Resin particles

Abstract

To provide a resin particle with high flowability.SOLUTION: A resin particle includes a mother particle containing a biodegradable resin, and a coating layer containing at least one selected from the group consisting of a quaternary ammonium salt-containing polymer, a polyacrylamide, a polyvinylpyrrolidone, and a polylysine on the surface of the mother particle.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to resin particles. [Background technology]

[0002] Patent Document 1 proposes "a cellulose material whose biodegradability has been improved by coating it with a water-soluble polymer." Patent Document 2 proposes "a cosmetic method for changing the appearance of the skin, changing the feel of the skin, and / or protecting the skin, the cosmetic method comprising the step of applying to the skin a self-supporting cosmetic sheet comprising at least one biocompatible and / or biodegradable hydrophobic polymer layer, wherein the self-supporting cosmetic sheet has a thickness of 10 to 1000 nm, preferably 30 to 500 nm, and more preferably 50 to 300 nm." [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2004-256579 [Patent Document 2] Special Publication No. 2015-512863 Summary of the Invention [Problem to be solved by the invention]

[0004] The object of the present invention is to provide resin particles having base particles containing a biodegradable resin, which have high fluidity compared to resin particles in which the surface of the base particles is not modified or in which the dynamic friction coefficient exceeds 0.5. [Means for solving the problem]

[0005] The above problems are solved by the following means: <1> Mother particles containing a biodegradable resin; Resin particles having, on the surface of the base particles, a coating layer containing at least one selected from the group consisting of a quaternary ammonium salt-containing polymer, polyacrylamide, polyvinylpyrrolidone, and polylysine. <2> The quaternary ammonium salt-containing polymer is at least one selected from the group consisting of polyquaternium-6, polyquaternium-7, polyquaternium-51, polyquaternium-61, and polyquaternium-64. <1> The resin particles according to claim 1. <3> The biodegradable resin is at least one selected from the group consisting of cellulose acylate and polyester. <1> or <2> The resin particles according to claim 1. <4> The biodegradable resin is cellulose acylate. <1> ~ <3> 10. The resin particles according to any one of the above items. <5> The cellulose acylate is at least one selected from the group consisting of cellulose acetate, cellulose acetate propionate, and cellulose acetate butyrate. <4> The resin particles according to claim 1. <6> The base particles contain a plasticizer. <1> ~ <5> 10. The resin particles according to any one of the above items. <7> The plasticizer is at least one of an ester compound and a cardanol compound. <6> The resin particles according to claim 1. <8> The amount of the surface coating layer is 0.01% by mass or more and 20% by mass or less with respect to the base particles. <1> ~ <7> 10. The resin particles according to any one of the above items. <9> Mother particles containing a biodegradable resin; a coating layer on the surface of the base particle, Resin particles with a dynamic friction coefficient of 0.5 or less. <10> The above-mentioned cosmetic use <1> ~ <9> 10. The resin particles according to any one of the above items. [Effects of the Invention]

[0006] <1> or <3> According to the present invention, there is provided a resin particle having a base particle containing a biodegradable resin, which has high fluidity compared to a resin particle in which the surface of the base particle is not modified. <2> According to the invention, resin particles having high fluidity are provided compared to when the quaternary ammonium salt-containing polymer contained in the coating layer present on the surface of the base particles contains an alcohol structure. <4> According to the invention, resin particles having higher fluidity than when the biodegradable resin is polyester are provided. <5> According to the invention, resin particles having higher fluidity than those in which the cellulose acylate is a cellulose carbamate or a cellulose ether are provided.

[0007] <6> According to the invention, resin particles having higher fluidity than those in which the base particles contain only a biodegradable resin are provided. <7> According to the invention, resin particles having higher fluidity than those containing no plasticizer are provided. <8> According to the invention, resin particles having high fluidity are provided compared to when the amount of the coating layer on the surface of the base particles is less than 0.01% by mass or more than 20% by mass. <9> According to the present invention, resin particles having a base particle containing a biodegradable resin and a coating layer on the surface of the base particle are provided, which have high fluidity compared to resin particles having a dynamic friction coefficient of more than 0.5. <10> According to the present invention, resin particles suitable for cosmetic applications are provided. DETAILED DESCRIPTION OF THE INVENTION

[0008] Hereinafter, an embodiment of the present invention will be described. These descriptions and examples are intended to illustrate the embodiment and are not intended to limit the scope of the invention. In the present specification, the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range. In addition, in the present specification, the upper or lower limit of a numerical range may be replaced with a value shown in the examples.

[0009] Each component may contain multiple types of the corresponding substance. When referring to the amount of each component in a composition, if there are multiple substances corresponding to each component in the composition, the amount refers to the total amount of those multiple substances present in the composition, unless otherwise specified. In this specification, (meth)acrylic means both acrylic and methacrylic. In this specification, the term "process" includes not only an independent process but also a process that cannot be clearly distinguished from other processes, as long as the intended purpose of the process is achieved.

[0010] <Resin particles> The resin particles according to the first embodiment have base particles containing a biodegradable resin and a coating layer formed on the surface of the base particles and containing at least one selected from the group consisting of a quaternary ammonium salt-containing polymer, polyacrylamide, polyvinylpyrrolidone, and polylysine. The resin particles according to the first embodiment have improved fluidity due to the above-described configuration, and the reason for this is presumed to be as follows.

[0011] Resin particles containing a biodegradable resin (hereinafter also referred to as biodegradable resin particles) have sometimes had insufficient particle fluidity, which can lead to particle aggregation when used, for example, in cosmetics or as a resin filler.

[0012] The resin particles according to the first embodiment comprise base particles containing a biodegradable resin and a coating layer formed on the surface of the base particles, the coating layer containing at least one selected from the group consisting of a quaternary ammonium salt-containing polymer, polyacrylamide, polyvinylpyrrolidone, and polylysine. The presence of the coating layer tends to improve the lubricity of the resin particle surface. This tends to reduce friction between the resin particles, thereby improving the fluidity of the particles. From the above, it is presumed that the fluidity of the resin particles according to the first embodiment is improved.

[0013] The resin particles according to the second embodiment have base particles containing a biodegradable resin and a coating layer on the surface of the base particles, and have a dynamic friction coefficient of 0.5 or less. The resin particles according to the second embodiment have improved fluidity due to the above-described configuration, and the reason for this is presumed to be as follows.

[0014] The resin particles according to the second embodiment have a coating layer on the surface of the base particle, and have a dynamic friction coefficient of 0.5 or less. By setting the dynamic friction coefficient of the resin particles within the above range, the friction between the resin particles tends to decrease, and the fluidity of the particles tends to improve. From the above, it is presumed that the fluidity of the resin particles according to the second embodiment is improved.

[0015] Hereinafter, resin particles corresponding to either the resin particles according to the first or second embodiment will be described in detail, however, an example of the resin particles of the present invention may be any one of the resin particles according to the first or second embodiment.

[0016] (base particle) -Biodegradable resin- The base particles include a biodegradable resin. Examples of the base particles include particles containing a biodegradable resin as a main component, and specifically, examples include particles containing 90 mass%, 95 mass%, 98 mass%, or 100 mass% of biodegradable resin relative to the entire base particle. Here, biodegradable resin is a resin that can be decomposed into water and carbon dioxide by microorganisms. Specifically, biodegradable resin means a resin whose aerobic biodegradation rate measured according to ISO-14855-2 (2018) is 50% or more within one month.

