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WO2009021357A1 - Composition d'agent de refroidissement et procede de preparation - Google Patents

Composition d'agent de refroidissement et procede de preparation Download PDF

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Publication number
WO2009021357A1
WO2009021357A1 PCT/CN2007/002427 CN2007002427W WO2009021357A1 WO 2009021357 A1 WO2009021357 A1 WO 2009021357A1 CN 2007002427 W CN2007002427 W CN 2007002427W WO 2009021357 A1 WO2009021357 A1 WO 2009021357A1
Authority
WO
WIPO (PCT)
Prior art keywords
menthol
composition
ethyl
cooling agent
menthylformamide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CN2007/002427
Other languages
English (en)
Chinese (zh)
Inventor
Huashan Li
Luqiu Shi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nanjing Zhongshi Chemical Co Ltd
Original Assignee
Nanjing Zhongshi Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nanjing Zhongshi Chemical Co Ltd filed Critical Nanjing Zhongshi Chemical Co Ltd
Priority to CN2007800436131A priority Critical patent/CN101573099B/zh
Priority to PCT/CN2007/002427 priority patent/WO2009021357A1/fr
Publication of WO2009021357A1 publication Critical patent/WO2009021357A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation

Definitions

  • the present invention relates to a cooling agent composition and a process for the preparation thereof, and more particularly to a amide-containing cooling agent composition and a process for the preparation thereof.
  • Menthol menthol, also known as Menthol, is a colorless crystalline, granulated, minty solid that is readily soluble in ethanol, slightly soluble in water, melting point 40-42 ° C, boiling point 212 ° (: Menthol is a traditional cooling agent. Because it can give the product a cool, fresh feeling, menthol has been widely used in food, medicine, daily chemical, tobacco and other industries, but its shortcomings are also very obvious -
  • Menthramide is a one that has strong impact and durability, no breath, and can improve the cooling taste of L-menthol.
  • a cooling agent that works well with any cooling agent.
  • the mouth-feel threshold is 200 ppb (measured by impregnating the paper strip into the inlet); when tasted at a concentration of 10-100 ppb, "there is a strong and long-term stimulation of the trigeminal nerve, and the cooling taste is slowly stabilized. Enhance, and finally until the mouth is full of cool feeling, accompanied by a slight camphor and mint taste. "Compared with menthol, menthol has the following characteristics:
  • the cooling intensity is 5 times that of menthol, and it has a flavoring effect.
  • Menthramide is mainly used in daily products such as toothpaste, air freshener, skin cream, shaving cream, shampoo, sunscreen, bath, etc.; it can be used in edible products such as chocolate, dairy products, beer, liquor, beverages, etc. In chewing gum and other products, it can also be used in tablets, throat tablets, anti-inflammatory ointments, anti-gastric acid and indigestion drugs, antipruritic agents, oils, oral painkillers, anti-heatstroke drugs, etc.; in addition, menthamide can also be used In tobacco products such as cigarettes and filters, its products are used in a wide range of applications.
  • Menthasamide is usually used in combination with other cooling agents.
  • USP 5,009,893 (Cherukuri et al.) describes a confectionery containing a plurality of cooling agents, wherein the cooling agent comprises menthol and menthamide, and the content of menthamide in the cooling agent is greater than 30% due to the low content of menthamide which results in bitterness.
  • WO 93/23005 discloses a cooling composition comprising a first cooling component ketal 00 2 and a second cooling component menthol amide.
  • WO 93/25177 discloses a cooling composition comprising a first cooling component acyclic formamide and a second cooling component menthamide.
  • Mentha amide is a nearly colorless/white crystal, easily soluble in ethanol, slightly soluble in water, melting point
  • the invention overcomes the disadvantages of the heat of melting or adding solvent or solubilizing component when the menthamide is used as a cooling agent formulation, has poor dispersion uniformity and low concentration, and provides a desiccant composition containing menthamide, which has strong impact, freshness and durability.
  • the aroma and cooling sensation, the composition is liquid at normal temperature and can be used directly; and the composition can achieve a higher concentration of menthamide than other possible ways.
  • Another object of the present invention is to provide a process for preparing the menthamide-containing cooling agent composition.
  • the technical scheme adopted by the present invention is as follows - a menthamide-containing cooling agent composition consisting of menthol and N-ethyl menthylformamide, containing 30% to 80% by weight of menthol and 20% to 70% by weight N-ethylmenthylformamide having a freezing point below 25 °C.
  • Menthol can form a co-melt with other compounds, forming a co-melt having a lower melting point than a single component.
  • the formation of a eutectic mixture of menthol with N-ethyl menthylformamide has not been reported.
  • the present invention combines menthol with N-ethyl menthylformamide and studies the relationship between the freezing point of the eutectic and its composition, as shown in Table 1 and Figure 1.
  • composition melting point and composition
  • the content of menthol is 30% to 80% by weight, N-ethyl menthylcarboxamide.
  • the content is from 20% to 70% by weight, and the resulting composition has a freezing point of less than 25 °C.
  • N-ethyl menthylformamide is a menthol derivative which can be obtained by chemical synthesis, has a melting point of 82-83 ° C, and has the same chirality as menthol, so that it has a good cold feeling.
  • a combination of menthol and menthamide that has a strong, fresh, long-lasting aroma and a refreshing sensation.
  • the menthol component comprises all optical isomers of menthol molecules; the menthamide component is a left-handed or mixed-rotation structure.
  • the menthol content is preferably 40% to 70% by weight, and the content of N-ethyl menthylcarboxamide is From 30% to 60% by weight, the resulting composition has a freezing point of less than 15 °C. More preferably, the content of menthol and N-ethyl menthylformamide is 50% by weight each, and the freezing point of the composition is lower than 9 ° C.
