Oil-based compositions and hair conditioning formulations containing same

Abstract

The present invention relates to an oil-based composition containing an oil-based solvent selected from hydrocarbon oils and an alkyl-terminated amino-functionalized silicone dissolved or dispersed in the oil-based solvent, as well as a process for its preparation. The invention also relates to a hair conditioning formulation containing the oil-based composition and a method of conditioning hair using the formulation.

Description

Technical Field

[0001] This invention relates to oil-based compositions comprising an oil-based solvent selected from hydrocarbon oils and an alkyl-terminated amino-functionalized organosilicon dissolved or dispersed in the oil-based solvent, and methods for preparing the same. This invention also relates to hair conditioning formulations containing oil-based compositions and methods for conditioning hair using the formulations. Background Technology

[0002] Hair typically has a thin, lipophilic membrane on its cuticle for protection. When hair suffers dryness and / or damage due to the environment, styling, regular cleaning, drying, and chemical treatments such as dyeing and perming, the lipophilic substance in the membrane is significantly reduced. As a result, the hair will appear dull, feel less smooth, and become brittle and prone to breakage.

[0003] Various methods are known in the art for conditioning and restoring such damaged hair. One common method is the use of hair care compositions containing a conditioning agent (such as functionalized silicone). In particular, amino-functionalized silicone is used to deliver beneficial conditioning effects to the hair, such as lubrication of the hair surface and restoration of the lipophilicity of the hair cuticle.

[0004] Amino-functionalized silicones in grease form are typically emulsified in water or dispersed in low-viscosity silicone oils (polydimethylsiloxane oils) to form emulsions for easy storage and transport. There remains a need for compositions of such amino-functionalized silicones that are stable over long periods and provide overall improved conditioning benefits. The compositions are expected to provide sensory benefits such as softness, smoothness after drying without a sticky or greasy feel, hair moisturizing properties, hair manageability, and combability. The compositions are highly expected to provide excellent restorative effects on hair damaged by natural, environmental, and chemical hair treatments. Summary of the Invention

[0005] In one aspect, the present invention relates to an oil-based composition comprising:

[0006] (a) an oil-based solvent selected from hydrocarbon oils; and

[0007] (b) Organosilicones dissolved or dispersed in oil-based solvents and having the general formula (I):

[0008] M 1 D 1 x D 2 y M 2 (I)

[0009] in

[0010] M 1 =R 1 R 2 R 3 SiO 0.5

[0011] M 2 =R 4 R 5 R 6 SiO 0.5

[0012] D 1 =SiR 7 R 8 O

[0013] D 2 =SiR 9 R 10 O

[0014] in

[0015] R 1 R 2 R 4 R 5 R 7 R 8 and R 9 Each is independently selected from monovalent hydrocarbon groups having approximately 1 to approximately 6 carbon atoms;

[0016] R 3 and R 6 Each is independently selected from alkyl groups having about 20 to about 60 carbon atoms;

[0017] Each R 10 Independently selected from 3-aminopropyl and N-(2-aminoethyl)-3-aminopropyl;

[0018] 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.

[0019] In another aspect, the present invention relates to a method for preparing an oil-based composition, comprising optionally dispersing or dissolving component (b) in component (a) at an elevated temperature.

[0020] In another aspect, the present invention relates to formulations for conditioning hair, comprising the oil-based composition of the present invention.

[0021] In another aspect, the present invention relates to a method of conditioning hair, comprising applying a formulation comprising an oil-based composition to hair.

[0022] The oil-based compositions of the present invention provide effective restoration for damaged hair while exhibiting overall sensory benefits, including softness, smoothness of dry hair without stickiness or greasiness, hair moisturizing, and hair manageability. Attached Figure Description

[0023] Figure 1 The bar chart shows the hair restoration test A results for various compositions.

[0024] Figure 2 Showing hair strands treated with the compositions of Example 1, Comparative Example 2, and Comparative Example 4.

[0025] Figure 3 Sensory images of the compositions of Example 1 and Comparative Example 5 are shown.

[0026] Figure 4 The illustration shows hair strands treated with the compositions of Example 1 and Comparative Example 5.

[0027] Figure 5 Sensory images of the hair-washing conditioner formulation of Example 9 are shown.

[0028] Figure 6 Sensory images of the shampoo formulation of Example 10 are shown. Detailed Implementation Plan

[0029] In the specification and claims herein, the following terms and expressions shall be understood as indicated.

[0030] The singular forms “a” and “the” include the plural, and references to a particular numerical value include at least that particular value, unless the context clearly specifies otherwise.

[0031] Unless otherwise stated herein or there is an obvious contradiction in the context, all methods described herein may be performed in any suitable order. Unless otherwise stated, the use of any and all embodiments (examples) or exemplary language (such as "such as") provided herein is intended only to better illustrate the invention and does not constitute a limitation on the scope of the invention.