[0017] Examples of biodegradable resins include cellulose acylate, polyester, and natural polymers.

[0018] Cellulose acylate is a cellulose derivative in which at least some of the hydroxyl groups in cellulose are substituted with acyl groups (acylation). An acyl group is a group consisting of -CO-R AC (R AC represents a hydrogen atom or a hydrocarbon group.) Examples of cellulose acylate include cellulose derivatives represented by the following general formula (CA).

[0019] Examples of polyesters include aliphatic polyesters and aliphatic aromatic polyesters. Examples of aliphatic polyesters include polylactic acid (PLA), polyglycolic acid (PGA), polyhydroxybutyrate, poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) (PHBH), polycaprolactone, polybutylene succinate (PBS), polybutylene succinate / adipate (PBSA), and polyethylene succinate (PBA), among other polyhydroxyalkanoates. Examples of the aliphatic aromatic polyester include polybutylene adipate / terephthalate copolymer resin (PBAH) and polytetramethylene adipate / terephthalate copolymer resin.

[0020] Examples of natural polymers include starch, cellulose, chitin, chitosan, gluten, gelatin, zein, soy protein, collagen, and keratin.

[0021] The biodegradable resin is preferably at least one selected from the group consisting of cellulose acylate and polyester, and more preferably cellulose acylate. By including the above-mentioned compound as the biodegradable resin, it becomes easier to react with the compound contained in the coating layer. Therefore, when the coating layer is formed, it is easier to form a more uniform film layer. Therefore, the fluidity of the resin particles is further improved. Furthermore, resin particles containing cellulose acylate as a biodegradable resin tend to have reduced particle fluidity, but for the reasons described above, the resin particles of this embodiment have improved fluidity even when they contain cellulose acylate as a biodegradable resin.

[0022] Cellulose acylate Cellulose acylate is, for example, a cellulose derivative represented by the following general formula (CA).

[0023] [ka]

[0024] In general formula (CA), A1, A2, and A3 each independently represent a hydrogen atom or an acyl group, and n represents an integer of 2 or greater. However, at least some of the n A1s, n A2s, and n A3s represent acyl groups. The n A1s in a molecule may be all identical, some identical, or different from one another. Similarly, the n A2s and n A3s in a molecule may be all identical, some identical, or different from one another.

[0025] The hydrocarbon group in the acyl group represented by A1, A2, and A3 may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.

[0026] The hydrocarbon group in the acyl group represented by A1, A2 and A3 may be a saturated hydrocarbon group or an unsaturated hydrocarbon group, but is more preferably a saturated hydrocarbon group.

[0027] The acyl group represented by A1, A2 and A3 is preferably an acyl group having a carbon number of 1 to 6. That is, the cellulose acylate is preferably an acyl group having a carbon number of 1 to 6.

[0028] The acyl group represented by A1, A2, and A3 may be a group in which a hydrogen atom in the acyl group is substituted with a halogen atom (e.g., a fluorine atom, a bromine atom, an iodine atom), an oxygen atom, a nitrogen atom, or the like, but is preferably unsubstituted.

[0029] Examples of the acyl group represented by A1, A2, and A3 include a formyl group, an acetyl group, a propionyl group, a butyryl group (butanoyl group), a propenoyl group, a hexanoyl group, etc. Among these, from the viewpoint of improving the biodegradation rate of the resin particles, the acyl group is more preferably an acyl group having from 2 to 4 carbon atoms, and even more preferably an acyl group having 2 or 3 carbon atoms.

[0030] Examples of cellulose acylate include cellulose acetate (cellulose monoacetate, cellulose diacetate (DAC), cellulose triacetate), cellulose acetate propionate (CAP), and cellulose acetate butyrate (CAB).

[0031] The cellulose acylate preferably has two or more types of acyl groups, from the viewpoint of improving the biodegradation rate of the resin particles. Specifically, from the viewpoint of improving the biodegradation rate of the resin particles, the cellulose acylate is preferably cellulose acetate, cellulose acetate propionate (CAP), or cellulose acetate butyrate (CAB), with cellulose acetate propionate (CAP) being more preferred.

[0032] By using at least one cellulose acylate selected from cellulose acetate, cellulose acetate propionate (CAP), and cellulose acetate butyrate (CAB), the cellulose acylate reacts more readily with the compound contained in the coating layer. This makes it easier to form a coating layer that is more uniform. This further improves the fluidity of the resin particles.

[0033] The cellulose acylate may be used alone or in combination of two or more kinds.

[0034] The weight average degree of polymerization of the cellulose acylate is preferably 200 or more and 1,000 or less, more preferably 500 or more and 1,000 or less, and even more preferably 600 or more and 1,000 or less.

[0035] The weight-average degree of polymerization of cellulose acylate is determined from the weight-average molecular weight (Mw) by the following procedure. First, the weight average molecular weight (Mw) of cellulose acylate is measured in polystyrene equivalent using tetrahydrofuran with a gel permeation chromatography device (GPC device: HLC-8320GPC manufactured by Tosoh Corporation, column: TSKgel α-M). Next, the degree of polymerization of cellulose acylate is calculated by dividing the molecular weight by the molecular weight of the constituent unit of cellulose acylate. For example, when the substituent of cellulose acylate is an acetyl group, the molecular weight of the constituent unit is 263 when the substitution degree is 2.4, and 284 when the substitution degree is 2.9.

[0036] From the viewpoint of improving the biodegradation rate of the resin particles, the substitution degree of cellulose acylate is preferably 2.1 to 2.9, more preferably 2.2 to 2.9, even more preferably 2.3 to 2.9, and particularly preferably 2.6 to 2.9.

[0037] In cellulose acetate propionate (CAP), the ratio of the substitution degree of acetyl groups to propionyl groups (acetyl groups / propionyl groups) is preferably 0.01 or more and 1 or less, more preferably 0.05 or more and 0.1 or less, from the viewpoint of improving the biodegradation rate of the resin particles.

[0038] In cellulose acetate butyrate (CAB), the ratio of the degree of substitution of acetyl groups to butyryl groups (acetyl groups / butyryl groups) is preferably 0.05 to 3.5, more preferably 0.5 to 3.0, from the viewpoint of improving the biodegradation rate of the resin particles.

[0039] The degree of substitution of cellulose acylate is an index showing the degree to which hydroxyl groups in cellulose are substituted with acyl groups. In other words, the degree of substitution is an index showing the degree of acylation of cellulose acylate. Specifically, the degree of substitution means the intramolecular average number of acyl groups replacing three hydroxyl groups in the D-glucopyranose unit of cellulose acylate. The degree of substitution is determined by the integral ratio of the peaks of cellulose-derived hydrogen and acyl group-derived hydrogen using 1H-NMR (JMN-ECA / JEOL RESONANCE).

[0040] These biodegradable resins may be used alone or in combination of two or more.

[0041] -Plasticizer- The base particles preferably contain a plasticizer. Plasticizers tend to contain functional groups that react easily with the compounds contained in the coating layer. Therefore, when the base particles contain a plasticizer, the compounds contained in the coating layer react not only with the biodegradable resin contained in the base particles but also with the plasticizer. Therefore, when the coating layer is formed, it is easier to form a more uniform film layer. Therefore, the fluidity of the resin particles is further improved.

