Fragrance durability improving agent, preparation method thereof, essence and hair washing product

Abstract

The invention relates to an aroma durability improving agent and a preparation method thereof, an essence and a shampoo product, and the aroma durability improving agent comprises the following components in percentage by weight: 40%-60% of a component A, 1%-0.5% of a component B, 10%-20% of a component C, 10%-20% of a component D, 5%-10% of isooctyl salicylate, 10%-20% of a perfume component and the balance of a solvent, wherein the component A is prepared from 2-[[3-[2-methyl-4-(2-methylpropyl) phenyl] propylidene] amino] methyl benzoate; the long-lasting fragrance can be effectively improved, the preparation process is simple, the production cost is low, the compatibility is good, and the long-lasting fragrance is suitable for various essences or hair washing products.

Description

Technical Field

[0001] The present invention relates to the technical field of hair care products, and particularly relates to an aroma persistence enhancer, a preparation method thereof, a fragrance, and a hair care product. Background Art

[0002] As a daily necessity in the field of personal care, consumers' expectations for the functions of hair care products have evolved from simple cleansing to include multiple effects such as nourishing, repairing, styling, and fragrance retention. As a result, products such as hair conditioners, hair essential oils, and hair masks have emerged. In terms of fragrance retention, with the improvement of consumers' requirements for the quality of life, whether a product can provide emotional value has become an important consideration factor for consumers when making consumption decisions. The market demand for hair care products with a long-lasting fragrance retention effect and a pleasant remaining fragrance is increasing day by day.

[0003] The commonly used techniques in the industry to enhance the fragrance retention effect of fragrances mainly include: (1) Adding fixatives: such as benzyl benzoate and benzyl salicylate. This method can make fragrance molecules stay more persistently on hair or clothing fibers by reducing the vapor pressure of fragrance molecules. (2) Microcapsule technology: Encapsulating fragrance components in microcapsules and controlling the rate of fragrance release to extend the fragrance emission time. This method can significantly improve the stability of fragrances and reduce the volatilization and degradation of fragrances caused by factors such as light, temperature changes, and oxidation. (3) Application of nanomaterials: Using nanoparticles as carriers to immobilize fragrance molecules on the nanocarriers to improve their tolerance and persistence.

[0004] However, the above technologies still have problems in practical applications, which are specifically manifested in the following aspects: (1) The fragrance fixative itself has a very light aroma. When a small amount is added, it is difficult to be perceived and basically has no effect. When a large amount of fragrance fixative is added, the overall aroma becomes dull and not volatilized, and the remaining aroma is often not pleasant enough. (2) The microcapsule encapsulation technology has achieved remarkable results in laundry detergents and fragrance retention products, but the effect is very poor in hair care products because there are great differences in the surface characteristics and cleaning methods of clothes and hair. Clothing fibers are usually relatively rough, with large gaps between fibers, which can better adsorb microcapsules; while the adsorption of microcapsules on hair is affected by the surface charge and smooth characteristics of hair, and the adsorption force is weak. Hair has a shorter contact time with the detergent during the washing process compared to clothes, and is usually rinsed in high-speed flowing water, making it easier for microcapsules to desorb and crack prematurely. In addition, a large amount of suspending agent needs to be added additionally when microcapsule fragrances are applied in hair care products, which will not only reduce the conditioning effect of the shampoo, but also the dispersion state of the microcapsule fragrances themselves is easily affected by environmental factors such as temperature and light, resulting in sedimentation or floating, leading to the deterioration of the shampoo. The microcapsule technology is relatively mature abroad, but the cost is high and the technology is complex; the domestic microcapsule technology still faces problems such as too large particle size, too low encapsulation amount, and environmental pollution during production and use, resulting in a very limited penetration rate of microcapsule fragrances in the hair care product market. (3) The nano-material carrier technology is still in its infancy, and the potential biological toxicity of nano-particles is highly controversial. Secondly, nano-particles are prone to agglomeration, and the dispersion and stability of nano-materials, as the key technical problems in the application of this technology, have not been solved. Coupled with the huge production input cost, this technology cannot be actually applied to commercial products at present.

