JP2010138099A - Hairdressing agent composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a hairdressing agent composition that is easily spread to impart a smooth touch to the hair, has excellent setting power and allows redressing. <P>SOLUTION: The hairdressing agent composition includes components (A) and (B). (A) An organopolysiloxane including a poly(N-acylalkyleneimine) segment composed of a recurring unit represented by general formula (1) [wherein R<SP>1</SP>is H, a 1-22C alkyl group, an aralkyl group or an aryl group; and n is 2 or 3] and having a number-average molecular weight of 800-1,600 bonded, via an alkylene group containing a heteroatom, to at least two silicon atoms of an organopolysiloxane segment constituting a main chain having a weight-average molecular weight of 10,000-100,000 with a mass ratio of the organopolysiloxane segment to the poly(N-acylalkyleneimine) segment of 65/35 to 82/18. (B) Poly(methacryloyloxyethyltrimethylammonium chloride) having a weight-average molecular weight of at least 1,000,000. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a hairdressing composition.

  Among hair cosmetics for styling, aerosol-type hair sprays and the like generally fix hair using the fixing force of the hair setting polymer. However, in such hair cosmetics, once the hair is fixed, if the hair style breaks down, the hair cannot be fixed again (hereinafter referred to as “re-styling”), and the finished hair is stiff. There are complaints such as hardness.

  On the other hand, a hair cosmetic containing a general hair set polymer and a thickener and having a certain level of adhesive strength is also known. Such hair cosmetics can be re-haired by adhesive strength, but have a problem that the finished hair is sticky and oily.

  For the purpose of improving the touch after application, a hair cosmetic prepared by blending a specific organopolysiloxane with an organic carboxylic acid and an organic solvent has been proposed (Patent Document 1). As an example, a specific cation is further used as a thickener. Hair cosmetics containing functional polymers are described (Table 2). However, although these hair cosmetics can obtain a smooth feel after application, the hair styling power is still not sufficient.

JP 2007-223931 JP

  Accordingly, an object of the present invention is to provide a hair styling composition that can be easily stretched to the hair, can give a smooth feel, has excellent setting power, and is capable of re-styling.

  The present inventors have found that a hair styling composition that satisfies the above requirements can be obtained by using a specific cationic polymer as a thickener together with a specific organopolysiloxane.

The present invention provides a hair styling composition containing the following components (A) and (B).
(A) At least two silicon atoms of the organopolysiloxane segment constituting the main chain, via an alkylene group containing a hetero atom, the following general formula (1);

[Wherein, R ¹ represents a hydrogen atom, an alkyl group having 1 to 22 carbon atoms, an aralkyl group or an aryl group, and n represents 2 or 3. ]
An organopolysiloxane formed by bonding poly (N-acylalkyleneimine) segments composed of repeating units represented by:
The number average molecular weight of the poly (N-acylalkylenimine) segment is 800-1600,
The mass ratio (a / b) of the organopolysiloxane segment (a) constituting the main chain to the poly (N-acylalkylenimine) segment (b) is 65/35 to 82/18,
The weight average molecular weight of the organopolysiloxane segment constituting the main chain is 10,000 to 100,000,
Organopolysiloxane
(B) Polymethacryloyloxyethyltrimethylammonium chloride having a weight average molecular weight of 1 million or more

  The hairdressing composition of the present invention is easy to stretch on the hair, can give a smooth feel, has excellent setting power, and can be restyled.

[(A): Organopolysiloxane]
In component (A), at least two poly (N-acylalkyleneimine) segments can be bonded to any silicon atom constituting the organopolysiloxane segment via an alkylene group containing a hetero atom. In addition, it is preferably bonded to one or more silicon atoms excluding both ends via the alkylene group, and more preferably bonded to two or more silicon atoms excluding both ends via the alkylene group.

  The alkylene group containing a hetero atom intervening in the bond between an organopolysiloxane segment and poly (N-acylalkyleneimine) has 2 to 20 carbon atoms containing 1 to 3 nitrogen atoms, oxygen atoms and / or sulfur atoms. An alkylene group is mentioned. As a specific example,

The N-acylalkyleneimine unit constituting the poly (N-acylalkylenimine) segment is represented by the general formula (1). In the general formula (1), R ¹ has 1 to 22 carbon atoms. Examples of the alkyl group include linear, branched or cyclic alkyl groups having 1 to 22 carbon atoms, and specifically include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group. Tert-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, octadecyl, nonadecyl, eicosyl, docosyl, etc. The Among these, an alkyl group having 1 to 10 carbon atoms, particularly 1 to 6 carbon atoms is more preferable.

