JPH10251128A - Resin for hair-dressing, hair-treating agent composition, and perfumery and cosmetic composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition having excellent hair-dressing characteristics in use and capable of dressing the hair to get natural feeling free from stickiness by using a polyaspartic acid derivative. SOLUTION: The objective composition is produced by including a polymer (a polyaspartic acid derivative) containing 30-100mol% of the recurring structural units expressed by formula I and/or formula II (R<1> and R<2> are each H or a 3-11C hydrocarbon group) in the molecule and 0-70mol% of a succinimide recurring unit expressed by formula III in the molecule and having a number-average total recurring units in the molecule of 10-5,000.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hair styling resin, a hair cosmetic composition, and a cosmetic composition, which are non-sticky to hair, have excellent set retention properties, and give the hair a rough and natural feeling without discomfort. .

[0002]

[Prior art]

[Technical Background] Although a polyamino acid is a synthetic polymer, it has been studied for a long time as a biopolymer model due to its chemical structure. In addition to its use as a substitute material for general-purpose natural proteins such as natural leather and silk, research on its use for artificial skin, enzyme-immobilized carriers, piezoelectric elements, cosmetics, pharmaceuticals, etc. has been conducted (“Polyamino acid- Applications and Perspectives— "Kodansha" (1974). Japanese Patent Publication No. 48-20638 discloses a technique using a polyaspartic acid derivative as a plasma substitute. Japanese Patent Application Laid-Open No. 3-48628 discloses a technique.
A technique is disclosed in which a polyaspartic acid derivative obtained by opening a ring of polysuccinimide with various amines is applied to a pharmaceutical or food coating. Furthermore, research and development have been advanced on a technique for applying a water-soluble polyamino acid to the field of cosmetics. JP-A-59-209635 discloses that when a moisturizer having a polyglutamate is used as a cosmetic moisturizer, it has an effect of imparting appropriate moisture and smoothness to the skin and preventing skin roughness. It is disclosed. JP-A-7-277916 discloses that a cosmetic product having a moist and smooth feeling of use can be obtained by blending polyaspartic acid with an amino acid, pyrrolidone carboxylic acid and glycine betaine. However, this cosmetic has insufficient affinity for the skin and hair, has a sticky feeling when used, and has a problem that it is soluble only in water.

JP-A-63-35698 discloses a surfactant composition containing at least one skin irritation inhibitor selected from polyglutamic acid and salts thereof and polyaspartic acid and salts thereof. . U.S. Pat. No. 3,846,380 discloses that a polyaspartic acid derivative having a hydrophobic group and a hydrophilic group in a side chain is used as a surfactant. Also, US Pat. No. 4,363,797 discloses that polyaspartic acid derivatives having a thiol group include shampoos, lotions,
It is disclosed that it is suitable for dyes and baths, and is used in hair cosmetics in combination with a polymer of a poly-β-alanine substrate. JP-A-6-24872 discloses that a hair treatment composition comprising a water-soluble polyamino acid derivative having a thiol group and / or a disulfide group is useful for shampoo additives, hair creams, hair lotions, hair brushing agents and the like. It is disclosed that it is suitable for. However, these polyamino acids do not have a hair setting property, and furthermore have good workability in preparing a hair treatment composition and a cosmetic composition (often used in cosmetics). Is not sufficiently soluble. Thus, it has excellent hair styling properties (especially excellent holding power in a high humidity state) at the time of use, has no sticky hair, and has not been able to obtain a polyamino acid soluble in ethanol.

[0004]

DISCLOSURE OF THE INVENTION The present invention relates to a hair styling resin which has excellent hair styling properties during use (especially excellent set holding power in a high humidity state), and which is not sticky and dissolves in ethanol. The present invention relates to a treatment agent and a cosmetic composition.

[0005]

The present invention provides the following [1].
To [8]. [1] Formula (1) [Formula 4] and Formula (2) [Formula 5]

[0006]

Embedded image

[0007]

Embedded image (In the general formulas (1) and (2), R ¹ and R ² each independently represent a hydrogen atom or a saturated or unsaturated hydrocarbon group having 3 to 11 carbon atoms. Show,
And R ¹ and R ² may combine to form a cyclic structure containing a nitrogen atom). At least one type of repeating unit selected from the group consisting of repeating structural units represented by % To 100 mol%, and represented by the general formula (3):

[0008]

Embedded image A hair styling polymer wherein the number average of all repeating units in the molecule is from 10 to 5,000, further comprising 0 to 70 mol% of a repeating structural unit of succinimide in the molecule.

