Composition, and compositions for viscosity enhancement

Abstract

A purpose of the present invention is to provide a composition which is highly viscous although giving a refreshing touch. The present invention relates to a composition characterized by including a compound (a) and a compound (b), wherein the compound (a) includes a monomer unit represented by a specific general formula and the compound (b) is a polyhydric alcohol. The present invention further relates to: a composition for viscosity enhancement for a composition containing the compound (a), the composition for viscosity enhancement including a polyhydric alcohol as an active ingredient; and a composition for viscosity enhancement for a composition containing a polyhydric alcohol, the composition for viscosity enhancement including the compound (a) as an active ingredient.

Description

Composition and viscosity enhancing composition

[0001] The present disclosure relates to compositions containing polyamino acid derivatives and polyhydric alcohols.

[0002] Polyacrylic acid polymers, such as carboxyvinyl polymers, have traditionally been used as thickeners in cosmetics, etc. Although a small amount of carboxyvinyl polymer can produce a moist gel, from the perspective of environmental considerations, bio-based thickeners that can replace carboxyvinyl polymers are desired.

[0003] Meanwhile, natural polymers such as xanthan gum and other polysaccharides have traditionally been used as bio-based thickeners, but xanthan gum lacks a refreshing feel when applied to the skin and has the problem of being sticky.

[0004] Furthermore, polyamino acid derivatives having specific structural units made from amino acids have been reported as biodegradable polymers, and it has been reported that these polyamino acid derivatives can be used as thickeners and other applications (Patent Documents 1 and 2).

[0005] JP 2005-344061 A JP 2019-089897 A

[0006] However, the polyamino acid derivatives of Patent Documents 1 and 2 have a refreshing feel to the touch, but have lower viscosity than conventional thickeners such as xanthan gum. An object of the present invention is to provide a composition that has high viscosity while providing a refreshing feel to the touch.

[0007] As a result of intensive research conducted by the present inventors to solve the above-mentioned problems, they discovered that the above-mentioned problems can be solved by using a polyamino acid derivative having a specific structure in combination with a polyhydric alcohol, and thus completed the present invention.

[0008] That is, the present invention is as follows: [1] A composition comprising a compound (a) and a compound (b), wherein the compound (a) comprises α- or β-polyaspartic acid monomer units A-U represented by the following general formula (1) and α- or β-polyaspartic acid monomer units B-U represented by the following general formula (2), the ratio of the mole percentage of the monomer units A-U to the mole percentage of the monomer units B-U in the compound (a), (A-U) / (B-U), is 40 / 60 to 60 / 40, and the compound (b) is a polyhydric alcohol.

[0009] (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms.

[0010] (In the formula, R ２ represents a group containing a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom.) [2] The composition according to [1], wherein the compound (a) further contains succinimide monomer units C-U represented by the following general formula (3), and the ratio of the mole percentage of the total of the monomer units A-U and B-U to the mole percentage of the monomer units C-U in the compound (a), [(A-U) + (B-U)] / (C-U), is 80 / 20 to 99 / 1.

[0011] [3] The composition according to [1] or [2], wherein the compound (a) further contains an α-type or β-type polyaspartic acid monomer unit Crosslink-U represented by the following general formula (4):

[0012] (In the formula, the wavy line indicates a crosslinking site.) [4] The composition according to [2], wherein the compound (a) further contains an α-type or β-type polyaspartic acid monomer unit Crosslink-U represented by the following general formula (4):

[0013] (In the formula, the wavy line indicates a crosslinking site.) [5] The composition according to any one of [1] to [4], wherein the hydroxyl value of the compound (a) is 80 mgKOH / g to 170 mgKOH / g. [6] The composition according to [3] or [4], wherein the amount of crosslinking of the compound (a) is 0.1 mol % to 2.0 mol %. [7] The composition according to any one of [1] to [6], wherein the weight ratio of the compound (b) to the compound (a) in the composition is 0.1 to 35.0. [8] The composition according to any one of [1] to [7], wherein the content of the compound (a) in the composition is 0.1 wt % to 20.0 wt % with respect to the total composition. [9] The composition according to any one of [1] to [8], wherein the content of the compound (b) in the composition is 0.1 wt % to 35.0 wt % with respect to the total composition.

[10] The composition according to any one of [1] to [9], wherein the content of the compound (b) in the composition is 0.1 wt % to 35.0 wt % with respect to the total composition.

[11] A composition for enhancing viscosity, comprising a compound (a) and containing a polyhydric alcohol as an active ingredient, wherein the compound (a) comprises α- or β-polyaspartic acid monomer units A-U represented by the following general formula (1) and α- or β-polyaspartic acid monomer units B-U represented by the following general formula (2), and the ratio (A-U) / (B-U) of the mole percentage of the monomer units A-U to the mole percentage of the monomer units B-U in the compound (a) is 40 / 60 to 60 / 40.

[0014] (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms.

[0015] (In the formula, R ２ represents a group containing a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom.)

[12] A composition for enhancing viscosity of a polyhydric alcohol-containing composition, the composition comprising compound (a) as an active ingredient, wherein the compound (a) comprises α- or β-type polyaspartic acid monomer units A-U represented by the following general formula (1) and α- or β-type polyaspartic acid monomer units B-U represented by the following general formula (2), and the ratio of the mol% of the monomer units A-U to the mol% of the monomer units B-U in the compound (a), (A-U) / (B-U), is 40 / 60 to 60 / 40.

[0016] (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms.

[0017] (In the formula, R ２ represents a group containing a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom.

[0018] The inventions according to [1] to [4] can also be said to be inventions according to the following

[13] to

[16] , respectively:

[13] A composition comprising a compound (a) and a compound (b), wherein the compound (a) comprises a structure represented by the following general formula (11), and the compound (b) is a polyhydric alcohol.

[0019] (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms, and R ２ represents a group containing a hydrocarbon group having 1 to 20 carbon atoms, which may contain a heteroatom. n and m respectively represent the number of moles of α-type or β-type polyaspartic acid monomer units A-U and B-U per mole of the compound (a). The molar ratio n / m of the monomer units A-U to B-U is 40 / 60 to 60 / 40. The bonding form of the monomer units A-U and B-U may be any of random, block, and tapered.)

[14] The composition according to

[13] , wherein the structure represented by the general formula (11) includes a structure represented by the following general formula (12):

[0020] (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms, and R ２represents a group containing a hydrocarbon group having 1 to 20 carbon atoms, which may contain a heteroatom. n and m respectively represent the number of moles of α-type or β-type polyaspartic acid monomer units A-U and B-U per molecule of the compound (a). l represents the number of moles of succinimide monomer units C-U per molecule of the compound (a). The molar ratio n / m of the monomer units A-U to B-U is 40 / 60 to 60 / 40, and the ratio (n + m) / l of the total number of moles of the monomer units A-U and B-U to the number of moles of the monomer units C-U is 80 / 20 to 99 / 1. The bonding configuration of the monomer units A-U, B-U, and C-U may be random, block, or tapered.)

[15] The composition according to

[13] , wherein the structure represented by the general formula (11) includes a structure represented by the following general formula (13):

[0021] (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms, and R ２ represents a group containing a hydrocarbon group having 1 to 20 carbon atoms, which may contain a heteroatom. n and m respectively represent the number of moles of α-type or β-type polyaspartic acid monomer units A-U and B-U per molecule of the compound (a). o represents the number of moles of α-type or β-type polyaspartic acid monomer units Crosslink-U having a crosslinked moiety per molecule of the compound (a). The wavy line in Crosslink-U represents the crosslinked moiety. The molar ratio n / m of the monomer units A-U and B-U is 40 / 60 to 60 / 40. The bonding form of the monomer units A-U, B-U, and Crosslink-U may be any of random, block, and tapered.

[0022]

[16] The composition according to

[13] , wherein the structure represented by the general formula (11) is a slightly crosslinked modified polyamino acid derivative represented by the following general formula (14):

[0023]

[0024] (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms, and R ２represents a group containing a hydrocarbon group having 1 to 20 carbon atoms, which may contain a heteroatom. n and m respectively represent the number of moles of α-type or β-type polyaspartic acid monomer units A-U and B-U per molecule of the compound (a). l represents the number of moles of succinimide monomer units C-U in the molecule. o represents the number of moles of α-type or β-type polyaspartic acid monomer units Crosslink-U having a crosslinking moiety per molecule of the compound (a). The wavy line in Crosslink-U represents a crosslinking moiety. The molar ratio n / m of the monomer units A-U and B-U is 40 / 60 to 60 / 40, and the ratio (n + m) / l of the total number of moles of the monomer units A-U and B-U to the number of moles of the monomer units C-U is 80 / 20 to 99 / 1. The bonding form of the monomer units A-U, B-U, C-U, and Crosslink-U may be any of random, block, and tapered.

[0025] According to the present invention, a composition that provides a refreshing feel while having high viscosity can be provided. Furthermore, when used as an external preparation for skin, the composition also provides an excellent smooth and moist feel to the skin immediately after application.

