CN111349518A - Essence and spice slow-release preparation method - Google Patents
Essence and spice slow-release preparation method Download PDFInfo
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- CN111349518A CN111349518A CN202010189735.9A CN202010189735A CN111349518A CN 111349518 A CN111349518 A CN 111349518A CN 202010189735 A CN202010189735 A CN 202010189735A CN 111349518 A CN111349518 A CN 111349518A
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- Prior art keywords
- polyethylene glycol
- perfume
- acrylate
- steps
- slow release
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0003—Compounds of unspecified constitution defined by the chemical reaction for their preparation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/026—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from the reaction products of polyepoxides and unsaturated monocarboxylic acids, their anhydrides, halogenides or esters with low molecular weight
- C08F299/028—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from the reaction products of polyepoxides and unsaturated monocarboxylic acids, their anhydrides, halogenides or esters with low molecular weight photopolymerisable compositions
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
The invention discloses a method for preparing essence and spice in a sustained-release manner, which specifically comprises the following steps: firstly, preparing a wrapping material monomer, namely performing ester exchange reaction on methyl acrylate or ethyl acrylate and polyethylene glycol monomethyl ether under an alkaline condition to prepare a crude product of polyethylene glycol acrylate; and secondly, fully and uniformly mixing the crude product of the polyethylene glycol acrylate prepared in the last step with the perfume, then carrying out polymerization reaction on an alkenyl unit of the polyethylene glycol acrylate, and simultaneously wrapping perfume molecules in a polymer chain, thereby obtaining the polymer-wrapped perfume. The polymer of the acrylic acid polyethylene glycol ester is used for wrapping the perfume molecules, so that physical limitation is formed on the perfume molecules, the volatilization speed of the perfume molecules is reduced, and the slow release effect is achieved. The volatilization speed of the polymer-coated perfume prepared by the two steps is obviously reduced, and the utilization rate of the perfume is greatly improved.
Description
Technical Field
The invention relates to the technical field of organic synthesis, daily chemicals and cosmetics, in particular to a method for preparing essence and spice in a sustained-release manner.
Background
The essence and the spice are widely applied to the fields of various perfumes, skin care products, cleaning products and the like. The traditional method of using essence is to add a certain amount of essence directly into the relevant product, and then to mix simply. The product obtained by this method has no physical constraints on perfume molecules, and its volatilization speed is mainly determined by ambient temperature and air pressure. Thus, to extend the time that the fragrance remains, the rate of volatilization of the fragrance molecules must be reduced, which traditionally has been achieved only by lowering the temperature or increasing the ambient air pressure. The temperature and the air pressure are often determined by the using scene of the product and are difficult to change, so that the traditional method for using the perfume often has the phenomenon that the fragrance disappears quickly, namely the utilization rate of the perfume is low.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides the preparation method of the essence and flavor slow release, which utilizes the polymer of the acrylic acid polyethylene glycol ester to wrap the flavor molecules and forms a physical limit on the flavor molecules, thereby reducing the volatilization speed of the flavor molecules and achieving the effect of slow release.
The technical scheme for solving the problems comprises the following steps: a method for preparing essence and spice slow release specifically comprises the following steps:
firstly, preparing a wrapping material monomer, namely performing ester exchange reaction on methyl acrylate or ethyl acrylate and polyethylene glycol monomethyl ether under an alkaline condition, mixing the methyl acrylate or the ethyl acrylate and the polyethylene glycol monomethyl ether in a reaction bottle, adding a catalytic amount of alkali, without any solvent, and reacting for 10 hours at 20-40 ℃ to obtain a crude product of the polyethylene glycol acrylate;
and secondly, fully and uniformly mixing the crude product of the polyethylene glycol acrylate prepared in the last step with the perfume, then carrying out polymerization reaction on an alkenyl unit of the polyethylene glycol acrylate, and simultaneously wrapping perfume molecules in a polymer chain, thereby obtaining the polymer-wrapped perfume.
