CN108721682A - A kind of laccol containing catechol group modifies synthetic method and its application of mesoporous silicon dioxide micro-sphere - Google Patents
A kind of laccol containing catechol group modifies synthetic method and its application of mesoporous silicon dioxide micro-sphere Download PDFInfo
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- CN108721682A CN108721682A CN201810633518.7A CN201810633518A CN108721682A CN 108721682 A CN108721682 A CN 108721682A CN 201810633518 A CN201810633518 A CN 201810633518A CN 108721682 A CN108721682 A CN 108721682A
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- silicon dioxide
- mesoporous silicon
- laccol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/02—Surgical adhesives or cements; Adhesives for colostomy devices containing inorganic materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
- A61L24/0036—Porous materials, e.g. foams or sponges
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/113—Silicon oxides; Hydrates thereof
- C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/04—Materials for stopping bleeding
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/01—Particle morphology depicted by an image
- C01P2004/04—Particle morphology depicted by an image obtained by TEM, STEM, STM or AFM
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/12—Surface area
Abstract
The present invention disclose it is a kind of containing catechol group laccol modification mesoporous silicon dioxide micro-sphere synthetic method and its application comprising following steps：A. the synthesis of mesoporous silicon dioxide micro-sphere：So that ethyl orthosilicate is carried out sol gel reaction in cetyl trimethylammonium bromide, ethylene glycol and sodium hydrate aqueous solution by a certain percentage and presoma is made, mesoporous silicon dioxide micro-sphere is obtained after high-temperature calcination；B. laccol modifies mesoporous silicon dioxide micro-sphere：Weigh a certain proportion of mesoporous silicon dioxide micro-sphere, γ-methacryloxypropyl trimethoxy silane and ethyl alcohol, it is added in a single-necked flask, 70 DEG C of 24 h of stirring, after centrifuge washing, a certain amount of azodiisobutyronitrile, laccol and ethyl alcohol, 70 DEG C of 24 h of stirring are added, centrifuge washing, it obtains laccol and modifies mesoporous silicon dioxide micro-sphere, it is internal containing 1 ~ 10 ducts nm and containing the catechol group of tissue adhension effect, it is a kind of hemostat having application prospect.
Description
Technical field
The present invention relates to a kind of, and the laccol containing catechol group modifies mesoporous silicon dioxide micro-sphere, belongs to functional polymer material
Expect technical field.
Background technology
In war and common people's wound, uncontrollable massive haemorrhage is the main reason for leading to casualties, according to related number
According to showing：In army nearly 50% death be caused by uncontrollable lose blood, in common people's wound, 15-25% be due to
Do not stop blooding in time and leads to death.Therefore, the development of hemostatic material is extremely important for reducing injures and deaths.Mesoporous silicon oxide has
There are larger specific surface area and good biocompatibility, is widely studied as hemostatic material.Simultaneously as its surface carries
A large amount of alcoholic extract hydroxyl group negative electrical charge can activate factor ⅫYou Chengjiechuyinzi after contacting blood, to accelerate blood coagulation waterfall to react, to carry
High anthemorrhagic performance.But the feature of mesoporous silicon oxide tissue adhension effect difference, it is easy to be impregnated with and outside oozing of blood by blood.
In recent years, by mussel byssus protein Ultrastrength adhesive characteristic inspire surface chemistry by scholar extensive concern, at
For the crossing research hot spot in the fields such as bionics, chemistry, materialogy, biology, biomedicine.Meanwhile researchers' channel syndrome
Real catechol（Catechol）Being the key that this kind of material has strong adhesion characteristics group.Laccol is exactly with catechol structure
One analog derivative, it is extracted from raw lacquer, the content in raw lacquer about 80%.Raw lacquer has preferable biocompatibility,
There can be the record used as drug very early with promoting menstruation, hemostasis, cough-relieving etc., China.In order to solve mesoporous silicon oxide
Poor adhesion and oozing of blood problem, we select the laccol with catechol structure to be surface modified it.Laccol is direct at present
Improved silica（Patent publication No.：CN101891205A）Method be by phenolic hydroxyl group in catechol structure in laccol with
The alcoholic extract hydroxyl group of silica surface reacts and laccol is made to be grafted to silica surface, this is but also have tissue adhension characteristic
Catechol group reaction loses adhesion characteristics.We then pass through the radical reaction of laccol side chain unsaturated double-bond so that have
The catechol group of adhesion characteristics is retained, to reach in hemostasis with tissue adhension；The long side chain crosslinking of laccol twines
Form film, have certain hydrophobic property, can anti-Hemostatic Oral Liquid infiltration, and then accelerate hemostasis.
