JP7501130B2 - Lipid Microparticles - Google Patents

Description

The present invention relates to lipid microparticles containing a catalyst and a method for producing the same.

Two-liquid resin compositions containing a base resin and a curing agent have been widely used. Examples include adhesives containing epoxy resin and an acid anhydride curing agent, and paints containing polyol resin and a polyisocyanate curing agent. These two-liquid resin compositions are generally mixed immediately before use, and after work such as application to a substrate is performed, the curing reaction progresses over time, resulting in the desired function. In order to complete the curing reaction in a short time and prevent problems caused by insufficient curing, the addition of a catalyst or heat treatment is widely used to promote the reaction. Heat treatment is difficult in terms of equipment, for example, when working outdoors, and energy consumption is unavoidable, so the addition of a catalyst is a particularly important method for promoting the curing reaction.

However, problems are also known that result from the addition of catalysts. For example, in the case of paint, when a compound is prepared by adding a base agent, a curing agent, and a catalyst, a curing reaction progresses in the compound, causing the viscosity to increase, which can lead to the problem that in some cases the compound cannot be used in its entirety. In general, the time that a compound can be used after it has been prepared is called its pot life. In the past, efforts have been made to reduce catalytic activity and the amount of catalyst used in order to achieve both curability and pot life, but because there is a trade-off between the two, it has been difficult to achieve both. As a way to solve this problem, latent catalysts, whose catalytic activity is only expressed when a specific stimulus is applied, have been investigated.

As a latent catalyst, decomposition type catalysts, which undergo a decomposition reaction within the molecule due to a stimulus such as heat and thus exhibit catalytic activity, have been actively studied in the past, but the problem is that high temperatures and a long time are required for the decomposition reaction. For example, Patent Document 1 reports a thermal decomposition type catalyst in which a metal catalyst is reacted with a diamine compound in advance to form a complex, blocking the catalytically active sites, and the catalytically active sites are regenerated by a decomposition reaction of the complex due to heat. When using this catalyst, which requires the decomposition reaction of the latent catalyst, the curing reaction of the two-component resin composition requires a high-temperature and long-term heat treatment of 150°C for 1 hour, which causes the problem of not being able to achieve fast curing.

Another method is to encapsulate the catalyst by covering it with a resin, and release the encapsulated compound when the capsule undergoes changes such as swelling or destruction in response to an external stimulus.

Patent Document 2 reports a method for encapsulating the catalyst by adding a solution of an organometallic complex catalyst and polystyrene resin to an aqueous solution and precipitating the polystyrene resin, with the aim of achieving both resin polymerizability and pot life. This method has the problem that the reaction proceeds even at room temperature without the application of heat stimulation.

Although there have been attempts to prepare aqueous dispersions of encapsulated catalysts using emulsion polymerization, there have been no attempts to powder them and use them in a solvent-free system.

Patent Document 3 reports a method of preparing an encapsulated catalyst by emulsion polymerization and using it in water-based paints, but the encapsulated catalyst has not been powdered or applied to solvent-free systems. If moisture is present in the curing system, for example, when an epoxy resin is used, the catalyst is deactivated or the pot life is shortened due to the water acting as a catalyst, and when a polyisocyanate curing agent is used, there is a problem of reaction between the water and the isocyanate in the curing agent. Therefore, it was not possible to apply an aqueous dispersion of the encapsulated catalyst to a solvent-free system without special treatment such as powderization.

Another encapsulation method is the encapsulation technology that uses lipids as the capsule wall material. These lipid capsules have been developed mainly in the field of drug delivery systems (DDS) for delivering medicines to specific locations in the body (Non-Patent Document 1). This is because they have the advantages of reducing toxicity to the organism to which they are administered by using lipids present in the body as the wall material, and of being able to disperse in water even if the medicine is a hydrophobic substance due to the interfacial structure with hydrophilic and hydrophobic groups in the molecule. Although the latter advantage is also useful industrially, no encapsulation catalysts using lipids have been developed so far. The reason for this is that it is widely known that residual lipids in resins have a negative effect on physical properties. For example, Non-Patent Document 2 shows that oleic acid, a type of lipid, has a negative effect on synthetic leather made of polyurethane resin.