[0032] No language in this specification should be construed as indicating that any unclaimed element is essential to the practice of this invention.

[0033] The terms “comprising,” “including,” “containing,” and their grammatical equivalents are inclusive or open-ended terms that do not exclude additional, unlisted elements or methodological steps, but will also be understood to include the more restrictive terms “consisting of” and “substantially consisting of”.

[0034] Unless otherwise indicated in the working examples (examples) or otherwise, all figures set forth in the specification and claims representing the amount of material, temperature, duration of time, quantitative properties of the material, etc., shall in all cases be understood to be modified by the term “about”, regardless of whether the term “about” is used in the description.

[0035] It should be understood that any numerical range in this article includes all subranges within the range and any combination of the various endpoints of these ranges or subranges.

[0036] It will be further understood that any compound, material, or substance that is explicitly or implicitly disclosed in the specification and / or recited in the claims as belonging to a group of compounds, materials, or substances that are structurally, compositionally, and / or functionally related includes a single representative of the group and all combinations thereof.

[0037] The term "hydrocarbon group" refers to any hydrocarbon from which one or more hydrogen atoms have been removed, and includes alkyl, alkenyl, ynyl, cycloalkyl, cycloalkenyl, cycloynyl and phenyl groups, and includes hydrocarbon groups containing at least one heteroatom.

[0038] The term "alkyl" refers to any monovalent, saturated straight-chain, branched, or cyclic hydrocarbon group; the term "alkenyl" refers to any monovalent straight-chain, branched, or cyclic hydrocarbon group containing one or more carbon-carbon double bonds, wherein the group's linkage site may be at a carbon-carbon double bond or at other positions therein; and the term "alkynyl" refers to any monovalent straight-chain, branched, or cyclic hydrocarbon group containing one or more carbon-carbon triple bonds and optionally one or more carbon-carbon double bonds, wherein the group's linkage site may be at a carbon-carbon triple bond, a carbon-carbon double bond, or at other positions therein.

[0039] The terms “cycloalkyl,” “cycloalkenyl,” and “cycloalkynyl” include bicyclic, tricyclic, and higher cyclic structures, as well as the aforementioned cyclic structures further substituted with alkyl, alkenyl, and / or alkynyl groups.

[0040] The term "heteroatom" refers to any element in Groups 13-17 other than carbon, and includes, for example, oxygen, nitrogen, silicon, sulfur, phosphorus, fluorine, chlorine, bromine, and iodine.

[0041] 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; and hexyl groups such as n-hexyl. Examples of alkenyl groups include vinyl, propenyl, allyl, methanalyl, and cyclohexenyl. Examples of alkynyl groups include ethynyl, propynyl, and methylethynyl.

[0042] As used herein, the term "oil-based composition" should be understood to mean an emulsified or non-emulsified, preferably non-emulsified, composition of a plurality of substances formulated for hair care and / or conditioning purposes, wherein the oil-based solvent is the continuous phase. The 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 herein, the term "oil-based solvent" should be understood to include any lipophilic or hydrophobic non-aqueous solvent that is liquid at room temperature (25°C) and atmospheric pressure (760 mm Hg).

[0043] As used in this article, the term "hydrocarbon oil" refers to oil that is primarily composed of hydrogen and carbon atoms or is composed of hydrogen and carbon atoms.

[0044] The terms or words used in the specification and claims should not be construed as having their ordinary or dictionary meanings, but should be interpreted as meanings and concepts consistent with the inventive concept, based on the principle that the inventor can appropriately define the terms and concepts to best interpret his or her invention.

[0045] In one aspect, the present invention relates to an oil-based composition comprising:

[0046] (a) an oil-based solvent selected from hydrocarbon oils; and

[0047] (b) Polysiloxanes having the general formula (I) that are dissolved or dispersed in an oil-based solvent:

[0048] M 1 D 1 x D 2 y M 2 (I)

[0049] in

[0050] M 1 =R 1 R 2 R 3 SiO 0.5

[0051] M 2 =R 4 R 5 R 6 SiO 0.5

[0052] D 1 =SiR 7 R 8 O

[0053] D 2 =SiR 9 R 10 O

[0054] in

[0055] R 1 R 2 R 4 R 5 R 7 R 8 and R 9 Each is independently selected from monovalent hydrocarbon groups having approximately 1 to approximately 6 carbon atoms;

[0056] R 3 and R 6 Each is independently selected from alkyl groups having about 20 to about 60 carbon atoms;

[0057] Each R 10 Independently selected from 3-aminopropyl and N-(2-aminoethyl)-3-aminopropyl;

[0058] 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.