Invention content
The purpose of the present invention is the deficiencies for prior art, it is proposed that one kind is easy to operate, condition is easily controllable, can work
Industry metaplasia is produced, uniform particle sizes, and the laccol with tissue adhension characteristic is modified the synthetic method of mesoporous silicon dioxide micro-sphere and its answered
With.
The present invention is achieved by the following technical solutions：
A. the synthesis of mesoporous silicon dioxide micro-sphere：
By cetyl trimethylammonium bromide（CTAB）It is added to water/ethylene glycol with sodium hydroxide（EG）In solution, 80 DEG C of stirrings
1 h, adds ethyl orthosilicate（TEOS）, continue to stir 6 h, mesoporous silicon dioxide micro-sphere obtained by sol-gel process
Presoma, mesoporous silicon dioxide micro-sphere is obtained after high-temperature calcination；Wherein, the sodium hydroxide and CTAB are with mass parts
Meter, TEOS, EG and water based on parts by volume, sodium hydroxide, CTAB, EG, water, TEOS ratio be（0.01~2）:（0.10~2）:（5
~30）:（70~85）:（0.1~5）.
B. laccol modifies mesoporous silicon dioxide micro-sphere：
By step a）Mesoporous silicon dioxide micro-sphere obtained is scattered in ethyl alcohol, and γ-methacryl is added under the conditions of 70 DEG C
Oxygroup propyl trimethoxy silicane（MPS）, 24 h are stirred, is scattered in ethyl alcohol after being washed with ethyl alcohol, is added under the conditions of 70 DEG C
Azodiisobutyronitrile（AIBN）And laccol, reaction obtain the laccol modification mesoporous silicon oxide containing catechol group afterwards for 24 hours
Microballoon；Wherein, the mesoporous silicon dioxide micro-sphere, AIBN, laccol are in terms of mass parts, and ethyl alcohol is in terms of parts by volume, mesoporous dioxy
SiClx microballoon, AIBN, laccol, ethyl alcohol ratio be（0.1~10）:（0.001~1）:（0.1~30）:（10~100）.
The above-mentioned sodium hydroxide and CTAB of the present invention in terms of mass parts, when mass parts refer to gram or kilogram when, then TEOS, EG and
Water based on parts by volume in parts by volume accordingly refer to mL or L, sodium hydroxide, CTAB, EG, water, TEOS ratio be（0.01~2）:
（0.10~2）:（5~30）:（70~85）:（0.1~5）.
The above-mentioned mesoporous silicon dioxide micro-sphere of the present invention, AIBN, laccol in terms of mass parts, when mass parts refer to gram or kilogram
When, then the parts by volume during ethyl alcohol is in terms of parts by volume accordingly refers to mL or L, mesoporous silicon dioxide micro-sphere, AIBN, laccol, ethyl alcohol ratio
Example be（0.1~10）:（0.001~1）:（0.1~30）:（10~100）.
A kind of laccol containing catechol group such as preceding method synthesis modifies mesoporous silicon dioxide micro-sphere and its is stopping blooding
Purposes in material.
Compared with prior art, the present invention has following advantageous effect：
1, it can be readily synthesized the laccol modification mesoporous silicon dioxide micro-sphere containing catechol group, easy to operate, condition is easy to
Control, can industrialized production, uniform particle sizes.
2, the laccol modification mesoporous silicon dioxide micro-sphere of above method synthesis of the present invention maintains the catechu phenolic group in laccol
Group, can with organize the formation of good adhesiving effect.
