CN108299571A - A kind of derivatives of hyaluronic acids and the preparation method and application thereof - Google Patents
A kind of derivatives of hyaluronic acids and the preparation method and application thereof Download PDFInfo
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- CN108299571A CN108299571A CN201710017994.1A CN201710017994A CN108299571A CN 108299571 A CN108299571 A CN 108299571A CN 201710017994 A CN201710017994 A CN 201710017994A CN 108299571 A CN108299571 A CN 108299571A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
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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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
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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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- 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
- A61Q19/08—Anti-ageing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
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Abstract
The present invention provides a kind of derivatives of hyaluronic acids of phosphatide, which can be obtained by Sodium Hyaluronate and the reaction of phosphatide reagent.Phosphatide derivatives of hyaluronic acids of the present invention has the effects that better moisturizing, promotes absorption, bio-compatible, activating cell, anti-oxidant, delaying skin aging.The analog derivative has good compatibility in other cosmetic materials, bulk pharmaceutical chemicals etc., and the compound is enable to be widely used in the fields such as cosmetics, drug and health products.
Description
Technical field
The present invention relates to cosmetics, medicine fields, and in particular to and it is the functional derivatives of hyaluronic acids containing phospholipid fragments,
And its application in household chemicals, drug.
Background technology
Hyaluronic acid（Hyaluronic Acid, HA）Also known as sodium hyaluronate, molecule are with gluconic acid-N- acetylaminos
Glucose is the acid linear mucopolysaccharide of linear polymeric of disaccharide units composition, many groups be largely present in organism
It knits, such as the cytoplasm of humans and animals, vitreum, umbilical cord, skin, knuckle synovia and rooster comb soft connective tissue are extracellular
In matrix, separated from bovine vitreous body earliest.HA aqueous solutions have good Water-saving effect and lubricating action, excellent
Different viscoplasticity and biocompatibility is adjusted the synthesis of collagen, reduces the formation of scar, and the repetition disaccharide unit knot of HA
Structure is consistent in all species tissues, no species difference, non-immunogenicity, safe and non-toxic.Since HA contains multiple hydroxyls
Base and carboxyl can form hydrogen bond with hydrone, there is very strong water retaining function, and HA is widely present in skin and other tissues
Bio-molecules, therefore be known as ideal natural moisturizing factor.Special HA boiomacromolecule structure, physicochemical property and
Extensive physiological activity makes HA be used widely in cosmetics, medicine, organizational project and clinic.
The structure of hyaluronic acid is as follows：
Phosphatide（Phospholipid）, also referred to as phospholipid, Phospholipids refer to the lipid phosphatide containing phosphoric acid, there is C, H, O, N, P five
Kind element composition.Phosphatide has polarity phosphate-based simultaneously（Hydrophilic head）With nonpolar fatty acid chain（Hydrophobic tail）, make it
With unique physicochemical properties, such as there is emulsification property, moisture-keeping function, solubilising and peptizaiton, therefore in medicine, change
It is widely used in the fields such as cosmetic, detergent.Phosphatide is the important composition of cell membrane in animal and plant cells, nuclear membrane and lipid film
Ingredient is widely present in the organizational interface and body fluid of human body, all contains phosphatide in all cells of human body, it is the work that sustains life
Dynamic basic substance.Phosphatide maintains metabolism, basic metabolism and hormonal balanced secretion, enhances human body to activating cell
Immunity and regeneration power, great effect can be played.It can enhance mental, stable nerve, balance endocrine.Phosphatide has
Anti-oxidation efficacy can make cell activation and make skin fitness, therefore be known as " the third nutrition arranged side by side with protein, vitamin
Element ".
However, HA is sensitive to strong acid, highly basic, heat and hyaluronidase, the residence time is short in vivo, easy diffusion, degradable
Etc. characteristics, greatly limit its application, in order to give full play to the effect of HA, HA must be modified with cationic molecule,
And the molecule containing phosphatide can be such that HA absorbs more complete closer to human body component, and using absorbefacient effect of phosphatide, inhale
It receives speed to accelerate, and reduces the dosage of HA.In addition, after HA forms compound with phosphatide, health-care effect, the antioxygen of phosphatide are turned into
With, to cell activation effect, to skin fitness effect can also be enhanced, the two can play synergistic effect, protect skin jointly
It slows down aging.Furthermore it is also possible to as needed, add other nutritional ingredients or active constituent, utilize the moisturizing of HA, bio-compatible
Property, viscoplasticity, lubrication etc. and phosphatide emulsification property, moisture-keeping function, slow releasing function, enhancing active constituent, solubilising and dispersion etc.