JP 2008-272673 A JP 2016-204428 A JP 2005-76011 A

Drug Delivery System 2002 17 314 Textile Product Consumption Science 2002 43 89

The present invention aims to provide lipid microparticles containing a catalyst that exhibits good thermal responsiveness and can achieve both curability and pot life, and a method for producing the same.

As a result of intensive research conducted by the inventors to solve the above problems, they discovered that microparticles obtained by covering a catalyst that accelerates the curing reaction of a two-component resin composition with a lipid exhibit good thermal stimulus response, which led to the completion of the present invention.

That is, the present invention includes the following embodiments:

Lipid microparticles characterized by encapsulating a catalyst within microparticles whose main component is lipid.

For the lipid microparticles of the present invention, it is preferred that the lipid is a (poly)glycerol fatty acid ester.

For the lipid microparticles of the present invention, it is preferred that the lipid is a monoglyceride.

For the lipid microparticles of the present invention, it is preferable that the melting point of the lipid is 40 to 120°C.

The lipid microparticles of the present invention preferably have an HLB value of 2.5 to 8.0.

For the lipid microparticles of the present invention, it is preferred that the catalyst is a Lewis acid.

For the lipid microparticles of the present invention, the catalyst is preferably a typical element compound.

For the lipid microparticles of the present invention, the catalyst is preferably a transition metal compound.

For the lipid microparticles of the present invention, it is preferable that the catalyst contains at least one selected from tin, titanium, and zirconium.

For the lipid microparticles of the present invention, it is preferable that the catalyst content of the lipid microparticles is 0.50 to 30% by mass.

The lipid microparticles of the present invention preferably have an average particle size of 1.0 to 1,000 μm.

The lipid microparticle composition of the present invention is characterized in that the lipid microparticles of the present invention are dispersed in a dispersion solvent. The dispersion solvent is preferably water.

The lipid microparticles of the present invention are preferably obtained by an emulsion method carried out at a temperature above the melting point of the lipid.

The coating composition, adhesive composition, and composition for artificial leather of the present invention are characterized by containing the lipid microparticles of the present invention.

The coating film of the present invention is characterized by being formed from any one of the coating composition, adhesive composition, and artificial leather composition of the present invention.

The article of the present invention is characterized by having the coating film of the present invention.

In the present invention, the main component is a component that accounts for 51% or more by mass of the components excluding the particulate catalyst.

According to the present invention, catalyst-encapsulated lipid microparticles that exhibit good thermal responsiveness can be obtained.

The lipid microparticles of the present invention are characterized by having a structure in which a catalyst is dispersed within the lipid microparticles.

The lipids of the present invention are not particularly limited, but examples thereof include (poly)glycerin fatty acid esters obtained by binding (poly)glycerin to fatty acids via ester bonds. Examples of (poly)glycerin fatty acid esters include triglycerides, diglycerides, and monoglycerides, depending on the number of ester bonds between the hydroxyl groups in (poly)glycerin and the fatty acids. These may be used alone, or two or more types may be used in combination.

Examples of fatty acids in (poly)glycerin fatty acid esters include saturated fatty acid bones such as methanoic acid, ethanoic acid, propanoic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, and triacontanoic acid. Examples of such fatty acids include fatty acids having an unsaturated fatty acid skeleton such as 9-hexadecenoic acid, cis-9-octadecenoic acid, 11-octadecenoic acid, cis,cis-9,12-octadecanetrienoic acid, 9,12,15-octadecanetrienoic acid, 6,9,12-octadecatrienoic acid, 9,11,13-octadecatrienoic acid, 8,11-eicosadienoic acid, 5,8,11-eicosatrienoic acid, 5,8,11-eicosatetraenoic acid, and cis-13-tricosanoic acid, and fatty acids having a functional group on the carbon chain such as 12-hydroxystearic acid. These may be contained alone or in combination of two or more types in the skeleton of one molecule of the (poly)glycerin fatty acid ester.