[0059] The oil-based compositions of the present invention may be non-emulsified or emulsified. When the composition is emulsified, a surfactant and / or water may be added. As surfactants, any of anionic, cationic, nonionic, and amphoteric surfactants may be used, and they may be used alone or as a mixture of two or more. In a preferred embodiment, the oil-based composition is non-emulsified. In a preferred embodiment, the oil-based composition is substantially free of or contains no surfactant. Preferably, the composition contains 2% by weight or less, particularly 1.5% by weight or less, more particularly 1% by weight or less of a surfactant. When the non-emulsified composition is incorporated into oil-based conditioning products such as hair oil, especially hair tail oil, the non-emulsified composition provides excellent hair conditioning and restorative effects.

[0060] In one embodiment, the hydrocarbon oil (a) is selected from straight-chain or branched hydrocarbon oils having about 8 to about 20 carbon atoms, particularly about 8 to about 19 carbon atoms, more particularly 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 a specific embodiment, the hydrocarbon oil is selected from straight-chain or branched alkane oils having about 8 to about 16 carbon atoms; preferably straight-chain or branched octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, or mixtures thereof; and more preferably straight-chain or branched nonane, decane, undecane, dodecane, or mixtures thereof. In one specific embodiment, the hydrocarbon oil is isododecane. In another specific embodiment, the hydrocarbon oil is a C9-12 alkane. These hydrocarbon oils can be used alone or in combination of two or more of them.

[0061] When hydrocarbon oils, particularly alkane oils having 9 to 12 carbon atoms such as isododecane, are used as solvents to formulate the amino-functionalized organosilicon component (b), the formulated compositions offer improved hair restoration and improved sensory properties without oiliness or stickiness compared to lower viscosity silicone oils conventionally used as solvents for functionalized organosilicon, due to their compatibility. The hydrocarbon oils allow the active component (b) of the amino-functionalized organosilicon to be present in the oil-based composition at a concentration of up to about 50% by weight (e.g., up to about 40%, 30%, or 20% by weight, based on the total weight of the composition), while the resulting composition remains stable. The oil-based compositions remain compatible with various types of formulations used to treat or condition hair, including those based on organic oils, as well as those based on silicone oils or aqueous emulsions.

[0062] Based on the total weight of the composition, the hydrocarbon oil (a) may be present in the oil-based composition in an amount of at least about 50% by weight, particularly at least about 55% by weight, more particularly 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. Typically, based on the total weight of the composition, the hydrocarbon oil (a) may be present in the oil-based composition in an amount of no more than about 99.99% by weight, particularly no more than about 99.95% by weight, more particularly no more than about 99.9% by weight, for example no more than about 99.5% by weight, no more than about 99% by weight, no more than about 98% by weight, or no more than about 97% by weight.

[0063] In the implementation scheme, 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 monovalent hydrocarbon groups having about 1 to about 6 carbon atoms, which may be unsubstituted or substituted with halogen atoms, for example, selected from 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 phenyl or alkyl groups having about 1 to about 6 carbon atoms. Preferably, R 1 R 2 R 4 R 5 R 7 R 8 and R9 Each is independently selected from: alkyl groups having about 1 to about 4 carbon atoms; particularly, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and isobutyl; and more particularly, methyl.

[0064] In formula (I) of component (b), R 3 and R 6 Each is independently selected from straight-chain or branched alkyl groups having about 20 to about 60 carbon atoms, particularly about 24 to about 54 carbon atoms or about 51 to about 60 carbon atoms, more particularly about 30 to about 50 carbon atoms, and preferably about 35 to about 45 carbon atoms, for example about 35, 36, 37, 38, 39, 40, 41, 42, 43, 44 or 45 carbon atoms.

[0065] In formula (I) of component (b), R 10 Independently selected from 3-aminopropyl and N-(2-aminoethyl)-3-aminopropyl. In one embodiment, R 10 It is N-(2-aminoethyl)-3-aminopropyl.

[0066] In one specific embodiment of component (b), R 1 R 2 R 4 R 5 R 7 R 8 and R 9 Methyl; R 3 and R 6 Each is independently an alkyl group having a straight chain or branched chain having about 35 to about 45 carbon atoms; and R 10 It is N-(2-aminoethyl)-3-aminopropyl.

[0067] In formula (I) of component (b), x has values ​​from about 100 to about 1,500, particularly from about 200 to about 1,000, more particularly from about 300 to about 1,000, 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 values ​​from about 1.5 to about 40, specifically from about 2 to about 30, and more particularly 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 one embodiment, x is about 650 and y is about 3.5. In another embodiment, x is about 650 and y is about 8.5.

[0068] In the embodiments, based on the total weight of the composition, the silicone of component (b) may be present in the oil-based composition in an amount of at least about 0.05% by weight, particularly at least about 0.08% by weight, more particularly 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. Typically, based on the total weight of the composition, the silicone of component (b) may be present in the oil-based composition in an amount of no more than about 50% by weight, particularly no more than about 40% by weight, more particularly no more than about 30% by weight, for example no more than about 28% by weight, no more than about 27% by weight, no more than about 26% by weight, or no more than about 25% by weight.