  Examples of the aralkyl group include aralkyl groups having 7 to 15 carbon atoms, and specific examples include a benzyl group, a phenethyl group, a trityl group, a naphthylmethyl group, and an anthracenylmethyl group. Among them, an aralkyl group having 7 to 14 carbon atoms, particularly 7 to 10 carbon atoms is more preferable.

  Examples of the aryl group include an aryl group having 6 to 14 carbon atoms, and specific examples include a phenyl group, a tolyl group, a xylyl group, a naphthyl group, a biphenyl group, an anthryl group, and a phenanthryl group. An aryl group having 6 to 12 carbon atoms, particularly 6 to 9 carbon atoms is more preferable.

Among these, R ^1, particularly preferably an alkyl group having 1 to 6 carbon atoms.

  The mass ratio (a / b) of the organopolysiloxane segment (a) to the poly (N-acylalkyleneimine) segment (b) is 65/35 to 82/18, but is not sticky and has setability and re-setting. From the viewpoint of excellent hair styling properties, it is preferably 68/32 to 80/20, more preferably 70/30 to 79/21, and still more preferably 73/27 to 79/21.

In the present specification, the mass ratio (a / b) is determined by dissolving 5% by mass of the organopolysiloxane of component (A) in deuterated chloroform and analyzing it by nuclear magnetic resonance ( ¹ H-NMR) analysis. The value obtained from the integral ratio of the alkyl group or phenyl group in the segment and the methylene group in the poly (N-acylalkylenimine) segment.

  In addition, the weight average molecular weight (MWg) of the organopolysiloxane segment between adjacent poly (N-acylalkylenimine) segments is preferably 1500 to 3500, and is not sticky, and has excellent setting properties and re-styling properties. Therefore, it is preferably 1600 to 3200, more preferably 1700 to 3000.

In the present specification, “an organopolysiloxane segment between adjacent poly (N-acylalkyleneimine) segments” means an organopolysiloxane of a poly (N-acylalkyleneimine) segment as shown in the following formula (2): A portion surrounded by a broken line between two points from a bonding point to the segment (bonding point A) to a bonding point (bonding point B) of the poly (N-acylalkyleneimine) segment adjacent thereto, A segment composed of an R ² SiO unit, one R ⁶ , and y + 1 R ² ₂ SiO units. The “poly (N-acylalkylenimine) segment” refers to Z bonded to the above R ⁶ .

In the general formula (2), each R ² independently represents an alkyl group having 1 to 22 carbon atoms or a phenyl group, R ⁶ represents an alkylene group containing a hetero atom, and Z represents a poly (N-acylalkyleneimine). Represents a segment, R ⁷ represents a residue of a polymerization initiator, and y represents a positive number.

  MWg is the molecular weight of the portion surrounded by the broken line in the above general formula (2), but is understood as the mass (g / mol) of the organopolysiloxane segment per mole of the poly (N-acylalkylenimine) segment. When the functional group of the modified organopolysiloxane, which is a raw material compound, is 100% substituted with poly (N-acylalkyleneimine), it matches the functional group equivalent (g / mol) of the modified organopolysiloxane.

  The molecular weight (MWox) of the poly (N-acylalkylenimine) segment can be measured by a method of calculating from the molecular weight of N-acylalkyleneimine units and the degree of polymerization, or by a gel permeation chromatography (GPC) measurement method described later. Although it is possible, in the present invention, it refers to the number average molecular weight measured by the GPC measurement method, which is 800 to 1600, preferably 850 to 1500, and more preferably 900 to 1400. Thereby, it can be made non-sticky and more excellent in setting property and re-styling property.

  Further, MWg can be obtained by the following formula using the content (Csi) of the organopolysiloxane segment constituting the main chain.

