CN100371028C - Medical surgical adhesive - Google Patents
Medical surgical adhesive Download PDFInfo
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- CN100371028C CN100371028C CNB021135541A CN02113554A CN100371028C CN 100371028 C CN100371028 C CN 100371028C CN B021135541 A CNB021135541 A CN B021135541A CN 02113554 A CN02113554 A CN 02113554A CN 100371028 C CN100371028 C CN 100371028C
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- cyanoacrylate
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Abstract
The present invention relates to a medical-use surgical adhesive. The present invention is prepared from alpha-cyanoacrylate and biodegradable high molecular material of the poly three-methylene carbonic-acid ester class which are used as main raw materials, namely that the present invention is formed by the mixing of poly three-methylene carbonic-acid ester which is added to monomers of the alpha-cyanoacrylate class; other auxiliary agents, comprising a formaldehyde catching agent, a stabilizing agent, a cross-linking agent, a surface active agent, a coloring agent, etc. can be added according to requirements. Compared with the reported surgical adhesive, the adhesive of the present invention after being used has the advantages of better flexibility, higher bonding strength and quickened degrading speed.
Description
In the surgical operation, handling wound and the modal method of wound surface is to adopt stitching thread tearing or damaged position sutured, assists the healing of wound to reach the healing purpose.But this method has certain limitation, is difficult to use stitching thread as some operative site and fixes; Sewing effect is relevant with the proficiency level of doctor's operation skill again; And operate more time-consumingly, may stay big, tangible spot behind the wound healing, execute in art and the disconnect process that patient all can not feel well etc.Therefore medical circle a kind ofly makes treatment faster, easy seeking for a long time, the sense of discomfort of patient in treatment still less, the treatment of wounds method of better efficacy, to improve quality of medical care, reduce the sufferer misery.
Coming bonding wound with glue is the optimal path that addresses this problem.Medical glue is rapid in nearly more than ten years development, the various adhesive of medical that are used for tissue, sclerous tissues's (tooth and bone) and skin etc., and composition and performance are different, are applicable to different purposes.Wherein developing with the a-cyanoacrylate is that the various soft tissue adhesives of primary raw material are maximum, and has product constantly to come out, and is widely used in clinical each section.With ethyl, the positive butyl ester of α alpha-cyanoacrylate or isobutyl ester, α-Qing Jibingxisuanzhengxinzhi, α-Qing Jibingxisuanwanjizhi etc.In recent years, mainly be (as United States Patent (USP) 5928611 with the secondary monooctyl ester of alpha-cyanoacrylate (2-octyl cyanoactrylate), 5328687 etc.) be the adhesive of medical of raw material, the additive of its architectural feature, use, tissue intersolubility and biological degradability etc. are compared with the binding agent of other feedstock production, improve, particularly the safety non-toxic of adhesive strength and material.But this class glue is appointed and is also had two problems, fail thoroughly to solve always, and the one, its hardness is too big, and pliability is poor, influences result of use, increases patient's sense of discomfort; The 2nd, degradation speed is slow, influences its scope of application.At first problem, document has the method for interpolation plasticizer (as United States Patent (USP) 4364876 etc.), but effect is bad, and plasticizer adds and too much can influence adhesive strength and safety.To the adjusting of degradation speed, literature research is less, does not see the efficient ways appearance.United States Patent (USP) 3527841 has been studied the viscosity of regulating glue with polylactic acid, above-mentioned two problems is not furtherd investigate.
The object of the present invention is to provide a kind of new medical surgical adhesive, this binding agent is compared with the binding agent of having reported, have after the use and have flexibility preferably, degradation speed is also accelerated, and is to be that primary raw material is prepared from by a-cyanoacrylate and PTMC class Biodegradable Polymers.
