CN1944470A - P-acetyl amino benzoyl chitosan compound and its preparing method - Google Patents
P-acetyl amino benzoyl chitosan compound and its preparing method Download PDFInfo
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- CN1944470A CN1944470A CN 200610159656 CN200610159656A CN1944470A CN 1944470 A CN1944470 A CN 1944470A CN 200610159656 CN200610159656 CN 200610159656 CN 200610159656 A CN200610159656 A CN 200610159656A CN 1944470 A CN1944470 A CN 1944470A
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Abstract
The present invention discloses p-acetamino benzoyl chitosan compound and its preparation process. The compound in 1 g/L concentration acetic acid solution has ultraviolet absorption spectrum with great absorption peak at 273 nm and molecular weight of 110-130 KD. The preparation process includes the following steps: dissolving p-amino benzoic acid in distilled water, adding excessive acetic anhydride via stirring and suction filtering; vacuum drying the filter cake to obtain p-acetamino benzoic acid; adding anhydrous alcohol and slightly excessive sulfoxide chloride and ultrasonically reaction to operate p-acetamino benzoyl chloride; adding anhydrous acetic acid solution of chitosan, soaking the product in mixed solvent of anhydrous alcohol and anhydrous ethyl ether, and suction filtering; and Soxlet extracting the filter cake in acetone and vacuum drying to the p-acetamino benzoyl chitosan compound. The compound is used as antitan additive in cosmetics.
Description
Technical field
The present invention relates to the functional deriv of the chitosan chemical modification of chitin kind, it is applied to the daily-use chemical industry technology industry, belongs to technical field of polymer chemistry.
Background technology
As everyone knows, chitosan is the deacetylated product of chitin, and it is to have unique a kind of alkaline polysaccharide in the organic sphere in a large number.Because of the effect of intramolecularly and intermolecular hydrogen bonding, chitosan only is dissolved in acid and acidic aqueous solution.Contain modifiable groups such as a large amount of hydroxyls, amino on the chitosan molecule chain, can obtain various derivatives, therefore can enlarge its range of application by chemical modification with specific function.For example, biocompatibility that the chitosan tool is good and film-forming properties, bacteria resistance function and whitening effect, preserve moisture, function such as moisture absorption, irritation cell regeneration, but only can be dissolved in the tart solution, limit its range of application.Usually people introduce quaternary ammonium salt, alkyl, mineral acid etc. on chitosan molecule, just improve the solvability or the flocculence of chitosan.A kind of para-amino benzoic acid compound is arranged, its to keep skin health, lubricate, delay wrinkle Exposure to Sunlight appears, resists, alleviate skin because of burn, scald the shouting pain that causes etc. positive effect arranged.But para-amino benzoic acid causes sensitivity easily, especially to heredity skin, and the easier allergy that causes.If the amino in the para-amino benzoic acid is got up with acetyl protection, makes acetaminol.Phenyl ring in this compound and C=O are chromophores, do not report so far and introduce acetaminol on chitosan molecule.
Summary of the invention
The objective of the invention is to overcome the shortcoming separately of above-claimed cpd, a kind of novel chitosan derivatives is provided.This chitosan derivatives will have uv-absorbing and cosmetic result, and it can be used as the additive of sun care preparations.
The objective of the invention is to be finished by following technical scheme, developed a kind of acetaminol chitosan compound, it is characterized in that: its structure is,
Wherein n represents between the 500-600, and phenyl ring in its structure and C=O are the functional group of adding lustre to, and this compound is that the ultra-violet absorption spectrum 273nm place of 1g/L acetum has big absorption peak in concentration; The materialization technical indicator of this compound: the white powder solid, water-soluble and ethylene glycol, molecular weight are 110-130KD.