From the viewpoint of achieving both thermal responsiveness and pot life, the melting point of the lipid is preferably 40 to 120°C, more preferably 55 to 90°C, and most preferably 60 to 85°C.

From the viewpoint of dispersion stability, the HLB value of the lipid is preferably 2.5 to 8.0, more preferably 3.0 to 6.0, and most preferably 3.0 to 4.5.

From the viewpoint of suppressing the bleeding out of lipids from the cured material after curing, the (poly)glycerin fatty acid ester species is preferably diglyceride or monoglyceride, and monoglyceride is most preferred.

The catalyst of the present invention is not particularly limited, and examples thereof include Lewis acids such as typical element compounds, such as complexes, salts, and halides containing typical elements, and transition metal compounds, such as complexes, salts, and halides containing transition metals.

As typical elements contained in the typical element compound, from the viewpoint of catalytic activity, tin, aluminum, zinc, magnesium, bismuth, and gallium are preferred, tin, aluminum, zinc, magnesium, and bismuth are more preferred, and tin and bismuth are most preferred. Specific typical element compounds include tin compounds such as dimethyltin diacetate, dibutyltin diacetate, dioctyltin diacetate, dimethyltin dilaurate, dibutyltin dilaurate, dioctyltin dilaurate, and di-n-octyltin maleate.

From the viewpoint of catalytic activity, the transition metals contained in the transition metal compound are preferably titanium, zirconium, iron, ruthenium, hafnium, indium, scandium, lanthanum, chromium, copper, manganese, molybdenum, ruthenium, holmium, erbium, and ytterbium, more preferably titanium, zirconium, iron, ruthenium, hafnium, indium, scandium, lanthanum, chromium, copper, manganese, molybdenum, and ruthenium, and most preferably titanium and zirconium. Specific examples of the transition metal compound include titanium alkoxides such as tetraisopropyl titanate, tetranormal butyl titanate, tetra-tert-butyl titanate, tetraoctyl titanate, tetrakis(2-ethylhexyloxy)titanium, tetrastearyl titanate, isopropoxy(2-ethyl-1,3-hexanediolate)titanium, butyl titanate dimer diisopropoxybis(triethanolaminato)titanium, and dinormal butoxybis(triethanolaminato)titanium, trinormal butoxytitanium monostearate, diisopropoxytitanium alkoxides such as tetraisopropoxytitanium alkoxides, di ... Examples of the titanium compounds include titanium acylates such as titanium dioxide distearate, titanium stearate, titanium isostearate, diisopropoxy titanium diisostearate, and (2-n-butoxycarbonylbenzoyloxy)tributoxy titanium; zirconium alkoxides such as tetra-n-propyl zirconate and tetra-n-butyl zirconate; zirconium acylates such as zirconium octylate, zirconium stearate, and monobutoxy zirconium (IV) triisopropyl stearate; and the like. These may be used alone or in combination of two or more.

Among these, from the viewpoint of hydrolysis resistance, di-n-octyltin maleate, dimethyltin dilaurate, dibutyltin dilaurate, dioctyltin dilaurate, titanium stearate, titanium isostearate, zirconium octylate, zirconium stearate, and monobutoxyzirconium (IV) triisopropyl stearate are preferred, dibutyltin dilaurate, dioctyltin dilaurate, titanium stearate, titanium isostearate, zirconium octylate, zirconium stearate, and monobutoxyzirconium (IV) triisopropyl stearate are more preferred, and dioctyltin dilaurate, titanium stearate, and monobutoxyzirconium (IV) triisopropyl stearate are most preferred.

In addition, in the manufacturing process of the lipid microparticle composition of the present invention, it is preferable to use a dispersion solvent, a surfactant, and a neutralizing agent in addition to the lipid microparticles.

