CN116870237A - Photoinitiated tissue adhesives and methods of use thereof - Google Patents
Photoinitiated tissue adhesives and methods of use thereof Download PDFInfo
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- CN116870237A CN116870237A CN202310901039.XA CN202310901039A CN116870237A CN 116870237 A CN116870237 A CN 116870237A CN 202310901039 A CN202310901039 A CN 202310901039A CN 116870237 A CN116870237 A CN 116870237A
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- Prior art keywords
- photoinitiated
- cyanoacrylate
- tissue adhesive
- acrylated
- salt
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- 239000003106 tissue adhesive Substances 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 9
- 229940075469 tissue adhesives Drugs 0.000 title description 2
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229920001651 Cyanoacrylate Polymers 0.000 claims abstract description 13
- 239000002861 polymer material Substances 0.000 claims abstract description 12
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 12
- 229920001477 hydrophilic polymer Polymers 0.000 claims abstract description 9
- 239000003112 inhibitor Substances 0.000 claims abstract description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 17
- -1 alpha-cyano isooctyl acrylate Chemical compound 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000000853 adhesive Substances 0.000 claims description 10
- 230000001070 adhesive effect Effects 0.000 claims description 10
- 244000028419 Styrax benzoin Species 0.000 claims description 8
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 8
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 8
- 229960002130 benzoin Drugs 0.000 claims description 8
- 235000019382 gum benzoic Nutrition 0.000 claims description 8
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 5
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 claims description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- 239000012952 cationic photoinitiator Substances 0.000 claims description 4
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 4
- 239000012949 free radical photoinitiator Substances 0.000 claims description 4
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 claims description 3
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 claims description 3
- PKHKPLVXRYPWPO-UHFFFAOYSA-N 1-bromo-3-[(3-bromophenyl)-phenylphosphoryl]benzene Chemical compound BrC1=CC=CC(P(=O)(C=2C=CC=CC=2)C=2C=C(Br)C=CC=2)=C1 PKHKPLVXRYPWPO-UHFFFAOYSA-N 0.000 claims description 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims description 3
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 claims description 3
- 229920001661 Chitosan Polymers 0.000 claims description 3
- 108010022355 Fibroins Proteins 0.000 claims description 3
- 108010010803 Gelatin Proteins 0.000 claims description 3
- 229920002385 Sodium hyaluronate Polymers 0.000 claims description 3
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical compound CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 claims description 3
- 229940053009 ethyl cyanoacrylate Drugs 0.000 claims description 3
- 229920000159 gelatin Polymers 0.000 claims description 3
- 239000008273 gelatin Substances 0.000 claims description 3
- 235000019322 gelatine Nutrition 0.000 claims description 3
- 235000011852 gelatine desserts Nutrition 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 235000010413 sodium alginate Nutrition 0.000 claims description 3
- 229940005550 sodium alginate Drugs 0.000 claims description 3
- 239000000661 sodium alginate Substances 0.000 claims description 3
- 229940010747 sodium hyaluronate Drugs 0.000 claims description 3
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 claims description 3
- OLPZCIDHOZATMA-UHFFFAOYSA-N 2,2-dioxooxathiiran-3-one Chemical compound O=C1OS1(=O)=O OLPZCIDHOZATMA-UHFFFAOYSA-N 0.000 claims description 2
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 2
- KGGBUGLHJUGXEF-UHFFFAOYSA-N [6-hydroxy-4-(2-hydroxyethoxy)-6-methylcyclohexa-2,4-dien-1-yl]-phenylmethanone Chemical compound OC1(C(C(=O)C2=CC=CC=C2)C=CC(=C1)OCCO)C KGGBUGLHJUGXEF-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 125000005520 diaryliodonium group Chemical group 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 claims description 2
- 229910001392 phosphorus oxide Inorganic materials 0.000 claims 2
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 claims 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 claims 1
- RKCKOWJWQLITLM-UHFFFAOYSA-N P(O)(O)=O.C1(=CC=CC=C1)C=1C(=C(C(=O)[Li])C(=CC1C)C)C Chemical compound P(O)(O)=O.C1(=CC=CC=C1)C=1C(=C(C(=O)[Li])C(=CC1C)C)C RKCKOWJWQLITLM-UHFFFAOYSA-N 0.000 claims 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 208000032544 Cicatrix Diseases 0.000 abstract description 2
