JP5902084B2 - 両親媒性コポリマーを有する感圧シリコーン接着剤 - Google Patents
両親媒性コポリマーを有する感圧シリコーン接着剤 Download PDFInfo
- Publication number
- JP5902084B2 JP5902084B2 JP2012519694A JP2012519694A JP5902084B2 JP 5902084 B2 JP5902084 B2 JP 5902084B2 JP 2012519694 A JP2012519694 A JP 2012519694A JP 2012519694 A JP2012519694 A JP 2012519694A JP 5902084 B2 JP5902084 B2 JP 5902084B2
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- JP
- Japan
- Prior art keywords
- oligomer
- silicone
- vinyl
- monomer
- amphiphilic
- 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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- 229920001577 copolymer Polymers 0.000 title claims description 34
- 239000013464 silicone adhesive Substances 0.000 title description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 50
- -1 methacryloyl Chemical group 0.000 claims description 37
- 239000000178 monomer Substances 0.000 claims description 33
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 26
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 20
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- 229920002554 vinyl polymer Polymers 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 7
- AJXBTRZGLDTSST-UHFFFAOYSA-N amino 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)ON AJXBTRZGLDTSST-UHFFFAOYSA-N 0.000 claims description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 7
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 7
- 238000010526 radical polymerization reaction Methods 0.000 claims description 7
- 238000001802 infusion Methods 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 239000012736 aqueous medium Substances 0.000 claims 6
- 229910000077 silane Inorganic materials 0.000 claims 6
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 6
- 239000002954 polymerization reaction product Substances 0.000 claims 4
- 238000002386 leaching Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 description 16
- 239000000853 adhesive Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 230000003187 abdominal effect Effects 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000000416 hydrocolloid Substances 0.000 description 2
- 239000000017 hydrogel Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 2
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 2
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920006264 polyurethane film Polymers 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- SMDROGSFTRLOLU-UHFFFAOYSA-N 3-trimethylsilyloxysilylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[SiH2]O[Si](C)(C)C SMDROGSFTRLOLU-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 229920006187 aquazol Polymers 0.000 description 1
