WO2005102403A1 - Silicone skin adhesive gels - Google Patents
Silicone skin adhesive gels Download PDFInfo
- Publication number
- WO2005102403A1 WO2005102403A1 PCT/US2005/009518 US2005009518W WO2005102403A1 WO 2005102403 A1 WO2005102403 A1 WO 2005102403A1 US 2005009518 W US2005009518 W US 2005009518W WO 2005102403 A1 WO2005102403 A1 WO 2005102403A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- siloxane resin
- silicone gel
- alkenyl
- vinyl
- Prior art date
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Classifications
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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
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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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/58—Adhesives
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- 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
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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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- 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
Definitions
- the present invention relates to a method for improving the adhesion of silicone gels to medical substrates by including a hydroxy-substituted siloxane resin in the gel formulations.
- Pressure sensitive adhesives PSAs
- silicone PSAs comprise condensed blends of silicone fluids and silicone resins.
- silicone PSAs are applied as thin coatings between substrates to be adhered together. It is likewise known in the art to use silicone PSAs in medical applications. For instance, it is known to use silicone PSAs to adhere transdermal drug delivery devices and medical prosthesis to patients.
- Silicone PSAs can have a number of properties that limit their use in medical applications. For instance, the adhesive strength of silicone PSAs is often so great that a patient's skin or the object to be adhered can be damaged on removal of the PSA. Additionally, silicone PSAs often exhibit cold flow properties at skin temperature. As such, the resultant inflexible layers of PSA can be very uncomfortable on the patient's body.
- silicone PSAs are harder and more rigid than silicone gels. As such, if the material is to be applied to soft body tissues such as skin, very thin layers must be used to retain the flexibility of the tissue. Finally, silicone PSAs often delaminate from the carrier leaving a coating of the PSA on the skin and/or the object to be adhered. Not only is this a cosmetic problem, but it also limits the ability to reuse the adhesive. Silicone gels are also known in the art. These gels have been used, for example, as dielectrics, vibration dampers and in medical therapy for cutaneous scars or injuries (e.g., abrasions, surgical areas or burns).
- the silicone gel is in the form of a sheet with one tacky surface for adherence to the patient's skin and one non-tacky surface to inhibit undesirable adhesion to the gel (e.g., the patient's clothing). Since the silicone gels are softer than PSAs, when they are applied to tissue such as the skin they have a skin-like texture that provides a less disruptive interface with the skin (e.g., it is more flexible). When silicone gels are joined with certain substrates such as plastics, however, the adhesive strength between the silicone gel and the plastic is often so weak that it delaminates.
- the silicone gel when used as an adhesive to adhere a medical substrate to a human or animal body, the gel often delaminates from the substrate before the gel delaminates from the human or animal body to which it is applied.
- the art has suggested treating the substrate such as a plastic surface with means such as corona, flame, and plasma. While such treatments are beneficial, they are difficult to implement on a continuous coating line. Moreover, the treatments must be precisely controlled to prevent damage to the substrate (e.g., heat damage) or inhibit the cure of the silicone material. Finally, such processes often cannot be used on fabric or porous non-woven materials because the uncured gel material can soak through.
- a second approach to improve adhesion to substrates, especially plastic substrates, is to use a primer material, such as a titanate material, on the substrate.
- a primer material such as a titanate material
- This approach requires additional processing steps.
- the present inventors have now improved the adhesion of silicone gels to medical substrate by including a hydroxy-substituted siloxane resin in the gel formulation.
- the present invention provides a method for adhering a medical substrate to a human or animal.
- the method comprises affixing a layer of a silicone gel between a medical substrate and a human or animal.
- the silicone gel used in this process contains between about 2 and about 45 wt. % of a hydroxy substituted siloxane resin.
- the present invention provides a silicone gel comprising the reaction product of 10% to 80 wt.% of an alkenyl-substituted polydiorganosiloxane; 2% to 45 wt.% of a hydroxy functional siloxane resin; 1% to 30% wt.
- silicone gels lack cold flow and, as such, are sufficiently soft to allow comfortable use by a human or animal.
- the method of the present invention comprises using a hydroxy-substituted siloxane resin in a silicone gel to increase the adhesion of the gel to a medical substrate.
- the substrate can comprise plastics, natural macromolecular materials (e.g. collagen, wood, cork, leather), metals, glass, ceramics or composites.
- the substrates used herein can comprise plastics or resins known in the art.
- polyolefins including polyethylenes (low density polyethylenes, high density polyethylenes and the like), polypropylenes, polybutylenes, polymethylpentenes, polyethylene-vinyl acetate (EVA) and their copolymers, polyvinyls, polyvinyl acetates, polyvinyl alcohol, polyvinylbutyral, polyvinyl formal, polyurethanes and polyurethane-ureas, polyvinyl chloride derivatives (polyvinyl chloride, polyvinylene chloride, copolyvinylchloride-propylene), polystyrenes and their copolymers (copolystyrene-butadiene, polystyrene acrylonitrile, polyacrylonitrile-butadiene-styrene), polyacrylic and polyacrylates derivatives (polymethyl methacrylate, ethylene/butyl acrylate copolymer, ethylene/methyl acrylate copolymer
- the substrates used in the present invention can also be a continuous or perforated plastic film, a nonwoven film, a knitted fabric, a fiber network, a foam, a metal, a glass or ceramic material. If desired, the materials can be treated with, for example, a corona, flame, plasma or a primer such as a titanate to increase the adhesion.