  The weight average molecular weight (MWsi) of the organopolysiloxane segment constituting the main chain is 10,000 to 100,000, which is preferable from the viewpoint of sufficient film strength, solubility in polar solvents such as water and ease of handling after dissolution. Is from 20,000 to 80,000, more preferably from 30,000 to 60,000. Since MWsi has a common skeleton with the modified organopolysiloxane that is the raw material compound, MWsi is substantially the same as the weight average molecular weight of the modified organopolysiloxane that is the raw material compound. In addition, the weight average molecular weight of the modified organopolysiloxane which is a raw material compound is measured by GPC under the following measurement conditions and is converted to polystyrene.

Column: Super HZ4000 + Super HZ2000 (Tosoh Corporation)
Eluent: 1 mM triethylamine / THF
Flow rate: 0.35mL / min
Column temperature: 40 ° C
Detector: UV
Sample: 50μL

  The weight average molecular weight (MWt) of the component (A) is preferably from 12,000 to 150,000, more preferably from 24,000 to 120,000, and even more preferably from 37,000 to 92,000. Thereby, sufficient film | membrane intensity | strength can be ensured and the solubility with respect to polar solvents, such as water, will become excellent. Moreover, it is not sticky, and both styling properties of setability and re-styling property can be further improved. In the present specification, MWt can be determined from the weight average molecular weight of the modified organopolysiloxane that is a raw material compound and the aforementioned mass ratio (a / b).

  The organopolysiloxane of component (A) is, for example, a terminal obtained by ring-opening polymerization of a modified organopolysiloxane represented by the following general formula (3) and a cyclic imino ether represented by the following general formula (4) It is produced by reacting with a reactive poly (N-acylalkylenimine).

[Wherein R ² has the same meaning as above, and R ³ and R ⁴ each represent the same group as R ² , or

R ⁵ represents a monovalent group represented by the above formula, d represents an integer of 135 to 1350, and e represents an integer of 3 to 57. ]

[Wherein, R ¹ and n are as defined above. ]

  The modified organopolysiloxane preferably has a functional group equivalent of 1700-3500, more preferably 1800-3200, particularly preferably 2000-3000, and a weight average molecular weight of preferably 10,000-100,000, more preferably 20,000-80,000. In particular, it is desirable to use one having a viscosity of 30,000 to 60,000.

  The terminal reactive poly (N-acylalkylenimine) is preferably adjusted to have a molecular weight of 800 to 1600, more preferably 850 to 1500, and still more preferably 900 to 1400.

  A polymerization initiator can be used for the ring-opening polymerization of the cyclic imino ether (4). As the polymerization initiator, a compound having strong electrophilic reactivity, for example, a strong acid such as benzenesulfonic acid alkyl ester, p-toluenesulfonic acid alkyl ester, trifluoromethanesulfonic acid alkyl ester, trifluoroacetic acid alkyl ester, sulfuric acid dialkyl ester, etc. Alkyl esters can be used, and among them, dialkyl sulfate is preferably used. The amount of the polymerization initiator used is usually 1 mol of the polymerization initiator with respect to 2 to 100 mol of the cyclic imino ether (4).

  Examples of the polymerization solvent include acetates such as ethyl acetate and propyl acetate, ethers such as diethyl ether, diisopropyl ether, dioxane and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, halogen solvents such as chloroform and methylene chloride, acetonitrile. , Nitrile solvents such as benzonitrile, aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, etc., among which acetates are preferred Is done. The amount of the solvent used is usually 20 to 2000 parts by mass with respect to 100 parts by mass of the cyclic imino ether (4).

  The polymerization temperature is usually 30 to 170 ° C., preferably 40 to 150 ° C., and the polymerization time is usually 1 to 60 hours, although it is not uniform depending on the polymerization temperature and the like.

  When, for example, 2-substituted-2-oxazoline is used as the cyclic imino ether (4), a poly (N-acylethyleneimine) of n = 2 in the general formula (1) is obtained, and 2-substituted-dihydro When 2-oxazine is used, poly (N-acylpropyleneimine) having n = 3 in the general formula (1) can be obtained.

