CN111423477A - Polyol glucoside and preparation method and application thereof - Google Patents
Polyol glucoside and preparation method and application thereof Download PDFInfo
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- CN111423477A CN111423477A CN202010468167.6A CN202010468167A CN111423477A CN 111423477 A CN111423477 A CN 111423477A CN 202010468167 A CN202010468167 A CN 202010468167A CN 111423477 A CN111423477 A CN 111423477A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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- 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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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Abstract
The invention relates to the technical field of cosmetics and medicines, in particular to a polyol glucoside and a preparation method and application thereof. The present invention allows the obtained moisturizing compound to be used for the preparation of cosmetic or pharmaceutical agents by preparing a series of compounds having a moisturizing function, and the cosmetic or pharmaceutical agents in the present invention are not particularly limited. For example, the skin softening lotion can be a washing-off type cosmetic such as a softening lotion, a nourishing lotion, a massage cream, a skin moistening lotion, a gel, a nourishing cream, a facial mask, jelly or shower gel shampoo and the like, and can also be a medicinal preparation product such as a cream, an ointment, a cream, a plaster or a spray and the like; it can be used as sensitive skin, and can be added into infant and children cosmetics for reducing irritation.
Description
Technical Field
The invention relates to the technical field of cosmetics, in particular to a polyol glucoside and a preparation method and application thereof.
Background
The research shows that the polyol glucoside compound has higher moisture retention than the traditional moisture retention agent (such as glycerin), and can effectively improve the symptoms of itching and desquamation caused by dry skin after being applied. The eye cream has very little stimulation to human bodies (eyes and skin), and can relieve the stimulation of other substances to the human bodies when being compatible; the biodegradability is good; has excellent ecological and toxicological properties of sterilization, enzyme activity improvement and the like.
A common polyol glucoside compound is BGlycol glucoside, glycerol glucoside, and the like. The conventional preparation methods in the prior art comprise the following steps: direct glycosidation, solvent, transglycosidation, indirect synthesis, or enzymatic catalysis. Wherein the direct glycosidation method comprises, for example, bromoacetylation of glucose to obtain bromoacetylated glucose crystals, adding into ethylene glycol, and adding dried Ag2CO3Shaking, adding anhydrous benzene, standing, removing Ag salt, and separating the mixture. Extracting with anhydrous benzene for several times to remove glycol, concentrating and crystallizing the extractive solution to obtain glycol glucoside, and performing deacetylation reaction by Fischer method to obtain glycol glucoside crystal. The method can also be used for simultaneously synthesizing other polyol glucoside such as glycerol. The methods have certain technical defects, and have the problems of solvent residue and heavy metal ion residue, and the residues have certain irritation to the skin.
Therefore, in order to solve the existing situation, how to prepare a polyol glucoside compound with small irritation and remarkable moisturizing effect, so that the polyol glucoside compound can be used as a cosmetic or pharmaceutical agent, is a problem to be solved at present.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: a polyol glucoside compound with small irritation and remarkable moisturizing effect can be prepared and can be used as a cosmetic or pharmaceutical agent.
In order to solve the technical problems, the invention adopts the technical scheme that:
the invention provides a polyol glucoside, which has the following structural formula:
the invention also relates to a preparation method of the polyol glucoside, which comprises the following steps:
step 1: adding 1, 3-propanediol or 1, 3-butanediol and glucose into a reactor, and heating until the glucose is completely dissolved;
step 2: after glucose is completely dissolved, adding an acid catalyst into the reactor, keeping the temperature at 95-120 ℃, and carrying out a reduced pressure reaction at 0.08 Mp;
and step 3: after the reaction is carried out for 6 hours, the condenser does not divide water, the reaction is finished, an acid neutralizer is added into the reactor, the pH value of a reaction system in the reactor is adjusted to 4.5-6.5, and the reaction system is cooled to 15-30 ℃ to prepare the 1,3 propylene glycol glucoside or 1,3 butylene glycol glucoside.
The invention has the beneficial effects that: the polyol glucoside prepared by the invention is generated by directly reacting 1,3 propylene glycol or 1,3 butanediol with glucose under the condition of an acid catalyst, has the advantages of simple reaction steps and conditions, no chemical solvent residue and the like, and has better moisture retention property compared with the 1,3 propylene glycol glucoside and the 1,3 butanediol glucoside, and the like of glycerol and reported humectants of low-carbon polyol glucoside.
Detailed Description
In order to explain the technical content, the objects and the effects of the present invention in detail, the following description will be given with reference to the embodiments.
The most key concept of the invention is as follows: combining 1,3 propanediol or 1,3 butanediol with glucose to prepare 1,3 propanediol glucoside or 1,3 butanediol glucoside under the conditions of high temperature, acidic catalyst and reduced pressure. The obtained 1, 3-propylene glycol glucoside or 1, 3-butylene glycol glucoside has skin moisturizing effect.
