CN109010101A - A kind of phosphoramidite chemical sun-screening agent and wide spectrum suncream and preparation method thereof - Google Patents
A kind of phosphoramidite chemical sun-screening agent and wide spectrum suncream and preparation method thereof Download PDFInfo
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- CN109010101A CN109010101A CN201811081516.8A CN201811081516A CN109010101A CN 109010101 A CN109010101 A CN 109010101A CN 201811081516 A CN201811081516 A CN 201811081516A CN 109010101 A CN109010101 A CN 109010101A
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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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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Abstract
A kind of phosphoramidite chemical sun-screening agent and wide spectrum suncream and preparation method thereof, the invention discloses a kind of broad spectrum sunscreens, the sun-screening agent includes the own ester of 3- methoxy cinnamic acid (2- ethyl) and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester, the mass ratio of the two are 0.5:5~5:0.5；The phosphoramidite chemical sun-screening agent can be strong the absorption area ultraviolet (UV) B and the area UVA light, the ratio for absorbing the absorbance of the area ultraviolet (UV) B and the area UVA light is 0.5:5~5:0.5.Broad spectrum sunscreen prepared by the present invention includes the own ester of 3- methoxy cinnamic acid (2- ethyl), the own ester of 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl), pot marigold extracting solution, tea polyphenols, Tween 80, zinc oxide, vaseline, glycerol and distilled water.Sun-screening agent of the present invention is used for the suncream being prepared after acceptable carrier on a effective amount of cosmeceutical, not only has the characteristics that wide spectrum is sun-proof, and do not have irritation to skin, without toxic side effect, safety in utilization is higher.
Description
Technical field
Prevent the present invention relates to a kind of daily use chemicals skin-protection product and preparation method thereof more particularly to a kind of sun-screening agent and its containing this
Shine the suncream and its their preparation method of agent.
Background technique
It for the mankind, crosses and skin is exposed under burning sun for a long time, due to directly connecing for strong ultraviolet light and skin
Touching, will lead to its sunburn or it is tanned in turn result in skin injury, show spotting out, skin relaxation or wrinkle, can cause when serious
The cancerations such as melanoma tumors, therefore, effectively sun-proof is very necessary.Although there are many miscellaneous suncream on the market,
The disadvantages of it is short that there are timeliness, and effectively sun-proof range is relatively narrow, and artificial molecule long-time service can generate unknown adverse effect.
Summary of the invention
For the prior art, the present invention sufficiently makes up the deficiency of present similar product, and the advantage of comprehensive multiple product provides
A kind of wide spectrum suncream has highly desirable wide spectrum sun-proof result.Wide spectrum suncream of the present invention is mainly by ultraviolet light
Reflection and absorption, effective protection skin, using effect are preferable.
In order to solve the above-mentioned technical problem, a kind of phosphoramidite chemical sun-screening agent proposed by the present invention, the component and weight for including
Than being: the weight ratio of the own ester of 3- methoxy cinnamic acid (2- ethyl) and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester
For 0.5:5~5:0.5；The own ester of 3- methoxy cinnamic acid (2- ethyl) and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) oneself
The general formula of ester is as follows:
Wherein, when being expressed as 3- methoxy cinnamic acid (2- ethyl) own ester, substituent R is the acid of R1, is expressed as 3,5- bis-
When -4 hydroxycinnamic acid of methoxyl group (2- ethyl) own ester, substituent R is the acid of R2；
The phosphoramidite chemical sun-screening agent absorbs the light in the area ultraviolet (UV) B and the area UVA, absorbs ultraviolet (UV) B area's light and absorbs purple
The ratio of the absorbance of the area outside line UVA light is 0.5:5~5:0.5.
The own ester of the 3- methoxy cinnamic acid (2- ethyl) and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester
Preferred weight ratio is 1:1, and the ratio for absorbing ultraviolet (UV) B area's light and absorbing the absorbance of the area ultraviolet (UV) A light is 1:1.