- 230000035876 healing Effects 0.000 abstract description 2
- 231100000241 scar Toxicity 0.000 abstract description 2
- 230000037387 scars Effects 0.000 abstract description 2
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 9
- 238000001723 curing Methods 0.000 description 6
- 239000004830 Super Glue Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 206010052428 Wound Diseases 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000003833 cell viability Effects 0.000 description 2
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- HFQQYIUTYJVYFZ-UHFFFAOYSA-N 4-methylpentyl 2-cyanoprop-2-enoate Chemical compound CC(C)CCCOC(=O)C(=C)C#N HFQQYIUTYJVYFZ-UHFFFAOYSA-N 0.000 description 1
- FXDAXLSJARZDBW-UHFFFAOYSA-N 6-methylheptyl 2-cyanoprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(=C)C#N FXDAXLSJARZDBW-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002439 hemostatic effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- QRWOVIRDHQJFDB-UHFFFAOYSA-N isobutyl cyanoacrylate Chemical compound CC(C)COC(=O)C(=C)C#N QRWOVIRDHQJFDB-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- RPQUGMLCZLGZTG-UHFFFAOYSA-N octyl cyanoacrylate Chemical compound CCCCCCCCOC(=O)C(=C)C#N RPQUGMLCZLGZTG-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- A61L24/08—Polysaccharides
-
- 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
- A61L24/10—Polypeptides; Proteins
-
- 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
- A61L24/10—Polypeptides; Proteins
- A61L24/104—Gelatin
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Materials For Medical Uses (AREA)
Abstract
The invention discloses a photoinitiated tissue adhesive and a use method thereof, belonging to the field of polymers. The tissue adhesive consists of cyanoacrylate, acrylated hydrophilic polymer material, photoinitiator and polymerization inhibitor in the weight portions of 50-80 wt%, 20-50 wt%, 0.1-0.3 wt% and 0.1-0.3 wt%. The introduction of the water-based polymer material group can also absorb part of wound seepage, provide a certain wet healing environment and reduce the generation of scars.
Description
Technical Field
The invention belongs to the field of polymers, and particularly relates to a photoinitiated tissue adhesive and a use method thereof.
Background
In 1958, eastman Kodark, USA successfully developed and brought to market the first alpha-cyanoacrylate adhesive Eastman 910. Subsequently, α -cyanoacrylate adhesives are favored by the medical community for quick adhesion. In 1962, china began to devote to research and produce cyanoacrylate adhesives and 508 and other products were developed by the western An chemical institute in the 70 th century. The third army medical university synthesizes the alpha-cyano acrylic acid-1, 2-isopropylidene glyceride, and clinical observation proves that the hemostatic effect is good. With intensive research, short-chain cyanoacrylates have been found to be cytotoxic, while long-chain cyanoacrylates have relatively low biological toxicity. With the perfection of the process, the purity of the cyanoacrylate monomer is higher and higher, and the toxicity is greatly reduced, so that various derivatized cyanoacrylate adhesives are gradually produced. Such adhesives currently used in the medical field mainly include methyl cyanoacrylate, ethyl cyanoacrylate, isobutyl cyanoacrylate, isohexyl cyanoacrylate, octyl cyanoacrylate, and the like.
However, these adhesives also have problems such as (1) spontaneous heat release when cyanoacrylate polymers are formed, potentially thermally affecting biological tissues and cells; (2) Cyanoacrylate unreacted monomers are somewhat cytotoxic and can cause inflammatory reactions and even tissue necrosis in some patients following cyanoacrylate adhesives.
Disclosure of Invention
The invention aims at the technical problems and provides a photoinitiated tissue adhesive and a use method thereof.
9. A photoinitiated tissue adhesive consists of 50-80 parts by weight, 20-50 parts by weight, 0.1-0.3 part by weight and 0.1-0.3 part by weight of cyanoacrylate, an acrylated hydrophilic polymer material, a photoinitiator and a polymerization inhibitor.
In the technical scheme of the invention, the cyanoacrylate is one or more of methyl cyanoacrylate (CAS: 137-05-3), ethyl cyanoacrylate (CAS: 7085-85-0), butyl-2-cyanoacrylate (CAS: 6606-65-1) and alpha-isooctyl cyanoacrylate (CAS: 184765-00-2).
The technical scheme of the invention is as follows: the acrylated hydrophilic polymer material is one or more of acrylated gelatin (gelatin CAS: 9000-70-8), acrylated sodium hyaluronate (sodium hyaluronate CAS: 9067-32-7), acrylated silk fibroin (silk fibroin CAS: 96690-41-4), acrylated chitosan (chitosan CAS: 9012-76-4) and acrylated sodium alginate (sodium alginate CAS: 9005-38-3).
