CN1448187A - Medical surgical adhesive - Google Patents
Medical surgical adhesive Download PDFInfo
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- CN1448187A CN1448187A CN 02113554 CN02113554A CN1448187A CN 1448187 A CN1448187 A CN 1448187A CN 02113554 CN02113554 CN 02113554 CN 02113554 A CN02113554 A CN 02113554A CN 1448187 A CN1448187 A CN 1448187A
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- CN
- China
- Prior art keywords
- ptmc
- cyanoacrylate
- copolymer
- medical surgical
- alpha
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003106 tissue adhesive Substances 0.000 title abstract description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000003381 stabilizer Substances 0.000 claims abstract description 9
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical group OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 8
- 239000004094 surface-active agent Substances 0.000 claims abstract description 8
- 239000003894 surgical glue Substances 0.000 claims abstract 5
- -1 isobutyl ester Chemical class 0.000 claims description 18
- 229920001577 copolymer Polymers 0.000 claims description 15
- 229920002988 biodegradable polymer Polymers 0.000 claims description 8
- 239000004621 biodegradable polymer Substances 0.000 claims description 8
- 239000003292 glue Substances 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 229920002463 poly(p-dioxanone) polymer Polymers 0.000 claims description 6
- 239000000622 polydioxanone Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 229920006237 degradable polymer Polymers 0.000 abstract 1
- 230000000593 degrading effect Effects 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000002861 polymer material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 14
- 239000000853 adhesive Substances 0.000 description 13
- 230000001070 adhesive effect Effects 0.000 description 13
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 12
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 12
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 230000003068 static effect Effects 0.000 description 8
- 238000005303 weighing Methods 0.000 description 7
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 5
- 206010052428 Wound Diseases 0.000 description 5
- 208000027418 Wounds and injury Diseases 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002516 radical scavenger Substances 0.000 description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- 241000282894 Sus scrofa domesticus Species 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- CQVWXNBVRLKXPE-UHFFFAOYSA-N 2-octyl cyanoacrylate Chemical compound CCCCCCC(C)OC(=O)C(=C)C#N CQVWXNBVRLKXPE-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- GPLIMIJPIZGPIF-UHFFFAOYSA-N 2-hydroxy-1,4-benzoquinone Chemical compound OC1=CC(=O)C=CC1=O GPLIMIJPIZGPIF-UHFFFAOYSA-N 0.000 description 2
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920001241 Cyamelide Polymers 0.000 description 1
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical class [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- OURRXQUGYQRVML-AREMUKBSSA-N [4-[(2s)-3-amino-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl]phenyl]methyl 2,4-dimethylbenzoate Chemical compound CC1=CC(C)=CC=C1C(=O)OCC1=CC=C([C@@H](CN)C(=O)NC=2C=C3C=CN=CC3=CC=2)C=C1 OURRXQUGYQRVML-AREMUKBSSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- SMEDVXJKKOXLCP-UHFFFAOYSA-N cyamelide Chemical compound N=C1OC(=N)OC(=N)O1 SMEDVXJKKOXLCP-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 229940075469 tissue adhesives Drugs 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Abstract
The medical surgical adhesive is prepared by mixing polytrimethene carbonate with alpha-cyanoacrylate monomer as biologically degradable polymer material. If necessary, other assistants, such as formaldehyde trap, stabilizer, cross-linking agent, surfactant and dyeing agent, may be also added. Compared with available medical surgical adhesives, the present invention has relatively high flexibility, relatively high adhering strength and high 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 (enclosing patent 4364876 etc. as U.S.A), but effect is bad, and the plasticizer interpolation 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 hydroxyani sole (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, Tween20, 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 one kinds of medical surgical adhesives are to be that primary raw material is prepared from by a-cyanoacrylate and PTMC class Biodegradable Polymers.Promptly in a-cyanoacrylate class monomer, add PTMC and mix, can add other auxiliary agent as required, as formaldehyde catching agent, stabilizing agent, cross-linking agent, surfactant, stain etc.
2 medical surgical adhesives according to claim 1 is characterized in that a-cyanoacrylate class monomer mainly 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 secondary monooctyl ester of 2-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 adhesives according to claim 1, it is characterized in that 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.
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 0-100% (weight), 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 0.1-3dl/g, and molecular weight ranges is 1000-1000000, and the best is 40000-300000.
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 true CN1448187A (en) | 2003-10-15 |
| CN100371028C CN100371028C (en) | 2008-02-27 |
Family
ID=28680581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB021135541A Expired - Lifetime CN100371028C (en) | 2002-04-02 | 2002-04-02 | Medical surgical adhesive |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100371028C (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 hypodermal contraception implant containing gestodene and preparation thereof |
| CN101180085B (en) * | 2005-03-24 | 2012-09-05 | 伊西康公司 | Absorbable alpha-cyanoacrylate compositions |
| 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 |
| CN104399113A (en) * | 2014-11-25 | 2015-03-11 | 苏州市贝克生物科技有限公司 | Adhesive for soft tissues and preparation method of adhesive |
| CN108452369A (en) * | 2018-06-21 | 2018-08-28 | 浙江派菲特新材料科技有限公司 | A kind of preparation method of high anti-microbial property adhesive of medical |
| CN108686257A (en) * | 2018-06-21 | 2018-10-23 | 浙江派菲特新材料科技有限公司 | A kind of high anti-microbial property adhesive of medical |
| 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 |
Family Cites Families (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 |
| US5876855A (en) * | 1995-12-22 | 1999-03-02 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive suitable for skin and method of preparing |
-
2002
- 2002-04-02 CN CNB021135541A patent/CN100371028C/en not_active Expired - Lifetime
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| CN101180085B (en) * | 2005-03-24 | 2012-09-05 | 伊西康公司 | Absorbable alpha-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 hypodermal 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 |
| CN104399113A (en) * | 2014-11-25 | 2015-03-11 | 苏州市贝克生物科技有限公司 | Adhesive for soft tissues and preparation method of adhesive |
| CN108452369A (en) * | 2018-06-21 | 2018-08-28 | 浙江派菲特新材料科技有限公司 | A kind of preparation method of high anti-microbial property adhesive of medical |
| CN108686257A (en) * | 2018-06-21 | 2018-10-23 | 浙江派菲特新材料科技有限公司 | A kind of high anti-microbial property adhesive of medical |
| 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 |
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| CN100371028C (en) | 2008-02-27 |
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