulfonic acid, organic carboxylic acid, phosphoric acid, and neutralized amines thereof may be used. When using an isocyanate compound, an organotin compound, a tertiary amine compound, and salts thereof may be used. When using an epoxy resin, an amine compound or an organic phosphorus compound may be used. One or two or more of these catalysts can be arbitrarily selected and used.

The resin composition of the present invention may contain a resin other than the hyperbranched polymer. Examples of resins other than hyperbranched polymers include polyester resins, polyurethane resins, acrylic resins, and epoxy resins.

  The resin composition of the present invention is preferably used for paints, adhesives, coating agents and the like, but even if used for molding applications, excellent effects can be expected in terms of mechanical properties.

  The present invention is specifically illustrated by the following examples. In the examples, “parts” means “parts by mass”. Analysis and evaluation of the resin were carried out by the following methods.

(Molecular weight and molecular weight distribution)
Using polystyrene gel permeation chromatography (GPC) 150c with tetrahydrofuran as an eluent, measurement was performed at a column temperature of 35 ° C. and a flow rate of 1 ml / min. . However, Showa Denko Co., Ltd. shodex KF-802, 804, 806 was used for the column.

(Composition analysis)
¹ H-NMR analysis was performed using a nuclear magnetic resonance analyzer (NMR) Gemini-200 manufactured by Varian in DMSO-d ₆ solvent, and the integration ratio was determined.

Synthesis of hyperbranched polymer (A) 1.34 parts of trimethylolpropane and 31 parts of dimethylolbutanoic acid were charged into a reaction vessel equipped with a thermometer, a stirrer, and a Liebig condenser, and p-toluenesulfonic acid 0. Two parts were added. While flowing nitrogen gas, the reaction was carried out at 140 ° C. under normal pressure for 3 hours to distill off the produced water. Thereafter, the reaction was further continued for 1 hour under reduced pressure (5 mmHg). The properties of the obtained polyester resin (A) are shown in Table 1. In addition, the composition ratio of a table | surface is mass ratio.

Hyperbranched polymer (B) synthesis stirrer, cooling device, dehydrated solvent (toluene / cyclohexanone / dimethylformamide (30/30/30 parts)) and polyester resin in a 500 ml glass flask equipped with two chemical inlets 10 parts of 1 (terephthalic acid / isophthalic acid / ethylene glycol / neopentyl glycol = 50/50/50/50 molar ratio, number average molecular weight 2000) were charged and dissolved. While stirring, 13.3 parts of diisopropanolamine from one chemical inlet and 22.2 parts of isophorone diisocyanate from other chemical inlets were simultaneously added dropwise at the same rate over 5 minutes. Ten minutes after the completion of dropping, 0.05 part of dibutyltin dilaurate was added as a reaction catalyst. The temperature of the reaction system was kept at 80 ° C. for 10 hours to complete the reaction. A polyurethane urea resin solution having a hyperbranched structure was obtained. The properties of the resin are shown in Table 1.

Synthesis of Hyperbranched Polymer (C) In a reaction vessel equipped with a thermometer, a stirrer, and a Liebig condenser, 20 parts of 3,5-dihydroxy-4′-fluorobenzophenone, 20 parts of potassium carbonate, and N-methyl dried as a solvent 150 parts of pyrrolidone and 100 parts of dry toluene were charged. The reaction mixture was heated to reflux for 3 hours, and water produced was removed out of the system. While removing the solvent in the system by distillation, the temperature of the reaction system was raised to 200 ° C., and the mixture was further heated at 200 ° C. for 3 hours. The reaction was then poured into water and precipitated. Reprecipitation was repeated with tetrahydrofuran / methanol. The characteristics of the obtained hyperbranched polymer (C) are shown in Table 1.

Synthesis of hyperbranched polymer (D) In place of 20 parts of 3,5-dihydroxy-4′-fluorobenzophenone used in the synthesis of hyperbranched polymer (C), 3,5-difluoro-4′-hydroxybenzophenone was used for hypertension. Hyperbranched polymer (D) having fluorine as a terminal group was obtained in the same manner as branch polymer (C). The characteristics of the obtained hyperbranched polymer (D) are shown in Table 1.

Synthesis of Hyperbranched Polymers (E) to (G) 20 parts of 5-acetoxyisophthalic acid and 0.1 part of tetrabutoxytitanium were charged in a reaction vessel, and the system was maintained under reduced pressure while heating to 250 ° C. After heating for 30 minutes, the mixture was cooled to 50 ° C., 100 parts of tetrahydrofuran and 10 parts of water were added, and the mixture was refluxed for 4 hours. The resulting solution was poured into water and precipitated. Properties of the obtained hyperbranched polymer (E) are shown in Table 1.
In the same manner as the hyperbranched polymer (E), a piperbranched polymer was obtained using the raw materials described in Table 1. The evaluation results of the resin are shown in Table 1.

