JP2006265339A - Detergent composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a touch improver which has good compounding stability and a slippery feeling and further can impart higher touch such as softness and a moist feeling, and a detergent composition containing the touch improver. <P>SOLUTION: The touch improver comprises a branched polyglycerol-modified silicone (a) and a surface active agent (b) having a polyglycerol group. and the detergent composition comprises this touch improver and a surface active agent other than the component (b). <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a feel-improving agent and a cleaning composition containing the feel-improving agent, which provides a high feel-improving / moisturizing effect after washing and drying.

The branched polyglycerol-modified silicone is a silicone compound that is compatible with high hydrophilicity while having slipperiness, which is an advantage inherent in silicone, and has excellent wettability and adsorbability to various bases. Patent Document 1 describes an example in which a branched polyglycerol-modified silicone is used as a cosmetic, a fiber treatment agent, and a skin cleansing agent.
JP 2004-339244 A

  Although an improvement in touch is recognized when the branched polyglycerol-modified silicone is blended in the cleaning composition, there is still a demand for further touch such as softness of clothes and moist feeling of hair and skin.

  Accordingly, an object of the present invention is to provide a feeling improver that has good blending stability and slipperiness, and can impart a higher feel such as softness and moistness, and a cleaning agent containing the feel improver. It is to provide a composition.

  The present invention provides (a) a branched polyglycerol-modified silicone, (b) a feel-improving agent containing a surfactant having a polyglycerol group, and a surfactant other than this feel-improving agent and component (b) A cleaning composition containing (c) component) is provided.

  According to the present invention, it is possible to provide a feel improver capable of imparting a higher feel such as softness and moist feeling. In addition, the detergent containing the feel-improving agent, which is excellent in feel, in particular, gives clothes with a slipping feeling and softness, and is a finish garment cleaning agent. It is possible to provide a good hair cleanser and a skin cleanser with a moisturizing feeling that gives the skin a feeling of slipping and moist.

[(A) component]
The branched polyglycerol-modified silicone of component (a) of the present invention includes a branched polyglycerol containing at least one branched glycerol group represented by the following structural formula (1) via a linking group on the silicon atom of the silicone. Mention may be made of branched polyglycerol-modified silicones with at least one chain attached.

(In the formula, the two oxygen atoms are the same or different, and the above structural formula (1), the following structural formula (2), (3) or (4)

The glycerol group or glycidol group represented by these is couple | bonded. )
Note that the glycerol group or glycidol group represented by the structural formula (1), the structural formula (2), (3), or (4) is bonded to the oxygen atom of the structural formula (2), and the structural formula (3) A glycerol group or a glycidol group represented by Structural Formula (1), Structural Formula (2), (3) or (4) is bonded to the oxygen atom.

  The structure of a branched polyglycerol chain containing one or more branched glycerol groups represented by the structural formula (1) (hereinafter referred to as group (1)) as the branching group is a group (1), b structures. Glycidol group represented by formula (2) (hereinafter referred to as group (2)), c glycerol groups represented by structural formula (3) (hereinafter referred to as group (3)), and d groups as end groups A glycerol group represented by the structural formula (4) (hereinafter referred to as group (4)) is bonded.

  In the branched polyglycerol chain, the groups (1), (2) and (3) may be bonded to each other in any sequence. As the number of groups (1) increases, the branched structure develops, and the group (4) is present at the end of each branched chain.

The fact that the branched polyglycerol-modified silicone contains at least one branched structure of the group (1) is easily proved from the fact that a peak specific to the group (1) is observed in ¹³ C-NMR analysis as described later. be able to. Preferably, the average number of groups (1) per polyglycerol chain is 1 or more.

  In the branched polyglycerol-modified silicone, the average total number of bonds (a + b + c + d) of the groups (1), (2), (3) and (4) in the branched polyglycerol chain is determined by NMR analysis or molecular weight comparison with the precursor silicone. Can be calculated, but this is preferably a number of 3 or more. In order for the branched polyglycerol-modified silicone of the present invention to maintain appropriate silicone properties, this value is preferably a number of 3 or more and 200 or less, more preferably 3 to 100, and more preferably 3 to 50. Is particularly preferred, and most preferred is 3-20.