3, the above method of the present invention laccol obtained containing catechol group modifies mesoporous silicon dioxide micro-sphere, specific surface area
Up to 448.91 m2/ g can rapidly generate haemostatic effect and be used as hemostat, in vivo with self assembly for amphipathic Janus films
Liver bleeding stopping period is reduced to 22 s.
Description of the drawings
Upon reading the detailed description of non-limiting embodiments with reference to the following drawings, other feature of the invention,
Objects and advantages will become more apparent upon：
Fig. 1 is that the pattern that the laccol obtained containing catechol group of the embodiment of the present invention 1 modifies mesoporous silicon dioxide micro-sphere is saturating
Penetrate electron microscope.
Fig. 2 is that the laccol obtained containing catechol group of the embodiment of the present invention 1 modifies consolidating for mesoporous silicon dioxide micro-sphere
Body13C-NMR schemes.
Fig. 3 is that the laccol modification mesoporous silicon oxide obtained containing catechol group of the embodiment of the present invention 1 is micro- in embodiment 6
The internal liver bleeding stopping period figure of ball.
Specific implementation mode
Embodiment 1
Step 1
0.1 g sodium hydroxides are dissolved in 240 mL glycol/waters（Glycol/water volume ratio is 1:5）In solution, 0.5 g ten is added
Six alkyl trimethyl ammonium bromides（CTAB）With 3 mL ethyl orthosilicates（TEOS）, 6 h, centrifugation, washing are stirred under the conditions of 80 DEG C
And freeze-drying, obtain the presoma of mesoporous silicon dioxide micro-sphere.Again by it under the conditions of 600 DEG C 6 h of high-temperature calcination, be situated between
Hole silicon dioxide microsphere.
Step 2
The mesoporous silicon dioxide micro-sphere for taking 0.5 g above-mentioned is scattered in ethyl alcohol, and 3 mL γ-methacryloxypropyl is added
Trimethoxy silane（MPS）, 70 DEG C of 24 h of reaction, centrifugation, ethyl alcohol washing is for several times.It is scattered in ethyl alcohol again, 0.1 g is added
Azodiisobutyronitrile（AIBN）With 1 g laccols, 70 DEG C of 24 h of reaction are centrifuged, and ethanol/water is washed for several times, freeze-drying, you can must contain
The laccol of catechol group modifies mesoporous silicon dioxide micro-sphere.
Fig. 1 transmission electron microscopes show that the modification mesoporous silicon dioxide micro-sphere of the laccol containing catechol group is in nucleocapsid structure, shell
Thickness is about 17 nm, and internal with abundant duct, and outside is finer and close laccol organic matter layer；Fig. 2 13In C-NMR
140-120 ppm correspond to laccol phenyl ring and pendant double bonds peak show to have synthesized to obtain laccol modification mesoporous silicon oxide it is micro-
Ball.
Embodiment 2
Step 1
0.15 g sodium hydroxides are dissolved in 360 mL glycol/waters（Glycol/water volume ratio is 1:5）In solution, 1.5 g are added
CTAB and 2 mL TEOS, stirs 6 h under the conditions of 80 DEG C, and centrifugation, washing and freeze-drying obtain mesoporous silicon dioxide micro-sphere
Presoma.Again by it under the conditions of 600 DEG C 6 h of high-temperature calcination, obtain mesoporous silicon dioxide micro-sphere.
Step 2
The mesoporous silicon dioxide micro-sphere for taking 1 g above-mentioned is scattered in ethyl alcohol, 2 mL MPS is added, 70 DEG C are reacted 24 h, centrifugation, second
Alcohol washs for several times.It being scattered in ethyl alcohol again, 0.1 g AIBN and 2 g laccols is added, 70 DEG C of 24 h of reaction are centrifuged, ethyl alcohol/
Washed several times with water, freeze-drying, you can the laccol modification mesoporous silicon dioxide micro-sphere of catechol group must be contained.