- 239000012861 aquazol Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229920005605 branched copolymer Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003213 poly(N-isopropyl acrylamide) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000013271 transdermal drug delivery Methods 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/18—Suspension polymerisation
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J143/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers
- C09J143/04—Homopolymers or copolymers of monomers containing silicon
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/10—Block or graft copolymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F13/00—Bandages or dressings; Absorbent pads
- A61F2013/00361—Plasters
- A61F2013/00655—Plasters adhesive
- A61F2013/00697—Plasters adhesive elastomer-, e.g. rubber- based
- A61F2013/00702—Plasters adhesive elastomer-, e.g. rubber- based silicon-based
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
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Description
シリコーン感圧接着剤は、経皮的な薬剤送達、創傷被覆材、瘢痕被覆材、および他の健康管理の適用において広く使用される。これらの接着剤は、一般に、シリケート樹脂とポリジメチルシロキサン(PDMS)流体との縮合生成物、またはビニルおよび水素化物含有PDMSとヒドロシリル化反応によって硬化したシリケート樹脂との反応性ブレンドである(非特許文献1)。これらの接着剤は、生体適合性で皮膚にやさしく、そして環境が乾燥しているときに医療装置を身体にしっかりと接着させる。しかしながら、皮膚の発汗中のような湿潤条件下では、疎水性シリコーン接着剤は、皮膚に対するその粘着性を失い、そのことは、被覆材が時期尚早に身体からはずれることをもたらし得る。
本発明は、新規の両親媒性シリコーンコポリマーを有するシリコーン感圧接着剤組成物を含む。本発明に従うシリコーン感圧接着剤組成物は、生体表面に接着することに適している。上記感圧接着剤は、少なくとも1つのシリコーンモノマーまたはオリゴマーと少なくとも1つの親水性または両親媒性のモノマーまたはオリゴマーとの反応生成物である両親媒性コポリマーを含み、上記両親媒性コポリマーが水性媒体に溶解せず、そして10,000g/molよりも大きい分子量を有する。
両親媒性コポリマーは、親水性および/または両親媒性モノマーと共重合する重合可能なシリコーンモノマーに基づく。
フリーラジカル重合によるポリ(TRIS)ベースのランダムコポリマーの合成のための代表的な手順は、例としてポリ(TRIS−コ−N,N’−ジメチルアミノエチルメタクリレート)(DMAEMA)(重量で3:1))を用いて、次の通りである:4.5gのTRISおよび1.5gのDMAEMAを25mLの耐圧反応フラスコに加えた。次に0.045gのVAZO 67を上記フラスコに移した。次に上記フラスコに14gの酢酸エチルを添加して30wt%の溶液を得た。この混合物を、澄んだ溶液が得られるまでやさしく振とうした。次に窒素で2分間フラッシュし、密閉し、65℃のオイルバスに6時間置いたままにした。これに続いて、溶媒を室温で36時間蒸発させて、より粘性のある溶液を生成し、それを次にポリエチレンフィルムの上に乗せて、さらに2日間乾燥させ、最終的に減圧乾燥した。軟らかく粘着性の固体であるコポリマーを、脱イオン水、そして、H2O/メタノール(50/50 v/v)の混合物中で洗浄した。
(実施例1)
両親媒性コポリマーを含むシリコーンゲル接着剤の調製のための代表的な手順は、次の通りである。NuSil MED−6345 Part AおよびPart Bを1:1の比で使用した。次にHMDS中のポリ(TRIS−コ−NIPAM)(3:1のモノマー重量比)溶液を添加し、その結果、接着剤ゲルは、結局、5wt%の固体コポリマーを含んだ。この混合物を完全に撹拌し、次にポリウレタンフィルム上にコーティングし、溶媒の蒸発のために1時間乾燥させた。その後、上記接着剤をオーブンの中で60℃にて3時間硬化させた。100%両親媒性のコポリマーの場合、コポリマーをHMDS中で溶解させ、ポリウレタンフィルムの上へコーティングし、次にオーブンの中で乾燥させた。接着剤の1インチ×1.5インチのストリップを、乾燥および湿潤環境下での粘着性についてヒト被験体で試験した。乾燥粘着性については、テープを、除去前に腹部領域に8時間固定した。湿潤粘着性については、テープをヒト被験体の腹部皮膚に接着し、次に40分〜60分の有酸素活動後に、テープを取り外した。乾燥および湿潤条件下での粘着性調査の結果を表1に示した。