[0042] Examples of plasticizers include ester compounds, cardanol compounds, camphor, metal soaps, polyols, and polyalkylene oxides. The plasticizer is preferably at least one of an ester compound and a cardanol compound. One type of plasticizer may be used alone, or two or more types may be used in combination.

[0043] By using at least one of an ester compound and a cardanol compound as a plasticizer, the plasticizer reacts more readily with the compounds contained in the coating layer. This makes it easier to form a more uniform coating layer when the coating layer is formed. This further improves the fluidity of the resin particles.

[0044] Examples of ester compounds include fatty acid esters (adipic acid esters, citrate esters, sebacate esters, azelaate esters, phthalate esters, and acetate esters), phosphate esters, condensed phosphate esters, glycol esters (e.g., glycol benzoate esters), and modified fatty acid esters (e.g., epoxidized fatty acid esters). Examples of the esters include monoesters, diesters, triesters, and polyesters. Among these, dicarboxylic acid diesters (e.g., adipic acid diesters, sebacic acid diesters, azelaic acid diesters, and phthalic acid diesters) are preferred.

[0045] The plasticizer is preferably at least one selected from the group consisting of an adipic acid ester, a citrate ester, and a sebacate ester. The adipic acid ester, the citrate ester, and the sebacate ester have high affinity with cellulose acylate, and are dispersed in the cellulose acylate in a nearly uniform state, so that they react more easily with the compound contained in the coating layer than other plasticizers.

[0046] The adipic acid ester may be a mixture of an adipic acid ester and other components, and examples of commercially available products of such mixtures include Daifatty 101 manufactured by Daihachi Chemical Industry Co., Ltd.

[0047] Examples of fatty acid esters such as citrate esters, sebacate esters, azelaate esters, phthalate esters, and acetate esters include esters of fatty acids and alcohols. Examples of the alcohols include monohydric alcohols such as methanol, ethanol, propanol, butanol, and 2-ethylhexanol; and polyhydric alcohols such as glycerin, polyglycerin (diglycerin, etc.), pentaerythritol, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, trimethylolpropane, trimethylolethane, and sugar alcohols.

[0048] Examples of the glycol in the glycol benzoate include ethylene glycol, diethylene glycol, and propylene glycol.

[0049] Epoxidized fatty acid esters are ester compounds having a structure in which the carbon-carbon unsaturated bonds of an unsaturated fatty acid ester have been epoxidized (i.e., oxacyclopropane). Examples of epoxidized fatty acid esters include esters of alcohols with fatty acids in which some or all of the carbon-carbon unsaturated bonds in unsaturated fatty acids (e.g., oleic acid, palmitoleic acid, vaccenic acid, linoleic acid, linolenic acid, nervonic acid, etc.) have been epoxidized. Examples of the alcohols include monohydric alcohols such as methanol, ethanol, propanol, butanol, and 2-ethylhexanol; and polyhydric alcohols such as glycerin, polyglycerin (e.g., diglycerin), pentaerythritol, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, trimethylolpropane, trimethylolethane, and sugar alcohols.

[0050] The molecular weight (or weight average molecular weight) of the ester compound as a plasticizer is preferably from 200 to 2000, more preferably from 250 to 1500, and even more preferably from 280 to 1000. Unless otherwise specified, the weight average molecular weight of the ester compound is a value measured in accordance with the method for measuring the weight average molecular weight of cellulose acylate.

[0051] It is also preferable to use a cardanol compound as the plasticizer. Cardanol compounds refer to components contained in naturally occurring compounds made from cashews (for example, compounds represented by the following structural formulas (b-1) to (b-4)) or derivatives of the above components.

[0052] [ka]

[0053] The cardanol compound may be a mixture of naturally occurring compounds made from cashews (hereinafter also referred to as a "cashew-derived mixture").

[0054] The cardanol compound may be a derivative of a cashew-derived mixture. Examples of the derivative of a cashew-derived mixture include the following mixtures and simple substances:

[0055] A mixture of cashew-derived ingredients with adjusted composition ratios A single substance isolated from a mixture of cashew-derived ingredients -Mixtures containing modified components of cashew-derived mixtures A mixture containing a polymer obtained by polymerizing components of a cashew-derived mixture A mixture containing a modified polymer obtained by modifying and polymerizing components in a cashew-derived mixture A mixture containing a modified substance obtained by further modifying the components in the mixture with the adjusted composition ratio. A mixture containing a polymer obtained by further polymerizing the components in the mixture with the adjusted composition ratio. A mixture containing a modified polymer obtained by further modifying and polymerizing the components in the mixture whose composition ratio has been adjusted. A denatured product obtained by further denaturing the isolated monomer A polymer obtained by further polymerizing the isolated monomer A modified polymer obtained by further modifying and polymerizing the isolated monomer. Here, the term "monomer" also includes multimers such as dimers and trimers.

[0056] From the viewpoint of improving the biodegradation rate of the resin particles, the cardanol compound is preferably at least one compound selected from the group consisting of compounds represented by general formula (CDN1) and polymers obtained by polymerizing compounds represented by general formula (CDN1).

[0057] [ka]

[0058] In the general formula (CDN1), R 1 R represents an alkyl group which may have a substituent, or an unsaturated aliphatic group which has a double bond and may have a substituent. 2 represents a hydroxy group, a carboxy group, an alkyl group which may have a substituent, or an unsaturated aliphatic group which has a double bond and may have a substituent. P2 represents an integer of 0 to 4. When P2 is 2 or more, a plurality of R 2 may be the same group or different groups.

[0059] In general formula (CDN1), R 1 The alkyl group represented by the formula (I) which may have a substituent is preferably an alkyl group having 3 to 30 carbon atoms, more preferably an alkyl group having 5 to 25 carbon atoms, and even more preferably an alkyl group having 8 to 20 carbon atoms. Examples of the substituent include a hydroxy group; a substituent containing an ether bond such as an epoxy group or a methoxy group; and a substituent containing an ester bond such as an acetyl group or a propionyl group. Examples of the alkyl group which may have a substituent include a pentadecane-1-yl group, a heptan-1-yl group, an octan-1-yl group, a nonan-1-yl group, a decan-1-yl group, an undecane-1-yl group, a dodecane-1-yl group, and a tetradecane-1-yl group.

[0060] In general formula (CDN1), R 1 The unsaturated aliphatic group represented by the formula (I) which has a double bond and which may have a substituent is preferably an unsaturated aliphatic group having 3 to 30 carbon atoms, more preferably an unsaturated aliphatic group having 5 to 25 carbon atoms, and even more preferably an unsaturated aliphatic group having 8 to 20 carbon atoms. The unsaturated aliphatic group preferably has 1 or more and 3 or less double bonds. Examples of the substituent include those listed above as the substituent of the alkyl group. Examples of the unsaturated aliphatic group having a double bond and optionally having a substituent include a pentadec-8-en-1-yl group, a pentadeca-8,11-dien-1-yl group, a pentadeca-8,11,14-trien-1-yl group, a pentadec-7-en-1-yl group, a pentadeca-7,10-dien-1-yl group, and a pentadeca-7,10,14-trien-1-yl group.