[0026] The present invention will be described in further detail below, but the present invention is not limited to the following embodiments.

[0027] Unless otherwise specified, the expressions "XX to YY" or "XX to YY" representing a range of values ​​mean a range of values ​​including the lower and upper limits, which are the endpoints. When a range of values ​​is described in stages, the upper and lower limits of each range can be combined in any way.

[0028] In order to solve the above-mentioned problems, each aspect of the present invention employs the following configuration: A first aspect is a composition containing a compound (a) and a compound (b), wherein the compound (a) contains α- or β-polyaspartic acid monomer units A-U represented by the following general formula (1) and α- or β-polyaspartic acid monomer units B-U represented by the following general formula (2), the ratio of the mole percentage of the monomer units A-U to the mole percentage of the monomer units B-U in the compound (a), (A-U) / (B-U), is 40 / 60 to 60 / 40, and the compound (b) is a polyhydric alcohol.

[0029] (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms.

[0030] (In the formula, R ２ represents a group containing a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom.

[0031] The second aspect is a viscosity-enhancing composition containing the compound (a) and containing a polyhydric alcohol as an active ingredient.

[0032] The third aspect is a composition for enhancing viscosity of a polyhydric alcohol-containing composition, which contains the compound (a) as an active ingredient.

[0033] A fourth aspect is a composition for increasing the viscosity of a composition, which comprises the compound (a) and the compound (b) as active ingredients.

[0034] <First Aspect> Each aspect of the present invention will be described below. The composition of the first aspect contains compound (a) and compound (b).

[0035] [Compound (a)] Compound (a) contains an α- or β-polyaspartic acid monomer unit A-U represented by the following general formula (1) and an α- or β-polyaspartic acid monomer unit B-U represented by the following general formula (2):

[0036] (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms.

[0037] (In the formula, R ２ represents a group containing a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom.

[0038] Compound (a) is a polyaspartic acid derivative having α-type or β-type polyaspartic acid monomer units A-U and B-U as repeating units. By using compound (a) in combination with compound (b), a composition with high viscosity can be obtained. This is because the R ２ and the hydroxyl group of compound (b) interact with each other via water in the aqueous solution, thereby synergistically improving the viscosity.

[0039] In addition to the monomer units AU and BU, the compound (a) preferably further contains a succinimide monomer unit CU represented by the following general formula (3) as a repeating unit:

[0040]

[0041] Furthermore, in addition to the monomer units A-U and B-U, it is preferable that the copolymer further contains an α- or β-type polyaspartic acid monomer unit Crosslink-U represented by the following general formula (4) as a repeating unit, and it is more preferable that the copolymer further contains a polyaspartic acid monomer unit Crosslink-U as a repeating unit in addition to the monomer units A-U, B-U, and C-U.

[0042] (In the formula, the wavy lines indicate crosslinking sites.)

[0043] In general formula (1), R １is not particularly limited as long as it contains a hydrocarbon group having 3 to 22 carbon atoms, and the hydrocarbon group having 3 to 22 carbon atoms may be saturated or unsaturated. Examples of the hydrocarbon group having 3 to 22 carbon atoms include linear alkyl groups such as propyl, butyl, pentyl, hexyl, octyl, dodecyl, and octadecyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, and isohexyl; cycloalkyl groups such as cyclobutyl, cyclopentyl, and cyclohexyl; cycloalkylalkyl groups such as cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclobutylethyl, cyclopentylethyl, cyclohexylethyl, cyclobutylpropyl, cyclopentylpropyl, cyclohexylpropyl, cyclobutylbutyl, cyclopentylbutyl, and cyclohexylbutyl; and alkenyl groups such as propenyl, butenyl, pentenyl, and hexenyl. Among these, alkyl groups are preferred.

[0044] The number of carbon atoms in the hydrocarbon group having 3 to 22 carbon atoms is preferably 6 to 20, and more preferably 8 to 18. The hydrocarbon group having 3 to 22 carbon atoms may be branched or linear, and is preferably linear.

[0045] R １ may further contain a substituent other than the hydrocarbon group having 3 to 22 carbon atoms in addition to the hydrocarbon group having 3 to 22 carbon atoms. Specific examples of the substituent other than the hydrocarbon group having 3 to 22 carbon atoms include an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a hydroxyl group, a carboxyl group, an amino group, etc. For example, R １ is a polyoxyalkylene group and a hydrocarbon group R having 3 to 22 carbon atoms １１ and the like may be a group represented by the following general formula (5) to which

[0046] -(C ｎ H ２ｎ O) ｍ -R １１ (5) In the formula (5), n is preferably 2 to 10, more preferably 2 to 4. m is preferably 1 to 30, more preferably 1 to 10.１１ The above description of the hydrocarbon group having 3 to 22 carbon atoms is applicable to the group represented by the formula (5). １ The group may be a group represented by the following general formula (6) in which a polyoxyethylene group and an octyl group are bonded.

[0047] -(C ２ H ４ O) ｍ -C ８ H １７ (6) With respect to m in equation (6), the above explanation regarding m in equation (5) is applied.

[0048] The compound (a) may contain one type of monomer unit A-U alone or two or more types.

[0049] In general formula (2), R ２is not particularly limited as long as it is a group containing a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom. Examples of the hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom include hydrophilic saturated or unsaturated hydrocarbon groups which contain a nitrogen atom, an oxygen atom, a sulfur atom, or the like.Specific examples thereof include hydroxyalkyl groups such as a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxypentyl group, a hydroxyhexyl group, a hydroxyheptyl group, and a hydroxyoctyl group; dialkylamino groups such as a dimethylamino group, a diethylamino group, a dipropylamino group, and a dibutylamino group; azapropyl group, azabutyl group, azapentyl group, azahexyl group, N,N-dimethylaminobutyl group, N,N-dimethylaminopropyl group, N,N-dimethylaminoethyl group, and N,N-dimethylaminoethyl group; azaalkyl groups such as a methylaminomethyl group, an N,N-diethylaminobutyl group, an N,N-diethylaminopropyl group, an N,N-diethylaminoethyl group, and an N,N-diethylaminomethyl group; azaalkenyl groups such as an azapropenyl group, an azabutenyl group, an azapentenyl group, an azahexenyl group, an N,N-dimethylaminopropenyl group, an N,N-dimethylaminobutenyl group, an N,N-dimethylaminohexenyl group, and an N,N-diethylaminopropenyl group; oxaethyl group, oxapropyl group, oxabutyl group, oxapentyl group, and an oxalkenyl group; oxaalkyl groups such as oxahexyl, oxaheptyl, and oxaoctyl groups; oxaalkyl groups such as oxapropenyl, oxabutenyl, oxopentenyl, oxahexenyl, oxaheptenyl, and oxaoctenyl groups; thioalkyl groups such as thiobutyl, thiopentyl, thiohexyl, thioheptyl, and thiooctyl groups; thioalkenyl groups such as thiopentenyl, thiohexenyl, thioheptenyl, and thiooctenyl groups; hydroxyethoxyethyl, hydroxyethoxypropyl, and hydroxyethoxypropyl groups. hydroxyalkoxyalkyl groups such as methoxyethoxyethyl group, methoxyethoxypropyl group, hydroxypropoxypropyl group, and hydroxypropoxybutyl group; alkoxyalkoxyalkyl groups such as methoxyethoxyethyl group, methoxyethoxypropyl group, methoxyethoxybutyl group, methoxypropoxyethyl group, methoxypropoxypropyl group, and methoxypropoxybutyl group; dihydroxyalkyl groups such as dihydroxyethyl group, dihydroxypropyl group, and dihydroxybutyl group; amino groups (-NH) from D-glucamine. ２ and polyhydroxyalkyl groups such as groups excluding -.

[0050] The number of carbon atoms in the hydrocarbon group having 1 to 20 carbon atoms, which may contain a heteroatom, is preferably 1 to 10, more preferably 1 to 6, and even more preferably 2 to 6. The hydrocarbon group having 1 to 20 carbon atoms, which may contain a heteroatom, may be branched or linear, and is preferably linear.

[0051] The heteroatom is preferably one or more atoms selected from the group consisting of oxygen atoms and nitrogen atoms, and more preferably an oxygen atom.

[0052] R ２ is preferably a group selected from the group consisting of an N,N-dimethylaminopropyl group, an N,N-diethylaminopropyl group, a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxypentyl group, a hydroxyethoxyethyl group, a methoxymethyl group, a methoxyethyl group, a methoxypropyl group, a methoxybutyl group, a methoxypentyl group, an ethoxymethyl group, an ethoxyethyl group, an ethoxypropyl group, an ethoxybutyl group, an ethoxypentyl group, and a dihydroxypropyl group.

[0053] R ２ is more preferably a hydroxyalkyl group having 2 to 6 carbon atoms. Examples of the hydroxyalkyl group having 2 to 6 carbon atoms include a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxypentyl group, and a hydroxyhexyl group.

