Hardening components

Abstract

The curable composition comprises a first organopolysiloxane compound having one or more groups containing silicon atoms bonded to hydrogen atoms, and a second organopolysiloxane compound having one or more groups containing carbon-carbon multiple bonds. The curable composition also comprises a hydrosilylation catalyst, an organopolysiloxane resin, a silver-containing antimicrobial agent, and a hydrophilic compound. The composition is an emulsion having a continuous phase and a discontinuous phase. The silver-containing antimicrobial agent and the hydrophilic compound are present in the discontinuous phase.

Description

[Technical Field]

[0001] This invention relates to a curable composition and its use. [Background technology]

[0002] Wound care bandages often contain an adhesive layer containing silver-containing compounds and / or other antimicrobial agents to help prevent infection and promote wound healing. Such an adhesive layer may be formed by applying the composition to a substrate and allowing the composition to cure.

[0003] Additives may be included to enhance the delivery of antimicrobial agents from the cured composition. Such additives may be used to swell the cured composition during use, allowing the antimicrobial agent to leach more freely from the adhesive layer. However, such additives are often incompatible with other components of the composition, and phase separation may be observed in the composition before curing. Phase separation before curing is undesirable because it can result in a non-uniform adhesive layer and / or a decrease in tackiness exhibited by the adhesive layer.

[0004] Therefore, it would be desirable to provide a composition that can overcome the aforementioned drawbacks. [Overview of the project]

[0005] Embodiments of a curable composition are provided.

[0006] In one embodiment, the curable composition comprises a first organopolysiloxane compound having one or more groups including a silicon atom bonded to a hydrogen atom, a second organopolysiloxane compound having one or more groups including a carbon-carbon multiple bond, a hydrosilylation catalyst, an organopolysiloxane resin, a silver-containing antimicrobial agent, and a hydrophilic compound. The composition is an emulsion having a continuous phase and a discontinuous phase. The antimicrobial agent and the hydrophilic compound are present in the discontinuous phase.

[0007] In other embodiments, the composition contains 0.5% by weight or more of organopolysiloxane resin based on the total weight of the composition. In one such embodiment, the composition contains 0.5 to 5% by weight of organopolysiloxane resin based on the total weight of the composition.

[0008] In some embodiments, the organopolysiloxane resin comprises M units and Q units.

[0009] In further embodiments, the curable composition does not show observable phase separation after at least 24 hours at 23°C and 55% relative humidity, or after centrifugation at 23°C and 5000 rpm for 5 minutes. In another such embodiment, the curable composition does not show observable phase separation after 90 days at 23°C and 55% relative humidity, or after centrifugation at 23°C and 5000 rpm for 5 minutes.

[0010] The interfacial tension between the continuous phase and the discontinuous phase is preferably less than 28 mN / m. In certain embodiments, the interfacial tension between the continuous phase and the discontinuous phase is 22 to 28 mN / m.

[0011] In one embodiment, the silver-containing antibacterial agent is a silver salt.

[0012] In further embodiments, the hydrophilic compound is a polyol. In one embodiment, the polyol is glycerol. In another embodiment, the hydrophilic compound is a polyhydric alcohol or a polyether.

[0013] In certain embodiments, the curable composition has a continuous phase comprising a polysiloxane network.

[0014] In other embodiments, the curable composition includes a hydrosilylation inhibitor.

[0015] In some embodiments, the antimicrobial agent and the hydrophilic compound are present in the discontinuous phase.

[0016] In other embodiments, a method for forming a gel-like adhesive is provided. In one embodiment, the method includes the steps of applying a curable composition to a substrate and curing the composition.

[0017] The above and other advantages of the present invention will be readily apparent to those skilled in the art from the following detailed description, in light of the accompanying drawings. [Brief explanation of the drawing]

[0018] [Figure 1] This graph shows the interfacial tension between the continuous phase and the discontinuous phase of an embodiment of the curable composition of the present invention. [Modes for carrying out the invention]

[0019] It should be understood that, unless expressly otherwise specified, various alternative adaptations and sequences of steps are possible with respect to the present invention. It should also be understood that the specific materials, compositions, articles, and methods described in the following specification are merely illustrative embodiments of the concept of the present invention. Therefore, specific characteristics, conditions, or other physical properties relating to the disclosed embodiments should not be considered limiting unless specifically stated.

[0020] In certain embodiments, a curable composition is provided. The curable composition is suitable for use in wound care bandages. For example, the composition may be used to provide an adhesive portion for wound care bandages. However, the curable composition is not limited to wound care applications and can be used in other applications where inhibiting microbial growth is desired. Such applications may be medical or non-medical.

[0021] The curable composition comprises a first organopolysiloxane compound. The first organopolysiloxane compound has one or more groups, each containing a silicon atom bonded to a hydrogen atom. The silicon atom bonded to a hydrogen atom may also be referred to herein as Si-bonded hydrogen or "SiH". In some embodiments, at least one of the one or more groups containing a silicon atom bonded to a hydrogen atom is a terminal group. In other embodiments, at least one of the one or more groups containing a silicon atom bonded to a hydrogen atom is a pendant group. In yet another embodiment, the first organopolysiloxane compound has two or more groups, each containing a silicon atom bonded to a hydrogen atom, where at least one of the two or more groups is a terminal group and at least one of the two or more groups is a pendant group.

[0022] Preferably, the first organopolysiloxane compound has two or more Si-bonded hydrogen atoms, is linear, cyclic, or branched, and is composed of units of general formula (I). R 4 c H d SiO (4-c-d) / 2 (I) R 4 In each generation, it is an aliphatic carbon-carbon multiple bond-free group, c is 0, 1, 2, or 3. d is 0, 1, or 2. However, the sum of c+d is 3 or less, and there are at least two Si-bonded hydrogen atoms per molecule.

[0023] In some embodiments, R 4 It may contain one or more monovalent or polyvalent groups, in which case the polyvalent groups, for example, divalent, trivalent, and tetravalent groups, bond to each other, for example, two or more, for example, two, three, or four, siloxy units of formula (I).

[0024] In other embodiments, R 4 -F, -Cl, -Br, OR can be interposed by oxygen atoms or by the group -C(O)- 6a monovalent group of a group containing -CN, -SCN, -NCO and SiC bonds, substituted or unsubstituted hydrocarbon groups, and a divalent group with both sides Si-bonded according to formula (I). R 4 When R contains a SiC-bonded substituted hydrocarbon group, preferred substituents include a halogen atom, a phosphorus-containing group, a cyano group, -OR 6 , NR 6 -, -NR 6 2, -NR 6 -C(O)-NR 6 2, -C(O)-NR 6 2, -C(O)R 6 , -C(O)OR 6 , -SO2-Ph and -C6F5. In such embodiments, R 6 represents, independently at each occurrence, identically or differently, a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and Ph is a phenyl group.

[0025] R 4 Further embodiments of R include an alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl group, hexyl group such as n-hexyl group, heptyl group such as n-heptyl group, octyl group such as n-octyl group and isooctyl group such as 2,2,4-trimethylpentyl group, nonyl group such as n-nonyl group, decyl group such as n-decyl group, dodecyl group such as n-dodecyl group and octadecyl group such as n-octadecyl group, cycloalkyl group such as cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl group, aryl group such as phenyl, naphthyl, anthryl and phenanthryl group, alkaryl group such as o-, m-, p-tolyl group, xylyl group and ethylphenyl group, and aralkyl group such as benzyl group, α- and β-phenylethyl group.