Examples of a method for connecting poly (N-acylalkylenimine) and the organopolysiloxane segment include the following methods.
1) A method of reacting a terminally reactive poly (N-acylalkyleneimine) obtained by living polymerization of a cyclic imino ether with a modified organopolysiloxane represented by the above general formula (3) 2) A carboxyl group and a hydroxyl group 3) Formation of ester by condensation of carboxyl group and amino group 4) Formation of amide by condensation of carboxyl group and amino group 4) Secondary, tertiary or quaternary of alkyl halide group with primary, secondary or tertiary amino group Formation reaction of ammonium 5) Addition reaction of vinyl group to organopolysiloxane having Si-H group 6) Formation reaction of β-hydroxyamine between epoxy group and amino group

  In particular, the above method 1) is polymerized by using the cyclic imino ether (4) and the polymerization initiator as shown in the following theoretical formula (where MWi is the molecular weight of poly (N-acylalkyleneimine)). It is most effective in that a substantially monodispersed poly (N-acylalkylenimine) having a molecular weight distribution narrower than that of normal radical polymerization can be obtained.

  Examples of the component (A) organopolysiloxane include poly (N-formylethyleneimine) organosiloxane, poly (N-acetylethyleneimine) organosiloxane, and poly (N-propionylethyleneimine) organosiloxane.

  The organopolysiloxane of component (A) can be used alone or in combination of two or more, and the content thereof is 0.1% of the total composition from the viewpoint of hair setability, re-hair styling, and washability by shampooing. -20% by mass, more preferably 3-10% by mass, and even more preferably 4.5-6% by mass.

[(B): polychlorinated methacryloyloxyethyltrimethylammonium chloride]
Component (B), polymethacryloyloxyethyltrimethylammonium chloride, is a cationic polymer described in the 10th edition of the INCI Dictionary (USA, International Cosmetic Ingredient Dictionary and Handbook) under the name Polyquaternium-37. From the viewpoint of imparting an appropriate viscosity to the composition and making it easy to stretch into the hair, the polyquaternium-37 as the component (B) has a weight average molecular weight of 1 million or more, preferably a weight average molecular weight of 100. Those having a weight average molecular weight of 1,200,000 to 5,000,000 are used.

  The content of the component (B) is 0.01 to 2% by mass, more preferably 0.1 to 1% by mass, based on the total composition, from the viewpoint of obtaining a high setting power and re-styling, and obtaining a smooth feel that is easy to stretch on the hair. 0.4-0.7 mass% is especially preferable.

  The value of the mass ratio (A) / (B) of the component (A) to the component (B) is preferably from 3 to 16, more preferably from 5 to 14, more preferably from the viewpoint of obtaining a high setting force and an appropriate viscosity. ~ 12 are preferred.

[Highly polymerized polyethylene glycol]
The hair styling composition of the present invention can further contain highly polymerized polyethylene glycol from the viewpoint of improving the ease of extension to the hair. The highly polymerized polyethylene glycol preferably has a number average molecular weight of 100,000 to 10,000,000, more preferably 1,000,000 to 5,000,000.

  The content of the highly polymerized polyethylene glycol is preferably 0.01 to 1% by mass, more preferably 0.05 to 0.5% by mass, and particularly preferably 0.1 to 0.3% by mass in the total composition from the viewpoint of ease of extension to hair and high setting power.

[Silicones]
Furthermore, the hairdressing composition of the present invention can contain silicones. Examples of such silicones include those shown below.

(1) Dimethylpolysiloxane Examples include those represented by the following general formula.
(CH ₃ ) ₃ SiO — [(CH ₃ ) ₂ SiO] _k —Si (CH ₃ ) ₃
[In formula, k shows the number of 3-20000. ]

(2) Amino-modified silicone Various amino-modified silicones can be used, but in particular, the average molecular weight of about 3000 to 100,000 is Amodimethicone, Aminoethylaminopropyl Dimethicone, or Aminopropyl imethicone. ) In the INCI Dictionary (US, International Cosmetic Ingredient Dictionary and Handbook) 10th edition is preferable. This amino-modified silicone is preferably used as an aqueous emulsion, and commercially available products include SM 8704C (Toray Dow Corning), DC 929 (Dow Corning), KT 1989 (Momentive Performance Materials), etc. Is mentioned. Although it does not specifically limit as N content, 0.01-1 mass% is preferable and 0.05-0.3 mass% is especially preferable.

(3) Other silicones Other than the above, polyether-modified silicone, methylphenylpolysiloxane, fatty acid-modified silicone, alcohol-modified silicone, alkoxy-modified silicone, epoxy-modified silicone, fluorine-modified silicone, cyclic silicone, alkyl-modified silicone, etc. It is done.