[0054] R ２ may further contain one or more sugar residues in addition to a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom. The sugar residue may be any of a monosaccharide, an oligosaccharide, or a polysaccharide. In the present invention, an oligosaccharide refers to a compound obtained by dehydration condensation of 2 to 10 monosaccharide molecules, and a polysaccharide refers to a compound obtained by dehydration condensation of 11 or more monosaccharide molecules. When the sugar residue is an oligosaccharide or a polysaccharide, the degree of condensation of the sugars in the sugar residue (i.e., the number of monosaccharides constituting the sugar residue) is, for example, preferably 2 to 10, more preferably 2 to 5, and even more preferably 2 to 3.

[0055] Examples of monosaccharides include tetroses such as D-erythrulose, D-erythrose, and D-threose; aldopentoses such as D-arabinose, L-arabinose, D-xylose, D-lyxose, L-lyxose, and D-ribose; ketopentoses such as D-xylulose, L-xylulose, D-ribulose, and L-ribulose; aldohexoses such as D-galactose, L-galactose, D-glucose, D-talose, and D-mannose; ketohexoses such as L-sorbose, D-tagatose, D-psicose, and D-fructose; branched sugars such as D-apiose and D-hamamelose; pentoses such as ribose, arabinose, and xylose; hexoses such as glucose, galactose, and fructose; amino sugars such as glucosamine and galactosamine; and derivatives of these monosaccharides.

[0056] Examples of oligosaccharides include homooligosaccharides containing only one of the above-mentioned monosaccharides, and heterooligosaccharides containing two or more of them. Examples of homooligosaccharides include xylooligosaccharides such as xylobiose, xylotriose, xylotetraose, and xylopentaose; galactooligosaccharides such as agarobiose and carabiose; glucooligosaccharides such as maltose, maltotriose, maltotetraose, maltopentaose, isomaltose, sophorose, cellobiose, cellotriose, cellotetraose, cellopentaose, trehalose, neotrehalose, and isotrehalose; mannooligosaccharides; and fructooligosaccharides such as inulobiose, inulotriose, inulotetraose, and inulopentaose. Examples of hetero-oligosaccharides include vicianose, isoprimeverose, sambubiose, primeverose, lycotetraose, solabioose, melibiose, manninotriose, lactose, licobiose, lycotriose, epicellobiose, sucrose, turanose, maltulose, isokestose, erlose, kestose, gentianose, lactulose, epigentibiose, isolichnose, umbelliferose, sesamos, raffinose, lychnose, lobinobiose, silanobiose, rutinose, chacotriose, solatriose, and α-glucan oligosaccharides (glucose oligomers having a degree of polymerization of 2 to 10).

[0057] Examples of polysaccharides include xanthan gum, cellulose, guar gum, starch, pullulan, dextran, fructan, mannan, agar, carrageenan, chitin, chitosan, pectin, alginic acid, starch, glycogen, and hyaluronic acid.

[0058] R when further containing a sugar residue ２ Specific examples of the above include groups in which one or more hydroxyl groups or amino groups in a hydrocarbon group having 1 to 20 carbon atoms and containing a heteroatom are glycosidicly linked to one or more hydroxyl groups in a sugar, and more specific examples include groups represented by the following general formula (7) in which a hydroxypropyl group is glycosidicly linked to a hydroxyl group in cellulose:

[0059] -C ３ H ６ O-(C ６ H １０ O ５ ) ｎ (7)

[0060] The monomer unit BU contained in the compound (a) may contain one type alone or two or more types.

[0061] The bonding form of the monomer units A-U, B-U, C-U, and Crosslink-U may be any of random, block, and tapered. From the viewpoint of simultaneously improving the water solubility and viscosity of the polyamino acid derivative, the bonding form of the monomer units A-U, B-U, and C-U is preferably linear.

[0062] In compound (a), the ratio of the mole percent of monomer units A-U to the mole percent of monomer units B-U (also represented as (A-U) / (B-U)) is 40 / 60 to 60 / 40, preferably 45 / 55 to 60 / 40, and more preferably 50 / 50 to 60 / 40. Within the above range, excellent compatibility with water and improved viscosity are achieved. In the present disclosure, the ratio is １ The value is calculated from H NMR. １ The detailed calculation method from H NMR will be explained in the Examples.

[0063] The ratio (A-U) / (B-U) can also be calculated from the amounts of the raw materials used, by dividing the total number of moles of amine A added during synthesis by the total number of moles of amine B added during synthesis.

[0064] In compound (a), the ratio of the molar percentage of the total of the monomer units A-U and B-U to the molar percentage of the monomer units C-U (also represented as [(A-U) + (B-U)] / (C-U)) is 80 / 20 to 99 / 1, preferably 85 / 15 to 98 / 2, more preferably 90 / 10 to 97 / 3, and even more preferably 90 / 10 to 95 / 5. In the present disclosure, the ratio is １ The value is calculated from H NMR. １ The detailed calculation method from H NMR will be explained in the Examples.

[0065] The mol % of the monomer unit A-U in compound (a) is preferably 40 mol % to 60 mol %, more preferably 43 mol % to 58 mol %, and even more preferably 45 mol % to 57 mol %. In the present disclosure, the mol % of the monomer unit A-U in compound (a) refers to the amount (mol %) of the monomer unit A-U present in one molecule of compound (a). The mol % of A-U can be adjusted by the amounts of amine A and other raw materials, which will be described later, blended during synthesis.

[0066] The mol % of the monomer unit B-U in compound (a) is preferably 30 mol % to 60 mol %, more preferably 32 mol % to 50 mol %, and even more preferably 35 mol % to 45 mol %. In the present disclosure, the mol % of the monomer unit B-U in compound (a) refers to the amount (mol %) of the monomer unit B-U present in one molecule of compound (a). The mol % of B-U can be adjusted by the blending amounts of amine B (described below) and other raw materials during synthesis.

[0067] Here, the mole percentages of the monomer units A-U and B-U in the compound (a) are respectively: １The molar percentage of the monomer unit A-U is calculated from H NMR. Specifically, it is calculated using the obtained NMR spectrum according to the following formula: mol % of the monomer unit A-U=(peak integral value of the methyl group of amine A / 3)×100 / ((peak integral value of the methyl group of amine A / 3)+(peak integral value of the methylene group of amine B / 2)+(peak integral value of the methine group of succinimide)) mol % of the monomer unit B-U=(peak integral value of the methylene group of amine B / 2)×100 / ((peak integral value of the methyl group of amine A / 3)+(peak integral value of the methylene group of amine B / 2)+(peak integral value of the methine group of succinimide))

[0068] The mole percentages of the monomer units A-U and B-U in compound (a) can also be calculated from the amounts of the raw materials by the following formulas: Mol % of monomer units A-U = (total number of moles of amine A added during synthesis / total number of moles of polysuccinimide (PSI) added during synthesis) x 100 Mol % of monomer units B-U = (total number of moles of amine B added during synthesis / total number of moles of PSI added during synthesis) x 100

[0069] When compound (a) contains the monomer unit Crosslink-U represented by general formula (4), compound (a) is preferably a slightly crosslinked modified polyamino acid derivative. Here, "slightly crosslinked modified polyamino acid derivative" refers to a modified polyamino acid derivative having a crosslinking amount of 0.1 mol % to 2.0 mol %. "Slightly crosslinked" is distinguished from ordinary "crosslinked" in which the crosslinking amount exceeds 2.0 mol %. For example, because the crosslinking amount of a slightly crosslinked polymer is low, a solution of a given concentration does not gel and can maintain a certain fluidity.

[0070] When compound (a) contains the monomer unit Crosslink-U represented by general formula (4), the crosslinking amount in compound (a) (mol % of the monomer unit Crosslink-U in compound (a)) is preferably 0.1 mol % to 2.0 mol %, more preferably 0.3 mol % to 1.8 mol %, and even more preferably 0.5 mol % to 1.7 mol %. In the monomer unit Crosslink-U, the crosslinked moiety contains a structure derived from a crosslinking agent (described in detail in the production method described below). The crosslinking amount can be adjusted by the blending amounts of the crosslinking agent and other raw materials used during synthesis. The crosslinking amount (mol %) can be calculated by (total number of moles of crosslinking agent added during synthesis / total number of moles of polysuccinimide (PSI) added during synthesis) x 100.

[0071] The hydroxyl value of compound (a) is preferably 80 mgKOH / g or more, more preferably 100 mgKOH / g or more. On the other hand, it is preferably 170 mgKOH / g or less, more preferably 150 mgKOH / g or less. For example, it is 80 mgKOH / g to 170 mgKOH / g, or 100 mgKOH / g to 150 mgKOH / g. The hydroxyl value can be adjusted by the blending amounts of amine A and amine B, which will be described later. A method for calculating the hydroxyl value will be explained in the Examples.