In the branched polyglycerol-modified silicone, the relative ratio of a, b, c and d can be estimated particularly in the system in which the ¹³ C-NMR analysis is performed with a good resolution. The ratio of branching in the branched polyglycerol chain is represented by a / (a + b + c + d). In order to show a sufficient adsorption effect, this value is preferably 1/20 to 1/2, and 1/5 to 1 / 2 is more preferable.

  1 to 100 groups (1) are preferably present in one branched polyglycerol chain, more preferably 2 to 100 groups, and particularly preferably 2 to 10 groups. 2 to 101 groups (4) are preferably present in one branched polyglycerol chain, more preferably 3 to 101 groups, and particularly preferably 3 to 11 groups.

In the branched polyglycerol-modified silicone, the linking group for bonding the silicon atom and the branched polyglycerol chain is not particularly limited, and examples thereof include a group containing an oxyphenylene group. Among such linking groups, the following general formula ( The group represented by 5) (hereinafter referred to as linking group (5)) is preferred. In the linking group (5), the (R ¹ ) _p side is bonded to the silicon atom of the silicone chain, and the (AO) _q side is bonded to the branched polyglycerol chain.

(In the formula, R ¹ may have a substituent, a linear or branched alkylene group or alkenylene group having 1 to 22 carbon atoms, and AO represents an oxyalkylene group or carbon number having 1 to 4 carbon atoms. 6-10 oxyarylene groups, p represents the number of 0 or 1, q represents the number of 0-30, and q AOs may be the same or different.
The silicone forming the branched polyglycerol-modified silicone is a polysiloxane having two or more silicon atoms, and the shape of the polysiloxane may be linear, branched, or cyclic. Moreover, the number average molecular weight of polysiloxane becomes like this. Preferably it is 300-700,000, More preferably, it is 300-200,000, More preferably, it is 1000-20,000. The measurement of the number average molecular weight can be obtained with reference to analysis data such as a gel permeation chromatograph (hereinafter referred to as GPC) method and a light scattering method which will be described later.

  As the branched polyglycerol-modified silicone, those having a structure represented by the general formula (6) (hereinafter referred to as modified silicone (6)) having a linear silicone skeleton are preferable.

(Wherein R ² , R ³ , R ⁴ , u R ⁵ , u R ⁶ , R ⁷ , R ⁸ , R ⁹ are the same or different, and a branched polyglycerol chain is bonded to the other end. A linking group, a linear or branched alkyl group having 1 to 22 carbon atoms, an alkenyl group or an alkoxy group, or an aryl group having 6 to 22 carbon atoms, which may have a substituent, R ² , R ^{At least one of 3} , R ⁴ , u R ⁵ , u R ⁶ , R ⁷ , R ⁸ , and R ⁹ is a linking group having a branched polyglycerol chain bonded to the other end. -Indicates a number of 10,000.
In the modified silicone (6), a branched polyglycerol chain is bonded to the other end of R ² , R ³ , R ⁴ , u R ⁵ , u R ⁶ , R ⁷ , R ⁸ , R ^9. The groups other than the linking group are the same or different, and may have a substituent, a linear or branched alkyl group, alkenyl group or alkoxy group having 1 to 22 carbon atoms, or 6 to 22 carbon atoms. Examples of the alkyl group having 1 to 22 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, and nonyl groups. Examples of the alkenyl group having 1 to 22 include a vinyl group and an allyl group. Examples of the alkoxy group having 1 to 22 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentyloxy, and hexyloxy. Heptyloxy, octyloxy, and a phenoxy group. In these, a C1-C12 linear or branched alkyl group, a vinyl group, an allyl group, or a C6-C12 aryl group is preferable, More preferably, a C1-C3 alkyl group or A phenyl group, particularly preferably a methyl group, a propyl group or a phenyl group. Among these, a methyl group is more preferable from the viewpoint of versatility and price, but a phenyl group is more preferable from the viewpoint of heat resistance.