Embodiment 3
Step 1
0.3 g sodium hydroxides are dissolved in 500 mL glycol/waters（Glycol/water volume ratio is 1:5）In solution, 2.5 g are added
CTAB and 3 mL TEOS, stirs 6 h under the conditions of 80 DEG C, and centrifugation, washing and freeze-drying obtain mesoporous silicon dioxide micro-sphere
Presoma.Again by it under the conditions of 600 DEG C 6 h of high-temperature calcination, obtain mesoporous silicon dioxide micro-sphere.
Step 2
The mesoporous silicon dioxide micro-sphere for taking 1 g above-mentioned is scattered in ethyl alcohol, 5 mL MPS is added, 70 DEG C are reacted 24 h, centrifugation, second
Alcohol washs for several times.It being scattered in ethyl alcohol again, 0.2 g AIBN and 3 g laccols is added, 70 DEG C of 24 h of reaction are centrifuged, ethyl alcohol/
Washed several times with water, freeze-drying, you can the laccol modification mesoporous silicon dioxide micro-sphere of catechol group must be contained.
Embodiment 4
Step 1
0.1 g sodium hydroxides are dissolved in 240 mL glycol/waters（Glycol/water volume ratio is 1:5）In solution, 1.5 g are added
CTAB and 2 mL TEOS, stirs 6 h under the conditions of 70 DEG C, and centrifugation, washing and freeze-drying obtain mesoporous silicon dioxide micro-sphere
Presoma.Again by it under the conditions of 600 DEG C 6 h of high-temperature calcination, obtain mesoporous silicon dioxide micro-sphere.
Step 2
The mesoporous silicon dioxide micro-sphere for taking 3 g above-mentioned is scattered in ethyl alcohol, 3 mL MPS is added, 70 DEG C are reacted 24 h, centrifugation, second
Alcohol washs for several times.It being scattered in ethyl alcohol again, 0.1 g AIBN and 3 g laccols is added, 70 DEG C of 24 h of reaction are centrifuged, ethyl alcohol/
Washed several times with water, freeze-drying, you can the laccol modification mesoporous silicon dioxide micro-sphere of catechol group must be contained.
Embodiment 5
Step 1
0.3 g sodium hydroxides are dissolved in 300 mL glycol/waters（Glycol/water volume ratio is 1:5）In solution, 2.5 g are added
CTAB and 2 mL TEOS, stirs 6 h under the conditions of 80 DEG C, and centrifugation, washing and freeze-drying obtain mesoporous silicon dioxide micro-sphere
Presoma.Again by it under the conditions of 600 DEG C 6 h of high-temperature calcination, obtain mesoporous silicon dioxide micro-sphere.
Step 2
The mesoporous silicon dioxide micro-sphere for taking 2 g above-mentioned is scattered in ethyl alcohol, 1 mL MPS is added, 70 DEG C are reacted 24 h, centrifugation, second
Alcohol washs for several times.It being scattered in ethyl alcohol again, 0.1 g AIBN and 5 g laccols is added, 70 DEG C of 24 h of reaction are centrifuged, ethyl alcohol/
Washed several times with water, freeze-drying, you can the laccol modification mesoporous silicon dioxide micro-sphere of catechol group must be contained.
Embodiment 6
Mesoporous silicon dioxide micro-sphere made from the 10 mg embodiments of the present invention 1 and laccol is taken to modify mesoporous silicon oxide respectively
Microballoon is sprinkling upon mouse liver cut wound mouth（1 cm of length, 0.5 cm of depth）On, start timing, until blood no longer oozes out, stops
Only timing, time at this time are the bleeding stopping period of liver, and each sample, which is repeated 5 times, takes its average value.Liver bleeding stopping period is such as
Shown in Fig. 3.
Fig. 3 statistics indicate that, the present invention synthesize containing catechol group laccol modification mesoporous silicon dioxide micro-sphere liver
Bleeding stopping period only needs 22 s, the bleeding stopping period with mesoporous silicon dioxide micro-sphere（54 s）It compares, bleeding stopping period shortens 59%.It is comprehensive
It closes and considers its biocompatibility and human body degradability, the laccol modification mesoporous silicon dioxide micro-sphere containing catechol group can become
Safe and efficient hemostatic material.