A kind of preparation method for preparing above-mentioned phosphoramidite chemical sun-screening agent proposed in the present invention, comprising the following steps:
Prepare 3- methoxy cinnamic acid (2- ethyl) own ester: by the acid of the R1 of 1.0 equivalents and the 2- ethyl hex- of 1.2 equivalents
1- alcohol is dissolved in 10 equivalent tetrahydrofurans and 3 equivalent n,N-Dimethylformamide, and the thionyl of 1.2 equivalents is then added dropwise thereto
Chlorine obtains mixture；It heats the mixture to 70 DEG C to react at least 2 days, until TLC shows that the acid of the R1 of 1.0 equivalent of raw material is complete
After totally disappeared consumption, mixture is washed with water；Organic phase is concentrated to and is used thin layer chromatography, is used It washes
It is de-, obtain 3- methoxy cinnamic acid (2- ethyl) own ester；
Prepare 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester: by the acid of the R2 of 1.0 equivalents and 1.2 equivalents
2- ethyl hex- 1- alcohol is dissolved in 10 equivalent tetrahydrofurans and 3 equivalent n,N-Dimethylformamide, and 1.2 are then added dropwise thereto and works as
The thionyl chloride of amount, obtains mixture；It heats the mixture to 70 DEG C to react at least 2 days, until TLC shows 1.0 equivalent of raw material
R2 acid completely consume after, mixture is washed with water；Organic phase is concentrated to and is used thin layer chromatography, is usedElution, obtains 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester.
A kind of wide spectrum suncream proposed in the present invention, including component and its weight percent are as follows:
The preparation method of above-mentioned wide spectrum suncream, comprising the following steps:
Zinc oxide is added in glycerol and is uniformly mixing to obtain mixture A by step 1；
Tween 80, pot marigold extracting solution and tea polyphenols are added in distilled water step 2, are uniformly mixing to obtain mixture B；
Mixture B is added in mixture A by step 3, add vaseline, 3- methoxy cinnamic acid (2- ethyl) oneself
Ester and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester, stirs evenly, obtains mixture C；
Step 4 emulsifies the mixture C of step 3, as gained；
Above steps carries out at ambient temperature and pressure.
Compared with prior art, the beneficial effects of the present invention are:
With highly desirable wide spectrum sun-proof result.This product mainly passes through the reflection and absorption to ultraviolet light, effective protection
Skin, using effect are preferable.The primary raw material of this product is small to skin irritation, not will cause skin allergy, also secondary without poison
Effect, safety in utilization are higher.
Detailed description of the invention
Fig. 1 is that concentration is two primary chemical sun-screening agents in methylene chloride in wide spectrum suncream prepared by the present invention
Ultraviolet spectrogram when 0.045mmol/L.
Specific embodiment
Technical solution of the present invention is described in further detail in the following with reference to the drawings and specific embodiments, it is described specific
Embodiment is only explained the present invention, is not intended to limit the invention.
A kind of phosphoramidite chemical sun-screening agent proposed by the present invention, the component and weight ratio for including are: by 3- methoxy cinnamic acid
(2- ethyl) own ester and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester are that 0.5:5~5:0.5 is assembled according to quality,
Wherein, the own ester of 3- methoxy cinnamic acid (2- ethyl) and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester
General formula it is as follows:
The phosphoramidite chemical sun-screening agent absorbs the light in the area ultraviolet (UV) B and the area UVA, absorbs ultraviolet (UV) B area's light and absorbs purple
The ratio of the absorbance of the area outside line UVA light is 0.5:5~5:0.5.When mass ratio is 1:1, the ratio of absorbance is 1:1.