乾燥粘着性を、指を用いて室温で測定した。粘着性を評するために0〜5の範囲を用いた(5=優れた粘着性、0=粘着性なし)。湿潤接着強度を、水に5分間浸してあった(そして、各測定の前に水にさっとつけ、取り出した)舌圧子を用いて測定した。ポリマーフィルムを酢酸エチル中での20wt%溶液から出し、5時間乾燥させ、インキュベーター内で35℃にて一晩、湿潤環境で平衡化し、次に取り出し、すぐに測定した。(全ての他の材料についての湿潤粘着性を、他に言及しない限りこの方法で測定した。)凝集力は、残留物を残すことも、崩壊することもなく基材から取り外される接着剤フィルムの能力を示す。凝集力を1〜5の尺度で測定した。(5=無傷なフィルムで残留物なし、1=多量の残留物がホスト基材上に残る、低い凝集力)
Claims (6)
- 生体表面に接着するのに適しているシリコーン感圧接着剤組成物であって、ここで該感圧接着剤は、少なくとも1つのシリコーンモノマーまたはオリゴマーと少なくとも1つの親水性または両親媒性のモノマーまたはオリゴマーとのフリーラジカル重合反応生成物である両親媒性コポリマーを含み、該両親媒性コポリマーが
a)水性媒体に溶解せず、そして
b)10,000g/molよりも大きい分子量を有し、
該シリコーンモノマーが、メタクリロイルアルキルシロキシシラン、ビニルアルキルシロキシシラン、ビニルアルコキシシラン、またはそれらの組み合わせであり、
該シリコーンオリゴマーが、ビニル、メタクリレート、アクリレート、およびそれらの組み合わせから選択される反応性基を有するポリジメチルシロキサンであり、
該親水性または両親媒性のモノマーまたはオリゴマーが、アクリルアミド、N−アルキルアクリルアミド、N,N−ジアルキルアクリルアミド、N−アルキルアミノアルキルアクリルアミド、メタクリルアミド、アクリル酸ならびにそのエステルおよび塩、メタクリル酸ならびにそのエステルおよび塩、アミノメタクリレート、N−アルキルアミノアクリレート、N−アルキルアミノメタクリレート、無水マレイン酸およびその誘導体、アルケニル無水物およびその誘導体、ビニルエーテル、ならびにそれらの組み合わせから選択される、
シリコーン感圧接着剤組成物。 - 医療用具を生体表面に接着させるのに適しているシリコーン感圧接着剤組成物であって、少なくとも1つのシリコーンモノマーまたはオリゴマーと少なくとも1つの親水性または両親媒性のモノマーまたはオリゴマーとのフリーラジカル重合反応生成物である両親媒性コポリマーの0.1%〜100%を含み、該両親媒性コポリマーが
a)水性媒体に溶解せず;
b)10,000g/molよりも大きい分子量を有し、そして
c)水分の存在下で浸出せず、
ここで該シリコーンモノマーが、メタクリロイルアルキルシロキシシラン、ビニルアルキルシロキシシラン、ビニルアルコキシシラン、またはそれらの組み合わせであり、
該シリコーンオリゴマーが、ビニル、メタクリレート、アクリレート、およびそれらの組み合わせから選択される反応性基を有するポリジメチルシロキサンであり、
該親水性または両親媒性のモノマーまたはオリゴマーが、アクリルアミド、N−アルキルアクリルアミド、N,N−ジアルキルアクリルアミド、N−アルキルアミノアルキルアクリルアミド、メタクリルアミド、アクリル酸ならびにそのエステルおよび塩、メタクリル酸ならびにそのエステルおよび塩、アミノメタクリレート、N−アルキルアミノアクリレート、N−アルキルアミノメタクリレート、無水マレイン酸およびその誘導体、アルケニル無水物およびその誘導体、ビニルエーテル、ならびにそれらの組み合わせから選択される、
シリコーン感圧接着剤組成物。 - 造瘻器具であって、該器具の身体接触表面上にシリコーン感圧接着剤組成物を含み、かつ、該器具を身体に接着させるのに適し、ここで該感圧接着剤は、少なくとも1つのシリコーンモノマーまたはオリゴマーと少なくとも1つの親水性または両親媒性のモノマーまたはオリゴマーとのフリーラジカル重合反応生成物である両親媒性コポリマーを含み、該両親媒性コポリマーが
a)水性媒体に溶解せず;そして
b)10,000g/molよりも大きい分子量を有し、
ここで該シリコーンモノマーが、メタクリロイルアルキルシロキシシラン、ビニルアルキルシロキシシラン、ビニルアルコキシシラン、またはそれらの組み合わせであり、
該シリコーンオリゴマーが、ビニル、メタクリレート、アクリレート、およびそれらの組み合わせから選択される反応性基を有するポリジメチルシロキサンであり、
該親水性または両親媒性のモノマーまたはオリゴマーが、アクリルアミド、N−アルキルアクリルアミド、N,N−ジアルキルアクリルアミド、N−アルキルアミノアルキルアクリルアミド、メタクリルアミド、アクリル酸ならびにそのエステルおよび塩、メタクリル酸ならびにそのエステルおよび塩、アミノメタクリレート、N−アルキルアミノアクリレート、N−アルキルアミノメタクリレート、無水マレイン酸およびその誘導体、アルケニル無水物およびその誘導体、ビニルエーテル、ならびにそれらの組み合わせから選択される、
造瘻器具。 - 創傷被覆材であって、該被覆材の身体接触表面上にシリコーン感圧接着剤組成物を含み、かつ、該被覆材を身体に接着させるのに適し、ここで該感圧接着剤は、少なくとも1つのシリコーンモノマーまたはオリゴマーと少なくとも1つの親水性または両親媒性のモノマーまたはオリゴマーとのフリーラジカル重合反応生成物である両親媒性コポリマーを含み、該両親媒性コポリマーが
a)水性媒体に溶解せず;そして
b)10,000g/molよりも大きい分子量を有し、
ここで該シリコーンモノマーが、メタクリロイルアルキルシロキシシラン、ビニルアルキルシロキシシラン、ビニルアルコキシシラン、またはそれらの組み合わせであり、