Specific embodiments of the present invention are described above.It is to be appreciated that the invention is not limited in above-mentioned
Particular implementation, those skilled in the art can make various deformations or amendments within the scope of the claims, this not shadow
Ring the substantive content of the present invention.
Claims (3)
1. a kind of synthetic method of the laccol modification mesoporous silicon dioxide micro-sphere containing catechol group, which is characterized in that including such as
Lower step：
A. the synthesis of mesoporous silicon dioxide micro-sphere：
By cetyl trimethylammonium bromide（CTAB）It is added to water/ethylene glycol with sodium hydroxide（EG）In solution, 80 DEG C of stirrings
1 h, adds ethyl orthosilicate（TEOS）, continue to stir 6 h, mesoporous silicon dioxide micro-sphere obtained by sol-gel process
Presoma, mesoporous silicon dioxide micro-sphere is obtained after high-temperature calcination；Wherein, the sodium hydroxide and CTAB are with mass parts
Meter, TEOS, EG and water based on parts by volume, sodium hydroxide, CTAB, EG, water, TEOS ratio be（0.01~2）:（0.10~2）:（5
~30）:（70~85）:（0.1~5）；
B. laccol modifies mesoporous silicon dioxide micro-sphere：
By step a）Mesoporous silicon dioxide micro-sphere obtained is scattered in ethyl alcohol, and γ-methacryl is added under the conditions of 70 DEG C
Oxygroup propyl trimethoxy silicane（MPS）, 24 h are stirred, is scattered in ethyl alcohol after being washed with ethyl alcohol, is added under the conditions of 70 DEG C
Azodiisobutyronitrile（AIBN）And laccol, reaction obtain the modification mesoporous silicon dioxide micro-sphere of the laccol containing catechol group afterwards for 24 hours；
Wherein, the mesoporous silicon dioxide micro-sphere, AIBN, laccol are in terms of mass parts, and by volume, mesoporous silicon oxide is micro- for ethyl alcohol
Ball, AIBN, laccol, ethyl alcohol ratio be（0.1~10:（0.001~1）:（0.1~30）:（10~100）.
2. a kind of laccol containing catechol group of the method as described in claim 1 synthesis modifies mesoporous silicon dioxide micro-sphere.
3. a kind of laccol containing catechol group as claimed in claim 2 modifies mesoporous silicon dioxide micro-sphere in hemostatic material
Purposes.
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Cited By (4)
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|---|---|---|---|---|
| CN109851817A (en) * | 2019-01-29 | 2019-06-07 | 福建师范大学 | The preparation method of freeze proof/heat-resisting adherency hydrogel of laccol co-crosslinking |
| CN110038150A (en) * | 2019-04-12 | 2019-07-23 | 福建师范大学 | The preparation method and modified urushiol hemostatic gauze of the hemostatic gauze of laccol modification |
| CN110794014A (en) * | 2019-11-19 | 2020-02-14 | 山西大学 | Electrochemical immunosensor and preparation method and application thereof |
| CN115246729A (en) * | 2022-08-08 | 2022-10-28 | 温州吉邦科技发展有限公司 | Crack-resistant and seepage-proof dry-mixed plastering mortar and processing technology thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110038150B (en) * | 2019-04-12 | 2021-03-02 | 福建师范大学 | Preparation method of urushiol modified hemostatic gauze and urushiol modified hemostatic gauze |
| CN110794014A (en) * | 2019-11-19 | 2020-02-14 | 山西大学 | Electrochemical immunosensor and preparation method and application thereof |
| CN110794014B (en) * | 2019-11-19 | 2022-03-22 | 山西大学 | Electrochemical immunosensor and preparation method and application thereof |
| CN115246729A (en) * | 2022-08-08 | 2022-10-28 | 温州吉邦科技发展有限公司 | Crack-resistant and seepage-proof dry-mixed plastering mortar and processing technology thereof |
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| CN108721682B (en) | 2021-04-27 |
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