[Example 1]
A composition having the following blending ratio is put in a ball mill and dispersed for 24 hours, and then 1 part of a polyisocyanate compound (Coronate L, manufactured by Nippon Polyurethane Industry Co., Ltd.) is added as a curing agent, and further mixed for 10 minutes to obtain a paint. It was. The obtained paint was applied and dried on a polyethylene terephthalate film having a thickness of 15 μm so that the thickness after drying was 4 μm. The obtained coated film was allowed to stand at 60 ° C. for 1 day, and then the surface gloss and surface roughness of the coated layer were measured. The surface roughness was measured in the range of 200 × 200 μm ² using a light interference three-dimensional surface roughness meter (manufactured by WYKO). In addition, the viscosity of the coating material after adding the polyisocyanate compound was observed at room temperature for one day. ○: Returned to the original state by simple stirring, Δ: Flowed by simple stirring, but increased in viscosity compared to the original, and X: Not evaluated by simple stirring. The evaluation results are shown in Table 2.
Compounding 10 parts of hyperbranched polyester resin obtained in Polymerization Example 1
(30% solution of cyclohexanone)
Iron oxide (hematite) 15 parts (major axis length 0.05μm, major axis / minor axis ratio 8.5)
Cyclohexanone 1 part Toluene 5 parts Methyl ethyl ketone 14 parts

Examples 2-6 Comparative Examples 1-3
A coated film was prepared in the same manner as in Example 1, except that the binders listed in Table 1 were used instead of the polyester resin used as the binder for the coating layer. The results are shown in Table 2.
In Comparative Examples 1 and 2, a sulfonic acid sodium salt-containing polyester / urethane resin manufactured by Toyobo Co., Ltd. was used instead of the hyperbranched polyester used in Example 1. In Comparative Examples 2 and 3, hematite having a major axis of 0.5 μm and a major axis / minor axis ratio of 9 was used instead of the hematite having a major axis of 0.05 μm used in Example 1.

[Example 7]
A composition having the following blending ratio was placed in a ball mill and dispersed for 24 hours, and then 1 part of polyisocyanate compound (Coronate L, manufactured by Nippon Polyurethane Industry Co., Ltd.) as a curing agent was further mixed for 10 minutes to obtain a paint. Moreover, the coating material was apply | coated on the 50-micrometer-thick polyethylene terephthalate film so that the thickness after drying might be set to 1 micrometer. The visible light transmittance of the coated film was measured. The light transmittance of only the polyethylene terephthalate film is 93%. In addition, paint stability was evaluated in the same manner as in Example 1. The evaluation results are shown in Table 3.
Compounding 10 parts of hyperbranched polyester resin obtained in Polymerization Example 1
(30% solution of dioxane)
Phthalocyanine (average particle size 0.04 μm) 4 parts Toluene 4 parts Methyl ethyl ketone 4 parts

In Table 2, the symbols are as follows.
UR8300: Toyobo Co., Ltd. sodium sulfonate group-containing polyester urethane M / T / C: methyl ethyl ketone / toluene / cyclohexanone = 1/1/1 mass ratio THF: tetrahydrofuran

Examples 8-11 Comparative Examples 4-6
A coating film was prepared in the same manner as in Example 7 except that the binders listed in Table 3 were used instead of the polyester resin used as the binder for the coating layer. The results are shown in Table 3.
In Comparative Examples 4 and 5, copolymerized polyester resin-2 was used in place of the hyperbranched polyester used in Example 7. In Comparative Examples 5 and 6, phthalocyanine blue having a particle size of 0.15 μm was used instead of phthalocyanine blue having a particle size of 0.04 μm used in Example 7.

In Table 3, the symbols are as follows.
Polyester resin-2: terephthalic acid / sebacic acid / ethylene glycol / neopentyl glycol = 80/20 // 50/50 molar ratio, number average molecular weight 20,000

  From the results of Tables 2 and 3, it can be seen that the compositions described in the examples are excellent in coating stability and hardly cause aggregation of the filler. Moreover, the coating film is excellent in surface gloss, surface roughness, and light transmittance reflecting the dispersion state.

  The resin composition of the present invention is excellent in dispersion of nanofillers, and can fully draw out the functions of the nanofillers. Therefore, it is expected to obtain a coating film having unprecedented physical properties in applications of paints, adhesives and coating agents.

Claims (7)

A filler having an average particle size of 0.1 μm or less is of the ABx type (x represents an integer of 2 or more. A and B represent different functional groups and do not self-condensate but represent functional groups capable of condensing between AB). A resin composition dispersed in a hyperbranched polymer synthesized by molecular polymerization . The resin composition according to claim 1, wherein the number average molecular weight of the hyperbranched polymer is 500 to 50,000. The resin composition according to claim 1 or 2, wherein the hyperbranched polymer has a dispersion ratio of 4 or less. The combination of A and B or B and A is a hydroxyl group and a carboxylic acid group, an amino group and a carboxylic acid group, a halogen and a phenolic hydroxyl group, an acetoxy group and a carboxylic acid group, or an acetyl group and a hydroxyl group. The resin composition according to any one of claims 1 to 3, which is a combination. The resin composition according to any one of claims 1 to 4 , wherein a mixing ratio of the hyperbranched polymer and the filler is in a range of 1 to 0.1 to 1 to 10 in terms of mass ratio. Furthermore, the resin composition in any one of Claims 1-5 containing an organic solvent. Furthermore, the resin composition in any one of Claims 1-6 containing a hardening | curing agent.