In the modified silicone (6), the substituents that R ^{2 to} R ⁹ may have include a phenyl group, a phenol group, a hydroxy group, a carboxy group, an amino group (having 0 to 14 carbon atoms), an imino group, Examples include (aminoethyl) amino group, (dimethylaminoethyl) amino group, polyoxyalkylene group, mercapto group, and epoxy group. When it has these substituents, a propyl group is particularly preferable as R ^{2 to} R ⁹ .

In the modified silicone (6), at least one of R ^{2 to} R ⁴ , u R ⁵ , u R ⁶ , R ^{7 to} R ⁹ , preferably 1 to 10, more preferably 1 to Two are linking groups having a branched polyglycerol chain bonded to the other end. This linking group is preferably an oxyphenylene group-containing linking group, and may be located at any of the side chain, one end, or both ends of the modified silicone (6), or a mixture thereof. When the linking group is present only in any one of R ^{2 to} R ⁴ and any one of R ^{7 to} R ⁹ , the branched polyglycerol-modified silicone of the present invention is a bi-terminally substituted branch. It becomes polyglycerol-modified silicone, and is highly preferable because it can be connected to each other in water or other solvents to easily adopt a higher-order structure. In addition, when three or more linking groups are present in R ⁵ or R ⁶ , the branched polyglycerol-modified silicone of the present invention is a side-chain multi-substituted branched polyglycerol-modified silicone, which is preferable because of increased hydrophilicity and adsorption ability. .

  In the modified silicone (6), u represents a number of 0 to 10,000, preferably a number of 1 to 3,000, more preferably a number of 5 to 500, particularly preferably a number of 10 to 150. .

  In the branched polyglycerol-modified silicone of the present invention, the total number of silicon atoms (Si) in the silicone and the groups (1), (2), (3) and (4) in the branched polyglycerol chain (hereinafter, The ratio (G / Si) of (G) (referred to as the number of glycerol groups) is preferably 0.001 to 50, more preferably 0.05 to 10, still more preferably 0.1 to 3, and particularly preferably 0.15 to 1. . Within this range, the residual rate of adsorption to various substrates, skin, hair and fibers is high.

  In the branched polyglycerol-modified silicone, as long as the silicone-like characteristics, the hydrophilic properties and the high adsorptivity described above, which are the characteristics of the branched polyglycerol-modified silicone, are not significantly inhibited, A small amount of oxyethylene groups and / or oxypropylene groups may be present. Oxyethylene groups or / and oxypropylene groups may be present randomly in the branched polyglycerol chain, or a plurality of oxyethylene groups or / and oxypropylene groups form a chain and block in the branched polyglycerol chain. May be present. At this time, the block composed of a plurality of oxyethylene groups and / or oxypropylene groups may be present on the linking group side of the branched polyglycerol chain or may be present at the end of the branched chain of the branched polyglycerol chain. Alternatively, it may be present in the middle of the branched polyglycerol chain. When an oxyethylene group or / and an oxypropylene group are present, the oxyethylene group and / or oxypropylene group is preferably 0.001 to 0.5 molar equivalents relative to 1 molar equivalent of the glycerol group, More preferred is 0.2 molar equivalent.

[Component (b)]
The component (b) of the present invention is a surfactant having a polyglycerol group, and the polyglycerol group has two or more glycerol groups. By having two or more glycerol groups, softness and moist feeling can be expressed when used as a feel improver. The upper limit of the number of glycerol groups is not particularly limited, but is preferably 30 or less.

  As the component (b), polyglycerol fatty acid ester type surfactants and polyglycerol alkyl ether type surfactants are preferable.