The invention provides a polyol glucoside, which has the following structural formula:
the invention also relates to a preparation method of the polyol glucoside, which comprises the following steps:
step 1: adding 1, 3-propanediol or 1, 3-butanediol and glucose into a reactor, and heating until the glucose is completely dissolved;
step 2: after glucose is completely dissolved, adding an acid catalyst into the reactor, keeping the temperature at 95-120 ℃, and carrying out a reduced pressure reaction at 0.08 Mp;
and step 3: after the reaction is carried out for 6 hours, the condenser does not divide water, the reaction is finished, an acid neutralizer is added into the reactor, the pH value of a reaction system in the reactor is adjusted to 4.5-6.5, and the reaction system is cooled to 15-30 ℃ to prepare the 1,3 propylene glycol glucoside or 1,3 butylene glycol glucoside.
Preferably, in the step 1 of the method for preparing the polyol glucoside, the molar ratio of the 1, 3-propanediol or the 1, 3-butanediol to the glucose is 10: 1 to 2: 1.
Preferably, in the step 1 of the method for preparing the polyol glucoside, the molar ratio of the 1, 3-propanediol or the 1, 3-butanediol to the glucose is 8: 1 to 4: 1.
Preferably, in the above method for preparing polyol glucoside, step 2 specifically comprises:
after glucose is completely dissolved, adding an acid catalyst into the reactor, keeping the temperature at 95-115 ℃, and carrying out a reduced pressure reaction.
Preferably, in the method for preparing polyol glucoside, the acidic catalyst is one of hydrochloric acid, sulfuric acid, phosphoric acid and p-toluenesulfonic acid.
Preferably, in the method for producing a polyol glucoside, the acid neutralizer is at least one of potassium hydroxide, sodium hydroxide and sodium carbonate.
The above 1, 3-propanediol glucoside or 1, 3-butanediol glucoside has an application for preparing a cosmetic agent having moisturizing effect.
Example 1
Weighing 40g of glucose and 160g of 1, 3-butanediol (the molar ratio of the 1, 3-butanediol to the glucose is 8: 1), putting into a reactor, starting heating at 95 ℃, adding 0.1N concentrated sulfuric acid into the reactor until the glucose is completely dissolved, starting vacuum to perform reduced pressure reaction, adjusting the pH of the system to 4.5 by using 0.3% sodium hydroxide after the reaction is finished, distilling out redundant 1, 3-butanediol by using a film evaporator, and cooling to 15 ℃ to obtain 52g of 1, 3-butanediol glucoside, wherein the yield is 92.8%.
Example 2
Weighing 50g of glucose and 150g of 1, 3-butanediol (the molar ratio of the 1, 3-butanediol to the glucose is 6: 1), putting into a reactor, starting heating at 110 ℃, adding 0.15N of p-toluenesulfonic acid into the reactor until the glucose is completely dissolved, starting vacuum to perform reduced pressure reaction, adjusting the pH of the system to 5.2 by using 0.25% potassium hydroxide after the reaction is finished, distilling out redundant 1, 3-butanediol by using a film evaporator, and cooling to 25 ℃ to obtain 67g of 1, 3-butanediol glucoside, wherein the yield is 95.7%.
Example 3
Weighing 50g of glucose and 126.7g of 1, 3-propanediol (the molar ratio of the 1, 3-propanediol to the glucose is 6: 1), putting into a reactor, starting the heating temperature to be 105 ℃, adding 0.15N of sulfuric acid into the reactor until the glucose is completely dissolved, starting vacuum to perform reduced pressure reaction, adjusting the pH of the system to 5.0 by using 0.2% sodium hydroxide after the reaction is finished, distilling out redundant 1, 3-propanediol by using a film evaporator, cooling to 25 ℃ to obtain 60g of 1, 3-propanediol glucoside, wherein the yield is 90.9%.
Example 4
Weighing 100g of glucose and 168.9g of 1, 3-propanediol (the molar ratio of the 1, 3-propanediol to the glucose is 4: 1), putting into a reactor, starting the heating temperature to 110 ℃, adding 0.2N of p-toluenesulfonic acid into the reactor until the glucose is completely dissolved, starting vacuum to perform reduced pressure reaction, adjusting the pH of the system to 5.2 by using 0.2% potassium hydroxide after the reaction is finished, distilling out the redundant 1, 3-propanediol by using a thin film evaporator, cooling to 25 ℃ to obtain 121g of 1, 3-propanediol glucoside, wherein the yield is 91.7%.