A kind of preparation method of described acetaminol chitosan compound, described preparation process is as follows:
(1) para-amino benzoic acid with weighing is dissolved in the 50-65 ℃ of distilled water hot suction filtration;
(2) filtrate is poured in the beaker, again filtrate is put in 50-65 ℃ the water-bath, when treating that the filtrate temperature reaches 50-65 ℃, to wherein adding excessive acetic anhydride via rapidly, stir the appearance precipitation, continue to stir after 30-60 minute, from water-bath, take out beaker, be put into indoor naturally cooling;
(3) cool to room temperature, at room temperature suction filtration;
(4) get filter cake, vacuum-drying again obtains paraacetaminobenzoic acid;
(5) get a certain amount of dry paraacetaminobenzoic acid of crossing and put into three-necked bottle, the anhydrous diethyl ether that adds 30ml, add excessive a little sulfur oxychloride again, put into water temperature and be in 20-40 ℃ the ultrasonic washer, ultra-sonic oscillation 10-60 minute, reaction product was an acetaminol chlorine;
(6) reaction product in cooling (5) step is got the 0.5g chitosan and is dissolved in the 10ml anhydrous acetic acid to 0-30 ℃, again it is added in the three-necked bottle, and at 5--45 ℃ of following ultra-sonic oscillation 1-3.5 hour, standing over night;
(7) reaction product with (6) step adds a large amount of acetone, makes product acetaminol chitosan be precipitated out suction filtration;
(8) use the mixed solvent of dehydrated alcohol and anhydrous diethyl ether to soak after 12-24 hour again, suction filtration is got filter cake;
(9) this filter cake that again (8) is gone on foot carries out Soxhlet extraction 24-30 hour with acetone, gets acetaminol chitosan product after the vacuum-drying.
The processing condition of described (1), (7), the suction filtration in (8) step are: dried by the fire 1-3 hour in 50-65 ℃ of baking oven with filter flask or B, at the 50-65 ℃ of reaction solution of using the water pump suction filtration down, suction filtration is over, and rapidly filtrate is poured in the clean beaker again.
Described para-amino benzoic acid: sulfur oxychloride: chitosan, three's the weight ratio that feeds intake is 1-5: 3-9: 1.
The dehydrated alcohol in described (8) step and the mixed volume ratio of anhydrous diethyl ether are 1: 1-10.
The Soxhlet in described (9) step is extracted, and its processing condition are: 55-65 ℃ of heating in water bath, extracted 24-30 hour.
The vacuum-drying in described (9) step, its processing condition are: under 30-50 ℃, vacuum tightness is 8 * 10
4Pa, dry 12-24 hour.
A kind of described acetaminol chitosan compound is as the application in the preparation sun care preparations additive.
Positively effect of the present invention is: since earlier the amino in the para-amino benzoic acid with acetyl protection, acetaminol is incorporated into prepares novel chitosan derivatives on the chitosan molecule again.This chitosan derivatives arrives the 273nm place because of its ultraviolet absorption peak red shift, and has uv-absorbing and cosmetic result, and it can be used as the additive of sun care preparations.
The present invention prepares acetylbenzoic acid by para-amino benzoic acid and acetic anhydride.The paraacetaminobenzoic acid that drying is crossed is put into three-necked bottle, add a certain amount of anhydrous diethyl ether, add sulfur oxychloride again, put in the ultrasonic washer of 30 ℃ of water temperatures, reacted 10 minutes.In three-necked bottle, add the certain amount of chitosan acetic acid solution, 5 ℃ of-45 ℃ of following ultra-sonic oscillation 1 hour, because ultrasonic wave is to the promoter action of inhomogeneous reaction, ultrasonic energy produces " cavity effect " this effect and has formed in reaction system and be enough to cause or the high energy center of accelerated reaction; Hyperacoustic second-order effect such as mechanical oscillation, diffusion, emulsification simultaneously, smash etc. helps the thorough mixing of reactant, can promote the carrying out that reacts greatly.After ultra-sonic oscillation are handled, standing over night.After reaction is finished, add a large amount of acetone product be precipitated out, filter, soak suction filtration after 24 hours with the mixed solvent of dehydrated alcohol and anhydrous diethyl ether again, again the filter cake behind the suction filtration is carried out Soxhlet with acetone and extracted 24 hours, after the vacuum-drying product.
Products therefrom acetaminol chitosan of the present invention and cationic, anionic property and amphoterics have excellent compatibility, have good moisture absorption and moisture retention, also have the ultraviolet ability that absorbs, add to and can have the ultraviolet function of absorption in the makeup.