Prepare above-mentioned phosphoramidite chemical sun-screening agent, including the own ester of preparation 3- methoxy cinnamic acid (2- ethyl) and 3,5- dimethoxy
- 4 hydroxycinnamic acid of base (2- ethyl) own ester, wherein 3- methoxy cinnamic acid (2- ethyl) own ester prepare when use substituent R for
The acid of R1,3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester use substituent R for the acid of R2 when preparing, preparation process
It is essentially identical: respective acids (1.0 equivalent) and 2- ethyl hex- 1- alcohol (1.2 equivalent) are dissolved in 10mL THF and 3mL DMF, it is small
SOCl is added dropwise in the heart2(1.2 equivalent).Heat the mixture to 70 DEG C of reactions 2 days or the longer time.TLC shows that raw material completely consumes
Afterwards, mixture is washed with water.Organic phase is concentrated to and is used thin layer chromatography, is used Elution.I.e.
3- methoxy cinnamic acid (2- ethyl) own ester and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester, yield are obtained respectively
For
The component and its weight for the wide spectrum suncream that phosphoramidite chemical sun-screening agent of the present invention is used to be prepared in suncream
Percentage are as follows: 3- methoxy cinnamic acid (2- ethyl) own ester is 0.5-5.0,3,5- dimethoxy-4 ' hydroxycinnamic acids (2- ethyl)
Own ester is 0.5-5.0, and pot marigold extracting solution is 5.0-10.0, tea polyphenols 5.0-10.0, Tween 80 10.0-20.0, oxidation
Zinc is 3.0-5.0, and vaseline 3.0-10.0, glycerol 3.0-10.0, surplus is distilled water.
The preparation method of above-mentioned wide spectrum suncream, comprising the following steps: stirred firstly, zinc oxide is added in glycerol
It is even to obtain mixture A, it is spare；Tween 80, pot marigold extracting solution and tea polyphenols are added in distilled water, mixing is uniformly mixing to obtain
Object B, it is spare；Said mixture B is added in mixture A, vaseline, 3- methoxy cinnamic acid (2- ethyl) own ester are added
With 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester, stirs evenly, obtain mixture C；Finally, by mixture C cream
Changing is gained.
Embodiment 1:
At ambient temperature and pressure, zinc oxide is added in glycerol according to each component and content specified in the following table 1 respectively
It is uniformly mixing to obtain mixture A, it is spare；Tween 80, pot marigold extracting solution and tea polyphenols are added in distilled water, are stirred evenly
It is spare to mixture B；Said mixture B is added in mixture A, vaseline, 3- methoxy cinnamic acid (2- second are added
Base) own ester and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester stirs evenly, obtains mixture C；Finally, will mix
Closing object C emulsification is gained.
Embodiment 2-24:
Respectively according to each component and content specified in the following table 1 and the method for repeating embodiment 1.
Table 1
Sun-proof efficient test:
500 volunteers, each 20 people of embodiment user are selected at random, an arm smears suncream, and one does not apply,
Daily under sunlight shine 1 hour, compare two arms tanned degree and evaluation suncream whether allergy, continuous use 25
It the results are shown in Table 2, and sun-proof result effect is divided into three grades:
It is obvious: to smear the arm of suncream and the arm comparison for not smearing suncream obviously, smear the arm skin of suncream
Skin is pale, non-stimulated, and the tanned sunburn of arm for not smearing suncream is obvious.
Obvious: the arm for smearing suncream compares obvious, smearing suncream with the arm for not smearing suncream
Arm skin color it is more black, it is non-stimulated；The arm for not smearing suncream is tanned obvious.
Unobvious: the arm for smearing suncream is unobvious with the arm comparison for not smearing suncream, smears the hand of suncream
Skin of arm color and the arm no significant difference for not smearing suncream.
The irritation of suncream is divided into two grades:
Irritant: there is allergic reaction in the arm for smearing suncream.
It is nonirritant: to smear the arm of suncream without allergic reaction.