[0072] The weight-average molecular weight (Mw) of compound (a) is not particularly limited, but is preferably 80,000 or more, more preferably 100,000 or more, and even more preferably 120,000 or more. It is also preferably 800,000 or less, more preferably 700,000 or less, and even more preferably 600,000 or less. For example, it is 80,000 to 800,000, 100,000 to 700,000, or 120,000 to 600,000. The weight-average molecular weight can be adjusted by the molecular weight of the polysuccinimide used in the synthesis and the types of amine A and amine B described below. The weight-average molecular weight here refers to a converted value measured by the GPC method (differential refractometer) using polystyrene as the standard substance. Specifically, it refers to the weight-average molecular weight measured using a G1000HHR column, a G4000HHR column, and a GMHHR-H column (TSKgel (registered trademark), manufactured by Tosoh Corporation) and dimethylformamide containing 10 mM lithium bromide as the eluent.

[0073] In compound (a) of this embodiment, the monomer units A-U, B-U, and C-U are a structural unit derived from amine A, a structural unit derived from amine B, and a structural unit derived from succinimide, respectively (which will be described in detail in the production method described below).

[0074] Compound (a) containing the monomer units A-U and B-U can be obtained by ring-opening polysuccinimide (PSI) using a monoamine. The monomer unit C-U is formed by remaining unreacted imide rings. When compound (a) contains the monomer unit Crosslink-U, compound (a) is obtained by further crosslinking a monoamine-modified polyamino acid derivative obtained by ring-opening polysuccinimide (PSI) using a monoamine with a trace amount of a crosslinking agent.

[0075] [Polysuccinimide (PSI)] Polysuccinimide (PSI) is a polymer represented by the following formula (8).

[0076] (In the formula, n=10 to 10000)

[0077] There are no particular limitations on the method for producing polysuccinimide (PSI). For example, it can be produced by heating aspartic acid in the presence of phosphoric acid in a vacuum at 170 to 190°C and dehydrating and condensing it. To obtain a polysuccinimide (PSI) with a higher molecular weight, the polysuccinimide (PSI) obtained as described above can be treated with a condensing agent such as dicyclohexylcarbodiimide. The molecular weight of the polysuccinimide (PSI) is not particularly limited. For example, the weight-average molecular weight is preferably 20,000 or more, more preferably 50,000 or more, and even more preferably 70,000 or more. The molecular weight of the polysuccinimide (PSI) is preferably 500,000 or less, and more preferably 200,000 or less. For example, the weight-average molecular weight is 20,000 or more and 500,000 or less, or 70,000 or more and 200,000 or less. The weight-average molecular weight herein refers to a converted value measured by a GPC method (differential refractometer) using polystyrene as a standard substance, and specifically refers to a weight-average molecular weight measured using a G1000HHR column, a G4000HHR column, and a GMHHR-H column (TSKgel (registered trademark), manufactured by Tosoh Corporation) and using dimethylformamide containing 10 mM lithium bromide as an eluent.

[0078] [Crosslinking Agent] The crosslinking agent according to this embodiment is not particularly limited as long as it can form a crosslinked moiety. Specific examples of crosslinking agents preferred for forming an amide bond used in the crosslinked moiety include polyfunctional amines.

[0079] The polyfunctional amine is preferably an amine having at least two primary and / or secondary amino groups. Examples of diamine compounds include aliphatic diamines such as ethylenediamine and hexamethylenediamine, and aliphatic diamines containing an aromatic ring such as xylenediamine; alicyclic diamines such as norbornenediamine; ether-based diamines such as 1,2-bis(2-aminoethoxy)ethane (AEE), diethylene glycol bis(3-aminopropyl)ether (bis[2-(3-aminopropoxy)ethyl ether (APEE)), polyoxyethylenediamine, and polyoxypropylenediamine; amino acids and derivatives thereof having an amino group in the side chain, such as lysine and ornithine; and monoamino compounds linked by disulfide bonds, such as cystine and cystamine, and derivatives thereof. The polyfunctional amine preferably does not contain the above amino acids or derivatives thereof. The polyfunctional amine is preferably an ether-based diamine, as described above, from the viewpoint of having a flexible structure, making it difficult for insoluble matter to be generated during the crosslinking reaction, and from the viewpoint of making the crosslinking reaction easy to control.

[0080] Examples of polyfunctional amine compounds other than diamines include tris(2-aminoalkyl)amines (wherein the carbon atom number of the alkyl is preferably 1 to 5, and more preferably 2 to 4), such as tris(2-aminoethyl)amine (TREN) and tris(3-aminopropyl)amine; diethylenetriamine, triethylenetetramine, tetraethylenepentamine, and pentaethylenehexamine.

[0081] Among these, preferred examples of polyfunctional amines include 1,2-bis(2-aminoethoxy)ethane (AEE), bis[2-(3-aminopropoxy)ethyl ether (APEE), and tris(2-aminoethyl)amine (TREN).

[0082] One method for reacting polysuccinimide with a polyfunctional amine is, for example, a method in an organic solvent. This will be explained using an example in which the polyfunctional amine is a diamine. In the method for reacting polysuccinimide with a diamine in an organic solvent, polysuccinimide is dissolved in an aprotic polar organic solvent such as dimethylformamide (DMF), dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), dimethylimidazolidinone (DMI), dimethyl sulfoxide (DMSO), or sulfolane, and then a diamine or a solution of a diamine in the organic solvent is added dropwise. The amount of organic solvent used to dissolve the polysuccinimide is not particularly limited, but is typically adjusted to a polymer concentration of 1 to 50% by mass.

[0083] The temperature at which the polysuccinimide and diamine are reacted is not particularly limited, but is, for example, from room temperature to 80°C.

[0084] The reaction conditions (reaction temperature, reaction time, reaction concentration, amount of diamine used, etc.) are not particularly limited, but it is desirable to set the conditions such that the entire reaction solution does not gel.

[0085] [Monoamine] As the monoamine, a monoamine represented by the following general formula (9) (sometimes referred to as amine A) and a monoamine represented by the following general formula (10) (sometimes referred to as amine B) are used. １ -NH ２ (9) (wherein, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms. ２ -NH ２ (10) (wherein, R ２ represents a group containing a hydrocarbon group which may contain a heteroatom.

[0086] R in general formula (9) １ Regarding R in general formula (1), １ The explanation regarding R in general formula (10) is also incorporated herein by reference. ２ Regarding R in general formula (1), ２The monoamine represented by the general formula (9) and the monoamine represented by the general formula (10) may be commercially available products, or may be prepared by a known method.

[0087] [Method for Producing Compound (a)] Examples of methods for producing compound (a) include a method for ring-opening reaction of polysuccinimide (PSI) using polysuccinimide (PSI) and a monoamine. Furthermore, when compound (a) contains the monomer unit Crosslink-U, a crosslinking agent such as a polyfunctional amine compound is used in addition to polysuccinimide (PSI) and a monoamine in the ring-opening reaction of polysuccinimide (PSI). The order in which the crosslinking agent and the monoamine are added is not particularly limited. The monoamine may be added first and then the crosslinking agent, or the monoamine and crosslinking agent may be added simultaneously, or the crosslinking agent may be added first and then the monoamine. From the viewpoint of easy control of the crosslinking amount, it is preferable to add the crosslinking agent first, and then add the monoamine after the crosslinking reaction has progressed.

[0088] For example, when a polyfunctional amine compound is used as a crosslinking agent, a method of ring-opening polysuccinimide (PSI) by reacting polysuccinimide (PSI) with a trace amount of a crosslinking agent such as a polyfunctional amine compound, followed by adding a monoamine and reacting the polysuccinimide (PSI) with the monoamine can be mentioned. Polysuccinimide (PSI) is reacted with a trace amount of a crosslinking agent such as a polyfunctional amine compound, followed by reacting the polysuccinimide (PSI) with the monoamine, thereby opening the imide ring of the polysuccinimide (PSI). Furthermore, since a trace amount of a crosslinking agent such as a polyfunctional amine compound is used, the resulting polyamino acid derivative has a trace amount of crosslinked structure. The total amount of the crosslinking agent and monoamine used may be less than 1 equivalent relative to the equivalent of the monomer unit of polysuccinimide (PSI), which may result in unreacted imide rings remaining, or may be more than 1 equivalent, which may result in no unreacted imide rings remaining.

[0089] In the method for producing compound (a), it is preferable that the monoamine contains a monoamine represented by the above general formula (9) and a monoamine represented by the general formula (10), and the molar ratio of amine A to amine B is 45 / 55 to 60 / 40. It is more preferable that the monoamine contains amine A and amine B, and the molar ratio of amine A to amine B is 50 / 50 to 60 / 40.

[0090] In the method for producing compound (a), the monoamine may contain amine A and amine B, and may also contain a monoamine other than amine A and amine B. In this case, the total molar amount of amine A and amine B in the monoamine is preferably 80% or more, more preferably 90% or more, and even more preferably 95% or more. Furthermore, the monoamine may be amine A and amine B.

[0091] The unreacted imide ring may remain as it is, or may be further opened with another monoamine, or, if desired, may be opened with a substituted amine such as ethanolamine, cysteamine, or dibutylamine.

[0092] "Organic Solvent" In the method for producing compound (a), the organic solvent is not particularly limited as long as it substantially dissolves polysuccinimide (PSI), the crosslinking agent, and the monoamine and / or does not substantially inhibit the progress of the reaction.