[0061] In general formula (CDN1), R 1 As the alkyl group, a pentadec-8-en-1-yl group, a pentadeca-8,11-dien-1-yl group, a pentadeca-8,11,14-trien-1-yl group, a pentadec-7-en-1-yl group, a pentadeca-7,10-dien-1-yl group, and a pentadeca-7,10,14-trien-1-yl group are preferred.

[0062] In general formula (CDN1), R 2 The alkyl group which may have a substituent and the unsaturated aliphatic group which has a double bond and may have a substituent represented by R 1 Similarly, preferred examples include those listed as the alkyl group which may have a substituent and the unsaturated aliphatic group which has a double bond and may have a substituent, represented by the formula (I) below.

[0063] The compound represented by general formula (CDN1) may be further modified, for example, epoxidized, and from the viewpoint of improving the biodegradation rate of the resin particles, it is preferably a compound having a structure in which the hydroxy group of the compound represented by general formula (CDN1) is replaced with the following group (EP), that is, a compound represented by the following general formula (CDN1-e):

[0064] [ka]

[0065] In the group (EP) and general formula (CDN1-e), L EP represents a single bond or a divalent linking group. 1 , R 2 and P2 are R in general formula (CDN1), 1 , R 2 and P2.

[0066] In the group (EP) and the general formula (CDN1-e), L EP Examples of the divalent linking group represented by include an alkylene group which may have a substituent (preferably an alkylene group having 1 to 4 carbon atoms, more preferably an alkylene group having 1 carbon atom), a -CH2CH2OCH2CH2- group, and the like. The above-mentioned substituents include R 1 The same can be mentioned as the substituents listed in the above.

[0067] L EP As the alkyl group, a methylene group is preferred.

[0068] The polymer obtained by polymerizing the compound represented by general formula (CDN1) refers to a polymer obtained by polymerizing at least two or more compounds represented by general formula (CDN1) with or without a linking group.

[0069] Examples of polymers obtained by polymerizing the compound represented by general formula (CDN1) include compounds represented by the following general formula (CDN2).

[0070] [ka]

[0071] In the general formula (CDN2), R 11 , R 12 and R 13 R each independently represents an alkyl group which may have a substituent, or an unsaturated aliphatic group which has a double bond and may have a substituent. 21 , R 22 and R 23 each independently represents a hydroxy group, a carboxy group, an alkyl group which may have a substituent, or an unsaturated aliphatic group which has a double bond and may have a substituent. P21 and P23 each independently represent an integer of 0 or more and 3 or less, and P22 represents an integer of 0 or more and 2 or less. L 1 and L 2 each independently represents a divalent linking group, and n represents an integer of 0 to 10. When P21 is 2 or more, a plurality of R 21 , when P22 is 2 or more, there are multiple R 22 , and when P23 is 2 or more, there are multiple R 23 may be the same or different groups. When n is 2 or more, a plurality of R 12 , R 22 and L 1 may be the same or different groups, and when n is 2 or greater, the number of P22s present may be the same or different.

[0072] In general formula (CDN2), R 11 , R 12 , R 13 , R 21 , R 22 and R 23 The alkyl group which may have a substituent and the unsaturated aliphatic group which has a double bond and may have a substituent represented by R 1The following are also preferred examples.

[0073] In general formula (CDN2), L 1 and L 2 Examples of the divalent linking group represented by include an alkylene group which may have a substituent (preferably an alkylene group having 2 to 30 carbon atoms, more preferably an alkylene group having 5 to 20 carbon atoms). The above-mentioned substituents include R 1 The same can be mentioned as the substituents listed in the above.

[0074] In formula (CDN2), n is preferably 1 or more and 10 or less, and more preferably 1 or more and 5 or less.

[0075] The compound represented by general formula (CDN2) may be further modified, for example, epoxidized, specifically a compound in which the hydroxy group of the compound represented by general formula (CDN2) is replaced with a group (EP), that is, a compound represented by the following general formula (CDN2-e):

[0076] [ka]

[0077] In the general formula (CDN2-e), R 11 , R 12 , R 13 , R 21 , R 22 , R 23 , P21, P22, P23, L 1 , L 2 and n are R in general formula (CDN2), 11 , R 12 , R 13 , R 21 , R 22 , R 23 , P21, P22, P23, L 1 , L 2 and n. In the general formula (CDN2-e), L EP1 , L EP2 and L EP3 each independently represents a single bond or a divalent linking group. When n is 2 or more, a plurality of L EP2 may be the same group or different groups.

[0078] In the general formula (CDN2-e), L EP1 , L EP2 and L EP3 Examples of the divalent linking group represented by include L in general formula (CDN1-e). EP Similarly, the divalent linking group represented by the formula (I) is preferably the same as the divalent linking group represented by the formula (I).

[0079] The polymer obtained by polymerizing the compound represented by general formula (CDN1) may be, for example, a polymer obtained by three-dimensionally crosslinking polymerizing at least three or more compounds represented by general formula (CDN1) with or without a linking group. Examples of the polymer obtained by three-dimensionally crosslinking polymerizing the compound represented by general formula (CDN1) include compounds represented by the following structural formula:

[0080] [ka]

[0081] In the above structural formula, R 10 , R 20 and P20 are R in general formula (CDN1), 1 , R 2 and P2. 10 represents a single bond or a divalent linking group. 10 , R 20 and L 10 may be the same or different groups. 20 may be the same or different numbers.

[0082] In the above structural formula, L 10Examples of the divalent linking group represented by include an alkylene group which may have a substituent (preferably an alkylene group having 2 to 30 carbon atoms, more preferably an alkylene group having 5 to 20 carbon atoms). The above-mentioned substituents include R 1 The same can be mentioned as the substituents listed in the above.

[0083] The compound represented by the above structural formula may be further modified, for example, may be epoxidized. Specifically, it may be a compound in which the hydroxy group of the compound represented by the above structural formula is replaced with a group (EP), for example, a compound represented by the following structural formula, that is, a polymer in which the compound represented by general formula (CDN1-e) is three-dimensionally crosslinked and polymerized.

[0084] [ka]

[0085] In the above structural formula, R 10 , R 20 and P20 are R in general formula (CDN1-e), 1 , R 2 and P2. 10 represents a single bond or a divalent linking group. 10 , R 20 and L 10 may be the same or different groups. 20 may be the same or different numbers.

[0086] In the above structural formula, L 10 Examples of the divalent linking group represented by include an alkylene group which may have a substituent (preferably an alkylene group having 2 to 30 carbon atoms, more preferably an alkylene group having 5 to 20 carbon atoms). The above-mentioned substituents include R 1The same can be mentioned as the substituents listed in the above.

[0087] From the viewpoint of improving the transparency of the resin molded body, the cardanol compound preferably contains a cardanol compound having an epoxy group, and is more preferably a cardanol compound having an epoxy group.

[0088] Commercially available cardanol compounds may be used. Examples of commercially available cardanol compounds include NX-2024, Ultra LITE 2023, NX-2026, GX-2503, NC-510, LITE 2020, NX-9001, NX-9004, NX-9007, NX-9008, NX-9201, and NX-9203 manufactured by Cardolite Corporation, and LB-7000, LB-7250, and CD-5L manufactured by Tohoku Kako Co., Ltd. Commercially available cardanol compounds having an epoxy group include NC-513, NC-514S, NC-547, LITE513E, and Ultra LTE 513 manufactured by Cardolite Corporation.

