Oily composition and hair conditioning formulation containing the same

Abstract

The present invention relates to an oily composition comprising an oily solvent selected from hydrocarbon oils, and an alkyl-terminated amino-functionalized silicone dissolved or dispersed in the oily solvent, and to a method for preparing the same. The present invention also relates to a hair conditioning formulation containing the oily composition, and to a method for conditioning hair using the formulation.

Description

[Technical Field]

[0001] The present invention relates to an oily composition comprising an oily solvent selected from hydrocarbon oils, and an alkyl-terminated amino-functionalized silicone dissolved or dispersed in the oily solvent, and a method for preparing the same. The present invention also relates to a hair conditioning formulation comprising the oily composition, and a method for conditioning hair using the formulation. [Background technology]

[0002] Hair normally has a thin, lipophilic film on the hair cuticle that provides protection. When hair becomes dry and / or damaged due to the surrounding environment, styling, regular washing, drying, and chemical treatments such as coloring and perms, the lipophilic substances in the film decrease dramatically. As a result, the hair takes on a dull appearance, loses its smoothness, and becomes brittle and prone to breakage.

[0003] Various techniques for conditioning and restoring such damaged hair are known in the technical field. One common technique is to use hair care compositions containing conditioning agents such as functionalized silicones. Amino-functionalized silicones, in particular, are used to impart conditioning benefits to the hair, such as lubrication of the hair surface and restoration of the lipophilicity of the hair cuticle.

[0004] Greasy amino-functionalized silicones are generally emulsified in water or dispersed in a low-viscosity silicone oil (polydimethylsiloxane oil) to form an emulsion of a dispersion convenient for storage and transportation. There is still a need to provide a composition of such amino-functionalized silicones that can be stable over a long period and bring overall improved conditioning benefits. It is desirable that this composition can provide functional benefits such as flexibility, smoothness of dry hair without stickiness or an oily feel, hair moisturization, ease of handling of hair, and good combability. It is highly desirable that this composition can provide excellent recovery of hair from damage caused by natural environmental factors or chemical hair treatments.

Summary of the Invention

[0005] In one aspect, the present invention relates to an oily composition: (a) An oily solvent selected from hydrocarbon oils; and (b) A silicone having the general formula (I) dissolved or dispersed in the oily solvent: M 1 D 1 x D 2 y M 2 (I) Wherein M 1 =R 1 R 2 R 3 SiO 0.5 M 2 =R 4 R 5 R 6 SiO 0.5 D 1 =SiR 7 R 8 O D 2 =SiR 9 R 10 O Here R 1 、R 2 、R 4 、R 5, R 7 , R 8 and R 9 Each is independently selected from a monovalent hydrocarbon group having approximately 1 to 6 carbon atoms; R 3 and R 6 Each is independently selected from alkyl groups having approximately 20 to approximately 60 carbon atoms; Each R 10 These are independently selected from the 3-aminopropyl group and the N-(2-aminoethyl)-3-aminopropyl group; The subscript x has a value of approximately 1 to approximately 2,000, and the subscript y has a value of approximately 1 to approximately 50.

[0006] In another embodiment, the present invention relates to a method for preparing an oily composition, which optionally includes dispersing or dissolving component (b) in component (a) at a high temperature.

[0007] In yet another embodiment, the present invention relates to a formulation comprising the oily composition of the present invention for conditioning hair.

[0008] In a further embodiment, the present invention relates to a method for conditioning hair, which includes applying a formulation containing an oily composition to the hair.

[0009] The oily composition of the present invention can provide effective restoration of damaged hair while simultaneously exhibiting overall sensory benefits such as flexibility, smoothness of dry hair without stickiness or oiliness, moisturizing effect, and manageability. [Brief explanation of the drawing]

[0010] Figure 1 shows a bar graph of hair restoration test A for various compositions.

[0011] Figure 2 shows hair traces treated with the compositions of Example 1, Comparative Example 2, and Comparative Example 4.

[0012] Figure 3 shows the functional diagrams for the compositions of Example 1 and Comparative Example 5.

[0013] Figure 4 shows hair traces treated with the compositions of Example 1 and Comparative Example 5.

[0014] Figure 5 shows a functional diagram of the hair rinse-off conditioner formulation of Example 9.

[0015] Figure 6 shows a functional diagram of the shampoo formulation of Example 10. [Modes for carrying out the invention]

[0016] In the specification and claims of this application, the following terms and expressions shall be understood as set forth below.

[0017] The singular forms "aru" (to be), "hitotsu" (one), and "sono" (that) include the plural form, and references to specific numbers include at least that specific number unless otherwise specified in the context.

[0018] All methods described herein may be performed in any suitable order, unless otherwise specified herein or unless it is particularly evident in the context. All examples or use of exemplary terms (e.g., “like”) presented herein are intended solely to make the invention more understandable and do not impose any limitations on the scope of the invention unless otherwise specified.

[0019] No term used herein should be construed as indicating that any component not described in the claims is essential to carrying out the invention.