Table 2
In the wide spectrum suncream that the present invention is prepared, when the own ester of 3- methoxy cinnamic acid (2- ethyl) and 3,5- dimethoxy
It is 1 that -4 hydroxycinnamic acid of base (2- ethyl) own ester, which is degree,；When 1, effect is best, for what is tanned severely with skin tanning
Effective percentage up to 100%, and proportion is reduced or improved, effective percentage is below 100%.When 3- methoxycinnamate
Sour (2- ethyl) own ester and 3, when 5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester degree is more than 5%, by reality
Certain irritation can be generated to skin by applying 6 result of example and can be seen that suncream, thus 3- methoxy cinnamic acid (2- ethyl) oneself
Ester and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester.And change other percentage composition contents in suncream,
The physical property of this product can be had an impact, the sun-proof effective percentage of this product is not generated and is significantly affected.It can by above-mentioned using effect
To find out, skin sunburn can be effectively prevent tanned using suncream provided by the present invention.
It is obtained from the test result of table 2, the own ester of 3- methoxy cinnamic acid (2- ethyl) and 3,5- dimethoxy-4 ' hydroxyl meat
Cinnamic acid (2- ethyl) own ester can absorb Ultraviolet B region (UVB, 285-320nm) according to mass percent about 1:1 composition strongly
With the light of a-quadrant (UVA, 320-400nm) (the ultraviolet region C (UVC, < 285nm) due to all being absorbed by ozone layer, so sun-proof
Frost need not design thus), it is as shown in Figure 1 with the sun-proof feature of wide spectrum.One good suncream should be able to absorb ultraviolet light strongly
The light in the section B (UVB, 285-320nm) and the section A (UVA, 320-400nm), Fig. 1 are in wide spectrum suncream prepared by the present invention
Ultraviolet spectrogram of two primary chemical sun-screening agents when concentration is 0.045mmol/L in methylene chloride.Two as shown in Figure 1
Primary chemical sun-screening agent extraordinary can cover entire UVA, UVB wave band, experiments have shown that being ideal suncream.
Although above in conjunction with attached drawing, invention has been described, and the invention is not limited to above-mentioned specific implementations
Mode, the above mentioned embodiment is only schematical, rather than restrictive, and those skilled in the art are at this
Under the enlightenment of invention, without deviating from the spirit of the invention, many variations can also be made, these belong to of the invention
Within protection.
Claims (5)
1. a kind of phosphoramidite chemical sun-screening agent, which is characterized in that the component and weight ratio for including are: 3- methoxy cinnamic acid (2- second
Base) weight ratio of own ester and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester is 0.5:5~5:0.5；
The general formula of the own ester of 3- methoxy cinnamic acid (2- ethyl) and 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester is such as
Under:
Wherein, when being expressed as 3- methoxy cinnamic acid (2- ethyl) own ester, substituent R is the acid of R1, is expressed as 3,5- dimethoxy
When -4 hydroxycinnamic acid of base (2- ethyl) own ester, substituent R is the acid of R2；
The phosphoramidite chemical sun-screening agent absorbs the light in the area ultraviolet (UV) B and the area UVA, absorbs ultraviolet (UV) B area's light and absorbs ultraviolet light
The ratio of the absorbance of the area UVA light is 0.5:5~5:0.5.
2. phosphoramidite chemical sun-screening agent according to claim 1, which is characterized in that the 3- methoxy cinnamic acid (2- ethyl) oneself
Ester and 3, the mass ratio of 5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester are 1:1, absorb ultraviolet (UV) B area's light and absorb
The ratio of the absorbance of the area ultraviolet (UV) A light is 1:1.