  Preferred examples of the polyglycerol fatty acid ester type surfactant include surfactants such as polyglycerol fatty acid ester and polyglycerol ricinoleic acid ester, and among them, polyglycerol fatty acid ester is particularly preferable. The fatty acid constituting the polyglycerol fatty acid ester is preferably a fatty acid having 8 to 22 carbon atoms, and examples thereof include stearic acid, oleic acid, caprylic acid, lauric acid, myristic acid and the like. Specific examples of preferred polyglycerin fatty acid esters include decaglyceryl monostearate, hexaglyceryl monostearate, pentaglyceryl monostearate, decaglyceryl monolaurate, hexaglyceryl monolaurate, pentaglyceryl monolaurate, decaglyceryl monomyristate, mono Examples include hexaglycerin myristate and decaglycerin monooleate.

  As the polyglycerol alkyl ether type surfactant, polyglycerol alkyl ether is preferable. The polyglycerin chain of the polyglycerin alkyl ether may be linear but may have a branched structure.

  Here, the alkyl group constituting the polyglycerin alkyl ether is not particularly limited, but those having a linear or branched structure having 1 to 52 carbon atoms are preferred, such as a methyl group, an ethyl group, a propyl group, Butyl, pentyl, hexyl, octyl, 2-ethylhexyl, nonyl, decyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl, 2-ethylhexadecyl, isostearyl, oleyl Group, eicosyl group, behenyl group, 2-decyltetradecyl group, 2-hexadecyleicosyl group and the like.

  2-20 are preferable, as for HLB of (b) component, 8-16 are still more preferable, and 12-16 are especially preferable. When the HLB is 20 or less, blending becomes easy, and when the HLB is 16 or less, a particularly high finish feeling is obtained.

  Here, the HLB is obtained experimentally. In other words, the HLB known surfactant and the unknown surfactant are combined to emulsify the HLB known oil and water, and the one with the best mixing ratio can be selected and calculated from the formula (I).

{(W _u × HLB _u ) + (W _a × HLB _a )} / (W _u + W _a ) = HLB ₀ (I)
[Wherein, W _u: HLB is mass fraction of the unknown surfactant, W _a: HLB mass fraction of known surfactants, HLB _u: HLB is an unknown surfactant HLB, HLB _a: HLB is a known surfactant HLB, HLB ₀ : HLB is a known fat and oil HLB. ]
[Feel improving agent and cleaning composition]
The feel improving agent of this application contains the said (a) component and (b) component. The mass ratio of the component (a) and the component (b) is preferably 100/1 to 50/50, and more preferably 95/5 to 70/30.

  The cleaning composition of the present invention contains a feel improver according to the present invention and a component (c) which is a surfactant other than the component (b). The cleaning composition of the present invention is used as a cleaning composition for clothing intended for clothing, a cleaning composition for hair intended for hair, and a cleaning composition for skin intended for skin.

  The cleaning composition of the present invention preferably contains 0.01 to 10% by mass, preferably 0.1 to 5.0% by mass, of the feel improving agent of the present invention in order to realize a significant improvement in feel. Is more preferable, and it is particularly preferable to include 0.5 to 2.0% by mass. In addition, the content of the component (c) in the cleaning composition of the present invention is preferably 0.1 to 45% by mass from the viewpoint of improving cleaning properties.

  The component (c) used in the cleaning composition of the present invention is not particularly limited as long as it is a surfactant having no polyglycerol group, and is appropriately selected depending on the use of the cleaning composition. As the component (c), nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants are preferably used.

  The nonionic surfactant is not particularly limited as long as it is a component contained in ordinary detergents, surface treatment agents, and fiber treatment agents. Sorbitan fatty acid esters, glycerin fatty acid esters, propylene glycol fatty acid esters, hydrogenated castor oil Derivatives, lipophilic nonionic surfactants such as glycerin alkyl ethers, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbit fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene alkyl ether , Polyoxyethylene alkylphenyl ethers, pluronic types, polyoxyethylene / polyoxypropylene alkyl ethers, tetrapolyoxyethylene / tetrapolyoxypropylene ethylene Diamine condensates, polyoxyethylene castor oil or hardened castor oil derivative, polyoxyethylene beeswax / lanolin derivative, alkanolamide, polyoxyethylene propylene glycol fatty acid ester, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, sucrose fatty acid ester, Examples include polyoxyethylene nonylphenyl formaldehyde condensate, alkylethoxydimethylamine oxide, and trioleyl phosphate.