Examples of dispersion solvents include, but are not limited to, aromatic hydrocarbon solvents such as toluene, ethylbenzene, trimethylbenzene, and xylene; aliphatic hydrocarbon solvents such as pentane, hexane, and cyclohexane; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; alcohol solvents such as methanol, ethanol, isopropanol, ethylene glycol, diethylene glycol, triethylene glycol, and propylene glycol; glycol ether solvents such as methyl cellosolve, ethyl cellosolve, butyl cellosolve, methyl diglycol, ethyl diglycol, butyl diglycol, and propylene glycol monomethyl ether; ester solvents such as ethyl acetate, butyl acetate, and propylene glycol monomethyl ether acetate; amide solvents such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ether solvents such as diethyl ether and tetrahydrofuran; and water. These may be used alone or in combination of two or more.

When a solvent is used in the production process of lipid microparticles of the present invention, the content of lipid microparticles in the dispersion may be selected according to the dispersibility of the lipid microparticles and is not particularly limited, but is preferably 1.0 to 10,000 parts by mass, more preferably 5.5 to 1,900 parts by mass, and most preferably 11 to 900 parts by mass, per 100 parts by mass of dispersion. If the content is less than 1.0 part by mass, the lipid microparticles may not be sufficiently dispersed, and if it exceeds 10,000 parts by mass, it may be less economical.

The surfactant is not particularly limited, but examples thereof include sulfate ester-type anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene styrenated phenyl ether sulfates, polyoxyalkylene decyl ether sulfates, polyoxyalkylene isodecyl ether sulfates, polyoxyalkylene tridecyl ether sulfates, polyoxyethylene lauryl ether sulfates, polyoxyethylene ether sulfates, and polyoxyethylene oleyl cetyl ether sulfates; polyoxyethylene tridecyl ether phosphates, polyoxyethylene styrenated phenyl ether phosphates, polyoxyalkylene decyl ether phosphates, polyoxyalkylene decyl ether phosphate salts, polyoxyethylene lauryl ether phosphates, and polyoxyethylene lauryl ether phosphates. anionic surfactants of phosphate ester type such as ester salts, polyoxyethylene alkyl ether phosphate esters, and alkyl phosphate ester salts; anionic surfactants of carboxylic acid type such as polyoxyethylene lauryl ether acetate, lauryl sulfosuccinate, polyoxyethylene lauryl sulfosuccinate, polyoxyethylene alkyl sulfosuccinate, higher fatty acid salts, and naphthenate salts; anionic surfactants of sulfonic acid type such as linear alkylbenzene sulfonate, alkylbenzene sulfonic acid, α-olefin sulfonate, phenol sulfonic acid, dioctyl sulfosuccinate, lauryl sulfate, alkylnaphthalene sulfonate, salts of naphthalene sulfonic acid, formalin polycondensates, condensates of higher fatty acids and amino acids, acylated peptides, and N-acylmethyltaurine (cations of the above anionic surfactants include, for example, H ⁺ , Na ⁺ , K ⁺ , Li ⁺ , NH ₄ ⁺ , ethanolamine, etc.), nonionic surfactants such as alkyl glucosides, alkyl thioglucosides, N-D-gluco-N-methyl alkanamides, polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyoxyethylene fatty acid esters, polyoxyethylene sorbitol esters, and polyoxyethylene cetyl ethers may be used alone or in combination of two or more. Among these, from the viewpoint of dispersion stability during the production process, anionic surfactants are preferred, sulfate ester-type anionic surfactants are more preferred, and polyoxyethylene alkyl ether sulfates are most preferred.

When a surfactant is used in the manufacturing process of the lipid microparticles of the present invention, its content is not particularly limited, but is preferably an amount that is 0.10 to 10 times the critical micelle concentration of the surfactant, more preferably an amount that is 0.3 to 8 times, and most preferably 0.5 to 6 times. If the amount is less than 0.10 times, there is a risk that the polyvinyl resin microparticles cannot be dispersed, and if the amount exceeds 10 times, there is a risk that it will be less economical.

Neutralizing agents are not particularly limited, but examples include sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, calcium carbonate, sodium acetate, sodium hydroxide, potassium hydroxide, sodium dihydrogen phosphate, potassium dihydrogen phosphate, 3-(N-morpholino)propanesulfonic acid, methyl-3-aminopropanesulfonic acid, 2-(cyclohexylamino)ethanesulfonic acid, etc. These may be used alone or in combination of two or more.