[0005] Therefore, in terms of improving the fragrance persistence of hair care products, there is an urgent need for a technical means that is both practical and effective, and at the same time, this technical method should also have the characteristics of relatively low production input cost, so as to increase the market penetration rate and enable a wider range of consumers to enjoy the lasting fragrant hair care experience. Summary of the Invention

[0006] The purpose of the present invention is to provide an agent for improving fragrance persistence, its preparation method, fragrance and hair care product, which can effectively improve the fragrance persistence, has a simple preparation process, low production cost, good compatibility, and is applicable to various fragrances or hair care products.

[0007] To achieve this purpose, the present invention adopts the following technical solutions: Provide an agent for improving fragrance persistence, which contains the following components by weight percentage: Component A 40%-60%, Component B 01%-0.5%, Component C 10%-20%, Component D: 10% - 20%, isooctyl salicylate: 5% - 10%, spice component: 10% - 20%, and the balance of solvent; Among them, the said Component A includes: methyl 2-[[3-[2-methyl-4-(2-methylpropyl)phenyl]propylidene]amino]benzoate; it is synthesized by the applicant and has no registered CAS number. Component A is a compound synthesized in the present invention with a large relative molecular mass, high consistency, and strong fragrance. The aroma intensity is more than 20 times that of ordinary fixatives. It is found through testing that the compound of this component can be well deposited on the hair and can retain a sweet fragrance on the hair.

[0008] The said Component B includes: at least one compound among 2-isopropyl-4-methylthiazole, cis-6-nonen-1-ol, trans-2-cis-6-nonadienal, 2-methyl-4-propyl-1,3-oxathiane (passion fruit thioether), 2-ethyl-3-hydroxy-4-pyrone (ethyl maltol), 7-methyl-1,5-benzodioxepan-3-one (watermelon ketone), 4,8-dimethyl-4,9-decadienal, 1-p-menthene-8-thiol, and 8-mercaptomaleimide; Component B is a spice with a low olfactory threshold, relatively pleasant aroma, and the odor is suitable for use in hair washing products. Such spices can be perceived at a lower concentration, thereby enhancing the perception and persistence of the aroma.

[0009] The said Component C includes: at least one compound among 2,2,6-trimethyl-α-propylcyclohexylpropanol (saimu xiangchun), 2-ethyl-4-(2,2,3-trimethylcyclopent-3-enyl)but-2-enol (santalol 208), 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopentyl)-4-penten-2-ol (poly santalol), crystallized rose, nerolidol, geraniol, and 2-ethyl-N-methyl-N-(3-methylphenyl)butanamide (fruit amide); Component C is a compound with a specific structure or functional group, which can be better adsorbed on the hair through intermolecular interactions. For example, the alcohol hydroxyl group forms a hydrogen bond with the amino acid in the hair, and the presence of a hydrophobic group makes the compound less likely to be carried away by the water flow during the hair rinsing process.

[0010] The component D includes: 3,7-dimethyloctane-1,6-diene-3-ol (linalool), cis-3-hexene-1-ol (leaf alcohol), 2,2,6-trimethylcyclohexanecarboxylic acid methyl ester, 2,2,6-trimethyl-α-propylcyclohexyl propanol (saikenol), 2-butyl-4,4,6-trimethyl-1,3-dioxocyclohexane (lavenderoxane), cis-4-(1-methylethyl)cyclohexanol (may lily alcohol), 2-(1,1-dimethylpropyl)cyclohexanol acetate (kanglifa ester), 1-(2-tert-butylcyclohexyloxy)-2-butanol, 2-ethyl-4-(2,2,3-trimethylcyclopenta-3- At least one of the following compounds: 1,2-dimethyl-2-heptyl-1-ol (sandalwood 208), 2,6-dimethyl-5-heptenal (melon aldehyde), 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde (privet aldehyde), 2,4-dihydroxy-3,6-dimethylbenzoic acid methyl ester (synthetic oak moss), raspberry ketone, γ-undecalactone, γ-decanoic acid, 2,6-dimethyl-2-heptanol, hexyl acetate, ethyl propionate, 1,8-cineole and patchouli oil; component D is a fragrance that has been tested to effectively mask the odor of scalp oil. The addition of this type of compound can solve the problem of unclear shampoo fragrance caused by masking the odor of scalp oil.