  • the menthol and menthamide compositions provided by the present invention can be used directly as a cooling agent, odor conditioner or perfume, or can be used in the formulation from the composition and other adjuvants.
  • the auxiliary agent may be a liquid substance such as an aqueous dispersant, an alcohol system, a grease, a silicone oil, an ester or an essential oil of the composition; although the solubility of the liquid substance to menthol and menthamide is insufficient to satisfy the requirement of the active substance concentration of the product, It can be used as a liquid dispersion carrier for the composition.
  • the composition of the composition is obtained by adding a composition of menthol and menthamide to a suitable surfactant and mixing with water, oil, fat or the like to carry out a homogenization operation.
  • compositions provided by the present invention can be used as a cooling agent, an odor modifier, and a fragrance in a formulation. Due to the presence of a co-melt of menthol and menthamide, the formulation can be provided with a higher yield of menthamide than other methods. concentration.
  • compositions and dispersions thereof provided by the present invention can be used in various products affecting mucous membranes and skin, such as toothpastes, mouthwashes, perfumes, lotions, shaving creams, post-shave preparations, shampoos, antiperspirants , deodorants, beverages, chewing gum, tobacco products, and pharmaceutical products.
  • composition provided by the present invention is useful as a cooling agent, and has the advantage of producing explosive, instant cooling and durability.
  • the present invention also provides a process for preparing the menthamide-containing cooling agent composition.
  • a method for preparing a mentholamide-containing cooling agent composition comprising the steps of:
  • the mentholamide-containing refresher composition provided by the present invention is liquid at normal temperature, and is not required It is heated and melted, and can be used directly or in combination with an adjuvant, and is convenient to use as a cooling agent; and the composition can achieve a higher concentration of menthamide than other methods.
  • a cooling agent the application of the composition saves energy, saves costs, and simplifies the process.
  • the preparation method of the composition is simple.
  • Figure 1 is a graph showing the relationship between the freezing point and the menthol content of the composition of the present invention.
  • Example 4 60 g of solid menthol and 40 g of N-ethyl-L-menthylformamide were placed in a beaker at room temperature, stirred at low speed for 30 min, and the composition slowly turned from solid to viscous and gradually clarified to obtain the desired oil. Things. The composition was subjected to a freezing point test with a freezing point of 12 °C.
  • Example 5 60 g of solid menthol and 40 g of N-ethyl-L-menthylformamide were placed in a beaker at room temperature, stirred at low speed for 30 min, and the composition slowly turned from solid to viscous and gradually clarified to obtain the desired oil. Things. The composition was subjected to a freezing point test with a freezing point of 12 °C.
  • Example 5 60 g of solid menthol and 40 g of N-ethyl-L-menthylformamide were placed in a beaker at room temperature, stirred at low speed for 30 min, and the composition slowly turned
  • Example ⁇ 20 g of the composition of Example 3, 6 g of Tween 120 and 174 g of water were added, homogenized at room temperature, and the homogenizer speed was 5000 rpm to prepare a milky white stable 10% menthol and N-ethyl menthyl formamide. Water dispersant.
  • Example ⁇ 20 g of the composition of Example 3, 6 g of Tween 120 and 174 g of water were added, homogenized at room temperature, and the homogenizer speed was 5000 rpm to prepare a milky white stable 10% menthol and N-ethyl menthyl formamide. Water dispersant.
  • Example ⁇ 20 g of the composition of Example 3, 6 g of Tween 120 and 174 g of water were added, homogenized at room temperature, and the homogenizer speed was 5000 rpm to prepare a milky white stable 10% menthol and N-ethyl menthyl formamide. Water dispersant.
  • Example 8 20 g of the composition of Example 3, adding 7.2 g of Phospholipid sv (stearamidopropyl propylene glycol monophospholipid dimethyl ammonium chloride), 7.2 g of Brij72 (polyoxyethylene-2-monostearate) and Add water to a total amount of 200g, homogenize at room temperature with a homogenizer, and homogenize in a high-pressure high-shear emulsifier to form a milky white stable 10% nanomenthol and N-ethyl-L-menthol Amide water dispersant.
  • Phospholipid sv stearamidopropyl propylene glycol monophospholipid dimethyl ammonium chloride
  • Brij72 polyoxyethylene-2-monostearate
  • Example 3 40 g of the composition of Example 3 was added to 10 g of Siban 160 and 150 g of dimethicone, homogenized at room temperature, and the homogenizer was rotated at 5000 rpm to prepare a milky white stable 20% menthol and N-ethyl- An oil dispersant for L-menthylformamide.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Nutrition Science (AREA)
  • Inorganic Chemistry (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne une composition d'agent de refroidissement contenant un N-éthyle-menthane-carboxamide et un procédé pour sa préparation. Ladite composition se compose de 30 à 80 % en poids de menthol et de 20 à 70 % en poids de N-éthyle-menthane-carboxamide, et son point de congélation est inférieur à 25°C. Le procédé de préparation de ladite composition comprend les étapes suivantes : 1) ajout du menthol et du N-éthyle-menthane-carboxamide dans le récipient selon les proportions ; 2) agitation du mélange dans le récipient jusqu'à obtention d'une clarification et d'un mélange de clarification. La composition d'agent de refroidissement de l'invention est liquide à température ambiante, et peut être utilisée avec d'autres adjuvants sans chauffage pour atteindre le point de fusion.
PCT/CN2007/002427 2007-08-13 2007-08-13 Composition d'agent de refroidissement et procede de preparation Ceased WO2009021357A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN2007800436131A CN101573099B (zh) 2007-08-13 2007-08-13 一种清凉剂组合物及其制备方法
PCT/CN2007/002427 WO2009021357A1 (fr) 2007-08-13 2007-08-13 Composition d'agent de refroidissement et procede de preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2007/002427 WO2009021357A1 (fr) 2007-08-13 2007-08-13 Composition d'agent de refroidissement et procede de preparation