3. a kind of preparation method for preparing phosphoramidite chemical sun-screening agent as claimed in claim 1 or 2, comprising the following steps:
Prepare 3- methoxy cinnamic acid (2- ethyl) own ester: by the acid of the R1 of 1.0 equivalents and the 2- ethyl hex- 1- alcohol of 1.2 equivalents
It is dissolved in 10 equivalent tetrahydrofurans and 3 equivalent n,N-Dimethylformamide, the thionyl chloride of 1.2 equivalents is then added dropwise thereto,
Obtain mixture；It heats the mixture to 70 DEG C to react at least 2 days, until the acid of the R1 for 1.0 equivalent of raw material that TLC is shown disappears completely
After consumption, mixture is washed with water；Organic phase is concentrated to and is used thin layer chromatography, is used Elution, obtains
To 3- methoxy cinnamic acid (2- ethyl) own ester；
Prepare 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester: by the acid of the R2 of 1.0 equivalents and the 2- second of 1.2 equivalents
Base hex- 1- alcohol is dissolved in 10 equivalent tetrahydrofurans and 3 equivalent n,N-Dimethylformamide, and 1.2 equivalents are then added dropwise thereto
Thionyl chloride obtains mixture；It heats the mixture to 70 DEG C to react at least 2 days, until TLC shows the R2 of 1.0 equivalent of raw material
Acid completely consume after, mixture is washed with water；Organic phase is concentrated to and is used thin layer chromatography, uses PE:EA=5:1-1:1
Elution, obtains 3,5- dimethoxy-4 ' hydroxycinnamic acid (2- ethyl) own ester.
4. a kind of wide spectrum suncream, which is characterized in that including component and its weight percent are as follows:
5. a kind of preparation method for preparing wide spectrum suncream as claimed in claim 4, which comprises the following steps:
Zinc oxide is added in glycerol and is uniformly mixing to obtain mixture A by step 1；
Tween 80, pot marigold extracting solution and tea polyphenols are added in distilled water step 2, are uniformly mixing to obtain mixture B；
Mixture B is added in mixture A by step 3, add vaseline, 3- methoxy cinnamic acid (2- ethyl) own ester and
3,5- dimethoxy-4 ' hydroxycinnamic acids (2- ethyl) own ester, stirs evenly, obtains mixture C；
Step 4 emulsifies the mixture C of step 3, as gained；
Above steps carries out at ambient temperature and pressure.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811081516.8A CN109010101A (en) | 2018-09-17 | 2018-09-17 | A kind of phosphoramidite chemical sun-screening agent and wide spectrum suncream and preparation method thereof |
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| CN201811081516.8A CN109010101A (en) | 2018-09-17 | 2018-09-17 | A kind of phosphoramidite chemical sun-screening agent and wide spectrum suncream and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110339076A (en) * | 2019-07-19 | 2019-10-18 | 中山爱护日用品有限公司 | A kind of sunscreen composition and the preparation method and application thereof with broad-spectrum light protective action |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101203278A (en) * | 2005-04-19 | 2008-06-18 | 默克专利股份有限公司 | UV protection |
| CN107929124A (en) * | 2017-11-30 | 2018-04-20 | 林俊浩 | One kind isolation sunscreen composition |
| US20180200167A1 (en) * | 2015-07-30 | 2018-07-19 | Truth Aesthetics LLC | Topical Skin Care Composition Providing Broad Spectrum Sunscreen |
-
2018
- 2018-09-17 CN CN201811081516.8A patent/CN109010101A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101203278A (en) * | 2005-04-19 | 2008-06-18 | 默克专利股份有限公司 | UV protection |
| US20180200167A1 (en) * | 2015-07-30 | 2018-07-19 | Truth Aesthetics LLC | Topical Skin Care Composition Providing Broad Spectrum Sunscreen |
| CN107929124A (en) * | 2017-11-30 | 2018-04-20 | 林俊浩 | One kind isolation sunscreen composition |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110339076A (en) * | 2019-07-19 | 2019-10-18 | 中山爱护日用品有限公司 | A kind of sunscreen composition and the preparation method and application thereof with broad-spectrum light protective action |
| CN110339076B (en) * | 2019-07-19 | 2022-10-04 | 中山爱护日用品有限公司 | Sun-screening composition with broad-spectrum light protection effect and preparation method and application thereof |
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Application publication date: 20181218 |