CN113599567A - Cyanoacrylate medical adhesive and preparation method thereof - Google Patents
Cyanoacrylate medical adhesive and preparation method thereof Download PDFInfo
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- CN113599567A CN113599567A CN202110919034.0A CN202110919034A CN113599567A CN 113599567 A CN113599567 A CN 113599567A CN 202110919034 A CN202110919034 A CN 202110919034A CN 113599567 A CN113599567 A CN 113599567A
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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
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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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
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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
- A61L24/0015—Medicaments; Biocides
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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
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
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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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
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Abstract
The invention discloses a cyanoacrylate medical adhesive and a preparation method thereof. Belongs to the field of biomedical materials, and comprises the following components in percentage by mass: 100 parts of alpha-n-butyl cyanoacrylate, 2-8 parts of tributyl citrate, 1-7 parts of hydroxypropyl methacrylate and 1-5 parts of sebacic ester; 0.05-3 parts of a stabilizer; 0.5-2.5 parts of tannic acid; 1-5 parts of thickening agent and 0.001-0.05 part of coloring agent; weighing n-butyl a-cyanoacrylate, tributyl citrate, hydroxypropyl methacrylate, sebacic ester, a stabilizer, tannic acid, a thickener and a colorant according to the mass ratio to prepare the cyanoacrylate tissue adhesive. The cyanoacrylate medical tissue adhesive prepared by the invention takes alpha-cyanoacrylate alkyl ester as a main component; because of its high reactivity, the prepared cyanoacrylate medical adhesive has the advantages of strong bactericidal property, strong adhesive force, fast adhesion speed, etc.
Description
Technical Field
The invention belongs to the field of biomedical materials, and relates to a high-performance tissue adhesive formed by mixing a plurality of materials; in particular to a cyanoacrylate medical adhesive and a preparation method thereof.
Background
Despite the rapid development of medical technology and the creation of novel surgical techniques, traditional mechanical closure techniques for tissue anastomosis and wound repair have not changed. Suturing is always imperfect for both the clinician and the patient, is time consuming, prolongs the procedure time, and increases the risk of infection. In contrast, tissue adhesives are a promising medical material for hemostasis, wound closure, tissue repair and implant fixation. A good tissue adhesive must have good biocompatibility, good adhesive strength and durability, certain elasticity and toughness, no toxicity, and the like, can be used in a normal-temperature, normal-pressure and humid environment, and most of the tissue adhesives made of other raw materials cannot meet the requirements. In order to find a medical adhesive having excellent conditions for preparation, related studies have been conducted.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to provide a cyanoacrylate medical adhesive and a preparation method thereof. It has the advantages of high bonding strength, low cost, abundant raw material sources, convenient use and the like.
The technical scheme is as follows: the invention relates to a cyanoacrylate medical adhesive which comprises the following components in percentage by mass:
further, the weight percentage of each component is as follows:
further, the weight percentage of each component is as follows:
further, the weight percentage of each component is as follows:
further, the stabilizer is one or a combination of more of hydroquinone, p-methoxyphenol, p-toluenesulfonic acid and sulfur dioxide.
Further, the thickening agent is one or more of polybutylcyanoacrylate, polylactic acid and polyethylene glycol.
Further, the colorant is D & C purple dye No. 2.
Further, the preparation method of the cyanoacrylate medical adhesive comprises the following specific preparation steps:
(1) dissolving of basic raw materials:
weighing the components according to the mass ratio;
firstly, equally dividing the n-butyl a-cyanoacrylate into 3 equal parts, taking one part of the n-butyl a-cyanoacrylate, and adding the part into a reactor;
then, sequentially adding weighed tributyl citrate, hydroxypropyl methacrylate, sebacic ester, tannic acid and a thickening agent into the reactor; stirring at room temperature and constant stirring speed until the mixture is dissolved and dispersed, and storing for later use;
(2) dissolution of stabilizers and colorants:
taking one part of the remaining two equal parts of the n-butyl a-cyanoacrylate, adding the one part into another reactor, adding the weighed stabilizer, and stirring at room temperature and constant stirring speed until the stabilizer is dissolved;
adding the weighed colorant, stirring at room temperature and constant stirring speed until the colorant is dissolved, and storing for later use;
(3) mixing of reaction liquid:
dissolving and dispersing the two parts in the steps (1) and (2), storing the mixture for later use, mixing the two parts at room temperature and a constant stirring speed, and continuously stirring until the components are uniform;
(4) preparation of cyanoacrylate medical adhesive:
and (3) after the two mixed reaction liquids in the step (3) are uniformly stirred, adding the remaining part of the n-butyl a-cyanoacrylate into the two uniformly stirred mixed reaction liquids, mixing at room temperature and a constant stirring rate, and continuously stirring for two hours to uniformly mix all the raw materials to finally obtain the tissue adhesive, namely the cyanoacrylate medical adhesive.