Various cosmetics, pharmaceuticals and health products are made in effect.
Invention content
The present invention provides a kind of phosphatide hyaluronic acid, the compound structure general formula such as formulas（a）It is shown：
Wherein： R1、R2、R3Be each, independently of the other H, benzyl, carbon atom number be 1-18 alkyl, N, N- dimethyl fat alkane
Acyl propane diamine base.
Synthetic schemes step and thinking provided by the invention containing phospholipid fragments are as follows：
（1）The synthesis of 2- hydroxyl -3- chloropropyl di-phosphate ester sodium：Sodium dihydrogen phosphate is added to the water, with salt acid for adjusting pH to 3-
4, then epoxychloropropane is added dropwise, wherein the amount ratio of the substance of sodium dihydrogen phosphate and epoxychloropropane is 1:At 2.4,80 DEG C,
It is stirred to react 6h, ethyl acetate extraction obtains 2- hydroxyl -3- chloropropyl di-phosphate ester sodium；
（2）The synthesis of sodium phosphate amphoteric surfactant：2- hydroxyl -3- chloropropyl di-phosphate ester sodium is soluble in water, use hydrogen
Aqueous solution of sodium oxide adjusts PH to 9-10, then the ethanol solution of corresponding aminated compounds is added dropwise, wherein 2- hydroxyls -3- chlorine
The amount ratio of the substance of propyl di-phosphate ester sodium and aminated compounds is 1:1, it is stirred at reflux reaction 10h, aqueous acetone solution recrystallizes,
Obtain sodium phosphate amphoteric surfactant；
（3）The synthesis of phosphatide hyaluronic acid：Sodium phosphate amphoteric surfactant is soluble in water, 50% hydroxide is used in combination
Sodium water solution adjusts pH=12, and Sodium Hyaluronate stirring is added, and is stored at room temperature three days, product then is precipitated with ethyl alcohol, acetone is used in combination
Washing, it is dry to get phosphatide hyaluronic acid.
The phosphatide hyaluronic acid that the present invention will provide has preferable conditioning performance to the cardability of hair, can be used as
The improver of hair for shampoo, hair conditioner, is washed and protects one-piece type shampoo, hair conditioner, mascara detergent etc..
The phosphatide hyaluronic acid that the present invention will provide, can be quickly formed by acting on human skin by one layer is close to skin
Protecting film makes skin have good moistening effect, while starting anti-oxidation function, plays the role of delay skin aging.
In addition, compound of the present invention has good compatibility with general cosmetic material, with surface-active
The compatibility of the other components such as agent, grease, solvent, antioxidant is fine, with cosmetic material mixing emulsify after, can make cream, frost,
The matrix such as breast are fine and smooth uniformly, store not stratified, impermeable, stable dosage forms for a long time.
Specific implementation mode by the following examples is again described in further detail the above of the present invention, but
It is not limited only to embodiment below.The present invention includes under above-mentioned technological thought, according to ordinary skill knowledge and strong hand
The various replacements or change that section is made, should all be included within the scope of the invention.
Specific implementation mode
In order to be better understood from the essence of invention, invention content, but the content of present invention is described in detail below by example
It is not limited thereto.
Embodiment 1
The preparation method of phosphatide hyaluronic acid 1a：
（1）By 15.60 g（0.1 mol）Sodium dihydrogen phosphate dihydrate is added in 20.0 g water, with salt acid for adjusting pH to 3-4, then by
It is added dropwise to 22.28 g（0.24 mol）Epoxychloropropane, at 80 DEG C, be stirred to react 6h, acquired solution acetic acid second after reaction
Ester repeatedly extracts, and is then spin-dried for aqueous solution, and vacuum drying obtains the thick white 2- hydroxyls -3- chloropropyl di-phosphate esters of 25.10 g
Sodium；
（2）By 15.28 g（0.05 mol）2- hydroxyl -3- chloropropyl di-phosphate ester sodium be dissolved in 20 g water, be added 250 mL
Flask in, adjust pH to 9-10, then 18.53 g with sodium hydrate aqueous solution（0.05 mol）N- stearyl-N ',
N '-dimethylated propyl diethylenetriamines are dissolved in the ethyl alcohol of 80 mL, at 50 DEG C, are added dropwise in flask, and 1h is dripped off, and is then heated up, stirring
Back flow reaction 10h, the solution after reaction rotate water and ethyl alcohol, are recrystallized with aqueous acetone solution, filter and dry, obtain 24.82
The sodium phosphate amphoteric surfactant of g white solids；
（3）By 10.55 g（0.0156 mol）The sodium phosphate amphoteric surfactant of gained is dissolved in 3 mL water, is added 0.25
The 2M sodium hydroxide solutions of mL adjust pH, and 1 g is then added（It is calculated as 0.0026 mol with disaccharide unit）Sodium Hyaluronate stirs
To glue, three days are stood at room temperature, ethyl alcohol is then added, product is precipitated, acetone cleaning product is used in combination, filter, it is dry, obtain 1.11
G white solids are to get phosphatide hyaluronic acid 1a.
