Hydrophilicity-imparting agent, and resin composition containing the same

Abstract

To provide a hydrophilicity-imparting agent capable of imparting hydrophilicity and low friction property to a resin.SOLUTION: A hydrophilicity-imparting agent is an amide of a 16-24C aliphatic amine (a) and a 16-24C fatty acid (b), where at least one of the aliphatic amine (a) and the fatty acid (b) is a cis-type amide including a cis-type unsaturated structure, and including no trans-type unsaturated structure in the structure, and an amide of a 16-24C aliphatic amine (c) and a 16-24C fatty acid (d) at least one of the aliphatic amine (c) and the fatty acid (d) includes a trans-type amide including a trans-type unsaturated structure, and including no cis-type unsaturated structure in the structure, and a mass ratio of the cis-type amide and the trans-type amide is 99.9:0.1 to 50:50.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a hydrophilicity-imparting agent and a resin composition containing the same. [Background technology]

[0002] Thermoplastic resins and other resins can have properties such as moldability, elasticity, and strength controlled by structural design, and are used in a wide range of fields, including everyday items, construction and civil engineering materials, electrical appliance parts, and automobile parts. Surface treatments and the addition of modifiers can impart functionality such as hydrophilicity and gas barrier properties, so it is common to modify resins to meet the required properties for each application.

[0003] Hydrophilicity is one of the functions that can be imparted to resins. By imparting hydrophilicity to resins, it is expected that anti-fogging properties and antistatic effects can be imparted. Patent Document 1 discloses the use of a fatty acid alkanolamide surfactant as a hydrophilizing agent for imparting hydrophilicity to polyethylene resins. Patent Document 2 discloses a thermoplastic resin composition that uses an acrylic-modified glycol polymer as a hydrophilizing agent and has excellent durability of hydrophilic effect.

[0004] Another function that can be imparted to resins is the slipperiness (low friction) of the resin. By reducing the frictional force of the resin, it is expected that the sliding properties and releasability can be improved. For example, such properties are often required in fields such as precision machinery and food packaging. In response to such demands, Patent Document 3 describes how the low friction properties of wrap films can be improved by adding porous inorganic materials. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2013-10906 A [Patent Document 2] JP 2011-32467 A [Patent Document 3] JP 2021-38376 A Summary of the Invention [Problem to be solved by the invention]

[0006] When storing food immediately after cooking, various resins are used to package the food. In this case, hydrophilicity may be imparted to prevent electrostatic charge in order to prevent dust adsorption, etc. Furthermore, stability over time is required to maintain functionality even after storage in a high-temperature, high-humidity warehouse. Low friction is also required to prevent damage to food during packaging. In order to impart such properties, it is assumed that the additives described in the above-mentioned patent documents are added. However, the greater the amount of additives for hydrophilization or additives for imparting low friction, the greater the risk of a decrease in the strength and durability of the packaging material. Therefore, it is preferable that the amount and type of additives are small, and it is desirable that a small amount of additives can be highly effective or that one additive can impart multiple properties. However, the reality is that it is still difficult to realize a hydrophilicity imparting agent that can impart both hydrophilicity and low friction properties and has excellent stability over time, and a resin composition using the same.

[0007] In view of the problems in the prior art described above, the present application has been made. An object of the present invention is to provide a hydrophilicity-imparting agent capable of imparting hydrophilicity and low friction to a resin, and a resin composition having excellent stability over time of hydrophilicity and low friction. [Means for solving the problem]

[0008] As a result of intensive research, the present inventors have found that the above-mentioned problems can be solved by a hydrophilicity-imparting agent containing a cis-amide of a specific structure and a trans-amide of a specific structure in a specific quantitative ratio, and a resin composition containing the same in a specific quantitative ratio relative to a resin.

[0009] The gist of the present invention is as follows. (1) A hydrophilicity-imparting agent comprising an amide of an aliphatic amine a having 16 to 24 carbon atoms and a fatty acid b having 16 to 24 carbon atoms, wherein at least one of the aliphatic amine a and the fatty acid b contains a cis-type unsaturated structure and does not contain a trans-type unsaturated structure in its structure, and an amide of an aliphatic amine c having 16 to 24 carbon atoms and a fatty acid d having 16 to 24 carbon atoms, wherein at least one of the aliphatic amine c and the fatty acid d contains a trans-type unsaturated structure and does not contain a cis-type unsaturated structure in its structure, and the mass ratio of the cis-type amide to the trans-type amide is 99.9:0.1 to 50:50. (2) A resin composition comprising 100 parts by mass of a resin and 0.5 to 30 parts by mass of the hydrophilicity imparting agent described in (1). Effect of the Invention

[0010] According to the present invention, there are provided a hydrophilicity-imparting agent capable of imparting hydrophilicity and low friction to a resin, and a resin composition which is excellent in the stability of hydrophilicity and low friction over time. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] Hereinafter, the hydrophilicity imparting agent and the resin composition according to the embodiment of the present invention will be described. In this specification, the numerical range specified using the symbol "~" includes the numerical values ​​at both ends (upper and lower limits) of "~". For example, "2~10" means 2 or more and 10 or less.