The object of the present invention is achieved like this: add PTMC and mix in a-cyanoacrylate class monomer, can add other auxiliary agent as required, as formaldehyde catching agent, stabilizing agent, cross-linking agent, surfactant, stain etc.A-cyanoacrylate class monomer mainly is ethyl, the positive butyl ester of α alpha-cyanoacrylate or isobutyl ester, α-Qing Jibingxisuanzhengxinzhi, α-Qing Jibingxisuanwanjizhi etc.The content of PTMC class Biodegradable Polymers in surgery glue is 0-50%, and the best is 0.00001%-20%.PTMC class Biodegradable Polymers mainly be PTMC homopolymer and poly-PTMC with other monomer copolymerization and must copolymer such as polylactic acid-PTMC copolymer, polyglycolic acid-PTMC copolymer, poly-epsilon-caprolactone-PTMC copolymer and polydioxanone (Polydioxanone)-PTMC copolymer etc.The content of PTMC is 0-100% (weight) in these copolymers, and wherein the best is 20-100%.The intrinsic viscosity of Biodegradable Polymers is that (dark type viscometer, chloroform solvent, 25 ℃) scope is at 0.05-5.0dl/g, and wherein the best is 0.1-3, and molecular weight ranges is 1000-1000000, and the best is 40000-300000.Formaldehyde catching agent mainly contains sulfites (sulphite), bisulfites (acid accumulator sulfite), ammonium sulfite salts, amines (amine), amides (amino-compound), nitrites (nitrite), the carbamates (mixture of one or more among carbaminate, alcohols (alcohols), mercaptans (mercaptan), proteins (protein), proteins (protein), ester (fat), the aimides (amine) etc.Stabilizing agent mainly is sulfur dioxide (sulfur dioxide), sulfonic acid (sulfonic acid), lactone (lactone), boron trifluoride (boron trifluoride), hydroquinone (hydroquinone), hydroquinone monomethyl ether (hydroquinone monomethyl ether), catechol (catechol), pyrogallol (pyrogaelol), benyoquinone (benzoquinone), 2-hydroxbenyoquinone (2-hydroxyl benzoquinone), p-methoxy phenyol (p-methoxyphenol), t-butyl catechol (catechol uncle's butyl ether), organic acid (organic acid), bitylated hydroxyanisole (methoxybenzene), butylated hydroxy toluene, t-butyl hydroquinone (hydroquinone uncle butyl ether), alkyl sulfate (sulfonic acid alkane ester), alkyl sulfite (sulfurous acid alkane ester), 3-sulfolene, alkyl sulfone, alkyl sulfide (sulfo-alkane), the mixture of one or more among the mercaptan (mercaptan) etc.Surfactant mainly contains one or more the mixture among Triton X-100, Tween 20, the Tween80 etc.Stabilizing agent mainly contains sulfur dioxide (sulfur dioxide), sulfonic acid (sulfonic acid), lactone (lactone), boron trifluoride (boron trifluoride), hydroquinone (hydroquinone), hydroquinone monomethyl ether (hydroquinone monomethyl ether), catechol (catechol), pyrogallol (pyrogaelol), benyoquinone (benzoquinone), 2-hydroxbenyoquinone (2-hydroxyl benzoquinone), p-methoxy phenyol (p-methoxyphenol), t-butyl catechol (catechol uncle's butyl ether), organic acid (organic acid), bitylated hydroxyanisole (methoxybenzene), butylated hydroxy toluene, t-butyl hydroquinone (hydroquinone uncle butyl ether), alkyl sulfate (sulfonic acid alkane ester), alkyl sulfite (sulfurous acid alkane ester), 3-sulfolene, alkyl sulfone; The mixture of one or more among alkyl sulfide (sulfo-alkane), the mercaptan (mercaptan) etc.Cross-linking agent mainly contains alkyl bis (2-cyanoacrylates) (two (2-alpha-cyanoacrylate) alkane ester), triallyl isocyanurates (cyamelide three alkane esters); The mixture of one or more among alkylenediacrylates (diacrylate alkane diester), alkylene dimethacrylate (dimethacrylate alkane diester), the trimethylol propane triacrylate (three acrylic acid, three methanol propyl ester) etc.
Surgery glue of the present invention need not to add viscosifier and plasticizer, degradable PTMC and copolymer thereof are a kind of noncrystalline amorphous materials, room temperature is rubbery state, with other material compared be soft, this material can be degraded into carbon dioxide and water fully in human body.Its effect in the present invention removes increases the product degradation property, improves outside the product flexibility, and this material also can be used to regulate the viscosity of product.
Embodiments of the invention are as follows:
The intrinsic viscosity of polymer is measured with dark type viscometer, is solvent with the chloroform, 25 ℃ of mensuration.