[0020] The terms “include,” “contain,” and “contain,” and their grammatically equivalent expressions, are understood to be inclusive or non-restrictive terms that do not exclude additional unspecified components or methodological processes, and also include the more restrictive terms “consist of” and “essentially consist of.”

[0021] Except in the examples, or unless otherwise specified, all numerical values ​​expressing quantities of materials, temperatures, durations of time, quantified properties of substances, and other matters described herein and in the claims shall be understood in all cases as being modified by the term "about," whether or not the term "about" is used in the expression.

[0022] It is understood that any numerical range described in this application includes all subranges within that range, and any combination of various endpoints of such ranges or subranges.

[0023] Furthermore, all compounds, materials, or substances explicitly or implicitly disclosed herein and / or described in the claims as belonging to a group of compounds, materials, or substances that are constitutively, compositionally, and / or functionally related are understood to include the individual components of that group and all combinations thereof.

[0024] The expression "hydrocarbon group" means any hydrocarbon from which one or more hydrogen atoms have been removed, and includes alkyl groups, alkenyl groups, alkynyl groups, cyclic alkyl groups, cyclic alkenyl groups, cyclic alkynyl groups, and phenyl groups, and also includes hydrocarbon groups containing at least one heteroatom.

[0025] The term "alkyl" means any monovalent, saturated linear, branched, or cyclic hydrocarbon group; the term "alkenyl" means any monovalent, linear, branched, or cyclic hydrocarbon group containing one or more carbon-carbon double bonds, where the bond position of this group may be a carbon-carbon double bond or any other; and the term "alkynyl" means any monovalent, linear, branched, or cyclic hydrocarbon group containing one or more carbon-carbon triple bonds, and optionally one or more carbon-carbon double bonds, where the bond position of this group may be a carbon-carbon triple bond, a carbon-carbon double bond or any other.

[0026] The expressions “cyclic alkyl,” “cyclic alkenyl,” and “cyclic alkynyl” include bicyclic, tricyclic, and higher-order cyclic structures, as well as these cyclic structures further substituted with alkyl groups, alkenyl groups, and / or alkynyl groups.

[0027] The term "heteroatom" refers to any of the elements in groups 13-17, excluding carbon, and includes, for example, oxygen, nitrogen, silicon, sulfur, phosphorus, fluorine, chlorine, bromine, and iodine.

[0028] Useful hydrocarbon groups include alkyl groups, examples of which are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and tert-pentyl; as well as hexyl groups such as n-hexyl. Examples of alkenyl groups include vinyl, propenyl, allyl, methallyl, and cyclohexenyl. Examples of alkynyl groups include acetylenyl, propargyl, and methylacetylenyl.

[0029] As used in this application, the term “oil-based composition” is understood to mean an emulsified or unemulsified, preferably unemulsified, composition formed from a plurality of substances formulated for the purpose of hair care and / or hair conditioning, in which the oil-based solvent is a continuous phase. These plurality of substances may form a homogeneous phase without phase interfaces, such as a solution, or a heterogeneous phase with phase interfaces, such as a dispersion. As used in this application, the term “oil-based solvent” is understood to include any lipophilic or hydrophobic non-aqueous solvent that is liquid at room temperature (25°C) and atmospheric pressure (760 mmHg).

[0030] In the context of this application, the term "hydrocarbon oil" means an oil that primarily contains or consists of hydrogen atoms and carbon atoms.

[0031] The terms or words used in the detailed description and claims should not be interpreted restrictively in their ordinary or dictionary sense, but rather should be interpreted in a sense and concept consistent with the concepts of the present invention, based on the principle that inventors can appropriately define the concepts of terms in a way that best describes their invention.

[0032] In one embodiment, the present invention relates to an oily composition: (a) an oily solvent selected from hydrocarbon oils; and (b) containing a silicone having general formula (I) that is dissolved or dispersed in an oily solvent: M 1 D 1 x D 2 y M 2 (I) During the ceremony, M 1 =R 1 R 2 R 3 SiO 0.5 M 2 =R 4 R 5 R 6 SiO 0.5 D 1 =SiR 7 R 8 O D 2 =SiR 9 R 10 O Here R 1 , R 2 , R 4 , R 5 , R 7 , R 8 and R 9 Each is independently selected from a monovalent hydrocarbon group having approximately 1 to 6 carbon atoms; R 3 and R 6 Each is independently selected from alkyl groups having approximately 20 to approximately 60 carbon atoms; Each R 10 These are independently selected from the 3-aminopropyl group and the N-(2-aminoethyl)-3-aminopropyl group; The subscript x has a value of approximately 1 to approximately 2,000, and the subscript y has a value of approximately 1 to approximately 50.

[0033] The oily composition of the present invention may or may not be emulsified. If the composition is emulsified, a surfactant and / or water may be added. Any anionic surfactant, cationic surfactant, nonionic surfactant, and amphoteric surfactant may be used as the surfactant, and these may be used alone or in combination of two or more. In a preferred embodiment, the oily composition is not emulsified. In one preferred embodiment, the oily composition is substantially free of surfactant or does not contain surfactant. Preferably, the composition contains 2% by weight or less, particularly 1.5% by weight or less, and more specifically 1% by weight or less of surfactant. When an unemulsified composition is incorporated into an oily conditioning product, such as hair oil, particularly hair tail oil, it provides excellent hair conditioning and restorative effects.