[0012] [Hydrophilicity-imparting agent] The hydrophilicity-imparting agent according to one embodiment of the present invention includes (A) an amide of an aliphatic amine a having 16 to 24 carbon atoms and a fatty acid b having 16 to 24 carbon atoms, in which at least one of the aliphatic amine a and the fatty acid b contains a cis-type unsaturated structure and does not contain a trans-type unsaturated structure in the structure (hereinafter, sometimes referred to as "cis-type amide (A)"); and (B) an amide of an aliphatic amine c having 16 to 24 carbon atoms and a fatty acid d having 16 to 24 carbon atoms, in which at least one of the aliphatic amine c and the fatty acid d contains a trans-type unsaturated structure and does not contain a cis-type unsaturated structure in the structure (hereinafter, sometimes referred to as "trans-type amide (B)"). The mass ratio (A:B) of the cis-type amide (A) and the trans-type amide (B) is 99.9:0.1 to 50:50.

[0013] The cis-amide (A) is a compound obtained by dehydration polycondensation of a specific cis-unsaturated aliphatic amine and a specific unsaturated non-trans fatty acid, a specific unsaturated non-trans fatty amine and a specific cis-unsaturated fatty acid, or a specific cis-unsaturated aliphatic amine and a specific cis-unsaturated fatty acid. The hydrophilicity-imparting agent may contain only one type of cis-amide (A), or may contain two or more types. When the hydrophilicity-imparting agent contains two or more types of cis-amide (A), it is preferable that the structures derived from the cis-unsaturated aliphatic amine in each cis-amide (A) are the same from the viewpoint of improving low friction.

[0014] Here, the aliphatic amine a used in the cis-amide (A) may have an aliphatic chain having 16 to 24 carbon atoms and one amino group bonded thereto. The aliphatic amine a may be a cis-unsaturated aliphatic amine, an unsaturated aliphatic amine not having a cis-trans structure (i.e., having an unsaturated structure at a terminal), or a saturated aliphatic amine.

[0015] In the present specification, the term "cis-unsaturated aliphatic amine" refers to a primary amine having a cis-unsaturated aliphatic group and one amino group bonded to the terminal of the unsaturated aliphatic group. The number of carbon atoms constituting the cis-unsaturated aliphatic group may be 16 to 24, but from the viewpoint of further improving hydrophilicity and low friction, it is preferably 16 to 22, and more preferably 16 to 20. The cis-unsaturated aliphatic group may be linear or branched, but is preferably linear. In the case of a branched chain, the number of carbon atoms constituting the branched chain (the chain bonded to the main chain) is preferably 1 to 4.

[0016] The number of unsaturated carbon-carbon bonds in the cis-unsaturated aliphatic group may be 1 or more, and may be 2 or more. When the cis-unsaturated aliphatic group has two or more unsaturated carbon-carbon bonds, all of them (except for the terminal unsaturated carbon-carbon structure) are cis structures.

[0017] Examples of the cis-unsaturated aliphatic amines include palmitoleylamine (carbon number: 16), oleylamine (carbon number: 18), linoleamine (carbon number: 18), linolenicamine (carbon number: 18), eicoseneamine (carbon number: 20), and erucamine (carbon number: 22).

[0018] On the other hand, unsaturated aliphatic amines not having a cis-trans structure and saturated aliphatic amines are also preferably primary amines. The number of carbon atoms constituting these aliphatic groups may be 16 to 24, but from the viewpoint of further improving hydrophilicity and low friction, it is preferably 16 to 22, and more preferably 16 to 20. These aliphatic chains may be linear or branched, but are preferably linear. In addition, in the case of branched chains, the number of carbon atoms constituting the branched chain (chain bonded to the main chain) is preferably 1 to 4.

[0019] Examples of unsaturated aliphatic amines that do not have a cis-trans structure and saturated aliphatic amines include cetylamine (carbon number 16), heptadecylamine (carbon number 17), stearylamine (carbon number 18), nonadecylamine (carbon number 19), arachidylamine (carbon number 20), henicosylamine (carbon number 21), behenylamine (carbon number 22), tricosylamine (carbon number 23), and tetracosylamine (carbon number 24).

[0020] On the other hand, the fatty acid b used in the cis-amide (A) may have an aliphatic chain having 16 to 24 carbon atoms and one carboxyl group bonded thereto. The fatty acid b may be a cis-unsaturated fatty acid, an unsaturated fatty acid that does not have a cis-trans structure (i.e., has an unsaturated structure at the terminal), or a saturated fatty acid.

[0021] In the present specification, the term "cis-unsaturated fatty acid" refers to a primary fatty acid having a cis-unsaturated aliphatic group and one carboxyl group bonded to the terminal of the unsaturated aliphatic group. The number of carbon atoms constituting the cis-unsaturated aliphatic group may be 16 to 24, but from the viewpoint of further improving hydrophilicity and low friction, it is preferably 16 to 22, and more preferably 16 to 20. The cis-unsaturated aliphatic group may be linear or branched, but is preferably linear. In the case of a branched chain, the number of carbon atoms constituting the branched chain (the chain bonded to the main chain) is preferably 1 to 4.

[0022] The number of unsaturated carbon-carbon bonds in the cis-unsaturated aliphatic group may be 1 or more, and may be 2 or more. When the cis-unsaturated aliphatic group has two or more unsaturated carbon-carbon bonds, all of them (except for the terminal unsaturated carbon-carbon structure) are cis structures.