  The anionic surfactant is not particularly limited as long as it is a component contained in a normal cleaning agent, surface treatment agent, and fiber treatment agent. Alkyl (or alkenyl) sulfate, polyoxyalkylene alkyl (or alkenyl) ether sulfate , Alkane sulfonate, olefin sulfonate, alkylbenzene sulfonate, alkyl (or alkenyl) sulfosuccinate, dialkyl (or dialkenyl) sulfosuccinate, polyoxyalkylene alkyl (or alkenyl) sulfosuccinate, alkyl (or alkenyl) ) Ether carboxylate, polyoxyalkylene alkyl (or alkenyl) ether carboxylate, alkyl (or alkenyl) phosphate ester salt, polyoxyalkylene alkyl (or alkenyl) ether phosphate, fatty acid or Salts, N- acyl glutamic acid or its salt, N- acyl taurates or salts thereof, N- acyl methyl taurine, and the like.

  The cationic surfactant is not particularly limited as long as it is a component contained in a normal cleaning agent, surface treatment agent, and fiber treatment agent. For example, a quaternary ammonium salt represented by the following general formula (7) is used. Can be mentioned.

[Wherein, at least one of R ¹⁰ , R ¹¹ , R ¹² and R ¹³ is substituted with an alkoxy group, alkenyloxy group, alkanoylamino group or alkenoylamino group having a total carbon number of 8 to 28. An optionally substituted alkyl group or alkenyl group, the remainder being a benzyl group, an alkyl group having 1 to 5 carbon atoms or a hydroxyalkyl group, or a polyoxyethylene group having a total addition mole number of 10 or less, and Z ⁻ is a halide ion or Indicates an organic anion. ]
Amphoteric surfactants include amide amino acids, carbobetaines, amide betaines, sulfobetaines, hydroxysulfobetaines, amide sulfobetaines, imidazolinium betaines, amino acids, phosphobetaines, phosphate esters. These are amphoteric surfactants. The counter ion of the anionic group of these amphoteric surfactants includes alkali metal ions such as sodium ions and potassium ions, ammonium ions, and alkanolamines having 1 to 3 alkanol groups having 2 to 3 carbon atoms (for example, monoethanol Amine, diethanolamine, triethanolamine, triisopropanolamine) and the like, and counter ions of the cationic residue include halogen ions such as chlorine, bromine and iodine, methosulphate and saccharinate ions.

  As the component (c), for example, in the case of a cleaning composition for clothing, it is preferable to contain a nonionic surfactant, an anionic surfactant and a cationic surfactant. It is particularly preferable to contain an ionic surfactant. Examples of these nonionic surfactants include the above-described nonionic surfactants, and polyoxyethylene alkyl ethers having an alkyl group having 8 to 22 carbon atoms and an average addition mole number of oxyethylene groups of 12 mol or less are particularly preferable.

  In the case of a hair cleaning composition, it preferably contains an anionic surfactant and an amphoteric surfactant, and more preferably contains an anionic surfactant in terms of detergency. Examples of the anionic surfactant include the above-mentioned anionic surfactants. Among them, polyoxyalkylene alkyl (or alkenyl) having 1 to 30 carbon atoms of an alkyl group or alkenyl group and an average addition mole number of 1 to 30 oxyalkylene groups. It is particularly preferable to use ether sulfate.