- the substrate used is plastic and, alternatively, the plastic is polyurethane. While the substrate can be in nearly any configuration, in one embodiment of the invention the substrate is in the form of a medical substrate.
- a "medical substrate” is a substrate that is used in the treatment, maintenance or improvement of a human or animal. Such substrates can be used in combination with other materials for such purpose.
- a "silicone gel” is an elastic, jelly-like solid material formed by lightly cross-linking silicone polymers.
- a "PSA” has low or no resiliency.
- the silicone gel used in the present invention should be chosen to have the properties desired for the end application. Important properties can include softness, friability and strength.
- the gels used in the present invention are generally formed from linear or branched silicones having reactive groups thereon. Such reactive groups undergo a cross-linking reaction during curing. Examples of cross-linking reactions include the hydrosilylation reaction in which a silicone having an Si-H reactive group reacts with a silicone having an aliphatically unsaturated reactive group in the presence of a hydrosilylation catalyst.
- the gels are obtained by reacting at least one alkenyl-substituted polydiorganosiloxane, such as a polydimethylsiloxane having silicon-bonded alkenyl groups such as vinyl, allyl or hexenyl groups, at least one organosiloxane containing silicon-bonded hydrogen atoms, at least one hydroxy containing siloxane resin and at least one catalyst for the reaction of the SiH groups with the Si-alkenyl groups, such as a platinum metal or compounds or complexes thereof.
- Such compositions cure at normal ambient temperatures, but curing can be expedited by exposure to elevated temperatures, e.g., from about 40°C to about 140°C.
- alkenyl-substituted polydiorganosiloxanes are known in the art as described, for example, in US patent number 3,983,298 which is hereby incorporated by reference.
- Suitable alkenyl groups contain from 2 to about 6 carbon atoms and are exemplified by, but not limited to vinyl, allyl, and hexenyl.
- the alkenyl groups in this component may be located at terminal, pendant (non-terminal), or both terminal and pendant positions.
- the remaining silicon-bonded organic groups in the alkenyl-substituted polydiorganosiloxane are independently selected from the group consisting of monovalent hydrocarbon and monovalent halogenated hydrocarbon groups free of aliphatic unsaturation.
- These groups typically contain from 1 to about 20 carbon atoms, alternatively from 1 to 8 carbon atoms and are exemplified by, but not limited, to alkyl such as methyl, ethyl, propyl, and butyl; aryl such as phenyl; and halogenated alkyl such as 3,3,3-trifluoropropyl.
- alkyl such as methyl, ethyl, propyl, and butyl
- aryl such as phenyl
- halogenated alkyl such as 3,3,3-trifluoropropyl.
- at least 50 percent of the organic groups in the alkenyl-substituted polydiorganosiloxane are methyl.
- the structure of the alkenyl-substituted polydiorganosiloxane is typically linear, however it may contain some branching due to the presence of trifunctional siloxane units.
- the viscosity of the alkenyl-substituted polydiorganosiloxane can be any desired. For example, it can be less than 100,000 mm /second, alternatively less than 80,000 mm /second, and alternatively 300 - 3,000 mm 2 /second. It should be noted that additional alkenyl- substitution can be included in the form of a resin as described below. Methods for preparing the alkenyl-substituted polydiorganosiloxanes of the present invention, such as condensation of the corresponding halosilanes or equilibration of cyclic polydiorganosiloxanes, are well known in the art.
- the alkenyl-substituted polydiorganosiloxanes can be used in the composition of this invention in an amount of 10-90 wt. % based on the weight of the composition, alternatively 40-90 wt. %, and alternatively 50-80 wt.%.
- the amount of alkenyl group present in the alkenyl-substituted polydiorganosiloxane is between 0.05% - 1% wt%, alternatively 0.05 to 1 wt. % vinyl based on the weight of the alkenyl-substituted polydiorganosiloxane.
- the organosiloxane containing silicon-bonded hydrogen atoms are also known in the art as described, for example in US patent number 3,983,298.
- the hydrogen atoms in this component may be located at terminal, pendant (non-terminal), or both terminal and pendant positions.
- the remaining silicon-bonded organic groups in this component are independently selected from the group consisting of monovalent hydrocarbon and monovalent halogenated hydrocarbon groups free of aliphatic unsaturation.
- These groups typically contain from 1 to about 20 carbon atoms, alternatively from 1 to 8 carbon atoms, and are exemplified by, but not limited to alkyl such as methyl, ethyl, propyl, and butyl; aryl such as phenyl; and halogenated alkyl such as 3,3,3-trifluoropropyl.