[2] At least one type of repeating unit selected from the group consisting of repeating structural units represented by the general formulas (1) [4] and [2] [30] Having a molar ratio of not less than 99 mol% and not more than
The succinimide represented by the formula [6] further contains 1 to 70 mol% of a repeating structural unit in the molecule, and the number average of all the repeating units in the molecule is 10 to 500.
A hair styling polymer which is 0;

[3] The description of [1], wherein R ^{1 in the} general formulas (1) [formula 4] and (2) [formula 5] is a saturated or unsaturated hydrocarbon group having 4 to 11 carbon atoms. Hair styling polymer.

[4] In the general formula (1) [formula 4] and the general formula (2) [formula 5], R ¹ has a carbon number of 4, 6, 8, ¹
The polymer for hairdressing according to [1], which is 1 saturated or unsaturated hydrocarbon group.

[5] In the general formula (1) [formula 4] and the general formula (2) [formula 5], R ¹ has 4 to 8, 11 carbon atoms.
And at least one type of repeating structure selected from the group consisting of repeating structural units represented by the general formula (1) [Formula 4] and the general formula (2) [Formula 5] The hair styling polymer according to [1], which has a unit in a molecule of not less than 60 mol% and not more than 90 mol%.

[6] In the general formula (1) [formula 4] and the general formula (2) [formula 5], R ¹ is a saturated or unsaturated hydrocarbon group having 4, 6, or 8 carbon atoms; (1) 60 mol% or more and 90 mol% or less in the molecule of at least one kind of repeating structural unit selected from the group consisting of the repeating structural units represented by [Formula 4] and the general formula (2) [Formula 5]. The hair styling polymer according to [1].

[7] A hairdressing cosmetic composition comprising the hairdressing polymer of [1].

[8] A hair cosmetic composition for hair styling comprising the polymer for hair styling of [1].

[0016]

BEST MODE FOR CARRYING OUT THE INVENTION

[Polymer (polyaspartic acid derivative)] The polymer of the present invention has the general formula (1) [formula 4] and the general formula (2) [formula 5]
At least one kind of repeating structural unit selected from the group consisting of repeating structural units represented by the following formula: This repeating structural unit is, for example, a repeating structural unit of a succinimide represented by the general formula (3) [formula 6] obtained from a condensation reaction from aspartic acid or a salt thereof (in the following description, polyamber Acid imide) can be obtained by further chemical modification. That is, the polymer of the present invention is not limited to a production method, but is typically a polyaspartic acid derivative. In the following description, the polymer of the present invention will be described as "polyaspartic acid derivative". In the claims and the entire description of the specification, the “hydrocarbon group” is not only a linear group, but also a branched group.
It also includes a cyclic group, and further includes a hydrocarbon group in which an atom other than C or H such as N, O, S or the like is contained in an atomic group.
Specifically, for example, those having a substituent such as a carboxyl group, an amino group, a hydroxyl group, and an ester group are collectively referred to as a “hydrocarbon group”.

Formula (1) [Formula 4] or Formula (2)
The substituents and the like in [Formula 5] are as follows.

R ¹ and R ^{2 each} represent a hydrogen atom or a saturated or unsaturated hydrocarbon group having 3 to 11 carbon atoms, and R ¹ and R ² combine to form a cyclic structure containing a nitrogen atom. Is also good. Specific examples of R ¹ and R ² include, for example, hydrogen,
Methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, ethylhexyl, nonyl, alkyl groups such as decyl, cyclobutyl, cyclopentyl,
Cycloalkyl groups such as cyclohexyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl,
A hydroxyalkyl group such as hydroxyoctyl; an alkenyl group such as propenyl, butenyl, pentenyl, hexanyl, heptenyl, octenyl and the like;
Other specific examples include azaalkyl and azaalkenyl groups such as azapropyl, azatetramethyl, azapentyl and azahexyl; oxaalkyl groups such as oxapropyl, oxatetramethyl, oxapentyl, oxahexyl, oxaoctyl and ethylhexyloxypropyl And oxaalkenyl groups; thioalkyl groups and thioalkenyl groups such as thiopropyl, thiotetramethyl, thiopentyl, thiohexyl and thiooctyl; and the like. Among them, R ¹ and R ² may be the same, but in consideration of solubility in ethanol, the hydrocarbon group is more preferably a branched hydrocarbon group than a linear hydrocarbon group. Also, in consideration of excellent hair styling set holding power under high humidity conditions, hydrogen atom, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl, n-octyl, ethylhexyl, ethylhexoxyoxypropyl are more preferable. Particularly, a hydrogen atom, n-butyl, isobutyl, n-hexyl, ethylhexyl, and ethylhexoxypropyl are most preferred. Further, it is preferable that R ¹ and R ² are not hydrogen at the same time.