[0034] In embodiments, the hydrocarbon oil (a) is selected from linear or branched hydrocarbon oils having about 8 to about 20 carbon atoms, particularly about 8 to about 19 carbon atoms, more specifically about 8 to about 18 carbon atoms, preferably about 9 to about 16 carbon atoms, about 9 to about 15 carbon atoms, and more preferably about 9 to about 14 carbon atoms. In specific embodiments, the hydrocarbon oil is selected from linear or branched alkane oils having about 8 to about 16 carbon atoms; preferably from linear or branched octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, cetane, or mixtures thereof; and more preferably from linear or branched nonane, decane, undecane, dodecane, or mixtures thereof. In specific embodiments, the hydrocarbon oil is isododecane. In another specific embodiment, the hydrocarbon oil is a C9-12 alkane. These hydrocarbon oils may be used alone or in combination of two or more of them.

[0035] When hydrocarbon oils, particularly alkane oils having 9 to 12 carbon atoms, such as isododecane, are used as a solvent in combination with the amino-functionalized silicone of component (b), the resulting composition, due to its compatibility, exhibits improved hair restoration effects with improved functional attributes, resulting in a non-oily or sticky feel, compared to conventionally used low-viscosity silicone oils as solvents for functionalized silicones. The hydrocarbon oil allows the active ingredient, the amino-functionalized silicone (b), to be present in the oily composition at a concentrated concentration of up to about 50% by weight (e.g., up to about 40% by weight, up to about 30% by weight, or up to about 20% by weight based on the total weight of the composition), while the resulting composition remains stable. The oily composition maintains compatibility with a variety of formulations for treating or conditioning hair, including formulations based on silicone oils or aqueous emulsions, in addition to formulations based on organic oils.

[0036] Hydrocarbon oil (a) may be present in the oily composition in an amount of at least about 50% by weight, particularly at least about 55% by weight, more specifically at least about 60% by weight, for example at least about 65% by weight, at least about 70% by weight, at least about 75% by weight, or at least about 80% by weight, based on the total weight of the composition. In general, hydrocarbon oil (a) may be present in the oily composition in an amount of about 99.99% by weight or less, particularly about 99.95% by weight or less, more specifically less than about 99.9% by weight, for example less than about 99.5% by weight, less than about 99% by weight, less than about 98% by weight, or less than about 97% by weight, based on the total weight of the composition.

[0037] In the embodiment, in formula (I) of component (b), R 1 , R 2 , R 4 , R 5 , R 7 , R 8 and R 9 Each is independently selected from a monovalent hydrocarbon group having about 1 to about 6 carbon atoms, which may be unsubstituted or substituted with a halogen atom selected from, for example, F, Cl, Br and combinations thereof. In one embodiment, R 1 , R 2 , R 4 , R 5 , R 7 , R 8 and R 9 Each is independently selected from a phenyl group or alkyl group having about 1 to about 6 carbon atoms. Preferably, R 1 , R 2 , R 4 , R 5 , R 7 , R 8 and R 9 Each of these is independently selected from alkyl groups having about 1 to about 4 carbon atoms; in particular methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, and i-butyl; and more specifically from the methyl group.

[0038] In formula (I) of component (b), R 3 and R 6is independently selected from alkyl groups which are either linear or branched and have from about 20 to about 60 carbon atoms, particularly from about 24 to about 54 carbon atoms, or from about 51 to about 60 carbon atoms, more specifically from about 30 to about 50 carbon atoms, and preferably from about 35 to about 45 carbon atoms, such as having about 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, or 45 carbon atoms.

[0039] In formula (I) of component (b), R 10 is independently selected from 3-aminopropyl groups and N-(2-aminoethyl)-3-aminopropyl groups. In one embodiment, R 10 is an N-(2-aminoethyl)-3-aminopropyl group.

[0040] In a particular embodiment of component (b), R 1 , R 2 , R 4 , R 5 , R 7 , R 8 and R 9 are methyl; R 3 and R 6 are each independently an alkyl group which is either linear or branched and has from about 35 to about 45 carbon atoms; and R 10 is an N-(2-aminoethyl)-3-aminopropyl group.

[0041] In formula (I) of component (b), x has a value from about 100 to about,1500, particularly from about 200 to about 1000, more specifically from about 300 to about 1000, such as from about 350 to about 950, from about 400 to about 900, from about 500 to about 850, from about 550 to about 800, or from about 600 to about 700. The subscript y has a value from about 1.5 to about 40, particularly from about 2 to about 30, and more specifically from about 3 to about 20, such as from about 3.5 to about 17.5, from about 4.0 to about 17, or from about 5.0 to about 15.0. In a specific embodiment, x is about 650 and y is about 3.5. In another specific embodiment, x is about 650 and y is about 8.5.