- at least 50 percent of the organic groups in the organosiloxane containing silicon-bonded hydrogen atoms are methyl.
- the structure of the organosiloxane containing silicon-bonded hydrogen atoms is typically linear, however it may contain some branching due to the presence of trifunctional siloxane units.
- the viscosity of the organosiloxane containing silicon-bonded hydrogen atoms can be any desired. For example, it can be less than 100,000 mm 2 /second and, alternatively, 5 - 500 mm 2 /second.
- the organosiloxanes containing silicon-bonded hydrogen atoms can be used in the composition of this invention in an amount of 1-30 wt. % based on the weight of the composition, alternatively 5-20 wt %, and alternatively 5-15 wt. %.
- the amount of hydrogen group present in the organosiloxane containing silicon-bonded hydrogen atoms is between 0.05% - 1.44 wt% based on the weight of the organosiloxane containing silicon-bonded hydrogen atoms.
- Methods of preparing the organosiloxane containing silicon-bonded hydrogen atoms of the present invention by co-hydrolysis of the appropriate chlorosilanes are known in the art.
- the hydrosilylation catalyst promotes the addition reaction of the alkenyl-substituted polydiorganosiloxane with the organosiloxane containing silicon-bonded hydrogen.
- the hydrosilylation catalyst can be any of the well known hydrosilylation catalysts comprising a platinum group metal, a compound containing a platinum group metal, or a microencapsulated platinum group metal or compound containing same.
- platinum group metals include platinum, rhodium, ruthenium, palladium, osmium and iridium.
- Platinum and platinum compounds are preferred catalysts based on their high activity level in hydrosilylation reactions.
- One class of platinum catalysts is the complexes of chloroplatinic acid with certain vinyl-containing organosiloxane compounds disclosed by Willig in U.S. Pat. No. 3,419,593, which is hereby incorporated by reference.
- a specific catalyst of this type is the reaction product of chloroplatinic acid and l,3-diethenyl-l,l,3,3-tetramethyldisiloxane.
- the hydrosilylation catalyst is present in an amount sufficient to cure the composition of the present invention.
- the concentration of the catalyst is sufficient to provide from 0.1 to 500 ppm (part per million), alternatively from 1 to 100 ppm, alternatively from 1 to 50 parts per million of a platinum group metal, based on the combined weight of the other components.
- the gels of the present invention also contain at least one hydroxy-substituted siloxane resin. This resin increases the adhesion of the gel to the medical substrate and the skin.
- This resin comprises (M units) and SiO 4/ units (Q units) wherein each R is independently a linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms. R can be unsubstituted or substituted with halogen atoms. Each R can be identical or different, as desired.
- the hydrocarbon group of R can be exemplified by alkyl groups such as methyl, ethyl, propyl, butyl, hexyl, octyl3,3,3-trifluoropropyl, chloromethyl, and decyl, alkenyl groups such as vinyl and hexenyl, cycloaliphatic groups such as cyclohexyl, aryl groups such as phenyl, tolyl, and xylyl, chlorophenyl, and aralkyl groups such as benzyl, styryl and alpha- methylstyryl.
- alkyl groups such as methyl, ethyl, propyl, butyl, hexyl, octyl3,3,3-trifluoropropyl, chloromethyl, and decyl
- alkenyl groups such as vinyl and hexenyl
- cycloaliphatic groups such as cyclohexy
- each R group is an independently selected alkyl or alkenyl group comprising 1 to 8 carbon atoms or aryl group comprising 6 to 9 carbon atoms.
- each R group is independently selected from methyl and vinyl. If an alkenyl group is present in the resin, typically the mole % of R groups present as alkenyl groups is less than 10%, alternatively less than 5%. For example, if the resin contains vinyl groups, typically they are present in an amount of less than 5 wt. % of the resin solids, alternatively less than 2.5 wt. % of the resin solids, alternatively 1.5-2 wt. % of the resin solids.
- the molar ratio of R3SiO ⁇ /2 (M units) to Si ⁇ 4/2 (Q units) can be from 0.6:1 to 4:1.
- the molar ratio of M:Q can be from 0.6: 1 to 1.9: 1.
- the molar ratio of M:Q can be from 0.6:1 to 1.0:1.
- the resins can also contain triorganosiloxy units (T units), for example 0.5 to 1 friorganosiloxy group for every SiO 4/ unit, alternatively 0.6 to 0.9 triorganosiloxy group for every SiO 4/2 unit. It should be noted that more than 1 resin could be included in the present invention.
- At least one of the resins should have the silanol content as described below but, by the same token, one could have the silanol capped so that there is substantially no silanol present.
- other resins can also be added to the composition of this invention.
- organic resins could be added if desired.
- a vinyl-functional organic resin can be added.
- a majority of all R groups are methyl and the total number of R groups that have olefinic unsaturation is no more than 0.5% of all R groups.