[0011] The isooctyl salicylate is used as an anti-ultraviolet agent in the enhancer. Ultraviolet radiation can cause the hair scales to curl up, exposing the aroma molecules originally adsorbed between the hair scales to the air, accelerating their oxidation and dissipation. Therefore, the addition of an anti-ultraviolet agent can also enhance the durability of the hair fragrance. The adsorption amount of isooctyl salicylate on the hair and the effect of resisting light damage are better than other commonly used anti-ultraviolet agents, such as butyl methoxydibenzoylmethane (avobenzone), octyl p-methoxycinnamate, and 2-hydroxy-4-methoxybenzophenone.

[0012] The fragrance component plays a role in blending the aroma and balancing the aromas at different volatilization stages in the enhancer.

[0013] As a preferred embodiment of the fragrance persistence enhancer, the preparation of methyl 2-[[3-[2-methyl-4-(2-methylpropyl)phenyl]propylidene]amino]benzoate comprises the following steps: 3-(4-isobutyl-2-methylphenyl)propanal and methyl anthranilate were added to a reaction kettle at a molar ratio of 1:1 and stirred for 24 hours, during which the water generated during the reaction was separated by a water separator; The mixture was allowed to stand for 48 h until it became clear and viscous, to obtain methyl 2-[[3-[2-methyl-4-(2-methylpropyl)phenyl]propylidene]amino]benzoate.

[0014] As a preferred embodiment of the aroma persistence enhancer, the component A further includes at least one compound selected from methyl 2-[[2-methyl-3-[4-(1-methylethyl)phenyl]propylidene]amino]benzoate (CAS No.: 91-50-9), methyl 2-[[3-(1,3-benzodioxol-5-yl)-2-methylmethylene]amino]benzoate (CAS No.: 111753-60-7), methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate (CAS No.: 89-43-0), methyl 2-[[(2,4-dimethyl-3-cyclohexen-1-yl)methylene]amino]benzoate (CAS No.: 68845-02-3), methyl 2-[[[4-(4-methyl-3-pentenyl)-3-cyclohexen-1-yl]methylene]amino]benzoate (CAS No.: 93894-30-5), and methyl 2-[[3-(4-methoxyphenyl)-2-methylpropylidene]amino]benzoate (CAS No.: 111753-62-9). Adding other compounds to component A and cooperating with methyl 2-[[3-[2-methyl-4-(2-methylpropyl)phenyl]propylidene]amino]benzoate, due to the different boiling points of each compound, the compounds with different boiling points exhibit different rates during the volatilization process, enabling the aroma to be better distributed in time and space, thereby improving the aroma retention effect.

[0015] As a preferred embodiment of the aroma persistence enhancer, the solvent is at least one compound selected from benzyl salicylate, benzyl benzoate, and isopropyl myristate.

[0016] As a preferred embodiment of the aroma persistence enhancer, the fragrance component is at least one compound selected from natural extracts and synthetic molecules, wherein the natural extracts include: essential oils, absolutes, tinctures, resins, and concretes; the synthetic components include: terpenes and their derivatives, alcohols, ethers, aldehydes, ketones, esters, and lactones.

[0017] As a preferred embodiment of the aroma persistence enhancer, the terpenes and their derivatives include: pinene, myrcene, caryophyllene; alcohols such as phenethyl alcohol, geraniol, citronellol, and terpineol; the ethers include: p-cresyl methyl ether and rose ether; the aldehydes include: decanal, octanal, α-hexylcinnamaldehyde, and vanillin; the ketones include: ionone, damascenone, and ambrein; the esters include: benzyl acetate, linalyl acetate, and methyl dihydrojasmonate; the lactones include coumarin.