The principal reaction that relates to of the present invention had three steps:
1), preparation paraacetaminobenzoic acid:
Diacetyl oxide is excessive, makes amino total overall reaction.
2), preparation acetaminol chlorine:
3), preparation acetaminol chitosan:
Description of drawings
Fig. 1 is the uv absorption spectra of the acetic acid solution of chitosan and prepared chitosan derivative.
Fig. 2 adds acetaminol chitosan derivatives uv-absorbing spectrogram in the sunscreen.
Fig. 3 does not add acetaminol chitosan derivatives uv-absorbing spectrogram in the sunscreen.
Shown in Figure 1: for the acetum with 1g/L is a solvent, it is 1 * 10 that chitosan and acetaminol chitosan are made concentration
-4The solution of g/ml records its uv absorption spectra.Wherein 1 is the infrared spectrogram of chitosan, and 2 is the infrared spectrogram of the derivative of chitosan.Analyze two infrared spectrums as seen, 1596cm in the chitosan infrared spectrum
-1The place is amino N-H formation vibration peak, 3400cm
-1Near belong to the absorption peak of O-H stretching vibration and N-H stretching vibration in the chitosan molecule, 1080cm
-1Neighbouring is the absorption peak of C-OH; Graft product is at 1734cm
-1The absorption peak of the stretching vibration of C=O, 1596cm appear in the place
-1Amino N-H formation vibration peak, place changes, at 1620cm
-1Near the absorption peak of acid amides stretching vibration has appearred, and 1080cm
-1The absorption peak of C-OH near does not change, and can know acetaminol chlorine by inference and mainly react on the amino of chitosan.
Fig. 2 uv-absorbing spectrogram has a maximum absorption peak at the 273nm place, and strong ultraviolet radiation absorption peak value is promptly arranged at the 273nm place.Absorbancy is 0.7 herein, and uv-absorbing can reach the 300nm place, has reached the UVB district.And Fig. 3 does not add the acetaminol chitosan, and the uv-absorbing spectrogram shows that the 240-350nm place does not have absorption peak substantially, and ultraviolet absorptivity is also very little.The difference of the addition of acetaminol chitosan, uv-absorbing intensity are also different.
Embodiment
Para-amino benzoic acid is dissolved in 60 ℃ of water, and hot suction filtration is poured filtrate in the beaker into, and reheat to 60 ℃ adds a certain amount of diacetyl oxide rapidly, stirs precipitation to occur, react 30 minutes, cools off suction filtration.Filter cake vacuum-drying obtains paraacetaminobenzoic acid.Get the dry paraacetaminobenzoic acid 1g that crosses and put into three-necked bottle, add a certain amount of anhydrous diethyl ether, add sulfur oxychloride again, put into the ultrasonic washer of 30 ℃ of water temperatures
[4,5]In, reacted 10 minutes.Be cooled to 25 ℃, the 0.5g chitosan is dissolved in the 10ml acetate, it is being added in three-necked bottle, and 25 ℃ of following ultra-sonic oscillation 1 hour, standing over night.After reaction is finished, add a large amount of acetone product is precipitated out, suction filtration uses the mixed solvent of dehydrated alcohol and anhydrous diethyl ether to soak suction filtration after 24 hours again, again the filter cake behind the suction filtration is carried out Soxhlet with acetone and extracted 24 hours, get product---acetaminol chitosan after the vacuum-drying.
Embodiment 2:
Get the dry paraacetaminobenzoic acid 1g that crosses and put into three-necked bottle, add a certain amount of anhydrous diethyl ether, add sulfur oxychloride again, put into the ultrasonic washer of 30 ℃ of water temperatures
[4,5]In, reacted 10 minutes.Be heated to 45 ℃, the 0.5g chitosan is dissolved in the 10ml acetate, it is being added in three-necked bottle, and 45 ℃ of following ultra-sonic oscillation 1 hour, standing over night.After reaction is finished, add a large amount of acetone product is precipitated out, suction filtration uses the mixed solvent of dehydrated alcohol and anhydrous diethyl ether to soak suction filtration after 24 hours again, again the filter cake behind the suction filtration is carried out Soxhlet with acetone and extracted 24 hours, get product---acetaminol chitosan after the vacuum-drying.