- substantially all of the R groups are methyl.
- substantially all of the R groups are substantially free of olefinic unsatuaration.
- 2 resins are included - one in which substantially all of the R groups are methyl and the other in which 3.5 to 4 mole % of the R groups are vinyl and substantially all of the remaining R groups are methyl.
- the resins also contain silicon-bonded hydroxyl groups ranging from about 0.01 up to 5 weight percent of the resin, alternatively from about 1 to about 5 wt. % of the resin.
- Resins comprising R 3 Si ⁇ ! /2 units and SiO 4/2 units are well known in the art. These copolymers are described, for example, in U.S. Pat. Nos. 3,936,582, 2,676,182, and 2,857,356 which are all hereby incorporated by reference.
- the resinous copolymers can be prepared by cohydrolysis of a mixture of silanes having four hydrolyzable groups, e.g., silicon tetrachloride, and triorganosilanes having one hydrolyzable group, e.g., trimethylchlorosilane, in the proper ratio.
- a specific method for the preparation of these resinous copolymers is described in U.S. Pat. No.
- gels of the present invention can be included in the gels of the present invention including, but not limited to, fillers, pigments, low temperature cure inhibitors, additives for improving adhesion, cross-linkers (e.g., Si-H cross-linkers), chain extenders, pharmaceutical agents, cosmetic agents, natural extracts, fluids or other materials conventionally used in gels.
- cross-linkers e.g., Si-H cross-linkers
- chain extenders e.g., pharmaceutical agents, cosmetic agents, natural extracts, fluids or other materials conventionally used in gels.
- silicone fluids silicone waxes, silicone polyethers, and other polymers including, for example, hydrophilic polymers such as sodium polyacrylic acid, PVA, PVP, polyacrylic adhesive, cellulose and polysaccharide (which can make the gel more hydrophilic and more permeable to moisture).
- Still other optional components include rheology modifiers such as thickening agents, thixotropic agents and materials that react with the ingredients if the gel such as castor oil or maleates that can react with the hydroxyl groups of the resin.
- the gel contains substantially no filler (e.g., less than 5 wt.%, alternatively less than 1 wt. %, alternatively les than 0.1 wt. %).
- the gel contains substantially no solvent (e.g., less than 5 wt.%, alternatively less than 1 wt. %, alternatively less than 0.1 wt. %).
- Active agents to be used in this invention can include any solid or liquid material that can be bound in the composition and subsequently released at the desired rate. The active agents should also not interfere with the curing of the silicone formulation to an unacceptable extent. Suitable active agents include cosmetics, personal care, cosmeceuticals, therapeutic or diagnostic materials, pesticides, herbicides, and the like.
- Therapeutic active agents which may be employed include, for example, antiacne agent, antibiotic, antiseptic, antifungal, antibacterial, antimicrobial, biocides, antiinflanunatory, astringents, hormones, anticancer agents, smoking cessation compositions, cardiovascular, histamine blocker, bronchodilator, analgesic, antiarrythmic, antihistamine, alpha- 1 blocker, beta blocker, ACE inhibitor, diuretic, antiaggregant, sedative, tranquillizer, anticonvulsant, anticoagulant agents, vitamins, antiaging agents, agents for treating gastric and duodenal ulcers, anticellulites, proteolytic enzymes, healing factors, cell growth nutrients, peptides and others.
- Suitable therapeutic active agents include penicillins, cephalosporins, tetracyclines, macrolides, epinephrine, amphetamines, aspirin, acetominophen, barbiturates, catecholamines, benzodiazepine, thiopental, codeine, morphine, procaine, lidocaine, benzocaine, sulphonamides, ticonazole, perbuterol, furosamide, prazosin, prostaglandins, salbutamol, indomethicane, diclofenac, glafenine, dipyridamole, theophylline and retinol.
- active, agents could be cosmetics such as perfumes, UN protectors, shaving products, deodorants or the like. Suitable cosmetics are known to those skilled in the art.
- Some additional examples of the cosmetics, personal care, and cosmeceutical ingredients and pharmaceutical excipients that may be used herein may be found in the CTFA ingredient Database and the handbook of pharmaceutical excipients and can include, for example, absorbents, anticacking agents, antioxidants, antistatic agents, astringents, binders, buffering agents, bulking agents, chelating agents, colorants, cosmetic astringents, cosmetic biocides, deodorant agents, emollients, external analgesics, film formers, flavoring agents, fragrance ingredients, humectants, lytic agents, moisturizing agents, occlusivity enhancers, opacifying agents, oxidizing and reducing agents, penetration enhancers, pesticides, plasticizers, preservatives, skin bleaching agents, skin conditioning agents,
- polyethylene glygol derivatives of alcohols and fatty alcohols alkoxylated amides, alkoxylated amines, alkoxylated carboxylic acids, amides including salts (e.g. ceramides), amines, amino acids including salts and alkyl substituted derivatives, esters, alkyl substituted and acyl derivatives, polyacrylic acids, acrylamide copolymers, adipic acid copolymers, alcohols, aminosilicones, biological polymers and derivatives, butylene copolymers, carbohydrates (e.g. polysaccharides, chitosan and derivatives), carboxylic acids, carbomers, esters, ethers and polymeric ethers (e.g.