[0018] The present invention also provides a preparation method of the aroma persistence enhancer according to any one of the above, comprising the following steps: Adding component A, component B, component C, component D, isooctyl salicylate, and the fragrance component into a solvent respectively and stirring and mixing them.

[0019] The present invention also provides an essence, which comprises the aroma persistence enhancer described in any one of the above, and the weight percentage of the aroma persistence enhancer in the essence is 2%-10%.

[0020] The present invention also provides a hair washing product, which comprises the above essence.

[0021] Advantages of the present invention: The aroma persistence enhancer, its preparation method, the essence and the hair washing product provided by the present invention are designed with methyl 2-[[3-[2-methyl-4-(2-methylpropyl)phenyl]propylidene]amino]benzoate in component A; it is a compound synthesized by the present invention with a large relative molecular mass, high consistency and strong aroma, and the aroma intensity is more than 20 times that of ordinary fixatives. It is found through testing that the compound of this component can be well deposited on the hair and can retain a sweet aroma on the hair; and in combination with other components, the enhancer can effectively improve the aroma persistence, without the need for special encapsulation design, the preparation process is simple, the production cost is low, it has good compatibility, and is applicable to various essences or hair washing products. Specific embodiments

[0022] The following will describe the embodiments of the present disclosure in detail.

[0023] The following specific examples illustrate the embodiments of the present disclosure. Those skilled in the art can easily understand other advantages and effects of the present disclosure from the content disclosed in this specification. Obviously, the described embodiments are only a part of the embodiments of the present disclosure, rather than all the embodiments. The present disclosure can also be implemented or applied through other different specific embodiments, and various details in this specification can also be modified or changed based on different viewpoints and applications without departing from the spirit of the present disclosure. It should be noted that, on the premise of no conflict, the following described embodiments or technical features can be combined with each other to form new embodiments arbitrarily. Those conditions not specified in the examples are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used without indicating the manufacturer are all conventional products that can be obtained through commercial purchase. The reagents used in the examples can be purchased conventionally from the market as long as there is no special description. Based on the embodiments in the present disclosure, all other embodiments obtained by those of ordinary skill in the art without creative efforts belong to the scope protected by the present disclosure.

[0024] The present invention will be further described with reference to the examples. All percentages used in the tables refer to weight percentages.

[0025] The examples include the following components: Component A selects methyl 2-[[3-[2-methyl-4-(2-methylpropyl)phenyl]propylidene]amino]benzoate (hereinafter referred to as A1), methyl 2-[[2-methyl-3-[4-(1-methylethyl)phenyl]propylidene]amino]benzoate (hereinafter referred to as A2), methyl 2-[[3-(1,3-benzodioxol-5-yl)-2-methylmethylene]amino]benzoate (hereinafter referred to as A3); Component B selects 2-isopropyl-4-methylthiazole, passionflower thioether; Component C selects saimangol, sandalwood 208, crystallized rose, geraniol; Component D selects linalool, raspberry ketone, γ-undecalactone; The fragrance component selects methyl dihydrojasmonate, vanillin, galaxolide, β-ionone; isooctyl salicylate; The solvent selects isopropyl myristate.

[0026] The compositions of each example and comparative example are shown in Table 1 below Table 1 The improvement effect of the enhancer on the persistence of hair fragrance and the pleasantness of the remaining fragrance were evaluated by the following evaluation methods.

[0027] Experiment 1: Experiment on fragrance persistence Blank group: Perfume without enhancer Experimental group: Perfumes of Examples 1-5 and Comparative Examples 1-5 were added respectively, and the addition amount was 5% of the weight of the perfume. Take 11 portions of unscented shampoo base materials with the same weight, add the perfumes of the blank group and the experimental group in the same proportion respectively, mix evenly to obtain the shampoos of the blank group and the experimental group, and conduct simulated hair washing experiments respectively.