[0089] From the viewpoint of improving the biodegradation rate of a resin molded article, the hydroxyl value of the cardanol compound is preferably 100 mgKOH / g or more, more preferably 120 mgKOH / g or more, and even more preferably 150 mgKOH / g or more. The hydroxyl value of the cardanol compound is measured in accordance with Method A of ISO 14900.

[0090] When a cardanol compound having an epoxy group is used as the cardanol compound, from the viewpoint of improving the transparency of a resin molded product, the epoxy equivalent is preferably from 300 to 500, more preferably from 350 to 480, and even more preferably from 400 to 470. The epoxy equivalent of the cardanol compound having an epoxy group is measured in accordance with ISO 3001.

[0091] The molecular weight of the cardanol compound is preferably 250 or more and 1000 or less, more preferably 280 or more and 800 or less, and even more preferably 300 or more and 500 or less, from the viewpoint of improving the biodegradation rate of the resin molded article.

[0092] The cardanol compounds may be used alone or in combination of two or more.

[0093] The content of the plasticizer is preferably from 1% by mass to 50% by mass, and more preferably from 1% by mass to 30% by mass, based on the total biodegradable resin.

[0094] -Other ingredients- The base particles may contain other components. Examples of other components include plasticizers, flame retardants, compatibilizers, release agents, light resistance agents, weather resistance agents, colorants, pigments, modifiers, anti-drip agents, antistatic agents, hydrolysis inhibitors, fillers, reinforcing agents (glass fiber, carbon fiber, talc, clay, mica, glass flakes, milled glass, glass beads, crystalline silica, alumina, silicon nitride, aluminum nitride, boron nitride, etc.), acid acceptors for preventing acetic acid release (oxides such as magnesium oxide and aluminum oxide; metal hydroxides such as magnesium hydroxide, calcium hydroxide, aluminum hydroxide, and hydrotalcite; calcium carbonate; talc; etc.), and reactive trapping agents (for example, epoxy compounds, acid anhydride compounds, carbodiimides, etc.). The content of each of the other components is preferably 0% by mass or more and 5% by mass or less relative to the total amount of the base particles, where "0% by mass" means that no other components are included.

[0095] The base particles may contain other resins besides the biodegradable resin. However, if other resins are contained, the content of the other resins relative to the total amount of the base particles is preferably 5% by mass or less, and more preferably less than 1% by mass. It is more preferable that the base particles do not contain other resins (i.e., 0% by mass). Examples of other resins include conventionally known thermoplastic resins, specifically, polycarbonate resins; polypropylene resins; polyester resins; polyolefin resins; polyester carbonate resins; polyphenylene ether resins; polyphenylene sulfide resins; polysulfone resins; polyether sulfone resins; polyarylene resins; polyetherimide resins; polyacetal resins; polyvinyl acetal resins; polyketone resins; polyether ketone resins; polyether ether ketone resins; polyaryl ketone resins; polyether nitrile resins; liquid crystal resins; polybenzimidazole resins; polypa Examples of suitable resins include lavanic acid resins, vinyl polymers or copolymers obtained by polymerizing or copolymerizing one or more vinyl monomers selected from the group consisting of aromatic alkenyl compounds, methacrylic acid esters, acrylic acid esters, and vinyl cyanide compounds, diene-aromatic alkenyl compound copolymers, vinyl cyanide-diene-aromatic alkenyl compound copolymers, aromatic alkenyl compound-diene-vinyl cyanide-N-phenylmaleimide copolymers, vinyl cyanide-(ethylene-diene-propylene (EPDM))-aromatic alkenyl compound copolymers, vinyl chloride resins, and chlorinated vinyl chloride resins. These resins may be used alone or in combination of two or more.

[0096] (covering layer) The resin particles have a coating layer on the surface of the base particle, the coating layer containing at least one selected from the group consisting of a quaternary ammonium salt-containing polymer, polyacrylamide, polyvinylpyrrolidone, and polylysine.

[0097] The weight-average molecular weight of the quaternary ammonium salt-containing polymer, polyacrylamide, polyvinylpyrrolidone, and polylysine is preferably 4,000 or more, more preferably 40,000 or more, even more preferably 100,000 or more, and even more preferably 200,000 or more, and is preferably 3,000,000 or less, more preferably 2,000,000 or less, and even more preferably 1,000,000 or less. Here, the weight average molecular weight of the quaternary ammonium salt-containing polymer, polyacrylamide, polyvinylpyrrolidone, and polylysine is a value measured by gel permeation chromatography (GPC). The measurement is performed using a Tosoh GPC HLC-8120GPC, a Tosoh TSKgel SuperHM-M (15 cm) column, and THF solvent. The weight-average molecular weight is calculated from the measurement results using a molecular weight calibration curve created with monodisperse polystyrene standard samples.

[0098] The surface coverage of the coating layer is preferably 0.01% by mass to 20% by mass, more preferably 0.1% by mass to 10% by mass, and even more preferably 0.3% by mass to 5% by mass, based on the base particle. By setting the surface coverage amount of the coating layer within the above range, the lubricity of the resin particle surface is more likely to be improved, and the flowability of the resin particles is more improved.

[0099] Here, the surface coverage of the coating layer is measured as follows: The coverage of the cationic resin is determined by the difference between the treatment amount of at least one selected from the group consisting of a quaternary ammonium salt-containing polymer, polyacrylamide, polyvinylpyrrolidone, and polylysine (hereinafter also referred to as surface treatment polymer) and the surface treatment polymer obtained by drying the supernatant after treatment.

[0100] -Quaternary ammonium salt-containing polymer- Quaternary ammonium salt-containing polymers are NR4 + The term "polymer" refers to a polymer having a structural unit containing an atomic group represented by the following formula (wherein R represents the same or different hydrocarbon groups):

[0101] Examples of the quaternary ammonium salt-containing polymer include a homopolymer of dimethyldiallylammonium chloride, a copolymer of dimethyldiallylammonium chloride and a (meth)acrylic group-containing monomer, a homopolymer of 2-methacryloyloxyethyl phosphorylcholine, and a copolymer of 2-methacryloyloxyethyl phosphorylcholine and a (meth)acrylic group-containing monomer.

[0102] Examples of the (meth)acrylic group-containing monomer include (meth)acrylic acid esters, (meth)acrylamides, and (meth)acrylic acid.

[0103] The (meth)acrylic acid ester is preferably a (meth)acrylic acid alkyl ester, more preferably a (meth)acrylic acid alkyl ester having 2 or more and 25 or less carbon atoms in the (meth)alkyl group, more preferably a (meth)acrylic acid alkyl ester having 4 or more and 20 or less carbon atoms in the alkyl group, and even more preferably a (meth)acrylic acid alkyl ester having 10 or more and 19 or less carbon atoms in the alkyl group. Specific examples of the (meth)acrylic acid ester include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)methacrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, and isobornyl (meth)acrylate. The (meth)acrylic acid ester may be used alone or in combination of two or more kinds.