Furthermore, in the first step, the mass ratio of the acrylate to the polyethylene glycol amine monomethyl ether is 1-1.2: 1;
further, in the first step, the polyethylene glycol monomethyl ether is selected from one or more of polyethylene glycol monomethyl ethers with molecular weight of 200-1000;
preferably, the methoxypolyethylene glycol is one or more selected from mPEG200, mPEG300, mPEG400, mPEG500, mPEG600, mPEG800 and mPEG 1000;
further, in the first step, the alkali is selected from one or more of potassium carbonate, sodium carbonate, potassium hydroxide and sodium hydroxide, and the mass ratio of the alkali to the acrylate is 0.1-0.02: 1;
further, in the second step, during the polymerization reaction, mechanical stirring is adopted, and the mixture is vigorously stirred for 1 hour at room temperature;
further, in the second step, during the polymerization reaction, the ultraviolet light is adopted for irradiation at the high temperature of 100-120 ℃;
further, in the second step, during the polymerization reaction, the mass ratio of the polyethylene glycol acrylate to the perfume is 1: 2-10, preferably 1: 5.
the invention has the following beneficial effects:
the invention provides a method for preparing essence and spice in a sustained-release manner, which utilizes a polymer of polyethylene glycol acrylate to wrap spice molecules and forms a physical limit on the spice molecules, thereby reducing the volatilization speed of the spice molecules and achieving the effect of sustained release. The volatilization speed of the polymer-coated perfume prepared by the two steps is obviously reduced, and the utilization rate of the perfume is greatly improved.
Detailed Description
The present invention is described in detail with reference to the following embodiments, which are only preferred embodiments of the present invention, and not intended to limit the present invention in other forms, and any person skilled in the art may apply the above-described modifications or changes to the equivalent embodiments with equivalent changes without departing from the technical spirit of the present invention, and any simple modification, equivalent change and change made to the above embodiments according to the technical spirit of the present invention still belong to the protection scope of the technical spirit of the present invention.
The first embodiment is as follows:
1 kg (1mol) of polyethylene glycol monomethyl ether (mPEG1000) with the molecular weight of 1000, 86 g (1mol) of methyl acrylate and 6.9 g (0.05mol) of potassium carbonate are sequentially added into a 10L container, and stirred and reacted for 10 hours at the temperature of 30 ℃ to prepare a crude product of the polyethylene glycol acrylate, which can be directly used for the next reaction without purification.
5 kg of citrus essential oil was added to the crude polyethylene glycol acrylate product, followed by vigorous stirring for 1 hour, after which the reaction was placed under a 50W UV lamp and the reaction was continued for 5 hours with stirring to obtain a polymer-coated citrus flavor in a total amount of about 6.1 kg.
Example two:
1 kg (2mol) of polyethylene glycol monomethyl ether (mPEG500) with the molecular weight of 500, 200 g (2mol) of ethyl acrylate and 10g (0.1mol) of sodium carbonate are sequentially added into a 10L container, and stirred and reacted for 10 hours at the temperature of 30 ℃ to prepare a crude product of the polyethylene glycol acrylate, which can be directly used for the next reaction without purification.
5 kg of apple-flavored vegetable essential oil was added to the crude polyethylene glycol acrylate product, followed by vigorous stirring for 1 hour, after which the reaction system was placed under a 50W UV lamp and the reaction was continued for 5 hours with stirring to obtain a polymer-coated apple-flavored fragrance in a total amount of about 6.2 kg.
Example three:
1 kg (1mol) of polyethylene glycol monomethyl ether (mPEG1000) with the molecular weight of 1000, 86 g (1mol) of methyl acrylate and 6.9 g (0.05mol) of potassium carbonate are sequentially added into a 10L container, and stirred and reacted for 10 hours at the temperature of 30 ℃ to prepare a crude product of the polyethylene glycol acrylate, which can be directly used for the next reaction without purification.