When a neutralizing agent is used in the manufacturing process of the lipid microparticles of the present invention, its content is not particularly limited, but it is preferable to add it so that the pH of the lipid microparticle dispersion is 1.0 or more and 11.0 or less. If the pH of the lipid microparticles is less than 1.0 or exceeds 11.0, the dispersion stability may deteriorate.

The catalyst content in the lipid microparticles of the present invention is not particularly limited, but is preferably 0.10 to 30% by mass, more preferably 3.0 to 20% by mass, and most preferably 5.0 to 15% by mass. If the catalyst content is less than 0.10% by mass, the rapid curing property may be deteriorated, and if the catalyst content exceeds 30% by mass, the storage stability may be deteriorated.

The average particle size of the lipid microparticles of the present invention is not particularly limited, but is preferably 1.0 to 1,000 μm, more preferably 10 to 750 μm, and most preferably 100 to 500 μm. If the average particle size is less than 1.0 μm, handling may be impaired, and if it exceeds 1,000 μm, the particle size of the resulting aggregates may become large, resulting in reduced catalytic activity.

The resin composition containing the lipid microparticles of the present invention has good storage stability and thermal responsiveness.

Examples of resin compositions include two-liquid resin compositions that require a curing reaction when used, or one-liquid resin compositions that are capable of self-crosslinking. Resins are not particularly limited, but examples include epoxy resins, polyurethane resins, polyurethane urea resins, acrylic resins, acrylic silicone resins, alkyd resins, polyester resins, and melamine resins. These resins may be used alone or in combination of two or more. Among these, epoxy resins, polyurethane resins, polyurethane urea resins, acrylic resins, and melamine resins are preferred from the viewpoint of dispersibility of polyvinyl resin fine particle aggregates, and epoxy resins, polyurethane resins, and acrylic resins are more preferred.

The coating film obtained from the resin composition containing lipid microparticles is formed from the resin composition containing lipid microparticles of the present invention. The method for forming a resin coating film using the resin composition containing lipid microparticles of the present invention is not particularly limited, but examples thereof include a method in which the resin composition containing lipid microparticles of the present invention is applied to at least one surface of a substrate and then dried.

Methods for applying the resin composition containing the lipid microparticles of the present invention are not particularly limited, but examples include applicator method, bar coating method, spin coating method, spray coating method, dip coating method, nozzle coating method, gravure coating method, reverse roll coating method, die coating method, air doctor coating method, blade coating method, rod coating method, curtain coating method, knife coating method, transfer roll coating method, squeeze coating method, impregnation coating method, kiss coating method, calendar coating method, extrusion coating method, etc.

The drying temperature is not particularly limited, but is preferably 40 to 300°C, more preferably 55 to 150°C, and most preferably 60 to 140°C. If the drying temperature is less than 40°C, the catalyst-encapsulating lipid microparticles may not dissolve and rapid curing may not be achieved, and if it exceeds 300°C, the coating film may thermally decompose regardless of the type of resin. In addition, the drying time is not particularly limited, but is preferably 5 seconds to 10 days, and more preferably 20 to 6,000 seconds. If the drying time is less than 5 seconds, there is a risk of insufficient drying, and if it exceeds 10 days, the time required for the process will be long, which is not preferable from the standpoint of productivity.

The thickness of the coating film formed from the resin composition containing lipid microparticles is not particularly limited, but is preferably 5.0 to 300 μm, and more preferably 10 to 200 μm. If the thickness is less than 5.0 μm, sufficient coating film properties may not be obtained, and if it exceeds 300 μm, peeling may occur due to internal stress.

The resin composition containing the lipid microparticles thus obtained can be preferably used in paints, adhesives, artificial leather, etc.

In addition, articles having coating films obtained from these paints, adhesives, artificial leathers, etc. can be suitably used for vehicle-related parts, electronic materials, structural materials, building materials, furniture, decorative sheets, sporting goods, stationery, etc.

The following describes examples of the present invention, but the present invention is not limited to these examples. Unless otherwise specified, percentages are based on mass.