[0026] R 4If the substituent is, suitable examples include haloalkyl groups, e.g., 3,3,3-trifluoro-n-propyl group, 2,2,2,2',2',2'-hexafluoroisopropyl group, heptafluoroisopropyl group, haloaryl group, e.g., o-, m- and p-chlorophenyl group, -(CH2)-N(R 6 )C(O)NR 6 2, -(CH2) o -C(O)NR 6 2, -(CH2) o -C(O)R 6 ,-(CH2) o -C(O)OR 6 ,-(CH2) o -C(O)NR 6 2. -(CH2)-C(O)-(CH2) p C(O)CH3, -(CH2)-O-CO-R 6 ,-(CH2)-NR 6 -(CH2) p -NR 6 2, -(CH2) o -O-(CH2) p CH(OH)CH2OH, -(CH2) o (OCH2CH2) p Ure 6 ,-(CH2) o -SO2-Ph and -(CH2) o -O-C6F5 is included, R 6 And Ph correspond to the definitions shown above, and o and p are identical or different integers between 0 and 10.

[0027] R as a divalent group with Si bonds on both sides according to formula (I) 4 An example of this is the additional bonding that occurs due to the substitution of hydrogen atoms, R 4 The group is derived from the monovalent examples mentioned above, and examples of such groups include -(CH2)-, -CH(CH3)-, -C(CH3)2-, -CH(CH3)-CH2-, -C6H4-, -CH(Ph)-CH2-, -C(CF3)2-, and -(CH2) o -C6H4-(CH2) o -,-(CH2) o -C6H4-C6H4-(CH2) o-,-(CH2O) p (CH2CH2O) o ,-(CH2) o -O x -C6H4-SO2-C6H4-O x -(CH2) o -, x is 0 or 1, and Ph, o, and p have the definitions described above.

[0028] Preferably, R 4 This comprises a monovalent, SiC-bonded, optionally substituted hydrocarbon group having 1 to 18 carbon atoms, without aliphatic carbon-carbon multiple bonds, more preferably a monovalent, SiC-bonded hydrocarbon group having 1 to 6 carbon atoms, without aliphatic carbon-carbon multiple bonds, and more specifically a methyl or phenyl group.

[0029] In certain embodiments, the first organopolysiloxane compound preferably contains Si-bonded hydrogen in an amount ranging from 0.04 to 1.7 wt% based on the total weight of the first organopolysiloxane compound.

[0030] The molecular weight of the first organopolysiloxane compound is also within a broad range, for example, 10 2 ~10 6 The concentration can vary in g / mol. Therefore, the first organopolysiloxane compound may be, for example, a relatively low molecular weight SiH-functional oligosiloxane, such as tetramethyldisiloxane, or a silicone resin having SiH groups, or a high molecular weight polydimethylsiloxane having SiH groups in the chain or at the terminals.

[0031] In some embodiments, the first organopolysiloxane compound may be provided as all or part of component (A). In certain embodiments, component (A) may comprise a mixture of organopolysiloxanes comprising one or more embodiments of the first organopolysiloxane compound described above. For example, in one embodiment, component (A) may comprise a mixture of organopolysiloxanes comprising an organopolysiloxane having at least one terminal group containing a silicon atom bonded to a hydrogen atom, and an organopolysiloxane having at least one pendant group containing a silicon atom bonded to a hydrogen atom. Additional organopolysiloxanes may also be suitable for use in component (A).

[0032] As described above, component (A) may contain a mixture of molecules comprising two or more different organopolysiloxanes. Particularly preferred are low molecular weight SiH-functional compounds, such as tetrakis(dimethylsiloxy)silane and tetramethylcyclotetrasiloxane, and high molecular weight SiH-containing siloxanes, such as poly(hydrogenmethyl)siloxane and poly(dimethylhydrogenmethyl)siloxane with a viscosity of 10 to 20,000 mPa·s at 25°C, or similar SiH-containing compounds in which some of the methyl groups are replaced with 3,3,3-trifluoropropyl or phenyl groups.

[0033] The molecular structure of component (A) is not fixed, and in particular, the structure of relatively high molecular weight SiH-containing organopolysiloxanes, in other words, oligomers or polymers, may be linear, cyclic, branched, or resinous network-like. Linear and cyclic organopolysiloxanes are preferably of formula R 4 3SiO 1 / 2 , HR 4 2SiO 1 / 2 , HR 4 SiO 2 / 2 and R 4 2SiO 2 / 2 It is composed of units of R 4 The above definition applies. Branched and reticulated organopolysiloxanes further comprise trifunctional and / or tetrafunctional units, preferably of formula R 4SiO 3 / 2 , HSiO 3 / 2 and SiO 4 / 2 And R 4 The above definition applies.

[0034] The amount of component (A) in the curable composition is preferably such that the molar ratio of SiH groups to aliphatic unsaturated groups in the composition is 0.1 to 20, more preferably 0.3 to 2.0.

[0035] The curable composition comprises a second organopolysiloxane compound. The second organopolysiloxane compound has one or more groups containing carbon-carbon multiple bonds. The second organopolysiloxane compound may be provided as part of component (B). In these embodiments, the curable composition may be formed by providing component (B). Component (B) may comprise the second organopolysiloxane compound or another compound.

[0036] In some embodiments, the second organopolysiloxane compound may be a linear organopolysiloxane. In these embodiments, the second organopolysiloxane compound may have one or more terminal groups containing carbon-carbon multiple bonds, which may be referred to herein as aliphatic multiple bonds. In one such embodiment, the second organopolysiloxane compound may contain a SiC bond group having an aliphatic carbon-carbon multiple bond, which may be referred to herein as an aliphatic unsaturated group. If component (B) contains another linear compound, such compound may contain an aliphatic carbon-carbon multiple bond.

[0037] As described above, component (B) may comprise an organopolysiloxane compound or another compound. In embodiments in which component (B) comprises a silicon-free organic compound, such compound may comprise at least two aliphatic unsaturated groups. In some embodiments, the second organopolysiloxane compound has at least two aliphatic unsaturated groups. In certain embodiments, component (B) may comprise a mixture of compounds. In one such embodiment, component (B) may comprise a second organopolysiloxane compound having at least two aliphatic unsaturated groups and a silicon-free organic compound having at least two aliphatic unsaturated groups. In yet another embodiment, component (B) may comprise a mixture of separate organopolysiloxane compounds comprising the second organopolysiloxane compound, each of which may comprise an aliphatic carbon-carbon multiple bond. In these embodiments, the aliphatic carbon-carbon multiple bond may be located at a terminal group of the organopolysiloxane compound or at another group.

[0038] Examples of silicon-free organic compounds suitable for use in component (B) include 1,3,5-trivinylcyclohexane, 2,3-dimethyl-1,3-butadiene, 7-methyl-3-methylene-1,6-octadiene, 2-methyl-1,3-butadiene, 1,5-hexadiene, 1,7-octadiene, 4,7-methylene-4,7,8,9-tetrahydroindene, methylcyclopentadiene, and 5-vinyl-2-norbol. Nene, bicyclo[2.2.1]hepta-2,5-diene, 1,3-diisopropenylbenzene, vinyl group-containing polybutadiene, 1,4-divinylcyclohexane, 1,3,5-trialylbenzene, 1,3,5-trivinylbenzene, 1,2,4-trivinylcyclohexane, 1,3,5-triisopropenylbenzene, 1,4-divinylbenzene, 3-methylhepta-1,5-diene, 3-phenylhexyl These include 1,5-diene, 3-vinylhexa-1,5-diene and 4,5-dimethyl-4,5-diethylocta-1,7-diene, N,N'-methylenebis-acrylamide, 1,1,1-tris(hydroxymethyl)propane triacrylate, 1,1,1-tris(hydroxymethyl)propane trimethacrylate, tripropylene glycol diacrylate, diallyl ether, diallylamine, diallyl carbonate, N,N'-diallylurea, triallylamine, tris(2-methylallyl)amine, 2,4,6-triallyloxy-1,3,5-triazine, triallyl-s-triazine-2,4,6(1H,3H,5H)-trione, diallyl malonate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, and poly(propylene glycol) methacrylate.