[0042] In embodiments, the silicone of component (b) may be present in the oily composition in an amount of at least about 0.05% by weight, particularly at least about 0.08% by weight, more specifically at least about 0.1% by weight, for example at least about 0.2% by weight, at least about 0.3% by weight, at least about 0.4% by weight, or at least about 0.5% by weight, based on the total weight of the composition. In general, the silicone of component (b) may be present in the oily composition in an amount of about 50% by weight or less, particularly about 40% by weight or less, more specifically about 30% by weight or less, for example at about 28% by weight or less, about 27% by weight or less, about 26% by weight or less, or about 25% by weight or less, based on the total weight of the composition.

[0043] In embodiments, the silicone of component (b) may have a nitrogen content of about 0.05% to about 2% by weight, particularly about 0.06% to about 1.8% by weight, particularly about 0.07% to about 1.7% by weight, preferably about 0.1% to about 1.5% by weight, and more preferably about 0.2% to about 1% by weight.

[0044] In this embodiment, the silicone of component (b) may have a viscosity of about 2,000 mPas to about 50,000 mPas at 60°C, particularly about 2,500 mPas to about 45,000 mPas, more specifically about 3,000 mPas to about 40,000 mPas, for example, about 4,000 mPas to about 35,000 mPas, preferably 4,500 mPas to about 30,000 mPas, and more preferably 5,000 mPas to about 25,000 mPas. This viscosity may be measured using a viscometer TVE-25H from Toki Sangyo Co., Ltd.

[0045] In embodiments, components (a) and (b) may be present in weight ratios ranging from about 99.95:0.05 to about 50:50, particularly from about 99.9:0.1 to about 60:40, and more specifically from about 99.5:0.5 to about 70:30, for example, from about 99:1 to about 80:20.

[0046] In embodiments, the oily composition may optionally further contain hair conditioning and / or hair care ingredients, such as amino-functionalized silicones other than component (b) of the present invention or emollients conventionally known to condition hair. Examples of emollients include, but are not limited to, polyolefins, particularly petrolatum, paraffin oil, squalane, squalene, hydrogenated polyisobutene, hydrogenated polydecene, polybutene, and mixtures thereof. These additional hair conditioning and / or hair care ingredients are typically present in the oily composition in an amount of 10% by weight or less, particularly 5% by weight or less, more specifically 4% by weight or less, for example 3% by weight or less, for example 2% or 1% by weight, based on the total weight of the composition.

[0047] In some embodiments, the oily composition may have a viscosity at 25°C of about 0.01 mPas to about 1,000 mPas, particularly about 0.05 mPas to about 500 mPas, more specifically about 0.1 mPas to about 400 mPas, for example, about 0.5 mPas to about 300 mPas, preferably 1 mPas to about 200 mPas, and more preferably 2 mPas to about 100 mPas. This viscosity may be measured using a bismetron viscometer from Shibaura Systems Co., Ltd.

[0048] In specific embodiments, the composition consists essentially of component (a) and component (b), or comprises component (a) and component (b). In more specific embodiments, the composition consists essentially of component (a) and component (b), or comprises component (a) and component (b), in weight ratios of about 99.95:0.05 to about 50:50, particularly about 99.9:0.1 to about 60:40, and more specifically about 99.5:0.5 to about 70:30, for example, about 99:1 to about 80:20.

[0049] In another embodiment, the present invention relates to a method for preparing an oily composition, which optionally involves dispersing or dissolving component (b) in component (a) at a high temperature. In one embodiment, the amino-functionalized silicone of component (b) is added to and dispersed in the hydrocarbon oil of component (a) at ambient temperature. In another embodiment, component (b) is dissolved in component (a) at a high temperature. This high temperature may be in the range of about 30°C to about 90°C, about 40°C to about 80°C, about 40°C to about 70°C, or about 40°C to about 60°C. In a particular embodiment, component (b) is dissolved in component (a) at a slightly higher temperature of about 40°C to about 50°C. This dissolution or dispersion process may optionally be carried out under an inert gas, for example, in an argon atmosphere or a nitrogen atmosphere. After the dissolution or dispersion process is complete, an optional filtration process may be carried out to remove any undissolved component (b). In a specific embodiment, the resulting composition is a clear liquid. The concentration of component (b) in the obtained liquid may be measured after drying the liquid, for example, in an oven at 150°C for 1 hour.

[0050] In yet another embodiment, the present invention relates to a formulation for conditioning hair, comprising an oily composition containing an oily solvent component (a) and an amino-functionalized silicone having general formula (I) (b) dissolved or dispersed in the solvent.

[0051] In one embodiment, the hair formulation may be a leave-on hair product. In another embodiment, the hair conditioning formulation may be a rinse-off hair product. Descriptive examples of leave-on hair products include, but are not limited to, hair oils, hair serums, hair essences, hair emulsions, and others. Descriptive examples of rinse-off hair products include, but are not limited to, shampoos, hair conditioners, hair treatments, hair masks, and others. Further descriptive examples of leave-on hair products include, but are not limited to, hair repair agents, hair care agents, and others.