Embodiment 2
The preparation method of phosphatide hyaluronic acid 1b：
（1）By 15.60 g（0.1 mol）Sodium dihydrogen phosphate dihydrate is added in 20.0 g water, with salt acid for adjusting pH to 3-4, then by
It is added dropwise to 22.28 g（0.24 mol）Epoxychloropropane, at 80 DEG C, be stirred to react 6h, acquired solution acetic acid second after reaction
Ester repeatedly extracts, and is then spin-dried for aqueous solution, and vacuum drying obtains the thick white 2- hydroxyls -3- chloropropyl di-phosphate esters of 25.10 g
Sodium；
（2）By 15.28 g（0.05 mol）2- hydroxyl -3- chloropropyl di-phosphate ester sodium be dissolved in 20 g water and be added 250 mL's
In flask, pH is adjusted to 9-10, then 15.23 g with sodium hydrate aqueous solution（0.05 mol）N, N- dimethyl-N '-bay
Acyl group -1,3- propane diamine is dissolved in the ethyl alcohol of 80 mL, at 50 DEG C, is added dropwise in flask, and 1h is dripped off, and is then heated up, stirring
10 h of back flow reaction, the solution after reaction rotate water and ethyl alcohol, are recrystallized with aqueous acetone solution, filter and dry, obtain 21.18
The sodium phosphate amphoteric surfactant of g white solids；
（3）By 9.52 g（0.0156 mol）The sodium phosphate amphoteric surfactant of gained is dissolved in 3 mL water, is added 0.25
The 2M sodium hydroxide solutions of mL adjust pH, and 1 g is then added（It is calculated as 0.0026 mol with disaccharide unit）Sodium Hyaluronate stirs
To glue, three days are stood at room temperature, ethyl alcohol is then added, product is precipitated, acetone cleaning product is used in combination, filter, it is dry, obtain 1.07
G white solids are to get phosphatide hyaluronic acid 1b.
Embodiment 3-9
The preparation method of phosphatide hyaluronic acid 1c-i：With reference to 1 method of embodiment, a series of phosphatide hyaluronic acid production is prepared
Product.Relevant product information is shown in Table 1：
Embodiment 10
By carding force, the conditioning effect of sample is measured and evaluated.Specific method is：Comb is measured using instron tensile strength tester passing through
When hair fiber, hair resistance being overcome, being stretching in the strength for formulating institute's load in displacement, front and back hair is used by sample to be tested
Beam wet method, dry carding strength percentage change evaluate the nursing efficacy of sample.By the phosphatide containing isodose working substance
Hyaluronic acid sample 1a-i is added separately in carding force test formulations system, carries out the cardability test of sample.
The carding force test formulations system of sample addition is shown in Table 2：
Testing procedure is as follows：
（1）12% prepared in advance of topknot（Active matter content, it is the same below）The aqueous cleaning of AES and 1.6% CAB, test are wet
Comb benchmark carding force R0, naturally dry is then hung, dry comb benchmark carding force F is tested0；
（2）Topknot is cleaned with sample to be tested, tests wet comb carding force R1, naturally dry is then hung, dry comb carding force is tested
F1；
（3）Calculate separately the wet comb carding force percentage change of topknot i.e.（R1-R0）/R0］ × 100% does comb carding force variation hundred
Point rate be（F1-F0）/F0］ × 100%, the wet comb of comparative product and dry comb performance, infer product conditioning performance.
Explanation：Each sample surveys 3 beam topknot of Duplicate Samples, and each topknot parallel testing 10 times is averaged.
Phosphatide hyaluronic acid（1a-i）Carding force test result is shown in Table 3：
It can be seen that obtained phosphatide hyaluronic acid has preferable adjustment effect, and dry comb property to the cardability of hair
It can be more preferable than wet comb performance.
Embodiment 11
By skin, the measurement of moistening effect is carried out.Specifically test method is：It is visited with Corneometer CM825 moisture measurements
Head measures subject and tests, and test point is inner forearm and facial mark point, uses sample（2.0%）Front and back moisture contains
Amount, each test point is parallel to be surveyed 5 times, is then averaged, and is carried out continuously 30 days, is as a result used moisture arbitary
Units (a.u.) is indicated.