Further, the temperature of the room temperature is: 20-25 ℃; the constant stirring rate was 100 r/min.
Wherein, a-n-butyl cyanoacrylate: is a medical adhesive, and the appearance of the medical adhesive is colorless or yellowish transparent liquid. The viscosity (25 ℃) and/mPa.s is more than or equal to 2-5; density 0.985; the content/% > is more than or equal to 99; the characteristics and the application are as follows: (1) the method is characterized in that: can quickly adhere to organism tissues at room temperature, and has strong adhesive force and no toxicity. Has small reaction to tissues, does not form thrombus and can be simply sterilized; (2) the application is as follows: the raw materials are provided for medical adhesive production units; the needle suture operation is replaced, so that no trace is left after the skin incision is anastomosed, and the hemostatic function is realized on the wound; can also be used for the adhesion of internal organs and hemostasis; meanwhile, the modified acrylic acid ester adhesive is used as a blending modification of an alpha-cyanoacrylate adhesive, and has good flexibility; in the using process, the adhesive is applied to the operation bonding position after cleaning the wound, stopping bleeding and sterilizing, and can be solidified and positioned at the body temperature for about 10 s.
Tributyl citrate: the chemical name of the 3-hydroxy-3-carboxyl glutaric acid tributyl ester is an ester compound, and the ester compound is colorless transparent high-boiling-point liquid, slightly soluble in water and mutually soluble with most organic solvents; the industrial product is prepared by reacting citric acid with n-butyl alcohol, can be directly used as a plasticizer, and can be further processed into a plasticizer acetyl tributyl citrate with excellent performance; the product has low toxicity, can be regarded as a nontoxic plasticizer, is commonly called an environment-friendly plasticizer, and can replace phthalate plasticizers with limited application range.
Hydroxypropyl methacrylate: is a chemical compound of formula C7H12O 3; a colorless liquid; boiling point 96 deg.C (1.33kPa), 57 deg.C (66.7Pa), relative density 1.066(25/16 deg.C), refractive index 1.4470, flash point 96 deg.C; dissolving in common organic solvent, and dissolving in water; the product is copolymerized with other acrylic monomers to prepare acrylic resin containing active hydroxyl; preparing a bi-component coating with melamine formaldehyde resin, diisocyanate, epoxy resin and the like; the product can also be used as adhesive for synthetic textile, and additive for cleaning lubricant; the reactive diluent and the crosslinking agent used in a radiation curing system can also be used as a resin crosslinking agent, a plastic and rubber modifier; acrylic resin, acrylic paint, adhesive for textiles and additive for decontamination lubricating oil; can be used as modifier for producing thermosetting coating, adhesive, fiber treating agent and synthetic resin copolymer, and also can be used as one of main crosslinking functional group monomers used for acrylic resin.
Sebacic acid ester: di-n-octyl sebacate with molecular formula C26H50O4Is an ester organic matter which is mainly used as a low-temperature plasticizer; is a typical cold-resistant plasticizer, and is suitable for polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polymethyl methacrylate, cellulose nitrate, ethyl cellulose, synthetic rubber and the like; the cold-resistant wire and cable composite material has high plasticizing efficiency and low volatility, has excellent cold resistance, better heat resistance, light resistance and electrical insulation, has good lubricity during heating, ensures that the product has good appearance and hand feeling, and is particularly suitable for manufacturing cold-resistant wire and cable materials, artificial leather, films, adhesives and the like; however, the product has high mobility, is easy to extract hydrocarbons, has low ideal water resistance, and is often used together with phthalate.