[0093] Specific examples of the organic solvent include aprotic polar organic solvents such as dimethylformamide (DMF), dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), dimethylimidazolidinone (DMI), dimethyl sulfoxide (DMSO), and sulfolane, which can be used alone or in combination.

[0094] "Amount of Crosslinking Agent Used" When compound (a) contains the monomer unit Crosslink-U, the amount of crosslinking agent used is not particularly limited, but is preferably an amount that can introduce a small amount of crosslinked structure to the extent that gelation does not occur. For example, in the final synthesized slightly crosslinked modified polyamino acid derivative, the amount of crosslinking may be 0.1 mol% to 2.0 mol%. 0.3 mol% to 1.8 mol% is preferred, 0.4 mol% to 1.7 mol% is more preferred, and 0.5 mol% to 1.5 mol% is even more preferred. For example, when a polyfunctional amine is used as the crosslinking agent, the amount of polyfunctional amine used is 0.1 mol to 2.0 mol, preferably 0.2 mol to 1.5 mol, more preferably 0.3 mol to 1.3 mol, and even more preferably 0.4 mol to 1.0 mol, relative to 100 moles of the total number of moles of polysuccinimide added during synthesis. When the amount of polyfunctional amine used is 2 moles relative to the total moles of polysuccinimide added during synthesis, 100 moles, it is simply referred to as "the amount of polyfunctional amine used is 2 mole %." In the present disclosure, "the total moles of polysuccinimide (PSI) added during synthesis" means the value obtained by dividing the weight of polysuccinimide added during synthesis of compound (a) by the molecular weight of the repeating unit of polysuccinimide.

[0095] "Amount of Monoamine Used" The total amount of monoamine used is not particularly limited as long as it is substantially soluble in the organic solvent and / or does not substantially inhibit the progress of the reaction. The amount used is generally 0.1 to 10 equivalents, preferably 0.1 to 1.2 equivalents, relative to the equivalent of the monomer unit of polysuccinimide (PSI).

[0096] "Basic catalyst" In the method for producing compound (a), a catalyst may not be used, or a basic catalyst may be used. The optionally used basic catalyst is not particularly limited as long as it substantially accelerates the reaction rate. Specific examples of the basic catalyst include aliphatic tertiary amines such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisopropylethylamine (DIEA), triethanolamine, and triethylenediamine (DABCO), alicyclic tertiary amines such as N-methylmorpholine, aromatic tertiary amines such as dimethylaniline and diethylaniline, and tetramethylguanidine, which may be used alone or in combination.

[0097] "Amount of basic catalyst used" In the method for producing compound (a), the amount of basic catalyst used is not particularly limited as long as it substantially accelerates the reaction rate. The amount of the basic catalyst used is generally 0 to 2 equivalents relative to the equivalent of the monoamine.

[0098] "Reaction Temperature" In the method for producing compound (a), the reaction temperature is not particularly limited as long as it can substantially maintain the progress of the reaction. The reaction temperature is generally selected from a temperature range of 5 to 150°C. The reaction temperature can also be optimally selected from the perspective of the monoamine used, shortening the reaction time, improving the reaction rate, and the like. The method for producing compound (a) preferably includes a crosslinking reaction step in which a crosslinking agent is first added and the crosslinking reaction proceeds, and a monoamine reaction step in which a monoamine is then added. In this case, the temperature of the crosslinking reaction and the temperature of the monoamine reaction may be the same or different. It is preferable that the temperature of the crosslinking reaction is lower than the reaction temperature after the addition of the monoamine. In the crosslinking reaction step in which a crosslinking agent is added to polysuccinimide (PSI) and the crosslinking reaction proceeds, the reaction temperature may be 120°C or lower, or may be 100°C or lower, or may be 20°C or higher. For example, when the crosslinking agent is an ether-based diamine or tris(2-aminoalkyl)amine, the reaction temperature in the crosslinking reaction step is preferably 100°C or lower, more preferably 80°C or lower, even more preferably 60°C or lower, and may be 50°C or lower. Alternatively, it may be 20°C or higher. In the crosslinking reaction step, as long as the reaction temperature is within the above range, crosslinking can proceed uniformly. By the above production method, a compound (a) with high viscosity can be obtained.

[0099] "Concentration of Reaction System" The concentration of the reaction system employed in the method for producing compound (a) is not particularly limited as long as it can substantially maintain the progress of the reaction. The concentration of the reaction system is selected based on the concentration of polysuccinimide (PSI), and the polysuccinimide (PSI) concentration is generally selected from a concentration range of 1 to 50% by weight. The concentration of the reaction system can also be selected from a polysuccinimide (PSI) concentration range of 1 to 50% by weight to be optimal for the monoamine used.

[0100] <Method for isolating compound (a)> In the method for producing compound (a), the method for isolating the produced polymer from the reaction solution after the reaction is completed is not particularly limited as long as it can isolate the reaction product with the desired purity. The isolation method may be any known or publicly used method. Generally, known or publicly used isolation procedures such as concentration, recrystallization, or reprecipitation are used.

[0101] A specific example of the isolation method is a method in which, after completion of the reaction, an excess of a poor solvent (e.g., ethyl acetate, methyl alcohol, ethyl alcohol, isopropyl alcohol, etc.) is added to the reaction solution in which the reaction product is dissolved at an appropriate temperature, the precipitated reaction product is isolated by decantation, filtration, suction filtration, etc., and the crystals are thoroughly washed with a poor solvent that does not dissolve the crystals, followed by drying. Another specific example is a method in which, after completion of the reaction, the reaction solution in which the reaction product is dissolved is added to the same excess of a poor solvent as above at an appropriate temperature, and the precipitated reaction product is isolated, washed, and dried in the same manner as above.

[0102] In the method for producing compound (a), the resulting compound (a) may not be isolated, and the post-reaction mixture may be used as compound (a) as is. If necessary, only some of the unreacted raw materials other than the solvent may be removed and included in the composition of this embodiment. Alternatively, the solvent in the mixture may be increased or decreased to adjust the concentration and obtain compound (a).

[0103] <Content of Compound (a)> The content of compound (a) in the composition according to this embodiment is preferably 0.1 wt% or more, more preferably 0.3 wt% or more, even more preferably 0.5 wt% or more, even more preferably 0.7 wt% or more, and even more preferably 0.9 wt% or more, based on the total composition. On the other hand, the content of compound (a) is preferably 20.0 wt% or less, more preferably 15.0 wt% or less, even more preferably 10.0 wt% or less, even more preferably 5.0 wt% or less, and even more preferably 2.0 wt% or less, based on the total composition. For example, it is 0.1 wt% to 20.0 wt%, 0.3 wt% to 15.0 wt%, 0.5 wt% to 10.0 wt%, 0.7 wt% to 5.0 wt%, or 0.9 wt% to 2.0 wt%. Compound (a) may be used singly or in combination of two or more types.

[0104] [Compound (b)] The composition according to this embodiment contains a polyhydric alcohol as compound (b). A polyhydric alcohol is an alcohol having two or more hydroxyl groups in the molecule. While a polyhydric alcohol itself has low viscosity, the use of a polyhydric alcohol in combination with compound (a) increases the viscosity of the composition compared to compound (a) alone and compound (b) alone. The polyhydric alcohol is not particularly limited, but examples include alkylene glycols such as propylene glycol, dipropylene glycol, 1,3-butanediol, and polyethylene glycol; glycerins such as glycerin, diglycerin, and polyglycerin; sugar alcohols such as xylitol, mannitol, galactite, and sorbitol; and others such as trimethylolethane, trimethylolpropane, and pentaerythritol. Glycerin and dihydric polyhydric alcohols are preferred. More specifically, one or more selected from the group consisting of 1,3-butanediol, dipropylene glycol, and glycerin are preferred. The polyhydric alcohols may be used alone or in combination of two or more.

[0105] The content of compound (b) in the composition according to this embodiment is preferably 0.1 wt% or more, more preferably 0.5 wt% or more, even more preferably 1.0 wt% or more, even more preferably 1.5 wt% or more, even more preferably 2.0 wt% or more, and most preferably 3.0 wt% or more, based on the total composition. On the other hand, the content of compound (b) is preferably 35.0 wt% or less, more preferably 33.0 wt% or less, even more preferably 31.0 wt% or less, even more preferably 20.0 wt% or less, even more preferably 15.0 wt% or less, and most preferably 7.0 wt% or less, based on the total composition. For example, it is 0.1 wt% to 35.0 wt%, 0.5 wt% to 33.0 wt%, 1.0 wt% to 31.0 wt%, 1.5 wt% to 20.0 wt%, 2.0 wt% to 15.0 wt%, or 3.0 wt% to 7.0 wt%.

[0106] The weight ratio of compound (b) to compound (a) in the composition according to this embodiment is preferably 0.1 or more, more preferably 0.5 or more, even more preferably 1.0 or more, even more preferably 1.5 or more, still more preferably 2.0 or more, and most preferably 3.0 or more. On the other hand, it is preferably 35.0 or less, more preferably 33.0 or less, even more preferably 31.0 or less, even more preferably 20.0 or less, even more preferably 15.0 or less, and most preferably 7.0 or less. For example, it is 0.1 to 35.0, 0.5 to 33.0, 1.0 to 31.0, 1.5 to 20.0, 2.0 to 15.0, or 3.0 to 7.0.

