WO2011005846A1 - Amphiphilic silicone copolymers for pressure sensitive adhesive applications - Google Patents

Amphiphilic silicone copolymers for pressure sensitive adhesive applications Download PDF

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Publication number
WO2011005846A1
WO2011005846A1 PCT/US2010/041191 US2010041191W WO2011005846A1 WO 2011005846 A1 WO2011005846 A1 WO 2011005846A1 US 2010041191 W US2010041191 W US 2010041191W WO 2011005846 A1 WO2011005846 A1 WO 2011005846A1
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pdms
pressure sensitive
amphiphilic
sensitive adhesive
vinyl
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French (fr)
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Mahesh Sambasivam
James Crivello
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Convatec Technologies Inc
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Convatec Technologies Inc
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Priority to CA2766120A priority Critical patent/CA2766120C/en
Priority to EP10797773.8A priority patent/EP2451883B1/en
Priority to US13/382,219 priority patent/US8679581B2/en
Priority to JP2012519696A priority patent/JP2012532960A/ja
Priority to AU2010270610A priority patent/AU2010270610B2/en
Publication of WO2011005846A1 publication Critical patent/WO2011005846A1/en
Anticipated expiration legal-status Critical
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    • 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
    • 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
    • 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
    • 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
    • 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
    • C09J183/14—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • 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
    • C09J2483/00—Presence of polysiloxane