[0023] Examples of the cis-unsaturated fatty acids include palmitoleic acid (16 carbon atoms), oleic acid (18 carbon atoms), linoleic acid (18 carbon atoms), linolenic acid (18 carbon atoms), eicosenoic acid (20 carbon atoms), eicosadienoic acid (20 carbon atoms), mead acid (20 carbon atoms), dihomo-γ-linolenic acid (20 carbon atoms), eicosatrienoic acid (20 carbon atoms), and eicosatetraenoic acid. These include arachidonic acid (20 carbons), eicosapentaenoic acid (20 carbons), erucic acid (22 carbons), docosadienoic acid (22 carbons), adrenic acid (22 carbons), isomeric acid (22 carbons), docosahexaenoic acid (22 carbons), nervonic acid (24 carbons), tetracosapentaenoic acid (24 carbons), and herring acid (24 carbons).

[0024] On the other hand, unsaturated fatty acids not having a cis-trans structure and saturated fatty acids are preferably primary fatty acids. The number of carbon atoms constituting these aliphatic groups may be 16 to 24, but from the viewpoint of further improving hydrophilicity and low friction, it is preferably 16 to 22, and more preferably 16 to 20. These aliphatic chains may be linear or branched, but are preferably linear. In addition, in the case of branched chains, the number of carbon atoms constituting the branched chain (chain bonded to the main chain) is preferably 1 to 4.

[0025] Examples of unsaturated fatty acids that do not have a cis-trans structure and saturated fatty acids include palmitic acid (16 carbon atoms), heptadecanoic acid (17 carbon atoms), stearic acid (18 carbon atoms), nonadecanoic acid (19 carbon atoms), arachidic acid (20 carbon atoms), heneicosylic acid (21 carbon atoms), behenic acid (22 carbon atoms), tricosylic acid (23 carbon atoms), and lignoceric acid (24 carbon atoms).

[0026] The cis-type amide (A) may be a combination of any of the above aliphatic amines a and any of the fatty acids b. However, one of them contains a cis-type unsaturated structure. The carbon numbers of the aliphatic amine a and the fatty acid b are preferably close to each other, and the difference in the carbon numbers is preferably 6 or less, and more preferably 4 or less. Examples of the cis-type amide (A) include N-palmitoleyl palmitamide, N-palmitoleyl stearylamide, N-palmitoleyl arachidinamide, N-palmitoleyl behenamide, N-palmitoleyl lignocerinamide, N-palmitoleyl oleylamide, N-palmitoleyl palmitoleamide, N-palmitoleyl linoleamide, N-palmitoleyl linoleneamide, N-oleyl palmitamide, N-oleyl stearylamide, N-oleyl arachidinamide, and the like. N-oleyl behenamide, N-oleyl lignocerinamide, N-oleyl oleylamide, N-oleyl palmitoleamide, N-oleyl linoleamide, N-oleyl linoleneamide, N-linole palmitamide, N-linole stearylamide, N-linole arachidinamide, N-linole behenamide, N-linole lignocerinamide, N-linole oleylamide, N-linole palmitoleamide, N-linole linoleamide, N-linole Linolenic amide, N-linolenic palmitamide, N-linolenic stearyl amide, N-linolenic arachidin amide, N-linolenic behenamide, N-linolenic lignocerin amide, N-linolenic oleyl amide, N-linolenic palmitoleic amide, N-linolenic linolenic amide, N-linolenic linolenic amide, N-eicosene palmitamide, N-eicosene stearyl amide, N-eicosene arachidin amide, N-eicosene behenamide, N-eicosene lignocerin amide , N-eicosene oleylamide, N-eicosene palmitoleylamide, N-eicosene linoleylamide, N-eicosene linolene amide, N-erucyl palmitamide, N-erucyl stearylamide, N-erucyl arachidinamide, N-erucyl behenamide, N-erucyl lignocerinamide, N-erucyl oleylamide, N-erucyl palmitoleylamide, N-erucyl linoleylamide, N-erucyl linolene amide, N-erucyl linolene amide, and N-stearyl erucamide.

[0027] Among the above, preferred are N-palmitoleyl palmitamide, N-palmitoleyl stearylamide, N-palmitoleyl arachidinamide, N-palmitoleyl behenamide, N-palmitoleyl lignocerinamide, N-palmitoleyl oleylamide, N-oleyl palmitamide, N-oleyl stearylamide, N-oleyl arachidinamide, N-oleyl behenamide, N-oleyl lignocerinamide, N-oleyl oleylamide, N-oleyl palmitoleylamide, N-oleyl linoleamide, N-oleyl linoleneamide, and N-stearyl erucamide, and more preferred are N-oleyl palmitamide, N-oleyl stearylamide, N-oleyl oleylamide, and N-stearyl erucamide.

[0028] On the other hand, the trans-amide (B) is a compound obtained by dehydration polycondensation of a specific trans-unsaturated aliphatic amine and a specific unsaturated non-cis fatty acid, a specific unsaturated non-cis fatty amine and a specific trans-unsaturated fatty acid, or a specific trans-unsaturated aliphatic amine and a specific trans-unsaturated fatty acid. The hydrophilicity-imparting agent may contain only one type of trans-amide (B), or may contain two or more types. In addition, when the hydrophilicity-imparting agent contains two or more types of trans-amide (B), it is preferable that the structures derived from the trans-unsaturated aliphatic amine in each trans-amide (B) are the same from the viewpoint of improving low friction.