Embodiment 3:
Get the dry paraacetaminobenzoic acid 1g that crosses and put into three-necked bottle, add a certain amount of anhydrous diethyl ether, add sulfur oxychloride again, put into the ultrasonic washer of 30 ℃ of water temperatures
[4,5]In, reacted 10 minutes.Be cooled to 5 ℃, the 0.5g chitosan is dissolved in the 10ml acetate, it is being added in three-necked bottle, and 5 ℃ of following ultra-sonic oscillation 1 hour, standing over night.After reaction is finished, add a large amount of acetone product is precipitated out, suction filtration uses the mixed solvent of dehydrated alcohol and anhydrous diethyl ether to soak suction filtration after 24 hours again, again the filter cake behind the suction filtration is carried out Soxhlet with acetone and extracted 24 hours, get product-acetaminol chitosan after the vacuum-drying.
Embodiment 4:
Products therefrom acetaminol chitosan of the present invention and cationic, anionic property and amphoterics have the embodiment of good compatibility stability (after 7 days)
| Tensio-active agent (0.1g/ml) | 0.01g/ml products therefrom of the present invention | 0.05g/ml products therefrom of the present invention |
| Sodium dodecyl sulfate solution | Not stratified nothing precipitation | Not stratified nothing precipitation |
| Palmityl trimethyl ammonium chloride solution | Not stratified nothing precipitation | Not stratified nothing precipitation |
| Varion CDG-K solution | Not stratified nothing precipitation | Not stratified nothing precipitation |
Embodiment 5: products therefrom acetaminol chitosan of the present invention adds shampoo to
| Component | Weight ratio (part) |
| Dimethyl hydroxy methylene stearylamine trimethyl-glycine | 40 |
| The acetaminol chitosan | 2 |
| Lactic acid (10%) | 2 |
| Cetrimonium chloride (50%) | 5 |
| Deionized water | 51 |
Embodiment 6: products therefrom acetaminol chitosan of the present invention adds shampoo to
| Component | Weight ratio (part) |
| Sorbyl alcohol | 30 |
| Sodium lauryl sulfate | 5 |
| The acetaminol chitosan | 5 |
| | 1 |
| Essence | 1 |
| Water | 58 |
Implement 7: products therefrom acetaminol chitosan of the present invention adds shampoo to
| Component | Weight ratio (part) |
| Palmityl trimethyl ammonium chloride | 6 |
| The Soxylat A 25-7 stearate | 3 |
| Hexadecanol | 9 |
| Vaseline | 3 |
| The acetaminol chitosan | 3 |
| Propylene glycol | 15 |
| Essence | 2.5 |
| Sanitas | 0.5 |
| Purified Water | 58 |
Implement 8: the application example emulsion-type frost cream of products therefrom acetaminol chitosan of the present invention in sun care preparations: prescription one
| Component | Weight ratio (part) |
| Hexadecanol | 7 |
| Propylene glycol | 10 |
| Glycerol monosterate | 3 |
| The acetaminol chitosan derivatives | 10 |
| Sanitas | 0.5 |
| Spices | 0.5 |
| Purified Water | 69 |
Emulsion-type frost cream: prescription two
| Component | Weight ratio (part) |
| Vaseline | 20 |
| Silicone oil | 3 |
| Cross linked polyacrylate | 0.5 |
| Squalane | 10 |
| The acetaminol chitosan derivatives | 10 |
| Sanitas | 0.3 |
| Sodium hydroxide | 0.5 |
| Spices | 0.7 |
| Purified Water | 55 |
Emulsion-type frost cream: prescription three
| Component | Weight ratio (part) |
| Stearyl alcohol | 0.5 |
| Stearic acid | 5 |
| Water-soluble polypropylene acid | 0.3 |
| Glycerine | 5 |
| The acetaminol chitosan derivatives | 10 |
| Trolamine | 1.7 |
| Purified Water | 76.7 |
| Spices | 0.5 |
| Sanitas | 0.3 |
The production technique of above-mentioned sun care preparations: heat water to 70-85, add water-soluble formula material, get water after the dissolving fully.Other is mixed in the 50-65 heat of solution with oil, fat material and antioxidant, ultraviolet absorbers, in stirring down oil phase material is added to the aqueous phase mixing and emulsifying then, behind the homogeneous, stirs cooling, and in 40 adding spices and sanitass, packing obtains sunscreen.Use products therefrom acetaminol chitosan of the present invention to add in the makeup, resulting this sunscreen has the ultraviolet ability of absorption.See the contrast experiment's of Fig. 2 and 3 uv-absorbing spectrogram.