[0052] In one preferred embodiment of the present invention, the hair conditioning formulation is a hair oil, particularly a hair tail oil. In exemplary embodiments, the hair oil, particularly the hair tail oil, may further comprise a silicone oil selected from dimethicone oil, dimethicone gum, dimethiconol oil, dimethiconol gum, and phenyl silicone oil; an ester oil selected from caprylic / capric triglyceride, isononyl isononanoate, isopropyl myristate, and alkyl C12-15 benzoate; a vegetable oil selected from olive oil, jojoba oil, sunflower oil, argan oil, castor oil, coconut oil, almond oil, and avocado oil; a hydrocarbon selected from isododecane, isohexadecane, C9-12 alkanes, C13-16 isoalkanes, and hydrogenated polyisobutene; a mineral oil; a synthetic oil; and combinations thereof.

[0053] In a further embodiment, the present invention relates to a method for conditioning hair, which includes applying a formulation containing an oily composition to the hair. In a particular embodiment, the formulation containing an oily composition is applied to damaged hair, and the damaged hair after conditioning shows recovery and exhibits overall sensory benefits such as flexibility, smoothness of dry hair without stickiness or oiliness, moisture in the hair, and manageability of the hair.

[0054] Examples The present invention will be described more specifically with reference to examples, but these examples should not be construed as limiting the scope of the invention. Furthermore, in the following description, unless otherwise specified, "parts" refers to "parts by weight". Viscosity was measured for the amino-functionalized silicones of Synthesis Examples 1 to 6 using a TVE-25H viscometer from Toki Sangyo Co., Ltd., and for the oily compositions of Examples 6 and 7 using a bismetron viscometer from Shibaura Systems Co., Ltd.

[0055] Synthesis example 1:M R D 650 D N 3.5 M R synthesis 928.4 grams of octamethylcyclotetrasiloxane (D4), 11.7 grams of hydrolysate of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane having the general formula CH3O[Si(CH3)(CH2CH2CH2NHCH2CH2NH2)O]7CH3, 10.5 grams of hydroxy-terminated polydimethylsiloxane having the general formula HO[Si(CH3)2O]7H, and 68.6 grams of general formula R[Si(CH3)2O] 20 A C30-45 alkyl-terminated polydimethylsiloxane having R, where R is C30-45 alkyl, was added to a 2000 mL four-necked round-bottom flask under a nitrogen atmosphere. The flask was equipped with an overhead stirrer, a Liebig condenser, and a thermometer for monitoring the temperature. The mixture was heated to 90°C, followed by the addition of 90 ppm of tetramethylammonium silanolate catalyst. The equilibrium reaction was carried out over 6 hours while maintaining the temperature at 88 to 92°C. After the reaction was complete, the product was heated to 135 to 140°C to inactivate the catalyst. After 1 hour, the product was stripped while sparging with nitrogen at 15 to 25 Torre over 3 hours, leaving 782 grams of a translucent, grease-like product with 0.205 wt% nitrogen and a viscosity of 11,425 mPas at 60°C.

[0056] Synthesis example 2:M R D 650 D N 8.5 M R synthesis The procedure was the same as in Synthesis Example 1, except that 898.5 grams of D4, 28.0 grams of hydrolysate of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 25.0 grams of hydroxy-terminated polydimethylsiloxane, and 69.9 grams of C30-45 alkyl-terminated polydimethylsiloxane were used. 836 grams of a translucent, grease-like product with a viscosity of 9,950 mPas at 60°C and containing 0.508 wt% nitrogen was obtained.

[0057] Synthesis example 3:M R D 300 D N 4.1M R synthesis The procedure was the same as in Synthesis Example 1, except that 843.2 grams of D4, 28.5 grams of hydrolysate of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 25.6 grams of hydroxy-terminated polydimethylsiloxane, and 136.9 grams of C30-45 alkyl-terminated polydimethylsiloxane were used. 838 grams of a translucent, grease-like product with 0.507 wt% nitrogen and a viscosity of 3,500 mPas at 60°C was obtained.

[0058] Synthesis example 4:M R D 900 D N 11.6 M R synthesis The procedure was the same as in Synthesis Example 1, except that 912.2 grams of D4, 27.7 grams of hydrolysate of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 24.8 grams of hydroxy-terminated polydimethylsiloxane, and 47.0 grams of C30-45 alkyl-terminated polydimethylsiloxane were used. 812 grams of a translucent, grease-like product with a viscosity of 29,250 mPas at 60°C and 0.507 wt% nitrogen was obtained.

[0059] Synthesis example 5:M R D 650 D N 12.5 M R synthesis The procedure was the same as in Synthesis Example 1, except that 875.2 grams of D4, 40.6 grams of hydrolysate of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 36.3 grams of hydroxy-terminated polydimethylsiloxane, and 63.8 grams of C30-45 alkyl-terminated polydimethylsiloxane were used. 820 grams of a translucent, grease-like product with a viscosity of 8,500 mPas at 60°C and containing 0.735 wt% nitrogen was obtained.