In the technical scheme of the invention, the photoinitiator is a free radical photoinitiator or a cationic photoinitiator.
In some specific embodiments, the free radical photoinitiator comprises benzoin and derivatives (benzoin (579-44-2), benzoin dimethyl ether (24650-42-8), benzoin diethyl ether (574-09-4), benzoin isopropyl ether (6652-28-4)), benzil (diphenylethanone (451-40-1), α -dimethoxy- α -phenylacetophenone (24650-42-8), 2-hydroxy-4- (2-hydroxyethoxy) -2-methylbenzophenone (106797-53-9)), alkylphenones (α, α -diethoxyacetophenone (6175-45-7)), acylphosphorus oxides (aroylphosphine oxides, bis (3-bromophenyl) phenylphosphine oxide (1163698-32-5), phenyl-2, 4, 6-trimethylbenzoylphosphonic lithium (85073-19-4)), benzophenone (119-61-9), 2, 4-dihydroxybenzophenone (606-12-2), michler's ketone (90-94-8), xanthone (5475-95-84-isopropyl xanthone), or (5484-84-isopropyl xanthone).
In the technical scheme of the invention, the cationic photoinitiator comprises one or more of diazonium salt, diaryl iodonium salt, triarylsulfonium salt, alkyl sulfonium salt, iron arene salt, sulfonyloxy ketone and triarylsiloxane ether.
In the technical scheme of the invention, the polymerization inhibitor is one or more of hydroquinone (123-31-9), p-benzoquinone (106-51-4), p-toluenesulfonic acid (104-15-4), organic copper salt, quaternary ammonium salt and sulfur dioxide (7446-09-5).
In the technical scheme of the invention, the application method of the photoinitiated adhesive comprises the steps of uniformly coating the adhesive on a wound surface, enabling 10-20S cyanoacrylate to undergo self-curing reaction, and then irradiating the adhesive part with ultraviolet light or blue light for 5-10S, so that polymerization crosslinking reaction can be further initiated.
Synergistic reaction advantages:
(1) In the instant polymerization of α -cyanoacrylate, the polymerization heat can be appropriately reduced due to the presence of the acrylated hydrophilic polymer material (acting as a filler).
(2) In the second step of photocuring reaction, the photoinitiator can initiate the crosslinking reaction of unreacted alpha-cyanoacrylate in addition to the crosslinking reaction of the acrylic acylated hydrophilic polymer material, so that the cytotoxicity reaction of the alpha-cyanoacrylate monomer is reduced.
(3) The simple alpha-cyanoacrylate curing reaction is compact and hard in reactant, and the flexibility of the reactant is improved after the cross-linked network structure is introduced.
(4) The introduction of the cross-linked network structure improves the air permeability of the tissue adhesive and can promote wound healing.
(5) The introduction of the water-based polymer material group can also absorb part of wound seepage, provide a certain wet healing environment and reduce the generation of scars.
Synergistic reaction mechanism of alpha-cyanoacrylate and acrylated hydrophilic polymer material
When the mixture is smeared on a tissue wound surface, alpha-cyanoacrylate generates instant polymerization reaction under the catalysis of anions in wound blood or tissue fluid (moisture and protein), and the reaction time is generally 10-20S. And then irradiating ultraviolet or blue light with different wavelengths (different photoinitiators correspond to the light with different wavelengths) on the reactant subjected to primary curing to trigger the cross-linking reaction of the acrylic acylated hydrophilic high polymer material and the unreacted alpha-cyanoacrylate in the reactant subjected to primary curing, so as to form a cross-linked network structure in the reactant subjected to primary curing.
Drawings
FIG. 1 is a schematic diagram of a synergistic reaction product.
Fig. 2 is a scanning electron microscope image of the target product of example 1.
Description of the preferred embodiments
The invention is further illustrated below with reference to examples, but the scope of the invention is not limited thereto:
TABLE 1 examples 1-3 Components and amounts thereof
Examples 1 to 3:
under the protection of nitrogen, adding the modified acrylic hydrophilic polymer material into cyanoacrylate solution, magnetically stirring until the mixture is uniform, stirring and dripping photoinitiator and polymerization inhibitor into the solution, and stirring until the mixture is uniform.
Pushing the solution into a designated container by adopting a filter membrane of 0.22 mu m under a sterile environment, and sealing for later use. The prepared adhesive is smeared on the surface of a smooth polytetrafluoroethylene plate, the smearing size is 30 multiplied by 10mm, and the thickness is 0.1mm. Moisture curing was performed for 15S (heat of polymerization was measured) and then ultraviolet light having a wavelength ranging from 250 to 260nm was irradiated for 5S.