[0029] Here, the aliphatic amine c used in the trans amide (B) may have an aliphatic chain having 16 to 24 carbon atoms and one amino group bonded thereto. The aliphatic amine c may be a trans unsaturated aliphatic amine, an unsaturated aliphatic amine not having a cis-trans structure (i.e., having an unsaturated structure at a terminal), or a saturated aliphatic amine.

[0030] In the present specification, the term "trans-unsaturated aliphatic amine" refers to a primary amine having a trans-unsaturated aliphatic group and one amino group bonded to the end of the unsaturated aliphatic group. The number of carbon atoms constituting the trans-unsaturated aliphatic group may be 16 to 24, but from the viewpoint of further improving hydrophilicity and low friction, it is preferably 16 to 22, and more preferably 16 to 20. The trans-unsaturated aliphatic group may be linear or branched, but is preferably linear. In the case of a branched chain, the number of carbon atoms constituting the branched chain (the chain bonded to the main chain) is preferably 1 to 4.

[0031] The number of unsaturated carbon-carbon bonds in the trans-unsaturated aliphatic group may be 1 or more, and may be 2 or more. When the trans-unsaturated aliphatic group has 2 or more unsaturated carbon-carbon bonds, all of them are trans (except for the terminal unsaturated carbon-carbon structure).

[0032] Examples of the trans-unsaturated aliphatic amines include palmitoelaidylamine (carbon number: 16), elaidylamine (carbon number: 18), and elaidyleicosylamine (carbon number: 20).

[0033] On the other hand, unsaturated aliphatic amines not having a cis-trans structure and saturated aliphatic amines are also preferably primary amines, and these are similar to the unsaturated aliphatic amines not having a cis-trans structure and saturated aliphatic amines described above in relation to the aliphatic amine a.

[0034] On the other hand, the fatty acid d used in the trans amide (B) may have an aliphatic chain having 16 to 24 carbon atoms and one carboxyl group bonded thereto. The fatty acid d may be a trans unsaturated fatty acid, an unsaturated fatty acid that does not have a cis-trans structure (i.e., has an unsaturated structure at the terminal), or a saturated fatty acid.

[0035] Here, the term "trans-unsaturated fatty acid" in this specification refers to a primary fatty acid having a trans-unsaturated aliphatic group and one carboxyl group bonded to the end of the unsaturated aliphatic group. The number of carbon atoms constituting the trans-unsaturated aliphatic group may be 16 to 24, but from the viewpoint of further improving hydrophilicity and low friction, it is preferably 16 to 22, and more preferably 16 to 20. The trans-unsaturated aliphatic group may be linear or branched, but is preferably linear. In the case of a branched chain, the number of carbon atoms constituting the branched chain (the chain bonded to the main chain) is preferably 1 to 4.

[0036] The number of unsaturated carbon-carbon bonds in the trans-unsaturated aliphatic group may be 1 or more, and may be 2 or more. When the trans-unsaturated aliphatic group has 2 or more unsaturated carbon-carbon bonds, all of them are trans (except for the terminal unsaturated carbon-carbon structure).

[0037] Examples of the trans-unsaturated fatty acids include palmitoleladic acid (carbon number: 16), elaidic acid (carbon number: 18), vaccenic acid (carbon number: 18), trans-11-eicosenoic acid (carbon number: 20), and brassidic acid (carbon number: 22).

[0038] On the other hand, it is preferable that unsaturated fatty acids that do not have a cis-trans structure and saturated fatty acids are also primary fatty acids, and these are similar to the unsaturated fatty acids that do not have a cis-trans structure and saturated fatty acids that are described above in fatty acid b.

[0039] The trans-amide (B) may be combined with any of the above aliphatic amines c or fatty acids d. However, one of them contains a trans-unsaturated structure. The carbon numbers of the aliphatic amine and the fatty acid are preferably close to each other, and the difference in carbon numbers is preferably 4 or less, more preferably 2 or less. Examples of the trans-amide (B) include N-palmitoelaidyl palmitamide, N-palmitoelaidyl stearylamide, N-palmitoelaidyl arachidinamide, N-palmitoelaidyl behenamide, N-palmitoelaidyl lignocerinamide, N-palmitoelaidyl oleylamide, N-palmitoelaidyl palmitoleamide, N-palmitoelaidyl linoleamide, N-palmitoelaidyl linolenic amide, N-elaidy palmitamide, N-elaidy stearylamide, N-elaidy arachidinamide, N-elaidy behenamide, N-elaidy lignocerinamide, N-elaidy oleylamide, N-elaidy palmitoleamide, N-elaidy linoleamide, N-elaidy linolenic amide, N-elaidy eicosene palmitamide. amide, N-elaidyl eicosene stearylamide, N-elaidyl eicosene arachidinamide, N-elaidyl eicosene behenamide, N-elaidyl eicosene lignocerinamide, N-elaidyl eicosene oleylamide, N-elaidyl eicosene palmitoleamide, N-elaidyl eicosene linoleamide, N-elaidyl eicosene linoleneamide, N-elaidyl erucyl palmitamide, N-elaidyl erucyl stearylamide, N-elaidyl erucyl arachidinamide, N-elaidyl erucyl behenamide, N-elaidyl erucyl lignocerinamide, N-elaidyl erucyl oleylamide, N-elaidyl erucyl palmitoleamide, N-elaidyl erucyl linoleamide, N-elaidyl erucyl linoleneamide, and the like.