[0069] In the embodiments, the organosilicon of component (b) may have a nitrogen content of about 0.05% to about 2% by weight, specifically about 0.06% to about 1.8% by weight, specifically 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.

[0070] In the embodiments, the organosilicon of component (b) may have a viscosity at 60°C ranging from about 2,000 mPa·s to about 50,000 mPa·s, particularly from about 2,500 mPa·s to about 45,000 mPa·s, more particularly from about 3,000 mPa·s to about 40,000 mPa·s, for example from about 4,000 mPa·s to about 35,000 mPa·s, preferably from 4,500 mPa·s to about 30,000 mPa·s, and more preferably from 5,000 mPa·s to about 25,000 mPa·s. The viscosity can be measured by a VISCOMETER TVE-25H from TOKI SANGYO Co., Ltd.

[0071] In the embodiments, components (a) and components (b) may be present in a weight ratio of about 99.95:0.05 to about 50:50, particularly about 99.9:0.1 to about 60:40, and more particularly about 99.5:0.5 to about 70:30, for example about 99:1 to about 80:20.

[0072] In embodiments, the oil-based composition may optionally further comprise hair conditioning and / or conditioning ingredients, such as amino-functionalized silicones different from component (b) of the present invention or emollients generally known for conditioning hair. Examples of emollients include, but are not limited to, polyolefins, especially petrolatum (petrolatum), paraffin oil, squalane, squalene, hydrogenated polyisobutylene, hydrogenated polydecene, polybutene, and mixtures thereof. Based on the total weight of the composition, these additional hair conditioning and / or conditioning ingredients are generally present in the oil-based composition in amounts not exceeding 10% by weight, particularly not exceeding 5% by weight, more particularly not exceeding 4% by weight, for example not exceeding 3% by weight, such as 2% by weight or 1% by weight.

[0073] In embodiments, the oil-based composition may have a viscosity at 25°C of about 0.01 mPa·s to about 1,000 mPa·s, particularly about 0.05 mPa·s to about 500 mPa·s, more particularly about 0.1 mPa·s to about 400 mPa·s, for example about 0.5 mPa·s to about 300 mPa·s, preferably 1 mPa·s to about 200 mPa·s, more preferably 2 mPa·s to about 100 mPa·s. The viscosity can be measured using a VISMETRON VISCOMETER from SHIBAURA SEMETEC Co., Ltd.

[0074] In a specific embodiment, the composition is substantially composed of or consists of component (a) and component (b). In a more specific embodiment, the composition is substantially composed of or consists of component (a) and component (b) in a weight ratio of about 99.95:0.05 to about 50:50, particularly about 99.9:0.1 to about 60:40, and more particularly about 99.5:0.5 to about 70:30, for example about 99:1 to about 80:20.

[0075] In another aspect, the present invention relates to a method for preparing an oil-based composition, comprising: optionally dispersing or dissolving component (b) in component (a) at an elevated temperature. In one embodiment, the amino-functionalized organosilicon component (b) is added to and dispersed in the hydrocarbon oil component (a) at ambient temperature. In another embodiment, component (b) is dissolved in component (a) at an elevated temperature. The elevated temperature range may be from about 30°C to about 90°C, from about 40°C to about 80°C, from about 40°C to about 70°C, or from about 40°C to about 60°C. In a specific embodiment, component (b) is dissolved in component (a) at a slightly elevated temperature of about 40°C to about 50°C. The dissolution or dispersion process may optionally be carried out under an inert gas atmosphere such as argon or nitrogen. After the dissolution or dispersion process is completed, a filtration process may optionally be performed to remove undissolved component (b). In a specific embodiment, the resulting composition is a clear liquid. The concentration of component (b) in the resulting liquid can be measured after drying the liquid, for example, by heating it in an oven at 150°C for 1 hour.

[0076] In another aspect, the present invention relates to a formulation for conditioning hair, comprising an oil-based composition containing an oil-based solvent component (a) and an amino-functionalized organosilicon component (b) having general formula (I) dissolved or dispersed in a solvent.

[0077] In one embodiment, the hair preparation may be a leave-on hair product. In another embodiment, the hair conditioning preparation may be a rinsing-off hair product. Illustrative examples of leave-on hair products include, but are not limited to, hair oils, hair serums, hair essences, and hair lotions. Illustrative examples of rinsing-off hair products include, but are not limited to, shampoos, hair conditioners, hair treatments, and hair masks. Further illustrative examples of leave-on hair products include, but are not limited to, hair repair agents and hair conditioning agents.