[0104] The mass proportion of the (meth)acrylic group-containing monomer in all the polymerization components of the copolymer of dimethyldiallylammonium chloride and a (meth)acrylic group-containing monomer and the copolymer of 2-methacryloyloxyethylphosphorylcholine and a (meth)acrylic group-containing monomer is preferably 10% by mass or more and 60% by mass or less, more preferably 15% by mass or more and 50% by mass or less, and even more preferably 20% by mass or more and 40% by mass or less.

[0105] The weight average molecular weight of the quaternary ammonium salt-containing polymer is preferably 50,000 or more, more preferably 100,000 or more, even more preferably 200,000 or more, and even more preferably 300,000 or more, and is preferably 3,000,000 or less, more preferably 2,000,000 or less, and even more preferably 1,000,000 or less. Here, the weight average molecular weight of the quaternary ammonium salt-containing polymer is a value measured by gel permeation chromatography (GPC).

[0106] The quaternary ammonium salt-containing polymer is preferably at least one selected from the group consisting of polyquaternium-6, polyquaternium-7, polyquaternium-51, polyquaternium-61, and polyquaternium-64. By using the above compound as the quaternary ammonium salt-containing polymer, the lubricity of the resin particle surface is more likely to be improved, and the flowability of the resin particles is more improved.

[0107] (Second layer) A compound layer may be provided on the coating layer (hereinafter also referred to as the first layer). When a compound layer is provided on the coating layer, the compound layer will be referred to as the second layer hereinafter. The second layer preferably contains an anionic or nonionic compound or a hydrophobic compound.

[0108] Examples of anionic or nonionic compounds or hydrophobic compounds include hydrophobic compounds having an anionic group (such as -COOH (carboxyl group), -SOH (sulfonic group)), and hydrophobic compounds having no cationic or anionic groups. The hydrophobic compound refers to a compound that imparts hydrophobicity (specifically, water contact angle) to the biodegradable resin particles described below.

[0109] Examples of the hydrophobic compound include a silicone compound, a hydrocarbon compound, a fatty acid compound, an acrylic resin, a polyester resin, and a urethane resin. Among these, at least one selected from the group consisting of silicone compounds, hydrocarbon compounds, fatty acid compounds, acrylic resins, polyester resins, and urethane resins is preferred.

[0110] Examples of silicone compounds include dimethylpolysiloxane, methylpolysiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentanesiloxane, methylcyclopolysiloxane, various modified silicone oils (alkyl-modified silicone oil, polyether-modified silicone oil, alcohol-modified silicone oil, fluorine-modified silicone oil, amino-modified silicone oil, etc.), MQ resin, and silicone rubber. Among these, the silicone compound is preferably at least one selected from the group consisting of dimethylpolysiloxane, methylpolysiloxane, MQ resin, and silicone rubber. Here, MQ resin refers to a silicone resin having M units, which are monofunctional siloxane units [(CH3)3SiO1 / 2], and Q units, which are tetrafunctional siloxane units [SiO4 / 2].

[0111] Commercially available silicone compounds include silicone compounds manufactured by Shin-Etsu Chemical Co., Ltd. (KM-902, KM-903, KM-910, KM-9729, POLON-MN-ST, KM-9737A, KM-9782, KM-9738A, KM-752T, POLON-MF-33, KM-9717, X-51-1302M (MQ resin), POLON-MF-56, KM-2002-L-1, KM-2002-T, KM-9772, KM-9749, POLON-MF-40, KM-9729, X-52-1133, etc.), and a silicone compound manufactured by Wacker Asahi Kasei Silicone Co., Ltd. (BELSIL DM3112VP).

[0112] Examples of hydrocarbon compounds include petroleum waxes (paraffin wax, microcrystalline wax, petrolatum wax, etc.) and synthetic hydrocarbon waxes (polyethylene wax, polypropylene wax, polybutene wax, Fischer-Tropsch wax, etc.). Among these, the hydrocarbon compound is preferably at least one selected from the group consisting of paraffin wax, microcrystalline wax, polyethylene wax, and polypropylene wax.

[0113] Commercially available hydrocarbon compounds include microcrystalline wax (EMUSTAR-0001, etc.) manufactured by Nippon Seiro Co., Ltd., paraffin wax (EMUSTAR-0135, etc.) manufactured by Nippon Seiro Co., Ltd., paraffin wax (AQUACER 497, etc.) manufactured by BYK Co., Ltd., polyethylene wax (AQUACER 507, AQUACER 840, AQUACER 1547, AQUACER 272, etc.) manufactured by BYK Co., Ltd., polyethylene wax (Hitec E-2213, Hitec E-6324, etc.) manufactured by Toho Chemical Industry Co., Ltd., polypropylene wax (AQUACER 593, etc.) manufactured by BYK Co., Ltd., and polypropylene (Hitec P-9018, Hitec P-5060P, etc.) manufactured by Toho Chemical Industry Co., Ltd.

[0114] Examples of fatty acid compounds include vegetable oils containing fatty acids (castor oil, tung oil, linseed oil, shortening, corn oil, soybean oil, sesame oil, rapeseed oil, sunflower oil, rice bran oil, camellia oil, coconut oil, palm oil, walnut oil, olive oil, peanut oil, almond oil, jojoba oil, cocoa butter, shea butter, neem oil, safflower oil, Japan wax, candelilla wax, rice wax, carnauba wax, etc.). Among these, from the viewpoint of improving the biodegradation rate over time and reducing the initial biodegradation rate, at least one wax selected from the group consisting of carnauba wax, rice wax, candelilla wax, palm wax, castor oil wax, soybean oil wax, and sunflower oil wax is preferred.

[0115] Commercially available fatty acid compounds include carnauba wax (EMUSTAR-0413 (carnauba wax)) manufactured by Nippon Seiro Co., Ltd., rice wax (AQUASPROUT-7300, etc.) manufactured by Nippon Seiro Co., Ltd., palm wax (AQUASPROUT-7100, etc.) manufactured by Nippon Seiro Co., Ltd., castor oil wax (AQUASPROUT-7500, etc.) manufactured by Nippon Seiro Co., Ltd., soybean oil wax (AQUASPROUT-7200, etc.) manufactured by Nippon Seiro Co., Ltd., sunflower oil wax (AQUASPROUT-7400, etc.) manufactured by Nippon Seiro Co., Ltd., and palm oil wax (Cuckoo Ace TKE, etc.) manufactured by Nippon Seiro Co., Ltd.

[0116] Examples of the acrylic resin include well-known acrylic resins such as polymers of acrylic acid and polymers of alkyl acrylate esters. Commercially available acrylic resins include, for example, acrylic resins manufactured by Taisei Fine Co., Ltd. (3WX-2015, 3MF-320, 3MF-333, 3MF-407, etc.) and acrylic resins manufactured by DIC Corporation (COAT SFC-6440, BONCOAT CE-6270, BONCOAT CE-6400, BONCOAT CF-2800, etc.).

[0117] Examples of polyester resins include well-known polyester resins such as polycondensates of polycarboxylic acids and polyhydric alcohols, and ring-opening polycondensates of cyclic lactams. Commercially available polyester resins include, for example, polyester resins manufactured by Takamatsu Oil & Fat Co., Ltd. (A-110F, A-160P, A-520, A-613D, A-615GE, A-640, A-645GH, A-647GEX, etc.).