[0040] Among the above, N-palmitoelaidyl palmitamide, N-palmitoelaidyl stearylamide, N-palmitoelaidyl arachidinamide, N-palmitoelaidyl behenamide, N-palmitoelaidyl lignocerinamide, N-elaidyll palmitamide, N-elaidyll stearylamide, N-elaidyll arachidinamide, N-elaidyll behenamide, N-elaidyll lignocerinamide, N-elaidyll oleylamide, and N-elaidyll palmitoleamide are preferred, and N-palmitoelaidyl palmitamide, N-palmitoelaidyl stearylamide, N-elaidyll palmitamide, and N-elaidyll stearylamide are more preferred.

[0041] The combination of the cis-amide (A) and the trans-amide (B) is not particularly limited, but it is preferable that the composition of the unsaturated aliphatic group in the cis-amide (A) is the same as that of the unsaturated aliphatic group in the trans-amide (B). This makes it possible to maintain low friction for a longer period of time when the hydrophilicity-imparting agent is combined with a resin.

[0042] The mass ratio (A:B) of the cis-amide (A) and the trans-amide (B) is 99.9:0.1 to 50:50, preferably 99.9:0.1 to 75:25, more preferably 99.9:0.1 to 90:10, and even more preferably 99.9:0.1 to 95:5. When the mass ratio is within the above range, hydrophilicity and low friction are easily obtained when the hydrophilicity-imparting agent is mixed with the resin. In addition, hydrophilicity and low friction are easily stably exhibited over a long period of time.

[0043] The hydrophilicity-imparting agent may contain components other than the cis-amide (A) and the trans-amide (B) within a range that does not impair the object and effect of the present invention. However, the total amount of the cis-amide (A) and the trans-amide (B) relative to 100 parts by mass of the hydrophilicity-imparting agent is preferably 30 parts by mass or more, more preferably 50 parts by mass or more, and even more preferably 100 parts by mass.

[0044] The method for producing the hydrophilicity-imparting agent is not particularly limited. For example, the above-mentioned aliphatic amine a and fatty acid b, and aliphatic amine c and fatty acid d may be respectively subjected to an amidation reaction at 70 to 250°C to prepare cis-amide (A) and trans-amide (B), and these may be melt-mixed at the above ratio. On the other hand, the above amidation reaction may be carried out by mixing a common fatty acid (fatty acid b or fatty acid d) which is a raw material for cis-amide (A) and trans-amide (B), with a cis-unsaturated aliphatic amine (fatty amine a) and a trans-unsaturated aliphatic amine (fatty amine c). In this case, the cis-amide (A) and trans-amide (B) are within a desired range by adjusting the ratio of the cis-unsaturated aliphatic amine and the trans-unsaturated aliphatic amine to be mixed. Similarly, the above amidation reaction may be carried out by mixing a common aliphatic amine (fatty acid a or c) with a cis-unsaturated fatty acid (fatty acid b) and a trans-unsaturated fatty acid (fatty acid d). In this case, the ratio of cis- and trans-fatty acids to be mixed can be adjusted so that the cis-amide (A) and trans-amide (B) fall within the desired range.

[0045] [Resin composition] The resin composition according to one embodiment of the present invention contains 100 parts by mass of a resin and 0.5 to 30 parts by mass of the hydrophilicity imparting agent. The resin composition may contain other components as necessary in addition to the resin and the hydrophilicity imparting agent.

[0046] The resin is not particularly limited as long as it is a resin that can be used for food packaging purposes, and examples of the resin include general-purpose plastics.

[0047] Examples of general-purpose plastics include thermoplastic elastomers, ethylene copolymers (e.g., ethylene-methacrylic copolymers and ethylene-acrylic copolymers), ionomer resins, etc. Examples of thermoplastic elastomers include polyethylene-based elastomers, polypropylene-based elastomers, polyvinyl chloride-based elastomers, polyvinylidene chloride-based elastomers, polystyrene-based elastomers, polyvinyl acetate-based elastomers, polyurethane-based elastomers, acrylonitrile butadiene styrene-based elastomers, acrylic-based elastomers, methacrylic-based elastomers, and olefin / alkene-based elastomers.

[0048] Among these resins, olefin / alkene-based elastomers, ethylene copolymers, and ionomer resins are preferred, and olefin / alkene-based elastomers are particularly preferred. The above resins can be used alone or in combination of two or more kinds.

[0049] The amount of the hydrophilicity imparting agent in the resin composition may be 0.5 to 30 parts by mass, preferably 1 to 20 parts by mass, and more preferably 2 to 10 parts by mass, when the mass of the resin is 100 parts by mass. When the content is within the above range, sufficient hydrophilicity and low friction are obtained, and further, stability over time is obtained.

[0050] The resin composition may also contain various components that are generally added to adjust the physical properties. Examples of such components include plasticizers, crosslinking agents, softeners, tackifiers, antistatic agents, fillers, antioxidants, silane coupling agents, zinc oxide, vulcanization accelerators, vulcanizing agents, stearic acid, workability improvers, resins, waxes, oils, and solvents, and these may be appropriately selected and contained within a range that does not impair the object of the present invention.