[0078] In a preferred embodiment of the invention, the hair conditioning preparation is a hair oil, particularly a hair tip oil. In an illustrative embodiment, the hair oil, particularly the hair tip oil, may further comprise an organosilicon oil selected from dimethicone, dimethicone gum, dimethiconol oil, dimethiconol gum, and phenyl silicone oil; an ester oil selected from caprylic / capric triglyceride, isononyl isononanoate, isopropyl myristate, and C12-15 alkyl 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 polyisobutylene; mineral oil; synthetic oil; and combinations thereof.

[0079] In another aspect, the present invention relates to a method of conditioning hair, comprising applying a formulation comprising an oil-based composition to hair. In one specific embodiment, the formulation comprising an oil-based composition is applied to damaged hair, and the treated damaged hair exhibits restorative and overall sensory benefits, including softness, dry smoothness without stickiness or greasiness, hair hydration, and hair manageability.

[0080] Example

[0081] The invention will be explained in more detail with reference to the embodiments, but these embodiments should not be construed as limiting the scope of the invention. Furthermore, in the following description, unless otherwise stated, "parts" means "parts by weight". Viscosities were measured using a VISCOMETER TVE-25H from TOKI SANGYOCo., Ltd. for the amino-functionalized organosilicones of Examples 1 to 6, and by a VISMETRON VISCOMETER from SHIBAURA SEMETEC Co., Ltd. for the oil-based compositions of Examples 6 to 7.

[0082] Synthesis Example 1: M R D 650 D N 3.5 M R Synthesis

[0083] Under a nitrogen atmosphere, 928.4 g of octamethylcyclotetrasiloxane (D4), 11.7 g of the hydrolysis product of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane having the general formula CH3O[Si(CH3)(CH2CH2CH2NHCH2CH2NH2)O]7CH3, 10.5 g of hydroxyl-terminated polydimethylsiloxane having the general formula HO[Si(CH3)2O]7H, and 68.6 g of polydimethylsiloxane having the general formula R[Si(CH3)2O]7H were subjected to a nitrogen reaction. 20 C30-45 alkyl-terminated polydimethylsiloxane (R, where R is a C30-45 alkyl group) was added to a 2000 mL four-necked round-bottom flask. The flask was equipped with a top stirrer, a Dimroth condenser, and a thermometer for temperature monitoring. The mixture was heated to 90 °C, followed by the addition of 90 ppm of silanolized tetramethylammonium catalyst. The reaction was carried out at 88-92 °C for 6 hours to reach equilibrium. After the reaction was complete, the product was heated to 135-140 °C to deactivate the catalyst. After 1 hour, the product was stripped under nitrogen at 15-25 Torr for 3 hours to give 782 g of a translucent, oily product with 0.205 wt% nitrogen and a viscosity of 11,425 mPa·s at 60 °C.

[0084] Synthesis Example 2: M R D 650 D N 8.5 M R Synthesis

[0085] The procedure was similar to that of Synthesis Example 1, except that 898.5 g of D4, 28.0 g of the hydrolysis product of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 25.0 g of hydroxyl-terminated polydimethylsiloxane, and 69.9 g of C30-45 alkyl-terminated polydimethylsiloxane were used. 836 g of a translucent, oily product was obtained, having 0.508 wt% nitrogen and a viscosity of 9,950 mPa·s at 60 °C.

[0086] Synthesis Example 3: M R D 300 D N 4.1 M R Synthesis

[0087] The procedure was similar to that of Synthesis Example 1, except that 843.2 g of D4, 28.5 g of the hydrolysis product of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 25.6 g of hydroxyl-terminated polydimethylsiloxane, and 136.9 g of C30-45 alkyl-terminated polydimethylsiloxane were used. 838 g of a translucent, oily product was obtained, having 0.507 wt% nitrogen and a viscosity of 3,500 mPa·s at 60 °C.

[0088] Synthesis Example 4: M R D 900 D N 11.6 M R Synthesis

[0089] The procedure was similar to that of Synthesis Example 1, except that 912.2 g of D4, 27.7 g of the hydrolysis product of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 24.8 g of hydroxyl-terminated polydimethylsiloxane, and 47.0 g of C30-45 alkyl-terminated polydimethylsiloxane were used. 812 g of a translucent, oily product was obtained, having 0.507 wt% nitrogen and a viscosity of 29,250 mPa·s at 60 °C.

[0090] Synthesis Example 5: M R D 650 D N 12.5 M R Synthesis

[0091] The procedure was similar to that of Synthesis Example 1, except that 875.2 g of D4, 40.6 g of the hydrolysis product of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 36.3 g of hydroxyl-terminated polydimethylsiloxane, and 63.8 g of C30-45 alkyl-terminated polydimethylsiloxane were used. 820 g of a translucent, oily product was obtained, having 0.735 wt% nitrogen and a viscosity of 8,500 mPa·s at 60 °C.