  In the case of a skin cleanser composition, it is preferable to contain at least one selected from nonionic surfactants and anionic surfactants, and anionic surfactants are particularly preferred from the standpoint of foaming power and cleaning power. Examples of the anionic surfactant include the above-mentioned anionic surfactants. Among them, an alkyl phosphate ester salt having 1 to 30 carbon atoms of an alkyl group, a higher fatty acid salt having 1 to 30 carbon atoms, and an alkyl group having 1 to 30 carbon atoms. It is particularly preferred to use an alkyl sulfate of

  In the cleaning composition of the present invention, in addition to the component (a), the component (b) and the component (c), the components to be mixed in a normal cleaning composition may be appropriately mixed depending on the use. it can. When the cleaning composition of the present invention is used for clothing, for example, alkali metal hydroxides, silicates, carbonates such as sodium carbonate, and alkaline agents such as alkanolamines; alcohols such as ethanol, Glycols such as ethylene glycol and propylene glycol, paratoluenesulfonic acid, benzoate, and thickeners and solubilizers such as urea; phase modifiers such as polyoxyalkylene benzyl ether and polyoxyalkylene phenyl ether and detergency Improving agents: aminopolyacetates such as nitrilotriacetic acid, ethylenediaminetetraacetate, iminodiacetate, diethylenetriaminepentaacetate, glycol etherdiaminetetraacetate, hydroxyethyliminodiacetate and triethylenetetraminehexaacetate, malonic acid , Succinic acid, malic acid, diglyco Metal ion scavengers such as phosphoric acid, tartaric acid and citric acid; polyacrylic acid, polymaleic acid, carboxymethyl cellulose, polyethylene glycol having an average molecular weight of 5000 or more, maleic anhydride-diisobutylene copolymer, maleic anhydride-methyl vinyl ether copolymer Polymer, maleic anhydride-vinyl acetate copolymer, naphthalenesulfonate formalin condensate, and claims 1 to 21 of JP 59-62614 (page 1, column 3, line 5 to page 3, column 4, line 14) Recontamination preventives and dispersants such as the described polymers; Color transfer preventives such as polyvinyl pyrrolidone; Bleaching agents such as sodium percarbonate or sodium perborate; Tetraacetylethylenediamine, general formula (I- 2) to bleach activators such as bleach activators represented by (I-7); amylase, Enzymes such as rotase, lipase and cellulase; enzyme stabilizers such as calcium chloride, calcium sulfate, formic acid and boric acid (boron compound); Fluorescent dyes; Silica, antifoaming agents such as silicones other than component (a); antioxidants such as butylhydroxytoluene, distyrenated cresol, sodium sulfite and sodium bisulfite; bluing agents; fragrances; antibacterial preservatives and the like It is done.

  When the cleaning composition of the present invention is used for hair or skin, for example, anti-dandruff agent; vitamin agent; bactericidal agent; anti-inflammatory agent; preservative; deodorant agent; chelating agent; Moisturizers; coloring agents such as dyes and pigments; viscosity modifiers such as hydroxyethylcellulose, methylcellulose, polyethylene glycol, clay minerals; pH modifiers such as citric acid and potassium hydroxide; plant extracts; fragrances; ultraviolet absorbers; Inhibitors; pearlizing agents; and other components described in ENCYCLOPEDIA OF SHAMPOO INGREDIENTS (MICELLE PRESS).

  The form of the cleaning composition of the present invention can be appropriately selected from a liquid form, a powder form, a gel form, a granular form, and the like, but a liquid form using water or a lower alcohol, particularly water, as a solvent is preferable.