[0107] [Water] The composition of the present invention contains water. The water content in the composition is preferably 40.0 wt% or more, more preferably 50.0 wt% or more, even more preferably 60.0 wt% or more, even more preferably 70.0 wt% or more, and most preferably 80.0 wt% or more, based on the total composition. On the other hand, the water content is preferably 99.9 wt% or less, more preferably 98.0 wt% or less, even more preferably 97.0 wt% or less, even more preferably 96.0 wt% or less, and most preferably 95.0 wt% or less, based on the total composition. For example, the water content is 40.0 wt% to 99.9 wt%, 50.0 wt% to 98.0 wt%, 60.0 wt% to 97.0 wt%, 70.0 wt% to 96.0 wt%, or 80.0 wt% to 95.0 wt%.

[0108] The composition of this embodiment can be produced by a conventional method. That is, the order of mixing is not particularly limited, and the composition can be obtained by mixing compound (a), compound (b), and, if necessary, optional components in any order and by any method.

[0109] The composition of this embodiment provides a refreshing feel when applied to the skin, and is therefore excellent in feel when used. Therefore, the composition of this embodiment is suitable for use as an external preparation for skin, and specifically, is suitable for use as a cosmetic, quasi-drug, or pharmaceutical.

[0110] [Optional Components] The composition of this embodiment can optionally contain other components to the extent that the effects of the present invention are not impaired. Such optional components may be any components commonly used in external skin preparations such as cosmetics, and examples thereof include the following. Oily components include polar oils, volatile hydrocarbon oils, hydrocarbon oils, higher fatty acids, fats and oils, higher alcohols, waxes, ester oils, and silicone oils. Polar oils include synthetic ester oils such as isopropyl myristate, cetyl octanoate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyldecyl dimethyloctanoate, cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearate, and ethylene glycol di-2-ethylhexylate. , dipentaerythritol fatty acid ester, N-alkyl glycol monoisostearate, neopentyl glycol dicaprate, diisostearyl malate, glycerin di-2-heptylundecanoate, trimethylolpropane tri-2-ethylhexylate, trimethylolpropane triisostearate, pentaneerythritol tetra-2-ethylhexylate, glycerin tri-2-ethylhexylate, and trimethylolpropane triisostearate. Further examples include cetyl 2-ethylhexanoate, 2-ethylhexyl palmitate, glycerin trimyristate, tri-2-heptylundecanoic acid glyceride, castor oil fatty acid methyl ester, oleic acid oil, cetostearyl alcohol, acetoglyceride, 2-heptylundecyl palmitate, diisobutyl adipate, N-lauroyl-L-glutamic acid-2-octyldodecyl ester, di-2-heptylundecyl adipate, ethyl laurate, di-2-ethylhexyl sebacate, 2-hexyldecyl myristate, 2-hexyldecyl palmitate, 2-hexyldecyl adipate, diisopropyl sebacate, 2-ethylhexyl succinate, triethyl citrate, and octyl methoxycinnamate.Further, examples of natural oils include avocado oil, camellia oil, turtle oil, macadamia nut oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, camellia oil, castor oil, linseed oil, safflower oil, cottonseed oil, perilla oil, soybean oil, peanut oil, tea seed oil, Japanese kaya oil, rice bran oil, Chinese tung oil, Japanese tung oil, jojoba oil, germ oil, triglycerin, glycerin trioctanoate, glycerin triisopalmitate, and shea butter.

[0111] Examples of volatile hydrocarbon oils include isododecane and isohexadecane.

[0112] Examples of hydrocarbon oils include petrolatum, mineral oil, and squalane.

[0113] Examples of higher fatty acids include lauric acid, stearic acid, and oleic acid.

[0114] Examples of higher alcohols include stearyl alcohol, cetanol, and behenyl alcohol.

[0115] Examples of oils include olive oil, coconut oil, and horse oil.

[0116] Examples of waxes include candelilla wax, jojoba seed oil, and beeswax.

[0117] Examples of ester oils include triethylhexanoin and isopropyl myristate.

[0118] Examples of silicone oils include dimethicone and cyclopentasiloxane.

[0119] Examples of surfactants include anionic surfactants such as fatty acid soaps (sodium laurate, sodium palmitate, etc.), potassium lauryl sulfate, and alkyl sulfate triethanolamine ether; cationic surfactants such as stearyltrimethylammonium chloride, benzalkonium chloride, and laurylamine oxide; betaine surfactants (alkylbetaine, amidobetaine, sulfobetaine, etc.); imidazoline amphoteric surfactants (2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyloxy disodium salt, etc.); amphoteric surfactants such as acylmethyltaurine; sorbitan fatty acid esters (sorbitan monostearate, sorbitan sesquioleate, etc.); glycerin fatty acids (glycerin monostearate, etc.); polyglycerin fatty acids (polyglyceryl-10 laurate, etc.); propylene glycol fatty acid esters (propylene glycol monostearate, etc.); and hydrogenated castor oil. Examples of surfactants include corn oil derivatives, glycerin alkyl ethers, POE sorbitan fatty acid esters (POE sorbitan monooleate, polyoxyethylene sorbitan monostearate, etc.), POE sorbit fatty acid esters (POE-sorbit monolaurate, etc.), POE glycerin fatty acid esters (POE-glycerin monoisostearate, etc.), POE fatty acid esters (polyethylene glycol monooleate, POE distearate, etc.), POE alkyl ethers (POE 2-octyldodecyl ether, etc.), POE alkyl phenyl ethers (POE nonylphenyl ether, etc.), Pluronic (registered trademark) types, POE-POP alkyl ethers (POE-POP 2-decyltetradecyl ether, etc.), Tetronics, POE castor oil-hydrogenated castor oil derivatives (POE castor oil, POE hydrogenated castor oil, etc.), sucrose fatty acid esters, and nonionic surfactants such as alkyl glucosides.

[0120] The composition of this embodiment may contain a known thickener in addition to compound (a) and compound (b), to the extent that the effects of the present invention are not impaired. Examples of known thickeners include guar gum, quince seed, carrageenan, galactan, gum arabic, pectin, mannan, starch, xanthan gum, curdlan, methylcellulose, hydroxyethyl cellulose, carboxymethyl cellulose, methylhydroxypropyl cellulose, chondroitin sulfate, dermatan sulfate, glycogen, heparan sulfate, hyaluronic acid, sodium hyaluronate, tragacanth gum, keratan sulfate, chondroitin, mucoitin sulfate, hydroxyethyl guar gum, carboxymethyl guar gum, dextran, keratosulfuric acid, locust bean gum, succinoglucan, caronic acid, chitin, chitosan, carboxymethyl chitin, agar, polyvinyl alcohol, polyvinylpyrrolidone, carboxyvinyl polymer, alkyl-modified carboxyvinyl polymer, sodium polyacrylate, polyethylene glycol, and bentonite.

[0121] Examples of powders include powders such as mica, talc, kaolin, synthetic mica, calcium carbonate, magnesium carbonate, anhydrous silicic acid (silica), aluminum oxide, and barium sulfate, which may be surface-treated; inorganic pigments such as red iron oxide, yellow iron oxide, black iron oxide, cobalt oxide, ultramarine, iron blue, titanium oxide, and zinc oxide, which may be surface-treated; pearling agents such as titanium dioxide, fish phosphate foil, and bismuth oxychloride, which may be surface-treated; Examples of organic pigments include Red No. 202, Red No. 228, Red No. 226, Yellow No. 4, Blue No. 404, Yellow No. 5, Red No. 505, Red No. 230, Red No. 223, Orange No. 201, Red No. 213, Yellow No. 204, Yellow No. 203, Blue No. 1, Green No. 201, Purple No. 201, and Red No. 204, which may be coated; and organic powders such as polyethylene powder, polymethyl methacrylate, nylon powder, and organopolysiloxane elastomers.

[0122] Examples of the ultraviolet absorber include para-aminobenzoic acid-based ultraviolet absorbers, anthranilic acid-based ultraviolet absorbers, salicylic acid-based ultraviolet absorbers, cinnamic acid-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers, sugar-based ultraviolet absorbers, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, and 4-methoxy-4'-t-butyldibenzoylmethane.

[0123] The composition may also contain other ingredients such as ethanol, fragrances, preservatives, pH adjusters, and coloring agents.

[0124] When applied as an external preparation for skin, the formulation may take any of the commonly known forms such as lotion, emulsion, essence, cream, powder-containing formulation, etc.