Example 1
Lipid microparticles were produced and their physical properties were evaluated by the following methods. The results are shown in Table 1.

<Production of lipid microparticles>
A 2L four-necked separable flask equipped with a stirrer, a thermometer, a heating device, and a reflux tube was charged with 1620 g of water at room temperature, and then heated to 80 ° C. A 300 mL beaker was charged with 162 g of glycerin monostearate and 18.0 g of dioctyltin dilaurate as a catalyst, each at room temperature. These were heated until dissolved under 80 ° C. conditions, and then stirred to homogenize, to obtain an organic layer. The organic layer was transferred to a separable flask containing a water layer, and stirred at a stirring speed of 250 rpm for 10 minutes under 80 ° C. conditions to obtain an emulsion. Subsequently, the mixture was cooled while stirring at a stirring speed of 100 rpm in an ice bath, and stirred for 1 hour while maintaining the liquid temperature at 20 ° C. or less to obtain a lipid microparticle composition encapsulating a catalyst. The obtained lipid microparticle composition was subjected to solid-liquid separation by suction filtration using a Buchner funnel, and the solid content was dried under reduced pressure at 50 ° C. conditions for 3 hours using an evaporator to obtain lipid microparticles. The lipid microparticle composition and lipid microparticles obtained as above were subjected to the following measurements and evaluations. The results are shown in Table 1.

<Measurement of catalyst content>
The catalyst content of the obtained lipid microparticles was measured using a scanning electron microscope (SEM) equipped with an energy dispersive X-ray analyzer (EDS) (FE-SEM JSM-7100F/EDS JED-2300 manufactured by JEOL Ltd.). As a pretreatment, a sample stained with ruthenium was embedded in epoxy resin, and then a cross section of the sample was cut out with a microtome. The cross section of the sample was measured with EDS, and the catalyst content was measured by quantifying the Sn content.

<Measurement of average particle size>
The average particle size of the obtained lipid microparticle composition was measured using a particle size distribution measuring device (MT3300EXII manufactured by Microtrack Bell). Water was used as the dispersion solvent. The volume average diameter value obtained by the measurement was taken as the measured value of the average particle size.

<Evaluation of Gel Time>
An isocyanate curing agent (product name: C-2612, manufactured by Tosoh Corporation) and a polyol resin (product name: NSP-112, manufactured by Tosoh Corporation) were mixed so that the functional group equivalent ratio was isocyanate group/hydroxyl group = 1.0/1.0. The lipid fine particles or catalyst alone were added to the obtained mixed resin and mixed until uniformly dispersed or dissolved to obtain a liquid sample for measuring gel time. Here, the amount of catalyst used was 0.30 parts by mass per 100 parts by mass of the mixed resin in the case of lipid fine particles, and 0.030 parts by mass per 100 parts by mass of the mixed resin in the case of catalyst alone. 1 mL of the sample was added to a heated metal cup and heated for 60 minutes. During heating, the properties of the sample were visually confirmed every minute, and the time when it changed from liquid to gel was recorded as the gel time. The liquid at the time of 60 minutes was considered to be uncured. The heating temperature was performed at two levels, 40 ° C. and 140 ° C., and the gel time was measured for each level. If the gel time at 40° C. is 60 minutes or more and the gel time at 140° C. is less than 8 minutes, it can be said to be good.

Example 2
A 2L four-necked separable flask equipped with a stirrer, a thermometer, a heating device, and a reflux tube was charged with 1620 g of water at room temperature, and then heated to 80 ° C. A 300 mL beaker was charged with 162 g of glycerin monostearate and 18.0 g of dioctyltin dilaurate, each at room temperature. These were heated until dissolved under 80 ° C. conditions, and then stirred to homogenize, to obtain an organic layer. The organic layer was transferred to a separable flask containing a water layer, and stirred at a stirring speed of 250 rpm for 10 minutes under 80 ° C. conditions to obtain an emulsion. Subsequently, the mixture was cooled while stirring at a stirring speed of 100 rpm in an ice bath, and stirred for 1 hour while maintaining the liquid temperature at 20 ° C. or less to obtain a lipid microparticle composition encapsulating a catalyst. The obtained lipid microparticle composition was subjected to suction filtration through a Buchner funnel to perform solid-liquid separation, and the solid content was dried under reduced pressure at 50 ° C. using an evaporator for 3 hours to obtain lipid microparticles. The lipid microparticle composition and lipid microparticles were evaluated in the same manner as in Example 1. The results are shown in Table 1.