Production Example 1 (component (a): synthesis of branched polyglycerol-modified silicone A)
Phenol-modified silicone (made by Toray Dow Corning Silicone Co., Ltd., trade name: BY16-752 [both ends modified, specific gravity = 0.99 g / ml, viscosity = 110 cst, hydroxy group equivalent = 1500 (average molecular weight = 3000 equivalent) , GPC (column: G4000HXL + G2000HXL (manufactured by Tosoh Corporation)), THF solution (50 mmol / L acetic acid added), 40 ° C., polystyrene conversion) actual value; number average molecular weight (Mn) = 2340, weight average molecular weight (Mw) = 4780 ] 450 g was taken into a flask, 15 mL of 1 M potassium hydroxide ethanol solution was added, and the mixture was heated to 95 ° C. under reduced pressure with stirring to obtain a potassium-modified phenol-modified silicone as a pale orange oil. Under vigorous stirring, 77.8 g (3.5 equivalents) of glycidol was added over 5 hours using a quantitative feed pump. After further heating and stirring for 20 minutes and cooling to room temperature, a pale yellow viscous oily product was obtained. Ethanol (500 mL) was added to the obtained branched polyglycerol-modified silicone, and potassium was removed and concentrated using a cation exchange resin to obtain a branched polyglycerol-modified silicone A as a slightly yellow oil (yield: 99.5%).

The obtained branched polyglycerol-modified silicone A was confirmed to be a branched polyglycerol-modified silicone having a group (1) by analysis of ¹³ C-NMR spectrum. Moreover, by analysis of ¹ H-NMR spectrum, average glycerol number (G) = 7.0 (one side 3.5), average number of silicon atoms (Si) = 33.5, G / Si ratio is 0.21, According to GPC analysis, the number average molecular weight (Mn) was 2850.

The assignment of each peak in the ¹ H-NMR spectrum of the branched polyglycerol-modified silicone is roughly as follows, although it slightly shifts depending on the solvent. The average glycerol number was determined from the H number of the branched polyglycerol chain in the ¹ H-NMR spectrum.
0.0-0.2 ppm: Si-C H ₃
0.6-0.7 ppm: Si—C H ₂ —CH ₂ — (4H)
_{1.5-1.7ppm: Si-CH 2 -C H} 2 - (4H)
_{2.5-2.7ppm: Si-CH 2 -CH 2} -C H 2 - (4H)
3.3-4.0 ppm: H of branched polyglycerol chain (excluding terminal hydroxy groups, 5H × number of glycerol groups)
6.7-7.2 ppm: phenol (8H)
In the ¹³ C-NMR spectrum, the assignments of the groups (1) to (4) forming the branched polyglycerol chain were based on the values described in Macromolecules, 1999, 32, 4240.

Examples 1-3, Comparative Examples 1-2
(A) The branched polyglycerol-modified silicone A obtained in Production Example 1 as the component, the following (b-1) to (b-3) as the component (b), and other components are blended in the composition of Table 1, A cleaning composition for clothing was prepared. About the obtained composition, sensory evaluation was performed by the following method. The results are shown in Table 1.

<(B) component>
(B-1): Decaglycerin monolaurate (Taiyo Kagaku Co., Ltd., Sunsoft M-12J), HLB = 15.5, light brown soft solid, iodine value = 3 or less (b-2): Hexaglycerol monolaurate (Taiyo Chemical Co., Ltd., Sunsoft Q-12DF), HLB = 13.0, light brown soft solid, iodine number = 2 or less (b-3): hexaglycerin monostearate (Taiyo Chemical Co., Ltd., Sunsoft) Q-18F), HLB = 10.5, light brown pellets, iodine value = 2 or less, melting point = 42-50 ° C.
<Sensory evaluation method>
1) Washing Into a bowl filled with 5 L of water, 12 g of each composition shown in Table 1 is added and stirred uniformly. Place one piece of clothing (approx. 280 g, washed in advance with a commercial clothing detergent, rinsed thoroughly and dried), hand-washed for 5 minutes, rinsed and dehydrated (3 minutes), and dried at 20 ° C / humidity Dry in a 35% constant temperature room for 24 hours.