When R ¹ and R ² combine to form a cyclic structure containing a nitrogen atom, that is, when R ¹ and R ² form a cyclic structure containing a nitrogen atom to which they are individually bonded, the above-listed examples are given. It is preferable to form a cyclic structure obtained by combining the groups. When forming a cyclic structure, it may contain a hetero atom other than the nitrogen atom. What forms this cyclic structure is preferably a piperazine ring, a piperidine ring or a morpholine ring, and more preferably a morpholine ring.

The ratio of the α-type repeating structural unit or the β-type repeating structural unit in the molecule of the polyaspartic acid derivative of the present invention is not particularly limited. One unit may be present alone, or both units may be mixed. May be. In the polyaspartic acid derivative of the present invention, the compound represented by the general formula (1)
And the proportion of at least one type of repeating structural unit (hereinafter referred to as a single-chain derivative unit) selected from the group consisting of repeating structural units represented by the general formula (2) No, since hair holding set holding power is not good, 30 mol% or more and 100 mol%
It is as follows. Taking into account easy solubility in ethanol and excellent holding power for hair setting under high humidity conditions, the content of the single-chain derivative unit is particularly preferably from 60 mol% to 90 mol%.

In the polyaspartic acid derivative of the present invention, a polysuccinimide repeating structural unit represented by the general formula (3) [formula 6] (hereinafter simply referred to as polysuccinimide unit) is simultaneously contained in the molecule. When it is contained, it has an excellent effect in that the hair is not sticky under high humidity conditions. In consideration of not impairing the solubility in ethanol, the proportion of the polysuccinimide unit is 0 mol% or more and 7 mol% or more.
0 mol% or less. Further, considering that the flaking (exfoliation state) is good, 0 mol% or more and 40 mol% or more.
Mole% or less is more preferable.

In the polyaspartic acid derivative of the present invention, not only the polysuccinimide unit but also a compound represented by the general formula (1) [4] or (2) [5] A polyaspartic acid derivative unit (hereinafter, referred to as a long-chain derivative unit) which is a long-chain saturated / unsaturated hydrocarbon group having a length of from 20 to 20 can be simultaneously contained in the molecule. In this case, considering that it is preferable to substantially not impair the solubility in ethanol and the effect of holding the hair styling set, the long-chain derivative unit is 0 mol% or more and 30 mol% or less, and polysuccinic acid is used. The imide unit is 0
It is preferably at least 40 mol% and not more than 40 mol%. Further, the number of carbon atoms of the long-chain saturated or unsaturated hydrocarbon group in the long-chain derivative unit is more preferably a saturated or unsaturated hydrocarbon group having 12 or 18 carbon atoms.

The arrangement of the repeating structural units constituting the polyaspartic acid derivative of the present invention is not particularly limited. When it is a copolymer, any of a random copolymer, an alternating copolymer, a block copolymer, and a graft copolymer may be used. The polymer or polymer may be any of linear, macrocyclic, branched, star-shaped, and three-dimensionally stitched. The “polyaspartic acid” contains a polymer obtained by peptide condensation of amino acids.

[0024] The molecular weight of the polyamino acid derivative according to the present invention is not particularly limited as long as the desired action and effect are substantially exhibited. However, the average molecular weight is desirably about 5000 to 5,000,000 in terms of weight average molecular weight in terms of weight average molecular weight by gel permeation chromatography (hereinafter, referred to as GPC) using, for example, a chloroform solvent system.
It is more preferably about 0 to 4,000,000 or less, more preferably about 8000 to 3.5,000,000 or less, most preferably about 10,000 to 2,000,000 or less. This average molecular weight is calculated as a specific value (desirably 5000, preferably 7000, more preferably 8
000, and most preferably 10,000) or more provides more excellent effects in terms of improving the hair styling set holding power of the hair treatment composition, improving the usability, and the like. On the other hand, the average molecular weight is set to a specific value (desirably 5,000,000, preferably 4,000,000,
More preferably 3.5 million or less, and most preferably 2 million or less, more excellent effects are exhibited in terms of improvement in solubility in ethanol and improvement in handleability due to a decrease in solution viscosity. The polymerization degree of all repeating units in the polyaspartic acid derivative of the present invention is preferably from 10 to 5,000. The degree of polymerization of all the repeating units of the polyaspartic acid derivative is determined by the raw material polysuccinimide. [Polysuccinimide] The polysuccinimide used in the present invention is represented by the general formula (4):