[0039] Organopolysiloxane compounds known in the art are suitable for use in component (B) and as the second organopolysiloxane compound. Examples of such organopolysiloxanes include silicone block copolymers having a urea segment, silicone block copolymers having an amide segment and / or an imide segment and / or an ester-amide segment and / or a polystyrene segment and / or a silarylene segment and / or a carborane segment, and silicone graft copolymers having an ether group.

[0040] An organopolysiloxane compound suitable for use as a second organopolysiloxane compound is preferably a linear or branched organopolysiloxane containing units of general formula (II). R 4 a R 5 b SiO (4-a-b) / 2 (II) R 4 In each generation, it is an aliphatic carbon-carbon multiple bond-free group, R 5 In each generation, independently, identically or differently, is a monovalent, substituted or unsubstituted, SiC-bonded hydrocarbon group having at least one aliphatic carbon-carbon multiple bond. a is 0, 1, 2, or 3. b is 0, 1, or 2. However, the sum of a + b is 3 or less, and there are at least two groups R per molecule. 5 It exists.

[0041] R 4 R has the above definition. In some embodiments, R 5 It contains any desired group suitable for addition reactions (hydrosilylation) with SiH-functionalized compounds.

[0042] R 5 If the group contains a SiC bond-substituted hydrocarbon group, preferred substituents are halogen atoms, cyano groups, and -OR 6 And R 6has the above definition.

[0043] Preferably, R 5 is an alkenyl and alkynyl group having 2 to 16 carbon atoms, such as vinyl, allyl, methallyl, 1-propenyl, 5-hexenyl, ethynyl, butadienyl, hexadienyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, vinylcyclohexylethyl, divinylcyclohexylethyl, norbornenyl, vinylphenyl and styryl groups, and vinyl, allyl and hexenyl groups are particularly preferred for use.

[0044] The molecular weight of the second organopolysiloxane compound and any organopolysiloxane compound utilized as part of component (B) can vary within a wide range, for example 10 2 to 10 6 g / mol and so on. Thus, for example, the second organopolysiloxane compound may be a relatively low molecular weight alkenyl-functional oligosiloxane, such as 1,2-divinyltetramethyldisiloxane, or a polydimethylsiloxane having a molecular weight of 10 5 g / mol (number average determined by NMR) with vinyl groups bonded to Si within the chain or at the ends. The structure of the second organopolysiloxane compound can vary between embodiments depending on the desired properties of the composition. Thus, in certain embodiments where the second organopolysiloxane compound has a relatively high molecular mass, in other words an oligomeric or polymeric siloxane, the structure can be linear, cyclic, branched, resinous, network-like or another type of polymer matrix. Linear and cyclic polysiloxanes preferably consist of units of R 4 3SiO 1 / 2 , R 5 R 4 2SiO 1 / 2 , R 5 R 4 SiO 1 / 2 and R<​​​​​​The above definition applies. Branched and reticulated polysiloxanes further comprise trifunctional and / or tetrafunctional units, preferably of formula R 4 SiO 3 / 2 , R 5 SiO 3 / 2 and SiO 4 / 2 Furthermore, as described above, a mixture of these different organopolysiloxanes may be used as component (B).

[0045] Preferably, the second organopolysiloxane compound is a vinyl-functionalized, substantially linear polydiorganosiloxane having a viscosity of 0.01 to 500,000 Pa·s, more preferably 0.1 to 100,000 Pa·s, in which case the viscosity is measured at 25°C.

[0046] In some embodiments, the curable composition may contain 30 to 95% by weight, preferably 30 to 80% by weight, and more preferably 40 to 70% by weight, of the organopolysiloxane compound of component (B). In other embodiments, the curable composition may contain 0.1 to 60% by weight, preferably 0.5 to 50% by weight, and more preferably 1 to 30% by weight, of the organopolysiloxane compound of component (A). If the curable composition includes substitutes for the organopolysiloxanes used in components (A) and (B), such substitute molecules may be present in the curable composition at a concentration of 30 to 95% by weight, preferably 30 to 80% by weight, and more preferably 40 to 70% by weight.

[0047] Preferably, the curable composition is an emulsion. In such embodiments, the curable composition has a continuous phase and a discontinuous phase. In one such embodiment, the continuous phase comprises a polysiloxane network, and the discontinuous phase is dispersed in the continuous phase. The polysiloxane network may be formed by a product of a combination of a first organopolysiloxane compound and a second organopolysiloxane compound. In certain embodiments, the continuous phase may also be formed by utilizing one or more additional organopolysiloxane compounds and / or component (C).

[0048] Component (C) may comprise organopolysiloxane compounds. In some embodiments, the organopolysiloxane compound may have one or more end groups containing a silicon atom bonded to a hydrogen atom. In other embodiments, the organopolysiloxane compound may have one or more end groups containing a carbon-carbon multiple bond. In yet another embodiment, component (C) may comprise a mixture of organopolysiloxanes. For example, in one embodiment, component (C) may comprise an organopolysiloxane compound having one or more end groups containing a silicon atom bonded to a hydrogen atom, an organopolysiloxane compound having one or more end groups containing a carbon-carbon multiple bond, and / or an organopolysiloxane compound that does not contain reactive groups. Component (C) may also comprise reinforcing fillers. In other embodiments, component (C) may comprise non-silicone oligomer compounds, such as polyethers, or copolymers thereof with polymer compounds, such as acrylates, urethanes, polyesters, and siloxanes.

[0049] Alternatively, instead of utilizing different organopolysiloxane compounds, the polysiloxane network may be formed by providing a single organopolysiloxane compound that simultaneously has aliphatic carbon-carbon multiple bonds and Si-bonded hydrogen atoms. In this embodiment, the first organopolysiloxane compound and the second organopolysiloxane compound are chemically identical. However, in this embodiment, the first organopolysiloxane compound and the second organopolysiloxane compound may be provided as parts of separate components.

[0050] When an organopolysiloxane compound has an aliphatic carbon-carbon multiple bond and a Si-bonded hydrogen atom, preferred examples are those composed of units of general formulas (III), (IV), and (V). R 4 f SiO 4 / 2 (III) R 4 g R 5 SiO 3-g / 2 (IV) R 4h HSiO 3-h / 2 (V) R 4 and R 5 The definitions for them are shown above, f is 0, 1, 2, or 3. g is 0, 1, or 2. h is 0, 1, or 2. However, each molecule must have at least two groups R 5 The condition is that at least two Si-bonded hydrogen atoms are present.

[0051] Organopolysiloxane compounds having aliphatic carbon-carbon multiple bonds and Si-bonded hydrogen atoms preferably have an average viscosity of 0.01 to 500,000 Pa·s, more preferably 0.1 to 100,000 Pa·s (in either case at 25°C). Such organopolysiloxanes can be prepared by techniques known in the art.

[0052] The curable composition is preferably cured by crosslinking of the first and second organopolysiloxane compounds. In certain embodiments, the curable composition is formed by addition crosslinking.

[0053] In some embodiments, the curable composition may contain a crosslinking agent. Preferably, the crosslinking agent may be an organopolysiloxane compound. Therefore, in these embodiments, the curable composition may contain a third organopolysiloxane compound. Preferred organopolysiloxane compounds suitable for use as crosslinking agents have one or more groups containing silicon atoms bonded to hydrogen atoms. Preferably, the crosslinking agent comprises an SiH-functional organopolysiloxane compound having an average of at least two SiH groups. In certain embodiments, the crosslinking agent may be a mixture of various SiH-functional organosilicon compounds. Preferably, the crosslinking agent comprises a linear, cyclic, branched, or resinous organopolysiloxane having Si-bonded hydrogen atoms, composed of units of the following formula: R 4 cHdSiO(4-cd) R 4The above definition applies, c is 0, 1, 2, or 3. d is 0, 1, or 2. However, the sum of (c+d) is 3 or less, and on average, there are at least 2 Si-bonded hydrogen atoms per molecule.