[0118] Examples of the urethane resin include well-known urethane resins such as polyester-based polyurethane, polyether-based polyurethane, polycarbonate-based polyurethane, etc. Furthermore, as the urethane resin, a material having a urethane polymer shell layer around an acrylic polymer core may be used. Commercially available urethane resins include, for example, urethane resins manufactured by Taisei Fine Co., Ltd. (WEM-031U, WEM-200U, WEM-321U, WEM-3000, WBR-016U, WBR-2101, etc.).

[0119] -Content of each layer- In the biodegradable resin particles according to this embodiment, the mass ratio of the coating amount of the cationic resin in the first layer to the coating amount of the hydrophobic compound in the second layer (coating amount of the cationic resin / coating amount of the hydrophobic compound) is preferably 0.05 or more and 20 or less, more preferably 0.1 or more and 10 or less, and even more preferably 0.1 or more and 3 or less.

[0120] Furthermore, the content of the cationic resin relative to the base particle (the amount of the first layer coated relative to the entire base particle) is preferably 0.05% by mass or more and 15% by mass or less, more preferably 0.1% by mass or more and 10% by mass or less, and even more preferably 0.1% by mass or more and 3% by mass or less.

[0121] Furthermore, from the viewpoint of further improving storage stability in a solution containing water, the content of the hydrophobic compound relative to the base particle (the amount of coating by the second layer relative to the entire base particle) is preferably 0.05% by mass or more and 15% by mass or less, more preferably 0.1% by mass or more and 10% by mass or less, and even more preferably 0.1% by mass or more and 3% by mass or less.

[0122] Here, the coating amount of the second layer is measured as follows: The coating amount of the hydrophobic compound is determined as the difference between the treatment amount of the hydrophobic compound and the hydrophobic compound obtained by drying the supernatant after treatment.

[0123] (dynamic friction coefficient) The resin particles according to this embodiment have a dynamic friction coefficient of 0.5 or less. From the viewpoint of further improving the fluidity of the resin particles, the ratio is preferably 0.5 or less, more preferably 0.4 or less, and even more preferably 0.3 or less. From the viewpoint of improving the fluidity of the resin particles, the smaller the dynamic friction coefficient, the better, but it may be, for example, 0.01 or more, 0.05 or more, or 0.1 or more.

[0124] The dynamic friction coefficient is measured by the following procedure. The particles to be measured were measured at 0.5 mg / cm against artificial skin (Bioskin, manufactured by Bealux). 2 The sample to be measured is coated with the material as shown in the figure, and the friction tester (HEIDON) is used to measure the friction using a pseudo fingertip sensor (10 mm square piano wire sensor, manufactured by Kato Tech) as the contactor, with a load of 25 g, a speed of 1 mm / sec, and a test distance of 20 mm.

[0125] (particle size) The volume average particle size of the resin particles is preferably 3 μm or more and 100 μm or less, more preferably 5 μm or more and 70 μm or less, and even more preferably 8 μm or more and 60 μm or less.

[0126] The large diameter particle size distribution index GSDv of the biodegradable resin particles is preferably 1.5 or less, more preferably 1.3 or less, and even more preferably 1.2 or less.

[0127] The volume average particle size and the large particle size distribution index GSDp of the biodegradable resin particles are measured as follows. The particle size is measured using an LS particle size distribution analyzer "Beckman Coulter LS13 320 (manufactured by Beckman Coulter)" and the cumulative particle size distribution is plotted from the smallest diameter side on a volume basis. The particle size at 50% of the cumulative distribution is determined as the volume average particle size. On the other hand, the cumulative particle size distribution is plotted from the small diameter side on a volume basis, and the particle size at 50% of the cumulative distribution is defined as the number average particle size D50v, and the particle size at 84% of the cumulative distribution is defined as the number particle size D84v. The large diameter side number particle size distribution index GSDv is calculated using the formula GSDv = (D84v / D50v) 1 / 2 Calculated as follows.

[0128] <Method of manufacturing resin particles> The resin particles can be produced, for example, by the following method.

[0129] -First step- In the first step, base particles are prepared. The base particles can be produced by the following methods (1) to (5). (1) A kneading and crushing method in which the components are kneaded, and the resulting kneaded mixture is crushed and classified to obtain granules; (2) A dry manufacturing method in which the shape of granules obtained by the kneading and grinding method is changed by mechanical impact force or thermal energy to obtain granules. (3) A method of agglomeration and coalescence in which particle dispersions of each component are mixed, the particles in the dispersion are agglomerated, and heat-fused to obtain granules. (4) A dissolution suspension method in which an organic solvent in which each component is dissolved is suspended in an aqueous solvent to form granules containing each component. (5) A kneading and dissolving method in which each component and a binder are kneaded and extruded to form pellets, and the resulting pellets are granulated by stirring them in a solvent that dissolves only the binder.

[0130] Next, an aqueous dispersion of the obtained base particles is prepared. Before preparing the aqueous dispersion, it is preferable to wash the base particles with an acid.

[0131] Next, the aqueous dispersion, the aqueous dispersion in which the base particles are dispersed, and an aqueous solution containing the surface-treated polymer are mixed. As a result, for example, the hydroxyl groups of the resin contained in the base particles react with the amine sites of the surface-treated polymer, forming a coating layer. Then, the resin particles with the coating layer formed thereon are extracted from the mixed solution. The resin particles with the coating layer formed thereon are extracted, for example, by filtering the mixed solution. The extracted resin particles with the coating layer formed thereon are preferably washed with water. This allows the unreacted surface-treated polymer to be removed. Then, the resin particles with the coating layer formed thereon are obtained by drying the resin particles with the coating layer formed thereon.

[0132] <Application> Applications of the resin particles according to this embodiment include granular materials such as cosmetics, rolling agents, abrasives, scrubbing agents, display spacers, materials for forming beads, light diffusing particles, resin reinforcing agents, refractive index control agents, biodegradation accelerators, fertilizers, water-absorbing particles, toner particles, and anti-blocking particles.

[0133] The resin particles according to this embodiment are preferably used in cosmetics. Among these, the resin particles according to this embodiment are preferably used as a cosmetic base material. The resin particles according to this embodiment have excellent particle fluidity, and therefore when used as a cosmetic base material, the cosmetic tends to spread well on the skin when applied to the skin. Furthermore, since the resin particles according to this embodiment have a low coefficient of friction, when used as a cosmetic base material, the area on which the cosmetic is applied tends to feel good to the touch.

[0134] Specific examples of cosmetic base materials include base makeup cosmetics (e.g., makeup base, concealer, foundation, face powder, etc.); makeup cosmetics (e.g., lipstick, gloss, lip liner, blush, eye shadow, eyeliner, mascara, eyebrow, nail, nail care cosmetics, etc.); and skin care cosmetics (e.g., facial cleanser, cleanser, lotion, emulsion, serum, pack, face mask, eye and mouth care cosmetics, etc.). In particular, the resin particles according to this embodiment are preferably used as a cosmetic base material for makeup cosmetics, since cosmetic base materials for makeup cosmetics are required to have flexibility, heat resistance, and biodegradability. Here, the cosmetic base material means a component that maintains the formulation of the cosmetic composition. [Example]

[0135] Examples will be described below, but the present invention is not limited to these examples. In the following description, unless otherwise specified, all "parts" and "%" are by mass.