- collagen collagen
- synthetic polymers including salts, siloxanes and silanes, sorbitan derivatives, sterols, sulfonic acids and derivatives and waxes.
- antiacne agents are Salicylic acid and Sulfur.
- antifungal agents are Calcium Undecylenate, Undecylenic Acid, Zinc Undecylenate, and Povidone-Iodine.
- antimicrobial agents are Alcohol, Benzalkonium Chloride, Benzethonium Chloride, Hydrogen Peroxide, Methylbenzethonium Chloride, Phenol, Poloxamer 188, and Povidone-Iodine.
- antioxidants are Acetyl Cysteine, Arbutin, Ascorbic Acid, Ascorbic Acid Polypeptide, Ascorbyl Dipalmitate, Ascorbyl Methylsilanol Pectinate, Ascorbyl Palmitate, Ascorbyl Stearate, BHA, p- Hydroxyanisole, BHT, t-Butyl Hydroquinone, Caffeic Acid, Camellia Sinensis Oil, Chitosan Ascorbate, Chitosan Glycolate, Chitosan Salicylate, Chlorogenic Acids, Cysteine, Cysteine HCI, Decyl Mercaptomethylimidazole, Erythorbic Acid, Diamylhydroquinone, Di-t- Butylhydroquinone, Dicetyl Thiodipropionate, Dicyclopentadiene/t-Butylcresol Copolymer, Digalloyl Trioleate, Dilauryl Thiodipropionate, Dimyristyl
- Phenylthioglycolic Acid Phloroglucinol, Potassium Ascorbyl Tocopheryl Phosphate, Thiodiglycolamide, Potassium Sulfite, Propyl Gallate, Rosmarinic Acid, Rutin, Sodium Ascorbate, Sodium Ascorbyl/Cholesteryl Phosphate, Sodium Bisulfite, Sodium Erythorbate, Sodium Metabisulfide, Sodium Sulfite, Sodium Thioglycolate, Sorbityl Furfural, Tea Tree (Melaleuca Aftemifolia) Oil, Tocopheryl Acetate, Tetrahexyldecyl Ascorbate,
- Tetrahydrodiferuloylmethane Tocopheryl Linoleate/Oleate, Thiodiglycol, Tocopheryl Succinate, Thiodiglycolic Acid, Thioglycolic Acid, Thiolactic Acid, Thiosalicylic Acid, Thiotaurine, Retinol, Tocophereth-5, Tocophereth-10, Tocophereth-12, Tocophereth-18, Tocophereth-50, Tocopherol, Tocophersolan, Tocopheryl Linoleate, Tocopheryl Nicotinate, Tocoquinone, o-Tolyl Biguanide, Tris(Nonylphenyl) Phosphite, Ubiquinone, and Zinc Dibutyldithiocarbamate.
- cosmetic biocides are Aluminum Phenolsulfonate, Ammonium Phenolsulfonate, Bakuchiol, Benzalkonium Bromide, Benzalkonium Cetyl Phosphate, Benzalkonium Chloride, Benzalkonium Saccharinate, Benzethonium Chloride, Potassium Phenoxide, Benzoxiquine, Benzoxonium Chloride, Bispyrithione, Boric Acid, Bromochlorophene, Camphor Benzalkonium Methosulfate, Captan, Cetalkonium Chloride, Cetearalkonium Bromide, Cetethyldimonium Bromide, Cetrimonium Bromide, Cetrimonium Chloride, Cetrimonium Methosulfate, Cetrimonium Saccharinate, Cetrimonium Tosylate, Cetylpyridinium Chloride, Chloramine T, Chlorhexidine, Chlorhexidine Diacetate, Chlorhex, Ch
- External analgesics are Benzyl Alcohol, Capsicum Oleoresin (Capsicum Frutescens Oleoresin), Methyl Salicylate, Camphor, Phenol, Capsaicin, Juniper Tar (Juniperus Oxycedrus Tar), Phenolate Sodium (Sodium Phenoxide), Capsicum (Capsicum Frutescens), Menthol, Resorcinol, Methyl Nicotinate, and Turpentine Oil (Turpentine).
- oxidizing agents are Ammonium Persulfate, Calcium Peroxide, Hydrogen Peroxide, Magnesium Peroxide, Melamine Peroxide, Potassium Bromate, Potassium Caroate, Potassium Chlorate, Potassium Persulfate, Sodium Bromate, Sodium Carbonate Peroxide, Sodium Chlorate, Sodium Iodate, Sodium Perborate, Sodium Persulfate, Strontium Dioxide, Strontium Peroxide, Urea Peroxide, and Zinc Peroxide.