[0028] Prepare 11 portions of clean and odorless real hair bundles and 11 identical clean containers. The weight of each hair bundle is kept basically the same. Put one hair bundle in each container, then add the shampoos of the blank group and the experimental group respectively, add pure water and rub to form foam, so that the shampoo forms sufficient foam and adheres evenly to the surface of the hair bundle. After rubbing for 30 min, rinse the foam with pure water and dry it in a natural ventilation environment. After drying, place the hair bundles in a room at room temperature for storage, and conduct fragrance evaluation at 0 h, 4 h, 8 h, and 24 h respectively.

[0029] Fifteen perfume assessors were selected. Taking the hair bundle of the blank group at the 0h as the standard sample with a score set at 8 points, the assessors were asked to score from 0 to 10 points according to the difference in the aroma intensity between the blank group and the experimental group and that of the standard sample. The highest score was 10 points. If the score was greater than 8 points, it indicated that the assessor thought the aroma intensity of the hair bundle was better than that of the hair bundle of the blank group at 0h; otherwise, it was considered that the aroma intensity of the hair bundle was inferior to that of the hair bundle of the blank group at 0h, and the greater the difference from the standard sample, the lower the score. The score could have one decimal place. The scores of the hair bundles in the blank group and the experimental group at each time period were statistically analyzed, and outliers were analyzed and excluded using the Q-test method. Then, the average value of the scores was recorded, and this average value was the fragrance retention value.

[0030] Experiment 2: Aroma pleasantness experiment Fifteen perfume assessors were selected and asked to score the aromas of the above-mentioned hair bundles in the blank group and the experimental group. The highest score was 5 points, and the score could have one decimal place. The scoring criteria are shown in Table 2 below. The scores of the blank group and the experimental group were statistically analyzed, and outliers were analyzed and excluded using the Q-test method. Then, the average value of the scores was recorded, and this average value was the pleasantness.

[0031] Table 2 The results of Experiment 1 and Experiment 2 are shown in Table 3 below. Table 3 From the comparison of the results of the blank group and Example 1 in Table 3, it can be seen that the aroma of the hair bundle in the blank group without the enhancer dissipated rapidly with the extension of the placement time, while the addition of the enhancer described in the present invention can effectively extend the retention time of the hair aroma and maintain the pleasantness of the aroma.

[0032] From the comparison of the results of the blank group and Comparative Example 1 as well as Comparative Examples 2 - 4 in Table 3, it can be seen that adding an enhancer without Component A can still improve the persistence of the aroma compared to the blank group without the enhancer, but the effect is greatly reduced. The reduction in effect is greater than that of Comparative Example 2 without Component B, Comparative Example 3 without Component C, and Comparative Example 4 without Component D, indicating that Component A is the key component for improving the persistence of the hair aroma.

[0033] From the comparison of the results of Example 2 and Example 3 in Table 3, it can be seen that the fragrance retention effect of methyl 2 - [[3 - [2 - methyl - 4 - (2 - methylpropyl)phenyl]propylidene]amino]benzoate synthesized in the present invention in Component A is better than that of other compounds in Component A.

[0034] From the comparison of the results of Example 1 and Example 2 in Table 3, it can be seen that the fragrance retention effect of selecting multiple compounds in Component A is better than that of selecting only one compound.

[0035] From the result comparison between Example 1 and Comparative Examples 1-4 in Table 3, as well as between Example 1 and Comparative Example 5, it can be seen that removing some components (Comparative Examples 1-4) or changing the proportion between each component (Comparative Example 5) results in a significant difference in the fragrance retention effect or the pleasantness of the retained fragrance.