Molecular weight is measured with chromatograph of gel permeation (GPC).
The mensuration of adhesive strength: get test Corii Sus domestica (thickness 1-1.5mm, length and width are 50 * 10mm) two, drip the end that the described glue of prescription evenly spreads upon a Corii Sus domestica with 1-2, smearing length is 5mm, bonding an end of another piece Corii Sus domestica with the front, position of cementing, with the hands about 20s of pressure a little, after 10 minutes an end of two bonding Corii Sus domesticas is fixed, the other end comes static state to draw 30 minutes with counterweight, and the maximum weight of the counterweight that can bear is adhesive strength.
Embodiment one:
Take by weighing ethyl 90 grams, PTMC 4 grams (intrinsic viscosity 1.2dl/g, molecular weight 280,000), formaldehyde scavenger (NaHSO
3) 5 grams, stabilizing agent 20ppm, surfactant 0.4 gram, cross-linking agent 0.5 gram, pack behind the mix homogeneously product, as surgical adhesive, range estimation better softness, adhesive strength can be born the static pulling force 30 minutes of 2 kilograms of counterweights.
Embodiment two:
Take by weighing α-Qing Jibingxisuanzhengdingzhi 80 grams, PTMC 2 grams (intrinsic viscosity 0.1dl/g, molecular weight 10000), formaldehyde scavenger (NaHSO
3) 15 grams, stabilizing agent 10ppm, surfactant 0.4 gram, cross-linking agent 2.5 grams, pack behind the mix homogeneously product, as surgical adhesive, range estimation better softness, adhesive strength can be born the static pulling force 30 minutes of 4 kilograms of counterweights.
Embodiment three:
Take by weighing α-Qing Jibingxisuanzhengxinzhi 60 grams, PTMC 20 grams (intrinsic viscosity 3.2dl/g, molecular weight 500,000), formaldehyde scavenger (NaHSO
3) 18 grams, stabilizing agent 20ppm, surfactant 0.9 gram, cross-linking agent 1 gram, pack behind the mix homogeneously product, as surgical adhesive, range estimation better softness, adhesive strength can be born the static pulling force 30 minutes of 1 kilogram of counterweight.
Embodiment four:
Take by weighing 2-octyl 2-cyanoacrylate 70 grams, PTMC 0.001 gram (intrinsic viscosity 1dl/g, molecular weight 150,000), formaldehyde scavenger (NaHSO
3) 8 grams, stabilizing agent 20ppm, surfactant 1 gram, cross-linking agent 20 grams, pack behind the mix homogeneously product, as surgical adhesive, range estimation better softness, adhesive strength can be born the static pulling force 30 minutes of 6 kilograms of counterweights.
Embodiment five:
Take by weighing secondary monooctyl ester 60 grams of 2-alpha-cyanoacrylate, positive butyl ester 30 grams of α alpha-cyanoacrylate, polylactic acid-PTMC copolymer 0.5 gram (intrinsic viscosity 0.8dl/g, molecular weight 90,000), PTMC 0.5 gram (intrinsic viscosity 3.2dl/g, molecular weight 500,000), formaldehyde scavenger (NaHSO
3) 9 grams, pack behind the mix homogeneously product, as surgical adhesive, range estimation better softness, adhesive strength can be born the static pulling force 30 minutes of 3 kilograms of counterweights.
Embodiment six:
Take by weighing 2-octyl 2-cyanoacrylate 99.5 grams, polydioxanone (Polydioxanone)-PTMC copolymer 0.5 gram (intrinsic viscosity 1.2dl/g, molecular weight 280,000), pack behind the mix homogeneously product, as surgical adhesive, the range estimation better softness, adhesive strength can be born the static pulling force 30 minutes of 1 kilogram of counterweight.
Embodiment seven:
Take by weighing 2-octyl 2-cyanoacrylate 99.5 grams, polyglycolic acid-PTMC copolymer 0.5 gram (intrinsic viscosity 1.2dl/g, molecular weight 280,000), pack behind the mix homogeneously product, as surgical adhesive, the range estimation better softness, adhesive strength can be born the static pulling force 30 minutes of 2.5 kilograms of counterweights.