[0025]

Embedded image This polysuccinimide can be produced by a known method. For example,
J. Amer. Chem. Soc, 80 , 3361 (1
958) discloses a method in which aspartic acid is used as a raw material and heat-condensed at 200 ° C. for 2 to 3 hours. Japanese Patent Publication No. 48-20638 discloses a method of obtaining a high molecular weight polysuccinimide by performing a reaction in the form of a thin film using a rotary evaporator using 85% phosphoric acid as a catalyst. U.S. Pat. No. 5,057,597 includes:
As a method for industrially obtaining polysuccinimide, a method of heat-condensing polyaspartic acid with a fluidized bed is disclosed. Further, when a higher molecular weight polysuccinimide is required, the polysuccinimide obtained by the above method can be treated with a condensing agent such as dicyclohexylcarbodiimide.

The molecular weight of the polysuccinimide used in the present invention is not particularly limited as long as a product having desired properties is substantially obtained, but the number average n of its repeating units is from 10 to 5,000. Is preferred.
From the viewpoint of molecular weight, the weight average molecular weight by GPC is 5
It is preferably from 000 to 500,000, preferably from 7000 to 400,000, more preferably from 9000 to 300,000, particularly preferably from 10,000 to 200,000. This number average molecular weight is converted to a specific value (desirably 5000, preferably 700
Setting the molecular weight to 0, more preferably 9000, particularly preferably 10,000) or more leads to an increase in the molecular weight of the resulting polyaspartic acid derivative, and exhibits more excellent effects in the various points described above. On the other hand, the average molecular weight is set to a specific value (desirably 500,000, preferably 400,000, more preferably 300,000,
When the content is particularly preferably 200,000 or less, more excellent effects are exhibited in terms of improvement in solubility in ethanol, reduction in viscosity, and the like.

The concepts of the terms “cosmetics”, “cosmetics”, and “hair cosmetics” used in the claims and specification of the present application include, for example, “The 26th New Employee Cosmetic Technical Seminar Textbook” (Co-organized by Tokyo Cosmetic Industry Association and Tokyo Cosmetic Engineers Association, sponsored by Japan Cosmetic Industry Association, June 1994
Mon, Asahi Seimei Hall) Pages 34 and 35, “Tables—Types and Items of Cosmetics” and “Cosmetics” described on page 64 of the same text. Contains quasi-drugs. All of the descriptions are made a part of the disclosure of the specification of the present application by explicitly citing the cited documents and the cited ranges, and by referring to the explicitly cited ranges, the matters or disclosures described in the application specification of the present invention are described. Thus, matters or disclosures that can be directly and uniquely derived by those skilled in the art.

The terms “cosmetics” and “cosmetics” used in the claims and specification of the present application include, for example, emulsions, emulsions, creams, cleansing creams, towels, lipsticks, lotions, lotions and the like. , Nesh tissue, manicure, pedicure, moisturizer, pack,
It also contains mousses, shaving creams, after shaving lotions, deodorants, deodorants and the like.