To the crude polyethylene glycol acrylate product was added 5 kg of rose essential oil, followed by vigorous stirring for 1 hour, and then the reaction was exposed to 50W UV lamp while continuing to stir for 5 hours to obtain polymer-coated citrus flavor in a total amount of about 6.1 kg.
Example four:
1 kg (2mol) of polyethylene glycol monomethyl ether (mPEG500) with the molecular weight of 500, 200 g (2mol) of ethyl acrylate and 10g (0.1mol) of sodium carbonate are sequentially added into a 10L container, and stirred and reacted for 10 hours at the temperature of 30 ℃ to prepare a crude product of the polyethylene glycol acrylate, which can be directly used for the next reaction without purification.
5 kg of apple-flavor plant essential oil is added into the crude product of the polyethylene glycol acrylate, then the mixture is stirred vigorously for 1 hour, and then the reaction system is heated to 100 ℃ to react for 5 hours to obtain the polymer-wrapped apple-flavor flavoring agent, wherein the total amount of the polymer-wrapped apple-flavor flavoring agent is about 6.2 kg.
Example five:
1 kg (2mol) of polyethylene glycol monomethyl ether (mPEG500) with the molecular weight of 500, 200 g (2mol) of ethyl acrylate and 10g (0.1mol) of sodium carbonate are sequentially added into a 10L container, and stirred and reacted for 10 hours at the temperature of 30 ℃ to prepare a crude product of the polyethylene glycol acrylate, which can be directly used for the next reaction without purification.
5 kg of methyl laurate was added to the crude polyethylene glycol acrylate, followed by vigorous stirring for 1 hour, and then the reaction system was placed under a 50W UV lamp and the reaction was continued for 5 hours with stirring to obtain a polymer-encapsulated bay-type fragrance in a total amount of about 6.2 kg.
Example six:
8 g of methyl laurate and 2 g of glycerol were mixed to prepare an 80% glycerol solution of methyl laurate.
The initial concentration of methyl laurate in the fragrance prepared in control and example five was determined by liquid chromatography using 10g of the 80% glycerol solution of methyl laurate prepared in example six and 10g of the cinnamon fragrance prepared in example five, respectively.
The two samples were then placed in an exposed environment, maintained at ambient temperature and pressure, and the remaining methyl laurate concentration was measured every 10 days. The relative residual ratio is calculated according to the following formula:
relative residual ratio residual methyl laurate concentration/initial methyl laurate concentration
The final test results were as follows:
| 10 days | 20 days | 30 days | 40 days | 50 days | 60 days | 70 days | 80 days | 90 days | |
| EXAMPLE six | 57％ | 33％ | 21％ | 16％ | 11％ | 9％ | 8％ | 7％ | 6％ |
| EXAMPLE five | 92％ | 86％ | 81％ | 76％ | 72％ | 69％ | 67％ | 65％ | 64％ |
As can be seen from the above table, the volatilization speed of methyl laurate in the polymer-encapsulated methyl laurate perfume prepared in example five is significantly lower than that of the control group, which fully proves that the perfume slow-release technology provided by the present invention can effectively reduce the volatilization speed of perfume, and achieve the slow-release effect.
Claims (9)
1. A method for preparing essence and spice slow release is characterized in that: the method specifically comprises the following steps:
firstly, preparing a wrapping material monomer, namely performing ester exchange reaction on methyl acrylate or ethyl acrylate and polyethylene glycol monomethyl ether under an alkaline condition, mixing the methyl acrylate or the ethyl acrylate and the polyethylene glycol monomethyl ether in a reaction bottle, adding a catalytic amount of alkali, without any solvent, and reacting for 10 hours at 20-40 ℃ to obtain a crude product of the polyethylene glycol acrylate;
and secondly, fully and uniformly mixing the crude product of the polyethylene glycol acrylate prepared in the last step with the perfume, then carrying out polymerization reaction on an alkenyl unit of the polyethylene glycol acrylate, and simultaneously wrapping perfume molecules in a polymer chain, thereby obtaining the polymer-wrapped perfume.