[0054] Preferably, the crosslinking agent contains SiH groups in the range of 0.04 to 1.7 weight percent (W%) based on the total weight of the organopolysiloxane used as the crosslinking agent. In these embodiments, the molecular weight of the crosslinking agent can vary over a wide range, for example, between 102 and 106 g / mol. For example, in some embodiments, the crosslinking agent may be a relatively low molecular weight SiH-functional organopolysiloxane compound, such as tetramethyldisiloxane, a high molecular weight polydimethylsiloxane having SiH groups in the chain or terminal positions, or a silicone resin having SiH groups. Low molecular weight organopolysiloxane crosslinking agents include, for example, tetrakis(dimethylsiloxy)silane and tetramethylcyclotetrasiloxane, and SiH-containing organopolysiloxanes, for example, 10 to 1000 mPa·s (25°C, 0.8 sec -1 It is preferable to use poly(hydrogenmethyl)siloxane and poly(dimethylhydrogenmethyl)siloxane having a viscosity in the range of ). Preferably, the crosslinking agent is compatible with the RTV-2 siloxane system (uniformly miscible or at least emulsifiable).

[0055] A hydrosilylation catalyst is provided to crosslink the organopolysiloxane provided in the composition. The hydrosilylation catalyst may be provided as part of one of the above components.

[0056] When a composition is formed by mixing component (A) and component (B), the two components may contain all of the above components in any desired combination, provided that, generally, one component does not simultaneously contain an organopolysiloxane compound having aliphatic multiple bonds, an organopolysiloxane compound having Si-bonded hydrogen atoms, and a hydrosilylation catalyst. Therefore, in the case of a two-component composition, the hydrosilylation catalyst may be provided as part of component (A) or component (B).

[0057] Hydrosilylation catalysts known in this field are suitable for use in curable compositions. Hydrosilylation catalysts may contain platinum group metals, such as platinum, rhodium, ruthenium, palladium, osmium, or iridium, or they may be organometallic compounds or combinations thereof. Suitable examples of hydrosilylation catalysts are compounds such as hexachloroplatinum(IV) acid, platinum dichloride, and platinum acetylacetonate, and complexes of these compounds encapsulated in a matrix or core / shell-like structure. Other suitable platinum complexes having low molecular weight organopolysiloxanes include 1,3-diethenyl-1,1,3,3-tetramethyldisiloxane complexes with platinum. Other examples of suitable hydrosilylation catalysts include platinum-phosphite complexes, platinum-phosphine complexes, or alkylplatinum complexes, such as derivatives of cyclopentadienyltrimethylplatinum(IV) and cyclooctadienyldimethylplatinum(II), or diketonate complexes, such as bisacetylacetonatoplatinum(II). In certain embodiments, the platinum-containing compound may be encapsulated within a resin matrix.

[0058] The concentration of the catalyst for catalyzing the hydrosilylation crosslinking reaction may be 0.1 to 1,000 parts per million (ppm), 0.5 to 100 ppm, or 1 to 25 ppm of platinum group metal, depending on the total weight of the curable composition.

[0059] In the embodiments described above, the composition may be a gel after curing. In these embodiments, the gel has a crosslinked structure. A crosslinked structure can be formed when the total number of reactive groups exceeds four. Therefore, in the gel formed by the platinum-catalyzed hydrosilylation reaction, crosslinking may occur, for example, between a first organopolysiloxane compound containing more than two Si-bonded hydrogen atoms and a second organopolysiloxane compound containing at least two reactive aliphatic unsaturated groups, or alternatively, between a first organopolysiloxane compound containing two Si-bonded hydrogen atoms and a second organopolysiloxane compound having more than two aliphatic unsaturated groups. Preferably, in these embodiments, the first organopolysiloxane compound and the second organopolysiloxane compound are crosslinked to the gelation point of the mixture. In such embodiments, before curing, the curable composition may exhibit a viscosity of 50 to 100,000 centipoise.

[0060] The curable composition contains an organopolysiloxane resin. The curable composition may contain 0.5% by weight or more of the organopolysiloxane resin based on the total weight of the composition. In some embodiments, the curable composition contains 0.5 to 5% by weight of the organopolysiloxane resin based on the total weight of the composition. Preferably, the curable composition contains 1 to 3% by weight of the organopolysiloxane resin based on the total weight of the composition.

[0061] In one embodiment, the organopolysiloxane resin is a vinyl-functionalized MQ resin, or a similar highly crosslinked resin containing M, Q, and / or T moieties and optionally a small amount of D moiety. As used herein, the term “resin” is used in its conventional sense, i.e., a highly three-dimensionally crosslinked polymer containing a majority of M units and T and / or Q units. In certain embodiments, MT, MQ, and MQT resins are preferred. Organopolysiloxane resins containing M and Q units are particularly preferred.

[0062] The term "M" refers to a monofunctional unit, and the term "Q" refers to a tetrafunctional unit. In other words, MQ resins mainly contain M units, where silicon is bonded to only one oxygen atom in the crosslinking molecule, and SiO4,2"Q" units, where each silicon atom is bonded to the other four oxygen atoms, resulting in a high level of crosslinking. In some embodiments, MQ resins contain small amounts of bifunctional R2SiO 2 / 2 Unit and trifunctional RSiO 3 / 2 The MQ resin may contain units ("D" and "T" units, respectively). MQ resins suitable for use in curable compositions can be produced by hydrolysis of silanes such as tetraethoxysilane, vinyldimethylethoxysilane, and trimethylethoxysilane. In some embodiments, the MQ resin may retain some residual alkoxy functional groups as a result of its preparation method, and may also contain other functional groups such as silanol or halo functional groups. Preferably, the MQ resin contains about 1.2 to 1.8 weight percent vinyl functionality. Alternatively, MQ resins having unsaturated groups other than vinyl, such as vinyloxy, allyl, allyloxy, and propenyl, may be used.

[0063] In certain embodiments, MQ resins formed as co-hydrolysis products of tetraalkoxysilane and trimethylalkoxysilane may be suitable. Such MQ resins may contain a three-dimensional network of polysilicic acid units having trimethylsilyl-terminated groups. The average molecular weight of such MQ resins can be controlled by the ratio of M units to Q units in the resin. Preferably, the ratio of M units to Q units is 0.5 to 1, with a ratio of about 0.67 being preferred.

[0064] The embodiments of the MQ resins described above may be used individually, in combination with each other, or in combination with other unsaturated resins. Preferred commercially available MQ resins include MQ resin 804 and MQ resin 803, both of which are available from Wacker Chemical Corporation.

[0065] Organopolysiloxane resins may contain a variety of unsaturated groups for the hydrosilylation reaction, including both ethylenically and unsaturated groups, as shown. While not essential, it is preferable that the unsaturation is at a terminal position. For example, if a hexenyl unsaturated group is present, a terminal (co)hexenyl group is preferred. The unsaturated group may also be an unsaturated ether group, such as a vinyl ether group, as shown, or another heteroatom-containing group, namely a (meth)acryloxy group. Vinyl and allyl groups are most preferred.

[0066] Before curing, the curable composition is an emulsion containing a continuous phase and a discontinuous phase. The presence of the organopolysiloxane resin reduces the interfacial tension between the continuous and discontinuous phases of the curable composition. As used herein, the term interfacial tension refers to a measure of work per unit area or force per wet length, which can be determined according to the Wilhelmie plate method. The interfacial tension values ​​referred to herein are measured at the liquid / liquid interface between the continuous and discontinuous phases of the curable composition.