Definitions

  • Silicone pressure sensitive adhesives are widely used in transdermal drug delivery, wound dressings, scar dressings, and other healthcare applications.
  • These adhesives are typically a condensation product of silicate resin and polydimethylsiloxane (PDMS) fluid, or a reactive blend of vinyl- and hydride- containing PDMS and a silicate resin cured via hydrosilylation reaction (Dow).
  • PDMS polydimethylsiloxane
  • Corning Literature Silicone Pressure Sensitive Adhesives (2002). These adhesives are biocompatible, gentle on the skin, and securely attach medical devices to the body when the environment is dry. However, under moist conditions such as during skin perspiration, the hydrophobic silicone adhesives lose their adhesion to skin, which can lead to the dressing detaching from the body
  • the present approach is to add a suitable amphiphilic silicone copolymer to a silicone pressure sensitive adhesive.
  • An ideal amphiphilic silicone copolymer suitable for such applications should possess high cohesive strength, high moisture vapor
  • MVTR transmission rate
  • high pressure sensitive adhesion to surfaces maintain adhesion even under moist conditions, and should not leach out components or leave a residue.
  • Commercially available amphiphilic silicone copolymers are typically based on grafted poly(ethylene glycol). These copolymers are low molecular weight liquids, which are typically used as surfactants or defoamers. Addition of such low molecular weight copolymers can affect the adhesive performance because of surface migration under moist conditions and lead to a reduction in adhesion.
  • Graiver, et al. used aldehyde-functional silicones as reactive sites for vinyl copolymerization in the presence of a copper redox system (D. Graiver, G. T.
  • the resulting copolymers with a silicone content of about 30-50% were shown to reduce the surface tension of plastics, such as PET, PMMA, and polyurethane.
  • Yildiz, et al. synthesized poly(N-isopropylacrylamide) hydrogels using diacrylate- terminated PDMS as the crosslinker Y. Yildiz, N. Uyanik, and C. Erbil, J. Macromol. Sci., Part A: Pure and Applied Chemistry, 43, 1091 -1106 (2006).
  • the resulting hydrogels were found to have higher compression moduli compared to the conventional crosslinker, N,N'-methylene bis-acrylamide. This was attributed to the hydrophobic interactions between PDMS segments in the network.
  • Scheme 2 shows the synthetic scheme for an amphiphilic silicone graft copolymer using a PDMS macrointiator.
  • Figure 1 shows the 1 H NMR spectrum of PDMS/MAA/EE 2/1/1 terpolymer.
  • Figure 2 shows the 1 H NMR spectrum of PDMS/MAA/EE 2/2/2 terpolymer.
  • Figure 3 shows the 1 H NMR spectra of PDMS/MAA/EE 2/1/1 (maroon)
  • Figure 4 shows the TGA of PDMS precursor, PDMS/MAA/EE 2/1/1 and 2/2/2 terpolymers.
  • Figure 5 shows the TGA of GantrezTM AN-169 (MAA/ME copolymer).
  • Figure 6 shows the DSC of ⁇ , ⁇ -hydride-terminated PDMS precursor (DMS-H25 from Gelest Inc.).
  • Figure 7 shows the DSC of PDMS/MAA/EE 2/1/1.
  • Figure 8 shows the DSC of PDMS/MAA/EE 2/2/2.
  • Figure 9 shows the DSC of GantrezTM AN-169.
  • Figure 10 shows the FTIR of PDMS/MAA/EE terpolymers and PDMS starting material.
  • Figure 11 shows the Reference FTIR of MAA/ME Copolymer (GantrezTM AN-169). DESCRIPTION OF THE INVENTION
  • This invention relates to a pressure sensitive adhesive comprising one or more amphiphilic copolymers of polydimethylsiloxane, wherein the copolymer is prepared using a polydimethylsiloxane or polymethylhydrogensiloxane macroinitiator and at least one reactive hydrophilic or amphiphilic monomer, oligomer, macromer and combinations thereof.
  • the reactive hydrophilic or amphiphilic monomer is selected from a group consisting of N-vinyl caprolactams, vinyl esters, vinyl ethers, unsaturated acids or anhydrides and their salts, acrylates, methacrylates, acrylamides, methacrylamides, N-alkyl acrylamides, cyanate esters, hydroxy-alkyl acrylamides, glycidyl esters, glycidyl ethers, allyl monomers, and combinations thereof.
  • the reactive hydrophilic or amphiphilic oligomer and macromer are selected from a group consisting of an polyalkyleneoxide, polyether, polyurethane, polyester, polyamide, polysaccharide, polypeptide, polyacrylate, polymethacrylate, polyacrylamide, with reactive groups selected from vinyl, epoxy, allyl, and combinations thereof.
  • a macroinitiator is a compound capable of initiating a polymerization reaction, wherein the molecular weight of the said compound is at least 200 g/mol.
  • the invention includes a pressure sensitive adhesive comprising one or more amphiphilic copolymers of poly(dimethylsiloxane)-poly(maleic anhydride-vinyl ethyl ether) (PDMS/MAA/EE) and a silicone gel adhesive blended together.
  • a pressure sensitive adhesive comprising one or more amphiphilic copolymers of poly(dimethylsiloxane)-poly(maleic anhydride-vinyl ethyl ether) (PDMS/MAA/EE) and a silicone gel adhesive blended together.
  • the invention further includes a medical device having a pressure sensitive adhesive comprising one or more amphiphilic copolymers of polydimethylsiloxane, wherein the copolymer is prepared using a polydimethylsiloxane or polymethylhydrogensiloxane macroinitiator and at least one reactive hydrophilic or amphiphilic monomer or oligomer or macromer.