- reducing agents are Ammonium Bisufite, Ammonium Sulfite, Ammonium Thioglycolate, Ammonium Thiolactate, Cystemaine HCI, Cystein, Cysteine HCI, Ethanolamine Thioglycolate, Glutathione, Glyceryl Thioglycolate, Glyceryl Thioproprionate, Hydroquinone, p-Hydroxyanisole, Isooctyl Thioglycolate, Magnesium Thioglycolate, Mercaptopropionic Acid, Potassium Metabisulfite, Potassium Sulfite, Potassium Thioglycolate, Sodium Bisulfite, Sodium Hydrosulfite, Sodium
- Hydroxymethane Sulfonate Sodium Metabisulfite, Sodium Sulfite, Sodium Thioglycolate, Strontium Thioglycolate, Superoxide Dismutase, Thioglycerin, Thioglycolic Acid, Thiolactic Acid, Thiosalicylic Acid, and Zinc Formaldehyde Sulfoxylate.
- An example of a skin bleaching agent is Hydroquinone.
- skin protectants are Allantoin, Aluminum Acetate, Aluminum Hydroxide, Aluminum Sulfate, Calamine, Cocoa Butter, Cod Liver Oil, Colloidal Oatmeal, Dimethicone, Glycerin, Kaolin, Lanolin, Mineral Oil- Petrolatum, Shark Liver Oil, Sodium Bicarbonate, Talc, Witch Hazel, Zinc Acetate, Zinc Carbonate, and Zinc Oxide.
- sunscreen agents are Aminobenzoic Acid, Cinoxate, Diethanolamine Methoxycinnamate, Digalloyl Trioleate, Dioxybenzone, Ethyl 4- [bis(Hydroxypropyl)] Aminobenzoate, Glyceryl Aminobenzoate, Homosalate, Lawsone with Dihydroxyacetone, Menthyl Anthranilate, Octocrylene, Octyl Methoxycinnamate, Octyl Salicylate, Oxybenzone, Padimate O, Phenylbenzimidazole Sulfonic Acid, Red Petrolatum, Sulisobenzone, Titanium Dioxide, and Trolamine Salicylate.
- UN light absorbing agents are Acetaminosalol, Allatoin PABA, Benzalphthalide, Benzophenone, Benzophenone 1-12, 3-Benzylidene Camphor, Benzylidenecamphor Hydrolyzed Collagen Sulfonamide, Benzylidene Camphor Sulfonic Acid, Benzyl Salicylate, Bornelone, Bumetriozole, Butyl Methoxydibenzoylmethane, Butyl PABA, Ceria/Silica, Ceria Silica Talc, Cinoxate, DEA-Methoxycinnamate, Dibenzoxazol Naphthalene, Di-t-Butyl Hydroxybenzylidene Camphor, Digalloyl Trioleate, Diisopropyl Methyl Cinnamate, Dimethyl PABA Ethyl Cetearyldimonium Tosylate, Dioctyl Butamido Triazone, Diphenyl Carbomethoxy Acetoxy
- the consistency, strength, softness and tackiness of the gel is determined by a number of factors including the ratio of reactive groups in the materials, the viscosity of the polymers, the quantity of ingredients including resin and the like.
- the composition used in the present invention comprises 65-75 wt. % of an alkenyl- substituted polydiorganosiloxane, 1-3 wt. % of a second alkenyl-substituted polydiorganosiloxane, 3-6 wt. % of a vinyl and hydroxy substituted siloxane resin, 9-15 wt. % of a hydroxy substituted siloxane resin, 9- 15 wt.
- the composition used in the present invention comprises 60-70 wt. % of an alkenyl-substituted polydiorganosiloxane, 5-7 wt. % of a vinyl and hydroxy substituted siloxane resin, 6-10 wt. % of a hydroxy substituted siloxane resin, 8-12 wt. % of an organosiloxane containing terminal silicon-bonded hydrogen atoms and a hydrosilylation catalyst which has relatively medium adhesion to the skin.
- the composition used in the present invention comprises 70-80 wt. % of an alkenyl-substituted polydiorganosiloxane, 3-8 wt. % of a vinyl and hydroxy substituted siloxane resin, 9-15 wt. % of a hydroxy substituted siloxane resin, 8- 12 wt. % of an organosiloxane containing terminal silicon-bonded hydrogen atoms and a hydrosilylation catalyst which has relatively medium-high adhesion to the skin.
- the composition used in the present invention comprises 50-70 wt.
- the composition used in the present invention comprises 25-45 wt. % of an alkenyl-substituted polydiorganosiloxane, 10-20 wt. % of a vinyl and hydroxy substituted siloxane resin, 15-25 wt.
- gels in one embodiment of the invention have a penetration of 50 mm to 300 mm with a cone category 1806-1 weighted 62.5 g. Generally, the gels have a coating weight in the range of about 100 to 4500 g/m 2 . In one embodiment of the invention, the densities are in the range of about 150 to 1200 g/m 2 .