[0067] While we do not wish to be bound by any particular theory, it is thought that the interaction between hydrophilic compounds and organopolysiloxane compounds in a curable composition separates the continuous and discontinuous phases into at least two visually distinct layers. However, the decrease in interfacial tension between the continuous and discontinuous phases due to the use of organopolysiloxane resins in a curable composition increases the compatibility of these phases. This increased compatibility eliminates observable phase separation in the curable composition if all of its components are mixed together so that the composition appears to be a homogeneous mixture before curing.

[0068] Therefore, by including organopolysiloxane resin, compositions exhibiting lower interfacial tensions than those shown in known compositions can be obtained. In fact, in some embodiments of the curable composition, the interfacial tension between the continuous and discontinuous phases is 28 mN / m or less. In other embodiments, the interfacial tension between the continuous and discontinuous phases of the curable composition is 22 to 28 mN / m. More preferably, the interfacial tension between the continuous and discontinuous phases of the curable composition is 24 to 28 mN / m. Interfacial tension can be measured using a commercially available interfacial tension meter. An example of a suitable commercially available instrument is the K100 tension meter available from KRUESS Scientific Instruments, Inc.

[0069] Furthermore, in curable compositions, phase compatibility can be rapidly established by mixing with commercially available mixing equipment and standard mixing methods. Compatibility between continuous and discontinuous phases can also be maintained for commercially significant periods, allowing the curable composition to be transported and applied to a substrate before curing. For example, in certain embodiments, the curable composition shows no observable phase separation for at least 24 hours at 23°C and 55% relative humidity, or after centrifugation at 23°C and 5000 rpm for 5 minutes. Preferably, the curable composition shows no observable phase separation after 90 days at 23°C and 55% relative humidity, or after centrifugation at 23°C and 5000 rpm for 5 minutes. In certain embodiments, the curable composition may show no observable phase separation after 9 months at 23°C and 55% relative humidity after centrifugation for 5 minutes. It should be noted that the curable composition can be formed by mixing for less than 5 minutes or more than 5 minutes, for example, 3 minutes or more than 40 minutes, and that prolonged mixing, such as centrifugation, does not substantially affect the stability of the curable composition or increase the likelihood of phase separation being observed. The absence of observable phase separation for a commercially significant period of time makes it possible to use the curable composition in conventional wound care bandages and to form a homogeneous gel-like adhesive layer after application to a desired substrate and curing.

[0070] The effect of improving the interfacial tension by adding organopolysiloxane compounds, hydrophilic compounds, and other components of a curable composition to an organopolysiloxane resin can be seen in the example shown in Figure 1. In the example shown in Figure 1, the continuous phase contains an organopolysiloxane compound, and the discontinuous phase contains a hydrophilic compound. More specifically, in the example shown in Figure 1, the organopolysiloxane compound is an organopolysiloxane having one or more groups containing carbon-carbon multiple bonds, particularly WACKER VIPO 1000 polymer, and the hydrophilic compound was glycerol. As shown in Figure 1, in the absence of the organopolysiloxane resin, the interfacial tension between the continuous and discontinuous phases is greater than 28 mN / m. Also, as shown in Figure 1, by adding the organopolysiloxane resin, the interfacial tension between the continuous and discontinuous phases decreases to 28 mN / m or less over the entire range shown.

[0071] The curable composition contains a silver-containing antimicrobial agent. In certain embodiments, the silver-containing antimicrobial agent is a silver salt having antimicrobial properties. The silver-containing antimicrobial agent can be selected from the group including Ag2SO4, Ag2SO3, AgNO3, Ag2CO3, Ag3PO4, silver zirconium, and / or organic silver salts, such as silver citrate, silver acetate, silver lactate, and / or combinations or mixtures thereof. Other compounds suitable for providing silver ions if desired are also suitable as silver-containing antimicrobial agents. The silver-containing antimicrobial agent may be provided in the curable composition in all cases at about 1 wt% to about 30 wt%, preferably about 2 to 20 wt%, based on the total weight of the composition. The silver-containing antimicrobial agent may be provided as part of component (A), component (B), component (C), as two or more of these components, or as a separate additive to the composition.

[0072] The curable composition may contain an excipient. If an excipient is provided, the excipient inhibits the formation of elemental silver or silver oxide by the silver-containing antimicrobial agent to the extent that the curable composition does not show an observable color change after exposure to air at 50% relative humidity at 25°C for 24 hours.

[0073] The curable composition may contain 0.5% by weight or more of excipients based on the total weight of the composition. Preferably, the curable composition contains 0.5 to 15% by weight of excipients based on the total weight of the composition, if provided. More preferably, the curable composition contains 0.5 to 10% by weight of excipients based on the total weight of the composition. The excipients may be provided as part of component (A), component (B), component (C), or as two or more of these components.

[0074] Preferably, if provided, the weight percentage of the excipient in the curable composition is greater than the weight percentage of the silver-containing antimicrobial agent in the curable composition, based on the total weight of the composition. For example, the weight percentage of the excipient present in the curable composition may be more than twice as great than the weight percentage of the silver-containing antimicrobial agent. In one embodiment, the weight percentage of the excipient present in the curable composition is more than 2 to 10 times greater than the weight percentage of the silver-containing antimicrobial agent.

[0075] In some embodiments, the excipient is an alcohol containing one or more hydroxyl groups. In other embodiments, the excipient may be a glycol. In these embodiments, the excipient has two or more hydroxyl groups, and two of the two or more hydroxyl groups may be bonded to different carbon atoms. In one such embodiment, two of the two or more hydroxyl groups are terminal groups. In some embodiments, the excipient is a polyether.

[0076] In one embodiment, the excipient has a number average molecular weight of 100 g / mol or more. In another embodiment, the excipient may have a number average molecular weight of 300 g / mol or more. Preferably, the excipient has a relatively low number average molecular weight. In one such embodiment, the excipient has a number average molecular weight of 300 to 2,000 g / mol. In yet another embodiment, the number average molecular weight of the excipient is 300 to 1,000 g / mol. Preferably, in these embodiments, the number average molecular weight of the excipient is 300 to 600 g / mol.

[0077] In some embodiments, the excipient may be selected from the group consisting of poly(propylene glycol), 1,2-propanediol, di(propylene glycol), di(propylene glycol) monomethyl ether, di(propylene glycol) dimethyl ether, organopolysiloxane polyoxyalkylene, copolymers, and mixtures thereof, with a number average molecular weight of 400 to 2000 g / mol. In certain embodiments, the excipient may preferably be poly(propylene glycol) with a number average molecular weight of 400 to 2000 g / mol. Preferably, in these embodiments, the excipient is poly(propylene glycol) with a number average molecular weight of 400 g / mol. In other embodiments, the excipient may preferably be organopolysiloxane polyoxyalkylene. Preferably, in these embodiments, the excipient is organopolysiloxane polyoxyalkylene with the following general formula.

[0078] [ka]

[0079] In certain embodiments, the organopolysiloxane polyoxyalkylene may be covalently bonded. An example of a commercially available organopolysiloxane polyoxyalkylene suitable as an excipient is sold by Wacker Chemie AG under the name Belsil(R)OW 1500. As described above, the curable composition has a discontinuous phase. If an excipient is provided, the excipient is present in the discontinuous phase.

[0080] The curable composition may contain one or more additives that may be provided as part of component (A), component (B), or component (C). For example, as described above, the antimicrobial composition may contain a reinforcing filler. A suitable reinforcing filler contains at least 50 m 2The silica fillers include fumed or precipitated silica, carbon black, activated carbon, such as furnace black and acetylene black, or mixtures thereof, having a BET specific surface area of ​​1 / g. The silica fillers described may be hydrophilic or hydrophobic by known methods. The amount of reinforcing filler in the curable composition may be in the range of 0 to 70% by weight, preferably 0 to 50% by weight, based on the total weight of the curable composition.