[0051] The resin composition can be produced by blending the above-mentioned components and mixing them homogeneously by a known method such as stirring or kneading depending on the properties of the blend.

[0052] In addition, when the hydrophilicity-imparting agent is present in the thermosetting elastomer, it is preferable to mix the rubber composition containing the thermosetting elastomer before vulcanization with the hydrophilicity-imparting agent and then vulcanize the mixture.

[0053] The above resin composition can be molded by a known method according to the type of resin to form a molded body. Examples of the method for producing a molded body include the T-die method in which resin is extruded from a T-shaped mold to mold, and the calendar molding method in which a heated resin composition is passed between rolls to mold to a predetermined thickness. The heat resistance, hydrophilicity, and low friction stability of the molded body over time can be evaluated, for example, by the evaluation method of the examples described later, and the hydrophilicity imparting agent and the resin composition can be evaluated.

[0054] In addition, such molded articles can be used for various purposes, including building and civil engineering materials such as daily necessities and sealants, electrical appliance parts, automobile parts, and packaging for food, etc. In particular, they are preferably used for sealants, electrical appliance parts, and food packaging. EXAMPLES

[0055] Hereinafter, the embodiments of the present invention will be described in detail with reference to examples and comparative examples.

[0056] 1. Synthesis of amides (Synthesis Example 1) Synthesis of N-oleyl palmitamide (cis-form amide (A)) Palmitic acid (200g, 0.78mol) was charged into a 500mL five-neck flask equipped with a thermometer, a nitrogen inlet tube, and an air-cooled tube, and oleylamine (209g, 0.78mol) was added dropwise using a dropping funnel. The reaction was then carried out at 220℃, and was terminated when the decrease in acid value per hour reached 0.5mgKOH / g or less, yielding 363g (0.72mol) of N-oleylpalmitamide.

[0057] (Synthesis Example 2) Synthesis of N-elaidyl palmitamide (trans amide (B)) Palmitic acid (200g, 0.78mol) was charged into a 500mL five-neck flask equipped with a thermometer, a nitrogen inlet tube, and an air cooling tube, and elaidylamine (209g, 0.78mol) was gradually added using a dropping funnel. The reaction was then carried out at 220℃, and was terminated when the decrease in acid value per hour reached 0.5mgKOH / g or less, yielding 363g (0.72mol) of N-elaidylpalmitamide.

[0058] (Synthesis Example 3) Synthesis of N-palmitoelaidylstearylamide (trans amide (B)) Stearic acid (220g, 0.78mol) was charged into a 500mL five-neck flask equipped with a thermometer, a nitrogen inlet tube, and an air cooling tube, and palmitoelaidylamine (187g, 0.78mol) was added dropwise using a dropping funnel. The reaction was then carried out at 220℃, and was terminated when the decrease in acid value per hour reached 0.5mgKOH / g or less, yielding 355g (0.70mol) of N-palmitoelaidylstearylamide.

[0059] (Synthesis Example 4) Synthesis of N-oleyl myristylamide (cis-form amide (A)) Myristic acid (178g, 0.78mol) was charged into a 500mL five-neck flask equipped with a thermometer, a nitrogen inlet tube, and an air cooling tube, and oleylamine (208g, 0.78mol) was added dropwise using a dropping funnel. The reaction was then carried out at 220℃, and was terminated when the decrease in acid value per hour reached 0.5mgKOH / g or less, yielding 372g (0.78mol) of N-oleylmyristylamide.

[0060] (Synthesis Example 5) Synthesis of N-stearyl erucamide (cis-amide (A)) Erucic acid (264g, 0.78mol) was charged into a 300mL five-neck flask equipped with a thermometer, a nitrogen inlet tube, and an air cooling tube, and stearylamine (209g, 0.78mol) was added dropwise using a dropping funnel. The reaction was then carried out at 220℃, and was terminated when the decrease in acid value per hour reached 0.5mgKOH / g or less, yielding 419g (0.71mol) of N-stearyl palmitamide.

[0061] (Synthesis Example 6) Synthesis of N-oleyl oleylamide (cis-amide (A)) Oleic acid (220g, 0.78mol) was charged into a 300mL five-neck flask equipped with a thermometer, a nitrogen inlet tube, and an air cooling tube, and oleylamine (208g, 0.78mol) was added dropwise using a dropping funnel. The reaction was then carried out at 220°C, and was terminated when the decrease in acid value per hour reached 0.5mgKOH / g or less, yielding 386g (0.72mol) of N-oleyl oleylamide.

[0062] (Synthesis Example 7) Synthesis of N-stearyl palmitamide (saturated amide) Palmitic acid (220g, 0.78mol) was charged into a 300mL five-neck flask equipped with a thermometer, a nitrogen inlet tube, and an air-cooled tube, and stearylamine (209g, 0.78mol) was added dropwise using a dropping funnel. The reaction was then carried out at 220℃, and was terminated when the decrease in acid value per hour reached 0.5mgKOH / g or less, yielding 344g (0.72mol) of N-stearyl palmitamide.

[0063] 2. Preparation of composition (hydrophilicity imparting agent) Each hydrophilicity-imparting agent was prepared by the following method.