Claims (4)
1. medical surgical adhesive is to be that primary raw material is prepared from by a-cyanoacrylate and PTMC class Biodegradable Polymers.Promptly adding PTMC in a-cyanoacrylate class monomer mixes, PTMC content in glue is 20-100%, glue adds other auxiliary agent as required, as formaldehyde catching agent, stabilizing agent, cross-linking agent, surfactant, stain.
2. medical surgical adhesive according to claim 1 is characterized in that a-cyanoacrylate class monomer is that in the secondary monooctyl ester of ethyl, the positive butyl ester of α alpha-cyanoacrylate or isobutyl ester, α-Qing Jibingxisuanzhengxinzhi, alpha-cyanoacrylate, the α-Qing Jibingxisuanwanjizhi etc. any one uses or use two kinds and two or more mixing to use separately.
3. medical surgical adhesive according to claim 1, it is characterized in that PTMC class Biodegradable Polymers be PTMC homopolymer and poly-PTMC with other monomer copolymerization and must copolymer comprise polylactic acid-PTMC copolymer, polyglycolic acid-PTMC copolymer, poly-epsilon-caprolactone-PTMC copolymer and polydioxanone-PTMC copolymer.
4. according to claim 1 or 3 described medical surgical adhesives, it is characterized in that the content of PTMC class Biodegradable Polymers in glue is 20-100%.The intrinsic viscosity scope of Biodegradable Polymers is at 0.05-5.0dl/g, and molecular weight ranges is 1000-1000000.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021135541A CN100371028C (en) | 2002-04-02 | 2002-04-02 | Medical surgical adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021135541A CN100371028C (en) | 2002-04-02 | 2002-04-02 | Medical surgical adhesive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1448187A CN1448187A (en) | 2003-10-15 |
| CN100371028C true CN100371028C (en) | 2008-02-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB021135541A Expired - Lifetime CN100371028C (en) | 2002-04-02 | 2002-04-02 | Medical surgical adhesive |
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| CN (1) | CN100371028C (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7238828B2 (en) * | 2005-03-24 | 2007-07-03 | Ethicon, Inc. | Absorbable α-cyanoacrylate compositions |
| CN101209238B (en) * | 2006-12-27 | 2012-05-09 | 辽宁省计划生育科学研究院 | Biological degradation type long-acting subcutaneous contraception implant containing gestodene and preparation thereof |
| CN102365101A (en) * | 2009-03-27 | 2012-02-29 | 阿克塔马克斯手术器材有限责任公司 | Tissue adhesive and sealant comprising polyglycerol aldehyde |
| CN102925064A (en) * | 2012-10-25 | 2013-02-13 | 无锡市三力胶带厂 | Interventional anti-infective water-based adhesive |
| CN103599559A (en) * | 2013-10-30 | 2014-02-26 | 李小群 | Polylactic acid modified medical operation incision adhesion agent |
| CN104399113B (en) * | 2014-11-25 | 2016-07-13 | 青岛金智高新技术有限公司 | A kind of soft tissue binding agent and preparation method thereof |
| CN108686257B (en) * | 2018-06-21 | 2021-04-27 | 浙江派菲特新材料科技有限公司 | Medical adhesive with high antibacterial performance |
| CN108452369B (en) * | 2018-06-21 | 2021-02-09 | 浙江派菲特新材料科技有限公司 | Preparation method of medical adhesive with high antibacterial performance |
| CN111117500A (en) * | 2019-12-31 | 2020-05-08 | 江苏天时新材料科技有限公司 | Antistatic decontamination automobile protection film |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5328687A (en) * | 1993-03-31 | 1994-07-12 | Tri-Point Medical L.P. | Biocompatible monomer and polymer compositions |
| CN1205644A (en) * | 1995-12-22 | 1999-01-20 | 美国3M公司 | Skin-applicable pressure-sensitive adhesive and method of making the same |
-
2002
- 2002-04-02 CN CNB021135541A patent/CN100371028C/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5328687A (en) * | 1993-03-31 | 1994-07-12 | Tri-Point Medical L.P. | Biocompatible monomer and polymer compositions |
| CN1205644A (en) * | 1995-12-22 | 1999-01-20 | 美国3M公司 | Skin-applicable pressure-sensitive adhesive and method of making the same |
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| Publication number | Publication date |
|---|---|
| CN1448187A (en) | 2003-10-15 |
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