  • a medical device having a pressure sensitive adhesive comprising one or more amphiphilic copolymers of polydimethylsiloxane, wherein the copolymer is prepared using a polydimethylsiloxane or polymethylhydrogensiloxane macroinitiator and at least one reactive hydrophilic or amphiphilic monomer or oligomer or macromer.
  • medical devices for which such an adhesive is applicable include ostomy devices, wound management devices, skin and incontinence care and infusion devices. Synthesis of Polydimethylsiloxane-poly(maleic anhydride-alt-viny
  • the synthesis of the terpolymers were based on the copolymerization of maleic anhydride and vinyl ethyl ether (PDMS/MA/VEE) using a PDMS macrointiator (Scheme 1 ) according to the procedure described by Crivello et al. (J. V. Chvello, D. A. Conlon, and J. L. Lee, J. Polym. Sci. Part A: Polym. Chem., 24, 1197-1215 (1986)).
  • the uniqueness of the present invention includes the incorporation of hydrophilic groups into a siloxane polymer which surprisingly yields a polymer additive suitable for pressure sensitive adhesives with desireable peel adhesion, moisture management and biocompatibility.
  • This polymer is listed to have a molecular weight of 17,200 g/mol and about 0.01 mol% Si-H groups.
  • the macroinitiator was prepared by reacting bis(dimethylvinylsilyl)benzopinacolate with ⁇ , ⁇ -hydhde-terminated PDMS precursor in the presence of Karstedt's catalyst.
  • the polydimethylsiloxane macroinitiator was mixed with an equimolar ratio of maleic anhydride and vinyl ethyl ether in a 150 ml_ of dried toluene in a 250 ml_ flask equipped with paddle stirrer, reflux condenser and nitrogen inlet.
  • the macroinitiator to comonomer molar ratios (PDMS/MA/VEE) synthesized were 2/1/1 and 2/2/2.
  • the polymerization was initiated by raising the temperature to 80 0 C and the reaction was continued for 5 hours. At the end of the reaction, the terpolymer was precipitated with methanol, and dried at room temperature under vacuum. The polymerization yield was about 95% in both compositions. It should be noted that even though Scheme 1 shows a triblock structure, it is anticipated that there are diblocks and multiblocks also in the mixture.
  • Scheme 1 Silicone block copolymer synthesis
  • a PDMS-hydride is reacted with an oxirane containing compound such as cyclohexene oxide (shown here as an example), glycidyl methyl ether, etc. to synthesize an amphiphilic PDMS copolymer
  • Samples PDMS/MAA/EE 2/1/1 and PDMS/MA/VEE 2/2/2 were analyzed by 1 H NMR.
  • the terpolymers were dissolved in a mixture of in a 50:50 v/v mixture of non-deuterated 2-propanol and toluene-c/ ⁇ for analysis.
  • Thermogravimethc Analysis was performed on the copolymer samples and the ⁇ , ⁇ -hydhde-terminated PDMS precursor (DMS-H25). The presence of any volatile fraction was analyzed as well as the degradation behavior of the terpolymer systems. All samples were run from 30 0 C to 900 0 C at 10 °C/minute in air using sample weight ranging from 2 to 12 mg.
  • DSC Differential Scanning Calohmetry
  • FTIR Fourier transform infrared
  • Table 1 shows the characterization results of PDMS block and graft copolymers synthesized per reaction Scheme II. Except for the PDMS/GME graft copolymer, which seem to be tacky, all the other copolymers were non tacky.
  • PDMS polydimethylsiloxane
  • CHO cyclohexene oxide
  • GME glycidyl methyl ether
  • VP vinyl pyrrolidone
  • VA vinyl acetate
  • MA maleic anhydride
  • VEE vinylethyl ether
  • VPEG vinyl terminated polyethylene oxide
  • DOM dioctyl maleate Characterization of PDMS/VEE/MA terpolymers
  • Figures 1 and 2 show the NMR spectra for the terpolymers.
  • the two terpolymer samples produced similar signals.
  • the large signals at 4.89 ppm, 3.92 ppm, and 1.13 ppm are due to the 2-propanol solvent.
  • the signals at 7.08 ppm, 6.98 ppm, and 2.12 ppm are due to the toluene-c/ 8 solvent.
  • the sharp signal at 0.14 ppm is due to PDMS from the sample material.
  • Software prediction of alternating copolymers of maleic anhydride and vinyl ethyl ether predict signals at 1.1 ppm, 1.6 ppm, and three signals between 3.3 ppm and 3.4 ppm.
  • the TGA of ⁇ , ⁇ -hydride-terminated PDMS precursor along with the copolymer samples are shown in Figure 4.
  • the precursor there is a low temperature weight loss accounting for approximately 3% that is likely due to residual monomer or solvent in the oligomer.
  • the major weight loss which starts around 330 0 C is due to the degradation of the silicone polymer backbone.
  • Both terpolymers (2/1/1 and 2/2/2 molar ratios) show four distinct regions - the first one is up to 50 0 C, the second from 140-250 0 C, the third from 250-325 0 C, and the fourth from 325-550 0 C.
  • the first two regions are probably due to residual solvent and monomers.
  • the nature of the second weight loss is less obvious but could be due to residual toluene (used in the synthesis) with a boiling point of 110 0 C, residual octamethylcyclotetrasiloxane (D4) with a boiling point of 175 0 C, or residual maleic anhydride with a boiling point of 202 0 C.
  • the third and fourth regions are attributed to the terpolymer degradation.