A stabilizer: chemicals that increase the stability of solutions, colloids, solids, and mixtures are called stabilizers; it can slow down reaction, keep chemical balance, reduce surface tension, and prevent light, thermal decomposition or oxidative decomposition; the generalized chemical stabilizer has very wide sources, and can flexibly use any chemical to achieve the aim of stabilizing the product quality according to the design purpose of a formula designer.
Tannic acid: is an organic substance with a chemical formula of C76H52O46，Is a tannin derived from Galla chinensis; is yellow or light brown light amorphous powder or flake; no odor, slight special odor, and extremely astringent taste; soluble in water and ethanol, easily soluble in glycerol, and hardly soluble in diethyl ether, chloroform or benzene; the water solution and the ferric salt solution change into blue-black when meeting, and the color change can be delayed by adding sodium sulfite; in industry, tannic acid is used in great quantities for tanning and making blue inks; tannins are capable of coagulating proteins. The chemical treatment of pig skin and cow skin with tannic acid can coagulate the soluble protein in the raw skin; thus, the raw hide which is originally stink and rotten after being placed for a few days becomes beautiful, clean, flexible and durable leather; this process of tanning is called leather tanning.
Thickening agent: also called gelling agent, is a substance capable of increasing the viscosity of latex and liquid, and is also called paste when used in food; the thickening agent can improve the viscosity of the system, so that the system is kept in a uniform and stable suspension state or an emulsion state, or forms gel; most thickeners combine an emulsifying action. Can be divided into two main categories of natural and synthetic; the natural products are mostly prepared from plants and seaweed containing polysaccharide viscous substances, such as starch, acacia, pectin, agar, gelatin, seaweed gel, carrageenan, dextrin, etc., and general gelatin, soluble starch, polysaccharide derivatives, etc. can be used in cosmetics; the synthetic product includes carboxymethyl cellulose, propylene glycol alginate, methyl cellulose, sodium starch phosphate, sodium carboxymethyl cellulose, sodium alginate, casein, sodium polyacrylate, polyoxyethylene, and polyvinylpyrrolidone.
Colorant: also called food coloring, is a substance that is used for coloring food, and endows the food with color and improves the color of the food; at present, more than 60 food coloring agents are commonly used in the world, 46 food coloring agents are allowed to be used in China, and the food coloring agents are divided into food synthetic coloring agents and food natural coloring agents according to the sources and the properties of the food synthetic coloring agents and the food natural coloring agents; with the improvement of people's awareness of the safety of food additives, the development of natural, nutritional and multifunctional natural colorants has become the development direction of colorants.
Has the advantages that: compared with the prior art, the high-performance tissue adhesive is prepared by simple operations of physical mixing, stirring and the like; the cyanoacrylate medical tissue adhesive prepared by the invention takes alpha-cyanoacrylate alkyl ester as a main component; wherein, because the reaction activity of the cyanoacrylate is very high, the prepared cyanoacrylate medical adhesive has the advantages of strong sterilization, strong adhesive force, high bonding speed and the like.
Drawings
FIG. 1 is a flow chart of a preparation method of the present invention;
FIG. 2 is a comparative illustration of an embodiment of the present invention; wherein (a) is a comparison graph of the adhesive strength of the examples and the control group, and (b) is a comparison graph of the curing time of the examples and the control group.
Detailed Description
The invention is further described with reference to the following drawings and specific embodiments; in the following description, numerous specific details are set forth in order to provide a thorough understanding of the present application, but the present application may be practiced in many ways different from those described herein, and similar modifications may be made by those skilled in the art without departing from the spirit of the present application, and the present application is therefore not limited to the specific implementations disclosed below.
The invention relates to a cyanoacrylate medical adhesive which comprises the following components: a-n-butyl cyanoacrylate, tributyl citrate, hydroxypropyl methacrylate, sebacic acid ester, a stabilizer, tannic acid, a thickener, a colorant and the like; specifically, the weight percentage of each component is as follows:
further, the weight percentage of each component is as follows:
further, the weight percentage of each component is as follows:
further, the weight percentage of each component is as follows:
further, the stabilizer is one or a combination of more of hydroquinone, p-methoxy phenol, p-toluenesulfonic acid and sulfur dioxide; preferably, the stabilizer is a combination of p-methoxyphenol and p-toluenesulfonic acid.
Further, the thickening agent is one or more of polybutylcyanoacrylate, polylactic acid and polyethylene glycol; preferably, the thickener is polybutylcyanoacrylate.