The concept of the term "hair treatment agent" used in the claims and specification of the present application is mutually equivalent to "hair cosmetics" and "hair cosmetics", for example, shampoo, dandruff shampoo , Rinse / conditioner, hair treatment, hair tonic, hair cream, hair oil, split coat, brushing agent, treatment foam, blow styling agent, styling foam, styling gel, hair spray,
It also contains hair liquids, pomades, tics, temporary hair dyes, semi-permanent hair dyes, permanent hair dyes, hair bleach, permanent wave agents, hair growth and hair growth agents, and the like. The cosmetic composition and the hair treatment composition according to the present invention can be produced by mixing and stirring with desired components by a known or publicly used ordinary method. Specific examples of the cosmetic composition and the hair treatment composition according to the present invention include, for example, an emulsion, a hair mousse, a hair gel, a hair spray, a shampoo, a rinse, a hair treatment, and a whitening agent (having its function, Hair, shampoo, rinse, hair treatment, etc.).
The third component other than the polyamino acid derivative (including, for example, an additive component, an emulsifier component, a compounding component, etc.) in the cosmetic composition and the hair treatment composition according to the present invention can exhibit desired effects. There is no particular limitation. Specific examples of the third component in the cosmetic composition and the hair treatment composition according to the present invention include, for example, alcohols, neutralizing agents, p
H adjusters, fragrances, stabilizers, surfactants, emulsifiers, colorants, pigments, UV shielding ceramic particles, thickeners, extenders, humectants, bactericides, bacteriostats, preservatives, preservatives, etc. No. The addition amount of the third component in the cosmetic composition and the hair treatment composition according to the present invention is appropriately selected within a range in which the undesirable effect of the third component is not exhibited.

[0030]

EXAMPLES The present invention will be described below in detail with reference to experimental examples and comparative examples. The descriptions of synthesis examples, aspects, examples, and the like in the specification of the present application are descriptions for assisting understanding of the contents of the present invention, and the descriptions are grounds for interpreting the technical scope of the present invention narrowly. It is not the nature of becoming.

[Evaluation Method] The evaluation methods employed in the examples and comparative examples are shown below. (1) Evaluation of Weight Average Molecular Weight of Raw Material Polysuccinimide The weight average molecular weight (hereinafter referred to as Mw) of raw material polysuccinimide is determined by gel permeation chromatography (GPC). The evaluation was performed under the following conditions using polystyrene as a standard. DMF-based GPC device: JASCO 880-PU Detector: Shodex RID-300 Column: Shodex KD-804 + KD-80M Solvent: 0.01M LiBr / DMF Concentration: 0.5 wt% Injection volume: 20 μl Flow rate: 1.0 ml / min

(2) Evaluation of Weight Average Molecular Weight of Sodium Polyspartate and Polyaspartate Derivatives Mw of polyamino acid derivatives was evaluated by GPC under the following conditions. Water-based GPC used polyethylene oxide as a standard substance, and chloroform-based GPC used polystyrene as a standard substance. Water-based GPC device: JASCO 880-PU Detector: JASCO 830-RI Column: Shodex OHpak B-804 Solvent: 0.1 M KCl / water: methanol = 8: 2
Mixed solvent concentration: 0.5 wt% Injection volume: 20 μl Flow rate: 0.4 ml / min

Chloroform-based GPC device, detector: Shodex GPC System-
11 Column: Shodex K-805L Solvent: chloroform Concentration: 0.5 wt% Injection volume: 20 μl Flow rate: 1.0 ml / min

(3) Amine reaction rate (addition rate of amine to polysuccinimide) Nuclear magnetic resonance spectrometer (Model FX-, manufactured by JEOL Ltd.)
90 and EX-400), using deuterated dimethyl sulfoxide (d-DMSO), or deuterated chloroform (CDCl ₃ ), deuterated methanol (CD ₃ OD) or deuterated chloroform / deuterated methanol A sample is dissolved in a mixed solvent or heavy water (concentration: 3 wt%), and 1H-NMR spectrum (90 MHz) at room temperature, 1H-NM
The R spectrum (400 MHz) and the 13C-NMR spectrum (100 MHz) were measured, and the actual amine conversion was calculated.

(4) Solubility in Ethanol The solubility of the polymer in ethanol was evaluated at the concentration of 10 wt% as follows. ；: Dissolved, Δ: dissolved after heating, ×: not dissolved.

(5) Curl Retention Test Straight hair having a length of 28 cm was washed with a 0.25% by weight aqueous solution of sodium lauryl sulfate, dried and bundled in 3 g portions. The hair was immersed in a 3% by weight polymer solution (water: ethanol = 7: 3) for 1 minute, uniformly applied, and then strongly rubbed with a finger five times to remove the excess polymer solution. Wrap around lot and fix with rubber band, 50
Dry for 2 hours at ° C. The dried hair is gently removed from the lot, hung in a constant temperature / humidity bath at 30 ° C. and 90% relative humidity, the curl length after 5 hours is measured, and the curl retention rate is calculated by the following equation [Equation 1]. %) Was calculated.