[0092] Synthesis Example 6: M R D 650 D N 17.5 M R Synthesis

[0093] The procedure was similar to that of Synthesis Example 1, except that 849.8 g of D4, 54.4 g of the hydrolysis product of N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 48.7 g of hydroxyl-terminated polydimethylsiloxane, and 65.8 g of C30-45 alkyl-terminated polydimethylsiloxane were used. 833 g of a translucent, oily product was obtained, having 0.998 wt% nitrogen and a viscosity of 6,625 mPa·s at 60 °C.

[0094] evaluate

[0095] The organosilicones synthesized in Synthetic Examples 2, 4, 5, and 6 were dissolved in isododecane (IDD) or C9-12 alkanes to provide a clear liquid containing 1% by weight of organosilicon, as Examples 1 to 5 shown in Table 1-1, respectively. The hair restoration and sensory tests of the resulting compositions were evaluated below. Comparisons were made using the control compositions listed in Table 1-2, which were either organosilicon-free or contained 1% by weight of organosilicon.

[0096] Table 1-1 Compositions of the Invention (Oil-based and Non-emulsified)

[0097]

[0098] Table 1-2 Comparative Compositions

[0099]

[0100] Silsoft AX:INCI name is Bis-CetearylAmodimethicone, a C16-18 alkyl-terminated polydimethylsiloxane with side-linked N-(2-aminoethyl)-3-aminopropyl functionalization, having a viscosity of ~10,000 mPa·s and a nitrogen content of 0.2% by weight at 25°C, obtained from MomentivePerformance Materials Inc.

[0101] Ammonia-terminated polydimethylsiloxane: A polydimethylsiloxane with a trimethylsilyl group side-capped with N-(2-aminoethyl)-3-aminopropyl functionalization, having a viscosity of ~1,000 mPa·s and a nitrogen content of 0.9% by weight at 25 °C, obtained from Momentive Performance Materials Inc.

[0102] PDMS: Polydimethylsiloxane oil with a viscosity of 10 cps at 25°C, obtained from Momentive Performance Materials Inc.

[0103] * indicates an aqueous emulsion; the others are non-emulsified.

[0104] Hair recovery test A

[0105] 1.5 g of each test composition was uniformly applied to moderately damaged hair strands (obtained from Shanghai Canyu Commercial Ltd.) from Asian individuals, and then allowed to dry at 22°C and 44% humidity for 5 hours. After drying, the hair strands were pulled and secured at both ends. Next, a certain amount (80 μL) of water was sprayed onto the surface of the hair strands. The time it took for the water droplets on the surface of the hair strands to completely disappear was recorded. This test was performed in duplicate. The average values ​​are shown in Table 2 and... Figure 1 middle.

[0106] Table 2 Results of Hair Restoration Test A

[0107]

[0108] All compositions in Examples 1-4 exhibited longer water disappearance time on the surface of the damaged hair strand, indicating higher lipophilicity and thus better hair strand recovery.

[0109] Hair recovery test B

[0110] 0.3 g of each test composition was uniformly applied to highly damaged hair strands (obtained from Shanghai CanYu Commercial Co. Ltd.). After the hair strands dried, they were pulled and secured at both ends. Then, a drop of water was placed on the surface of the hair strand. The time it took for the water on the hair surface to completely disappear was recorded. This test was performed in triplicate. The average values ​​are shown in Table 3.

[0111] Table 3 Results of Hair Restoration Test B

[0112]

[0113] The composition of Example 1 recorded a 6% longer time than the composition of Comparative Example 5. This result was surprising, as PDMS oil is generally thought to deposit on the hair surface and form a film, and is expected to provide better restoration results. However, the inventors were surprised to find that IDD, as a solvent for formulating amino-functionalized silicone, provided better hair restoration than PDMS oil, especially considering that IDD alone had no restoration effect and that the amino-functionalized silicone was used at only 1% by weight.

[0114] Hair sensory test A

[0115] Each test composition (1.5 g) was uniformly applied to moderately damaged hair strands from Asian individuals and then allowed to dry at 23°C and 41% humidity for 5 hours. After drying, two members of a specialized panel rated the sensory attributes of hair smoothness, softness, moisture retention, and manageability on a scale of 1 to 5. The average scores from the two panel members are shown in Table 4.

[0116] Table 4 Results of Hair Sensory Test A

[0117]

[0118] Figure 2 Hair strands treated with different compositions are shown, with the one on the left representing Example 1, the one in the middle representing Comparative Example 2, and the one on the right representing Comparative Example 4.

[0119] Compared to the compositions of Comparative Examples 2 and 4, the compositions of Examples 1 and 5 exhibited improved smoothness, wettability, and manageability. Their softness was slightly less than the comparative examples, but still sufficient for practical use.

[0120] Hair sensory test B

[0121] 1.5 g of the compositions of Example 1 and Comparative Example 5 were uniformly applied to moderately damaged hair strands of Asians and then dried at 23°C and 41% humidity for 5 hours. After drying, two members of a specialized panel rated the sensory properties of hair smoothness, softness, moisturizing properties, manageability, non-greasy feel, and non-stickiness on a scale of 1 to 5.