Further, the colorant is D & C purple dye No. 2.
Further, the preparation method of the cyanoacrylate medical adhesive comprises the following specific preparation steps:
(1) dissolving of basic raw materials:
weighing the components according to the mass ratio;
firstly, equally dividing the n-butyl a-cyanoacrylate into 3 equal parts, taking one part of the n-butyl a-cyanoacrylate, and adding the part into a reactor;
then, sequentially adding weighed tributyl citrate, hydroxypropyl methacrylate, sebacic ester, tannic acid and a thickening agent into the reactor; stirring at room temperature and constant stirring speed until the mixture is dissolved and dispersed, and storing for later use;
(2) dissolution of stabilizers and colorants:
taking one part of the remaining two equal parts of the n-butyl a-cyanoacrylate, adding the one part into another reactor, adding the weighed stabilizer, and stirring at room temperature and constant stirring speed until the stabilizer is dissolved;
adding the weighed colorant, stirring at room temperature and constant stirring speed until the colorant is dissolved, and storing for later use;
(3) mixing of reaction liquid:
dissolving and dispersing the two parts in the steps (1) and (2), storing the mixture for later use, mixing the two parts at room temperature and a constant stirring speed, and continuously stirring until the components are uniform;
(4) preparation of cyanoacrylate medical adhesive:
and (3) after the two mixed reaction liquids in the step (3) are uniformly stirred, adding the remaining part of the n-butyl a-cyanoacrylate into the two uniformly stirred mixed reaction liquids, mixing at room temperature and a constant stirring rate, and continuously stirring for two hours to uniformly mix all the raw materials to finally obtain the tissue adhesive, namely the cyanoacrylate medical adhesive.
Further, the temperature of the room temperature is: 20-25 ℃; the constant stirring rate was 100 r/min.
After the adhesive is prepared, the adhesive is coated on pigskin to carry out 180-degree tensile test, and the result shows that the prepared tissue adhesive has good adhesive strength.
Example 1
Accurately weighing 100 parts of alpha-n-butyl cyanoacrylate (reference material), 5 parts of tributyl citrate, 1 part of hydroxypropyl methacrylate, 3.6 parts of sebacic ester, 0.3 part of hydroquinone (stabilizer), 0.5 part of tannic acid, 1 part of polybutyl cyanoacrylate (thickener), and 0.005 part of D & C purple dye No. 2 by mass, fully stirring to prepare cyanoacrylate medical adhesive, and performing 180-degree tensile strength test and curing test; the results show an adhesive strength of about 170kpa and a cure time of about 17 seconds.
Example 2
Accurately weighing 100 parts of alpha-n-butyl cyanoacrylate (reference material), 5 parts of tributyl citrate, 7 parts of hydroxypropyl methacrylate, 3.6 parts of sebacic ester, 0.08 part of p-methoxyphenol (stabilizer), 0.05 part of p-toluenesulfonic acid, 1.5 parts of tannic acid, 5 parts of polylactic acid (thickener) and 0.005 part of colorant according to the mass ratio, fully stirring to prepare cyanoacrylate medical adhesive, and performing 180-degree tensile strength test and curing test; the results showed an adhesive strength of 160kpa and a cure time of about 10 seconds.
Example 3
Accurately weighing 100 parts of alpha-n-butyl cyanoacrylate, 5 parts of tributyl citrate, 3 parts of hydroxypropyl methacrylate, 3.6 parts of sebacic ester, 0.08 part of p-methoxyphenol, 0.05 part of p-toluenesulfonic acid, 1.5 parts of tannic acid, 2.5 parts of thickening agent and 0.005 part of coloring agent according to the mass ratio, fully stirring to prepare cyanoacrylate medical adhesive, and performing 180-degree tensile strength experiment and curing test; the results show an adhesive strength of 200kpa and a cure time of about 10 seconds.
Comparative example
A Comptot tissue adhesive (taking n-butyl-cyanoacrylate as a main component and being provided with a small amount of additives) produced by Beijing Comptot medical instruments GmbH is purchased in the market as a reference substance of a control experiment and is subjected to a 180-degree tensile strength experiment and a curing test; the results show an adhesive strength of 150kpa and a cure time of 15 s.