[0060] Synthesis example 6:M R D 650 D N17.5 M R synthesis The procedure was the same as in Synthesis Example 1, except that 849.8 grams of D4, 54.4 grams of hydrolysate of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 48.7 grams of hydroxy-terminated polydimethylsiloxane, and 65.8 grams of C30-45 alkyl-terminated polydimethylsiloxane were used. 833 grams of a translucent, grease-like product with a viscosity of 6,625 mPas at 0.998 wt% nitrogen and 60°C was obtained.

[0061] evaluation The silicones synthesized as described above in Synthesis Examples 2, 4, 5, and 6 were dissolved in isododecane (IDD) or C9-12 alkane to obtain clear liquids containing 1% by weight of silicone, which are provided as Examples 1 to 5, as shown in Table 1-1. The obtained compositions were evaluated below for hair restoration and sensory testing. Comparative compositions listed in Table 1-2, which either contain no silicone or 1% by weight of silicone, were used for comparison.

[0062] [Table 1-1]

[0063] [Table 1-2] Silsoft AX:INCI name is bis-cetearyl amodimethicone, a C16-18 alkyl-terminated polydimethylsiloxane functionalized with an N-(2-aminoethyl)-3-aminopropyl group on the pendant, with a viscosity of ~10,000 mPas and a nitrogen content of 0.2 wt% at 25°C, and is obtained from Momentive Performance Materials. Amodimethicone: A trimethylsilyl-terminated polydimethylsiloxane functionalized with the N-(2-aminoethyl)-3-aminopropyl group of the pendant, having a viscosity of ~1,000 mPas and a nitrogen content of 0.9 wt% at 25°C, obtained from Momentive Performance Materials. PDMS is a polydimethylsiloxane oil with a viscosity of 10 cps at 25°C, obtained from Momentive Performance Materials. *: Indicates an aqueous emulsion; others are not emulsified.

[0064] Hair Restoration Test A 1.5 g of each tested composition was uniformly applied to moderately damaged Asian hair strands (obtained from Shanghai Tsangyu Trading Co.), and then dried at 22°C and 44% humidity for 5 hours. After the hair strands were dry, they were pulled taut and secured on both sides. Next, a predetermined amount (80 μL) of water was sprayed onto the surface of the hair strands. The time until the water droplets on the hair surface completely disappeared was recorded. This test was performed twice. The average values ​​are shown in Table 2 and Figure 1.

[0065] [Table 2]

[0066] The compositions of Examples 1-4 all required a longer time for water to disappear from the surface of damaged hair, indicating high lipophilicity and therefore good hair recovery.

[0067] Hair Restoration Test B 0.3g of each tested composition was applied uniformly to a severely damaged hair strand (obtained from Shanghai Tsangyu Trading Co.). After drying the hair strand, it was stretched and secured on both sides. Next, one drop of water was placed on the surface of the hair strand. The time it took for the water to completely disappear from the hair surface was recorded. This test was performed three times. The average values ​​are shown in Table 3.

[0068] [Table 3]

[0069] The time recorded for the composition of Example 1 was 6% longer than that for the composition of Comparative Example 5. This result is surprising, as PDMS oil is generally thought to adhere to the hair surface and form a film, and is expected to provide a better restorative effect. However, especially considering that IDD alone has no restorative effect and only 1% by weight of amino-functionalized silicone is used, the inventors have surprisingly found that IDD provides a better hair restorative effect than PDMS oil as a solvent for incorporating amino-functionalized silicone.

[0070] Hair Sensory Test A 1.5 g of each tested composition was evenly applied to moderately damaged Asian hair strands, which were then dried at 23°C and 41% humidity for 5 hours. After the hair strands were dry, two panelists evaluated the smoothness, flexibility, moisture, and manageability of the hair on a scale of 1 to 5. The average scores of these two panelists are shown in Table 4.

[0071] [Table 4]

[0072] Figure 2 shows hair traces treated with different compositions, where the trace on the left represents Example 1, the trace in the middle represents Comparative Example 2, and the trace on the right represents Comparative Example 4.

[0073] The compositions of Examples 1 and 5 showed improved smoothness, moisture, and ease of handling compared to the compositions of Comparative Examples 2 and 4. Although their flexibility was slightly lower than that of the comparative examples, it was still perfectly adequate for practical use.

[0074] Hair Sensory Test B 1.5 g each of the compositions from Example 1 and Comparative Example 5 were uniformly applied to moderately damaged Asian hair strands, which were then dried at 23°C and 41% humidity for 5 hours. After the hair strands were dry, two panelists evaluated the smoothness, flexibility, moisture, manageability, non-greasy feel, and non-stickiness of the hair on a scale of 1 to 5.

[0075] The average scores for these two compositions are shown in Figure 3 as a sensory diagram. In Figure 3, "IDD" represents Example 1 and "10cs" represents Comparative Example 5. Figure 4 shows hair traces treated with the two compositions, where the trace on the left represents Example 1 and the trace on the right represents Comparative Example 5.