- Such gels would generally have thicknesses in the range of about 0.15 to about 5 mm, and in one embodiment of the invention the gels have a thickness of 0.2 to 1.5 mm.
- the adhesive strength of the silicone gels should be sufficient to maintain adhesion to the medical substrate. Similarly, if the gel is to be adhered to a human or animal, the adhesive strength of the gel should be sufficient to ensure that it remains attached to the human or animal and yet not so strong that the human or animal is not excessively damaged when the gel is removed. As noted above, traditional silicone gels often do not adhere well to certain substrates such as plastics and, thus, delaminate.
- the applicants herein have discovered that by adding a hydroxy-substituted siloxane resin to the silicone gel, the adhesive strength of the silicone gel to the plastic substrate is increased.
- the tack is generally between 50 g and 500 g, and in one embodiment of the invention the tack is in the range of 150 g to 350 g.
- the adhesive property can also be measured using a Texture Analyzer (1/2 inch diameter cylinder Derlin probe, 100 gf applied for 5 seconds and 10 mm/s separation speed) the tack is generally between 50 gf to 500 gf.
- the silicone gels should also be sufficiently soft and flexible to ensure comfort to the user.
- the surfaces of the gels to be adhered to the medical substrate or the patient can be covered or protected with a release liner prior to use.
- the adhesive strength between the silicone gel and such release liner is obviously less than that between the gel and the substrate such that the release liner can be peeled off of the silicone gel revealing the underlying tacky gel.
- Suitable release liner materials are known in the art and can include, for instance, a plastic or multi-ply material such as a silicone, a fluorinated silicone, a fluorine polymer, polyethylene, polypropylene, polyethylene terephthalate (PET), ethylvinyl acetate polymer, a PNC or the like.
- the release liner could be made from a wide variety of materials (e.g., paper) coated with a suitable release coating.
- the surface of the release coating can be smooth, embossed or in any other desirable form. If the adhesive strength of the gel is still not sufficient to adhere it to the medical substrate, either the surface of the gel or the surface of the plastic can be primed.
- Suitable primers include titanate materials such as organic titanates commercialized by Dupont® under Tradename Tyzor®; organic zirconate; hydrogen functional siloxanes such as dimethyl, methylhydrogen siloxane, trimethylsiloxy-terminated, methylhydrogen siloxane, trimethylsiloxy-terminated, dimethyl siloxane, hydrogen-terminated, and methylhydrogen cyclosiloxanes; and platinum derivatives such as 1 ,3 -diethenyl- 1,1,3,3 -tetramethyldisiloxane complexes (platinum).
- the composition of the present invention can be made by mixing the components in the desired ratio. This can be done in conventional mixing equipment such as static mixers and the like.
- the order of mixing is not important other than curing may initiate when the Si-H, Si-Ninyl and hydrosilylation catalyst are mixed.
- the composition can be pre-compounded and supplied in multi-part system, preferably as a two-part A & B system.
- the gel layer can also be made by any desirable technique.
- One example comprises preforming the gel (e.g., as a sheet) by known procedures e.g. by molding, calendering, extruding, spraying, brushing, applying by hand, coating or casting on, for example, a releasable substrate. The gel is then brought together with the medical substrate.
- the gel may be preformed (e.g., as a sheet) by casting and curing the gel- forming composition on the medical substrate.
- the gel forming composition may be applied by techniques such as spraying, coating, bar coating, etc.
- the gel forming composition can be used as a dispersion or solution in a volatile solvent such as an organic solvent, a low molecular weight silicone or other suitable solvent and, thereafter, the solvent can be evaporated.
- An alternative method is to use a gel forming composition that does not require a substantial quantity of solvent, for example less than 5 wt. %, alternatively less than 1 wt. %.
- the gel forming composition may be applied as a continuous layer, a coating with void areas, a perforated layer, a patterned layer, or a discontinuous layer forming various designs such as lines, dots, circles, networks etc.
- the substrate onto which the gel is applied in the above processes can be any surface that will impart the desired configuration to the compositions. Thus, it may be a continuous belt onto which the gel forming composition is spread. Depending on the consistency of the compositions, the substrate may have barriers at its edges to restrict the flow of the compositions until cure takes place. In one embodiment of the invention, the substrate is a releaseable substrate to allow the gel to be easily removed and used.
- the substrate can be a preformed blister package made of any of the conventional blister packaging materials including, for example, polyvinyl chloride, polypropylene, polyethylene, polyester, paper or composites with or without suitable release coatings.
- the composition formed above can be any size and shape desired based on the final use. For instance, it can be circular, square or rectangular and it can vary from a few square centimeters to in excess of several hundred square cm.
- the compositions of the present invention are useful in applications where the adhesion provided ⁇ y a silicone gel is useful.
- the silicone gel adhesives of this invention are, however, particularly adapted for adhering medical substrates on patients.