[0037]

[Formula 1] Curl retention rate (%) = [(L−L _n )
/ (L-L ₀ )] × 100 where L: length of original straight hair (cm), L ₀ :
Length of curl at 0 hour (cm), L _n : length of curl after n hours (cm).

(6) Stickiness The curly hair after the evaluation of curl retention was evaluated for the stickiness of the hair when touched as follows. ◎: Not sticky at all, ○: Not sticky, Δ; Slightly sticky, ×: Sticky (7) Flaking The amount of resin that fell off when combing curled hair created in the same manner as in the evaluation of curl retention was determined as follows. Was evaluated as follows. ：: almost no dropout, Δ: hardly dropout, ×: many dropouts.

(8) Texture The touch when the curly hair prepared in the same manner as the curl retention evaluation was touched by hand was evaluated as follows. ：: Soft and comfortable to touch, ゴ: Slightly sticky or sticky, ×: Strong feeling of sticky or sticky.

(9) Overall Evaluation The evaluation results of (4) to (8) were comprehensively evaluated as follows. A: Curl retention is 90% or more, ethanol solubility, flaking, and texture are all ○, and stickiness is ◎ B: Curl retention is 75% or more, and ethanol solubility, stickiness, flaking, and texture are all C: Curl retention is 60% or more and less than 75%,
And ethanol solubility is ○, or ethanol solubility is 75% or more even when the curl retention is 75% or more D: less than 60% curl retention F;

Example 1 (1) Reaction A separable flask equipped with a stirrer, heater, thermometer and nitrogen line was used as a reactor, and the reaction system was sufficiently stirred during the reaction. Raw material polysuccinimide (DM
For Mw = 88,000 by F-based GPC, use what was dried well by heating under reduced pressure at 60 ° C., and used 19.42 g of this polysuccinimide (hereinafter referred to as PSI).
(0.2 mol) was dissolved in 80 g of DMF at room temperature.
5.91 g (0.1 mol) of n-propylamine was added dropwise. DMF as a reaction solvent was dried by blowing molecular sieve and dry nitrogen gas, and the reaction was carried out at a water content of 800 ppm or less in the reaction system. After completion of the dropwise addition, the reactor was reacted at room temperature for 24 hours. After the reaction of n-prolamine was completed, the reaction solution was subjected to an isolation operation.

(2) Isolation The above reaction mixture was mixed with 800 ml of a 5: 2 mixed solvent of acetone: hexane, which is a poor solvent for the resulting polyaspartic acid derivative.
The resulting mixture was discharged with stirring to precipitate the resulting polyaspartic acid derivative. This polyaspartic acid derivative suspension was subjected to suction filtration, and the resulting polyaspartic acid derivative was isolated as a filter cake. Further, the operation of dispersing and stirring the filter cake in the above mixed poor solvent and performing suction filtration was repeated several times, whereby the produced polyaspartic acid derivative was sufficiently washed. Thereafter, the resultant was dried with hot air at 60 ° C., and the resulting polyaspartic acid derivative was isolated. 22.8 g (90% yield) of the isolated polyspartic acid derivative was obtained and used for evaluation.

[Preparations and Evaluations of Examples 2 to 26] (1) Reaction and Isolation Examples 2 to 26 The same apparatus and operation as in (1) and (2) of Example 1 were performed. PS used in the reactions of Examples 2 to
The molecular weight of I, the type of amine reacted, and the charge ratio of these amines to PSI are as shown in Table 1. Evaluation tests were performed on the polyaspartic acid derivatives obtained in Examples 2 to 4 in the same manner as in the polyaspartic acid derivative obtained in Example 1.

Comparative Example 1 (1) The same polysuccinimide as in Example 1 was used for evaluation.

Comparative Example 2 (1) Synthesis and Isolation of Sodium Polyaspartate The same reactor and polysuccinimide as in Example 1 were used. 19.42 g of polysuccinimide (0.2
mol) was suspended in 100 ml of distilled water. 100 ml of a 2N aqueous sodium hydroxide solution was added to this suspension at room temperature,
The reaction system was gradually dropped while paying attention so that the pH of the reaction system was in the range of 9 to 12. After the completion of the dropwise addition, it was subjected to an isolation operation. (2) Isolation of hydrolyzate The above reaction solution was concentrated to about 80 ml, and 800 m was added to ethanol, which is a poor solvent for sodium polyaspartate.
The sodium polyaspartate was allowed to settle out while stirring. This sodium polyaspartate was subjected to suction filtration, and the sodium polyaspartate was isolated as a filter cake. Further, the operation of dispersing and stirring the filter cake in the above poor solvent and performing suction filtration was repeated several times to sufficiently wash the sodium polyaspartate. Thereafter, the resultant was dried with hot air at 60 ° C. to isolate sodium polyaspartate. 24.7 g (yield 90%) of the isolated sodium polyaspartate was obtained and used for evaluation. The weight average molecular weight of the isolated product is determined by the aqueous GP
C was 54,000.