[0076] These results demonstrate that amino-functionalized silicones formulated with IDD can provide excellent conditioning benefits without negative functionalities. In contrast, using PDMS oil as a solvent results in a slightly better manageability of the hair, but an unacceptably oily and sticky feel.

[0077] In hair sensory tests A and B, a high score indicates good sensory attributes, i.e.: "Excellent": 5 points "Good": 4 points "Normal": 3 points "Slightly inferior": 2 points "Bad": 1 point

[0078] Example 6: M in isododecane R D 650 D N 8.5 M R Preparation of concentrated solution 200 grams of Synthesis Example 2 and 800 grams of isododecane were placed in a 2000 mL four-necked round-bottom flask under a nitrogen atmosphere. This flask was equipped with an overhead stirrer, a Liebig condenser, and a thermometer for monitoring the temperature. The mixture was heated to 40 to 50°C and then stirred for 2 hours to completely dissolve the silicone polymer in isododecane. After cooling the product to ambient temperature, it was filtered through Celite, leaving 876 grams of a clear liquid with 0.097 wt% nitrogen and a viscosity of 19.8 mPas at 25°C. After filtration, 2 grams of the obtained liquid were weighed onto an aluminum plate and placed in an oven at 150°C for 1 hour to measure the solids content. The obtained solids content was 19.8%.

[0079] Example 7: M in C9-12 alkanes R D 650 D N 8.5 M R Preparation of concentrated solution The procedure was the same as in Example 6, except that 800 grams of C9-12 alkane were used instead of isododecane. 883 grams of a clear liquid with 0.095 wt% nitrogen and a viscosity of 17.0 mPas at 25°C was obtained. After filtration, 2 grams of the obtained liquid were weighed onto an aluminum plate and placed in a 150°C oven for 1 hour to measure the solid content. The obtained solid content was 19.7%.

[0080] Example 8: Hair oil conditioner formulation and hair sensory test Three hair oil formulations were prepared using the ingredients listed in Table 5. Six panelists tested each formulation on their own hair and evaluated each sensory attribute using a rating scale from 1 to 10. The average ratings of the six panelists are shown in Table 5.

[0081] [Table 5]

[0082] Example 9: Hair rinse-off conditioner formulation and hair sensory test Three hair rinse-off conditioner formulations were prepared using the ingredients listed in Table 6. Six panelists tested each formulation on their own hair and evaluated each sensory attribute using a rating scale from 1 to 10. The average ratings of the six panelists are shown in Table 6 and Figure 5.

[0083] [Table 6]

[0084] process All components in parts A and B were mixed at 80°C until homogeneous. Part B was added to Part A while being mixed. The mixture was mixed for 20 minutes, then cooled to 40°C. Part C was added one by one and mixed until uniform.

[0085] The resulting formulation remained stable for at least 3 months at 5°C, room temperature, 40°C, and 50°C.

[0086] Example 9 demonstrated excellent properties in all attributes, particularly in terms of improved flexible feel during application and rinse-off when wet and dry.

[0087] Example 10: Shampoo formulation and hair sensory test These shampoo formulations were prepared using the ingredients listed in Table 7. Six panelists tested each formulation on their own hair and evaluated each sensory attribute using a rating scale from 1 to 10. The average ratings of the six panelists are shown in Table 8 and Figure 6.

[0088] [Table 7]

[0089] process Mix all components in phase A until uniform. 75 rpm. Phase B is heated and mixed until uniform, then added to the other phase and mixed uniformly. Add the component in phase C and mix uniformly (5 minutes, 250 rpm). Phase D is added to phases A, B, and C, and then the mixture is heated to 70°C. Phase E is heated to 70°C until melted, then added to phases A / B / C / D and mixed uniformly. Cool to 40°C. Add phase F one by one and mix until uniform. Adjust the viscosity with phase G and mix uniformly.

[0090] The resulting formulation remained stable for at least 3 months at 5°C, room temperature, 40°C, and 50°C.

[0091] [Table 8]

[0092] In Examples 8 to 10, regarding the hair sensory evaluation, a high score indicates good sensory attributes, i.e.: "Excellent": 10 points "Good": 8 points "Normal": 5 points "Slightly inferior": 3 points "Bad": 1 point

[0093] While this disclosure has been described in relation to preferred embodiments, it will be understood by those skilled in the art that various modifications may be made and equivalents may be substituted for their elements without departing from the scope of this disclosure. In addition, many modifications may be made to the teachings of this disclosure to suit specific circumstances or materials without departing from the essential scope of this disclosure. Thus, this disclosure is intended to include all embodiments that are covered within the appended claims, rather than being limited to specific embodiments disclosed as the best mode considered for carrying out this disclosure.