Publications (1)

Publication Number Publication Date
WO2009021357A1 true WO2009021357A1 (fr) 2009-02-19

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PCT/CN2007/002427 Ceased WO2009021357A1 (fr) 2007-08-13 2007-08-13 Composition d'agent de refroidissement et procede de preparation

Country Status (2)

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CN (1) CN101573099B (fr)
WO (1) WO2009021357A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109171014A (zh) * 2018-10-11 2019-01-11 湖北中烟工业有限责任公司 一种薄荷醇低共熔溶剂及烟用胶囊
WO2021017137A1 (fr) * 2019-07-26 2021-02-04 深圳雾芯科技有限公司 Chewing-gum, e-liquide et leur utilisation
CN112807278A (zh) * 2019-11-15 2021-05-18 湖北远大天天明制药有限公司 一种鼻用组合物及其制备方法与应用
CN114831142A (zh) * 2022-01-21 2022-08-02 珠海市合顺兴日化股份有限公司 一种清凉防虫喷雾及其制备方法
CN114983674A (zh) * 2022-06-15 2022-09-02 郑州市新视明科技工程有限公司 一种用于热敷眼罩的清凉剂的制备方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102872476B (zh) * 2012-08-10 2016-08-03 泉州市晋江恒安卫生科技有限公司 复合清凉剂、复合清凉剂制备方法及一次性卫生用品
CN105687020A (zh) * 2016-01-20 2016-06-22 广州丹奇日用化工厂有限公司 防治足部皲裂的爽足粉
GB201620352D0 (en) 2016-11-30 2017-01-11 British American Tobacco Investments Ltd Smoking article
CN107950983A (zh) * 2017-11-27 2018-04-24 昆山亚香香料股份有限公司 一种以薄荷醇为基础的复配凉味剂组合物及其制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1275887A (zh) * 1997-09-18 2000-12-06 Wm.雷格利Jr.公司 含生理清凉剂的口香糖
WO2006071749A1 (fr) * 2004-12-29 2006-07-06 Wm. Wrigley Jr. Company Combinaisons d'agents de refroidissement a utiliser dans des friandises

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1275887A (zh) * 1997-09-18 2000-12-06 Wm.雷格利Jr.公司 含生理清凉剂的口香糖
WO2006071749A1 (fr) * 2004-12-29 2006-07-06 Wm. Wrigley Jr. Company Combinaisons d'agents de refroidissement a utiliser dans des friandises

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109171014A (zh) * 2018-10-11 2019-01-11 湖北中烟工业有限责任公司 一种薄荷醇低共熔溶剂及烟用胶囊
WO2021017137A1 (fr) * 2019-07-26 2021-02-04 深圳雾芯科技有限公司 Chewing-gum, e-liquide et leur utilisation
CN112807278A (zh) * 2019-11-15 2021-05-18 湖北远大天天明制药有限公司 一种鼻用组合物及其制备方法与应用
CN114831142A (zh) * 2022-01-21 2022-08-02 珠海市合顺兴日化股份有限公司 一种清凉防虫喷雾及其制备方法
CN114983674A (zh) * 2022-06-15 2022-09-02 郑州市新视明科技工程有限公司 一种用于热敷眼罩的清凉剂的制备方法

Also Published As

Publication number Publication date
CN101573099B (zh) 2011-08-03
CN101573099A (zh) 2009-11-04

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