The polyaspartic acid derivative obtained in Comparative Example 2 was subjected to an evaluation test in the same manner as the polyaspartic acid derivative obtained in Example 1. [Comparative Examples 3 to 14] Preparation / Evaluation] (1) Reaction / Isolation In Comparative Examples 3 to 14, the same apparatus and operation as in (1) and (2) of Example 1 were performed. The molecular weights of the PSI used in the reactions of Comparative Examples 3 to 14, the types of the reacted amines, and the charging ratios of the amines to the PSI are as shown in Table-2. The evaluation test was performed on the polyaspartic acid derivatives obtained in Comparative Examples 3 to 14 in the same manner as the polyaspartic acid derivative obtained in Example 1.

[0047]

[Table 1]

[0048]

[Table 2]

[0049]

Industrial Applicability The present invention has excellent hair styling properties (especially excellent set holding power in a high humidity state) at the time of use, and furthermore, a hair styling resin, a hair treating agent and a fragrance which are not sticky and are soluble in ethanol. The present invention relates to a cosmetic composition.

Claims (8)

[Claims] [Claim 1] The general formula (1) [formula 1] and the general formula (2)
[Formula 2] [Formula 1] Embedded image (In the general formula (1) [formula 1] and the general formula (2) [formula 2], R ¹ and R ² each independently represent a hydrogen atom or a saturated or unsaturated hydrocarbon group having 3 to 11 carbon atoms. Show,
And R ¹ and R ² may combine to form a cyclic structure containing a nitrogen atom). At least one type of repeating unit selected from the group consisting of repeating structural units represented by % Or more and 100 mol% or less, and represented by the general formula (3): A hair styling polymer wherein the number average of all repeating units in the molecule is from 10 to 5,000, further comprising 0 to 70 mol% of a repeating structural unit of succinimide in the molecule. 2. The compound represented by the general formula (1) [formula 1] and the general formula (2)
At least one kind of repeating unit selected from the group consisting of repeating structural units represented by [Chemical Formula 2] is represented by 3 in the molecule.
0 mol% or more and 99 mol% or less, and further having 1 mol% or more and 70 mol% or less in the molecule of the repeating structural unit of succinimide represented by the general formula (3) [Formula 3]. A hairdressing polymer having a number average of all repeating units of 10 to 5000. 3. The compound represented by the general formula (1) [formula 1] and the general formula (2)
In the chemical formula 2, R ¹Is saturated or unsaturated having 4 to 11 carbon atoms.
The hairdressing polymerization according to claim 1, which is a saturated hydrocarbon group.
body. 4. The general formula (1) [formula 1] and the general formula (2)
2. The hairdressing polymer according to claim 1, wherein in the chemical formula 2, R ¹ is a saturated or unsaturated hydrocarbon group having 4, 6, 8, or 11 carbon atoms. 5. A compound of the general formula (1) [formula 1] and the general formula (2)
In the chemical formula 2, R ¹ is a saturated or unsaturated hydrocarbon group having 4 to 8 or 11 carbon atoms and represented by the general formulas (1) and (2). 2. The hair styling polymer according to claim 1, wherein the polymer has at least one kind of repeating structural unit selected from the group consisting of repeating structural units in a molecule of 60 mol% or more and 90 mol% or less. 6. A compound of the general formula (1) [formula 1] and the general formula (2)
In Chemical Formula 2, R ¹ is a saturated or unsaturated hydrocarbon group having 4, 6, or 8 carbon atoms, and is represented by General Formulas (1) [1] and (2) [2]. 2. The hair styling polymer according to claim 1, wherein the polymer has at least one kind of repeating structural unit selected from the group consisting of repeating structural units in a molecule of 60 mol% or more and 90 mol% or less. 7. A hair styling cosmetic composition comprising the hair styling polymer of claim 1. 8. A hair styling hair cosmetic composition comprising the hair styling polymer of claim 1.