Example 3
A 2L four-necked separable flask equipped with a stirrer, a thermometer, a heating device, and a reflux tube was charged with 1620 g of water at room temperature, and then heated to 95 ° C. A 300 mL beaker was charged with 162 g of glycerin monostearate and 18.0 g of dioctyltin dilaurate, each at room temperature. These were heated until dissolved under 95 ° C. conditions, and then stirred to homogenize, to obtain an organic layer. The organic layer was transferred to a separable flask containing a water layer, and stirred at a stirring speed of 250 rpm for 10 minutes under 95 ° C. conditions to obtain an emulsion. Subsequently, the mixture was cooled while stirring at a stirring speed of 100 rpm in an ice bath, and stirred for 1 hour while maintaining the liquid temperature at 20 ° C. or less to obtain a lipid microparticle composition encapsulating a catalyst. The obtained lipid microparticle composition was subjected to suction filtration with a Buchner funnel to perform solid-liquid separation, and the solid content was dried under reduced pressure at 50 ° C. using an evaporator for 3 hours to obtain lipid microparticles. The lipid microparticle composition and lipid microparticles were evaluated in the same manner as in Example 1. The results are shown in Table 1.

(Comparative Example 1)
Gel times were evaluated using dioctyltin dilaurate as a catalyst, and the results are shown in Table 1.

(Comparative Example 2)
The gel time was evaluated without using a catalyst, and the results are shown in Table 1.

Glycerin monostearate: Trade name: Rikemal S-100, manufactured by Riken Vitamin Co., Ltd., melting point 63-68°C, HLB value 4.3
Glycerin monobehenate: Trade name: Rikemal B-100, manufactured by Riken Vitamin Co., Ltd., melting point: 75-85°C, HLB value: 4.2
-Dioctyltin dilaurate: Manufactured by Kishida Chemical Co., Ltd.

As is clear from Table 1, according to the present invention, it is possible to obtain catalyst-encapsulated lipid microparticles that exhibit good thermal responsiveness and can achieve both curability and pot life.

Claims (14)

The catalyst is encapsulated in fine particles whose main component is lipid .
The catalyst contains at least one selected from tin, titanium, and zirconium;
The lipid microparticles have a particle size of 1.0 to 1,000 μm;
The lipid microparticles are characterized in that the melting point of the lipid is 40 to 120°C . The lipid microparticle according to claim 1, characterized in that the lipid is a (poly)glycerol fatty acid ester. The lipid microparticle according to claim 1 or 2, characterized in that the lipid is a monoglyceride. The lipid microparticle according to any one of claims 1 to 3, characterized in that the HLB value of the lipid is 2.5 to 8.0. 5. The lipid microparticle according to claim 1, wherein the catalyst content in the lipid microparticle is 0.50 to 30% by mass. A lipid microparticle composition comprising the lipid microparticle according to any one of claims 1 to 5 dispersed in a dispersion solvent. 7. The lipid microparticle composition according to claim 6, characterized in that the dispersion solvent for dispersing the lipid microparticles is water. A resin composition comprising the lipid microparticle or lipid microparticle composition according to any one of claims 1 to 7 . A method for producing lipid microparticles, comprising the steps of: obtaining the lipid microparticles according to any one of claims 1 to 8 by an emulsion method carried out at a temperature equal to or higher than the melting point of the lipid. A coating composition comprising the resin composition according to claim 8 . An adhesive composition comprising the resin composition according to claim 8 . A composition for artificial leather comprising the resin composition according to claim 8 . A coating film obtained from the composition according to any one of claims 8 to 12 . An article having the coating of claim 13 .