  Two or more types of silicones may be used in combination, and the content thereof is preferably 0.01 to 20% by mass, more preferably 0.05 to 12% by mass, and particularly preferably 0.3 to 6% by mass in the total composition.

[Cationic surfactant]
The hair styling composition of the present invention may further contain a cationic surfactant.
Examples of the cationic surfactant include quaternary ammonium salts represented by the following general formula (5).

[In the formula, R ⁸ and R ⁹ each independently represent a hydrogen atom, an alkyl group having 1 to 28 carbon atoms or a benzyl group, and simultaneously a hydrogen atom or a benzyl group; Except when it becomes an alkyl group. An ⁻ represents an anion. ]

Here, one of R ⁸ and R ⁹ is preferably an alkyl group having 16 to 24 carbon atoms, more preferably 22 alkyl groups, particularly a linear alkyl group, and the other is a lower alkyl group having 1 to 3 carbon atoms, particularly A methyl group is preferred. Examples of the anion An ^- include halide ions such as chloride ions and bromide ions; organic anions such as ethyl sulfate ions and methyl carbonate ions. Halide ions, particularly chloride ions are preferred.

  As the cationic surfactant, mono long-chain alkyl quaternary ammonium salts are preferable, and specific examples include cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, aralkyltrimethylammonium chloride, and behenyltrimethylammonium chloride. Stearyl trimethyl ammonium and behenyl trimethyl ammonium chloride are preferable.

〔solvent〕
The hairdressing composition of the present invention preferably further contains ethanol and / or water as a solvent. These contents are preferably from 4 to 98.4% by mass, more preferably from 30 to 98% by mass, particularly from 50 to 95% by mass, from the viewpoint of improving the solubility of the polymer and plasticizer contained in the cosmetic. % Is preferred.

[Other optional ingredients]
In addition to the above-described components, the hair styling composition of the present invention may contain components used in normal hair cosmetics depending on the purpose. Examples of such components include film-forming polymers other than component (A) (eg, carrageenan, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymer), cationic polymers, and thickeners other than component (B). , Surfactants other than cationic surfactants, organic solvents other than ethanol (aromatic alcohol, etc.), oil agents, antidandruff agents, vitamins, bactericides, anti-inflammatory agents, chelating agents, moisturizers (pantenol, etc.), Examples include pH adjusters, colorants such as dyes and pigments, plant extracts, pearling agents, fragrances, ultraviolet absorbers, and antioxidants.

  The hair styling composition of the present invention is preferably used in a pump dispenser.

[Viscosity, dosage form]
The hair styling composition of the present invention preferably has a viscosity so low that it can be used in a pump-type container (pump dispenser). The viscosity is preferably 50 to 20,000 mPa · s, more preferably 100 ˜10,000 mPa · s, particularly 200 to 5,000 mPa · s is preferable. Here, the viscosity is measured with a B-type viscometer TVB-10 (Toki Sangyo Co., Ltd.) under the conditions after rotation at 30 ° C., 30 r / m for 60 seconds. The rotor is No. 2 when the viscosity is 1,000 mPa · s, No. 3 when the viscosity is more than 4,000 mPa · s, and No. 4 is used when the viscosity is higher.

  The form of the hairdressing composition of the present invention can be appropriately selected from liquid, gel, paste, cream and the like.

In the following examples, the content of the organopolysiloxane segment is a value determined from a nuclear magnetic resonance method ( ¹ H-NMR), and the weight average molecular weight of the final product is a calculated value. The molecular weight of poly (N-propionylethyleneimine) is a number average molecular weight determined by gel permeation chromatography (GPC).