[0122] The average scores of the two compositions are displayed as a sensory graph. Figure 3 In. Figure 3 In this text, "IDD" represents Example 1 and "10 cs" represents Comparative Example 5. Figure 4 The hair strands treated with these two compositions are described, with the one on the left representing Example 1 and the one on the right representing Comparative Example 5.

[0123] The results showed that amino-functionalized silicones formulated with IDD provided excellent conditioning benefits without any negative sensory effects. In contrast, using PDMS oil as a solvent provided an unacceptably greasy and sticky feel, although hair manageability was slightly better.

[0124] In hair sensory tests A and B, higher scores indicate better sensory properties, i.e.:

[0125] "Excellent": 5 points

[0126] "Good": 4 points

[0127] "Normal": 3 points

[0128] "Minor defects": 2 points

[0129] "Poor": 1 point

[0130] Example 6: M R D 650 D N 8.5 M R Preparation of concentrated solutions in isododecane

[0131] Under a nitrogen atmosphere, 200 g of Synthesis Example 2 and 800 g of isododecane were added to a 2000 mL four-necked round-bottom flask. The flask was equipped with a top stirrer, a Dimroth condenser, and a thermometer for temperature monitoring. The mixture was heated to 40-50°C and then stirred for 2 hours to obtain an organosilicon polymer completely dissolved in isododecane. After cooling the product to ambient temperature, it was filtered through diatomaceous earth to obtain 876 g of a clear liquid with 0.097 wt% nitrogen and a viscosity of 19.8 mPa·s at 25°C. After filtration, 2 g of the obtained liquid was weighed in an aluminum pan and placed in an oven at 150°C for 1 hour to measure the solids content. The result was a solids content of 19.8%.

[0132] Example 7: M R D 650 D N 8.5 M R Preparation of concentrated solutions in C9-12 alkanes

[0133] The procedure was similar to that in Example 6, except that 800 g of C9-12 alkanes were used instead of isododecane. 883 g of a clear liquid was obtained, having a nitrogen content of 0.095 wt% and a viscosity of 17.0 mPa·s at 25°C. After filtration, 2 g of the resulting liquid was weighed in an aluminum pan and placed in an oven at 150°C for 1 hour to measure the solids content. The result showed a solids content of 19.7%.

[0134] Example 8: Hair oil conditioner formulation and hair sensory testing

[0135] Three hair oil formulations were prepared using the ingredients listed in Table 5. Six (6) specialists tested each formulation on their hair and rated each sensory attribute on a scale of 1 to 10. The average scores of the six (6) specialists are shown in Table 5.

[0136] Table 5. Hair oil formulations and their sensory results on hair.

[0137]

[0138] Example 9: Wash-out conditioner formulation and hair sensory testing

[0139] Three wash-out conditioner formulations were prepared using the ingredients listed in Table 6. Six (6) specialists tested each formulation on their hair and rated each sensory attribute on a scale of 1 to 10. The average scores of the six (6) specialists are shown in Table 6 and Figure 5 middle.

[0140] Table 6. Wash-out conditioner formulations and their sensory results on hair.

[0141]

[0142] process

[0143] 1. Mix all components in part A and part B separately at 80°C until homogeneous.

[0144] 2. While mixing, add part B to part A.

[0145] 3. Mix for 20 minutes, then cool to 40°C.

[0146] 4. Add portions of C one at a time and mix until homogeneous.

[0147] The resulting formulation remained stable for at least 3 months at 5°C, room temperature, 40°C, and 50°C.

[0148] Example 9 exhibits superior performance in all properties, especially improved softness in application, washing, wet and dry states.

[0149] Example 10: Shampoo Formulation and Hair Sensory Testing

[0150] Three shampoo formulations were prepared using the ingredients listed in Table 7. Six (6) members of a specialist panel tested each formulation on their hair and rated each sensory attribute on a scale of 1 to 10. The average scores of the six (6) specialist panel members are shown in Table 8 and Figure 6 middle.

[0151] Table 7. Shampoo formulations and their sensory results on hair.

[0152]

[0153] process

[0154] 1. Mix all components in phase A until homogeneous. 75 rpm.

[0155] 2. Heat phase B and mix until homogeneous, then add it to phase A and mix thoroughly.

[0156] 3. Add the ingredients from phase C and mix well. (5 minutes, 250 rpm).

[0157] 4. Add phase D to phase ABC, and then heat to 70°C.

[0158] 5. Heat phase E to 70°C until dissolved, then add it to phases A / B / C / D and mix thoroughly.

[0159] 6. Cool to 40°C.

[0160] 7. Add phase F one at a time and mix until homogeneous.

[0161] 8. Adjust the viscosity with phase G and mix thoroughly.