[0081] In certain embodiments, the filler used is preferably surface-treated. The surface treatment is obtained by methods known in the art for hydrophobizing the finely divided filler. As a result of the surface treatment, the carbon content of the filler used may be at least 0.01 to a maximum of 20% by weight, preferably 0.1 to 10% by weight, and more preferably 0.5 to 5% by weight. Preferably, in these embodiments, the filler is surface-treated silica having 0.01 to 2% by weight of Si-bonded aliphatic unsaturated groups. These groups are, for example, Si-bonded vinyl groups. In the curable composition, the filler is provided as a single species or as a mixture of two or more finely divided fillers.

[0082] Further additives may be provided in the curable composition in a proportion of up to 70% by weight, preferably 0.0001 to 40% by weight, based on the total weight of the composition. These additives may include, for example, inert fillers, resinous polyorganosiloxanes different from the siloxanes described above, reinforcing and unreinforcing fillers, antifungal agents, fragrances, rheological additives, corrosion inhibitors, antioxidants, light stabilizers, flame retardants and agents affecting electrical properties, dispersing aids, solvents, adhesion promoters, pigments, dyes, plasticizers, organic polymers, and heat stabilizers. These include additives such as finely ground quartz, diatomaceous earth, clay, chalk, lithopone, carbon black, graphite, metal oxides, metal carbonates, metal sulfates, metal salts of carboxylic acids, metal powders, fibers such as glass fibers, polymer fibers, polymer powders, metal powders, dyes, and pigments. Additional fillers may be thermally or electrically conductive. Combinations of fillers having different particle sizes and different particle size distributions may also be available.

[0083] Furthermore, the curable composition may contain additional additives, such as one or more solvents and / or one or more inhibitors. For example, in some embodiments, the curable composition may contain a hydrosilylation inhibitor. Such inhibitors enable the curable composition to exhibit a predetermined work life, curing onset temperature, and curing rate. Examples of suitable inhibitors include acetylene alcohols, e.g., 1-ethynyl-1-cyclohexanol, 2-methyl-3-butyne-2-ol and 3,5-dimethyl-1-hexyne-3-ol, 3-methyl-1-dodecine-3-ol, polymethylvinylcyclosiloxanes, e.g., 1,3,5,7-tetravinyltetramethyltetracyclosiloxane, methylvinyl-SiO 1 / 2 R2 vinylSiO 1 / 2 Low molecular weight silicone oils having terminal groups, such as divinyltetramethyldisiloxane, tetravinyldimethyldisiloxane, trialkylcyanurates, alkyl maleates, such as diallyl maleate, dimethyl maleate, and diethyl maleate, alkyl fumarates, such as diallyl fumarate and diethyl fumarate, organic hydroperoxides, such as cumene hydroperoxide, tert-butyl hydroperoxide, and pinan hydroperoxide, organic peroxides, organic sulfoxides, organic amines, diamines, and amides, phosphans and phosphites, nitriles, triazoles, diaziridines, and oximes. In certain embodiments, the hydrosilylation inhibitor is provided in the curable composition in a quantitative proportion of 0.00001 to 5% by weight, based on the total weight of the curable composition. Preferably, the hydrosilylation inhibitor is provided in the curable composition in an amount of 0.00005 to 2% by weight, more preferably 0.0001 to 1% by weight, in either case based on the total weight of the composition.

[0084] The curable composition contains a hydrophilic compound. The hydrophilic compound is provided to enhance silver release from the composition. In these embodiments, the silver-containing antimicrobial agent and the hydrophilic compound are present in a discontinuous phase. Preferably, the hydrophilic compound is a polyol. Preferred polyols include polyhydric alcohols or polyethers. Examples of polyhydric alcohols suitable for use in the curable composition may be selected from the group consisting of sorbitol and mannitol. Examples of polyethers suitable for use in the curable composition may be selected from the group consisting of polyethylene glycol and polypropylene glycol. A preferred polyol is glycerol. In certain embodiments, the hydrophilic compound is present in the composition in all cases at a concentration of 3 to 40% by weight, preferably about 3 to 30% by weight, based on the total weight of the composition.

[0085] The hydrophilic compounds described above, when cured as a gel, can swell the curable composition by at least 5% after 24 hours in an aqueous solution containing 8.298 g / L sodium chloride and 0.368 g / L calcium chloride dihydrate, as measured by the free swelling absorption method. The advantage of this swelling performance is the antimicrobial effect exhibited when using silver-containing antimicrobial agents, which can be achieved without using high concentrations of silver-containing antimicrobial agents in the gel.

[0086] As described above, after curing, the curable composition can function as an adhesive as a gel. In these embodiments, the adhesive can be used as the adhesive portion of a wound care bandage. Advantageously, the composition can function as an adhesive when gelled because, despite the presence of hydrophilic components, the exhibited tackiness is sufficiently high, typically resulting in phase separation due to the density difference between the hydrophilic components and the organopolysiloxane compound. For example, in certain embodiments, the tackiness exhibited by the gel may be greater than 50 grams of force (gf). Preferably, the tackiness exhibited by the gel is greater than 100 gf. However, the tackiness should not be so strong that it damages the user's skin when removing the bandage. Therefore, in some embodiments, the tackiness exhibited by the gel is less than 800 gf. In these embodiments, the tackiness exhibited by the gel may be between 50 and 800 gf. The tackiness exhibited by the gel can be measured by known methods. For example, the tackiness of the gel can be measured using a TA.XT Plus texture analyzer with a TA-57R probe and a TA-303 instrument.

[0087] In addition to adequate tackiness, the gel is preferably cohesive. A cohesive gel does not crumble or leave a noticeable visible residue when removed from the surface to which it is attached. In some embodiments, the gel may exhibit a post-curing penetration hardness of 25 to 500 1 / 10 mm, measured according to DIN ISO 2137 using a 62.5 gram hollow cone for 60 seconds after curing at 120°C for 60 minutes.

[0088] As described above, the curable composition can form a gel after being applied to a substrate. In some embodiments, the curable composition can coat a substrate, such as a bandage. In these embodiments, the curable composition can be cast onto the substrate and cured to form a gel. The curable composition can be applied to a substrate to provide any desired thickness, pattern, or shape. Suitable substrates are known in the art.

[0089] Before forming the gel, the curable composition can be prepared by preparing component (A). Preferably, component (A) contains the organopolysiloxane described above for component (A). Furthermore, component (A) may also contain a silver-containing antimicrobial agent, an excipient, a hydrosilylation catalyst, an organopolysiloxane resin, a hydrophilic compound and / or one or more additional additives. If included in component (A), the silver-containing antimicrobial agent, the excipient, the hydrosilylation catalyst, the organopolysiloxane resin, the hydrophilic compound and one or more additional additives can be mixed with the organopolysiloxane to form a mixture. Mixing can be carried out at a predetermined rate and over a predetermined period of time using a commercially available mixing device, such as a Speedmixer(R) or a Dispermat(R) equipped with dissolving blades. The silver-containing antimicrobial agent, the excipient, the hydrosilylation catalyst, the hydrophilic compound and one or more additional additives may be as described above.

[0090] In certain embodiments, a curable composition may be prepared by preparing component (B). Preferably, component (B) comprises the organopolysiloxane described above for component (B). Furthermore, component (B) may also comprise a silver-containing antimicrobial agent, an excipient, a hydrosilylation catalyst, an organopolysiloxane resin, a hydrophilic compound, and / or one or more additional additives. If included in component (B), the silver-containing antimicrobial agent, the excipient, the hydrosilylation catalyst, the organopolysiloxane resin, the hydrophilic compound, and one or more additional additives may be mixed with the organopolysiloxane to form a mixture. Mixing can be carried out at a predetermined rate and over a predetermined period of time using a commercially available mixing apparatus, such as the mixing apparatus described above. The silver-containing antimicrobial agent, the excipient, the hydrosilylation catalyst, the organopolysiloxane resin, the hydrophilic compound, and one or more additional additives may be as described above.