[0036] The above is only to illustrate the implementation mode of the present invention and is not intended to limit the present invention. For those skilled in the art, any modification, equivalent replacement, improvement, etc. made without creative labor within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. A fragrance persistence enhancing agent, characterized in that The following components are included in weight percentage: Component A 40%-60%, Component B 01%-0.5%, Component C 10%-20%, Component D 10%-20%, Isooctyl salicylate 5%-10%, Fragrance components 10%-20%, and the balance solvent; Wherein, the component A comprises: methyl 2-[[3-[2-methyl-4-(2-methylpropyl)phenyl]propylidene]amino]benzoate; The component B comprises at least one compound selected from the group consisting of 2-isopropyl-4-methylthiazole, cis-6-nonene-1-ol, trans-2-cis-6-nonadienal, 2-methyl-4-propyl-1,3-oxathiacyclohexane, 2-ethyl-3-hydroxy-4-pyrone, 7-methyl-1,5-benzodioxepan-3-one, 4,8-dimethyl-4,9-decadienal, 1-p-menene-8-thiol and 8-mercaptomaleic ketone; The component C comprises at least one compound selected from the group consisting of serrata alcohol, sandalwood 208, polysantalol, crystal rose, nerolidol, geraniol and fruit amide; The component D comprises at least one compound selected from linalool, leaf alcohol, 2,2,6-trimethylcyclohexanecarboxylic acid methyl ester, cypermethrin, lavandula angustifolia, lily of the valley alcohol, santalin, 1-(2-tert-butylcyclohexyloxy)-2-butanol, santalum 208, melon aldehyde, privet aldehyde, synthetic oak moss, raspberry ketone, γ-undecalactone, γ-decanoic acid, 2,6-dimethyl-2-heptanol, hexyl acetate, ethyl propionate, 1,8-cineole and patchouli oil.

2. The aroma persistence enhancing agent according to claim 1, characterized in that The preparation of the methyl 2-[[3-[2-methyl-4-(2-methylpropyl)phenyl]propylidene]amino]benzoate comprises the following steps: 3-(4-isobutyl-2-methylphenyl)propanal and methyl anthranilate were added to a reaction kettle at a molar ratio of 1:1 and stirred for 24 hours, during which the water generated during the reaction was separated by a water separator; The mixture was allowed to stand for 48 h until it became clear and viscous, to obtain methyl 2-[[3-[2-methyl-4-(2-methylpropyl)phenyl]propylidene]amino]benzoate.

3. The aroma persistence enhancing agent according to claim 1, characterized in that The component A also includes: methyl 2-[[2-methyl-3-[4-(1-methylethyl)phenyl]propylidene]amino]benzoate, methyl 2-[[3-(1,3-benzodioxolan-5-yl)-2-methylendylidene]amino]benzoate, methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate, methyl 2-[[(2,4-dimethyl-3-cyclohexen-1-yl)methylene]amino]benzoate, methyl 2-[[[4-(4-methyl-3-pentenyl)-3-cyclohexen-1-yl]methylene]amino]benzoate and methyl 2-[[3-(4-methoxyphenyl)-2-methyl-propylidene]amino]benzoate.

4. The aroma persistence enhancing agent according to claim 1, characterized in that The solvent is at least one compound selected from benzyl salicylate, benzyl benzoate and isopropyl myristate.

5. The aroma persistence enhancing agent according to claim 1, characterized in that The fragrance components are at least one compound of natural extracts and synthetic molecules, wherein the natural extracts include essential oils, absolute oils, tinctures, resins and extracts; the synthetic components include terpenes and their derivatives, alcohols, ethers, aldehydes, ketones, esters and lactones.

6. The aroma persistence enhancing agent according to claim 5, characterized in that The terpenes and their derivatives include: pinene, myrcene, caryophyllene; alcohols, such as phenylethyl alcohol, geraniol, citronellol and pinoleyl alcohol; the ethers include: p-cresol methyl ether and rose oxide; the aldehydes include: decanal, octanal, α-hexylcinnamaldehyde and vanillin; the ketones include: ionone, damascena and ambroxan; the esters include: benzyl acetate, linalyl acetate and methyl dihydrojasmonate; the lactones include coumarin.

7. A method for preparing the aroma persistence enhancer according to any one of claims 1 to 6, characterized in that: The following steps are involved: Component A, component B, component C, component D, isooctyl salicylate and fragrance component are respectively added into the solvent and stirred and mixed.

8. A flavor, characterized in that: The flavor comprises the aroma persistence enhancing agent according to any one of claims 1 to 6, and the aroma persistence enhancing agent accounts for 2% to 10% by weight of the flavor.

9. A shampoo product, characterized in that: The shampoo product comprises the essence according to claim 8.

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