Application example 1
The application of the 1, 3-butanediol glucoside prepared in example 1 in cosmetics is that the glucoside prepared in example 1 is applied in moisturizing essence, and the formula is shown in table 1:
TABLE 1
The process flow comprises the following steps:
1. accurately weighing the phase A1, 2, 3, 4 and 5, putting the phase A into an emulsifying pot, heating to 85 ℃, and keeping the temperature and stirring for 1 hour;
2. cooling to 60 ℃, adding the dissolved phase B into the system, and stirring for 30 minutes;
3. cooling to 40 ℃, putting the phase C into an emulsifying pot, stirring for 10 minutes, and taking out of the pot.
Comparative example 1:
the formula and preparation method of the moisturizing essence cosmetic of comparative example 1 are similar to those of application example 1, except that the essence C component is replaced with glycerin.
Application example 2
The application of 1, 3-butanediol glucoside prepared in example 2 in cosmetics is to apply the glucoside prepared in example 2 in moisturizing spray water, and the formula is shown in table 2:
TABLE 2
The process flow comprises the following steps:
1. accurately weighing the phase A1, the phase A2 and the phase A3, putting the phase A into an emulsifying pot, heating the phase A to 85 ℃, and stirring the phase A for 1 hour under the condition of heat preservation;
2. cooling to 60 ℃, adding the dissolved phase B into the system, and stirring for 30 minutes;
3. cooling to 40 ℃, putting the phase C into an emulsifying pot, stirring for 10 minutes, and taking out of the pot.
Comparative example 2:
the formulation, preparation method and application example 2 of the moisturizing spray cosmetic of comparative example 2 were similar, except that the moisturizing lotion C component was replaced with ethylene glycol glucoside.
Application example 3
The application of the 1, 3-propylene glycol glucoside prepared in example 3 in cosmetics is that the glucoside prepared in example 3 is applied in a moisture mask, and the formula is shown in table 3:
TABLE 3
The process flow comprises the following steps:
1. accurately weighing the phase A, putting the phase A into an emulsifying pot, heating to 85 ℃, and stirring for 1 hour under the condition of heat preservation;
2. accurately weighing phase B, putting the dissolved phase B into phase A, and homogenizing and stirring for 1 hour;
3. cooling to 50 deg.C, adding phase C into emulsifying pot, stirring for 10 min, and taking out.
Comparative example 3:
the formula, preparation method and application example 3 of the moisturizing mask cosmetic of comparative example 3 were similar, except that the mask C component was replaced with glycerin.
Application example 4
The application of the 1, 3-propylene glycol glucoside prepared in example 3 in cosmetics is to apply the glucoside prepared in example 3 in moisturizing cream, and the formula is shown in table 4:
TABLE 4
The process flow comprises the following steps:
1. accurately weighing the phase A, putting the phase A into an emulsifying pot, heating to 85 ℃, and stirring for 1 hour under the condition of heat preservation;
2. accurately weighing phase B, heating to 85 deg.C, adding into phase A, homogenizing and stirring for 1 hr;
3. cooling to 50 deg.C, adding phase C into emulsifying pot, stirring for 10 min, and taking out.
Comparative example 4:
the formulation, preparation method and application example 4 of the cream cosmetic of comparative example 4 were similar except that the cream C ingredient was replaced with ethylene glycol glucoside.
Evaluation methods of moisture retention and irritation:
the cosmetics prepared in examples 1 to 4 and comparative examples 1 to 4 were applied to the forearm of 100 subjects, respectively, 50 men and 50 women in total, aged 20 to 40 years, and 30 minutes after the application. At that time, the subjects evaluated the moisture retention and irritation on the skin according to the following evaluation criteria, the scores were summed up, and the total score was divided by 100 times the number of persons to obtain an average score.
The evaluation of moisture retention (average point) is preferably 8.0 or more, more preferably 9.0 or more, further preferably 9.5 or more, and particularly preferably 10 or more.
< evaluation of skin moisturizing Property >
10 min: the skin is firmer than before use.
And 5, dividing: the skin is softer than before use.
0 minute: as before the application.
The evaluation of the irritation (average point) is preferably 8.0 or more, more preferably 9.0 or more, further preferably 9.5 or more, and particularly preferably 10 or more.
< criteria for evaluating skin irritation Properties >
10 min: no skin irritation.
And 5, dividing: slight irritation to the skin was observed.
0 minute: skin irritation was clearly observed.
And (4) water retention test:
the cosmetics prepared in examples 1 to 4 and comparative examples 1 to 4 were each taken at 50g and placed in 50 ml cups. The weight of the mouthpiece (50X 40mm) was measured (weight W). Rockwool cubes are made to absorb aqueous solutions by soaking a rock wool cube in an aqueous solution placed in a cup. After 24 hours, the piece of rock wool was removed and the weight of the piece of rock wool was measured (weight W24). Comparative example experiments were carried out in the same manner as described above. The moisture retention rate was calculated by the following formula to evaluate the moisture retention rate.