- Such substrates include devices such as breast prosthesis, catheters, cannulas, drainage bags, uridomes, incontinence devices, hygiene napkins, pouches, false hairpieces (e.g., toupees), tubes, ostomy and related devices, surgery drapes, facial masks, gloves, other medical devices and the like.
- these materials can be used for the manufacturing of silicone adhesive tapes (e.g. PU non-woven fabric with gel on it), gel sheeting (e.g. PU film with gel on it), wound dressings (e.g. PU film or PU foam with gel on it), bandages, adhesive strips, surgery drapes (PE film with gel on it), adhesive medical devices (e.g.
- PNC tube with gel latex catheter with gel on it
- hygiene napkins PE film with gel
- external prosthesis e.g. PU external breast prosthesis with gel on it
- topical or transdermal patches e.g., drug delivery
- fragrance/cosmetics patches and the like.
- the softness of the gels in mm is measured using a P ⁇ RG penetrometer with a 65mm diameter/62.5g cone probe.
- the sample tested is prepared by mixing the ingredients, pouring 80g to lOOg of the sample in a plastic cup and curing it at 103°C-140°C for 60 min.
- the peel adhesion in ⁇ (newton) is measured using a TA-XT Plus Texture Analyzer or Tensile Testing equipment (e.g. Instron).
- the sample is prepared by mixing the ingredients, coating them on the appropriate substrate and curing the coating.
- the coated substrate is then cut in 2.5 cm strips and a polyester film (Mylar) is laminated to the surface.
- the polyurethane adhesion in ⁇ (newton) is measured with a TA-XT Plus Texture Analyzer or Tensile Testing equipment (e.g. Instron).
- strip size 2.5 cm wide X 12.5 cm long
- the gel strip is laminated to the PSA strip minimizing air entrapment and a roller is used to adhere samples together.
- the laminated strips are condition in an oven for 20 minutes at 50°C, allowed to cool completely (minimum 10 minutes), and then test on Texture Analyzer using the gel laminate adhesion test (180° peel test). Each sample was run in triplicate and the average force (N) was reported. Any observed characteristics were noted.
- Example 1 (control) - The following ingredients were mixed in the amounts indicated: vinyl terminated PDMS - 400 mPa.s 100 parts platinum catalyst 0.01%
- Adhesion promoter (titanate) 1 %
- Adhesion promoter (titanate) 1%
- Example 10 (replicate of example 9)
- Viscosity mPa.s
- Softness penetration mm/10
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- Hematology (AREA)
- Surgery (AREA)
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- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Metal-Oxide And Bipolar Metal-Oxide Semiconductor Integrated Circuits (AREA)
- Cosmetics (AREA)
- Adhesive Tapes (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT05726039T ATE470458T1 (en) | 2004-04-08 | 2005-03-18 | SILICONE SKIN ADHESIVE GEL |
EP05726039A EP1737504B1 (en) | 2004-04-08 | 2005-03-18 | Silicone skin adhesive gels |
US10/592,443 US20070202245A1 (en) | 2004-04-08 | 2005-03-18 | Silicone Skin Adhesive Gels With Enhanced Adhesion To Plastic |
DE602005021767T DE602005021767D1 (en) | 2004-04-08 | 2005-03-18 | SILICON HAUTKLEBEGELS |
JP2007507334A JP4849477B2 (en) | 2004-04-08 | 2005-03-18 | Silicone skin adhesive gel |
DK05726039.0T DK1737504T3 (en) | 2004-04-08 | 2005-03-18 | Silicone skin application gel |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US56080504P | 2004-04-08 | 2004-04-08 | |
US60/560,805 | 2004-04-08 |
Publications (1)
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WO2005102403A1 true WO2005102403A1 (en) | 2005-11-03 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2005/009518 WO2005102403A1 (en) | 2004-04-08 | 2005-03-18 | Silicone skin adhesive gels |
Country Status (7)
Country | Link |
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US (1) | US20070202245A1 (en) |
EP (1) | EP1737504B1 (en) |
JP (1) | JP4849477B2 (en) |
AT (1) | ATE470458T1 (en) |
DE (1) | DE602005021767D1 (en) |
DK (1) | DK1737504T3 (en) |
WO (1) | WO2005102403A1 (en) |
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- 2005-03-18 JP JP2007507334A patent/JP4849477B2/en active Active
- 2005-03-18 US US10/592,443 patent/US20070202245A1/en not_active Abandoned
- 2005-03-18 WO PCT/US2005/009518 patent/WO2005102403A1/en active Application Filing
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Also Published As
Publication number | Publication date |
---|---|
DE602005021767D1 (en) | 2010-07-22 |
EP1737504A1 (en) | 2007-01-03 |
EP1737504B1 (en) | 2010-06-09 |
DK1737504T3 (en) | 2010-07-19 |
JP2007532179A (en) | 2007-11-15 |
US20070202245A1 (en) | 2007-08-30 |
JP4849477B2 (en) | 2012-01-11 |
ATE470458T1 (en) | 2010-06-15 |
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