Those of ordinary skill in the art can understand, and in protection scope of the present invention, makes amendment for the foregoing description, and it all is possible adding and replacing, and it does not all exceed protection scope of the present invention.
Claims (8)
1 one kinds of acetaminol chitosan compounds is characterized in that: its structure is,
Wherein n is between 500-600, and phenyl ring in its structure and C=O are the functional group of adding lustre to, and this compound is that the ultra-violet absorption spectrum 273nm place of 1g/L acetum has big absorption peak in concentration; The materialization technical indicator of this compound: the white powder solid, water-soluble and ethylene glycol, molecular weight are 110-130KD.
2, the preparation method of the described acetaminol chitosan compound of a kind of claim 1, it is characterized in that: described preparation process is as follows:
(1) para-amino benzoic acid with weighing is dissolved in the 50-65 ℃ of distilled water hot suction filtration;
(2) filtrate is poured in the beaker, again filtrate is put in 50-65 ℃ the water-bath, when treating that the filtrate temperature reaches 50-65 ℃, to wherein adding excessive acetic anhydride via rapidly, stir the appearance precipitation, continue to stir after 30-60 minute, from water-bath, take out beaker, be put into indoor naturally cooling;
(3) cool to room temperature, at room temperature suction filtration;
(4) get filter cake, vacuum-drying again obtains paraacetaminobenzoic acid;
(5) get a certain amount of dry paraacetaminobenzoic acid of crossing and put into three-necked bottle, the anhydrous diethyl ether that adds 30ml, add excessive a little sulfur oxychloride again, put into water temperature and be in 20-40 ℃ the ultrasonic washer, ultra-sonic oscillation 10-60 minute, reaction product was an acetaminol chlorine;
(6) reaction product in cooling (5) step is got the 0.5g chitosan and is dissolved in the 10ml anhydrous acetic acid to 0-30 ℃, it is added in three-necked bottle, 5 again---45 ℃ following ultra-sonic oscillation 1-3.5 hour, standing over night;
(7) reaction product with (6) step adds a large amount of acetone, makes product acetaminol chitosan be precipitated out suction filtration;
(8) use the mixed solvent of dehydrated alcohol and anhydrous diethyl ether to soak after 12-24 hour again, suction filtration is got filter cake;
(9) this filter cake that again (8) is gone on foot carries out Soxhlet extraction 24-30 hour with acetone, gets acetaminol chitosan product after the vacuum-drying.
3, according to the preparation method of the described acetaminol chitosan compound of claim 2, it is characterized in that: described (1), (7) and the processing condition of suction filtration in (8) step all be: dried by the fire 1-3 hour in 50-65 ℃ of baking oven with filter flask or B, at the 50-65 ℃ of reaction solution of using the water pump suction filtration down, after being over, suction filtration rapidly filtrate is poured in the clean beaker again.
4, according to the preparation method of the described acetaminol chitosan compound of claim 2, it is characterized in that: described para-amino benzoic acid: sulfur oxychloride: chitosan, three's the weight ratio that feeds intake is 1-5: 3-9: 1.
5, according to the preparation method of the described acetaminol chitosan compound of claim 2, it is characterized in that: the dehydrated alcohol in described (8) step and the mixed volume ratio of anhydrous diethyl ether are 1: 1-10.