[0125] (Shear Viscosity) The shear viscosity of the composition of this embodiment is preferably 400 mPa·s or more, more preferably 500 mPa·s or more, even more preferably 600 mPa·s or more, and even more preferably 700 mPa·s or more. On the other hand, it is preferably 6000 mPa·s or less, more preferably 5500 mPa·s or less, even more preferably 5000 mPa·s or less, and even more preferably 4500 mPa·s or less. For example, it is 400 mPa·s to 6000 mPa·s, 500 mPa·s to 5500 mPa·s, 600 mPa·s to 4500 mPa·s, or 700 mPa·s to 4000 mPa·s. The shear viscosity here is the value of shear viscosity at a shear rate of 15 / s measured using a rotational rheometer (R / Splus manufactured by Brookfield) under conditions of Measuring System C25-2, Con Truncation 0.046 mm, and a measurement temperature of 25°C, after preshearing at a shear rate of 10 / s for 15 seconds and allowing to stand for 30 seconds, while increasing the shear rate from 1 / s to 1000 / s.

[0126] <Second Aspect> The second aspect is a composition for enhancing the viscosity of a composition containing compound (a), which contains a polyhydric alcohol as an active ingredient. The polyhydric alcohol can enhance the viscosity of the composition containing compound (a).

[0127] The content of the polyhydric alcohol in the viscosity enhancing composition according to the second aspect is not particularly limited, and can be set according to the intended use. At least one of the viscosity enhancing composition and the composition containing compound (a) contains water. The content of water is not particularly limited, and can be set according to the intended use. The viscosity enhancing composition may contain an optional component in addition to the polyhydric alcohol. Furthermore, the content of compound (a) in the composition containing compound (a) is not particularly limited, and can be set according to the intended use. The composition containing compound (a) may contain an optional component in addition to compound (a).

[0128] The viscosity enhancing composition according to the second aspect is preferably used so that the weight ratio of compound (b) in the viscosity enhancing composition to compound (a) in the composition containing compound (a) is 0.1 or more, more preferably 0.5 or more, even more preferably 1.0 or more, even more preferably 1.5 or more, even more preferably 2.0 or more, and most preferably 3.0 or more. On the other hand, the weight ratio is preferably 35.0 or less, more preferably 33.0 or less, even more preferably 31.0 or less, even more preferably 20.0 or less, even more preferably 15.0 or less, and most preferably 7.0 or less. For example, the weight ratio is 0.1 to 35.0, 0.5 to 33.0, 1.0 to 31.0, 1.5 to 20.0, 2.0 to 15.0, or 3.0 to 7.0.

[0129] In addition to the above, the polyhydric alcohol, compound (a), and optional components in the second embodiment are the same as those described in the first embodiment.

[0130] <Third Aspect> The third aspect is a composition for enhancing the viscosity of a composition containing a polyhydric alcohol, the composition comprising compound (a) as an active ingredient. Compound (a) can enhance the viscosity of the composition containing a polyhydric alcohol.

[0131] The content of compound (a) in the viscosity enhancing composition according to the third aspect is not particularly limited, and can be set according to the intended use. At least one of the viscosity enhancing composition and the composition containing a polyhydric alcohol contains water. The content of water is not particularly limited, and can be set according to the intended use. The viscosity enhancing composition may contain optional components in addition to compound (a). Furthermore, the content of polyhydric alcohol in the composition containing a polyhydric alcohol is not particularly limited, and can be set according to the intended use. The composition containing a polyhydric alcohol may contain optional components in addition to the polyhydric alcohol.

[0132] The viscosity enhancing composition according to the third aspect is preferably used so that the weight ratio of compound (b) in the viscosity enhancing composition to compound (a) in the composition containing compound (a) is 0.1 or more, more preferably 0.5 or more, even more preferably 1.0 or more, even more preferably 1.5 or more, even more preferably 2.0 or more, and most preferably 3.0 or more. On the other hand, the weight ratio is preferably 35.0 or less, more preferably 33.0 or less, even more preferably 31.0 or less, even more preferably 20.0 or less, even more preferably 15.0 or less, and most preferably 7.0 or less. For example, the weight ratio is 0.1 to 35.0, 0.5 to 33.0, 1.0 to 31.0, 1.5 to 20.0, 2.0 to 15.0, or 3.0 to 7.0.

[0133] In addition to the above, the polyhydric alcohol, compound (a), and optional components in the third embodiment are the same as those described in the first embodiment.

[0134] <Fourth Aspect> The fourth aspect is a composition for increasing the viscosity of a composition, comprising compound (a) and compound (b) as active ingredients. Compound (a) and compound (b) can increase the viscosity of the composition.

[0135] The contents of compound (a) and compound (b) in the viscosity enhancing composition according to the fourth aspect are not particularly limited and can be adjusted according to the intended use. At least one of the viscosity enhancing composition and the composition whose viscosity is to be enhanced contains water. The content of water is not particularly limited and can be adjusted according to the intended use. The viscosity enhancing composition may contain optional components in addition to compound (a) and compound (b). The composition whose viscosity is to be enhanced according to the fourth aspect is not particularly limited, but is preferably a composition that is a skin topical preparation. The composition whose viscosity is to be enhanced can contain optional components to the extent that the effects of the present invention are not impaired.

[0136] The weight ratio of compound (b) to compound (a) in the viscosity-enhancing composition according to the fourth aspect is preferably 0.1 or more, more preferably 0.5 or more, even more preferably 1.0 or more, even more preferably 1.5 or more, still more preferably 2.0 or more, and most preferably 3.0 or more. On the other hand, it is preferably 35.0 or less, more preferably 33.0 or less, even more preferably 31.0 or less, even more preferably 20.0 or less, even more preferably 15.0 or less, and most preferably 7.0 or less. For example, it is 0.1 to 35.0, 0.5 to 33.0, 1.0 to 31.0, 1.5 to 20.0, 2.0 to 15.0, or 3.0 to 7.0.

[0137] In addition to the above, the compound (a), the compound (b), and the optional components in the fourth embodiment are the same as those described in the first embodiment.

[0138] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto.

[0139] Reference Example 1 Polyamino acid derivative 1, which is a slightly cross-linked modified polyamino acid derivative, was prepared as compound (a) according to the following procedure.

[0140] The raw materials used are as follows: (Raw Materials) Aspartic acid: manufactured by YIXING QIANCHENG BIO-ENGINEERING Co., Ltd., 99.97% purity Phosphoric acid: manufactured by Kanto Chemical Co., Ltd., 85% purity Dimethylformamide: manufactured by Kanto Chemical Co., Ltd., 99.5% purity n-Dodecylamine: manufactured by Kao Corporation, Farmin 20D 3-Amino-1-propanol: manufactured by Kanto Chemical Co., Ltd., 99% purity 1,2-bis(2-aminoethoxy)ethane (AEE): manufactured by Aldrich, 98% purity Ethyl acetate: manufactured by Godo Co., Ltd., 99% purity

[0141] <Synthesis of Polysuccinimide (PSI)> 160 parts of aspartic acid and 83 parts of 85% phosphoric acid were mixed in a mortar, transferred to a tray, and reacted for 6 hours at 190°C and 1.3 kPa. The reaction mixture was pulverized, washed with distilled water until the filtrate became neutral, and then vacuum dried at 80°C to obtain 115 parts of polysuccinimide (PSI) having a weight-average molecular weight of 80,000.

[0142] <Measurement of Weight-Average Molecular Weight of Polysuccinimide (PSI) and Polyamino Acid Derivative 1> In measuring the weight-average molecular weight of polysuccinimide (PSI), the polystyrene equivalent value was determined by GPC (differential refractometer). For the measurement, a G1000HHR column, a G4000HHR column, and a GMHHR-H column (TSKgel (registered trademark), manufactured by Tosoh Corporation) were used. Dimethylformamide containing 10 mM lithium bromide was used as the eluent. The weight-average molecular weight of polyamino acid derivative 1, which will be described later, was also measured by the same method.

[0143] Synthesis of Polyamino Acid Derivative 1: 10.0 g of PSI and 95.3 g of dimethylformamide (DMF) were placed in a reaction vessel and heated to 60°C for complete dissolution. After the temperature was lowered to 40°C, a mixture of 0.229 g (1.5 mol % relative to 1 succinimide unit) of 1,2-bis(2-aminoethoxy)ethane (AEE) as a crosslinker and 2.06 g of DMF was added and allowed to react for 7 hours. Next, 10.3 g (54 mol % relative to 1 succinimide unit) of Farmin 20D (n-dodecylamine) was added as amine A and allowed to react for 30 minutes. Furthermore, 3.45 g (44.5 mol % relative to 1 succinimide unit) of 3-amino-1-propanol was added as amine B and allowed to react for 7 hours while maintaining the temperature in the reaction vessel at 60°C. The reaction vessel was then cooled to room temperature and allowed to stand overnight. The reaction mixture was then poured into 1,200 mL of ethyl acetate with stirring to precipitate the reaction product, and the resulting solid was collected by filtration. The resulting mixture was then washed in 600 mL of ethyl acetate with stirring, and the resulting solid was collected by filtration. The collected solid was dried at 60° C. under reduced pressure for 12 hours to obtain 22.0 g of polyamino acid derivative 1 having a weight-average molecular weight of 145,000.