Claims

1. An oily composition: (a) an oily solvent selected from hydrocarbon oils; and (b) comprising a silicone having general formula (I) that is dissolved or dispersed in an oily solvent: M １ D １ ｘ D ２ ｙ M ２ (I) During the ceremony, M １ =R １ R ２ R ３ SiO ０.５ M ２ =R ４ R ５ R ６ SiO ０.５ D １ =SiR ７ R ８ O D ２ =SiR ９ R １０ O Here R １ , R ２ , R ４ , R ５ , R ７ , R ８ and R ９ Each is independently selected from a monovalent hydrocarbon group having approximately 1 to approximately 6 carbon atoms; R ３ and R ６ Each is independently selected from alkyl groups having approximately 20 to approximately 60 carbon atoms; Each R １０ These are independently selected from the 3-aminopropyl group and the N-(2-aminoethyl)-3-aminopropyl group; An oily composition in which the subscript x has a value of approximately 1 to approximately 2,000, and the subscript y has a value of approximately 1 to approximately 50.

2. The oily composition according to claim 1, wherein the composition is not emulsified.

3. The oily composition of claim 1 or 2, wherein the hydrocarbon oil is selected from linear or branched hydrocarbon oils having about 8 to about 20 carbon atoms, preferably about 9 to about 16 carbon atoms, and more preferably about 9 to about 14 carbon atoms.

4. An oily composition according to any one of claims 1 to 3, wherein the hydrocarbon oil is from a linear or branched alkane oil having about 8 to about 16 carbon atoms; preferably from linear or branched octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, cetane, or a mixture thereof; and more preferably selected from linear or branched nonane, decane, undecane, dodecane, or a mixture thereof.

5. R １ , R ２ , R ４ , R ５ , R ７ , R ８ and R ９ An oily composition of any one of claims 1 to 4, wherein each is independently selected from an alkyl group having about 1 to about 6 carbon atoms, preferably from an alkyl group having about 1 to about 4 carbon atoms, and more preferably from a methyl group.

6. R ３ and R ６ An oily composition of any one of claims 1 to 5, wherein each is independently selected from alkyl groups having about 24 to about 54 carbon atoms, preferably about 30 to about 50 carbon atoms, and more preferably about 35 to about 45 carbon atoms.

7. R １０ An oily composition according to any one of claims 1 to 6, wherein is an N-(2-aminoethyl)-3-aminopropyl group.

8. An oily composition according to any one of claims 1 to 7, wherein the subscript x has a value of approximately 100 to approximately 1,500, preferably approximately 200 to approximately 1,000, and more preferably approximately 300 to approximately 1,000; and the subscript y has a value of approximately 1.5 to approximately 40, preferably approximately 2 to approximately 30, and more preferably approximately 3 to approximately 20.

9. An oily composition according to any one of claims 1 to 8, wherein the silicone has a nitrogen content of about 0.05% to about 2% by weight, preferably about 0.1% to about 1.5% by weight, and more preferably about 0.2% to about 1% by weight.

10. An oily composition according to any one of claims 1 to 9, wherein component (a) and component (b) are present in a weight ratio of about 99.95:0.05 to about 50:50, preferably about 99.9:0.1 to about 60:40, and more preferably 99.5:0.5 to about 70:

30.

11. An oily composition according to any one of claims 1 to 10, wherein the composition essentially consists of component (a) and component (b), or consists of component (a) and component (b).

12. A method for preparing any one of claims 1 to 11, comprising optionally dispersing or dissolving component (b) in component (a) at a high temperature.

13. A formulation for conditioning hair, comprising any one of the oily compositions from claims 1 to 11 or an oily composition prepared by the method of claim 12.

14. Leave-on hair products and rinse-off hair products; preferably hair oils, hair serums, hair essences, hair emulsions, shampoos, hair conditioners, hair repair agents, hair care agents, hair treatment agents, or hair masks; the formulation of claim 13, particularly selected from hair tail oils.

15. A method for conditioning hair, comprising applying the formulation of claim 13 or 14 to the hair.

16. An oily composition comprising essentially (a) and (b), or comprising (a) and (b): (a) an oily solvent selected from polydimethylsiloxane having a viscosity of 9 cps or less at 25°C and cyclic siloxane having 10 or fewer silicon atoms, particularly selected from polydimethylsiloxane having a viscosity of 8 cps or less at 25°C and cyclic siloxane having 6 or fewer silicon atoms, and more specifically polydimethylsiloxane having a viscosity of 5 cps or less at 25°C, and selected from cyclotetrasiloxane, cyclopentasiloxane, and cyclohexasiloxane; and (b) Silicones that are dissolved or dispersed in an oily solvent and have general formula (I): M １ D １ ｘ D ２ ｙ M ２ (I) During the ceremony, M １ =R １ R ２ R ３ SiO ０.５ M ２ =R ４ R ５ R ６ SiO ０.５ D １ =SiR ７ R ８ O D ２ =SiR ９ R １０ O Here R １ , R ２ , R ４ , R ５ , R ７ , R ８ and R ９ Each is independently selected from a monovalent hydrocarbon group having approximately 1 to approximately 6 carbon atoms; R ３ and R ６ Each is independently selected from alkyl groups having approximately 20 to approximately 60 carbon atoms; Each R １０ These are independently selected from the 3-aminopropyl group and the N-(2-aminoethyl)-3-aminopropyl group; An oily composition in which the subscript x has a value of approximately 1 to approximately 2,000, and the subscript y has a value of approximately 1 to approximately 50.

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