6, according to the preparation method of the described acetaminol chitosan compound of claim 2, it is characterized in that: the Soxhlet in described (9) step is extracted, and its processing condition are: 55-65 ℃ of heating in water bath, extracted 24-30 hour.
7, according to the preparation method of the described acetaminol chitosan compound of claim 2, it is characterized in that: the vacuum-drying in described (9) step, its processing condition are: under 30-50 ℃, vacuum tightness is 8 * 10
4Pa, dry 12-24 hour.
8, the described acetaminol chitosan compound of a kind of claim 1 is as the application in the preparation sun care preparations additive.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101596563A CN100463923C (en) | 2006-06-29 | 2006-09-29 | P-acetyl amino benzoyl chitosan compound and its preparing method |
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|---|---|---|---|
| CN200610045377.4 | 2006-06-29 | ||
| CN200610045377 | 2006-06-29 | ||
| CNB2006101596563A CN100463923C (en) | 2006-06-29 | 2006-09-29 | P-acetyl amino benzoyl chitosan compound and its preparing method |
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| CN100463923C CN100463923C (en) | 2009-02-25 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101775084A (en) * | 2010-04-01 | 2010-07-14 | 北京化工大学常州先进材料研究院 | Method for preparing organic-dissolvable photosensitive chitosan derivate |
| CN101649005B (en) * | 2009-09-09 | 2011-06-08 | 中国海洋大学 | Para aminobenzoyl chitosan and preparing method thereof |
| CN102153674A (en) * | 2011-03-15 | 2011-08-17 | 中国海洋大学 | Chitosan ester p-aminobenzoate and preparation method thereof |
| CN102198053A (en) * | 2011-05-25 | 2011-09-28 | 江南大学 | Synthesis and application of similar quaternized chitosan sunscreen |
| CN101255202B (en) * | 2007-12-12 | 2011-12-07 | 中国海洋大学 | p-benzoyl amido benzoyl chitosan and preparation thereof |
| CN104784741A (en) * | 2015-04-23 | 2015-07-22 | 武汉市思泰利医疗器械发展有限公司 | Functional medical dressing containing chitosan and hydrocolloid |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2639514B1 (en) * | 1988-11-30 | 1991-01-25 | Rhone Poulenc Sante | COMPOSITIONS FOR COATING FOOD ADDITIVES FOR RUMINANTS |
| JP3058009B2 (en) * | 1994-06-14 | 2000-07-04 | 日本製紙株式会社 | Chitosan derivatives, compositions for near-infrared absorbers comprising them and near-infrared absorbers |
| CN1623996A (en) * | 2004-03-19 | 2005-06-08 | 湖南科技大学 | N-acyl amino glucose and its preparation process |
-
2006
- 2006-09-29 CN CNB2006101596563A patent/CN100463923C/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101255202B (en) * | 2007-12-12 | 2011-12-07 | 中国海洋大学 | p-benzoyl amido benzoyl chitosan and preparation thereof |
| CN101649005B (en) * | 2009-09-09 | 2011-06-08 | 中国海洋大学 | Para aminobenzoyl chitosan and preparing method thereof |
| CN101775084A (en) * | 2010-04-01 | 2010-07-14 | 北京化工大学常州先进材料研究院 | Method for preparing organic-dissolvable photosensitive chitosan derivate |
| CN102153674A (en) * | 2011-03-15 | 2011-08-17 | 中国海洋大学 | Chitosan ester p-aminobenzoate and preparation method thereof |
| CN102153674B (en) * | 2011-03-15 | 2012-11-07 | 中国海洋大学 | P-aminobenzoate chitosan ester and preparation method thereof |
| CN102198053A (en) * | 2011-05-25 | 2011-09-28 | 江南大学 | Synthesis and application of similar quaternized chitosan sunscreen |
| CN102198053B (en) * | 2011-05-25 | 2013-01-23 | 江南大学 | Synthesis and application of similar quaternized chitosan sunscreen |
| CN104784741A (en) * | 2015-04-23 | 2015-07-22 | 武汉市思泰利医疗器械发展有限公司 | Functional medical dressing containing chitosan and hydrocolloid |
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