The above description of the embodiments is only intended to facilitate the understanding of the core ideas of the present invention; meanwhile, for a person skilled in the art, according to the idea of the present invention, there may be variations in the specific embodiments and the application scope, and in summary, the content of the present specification should not be construed as a limitation to the present invention.
Claims (9)
1. The cyanoacrylate medical adhesive is characterized by comprising the following components in percentage by mass:
2. the cyanoacrylate medical adhesive according to claim 1, wherein the mass percent of the components is as follows:
3. the cyanoacrylate medical adhesive according to claim 1, wherein the mass percent of the components is as follows:
4. the cyanoacrylate medical adhesive according to claim 1, wherein the mass percent of the components is as follows:
5. the cyanoacrylate medical adhesive according to claim 1, wherein the stabilizer is one or more of hydroquinone, p-methoxyphenol, p-toluenesulfonic acid, and sulfur dioxide.
6. The cyanoacrylate medical adhesive according to claim 1, wherein the thickener is one or more of polybutylcyanoacrylate, polylactic acid, and polyethylene glycol.
7. A cyanoacrylate medical adhesive according to claim 1, wherein said coloring agent is D & C violet dye No. 2.
8. The preparation method of cyanoacrylate medical adhesive according to claims 1-7, which comprises the following steps:
(1) dissolving of basic raw materials:
weighing the components according to the mass ratio;
firstly, equally dividing the n-butyl a-cyanoacrylate into 3 equal parts, taking one part of the n-butyl a-cyanoacrylate, and adding the part into a reactor;
then, sequentially adding weighed tributyl citrate, hydroxypropyl methacrylate, sebacic ester, tannic acid and a thickening agent into the reactor; stirring at room temperature and constant stirring speed until the mixture is dissolved and dispersed, and storing for later use;
(2) dissolution of stabilizers and colorants:
taking one part of the remaining two equal parts of the n-butyl a-cyanoacrylate, adding the one part into another reactor, adding the weighed stabilizer, and stirring at room temperature and constant stirring speed until the stabilizer is dissolved;
adding the weighed colorant, stirring at room temperature and constant stirring speed until the colorant is dissolved, and storing for later use;
(3) mixing of reaction liquid:
dissolving and dispersing the two parts in the steps (1) and (2), storing the mixture for later use, mixing the two parts at room temperature and a constant stirring speed, and continuously stirring until the components are uniform;
(4) preparation of cyanoacrylate medical adhesive:
and (3) after the two mixed reaction liquids in the step (3) are uniformly stirred, adding the remaining part of the n-butyl a-cyanoacrylate into the two uniformly stirred mixed reaction liquids, mixing at room temperature and a constant stirring rate, and continuously stirring for two hours to uniformly mix all the raw materials to finally obtain the tissue adhesive, namely the cyanoacrylate medical adhesive.
9. The method of claim 8, wherein the room temperature is: 20-25 ℃; the constant stirring rate was 100 r/min.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114796591A (en) * | 2022-06-06 | 2022-07-29 | 北京康派特医疗器械有限公司 | Cyanoacrylate medical adhesive and preparation method and application thereof |
| CN115305021A (en) * | 2022-09-29 | 2022-11-08 | 潍坊德高新材料有限公司 | Colored cyanoacrylate adhesive and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103272263A (en) * | 2013-05-22 | 2013-09-04 | 无锡市华明化工有限公司 | Medical adhesive |
| CN104958781A (en) * | 2015-07-29 | 2015-10-07 | 陕西博与再生医学有限公司 | Chemical medical adhesive composition and preparation method thereof |
-
2021
- 2021-08-11 CN CN202110919034.0A patent/CN113599567A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103272263A (en) * | 2013-05-22 | 2013-09-04 | 无锡市华明化工有限公司 | Medical adhesive |
| CN104958781A (en) * | 2015-07-29 | 2015-10-07 | 陕西博与再生医学有限公司 | Chemical medical adhesive composition and preparation method thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114796591A (en) * | 2022-06-06 | 2022-07-29 | 北京康派特医疗器械有限公司 | Cyanoacrylate medical adhesive and preparation method and application thereof |
| CN115305021A (en) * | 2022-09-29 | 2022-11-08 | 潍坊德高新材料有限公司 | Colored cyanoacrylate adhesive and preparation method thereof |
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Application publication date: 20211105 |