[0136] <Preparing each ingredient> The following materials were prepared:

[0137] [Biodegradable resin for mother particles] CAP: Cellulose acetate propionate, weight average degree of polymerization 716, acetyl group substitution degree 0.18, propionyl group substitution degree 2.49 CAB: Eastman Chemical "CAP504-0.2", cellulose acetate propionate, weight average degree of polymerization 133, acetyl substitution degree 0.04, propionyl substitution degree 2.09 PLA: Polylactic acid (weight average molecular weight 180,000) PBS: Polybutylene succinate (weight average molecular weight 200,000) PA12: Polyamide 12 DAC: Daicel Corporation "L-50", cellulose diacetate, weight average degree of polymerization 570 CAP2: Cellulose acetate phthalate

[0138] [Plasticizer for mother particles] CDNl: Cardolite "NX-2503", hydroxyethylated cardanol, molecular weight 296-320 CDN2: Cardolite "Ultra LITE 513", glycidyl ether of cardanol, molecular weight 354-361. CDN3: DIC "EPICLON 865 - Alkyl-modified" phenol novolac epoxy resin, alkyl-modified DBA: Diisobutyl adipate ATBC: Tributyl O-acetylcitrate TEH: Triethylhexanoin

[0139] [Coating layer polymer] Cosmote VH: Polyoctanium-7 manufactured by Senka Corporation Cosmote VGN: Polyoctanium-6 manufactured by Senka Corporation Lipidure-S: Polyoctanium-61 manufactured by NOF Corporation Polyacrylamide: Weight average molecular weight 400,000 Polyvinylpyrrolidone: Weight average molecular weight 40,000 Polylysine: Weight average molecular weight 5000 Epomin P-1000: Polyethyleneimine, manufactured by Nippon Shokubai Co., Ltd. LIPIDURE-PMB: NOF Polyoctanium-51 LIPIDURE-C: NOF Polyoctanium-64 K-434: Cationic polyvinyl alcohol manufactured by Mitsubishi Chemical (referred to as "cationized polyvinyl alcohol" in the table)

[0140] [Examples 1 to 31, Comparative Example 2] (Production of resin pellets) The cylinder temperature was adjusted based on the charged composition ratio shown in Table 1, and kneading was carried out using a twin-screw kneader (TEX41SS, manufactured by Toshiba Machine Co., Ltd.) to obtain a resin composition in the form of pellets (hereinafter referred to as resin pellets).

[0141] (Preparation of mother particles) 300 g of resin pellets were completely dissolved in 700 g of methyl ethyl ketone. This was added to an aqueous liquid prepared by dispersing 100 g of calcium carbonate, 4 g of carboxymethyl cellulose, and 200 g of methyl ethyl ketone in 1,100 g of pure water, and the mixture was stirred for 3 hours. 10 g of sodium hydroxide was added to the mixture, which was then heated to 80°C and stirred for 3 hours to remove the methyl ethyl ketone (hereinafter, this process will be referred to as "solvent removal" of methyl ethyl ketone). The residue was filtered and then dispersed again in pure water to obtain a base particle slurry.

[0142] On the other hand, when a resin other than DAC, CAB, and CAP was used as the resin, base particles were obtained as follows. 2000 g of resin pellets were melt-kneaded (kneader), and the kneaded material was rolled with two rolls to form a plate. The formed material was then cooled and coarsely pulverized in a pulverizer. This coarsely pulverized material was then finely pulverized in a jet mill to obtain base particles. These base particles were then dispersed in pure water to obtain a base particle slurry.

[0143] (Creation of coating layer) Using the polymers for the coating layer shown in Table 1, resin particles were obtained as follows so that the coating amounts were as shown in Table 1. After adjusting the base particle slurry to a solid content of 20%, a predetermined amount of the coating layer polymer solution, calculated as a pure content, was added to the solid content of the slurry and stirred for 1 hour at 25°C. After stirring was completed, the residue was filtered and washed with pure water, and the solid content was freeze-dried to obtain resin particles. Through the above steps, resin particles were obtained.

[0144] [Comparative Example 1] Resin particles were obtained using the same procedure as in Example 1, except that in the preparation of the base particles, after removing the solvent, the residue was filtered and the obtained base particles were freeze-dried to form resin particles (i.e., no coating layer was prepared).

[0145] <Evaluation> The number average particle diameter D50v and the dynamic friction coefficient of the obtained resin particles were measured according to the methods described above. Then, the fluidity of the resin particles was evaluated using the value of the dynamic friction coefficient according to the following evaluation criteria. (Liquidity evaluation criteria) A: Coefficient of dynamic friction is less than 0.3 B: Coefficient of dynamic friction is 0.3 or more and less than 0.4 C: Coefficient of dynamic friction is 0.4 or more and less than 0.5 D: Dynamic friction coefficient is 0.5 or more

[0146] [Table 1-1]

[0147] [Table 1-2]

[0148] From the above results, it can be seen that the resin particles of this example have high fluidity. Furthermore, it is clear that the resin particles of this example are suitable as a base material for cosmetics because they have low fluidity and a low coefficient of friction.

Claims

1. base particles containing a biodegradable resin and a plasticizer which is at least one of an ester compound and a cardanol compound; a coating layer formed on the surface of the base particle, the coating layer comprising at least one selected from the group consisting of a quaternary ammonium salt-containing polymer, polyacrylamide, polyvinylpyrrolidone, and polylysine, the coating layer being the outermost layer of the resin particle; Resin particles having the formula:

2. 2. The resin particles according to claim 1, wherein the quaternary ammonium salt-containing polymer is at least one selected from the group consisting of polyquaternium-6, polyquaternium-7, polyquaternium-51, polyquaternium-61, and polyquaternium-64.

3. 3. The resin particles according to claim 1, wherein the biodegradable resin is at least one selected from the group consisting of cellulose acylate and polyester.

4. 4. The resin particles according to claim 1, wherein the biodegradable resin is cellulose acylate.

5. 5. The resin particles according to claim 4, wherein the cellulose acylate is at least one selected from the group consisting of cellulose acetate, cellulose acetate propionate, and cellulose acetate butyrate.

6. 6. The resin particles according to claim 1, wherein the amount of the coating layer on the surface of the base particles is 0.01% by mass or more and 20% by mass or less.

7. Mother particles containing a biodegradable resin; a coating layer on the surface of the base particle, the coating layer being the outermost layer of the resin particle; and Resin particles having a dynamic friction coefficient of 0.5 or less.

8. A polymerizable composition comprising: a base particle containing a biodegradable resin and a plasticizer; a coating layer formed on the surface of the base particle, the coating layer comprising at least one selected from the group consisting of a quaternary ammonium salt-containing polymer, polyacrylamide, and polylysine, the coating layer being the outermost layer of the resin particle; Resin particles having the formula:

9. A base particle comprising a biodegradable resin which is at least one selected from the group consisting of cellulose acylate and polyester, and a plasticizer; a coating layer formed on the surface of the base particle, the coating layer comprising at least one selected from the group consisting of a quaternary ammonium salt-containing polymer, polyacrylamide, polyvinylpyrrolidone, and polylysine, the coating layer being the outermost layer of the resin particle; Resin particles having the formula:

10. The resin particles according to any one of claims 1 to 9, which are used for cosmetics.

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