[0162] The resulting formulation remained stable for at least 3 months at 5°C, room temperature, 40°C, and 50°C.

[0163] Table 8. Sensory results of shampoo formulations on hair.

[0164]

[0165] In Examples 8 to 10, regarding the hair sensory test, a higher score indicates better sensory properties, i.e.:

[0166] "Excellent": 10 points

[0167] "Good": 8 points

[0168] "Normal": 5 points

[0169] "Minor defects": 3 points

[0170] "Poor": 1 point

[0171] While this disclosure has been described with reference to preferred embodiments, those skilled in the art will understand that various changes may be made without departing from the scope of this disclosure, and equivalents may be substituted for its elements. Furthermore, many modifications may be made to adapt particular situations or materials to the teachings of this disclosure without departing from the essential scope of this disclosure. Therefore, it is intended that this disclosure be limited to the specific embodiments disclosed as the best mode for carrying out this disclosure, but rather that this disclosure will include all embodiments falling within the scope of the appended claims.

Claims

1. An oil-based composition comprising: (a) an oil-based solvent selected from a hydrocarbon oil; and (b) an organosilicon dissolved or dispersed in the oil-based solvent and having the general formula (I): 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 wherein R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , and R 9 are each independently selected from the group consisting of monovalent hydrocarbon radicals having from about 1 to about 6 carbon atoms; R 3 and R 6 each independently is selected from an alkyl group having from about 20 to about 60 carbon atoms; Each R 10 Independently selected from 3-aminopropyl and N-(2-aminoethyl)-3-aminopropyl; the subscript x has a value of from about 1 to about 2,000, and the subscript y has a value of from about 1 to about 50.

2. The oil-based composition according to claim 1, wherein the composition is non- emulsified.

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

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

5. The oil-based composition of any one of claims 1 to 4, wherein R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , and R 9 are each independently selected from an alkyl group having from about 1 to about 6 carbon atoms, preferably an alkyl group having from about 1 to about 4 carbon atoms, and more preferably methyl.

6. The oil-based composition of any one of claims 1 to 5, wherein R 3 and R 6 are each independently selected from an alkyl group having from about 24 to about 54 carbon atoms, preferably from about 30 to about 50 carbon atoms, and more preferably from about 35 to about 45 carbon atoms.

7. The oil-based composition according to any one of claims 1 to 6, wherein R 10 is N-(2-aminoethyl)-3-aminopropyl.

8. The oil-based composition according to any one of claims 1 to 7, wherein the subscript x has a value of from about 100 to about 1,500, preferably from about 200 to about 1,000, and more preferably from about 300 to about 1,000; and the subscript y has a value of from about 1.5 to about 40, preferably from about 2 to about 30, and more preferably from about 3 to about 20.

9. The oil-based composition according to any one of claims 1 to 8, wherein the organosilicon has a nitrogen content of from about 0.05 wt% to about 2 wt%, preferably from about 0.1 wt% to about 1.5 wt%, and more preferably from about 0.2 wt% to about 1 wt%.

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

30.

11. The oil-based composition according to any one of claims 1 to 10, wherein the composition consists essentially of or consists of component (a) and component (b).

12. A method of making the oil-based composition according to any one of claims 1 to 11, comprising dispersing or dissolving component (b) in component (a), optionally at an elevated temperature.

13. A formulation for conditioning hair comprising the oil-based composition according to any one of claims 1 to 11 or made by the method according to claim 12.

14. The formulation according to claim 13, which is selected from a leave-in and rinse-off hair product; preferably a hair oil, hair serum, hair serum, hair emulsion, shampoo, hair conditioner, hair repair agent, hair care agent, hair treatment agent, or hair mask; especially an end tip oil.

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

16. An oil-based composition comprising, consisting essentially of, or consisting of: (a) an oil-based solvent selected from polydimethylsiloxanes having a viscosity of 9 cps or less at 25 °C and cyclic siloxanes having 10 or fewer silicon atoms, particularly selected from polydimethylsiloxanes having a viscosity of 8 cps or less at 25 °C and cyclic siloxanes having 6 or fewer silicon atoms, and more particularly selected from polydimethylsiloxanes having a viscosity of 5 cps or less at 25 °C and cyclotetrasiloxane, cyclopentasiloxane, and cyclohexasiloxane; and (b) a silicone dissolved or dispersed in the oil-based solvent and having the general formula (I): 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 wherein R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , and R 9 are each independently selected from the group consisting of monovalent hydrocarbon radicals having from about 1 to about 6 carbon atoms; R 3 and R 6 each independently is selected from an alkyl group having from about 20 to about 60 carbon atoms; Each R 10 Independently selected from 3-aminopropyl and N-(2-aminoethyl)-3-aminopropyl; the subscript x has a value of about 1 to about 2,000, and the subscript y has a value of about 1 to about 50.

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