Water retention (%) (W24-W) ÷ 50X 100
Preferably, the water retention is greater than or equal to 80%, more preferably greater than or equal to 90%, and greater than or equal to 95%. It is particularly preferred that this ratio is greater than 98%.
TABLE 4
| Experimental group | Moisture retention | Irritation property | Water Retention ratio (%) |
| Application example 1 | 10 | 10 | 94 |
| Application example 2 | 10 | 10 | 96 |
| Application example 3 | 10 | 10 | 95 |
| Application example 4 | 10 | 10 | 93 |
| Comparative example 1 | 7 | 8 | 80 |
| Comparative example 2 | 8.5 | 8.5 | 86 |
| Comparative example 3 | 7.5 | 8 | 81 |
| Comparative example 4 | 8.5 | 8.0 | 85 |
From the above results, it can be seen that 1, 3-propanediol glucoside or 1, 3-butanediol glucoside has better moisture retention and less irritation than glycerin and ethylene glycol glucoside when used as a formula of a moisturizing essence, a moisturizing spray, a moisturizing mask or a moisturizing cream.
In summary, the present invention allows the obtained moisturizing compound to be used for the preparation of cosmetic or pharmaceutical agents by preparing a series of compounds having a moisturizing function, and the cosmetic or pharmaceutical agents in the present invention are not particularly limited. For example, the skin softening lotion can be a washing-off type cosmetic such as a softening lotion, a nourishing lotion, a massage cream, a skin moistening lotion, a gel, a nourishing cream, a facial mask, jelly or shower gel shampoo and the like, and can also be a medicinal preparation product such as a cream, an ointment, a cream, a plaster or a spray and the like; it can be used as sensitive skin, and can be added into infant and children cosmetics for reducing irritation.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all equivalent modifications made by the present invention in the specification or directly or indirectly applied to the related technical field are included in the scope of the present invention.
Claims (8)
1. A polyol glucoside has the following structural formula:
2. a method for preparing a polyol glucoside of claim 1, comprising the steps of:
step 1: adding 1, 3-propanediol or 1, 3-butanediol and glucose into a reactor, and heating until the glucose is completely dissolved;
step 2: after glucose is completely dissolved, adding an acid catalyst into the reactor, keeping the temperature at 95-120 ℃, and carrying out a reduced pressure reaction at 0.08 Mp;
and step 3: after the reaction is carried out for 6 hours, the condenser does not divide water, the reaction is finished, an acid neutralizer is added into the reactor, the pH value of a reaction system in the reactor is adjusted to 4.5-6.5, and the reaction system is cooled to 15-30 ℃ to prepare the 1,3 propylene glycol glucoside or 1,3 butylene glycol glucoside.
3. The method for producing a polyhydric alcohol glucoside of claim 2, wherein in the step 1, the molar ratio of 1, 3-propanediol or 1, 3-butanediol to glucose is 10: 1 to 2: 1.
4. The method for producing a polyhydric alcohol glucoside of claim 2, wherein in the step 1, the molar ratio of 1, 3-propanediol or 1, 3-butanediol to glucose is 8: 1 to 4: 1.
5. The method for preparing polyol glucoside according to claim 2, wherein the step 2 specifically comprises:
after glucose is completely dissolved, adding an acid catalyst into the reactor, keeping the temperature at 95-115 ℃, and carrying out a reduced pressure reaction.
6. The method of claim 2, wherein the acidic catalyst is one of hydrochloric acid, sulfuric acid, phosphoric acid, and p-toluenesulfonic acid.
7. The method of claim 2, wherein the acid neutralizer is at least one of potassium hydroxide, sodium hydroxide, or sodium carbonate.
8. Use of the polyol glucoside of claim 1 for the preparation of a cosmetic agent with moisturizing properties.
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Cited By (3)
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| CN114947173A (en) * | 2022-06-24 | 2022-08-30 | 湖北中烟工业有限责任公司 | Glucoside-containing electronic cigarette atomizing agent and preparation method and application thereof |
| CN116004747A (en) * | 2022-09-07 | 2023-04-25 | 福建农林大学 | Method for extracting 2, 3-butanediol monoglucoside from Raffaelea lauricola |
| KR102544469B1 (en) * | 2022-10-24 | 2023-06-20 | 주식회사 디제이씨 | Cosmetic Additives Composition and Manufacturing Method of the Same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114947173A (en) * | 2022-06-24 | 2022-08-30 | 湖北中烟工业有限责任公司 | Glucoside-containing electronic cigarette atomizing agent and preparation method and application thereof |
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| KR102544469B1 (en) * | 2022-10-24 | 2023-06-20 | 주식회사 디제이씨 | Cosmetic Additives Composition and Manufacturing Method of the Same |
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