Column: K-804L + K-804L manufactured by Showa Denko KK Eluent: 1 mmol / L Pharmin DM20 (manufactured by Kao Corporation) / chloroform Flow rate: 1.0 mL / min
Column temperature: 40 ° C
Detector: RI
Sample amount: 5mg / mL, 100μL
Polystyrene conversion

Synthesis Example 1 Organopolysiloxane A
6.5 g (0.042 mol) of diethyl sulfate and 34.4 g (0.36 mol) of 2-ethyl-2-oxazoline were dissolved in 87 g of dehydrated ethyl acetate and heated under reflux for 8 hours under a nitrogen atmosphere to react with terminal reactive poly (N-propionylethylene). Imine) was synthesized. The number average molecular weight measured by GPC was 1300. A 33% ethyl acetate solution of 100 g of side chain primary aminopropyl-modified polydimethylsiloxane (weight average molecular weight 32000, amine equivalent 2000) was added all at once and heated to reflux for 10 hours. The reaction mixture was concentrated under reduced pressure to obtain an N-propionylethyleneimine-dimethylsiloxane copolymer as a pale yellow rubbery semi-solid (138 g, yield 98%). The final product had an organopolysiloxane segment content of 71 mass% and a weight average molecular weight of 46000. As a result of neutralization titration with hydrochloric acid using methanol as a solvent, it was found that about 22 mol% of amino groups remained.

Synthesis Example 2 Organopolysiloxane B
In the same manner as in Synthesis Example 1, 19.0 g (0.12 mol) of diethyl sulfate and 81.0 g (0.82 mol) of 2-ethyl-2-oxazoline are dissolved in 203.0 g of dehydrated ethyl acetate and heated to reflux for 8 hours in a nitrogen atmosphere. Terminal reactive poly (N-propionylethyleneimine) was synthesized. The number average molecular weight measured by GPC was 1100. A 33% ethyl acetate solution of 300 g of side chain primary aminopropyl-modified polydimethylsiloxane (weight average molecular weight 32000, amine equivalent 2000) was added all at once and heated to reflux for 10 hours. The reaction mixture was concentrated under reduced pressure to obtain an N-propionylethyleneimine-dimethylsiloxane copolymer as a pale yellow rubbery solid (390 g, yield 97%). The content of the silicone segment in the final product was 75% by mass, and the weight average molecular weight was 40000. As a result of neutralization titration with hydrochloric acid using methanol as a solvent, it was found that about 20 mol% of amino groups remained.

Synthesis Example 3 Organopolysiloxane C
In the same manner as in Synthesis Example 1, 6.5 g (0.042 mol) of diethyl sulfate, 20.1 g (0.21 mol) of 2-ethyl-2-oxazoline and 57 g of dehydrated ethyl acetate were added to poly (N-propionylethylene having a number average molecular weight of 900. Imin). Further, 100 g of side chain primary aminopropyl-modified polydimethylsiloxane (weight average molecular weight 36000, amine equivalent 2000) was used to convert the N-propionylethyleneimine-dimethylsiloxane copolymer into a pale yellow syrupy semisolid (124 g, yield 98). %). The final product had an organopolysiloxane segment content of 79% by mass and a weight average molecular weight of 46000. As a result of neutralization titration with hydrochloric acid using methanol as a solvent, it was found that about 21 mol% of amino groups remained.

Synthesis Example 4 Organopolysiloxane D
In the same manner as in Example 1, 0.8 g (0.005 mol) of diethyl sulfate, 12.8 g (0.14 mol) of 2-ethyl-2-oxazoline and 29 g of dehydrated ethyl acetate were added to poly (N-propionylethylene having a number average molecular weight of 2700. Imin). Further, using 100 g of side chain primary aminopropyl-modified polydimethylsiloxane (weight average molecular weight 100000, amine equivalent 20000), N-propionylethyleneimine-dimethylsiloxane copolymer was converted into a pale yellow rubbery solid (111 g, yield 98%). ). The content of the organopolysiloxane segment in the final product was 88% by mass, and the weight average molecular weight was 114,000. As a result of neutralization titration with hydrochloric acid using methanol as a solvent, it was found that no amino group remained.

Synthesis Example 5 Organopolysiloxane E
In the same manner as in Example 1, 3.2 g (0.021 mol) of diethyl sulfate, 92.8 g (0.98 mol) of 2-ethyl-2-oxazoline and 205 g of dehydrated ethyl acetate were added to poly (N-propionylethylene having a number average molecular weight of 5200. Imin). Further, 100 g of side chain primary aminopropyl-modified polydimethylsiloxane (weight average molecular weight 50000, amine equivalent 3800) was used to convert N-propionylethyleneimine-dimethylsiloxane copolymer into a pale yellow rubber-like solid (188 g, yield 96%). ). The content of the organopolysiloxane segment in the final product was 51% by mass, and the weight average molecular weight was 98,000. As a result of neutralization titration with hydrochloric acid using methanol as a solvent, it was found that about 24 mol% of amino groups remained.