[0064] (Combination example 1) 199.6 g of N-oleyl palmitamide prepared in Synthesis Example 1 and 0.4 g of N-elaidyl palmitamide prepared in Synthesis Example 2 were charged. The mixture was heated and melted at 120° C. while stirring with a magnetic stirrer, and heated and stirred for 1 hour to obtain Composition 1, which is a mixture of N-oleyl palmitamide and N-elaidyl palmitamide (N-oleyl palmitamide: N-elaidyl palmitamide = 99.8: 0.2).

[0065] (Combination example 2) Except for using 190.0 g of N-oleyl palmitamide prepared in Synthesis Example 1 and 10.0 g of N-elaidyl palmitamide prepared in Synthesis Example 2, the same procedure as in Formulation Example 1 was repeated to obtain Composition 2, which is a mixture of N-oleyl palmitamide and N-elaidyl palmitamide (N-oleyl palmitamide: N-elaidyl palmitamide = 95:5).

[0066] (Combination example 3) Except for using 180.0 g of N-oleyl palmitamide prepared in Synthesis Example 1 and 20.0 g of N-elaidyl palmitamide prepared in Synthesis Example 2, the same procedure as in Formulation Example 1 was repeated to obtain Composition 3, which is a mixture of N-oleyl palmitamide and N-elaidyl palmitamide (N-oleyl palmitamide: N-elaidyl palmitamide = 90:10).

[0067] (Combination example 4) Except for using 150.0 g of N-oleyl palmitamide prepared in Synthesis Example 1 and 50.0 g of N-elaidyl palmitamide prepared in Synthesis Example 2, the same procedure as in Formulation Example 1 was repeated to obtain Composition 4, which is a mixture of N-oleyl palmitamide and N-elaidyl palmitamide (N-oleyl palmitamide: N-elaidyl palmitamide = 75:25).

[0068] (Combination example 5) Except for using 180.0 g of N-oleyl palmitamide prepared in Synthesis Example 1 and 20.0 g of N-palmitoelaidylstearylamide prepared in Synthesis Example 3, the same procedure as in Formulation Example 1 was repeated to obtain Composition 5, which is a mixture of N-oleyl palmitamide and N-elaidyl palmitamide (N-oleyl palmitamide: N-palmitoelaidylstearylamide = 90:10).

[0069] (Combination example 6) Except for using 100.0 g of N-oleyl palmitamide prepared in Synthesis Example 1 and 100.0 g of N-elaidyl palmitamide prepared in Synthesis Example 2, the same procedure as in Formulation Example 1 was repeated to obtain Composition 6, which is a mixture of N-oleyl palmitamide and N-elaidyl palmitamide (N-oleyl palmitamide: N-elaidyl palmitamide = 50:50).

[0070] (Combination example 7) The same procedure as in Formulation Example 1 was repeated except that 180.0 g of N-stearyl erucamide prepared in Synthesis Example 5 and 20.0 g of N-elaidyl palmitamide prepared in Synthesis Example 2 were used, to obtain Composition 7, which is a mixture of N-oleyl palmitamide and N-elaidyl palmitamide (N-stearyl erucamide:N-elaidyl palmitamide=90:10).

[0071] (Combination example 8) Except for using 150.0 g of N-oleyl oleylamide prepared in Synthesis Example 6 and 50.0 g of N-elaidyl palmitamide prepared in Synthesis Example 2, the same procedure as in Formulation Example 1 was performed to obtain Composition 8, which is a mixture of N-oleyl oleylamide and N-elaidyl palmitamide (N-oleyl oleylamide: N-elaidyl palmitamide = 75:25).

[0072] (Combination example 9) Except for using 80.0 g of N-oleyl palmitamide prepared in Synthesis Example 1 and 120.0 g of N-elaidyl palmitamide prepared in Synthesis Example 2, the same procedure as in Formulation Example 1 was repeated to obtain Composition 9, which is a mixture of N-oleyl palmitamide and N-elaidyl palmitamide (N-oleyl palmitamide: N-elaidyl palmitamide = 40:60).

[0073] (Combination example 10) Composition 10 was prepared by using only the N-oleyl palmitamide prepared in Synthesis Example 1.

[0074] (Combination example 11) Except for using 150.0 g of N-oleyl myristylamide prepared in Synthesis Example 4 and 50.0 g of N-elaidyl palmitamide prepared in Synthesis Example 2, the same procedure as in Formulation Example 1 was repeated to obtain Composition 11, which is a mixture of N-oleyl myristylamide and N-elaidyl palmitamide (N-oleyl myristylamide:N-elaidyl palmitamide = 75:25).

[0075] (Combination example 12) Except for using 190.0 g of N-oleyl palmitamide prepared in Synthesis Example 1 and 10.0 g of N-stearyl palmitamide prepared in Synthesis Example 7, the same procedure as in Blending Example 1 was carried out to obtain Composition 12, which is a mixture of N-oleyl palmitamide and N-stearyl palmitamide (N-oleyl palmitamide: N-stearyl palmitamide = 95:5).

[0076] [Table 1]

[0077] 3. Preparation of Resin Composition A resin composition was prepared in the following manner.

[0078] Example 1 0.05 g of composition 1 (hydrophilicity imparting agent for resin) was weighed out and mixed with 0.95 g of olefin / alkene-based elastomer (product name: Ultrathene (registered trademark) 685, manufactured by Tosoh Corporation, ethylene vinyl acetate copolymer) and 49 g of solvent (toluene) to prepare a resin composition. The obtained resin composition was subjected to the evaluation test described below.