Phosphatide hyaluronic acid（1a-i）The test result of moistening effect is shown in Table 4：
It can be seen that phosphatide derivatives of hyaluronic acids performance of keeping humidity is better than hyaluronic acid.
Embodiment 12
A kind of emulsifiable paste moisturizing, antipruritic ointment formula such as table 5：
The ointment can be used for alleviating itch caused by seasonal dry skin, or for improving allergic skin itch.
Claims (6)
1. a kind of derivatives of hyaluronic acids of phosphotidic of claim, which is characterized in that the structure of the phosphotidic hyaluronic acid is logical
Shown in formula such as formula (a)：
(a)
Wherein：R1, R2, R3 be each, independently of the other H, benzyl, carbon atom number be 1-18 alkyl, N, N- dimethyl fat
Alkane acyl propane diamine base.
2. the preparation method of phosphatide hyaluronic acid according to claim 1, is characterized in that, includes the following steps：
（1）The synthesis of 2- hydroxyl -3- chloropropyl di-phosphate ester sodium：Sodium dihydrogen phosphate is added to the water, with salt acid for adjusting pH to 3-
4, then epoxychloropropane is added dropwise, wherein the amount ratio of the substance of sodium dihydrogen phosphate and epoxychloropropane is 1:At 2.4,80 DEG C,
It is stirred to react 6h, ethyl acetate extraction is spin-dried for, dry, obtains 2- hydroxyl -3- chloropropyl di-phosphate ester sodium；
（2）The synthesis of sodium phosphate amphoteric surfactant：2- hydroxyl -3- chloropropyl di-phosphate ester sodium is soluble in water, use hydrogen
Aqueous solution of sodium oxide adjusts PH to 9-10, then the ethanol solution of corresponding aminated compounds is added dropwise, wherein 2- hydroxyls -3- chlorine
The amount ratio of the substance of propyl di-phosphate ester sodium and aminated compounds is 1:1, it is stirred at reflux reaction 10h, aqueous acetone solution recrystallizes,
Obtain sodium phosphate amphoteric surfactant；
（3）The synthesis of phosphatide hyaluronic acid：Sodium phosphate amphoteric surfactant is soluble in water, it is used in combination sodium hydroxide water-soluble
Liquid adjusts pH=12, and Sodium Hyaluronate stirring is added, and is stored at room temperature three days, product then is precipitated with ethyl alcohol, acetone is used in combination to wash,
Drying is to get phosphatide hyaluronic acid.
3. according to phosphatide hyaluronic acid in claim 1, which is characterized in that the compound can be widely applied to daily use chemicals, medicine
Equal fields.
4. according to claim 3, which can be used as a kind of dry comb conditioner of hair, be applied to personal care articles.
5. according to claim 3, which can be used as skin conditioning agent, be applied to personal care articles.
6. according to claim 3, which is applied to skin preparation as skin conditioning agent.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101715457A (en) * | 2007-04-24 | 2010-05-26 | 丘比株式会社 | Cationized hyaluronic acid and/or salt thereof, method for producing the same, and hair modifying agent, cuticle repairing agent, skin modifying agent and cosmetic preparation each using the same |
| CN101820853B (en) * | 2007-10-30 | 2012-09-12 | 南京华狮化工有限公司 | Use of long carbon chain quaternary ammonium salt phosphoric acid ester as conditioner for hair |
| CN103450254A (en) * | 2013-08-23 | 2013-12-18 | 中国石油大学(华东) | Preparation method of ultralow interfacial tension surfactant used in field of oilfield chemistry |
-
2017
- 2017-01-11 CN CN201710017994.1A patent/CN108299571A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101715457A (en) * | 2007-04-24 | 2010-05-26 | 丘比株式会社 | Cationized hyaluronic acid and/or salt thereof, method for producing the same, and hair modifying agent, cuticle repairing agent, skin modifying agent and cosmetic preparation each using the same |
| CN101820853B (en) * | 2007-10-30 | 2012-09-12 | 南京华狮化工有限公司 | Use of long carbon chain quaternary ammonium salt phosphoric acid ester as conditioner for hair |
| CN103450254A (en) * | 2013-08-23 | 2013-12-18 | 中国石油大学(华东) | Preparation method of ultralow interfacial tension surfactant used in field of oilfield chemistry |
Non-Patent Citations (2)
| Title |
|---|
| 傅明连: ""新型磷酸酯两性表面活性剂的合成与性能研究"", 《莆田学院学报》 * |
| 李明勇等: ""3-氯-2-羟基丙磷酸钠的合成研究"", 《精细化工中间体》 * |
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