Synthesis Example 6 Organopolysiloxane F
In the same manner as in Synthesis Example 1, 0.6 g (0.004 mol) of diethyl sulfate, 3.6 g (0.04 mol) of 2-ethyl-2-oxazoline, and 9 g of dehydrated ethyl acetate were added to poly (N-propionylethylene having a number average molecular weight of 1200. Imin). Further, using 100 g of side chain primary aminopropyl-modified polydimethylsiloxane (weight average molecular weight 100000, amine equivalent 20000), N-propionylethyleneimine-dimethylsiloxane copolymer was converted into a pale yellow rubber-like solid (95 g, yield 95%). ). The content of the organopolysiloxane segment in the final product was 96% by mass, and the weight average molecular weight was 104000. As a result of neutralization titration with hydrochloric acid using methanol as a solvent, it was found that about 30 mol% of amino groups remained.

Examples 1-4 and Comparative Examples 1-4
Hair styling compositions having the formulations shown in Table 1 were prepared by conventional methods and evaluated for “setting power”, “re-hair styling”, “smooth feel of hair”, and “easy extension to hair”.

  The evaluation was performed by 10 expert panelists according to the following methods and standards, and the average value of the evaluation points is shown in each table.

(Production of evaluation hair bundle)
A hair bundle of 20 cm length and 10 g (curl cycle: about 5 cm, Caucasian hair, KERLING) was treated with a general plain shampoo and plain rinse once, and then lightly wiped with a towel and air dried.

(Evaluation of ease of extension to hair)
To the evaluation hair bundle in a suspended state, 0.5 g of each hairdressing composition having the composition shown in Table 1 was once taken in the hand and evenly applied. About the hair | bristle bundle after application | coating, sensory evaluation was performed in the following five steps by the specialized panelist (absolute evaluation).

(Evaluation of set power)
The wave bundle was prepared by gently lifting the hair bundle used in the evaluation of stickiness while lifting it from below. About the hair bundle after a process, visual evaluation was performed in the following five steps by the specialized panelist (absolute evaluation).

(Evaluation of hair styling)
The hair bundle used in the evaluation of the set force was combed 10 times with a ring comb (Uehara Cell Co., New Delrin Comb No. 1), and the wave was prepared by gently lifting it from the bottom and holding it again. About the hair bundle after a process, visual evaluation was performed in the following five steps by the specialized panelist (absolute evaluation).

(Evaluation of smooth feel of hair)
The hair bundle used in the evaluation of re-styling was subjected to sensory evaluation in the following five stages by an expert panel (absolute evaluation).

(Evaluation criteria)
5: Good 4: Slightly good 3: Normal 2: Slightly bad 1: Bad

Claims (5)

A hairdressing composition containing the following components (A) and (B).
(A) At least two silicon atoms of the organopolysiloxane segment constituting the main chain, via an alkylene group containing a hetero atom, the following general formula (1);

[Wherein, R ¹ represents a hydrogen atom, an alkyl group having 1 to 22 carbon atoms, an aralkyl group or an aryl group, and n represents 2 or 3. ]
An organopolysiloxane formed by bonding poly (N-acylalkyleneimine) segments composed of repeating units represented by:
The number average molecular weight of the poly (N-acylalkylenimine) segment is 800-1600,
The mass ratio (a / b) of the organopolysiloxane segment (a) constituting the main chain to the poly (N-acylalkylenimine) segment (b) is 65/35 to 82/18,
The weight average molecular weight of the organopolysiloxane segment constituting the main chain is 10,000 to 100,000,
Organopolysiloxane
(B) Polymethacryloyloxyethyltrimethylammonium chloride having a weight average molecular weight of 1 million or more   The hairdressing composition according to claim 1, wherein the content of component (A) is 0.1 to 20% by mass.   The hairdressing composition according to claim 1, wherein the content of component (B) is 0.01 to 2% by mass.   The hair styling composition according to any one of claims 1 to 3, wherein the mass ratio (A) / (B) of the component (A) to the component (B) is 3 to 16.   The hairdressing composition according to any one of claims 1 to 4, having a viscosity of 50 to 20,000 mPa · s.