[0144] <Synthesis of Polyamino Acid Derivative 2> Based on Example 1, the reaction conditions were appropriately changed to obtain polyamino acid derivative 2 having a weight-average molecular weight of 250,000.

[0145] <Calculation of composition ratio and hydroxyl value of polyamino acid derivative 1 or 2> First, １ The composition ratio (molar ratio) of polyamino acid derivative 1 or 2 was calculated using HNMR. １ HNMR measurement conditions: 0.1 g of polyamino acid derivative 1 or 2 was dissolved in 0.6 mL of deuterated dimethyl sulfoxide to prepare a measurement sample, and measurement was performed using a JNM-ECZ400S (manufactured by JEOL Ltd.) under the following conditions: Observation frequency: 400 MHz, Chemical shift reference: TMS (tetramethylsilane) (0 ppm), Pulse delay: 6.8 seconds, Number of scans: 16, Pulse width: 45° (3.2 μs), Measurement temperature: 60°C.

[0146] The composition ratio (mol %) of polyamino acid derivative 1 or 2 was calculated using the obtained NMR spectrum according to the following formulas: Ratio of the mol % of monomer unit A-U to the mol % of monomer unit B-U (A-U) / (B-U)=(peak integral value of methyl group of amine A / 3) / (peak integral value of methylene group of amine B / 2) Ratio of the mol % of the sum of monomer unit A-U and monomer unit B-U to the mol % of monomer unit C-U [(A-U)+(B-U)] / (C-U)=[(peak integral value of methyl group of amine A / 3)+(peak integral value of methylene group of amine B / 2)] / (peak integral value of methine group of succinimide)

[0147] Next, the mole percentages of the monomer units A-U and B-U were calculated from the following formulas, and the hydroxyl value was calculated based on the calculated mole percentages: mole percentage of monomer units A-U = (total moles of amine A added during synthesis / total moles of PSI added during synthesis) × 100 mole percentage of monomer units B-U = (total moles of amine B added during synthesis / total moles of PSI added during synthesis) × 100 hydroxyl value = (mol % of B-U / 100) × 56.11 × 1000 / [97 + molecular weight of crosslinker × (mol % of crosslinker / 100) + molecular weight of amine A × (mol % of A-U / 100) + molecular weight of amine B × (mol % of B-U / 100)] In the above formulas, "mol % of crosslinker" refers to the ratio (mol %) of the total moles of crosslinker added during synthesis to the total moles of PSI added during synthesis. Furthermore, the "total number of moles of PSI added during synthesis" in the above formula refers to the value obtained by dividing the weight of PSI added during synthesis by the molecular weight of the repeating unit of PSI.

[0148] The (A-U) / (B-U) ratio of polyamino acid derivative 1 calculated by the above method was 53 / 37, and [(A-U)+(B-U)] / (C-U) was 90 / 7. The hydroxyl value of polyamino acid derivative 1 was 107 mgKOH / g. The (A-U) / (B-U) ratio of polyamino acid derivative 2 was 51 / 49, and [(A-U)+(B-U)] / (C-U) was 95 / 5. The hydroxyl value of polyamino acid derivative 2 was 115 mgKOH / g.

[0149] <Calculation of the amount of crosslinking of polyamino acid derivative 1> The amount of crosslinking (mol %) of polyamino acid derivative 1 was calculated by (total number of moles of crosslinking agent added during synthesis / total number of moles of PSI added during synthesis) × 100. The amount of crosslinking of polyamino acid derivative 1 was 1.5 mol %, and the amount of crosslinking of polyamino acid derivative 2 was 1.15%.

[0150] [Examples 1 to 15, Comparative Examples 1 to 8] Using the synthesized polyamino acid derivative 1 or 2, each raw material was mixed according to the formulation (wt%) shown in Tables 1 to 4, and then the mixture was stirred at 60°C for 2 hours to prepare the compositions of Examples 1 to 15 and Comparative Examples 1 to 8.

[0151]

[0152]

[0153]

[0154]

[0155] The raw materials used in the table are as follows: Xanthan gum: KELTROL CG, manufactured by cpkelco Co., Ltd. 1,3-butanediol: 98% purity, manufactured by Kanto Chemical Co., Ltd. Glycerin: 99.5% purity, manufactured by Kanto Chemical Co., Ltd. Dipropylene glycol: 97% purity, manufactured by Kanto Chemical Co., Ltd. Methanol: 99.8% purity, manufactured by Kanto Chemical Co., Ltd.

[0156] (Evaluation Method) <Viscosity Evaluation> The shear viscosity of each composition in the Examples and Comparative Examples was measured using the following procedure. In Examples 1 to 11 and Comparative Examples 1 to 6, a rotational rheometer (R / Splus manufactured by Brookfield) was used, with a Measuring System C25-2, a Con Truncation of 0.046 mm, and a measurement temperature of 25°C. The shear viscosity was measured at a shear rate of 15 / s, after which the shear rate was increased from 1 / s to 1000 / s. The shear viscosity was measured at a shear rate of 15 / s. The results are shown in Tables 1 and 2. In Examples 12 to 15 and Comparative Examples 7 and 8, the shear viscosity was measured in the same manner as in Examples 1 to 11 and Comparative Examples 1 to 6, except that the shear viscosity was measured at a shear rate of 5 / s. The results are shown in Tables 3 and 4. For Comparative Examples 1, 3 to 5, and 7, which had shear viscosities of less than 100 mPa·s, the evaluation of the feel described below was not carried out.

[0157] <Evaluation of texture> Ten expert evaluation panelists applied each composition of the Examples and Comparative Examples directly to the inner part of the forearm and evaluated the texture at the beginning of application and immediately after application according to the following criteria, with the criteria selected by the largest number of panelists being the evaluation result. The results are shown in Tables 1 and 2. (1) Texture at the beginning of application Y: Refreshing and moist, not sticky N: Sticky (2) Texture immediately after application A: Smooth and moist B: Smooth and slightly moist C: Squeaky

Claims

1. A composition comprising a compound (a) and a compound (b), wherein the compound (a) comprises α- or β-type polyaspartic acid monomer units A-U represented by the following general formula (1) and α- or β-type polyaspartic acid monomer units B-U represented by the following general formula (2), the ratio (A-U) / (B-U) of the molar percentage of the monomer units A-U to the molar percentage of the monomer units B-U in the compound (a) is 40 / 60 to 60 / 40, and the compound (b) is a polyhydric alcohol. (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms. (In the formula, R ２ represents a group containing a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom.

2. The composition according to claim 1, wherein the compound (a) further contains succinimide monomer units C-U represented by the following general formula (3), and the ratio of the mole percentage of the total of the monomer units A-U and B-U to the mole percentage of the monomer units C-U in the compound (a), [(A-U)+(B-U)] / (C-U), is 80 / 20 to 99 / 1.

3. The composition according to claim 1, wherein the compound (a) further contains an α- or β-type polyaspartic acid monomer unit Crosslink-U represented by the following general formula (4): (In the formula, the wavy lines indicate crosslinking sites.) 4. The composition according to claim 2, wherein the compound (a) further contains an α- or β-type polyaspartic acid monomer unit Crosslink-U represented by the following general formula (4): (In the formula, the wavy lines indicate crosslinking sites.) 5. The composition according to claim 1, wherein the compound (a) has a hydroxyl value of 80 mg KOH / g to 170 mg KOH / g.

6. The composition according to claim 3, wherein the amount of crosslinking of the compound (a) is 0.1 mol % to 2.0 mol %.

7. The composition according to claim 1, wherein the weight ratio of said compound (b) to said compound (a) in the composition is 0.1 to 35.

0.

8. The composition according to claim 1, wherein the content of said compound (a) in the composition is 0.1% by weight to 20.0% by weight based on the total weight of the composition.

9. The composition according to claim 1, wherein the content of said compound (b) in the composition is 0.1% by weight to 35.0% by weight based on the total weight of the composition.

10. The composition according to any one of claims 1 to 9, which is an external preparation for the skin.

11. A viscosity enhancing composition containing a compound (a) having a polyhydric alcohol as an active ingredient, the compound (a) comprising α- or β-type polyaspartic acid monomer units A-U represented by the following general formula (1) and α- or β-type polyaspartic acid monomer units B-U represented by the following general formula (2), wherein the ratio (A-U) / (B-U) of the molar percentage of the monomer units A-U to the molar percentage of the monomer units B-U in the compound (a) is 40 / 60 to 60 / 40. (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms. (In the formula, R ２ represents a group containing a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom.

12. A composition for enhancing viscosity containing a polyhydric alcohol, the composition comprising compound (a) as an active ingredient, wherein the compound (a) comprises α- or β-type polyaspartic acid monomer units A-U represented by the following general formula (1) and α- or β-type polyaspartic acid monomer units B-U represented by the following general formula (2), and the ratio (A-U) / (B-U) of the molar percentage of the monomer units A-U to the molar percentage of the monomer units B-U in the compound (a) is 40 / 60 to 60 / 40. (In the formula, R １ represents a group containing a hydrocarbon group having 3 to 22 carbon atoms. (In the formula, R ２ represents a group containing a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom.

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