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Biodegradable medical adhesive, and preparation method and purpose thereof

An adhesive, cyanoacrylic acid technology, applied in nitrile copolymer adhesives, ester copolymer adhesives, non-polymer organic compound adhesives, etc., can solve problems such as difficult degradation and absorption

Active Publication Date: 2013-05-08
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the modification of side chains in these works has accelerated the degradation of side chain esters, in fact, this type of degradation is the degradation of polymer side chains, and the linear carbon-carbon main chain of polymers is still difficult to degrade and absorb.

Method used

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  • Biodegradable medical adhesive, and preparation method and purpose thereof
  • Biodegradable medical adhesive, and preparation method and purpose thereof
  • Biodegradable medical adhesive, and preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0096] Preparation Example 1: Synthesis of Bisα-cyanoacrylate PLA-PEG-PLA

[0097] The synthesis of bisα-cyanoacrylate compounds is basically similar, and the references (US3975422, 4012402, 4041061) are synthesized in a similar way. In this example, bisα-cyanoacrylate PLA-PEG-PLA is taken as an example for description.

[0098] The structure of bisα-cyanoacrylate PLA-PEG-PLA is as follows:

[0099]

[0100] Its unique intermediate segment PLA-PEG-PLA block copolymer (1-1) synthesis method is as follows:

[0101]

[0102] 10.13g PEG1000 (10.13mmol) and 10.37g lactide (72mmol) were added to the reaction flask, heated at 70°C to melt the solid, evacuated and filled with argon, repeated the operation three times, removed the water in the reaction solution, added 20mg Stannous octoate solution, continue to vacuum until there are no bubbles in the reaction solution, heat the reaction solution to 180 ° C, react for 6 hours, stop heating, cool to room temperature, add 8 ml of...

preparation example 2

[0115] Preparation Example 2: Examples of other bis-α-cyanoacrylates

[0116] Using a method similar to that in Preparation Example 1 and selecting different intermediate fragments, the following compounds can be synthesized

[0117] Diethylene glycol bis-α-cyanoacrylate

[0118] 1 HNMR (CDCl 3 , δppm): δ7.07(s, 2H), δ6.67(s, 2H), δ4.44(t, 4H), δ3.82(t, 4H) light yellow oily liquid

[0119] Triethylene glycol bis-α-cyanoacrylate

[0120] 1 HNMR (CDCl 3 , δppm): δ7.08(s, 2H), δ6.65(s, 2H), δ4.44(t, 4H), δ3.80(t, 4H), δ3.66-3.70(m, 8H) light yellow oily liquid

[0121] Bisα-Cyanoacrylate PEG600 Ester

[0122] 1 HNMR (CDCl 3 , δppm): δ7.08(s, 2H), δ6.66(s, 2H), δ4.43(m, 4H), δ3.68(m, 54H)

[0123] Bisα-Cyanoacrylate PEG1000 Ester

[0124] 1 HNMR (CDCl 3 , δppm): δ7.08(s, 2H), δ6.71(s, 2H), δ4.42-4.44(m, 4H), δ3.57-3.80(m, 90H) light yellow oily liquid

[0125] Bisα-Cyanoacrylate PEG2000 Ester

[0126] 1 HNMR (CDCl 3 , δppm): δ7.09(s, 2H), δ6.66(s, 2H), δ4.42-4.4...

preparation example 3

[0138] Preparation Example 3: Example of Mono-α-cyanoacrylate

[0139] This kind of compound is carried out with reference to literature reports (Li Jingfeng, Sun Xiping. The preparation technology and application of α-cyanoacrylate adhesive. Colloid and polymer. 1999, 17(3): 33-34; CN 87103468A) general method, namely with Under the condition of basic catalyst, cyanoacetate is polymerized with aqueous formaldehyde solution to form a low molecular weight prepolymer, and then depolymerized and purified at high temperature under reduced pressure. Taking n-butyl cyanoacrylate as an example, its chemical reaction formula is as follows:

[0140]

[0141] Mono-α-cyanoacrylate is obtained.

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Abstract

The invention relates to a novel medical adhesive which can be subjected to crosslinking copolymerization and which has good biodegradability. A polymer substrate of the adhesive comprises both single alpha-cyanoacrylate and double alpha-diol cyanoacrylate monomer molecules. Olefinic bonds in single alpha-cyanoacrylate structure can be subjected to polymerization under a trace-amount anionic condition. The double alpha-diol cyanoacrylate in the polymer substrate can serve as a crosslinking agent, such that crosslinking copolymerization of the system can be carried out. Chain growth occurs with a three-dimensional multi-point polymerization manner. A gelling speed is fast, and linear polymerization degree of double-bond polymerization is low. A meshed main chain of the solid 3D-body high polymer obtained by polymerization has degradation sites. Degradation product path is clear, and the degradation product can be absorbed. The medical adhesive can be used in wound bonding, bleeding stopping at massive trauma, visceral and soft tissue wound closure, and the like. In addition, the medical adhesive has a potential purpose to be developed into a tissue engineering material.

Description

technical field [0001] The invention relates to a medical adhesive, in particular to a biodegradable medical adhesive. The medical adhesive is biodegradable, the degradation product is non-toxic and absorbable, and can be used for skin wound adhesion, tissue adhesion, wound hemostasis, and the like. Background technique [0002] The emergence of medical adhesives (medical glue) has changed the concept of traditional medicine only relying on needles and threads to suture wounds. By means of bonding, needles and threads can be replaced or assisted. It has the advantages of simple operation and no secondary damage to the wound. It also has the advantage that it can be applied or assisted in the soft tissues, internal organs, bones and other parts that are difficult to be sutured by surgical needles and threads such as the liver and pancreas. In addition, for large-scale superficial bleeding, abrasions, burns, battlefield injuries, field injuries, intestinal leakage, etc., this...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61L24/06A61L27/16A61L27/50A61L27/58C08F290/06C08F220/34C08F222/22
CPCC09J4/00C08F222/32C09J135/04C08L35/04A61L24/043A61L24/06C09J133/14C09J133/20C08L2312/00A61L24/0042C08F222/324C08F222/326C08F222/328C08F222/322C08F220/286A61L24/0015C08F283/02
Inventor 刘克良徐亮张青松蔡大振孟庆斌
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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