  • the terpolymer compositions show approximately 7% char remaining, which is expected due to the lower level of PDMS as compared to the neat PDMS precursor.
  • Polydimethylsiloxane is known to produce a char in air due to the formation of silica. Most hydrocarbon based compounds will completely oxidize in air and will not leave any residue.
  • GantrezTM AN-169 was analyzed using the same conditions (see Figure 5). As expected, this copolymer did not show any char.
  • the degradation profile of the copolymer is consistent with the lower temperature degradation profiles of the terpolymers with four distinct regions. This indicates the presence of vinyl ether and maleic anhydride comonomers in the terpolymer system.
  • the amount of residue is assumed to be related to the amount of PDMS in the terpolymer.
  • the amount of PDMS in the terpolymer was calculated by taking the ratio of char weight between the terpolymer and the neat precursor. Based on these calculations, the weight percent of PDMS in the terpolymers was calculated to be less than 20% (Table 2), which is considerably lower than expected based on the initial loading in the reactor and from NMR analysis. These differences could be due to an altered charring mechanism of siloxane chain in the presence of the hydrocarbon comonomers.
  • DSC data for the PDMS precursor (DMS-H25 from Gelest) from the first and second runs are shown in Figure 6. This data shows a significant endotherm in both the first and second heats at around -40 0 C which is attributed to the melting temperature of PDMS.
  • Figures 7 and 8 are the DSC scans for the two terpolymers
  • Figure 9 shows the first and second heat, respectively, of Gantrez AN-169, which is reported to have a T 9 of 154 0 C according to the supplier literature (ISP corporation).
  • Figure 10 shows the FTIR spectra for the PDMS/MAA/EE terpolymers overlaid with the PDMS precursor (bottom curve).
  • the precursor shows fingerprint bands at 1258 cm “1 (Si-CH3), 1067 cm “1 and 1013 cm “1 (Si-O-Si stretching vibration), and 793 cm “1 (Si-C stretching and CH 3 rocking) for PDMS.
  • the terpolymers show distinct bands at 1856 cm “1 and 1781 cm “1 which can be attributed to anhydride group.
  • a reference spectrum of maleic anhydride/vinyl methyl ether (GantrezTM AN-169 from ISP corporation) provided in Figure 11 provides a close match to the terpolymer samples in Figure 10. This confirms the presence of PDMS and MAA/EE moieties in the copolymers.
  • the amphiphilic silicone pressure sensitive adhesive was prepared by blending PDMS/MAA/EE terpolymer into a conventional silicone gel adhesive at 20 wt % loading level, prior to curing the gel. The reactive blend was then coated on a polyurethane film using a Werner-Mathis coater and cured at 150 0 C for 3 minutes. The coating thickness was about 10 mils.
  • the moisture vapor transmission rate (MVTR) of the adhesives was measured using the upright cup method ASTM E96- 00. Table 3 shows the summary of tackines and % change in moisture vapor transmission rate compared to neat silicone gel adhesive.
  • the composition with the amphiphilic copolymer additive was still a pressure sensitive adhesive as it was tacky to touch, and the MVTR showed an increase of about 800% compared to the neat silicone gel.
  • Amphiphilic silicone terpolymers were synthesized based on a polydimethylsiloxane macroinitiator containing thermolyzable bis(silylpinacolate) groups in the polymer backbone.
  • the terpolymers showed solubility in a toluene/2- propanol mixture but not the individual solvents indicating the presence of covalently bonded hydrophobic and hydrophilic segments.
  • the mild swelling of the samples in alkali solution further supports the presence of hydrophilic and hydrophobic domains.
  • the presence of both PDMS and MA ⁇ /EE components were confirmed by NMR, TGA, DSC and FTIR.

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PCT/US2010/041191 2009-07-07 2010-07-07 Amphiphilic silicone copolymers for pressure sensitive adhesive applications Ceased WO2011005846A1 (en)

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CA2766120A CA2766120C (en) 2009-07-07 2010-07-07 Amphiphilic silicone copolymers for pressure sensitive adhesive applications
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US13/382,219 US8679581B2 (en) 2009-07-07 2010-07-07 Amphiphilic silicone copolymers for pressure sensitive adhesive applications
JP2012519696A JP2012532960A (ja) 2009-07-07 2010-07-07 感圧接着剤の適用のための両親媒性シリコーンコポリマー
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US20120109036A1 (en) 2012-05-03
US8679581B2 (en) 2014-03-25
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AU2010270610B2 (en) 2015-05-07
US20120108749A1 (en) 2012-05-03
AU2010270610A1 (en) 2012-01-19
EP2451883A4 (en) 2014-07-02
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EP2451852A1 (en) 2012-05-16
JP2012532960A (ja) 2012-12-20
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US11426485B2 (en) 2022-08-30
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US10294317B2 (en) 2019-05-21
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CA2766116C (en) 2017-12-05
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EP2451852A4 (en) 2014-07-16
JP6215874B2 (ja) 2017-10-18

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