And (3) performance detection:
the samples were prepared and tested for mechanical properties and cytotoxicity (example 1).
| Performance index | Test group | Commercial products |
| Maximum curing temperature | 57.4℃ | 68.9℃ |
| Tensile strength | 0.93kg/cm 2 | 0.96kg/cm 2 |
| Adhesive strength | 19.5kPa | 17.8kPa |
| Elongation at break | 186％ | 55％ |
| Air permeability | 2350g/cm 2 /d | 974g/cm 2 /d |
| Water absorption capacity | 9.42％ | 0.27％ |
The above preparation (example 1) was subjected to leaching at 0.2g/ml for 24h at a leaching temperature of 72 ℃.
The materials were tested for cytotoxicity and compared to commercial products.
| Group of | Cell viability of test group% | Commercial product cell viability% |
| 100% sample leaching solution | 74.5 | 25.4 |
| 75% sample leach liquor | 81.6 | 45.7 |
| 50% sample leach liquor | 87.3 | 64.3 |
| 25% sample leach liquor | 96.0 | 78.2 |
Claims (8)
1. A photoinitiated tissue adhesive, characterized by: the tissue adhesive consists of cyanoacrylate, acrylated hydrophilic polymer material, photoinitiator and polymerization inhibitor in the weight portions of 50-80 wt%, 20-50 wt%, 0.1-0.3 wt% and 0.1-0.3 wt%.
2. The photoinitiated tissue adhesive according to claim 1, wherein: the cyanoacrylate is one or more of methyl cyanoacrylate, ethyl cyanoacrylate, butyl-2-cyanoacrylate and alpha-cyano isooctyl acrylate.
3. The photoinitiated tissue adhesive according to claim 1, wherein: the acrylated hydrophilic polymer material is one or more of acrylated gelatin, sodium hyaluronate, acrylated silk fibroin, acrylated chitosan and acrylated sodium alginate.
4. The photoinitiated tissue adhesive according to claim 1, wherein: the photoinitiator is a free radical photoinitiator or a cationic photoinitiator.
5. The photoinitiated tissue adhesive according to claim 1, wherein: the free radical photoinitiator is selected from one or more of benzoin and derivatives, benzil, alkyl benzene ketone, acyl phosphorus oxide, diphenyl ketone and thioxanthone:
benzoin and derivatives are benzoin dimethyl ether, benzoin diethyl ether or benzoin isopropyl ether;
benzil is diphenylethanone, alpha-dimethoxy-alpha-phenylacetophenone or 2-hydroxy-4- (2-hydroxyethoxy) -2-methylbenzophenone);
alkylbenzene ketones: α, α -diethoxyacetophenone;
acyl phosphorus oxide: aroylphosphine oxide, bis (3-bromophenyl) phenylphosphine oxide, or phenyl-2, 4, 6-trimethylbenzoyl lithium phosphonate;
benzophenone type: benzophenone, 2, 4-dihydroxybenzophenone or Michler's ketone;
thioxanthones: 2-isopropylthioxanthone or isopropylthioxanthone.
6. The photoinitiated tissue adhesive according to claim 1, wherein: the cationic photoinitiator comprises one or more of diazonium salt, diaryl iodonium salt, triarylsulfonium salt, alkyl sulfonium salt, iron arene salt, sulfonyloxy ketone and triarylsiloxane ether.
7. The photoinitiated tissue adhesive according to claim 1, wherein: the polymerization inhibitor is one or more of hydroquinone, p-benzoquinone, p-toluenesulfonic acid, organic copper salt, quaternary ammonium salt and sulfur dioxide.
8. A method of using a photoinitiated tissue adhesive, comprising: the application method of the photoinitiated adhesive comprises the steps of uniformly coating the adhesive on a wound surface, enabling 10-20s cyanoacrylate to undergo self-curing reaction, and then irradiating the adhesive part for 5-10s by ultraviolet light or blue light to further initiate polymerization crosslinking reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310901039.XA CN116870237A (en) | 2023-07-21 | 2023-07-21 | Photoinitiated tissue adhesives and methods of use thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310901039.XA CN116870237A (en) | 2023-07-21 | 2023-07-21 | Photoinitiated tissue adhesives and methods of use thereof |
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| CN116870237A true CN116870237A (en) | 2023-10-13 |
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| CN202310901039.XA Pending CN116870237A (en) | 2023-07-21 | 2023-07-21 | Photoinitiated tissue adhesives and methods of use thereof |
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| Country | Link |
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| CN (1) | CN116870237A (en) |
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