該シリコーンオリゴマーが、ビニル、メタクリレート、アクリレート、およびそれらの組み合わせから選択される反応性基を有するポリジメチルシロキサンであり、
該親水性または両親媒性のモノマーまたはオリゴマーが、アクリルアミド、N−アルキルアクリルアミド、N,N−ジアルキルアクリルアミド、N−アルキルアミノアルキルアクリルアミド、メタクリルアミド、アクリル酸ならびにそのエステルおよび塩、メタクリル酸ならびにそのエステルおよび塩、アミノメタクリレート、N−アルキルアミノアクリレート、N−アルキルアミノメタクリレート、無水マレイン酸およびその誘導体、アルケニル無水物およびその誘導体、ビニルエーテル、ならびにそれらの組み合わせから選択される、
創傷被覆材。 - 外科用装置、カテーテル、および静脈内送達装置を身体に接着させるための固定器具であって、該器具の身体接触表面上にシリコーン感圧接着剤組成物を含み、かつ、該固定器具を身体に接着させるのに適し、ここで該感圧接着剤は、少なくとも1つのシリコーンモノマーまたはオリゴマーと少なくとも1つの親水性または両親媒性のモノマーまたはオリゴマーとのフリーラジカル重合反応生成物である両親媒性コポリマーを含み、該両親媒性コポリマーが
a)水性媒体に溶解せず;そして
b)10,000g/molよりも大きい分子量を有し、
ここで該シリコーンモノマーが、メタクリロイルアルキルシロキシシラン、ビニルアルキルシロキシシラン、ビニルアルコキシシラン、またはそれらの組み合わせであり、
該シリコーンオリゴマーが、ビニル、メタクリレート、アクリレート、およびそれらの組み合わせから選択される反応性基を有するポリジメチルシロキサンであり、
該親水性または両親媒性のモノマーまたはオリゴマーが、アクリルアミド、N−アルキルアクリルアミド、N,N−ジアルキルアクリルアミド、N−アルキルアミノアルキルアクリルアミド、メタクリルアミド、アクリル酸ならびにそのエステルおよび塩、メタクリル酸ならびにそのエステルおよび塩、アミノメタクリレート、N−アルキルアミノアクリレート、N−アルキルアミノメタクリレート、無水マレイン酸およびその誘導体、アルケニル無水物およびその誘導体、ビニルエーテル、ならびにそれらの組み合わせから選択される、
固定器具。 - 輸液用器具であって、被覆材の身体接触表面上にシリコーン感圧接着剤組成物を含み、かつ、該輸液用器具を身体に接着させるのに適し、ここで該感圧接着剤は、少なくとも1つのシリコーンモノマーまたはオリゴマーと少なくとも1つの親水性または両親媒性のモノマーまたはオリゴマーとのフリーラジカル重合反応生成物である両親媒性コポリマーを含み、該両親媒性コポリマーが
a)水性媒体に溶解せず;そして
b)10,000g/molよりも大きい分子量を有し、
ここで該シリコーンモノマーが、メタクリロイルアルキルシロキシシラン、ビニルアルキルシロキシシラン、ビニルアルコキシシラン、またはそれらの組み合わせであり、
該シリコーンオリゴマーが、ビニル、メタクリレート、アクリレート、およびそれらの組み合わせから選択される反応性基を有するポリジメチルシロキサンであり、
該親水性または両親媒性のモノマーまたはオリゴマーが、アクリルアミド、N−アルキルアクリルアミド、N,N−ジアルキルアクリルアミド、N−アルキルアミノアルキルアクリルアミド、メタクリルアミド、アクリル酸ならびにそのエステルおよび塩、メタクリル酸ならびにそのエステルおよび塩、アミノメタクリレート、N−アルキルアミノアクリレート、N−アルキルアミノメタクリレート、無水マレイン酸およびその誘導体、アルケニル無水物およびその誘導体、ビニルエーテル、ならびにそれらの組み合わせから選択される、
輸液用器具。
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CA2766116A1 (en) | 2011-01-13 |
AU2010270603A1 (en) | 2012-01-19 |
CA2766120A1 (en) | 2011-01-13 |
US20120108749A1 (en) | 2012-05-03 |
AU2010270610A1 (en) | 2012-01-19 |
EP2451852A1 (en) | 2012-05-16 |
CA2766120C (en) | 2018-08-14 |
WO2011005839A1 (en) | 2011-01-13 |
JP2012532960A (ja) | 2012-12-20 |
JP6215874B2 (ja) | 2017-10-18 |
AU2010270603B2 (en) | 2015-05-07 |
US10294317B2 (en) | 2019-05-21 |
US20180362690A1 (en) | 2018-12-20 |
EP2451852A4 (en) | 2014-07-16 |
AU2010270610B2 (en) | 2015-05-07 |
US8679581B2 (en) | 2014-03-25 |
EP2451852B1 (en) | 2019-04-17 |
CA2766116C (en) | 2017-12-05 |
EP2451883B1 (en) | 2019-04-17 |
US20120109036A1 (en) | 2012-05-03 |
US11426485B2 (en) | 2022-08-30 |
EP2451883A4 (en) | 2014-07-02 |
EP2451883A1 (en) | 2012-05-16 |
JP2012532959A (ja) | 2012-12-20 |
JP2016006183A (ja) | 2016-01-14 |
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