[0091] In embodiments in which the curable composition contains component (C), the curable composition is prepared by preparing component (C). In these embodiments, the curable composition may be prepared by preparing three mixtures and combining them. Preferably, component (C) contains an organopolysiloxane as described above for component (C). Furthermore, component (C) may also contain a silver-containing antimicrobial agent, an excipient, a hydrosilylation catalyst, a hydrophilic compound and / or one or more additional additives. If included in component (C), the silver-containing antimicrobial agent, the excipient, the hydrosilylation catalyst, the hydrophilic compound and one or more additional additives may be mixed with the organopolysiloxane to form a mixture. Thus, in these embodiments, the curable composition may be prepared by first preparing three mixtures. Mixing can be carried out at a predetermined rate over a predetermined period of time using a commercially available mixing apparatus as described above. The silver-containing antimicrobial agent, the excipient, the hydrosilylation catalyst, the hydrophilic compound and one or more additional additives may be as described above.

[0092] In certain embodiments, component (A) and component (B) may be mixed to form a mixture before coating the substrate. Mixing can be performed at a predetermined rate and over a predetermined period of time using a commercially available mixing apparatus, such as the mixing apparatus described above. In some embodiments, the mixture may also contain component (C). If not included in component (A), (B), or (C), or if it is desirable to include additional amounts in the curable composition, silver-containing antimicrobial agents, excipients, hydrosilylation catalysts, organopolysiloxane resins, hydrophilic compounds, and / or one or more additional additives can be added to the mixture. The addition of one or more of these components can be achieved when mixing components (A), (B), and (C), or can be done simultaneously or sequentially by further mixing. After mixing, one or more portions of the substrate can be coated with the curable composition, and the composition can be cured at a predetermined temperature for a predetermined period of time. For example, the mixture can be cured at a temperature of 40 to 140°C, preferably 60 to 130°C, for 5 seconds to 2 hours, preferably 10 seconds to 30 minutes.

[0093] In certain embodiments, component (A) is prepared to comprise an organopolysiloxane having one or more groups containing a silicon atom bonded to a hydrogen atom. In this embodiment, the curable composition is produced by mixing the organopolysiloxane having one or more groups containing a silicon atom bonded to a hydrogen atom with a silver-containing antimicrobial agent, a hydrophilic component, and an organopolysiloxane resin. Preferably, the hydrophilic compound is a polyol as described above. In one embodiment, component (B) is prepared to comprise an organopolysiloxane having one or more terminal groups containing a carbon-carbon multiple bond. Preferably, component (B) also comprises one or more additives, such as reinforcing fillers. However, in certain embodiments, component (B) may preferably be formed by mixing the organopolysiloxane having one or more terminal groups containing a carbon-carbon multiple bond with a silver-containing antimicrobial agent. In these embodiments, component (A) may not contain the silver-containing antimicrobial agent. The curable composition is preferably formed by forming a mixture. In certain embodiments, the mixture comprises component (A), component (B), a hydrosilylation catalyst, and optionally a hydrosilylation inhibitor. The mixture is cured to form an antimicrobial gel. [Examples]

[0094] The following examples are provided solely for the purpose of further illustrating and disclosing embodiments of the curable composition. Examples of curable compositions include Examples 1 to 7, which will be described later. Comparative examples that are not part of the present invention are also described below.

[0095] [Comparative Example 1] The composition was formed by mixing 5 grams of WACKER VIPO 1000 polymer, which contained an organopolysiloxane having two end groups, each end group containing a carbon-carbon multiple bond. The organopolysiloxane had a molecular weight of approximately 16,000 g / mol (viscosity of approximately 1,000 cSt). The composition also contained 1.15 grams of WACKER H polymer 1000 (molecular weight of approximately 16,000 g / mol (approximately 1,000 cSt.) and an organopolysiloxane having one or more groups containing silicon atoms bonded to hydrogen atoms), 0.05 grams of WACKER H018 crosslinking agent (a hydrogen organosiloxane crosslinking agent having at least three groups containing silicon atoms bonded to hydrogen atoms), and 0.5 grams of glycerol. The components were mixed using a SpeedMixer(R) at 2350 rpm for 5 minutes at 23°C and 55% relative humidity. The resulting composition was fluid and showed observable phase separation immediately after mixing. Before mixing all components together, interfacial tension (IFT) measurements were performed at the glycerol-siloxane interface. The measurements were performed using a K100 tensile strength meter. The IFT measurement was approximately 30 mN / m.

[0096] [Comparative Example 2] A composition was prepared by mixing 5 grams of WACKER H Polymer 1000 and 0.5 grams of glycerol additive using a SpeedMixer(R) at 2350 rpm for 5 minutes at 23°C and 55% relative humidity. The composition showed observable phase separation immediately after mixing at 23°C and 55% relative humidity, or after centrifugation at 23°C and 5000 rpm for 3 minutes. Before mixing all components together, IFT measurements were performed at the glycerol-siloxane interface using a K100 force meter. The IFT measurement was approximately 30 mN / m.

[0097] [Comparative Example 3] A composition was prepared by mixing 5 grams of WACKER VIPO 1000 polymer and 0.5 grams of glycerol using a SpeedMixer(R) at 2350 rpm for 5 minutes at 23°C and 55% relative humidity. The composition showed observable phase separation immediately after mixing. Before mixing all components together, IFT measurements were performed at the glycerol-siloxane interface using a K100 force meter. The IFT measurement was approximately 30 mN / m.

[0098] [Example 1] A composition was formed by mixing component (A) and component (B). Component (A) contained 1.15 grams of WACKER H polymer 1000, and 5 grams of WACKER VIPO 1000 polymer were added after mixing the components described later to form the composition. Component (B) contained 5 grams of WACKER VIPO 1000 polymer, 0.1 grams of WACKER MQ804 resin (a co-hydrolysis product of tetraalkoxysilane (Q units) and trimethylalkoxysilane (M units), containing carbon-carbon multiple bonds and some residual ethoxy and hydroxyl functional groups), and 0.1 to 500 ppm by weight of a platinum-containing hydrosilylation catalyst (based on the platinum content of the vinyl platinum-containing hydrosilylation catalyst relative to the total adhesive formulation). The composition also contained 1% by weight of an inhibitor known as PT 730 VS WACKER based on the total weight of the composition, which is divinyldimethylsiloxane. The composition also contained 0.5 grams of a mixture of silver sulfate and calcined silica. Based on the total weight of the mixture, the silver sulfate and calcined silica mixture consisted of 99% silver sulfate and 1% calcined silica. The composition also contained 0.5 grams of glycerol.

[0099] To form the composition, all components were mixed together for 5 minutes at 23°C and 55% relative humidity using a SpeedMixer(R) at 2350 rpm. After mixing, an emulsion with a continuous phase and a discontinuous phase was formed. The composition did not show observable phase separation at 23°C and 55% relative humidity, or after centrifugation at 23°C and 5000 rpm for 3 minutes. Furthermore, the composition was stored and monitored at 23°C and 55% relative humidity for 3 months, and no observable phase separation was observed during this period.

[0100] Before mixing all other components of the composition together, an IFT (Integrated Filtration Test) was performed at the glycerol-siloxane interface on a mixture containing 5 grams of VIPO 1000, 0.1 grams of WACKER MQ804 resin, and 0.5 grams of glycerol. The IFT was performed on a mixture containing only the three components mentioned above, as it is understood by those skilled in the art that the addition of other components of the composition does not significantly affect the IFT in the glycerol-siloxane interface composition. The IFT was performed using a K100 force tensile strength meter and yielded a value of 25.2 mN / m.