2) Sensory evaluation The feel (slip feeling, softness, good finish) of the clothes washed by the method described above was evaluated according to the following criteria using five evaluation panelists. The evaluation with the most votes obtained was taken as the evaluation result.
・ Slippery feeling of clothing ○: A slippery feeling is imparted to the clothing and it is very dry.
Δ: Slightly slippery feeling is imparted to the clothing, and the clothing is somewhat smooth.
X: There is no slipperiness in clothes and it does not dry.
-Softness of clothing A: Finished very softly.
○: Clothing is finished softly.
(Triangle | delta): Clothes are finished a little softly.
X: Clothes are hard.
-Good finish ◎: Very good ○: Good △: Normal ×: Bad

Examples 4-6, Comparative Examples 3-4
(A) The branched polyglycerol-modified silicone A obtained in Production Example 1 as the component, (b-1) to (b-3) as components (b), and other components are blended in the composition of Table 2, A hair detergent composition was prepared. About the obtained composition, sensory evaluation was performed by the following method. The results are shown in Table 2.

<Sensory evaluation method>
1) Hair washing After wetting a test hair bundle (hair obtained by cumulative bleaching of Japanese female hair 5 times, length: about 15 cm, mass: 20 g) with warm water at 40 ° C., 3 g of the composition shown in Table 2 was added. After washing for 1 minute, it was rinsed with warm water for 30 seconds. Towel drying was performed, followed by light brushing and drying with a dryer, and then sensory evaluation was performed.

2) Sensory evaluation The feel (smoothness, moistness, and good finish) of the hair washed by the above-described method was evaluated according to the following criteria using three evaluation panelists. The evaluation with the most votes obtained was taken as the evaluation result.
-Hair slipperiness ○: The hair is slippery and very smooth.
Δ: A little slipperiness is imparted to the hair, and it is somewhat smooth.
X: The hair does not feel slippery and does not dry.
-Hair moist feeling ◎: The hair is very moist.
○: The hair is moist.
Δ: Hair is slightly moist.
X: Hair is not moist.
-Good finish ◎: Very good ○: Good △: Normal ×: Bad

Examples 7-9, Comparative Examples 5-6
(A) The branched polyglycerol-modified silicone A obtained in Production Example 1 as the component, the following (b-1) to (b-3), and other components as the component (b) with the composition shown in Table 3, A skin cleanser composition was prepared. About the obtained composition, sensory evaluation was performed by the following method. The results are shown in Table 3.

<Sensory evaluation method>
One expert panelist took an appropriate amount of each composition on a sponge soaked in hot water at the time of bathing, washed the body, and performed sensory evaluation based on the following criteria.
・ Skin slipperiness ○: The skin feels slippery and very dry.
Δ: Slightly slippery feeling is imparted to the skin, and it is somewhat smooth.
X: The skin does not feel slippery and does not dry.
-Skin moist feeling ◎: The skin is very moist.
○: The skin is moist.
Δ: The skin is slightly moist.
X: Skin is not moist.
-Good finish ◎: Very good ○: Good △: Normal ×: Bad

Claims (9)

  A feel improver comprising (a) a branched polyglycerol-modified silicone and (b) a surfactant having a polyglycerol group. (A) The branched polyglycerol chain in which at least one branched polyglycerol chain containing at least one branched glycerol group represented by the following structural formula (1) is bonded to a silicon atom of silicone via a linking group The feel improving agent according to claim 1, which is glycerol-modified silicone.

(In the formula, the two oxygen atoms are the same or different, and the above structural formula (1), the following structural formula (2), (3) or (4)

The glycerol group or glycidol group represented by these is couple | bonded. )   The feel improving agent according to claim 1 or 2, wherein the component (b) has an HLB of 2 to 20.   The feel improver according to any one of claims 1 to 3, wherein the component (b) is a polyglycerol fatty acid ester type surfactant or a polyglycerol alkyl ether type surfactant.   A detergent composition comprising the feel improver according to any one of claims 1 to 4 and a surfactant other than the component (b).   The cleaning composition according to claim 5, wherein the content of the feel improver is 0.01 to 10% by mass.   The cleaning composition according to claim 5 or 6 intended for clothing.   The cleaning composition according to claim 5 or 6, intended for hair. The cleaning composition according to claim 5 or 6, which is intended for skin.