2. The method for preparing essence and flavor slow release according to claim 1, wherein the method comprises the following steps: in the first step, the mass ratio of the acrylate to the polyethylene glycol amine monomethyl ether is 1-1.2: 1.
3. the method for preparing essence and flavor sustained release according to claim 1 or 2, characterized in that: in the first step, the polyethylene glycol monomethyl ether is selected from one or more of polyethylene glycol monomethyl ethers with molecular weight of 200-1000.
4. The method for preparing essence and flavor slow release according to claim 3, wherein the method comprises the following steps: the polyethylene glycol monomethyl ether is one or more selected from mPEG200, mPEG300, mPEG400, mPEG500, mPEG600, mPEG800 and mPEG 1000.
5. The method for preparing essence and flavor slow release according to claim 1, wherein the method comprises the following steps: in the first step, the alkali is selected from one or more of potassium carbonate, sodium carbonate, potassium hydroxide and sodium hydroxide, and the mass ratio of the alkali to the acrylate is 0.1-0.02: 1.
6. the method for preparing essence and flavor slow release according to claim 1, wherein the method comprises the following steps: in the second step, during the polymerization reaction, the mass ratio of the polyethylene glycol acrylate to the perfume is 1: 2-10, preferably 1: 5.
7. the method for preparing essence and flavor sustained release according to claim 1 or 6, wherein: in the second step, mechanical stirring was employed during the polymerization reaction, and vigorous stirring was carried out at room temperature for 1 hour.
8. The method for preparing essence and flavor slow release according to claim 1, wherein the method comprises the following steps: in the second step, the polymerization reaction is carried out at a high temperature of 100-120 ℃.
9. The method for preparing essence and flavor slow release according to claim 1, wherein the method comprises the following steps: in the second step, ultraviolet light is used for the polymerization.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010189735.9A CN111349518A (en) | 2020-03-18 | 2020-03-18 | Essence and spice slow-release preparation method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010189735.9A CN111349518A (en) | 2020-03-18 | 2020-03-18 | Essence and spice slow-release preparation method |
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| Publication Number | Publication Date |
|---|---|
| CN111349518A true CN111349518A (en) | 2020-06-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202010189735.9A Pending CN111349518A (en) | 2020-03-18 | 2020-03-18 | Essence and spice slow-release preparation method |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5211959A (en) * | 1990-01-11 | 1993-05-18 | Japan Atomic Energy Research Institute | Processes for producing slow-release powders |
| WO2004041232A1 (en) * | 2002-11-01 | 2004-05-21 | The Procter & Gamble Company | Perfume polymeric particles |
| CN1708285A (en) * | 2002-11-01 | 2005-12-14 | 宝洁公司 | Rinse-off personal care compositions comprising anionic and/or nonionic perfume polymeric particles |
| CN101289533A (en) * | 2008-06-13 | 2008-10-22 | 中山大学 | Method for synthesizing polyethyleneglycol monomethyl ether metacrylic acid ester |
-
2020
- 2020-03-18 CN CN202010189735.9A patent/CN111349518A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5211959A (en) * | 1990-01-11 | 1993-05-18 | Japan Atomic Energy Research Institute | Processes for producing slow-release powders |
| WO2004041232A1 (en) * | 2002-11-01 | 2004-05-21 | The Procter & Gamble Company | Perfume polymeric particles |
| CN1708285A (en) * | 2002-11-01 | 2005-12-14 | 宝洁公司 | Rinse-off personal care compositions comprising anionic and/or nonionic perfume polymeric particles |
| CN101289533A (en) * | 2008-06-13 | 2008-10-22 | 中山大学 | Method for synthesizing polyethyleneglycol monomethyl ether metacrylic acid ester |
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Inventor after: Liu Shichao Inventor after: Zhou Lihua Inventor before: Zhou Lihua |
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