[0079] (Examples 2 to 8, Comparative Examples 1 to 4) Resin compositions were prepared in the same manner as in Example 1, except that compositions 2 to 12 as shown in Table 2 were used, and the obtained resin compositions were subjected to the evaluation tests described below.

[0080] 4. Evaluation The following evaluations were carried out on the resin compositions of Examples 1 to 8 and Comparative Examples 1 to 4, each containing the above-mentioned hydrophilicity-imparting agent. The results are shown in Table 2.

[0081] (1) Hydrophilicity Evaluation Each resin composition was applied onto a glass substrate using a bar coater and dried on a hot plate at 100°C for 30 minutes, thereby forming a resin film having a thickness of 1 μm. The contact angle of the obtained resin film was measured by the tangent method according to JIS R3257. The hydrophilicity of the resin film was evaluated according to the following indices. The evaluation criteria are as follows. ◎: Less than 50° ○: 50° to less than 70° △: 70° or more and less than 85° ×: 85° or more

[0082] (2) Evaluation of the friction coefficient The resin compositions of Examples 1 to 8 and Comparative Examples 1 to 4 were each applied onto a glass substrate using a bar coater and dried on a hot plate at 100°C for 30 minutes, thereby forming a resin film with a thickness of 1 mm. The friction coefficient of the resulting resin film was measured using a Bowden tester under the following conditions: contact (semi-cylindrical stainless steel, 1 cm), load: 100 g, speed: 2.5 mm / s, measurement distance: 10 mm, and number of tests: 10, and the average value was calculated. The evaluation criteria were as follows. ◎: Less than 0.200 ○: 0.200 or more and less than 0.250 △: 0.250 or more and less than 0.300 ×:0.300 or more

[0083] (3) Evaluation of stability over time The glass substrates on which the resin films were formed as prepared in the evaluations (1) and (2) above were stored at 80°C and 70% humidity for one week, and an accelerated test was performed. The resin films were then washed with water and dried at room temperature for one day. The contact angle and friction coefficient of the dried resin films were measured in the same manner as in the evaluations (1) and (2) above. The rate of change was calculated from the following formula, based on the values ​​measured in (1) and (2). Rate of change (%) = |(initial value) - (value after accelerated test)| / (initial value) x 100 The evaluation criteria are as follows: ◎: Less than 2.0 ○: 2.0 or more and less than 5.0 △: 5.0 or more and less than 7.0 ×:7.0 or higher

[0084] [Table 2]

[0085] Regarding hydrophilicity, Examples 1 to 8 and Comparative Examples 1, 3, and 4 in which the hydrophilicity-imparting agent contained cis-amide (A) and trans-amide (B) had small contact angles, indicating good hydrophilicity. On the other hand, Comparative Example 2 in which the hydrophilicity-imparting agent consisted only of cis-amide (A) had a large contact angle and low hydrophilicity. This is believed to be because the trans-amide (B) contributes to hydrophilicity, and the more the amount added, the more hydrophilic the resin becomes. Comparative Example 2 did not contain trans-amide (B), and it is believed that the resin surface exhibited hydrophobicity.

[0086] Concerning the coefficient of friction, Examples 1 to 8 and Comparative Examples 2 and 3 showed good slip properties, while Comparative Examples 1 and 4 were evaluated as having low slip properties. Since the cis-amide (A) has a lower melting point than the trans-amide (B), it is believed that the slip properties of the resin surface decreased when the content of the trans-amide (B) was high, as in Comparative Example 1. For the same reason, it is believed that the slip properties of the surface also decreased when a saturated amide was included (Comparative Example 4).

[0087] Regarding stability over time, the rate of change in both hydrophilicity and friction coefficient was small in Examples 1 to 8 and Comparative Example 2, while the rate of change in Comparative Examples 1, 3, and 4 was large.

[0088] From the above results, it was found that by adding a hydrophilicity-imparting agent containing a cis-amide (A) and a trans-amide in a specified ratio to a resin, a resin composition which combines hydrophilicity and slipperiness and also has excellent storage stability could be obtained. [Industrial Applicability]

[0089] According to the present invention, a hydrophilicity-imparting agent capable of imparting hydrophilicity and low friction to a resin and a resin composition containing the same can be obtained. Therefore, the hydrophilicity-imparting agent and the resin composition are very useful for various applications.

Claims

1. a cis-amide which is an amide of an aliphatic amine a having 16 to 24 carbon atoms and a fatty acid b having 16 to 24 carbon atoms, wherein at least one of the aliphatic amine a and the fatty acid b contains a cis-unsaturated structure and does not contain a trans-unsaturated structure in the structure; an amide of an aliphatic amine c having 16 to 24 carbon atoms and a fatty acid d having 16 to 24 carbon atoms, wherein at least one of the aliphatic amine c and the fatty acid d contains a trans-type unsaturated structure and does not contain a cis-type unsaturated structure in the structure; The hydrophilicity-imparting agent, wherein the mass ratio of the cis-amide to the trans-amide is 99.9:0.1 to 50:

50.

2. 100 parts by mass of resin; 0.5 to 30 parts by mass of the hydrophilicity imparting agent according to claim 1; A resin composition comprising:

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