[0101] [Example 2] A composition was formed by mixing component (A) and component (B). Component (A) contained 1.15 grams of WACKER H polymer 1000, 0.05 grams of WACKER H018 crosslinking agent (an organosiloxane crosslinking agent having at least three groups containing silicon atoms bonded to hydrogen atoms), and 5 grams of WACKER VIPO 1000 polymer.

[0102] Component (B) consisted of 5 grams of WACKER VIPO 1000 polymer, 0.1 grams of WACKER MQ804 resin, and 0.1 to 500 ppm by weight of a platinum-containing hydrosilylation catalyst. The formulation also contained 1% by weight of an inhibitor known as PT 730 VS WACKER based on the total weight of the composition.

[0103] The composition also contained 0.5 grams of a mixture of silver sulfate and calcined silica. Based on the total weight of the mixture, the silver sulfate and calcined silica mixture consisted of 99% silver sulfate and 1% calcined silica. The composition also contained 0.5 grams of glycerol.

[0104] To form the composition, the components were mixed using a SpeedMixer(R) at 2350 rpm for 5 minutes at 23°C and 55% relative humidity. After mixing, an emulsion having a continuous phase and a discontinuous phase was formed. The composition did not show observable phase separation at 23°C and 55% relative humidity, or after centrifugation at 23°C and 5000 rpm for 3 minutes. Furthermore, the composition was stored and monitored at 23°C and 55% relative humidity for 3 months, and no observable phase separation was observed during this period.

[0105] Before mixing all the components of the composition, an IFT (Intensity-Focused Tension) measurement of component (B) was performed at the glycerol-siloxane interface using a K100 tensile strength meter. Those skilled in the art will understand that the IFT of component (B) at the glycerol-siloxane interface is substantially the same as that of the composition. The measured IFT value was 25.2 mN / m.

[0106] [Example 3] 5 grams of WACKER VIPO 1000 polymer, 0.05 grams of WACKER MQ804 resin, and 0.5 grams of glycerol were mixed using a SpeedMixer(R) at 2350 rpm for 5 minutes. The mixture did not show observable phase separation immediately after mixing or after centrifugation at 23°C and 55% relative humidity for 3 minutes. After mixing with the MQ804 resin, IFT measurements were performed at the glycerol-VIPO 1000 interface using a K100 tensile strength meter. The IFT measurement was 25.5 mN / m. This example demonstrates that the presence or absence of a silver-containing antimicrobial agent does not significantly affect the interfacial tension of the curable composition.

[0107] [Example 4] Compositions (A) and (B) were mixed to form a new composition. Component (A) contained a mixture of 1.15 grams of WACKER H polymer 1000 and 0.05 grams of WACKER H018 crosslinking agent. Component (B) contained a mixture of 5 grams of WACKER VIPO 1000 polymer, 0.5 grams of glycerol, and a 2 wt% load of WACKER MQ804 organopolysiloxane resin based on the total mass of the composition. Before mixing the components together, IFT measurements were performed at the glycerol-VIPO 1000 interface using a K100 force meter. The IFT measurement was 25.5.0 mN / m.

[0108] The compositions were formed by mixing the composition of component (A) and the composition of component (B) for 5 minutes using a SpeedMixer(R) at 2350 rpm for 30 seconds. The mixture did not show any observable phase separation immediately after mixing at 23°C and 55% relative humidity, nor after centrifugation at 23°C and 5000 rpm for 3 minutes.

[0109] [Example 5] A composition was formed by mixing component (A) and component (B). Component (A) contained a mixture of 1.15 grams of WACKER H polymer 1000 and 0.05 grams of WACKER H018 crosslinking agent. Component (B) contained a mixture of 5 grams of WACKER VIPO 1000 polymer, 0.5 grams of glycerol, and 3 wt% of WACKER MQ804 organopolysiloxane resin based on the total mass of the composition. Before mixing the components together, an IFT measurement was performed at the glycerol-VIPO 1000 interface using a K100 force meter. The IFT measurement was 25.8 mN / m.

[0110] The composition was formed by mixing component (A) and component (B) for 5 minutes using a SpeedMixer(R) at 2350 rpm for 30 seconds. The mixture did not show observable phase separation immediately after mixing at 23°C and 55% relative humidity, nor after centrifugation at 23°C and 5000 rpm for 3 minutes.

[0111] [Example 6] A composition was formed by mixing component (A) and component (B). Component (A) contained a mixture of 1.15 grams of WACKER H polymer 1000 and 0.05 grams of WACKER H018 crosslinking agent. Component (B) contained a mixture of 5 grams of WACKER VIPO 1000 polymer, 0.5 grams of glycerol, and WACKER MQ804 organopolysiloxane resin at a concentration of 4% by weight relative to the total mass of the composition. Before mixing the components together, an IFT measurement was performed at the glycerol-VIPO 1000 interface using a K100 force meter. The IFT measurement was 25.6 mN / m.

[0112] The composition was formed by mixing component (A) and component (B) for 5 minutes using a SpeedMixer(R) at 2350 rpm for 30 seconds. The mixture did not show observable phase separation immediately after mixing at 23°C and 55% relative humidity, nor after centrifugation at 23°C and 5000 rpm for 3 minutes.

[0113] [Example 7] A composition was formed by mixing component (A) and component (B). Component (A) contained a mixture of 1.15 grams of WACKER H polymer 1000 and 0.05 grams of WACKER H018 crosslinking agent. Component (B) contained a mixture of 5 grams of WACKER VIPO 1000 polymer, 0.5 grams of glycerol, and WACKER MQ804 organopolysiloxane resin at a concentration of 5% by weight relative to the total mass of the composition. Before mixing the components, IFT measurements were performed at the glycerol-VIPO 1000 interface using a K100 force meter. The IFT measurement was 25.2 mN / m.

[0114] The compositions were prepared by mixing component (A) and component (B) for 5 minutes using a SpeedMixer(R) at 2350 rpm for 30 seconds. The mixture did not show any observable phase separation immediately after mixing at 23°C and 55% relative humidity, nor after centrifugation at 23°C and 5000 rpm for 3 minutes.

[0115] From the detailed description above, it is clear that various modifications, additions, and other alternative embodiments are possible without departing from the true scope and spirit. The embodiments and examples discussed herein have been selected and described to enable those skilled in the art to use the invention in various embodiments, with various modifications suitable for the specific use intended, by providing best examples of the principles and practical applications of the invention. As will be understood, all such modifications and variations are within the scope of the invention.

Claims

1. A curable composition, A first organopolysiloxane compound having one or more groups containing a silicon atom bonded to a hydrogen atom, A second organopolysiloxane compound having one or more groups containing carbon-carbon multiple bonds, Hydrosilylation catalyst and Organopolysiloxane resin and Silver-containing antibacterial agent, Hydrophilic compounds and Includes, A curable composition in which the composition is an emulsion having a continuous phase and a discontinuous phase.

2. The composition according to claim 1, wherein the composition contains 0.5% by weight or more of organopolysiloxane resin based on the total weight of the composition.

3. The composition according to claim 1, wherein the organopolysiloxane resin comprises M units and Q units.

4. The composition according to claim 1, wherein the curable composition does not exhibit observable phase separation after being centrifuged at 23°C and 55% relative humidity for at least 24 hours, or at 23°C and 5000 rpm for 5 minutes.

5. The composition according to claim 1, wherein the interfacial tension between the continuous phase and the discontinuous phase is less than 28 mN / m.

6. The composition according to claim 1, wherein the silver-containing antibacterial agent is a silver salt.

7. The composition according to claim 1, wherein the hydrophilic compound is a polyol.

8. The composition according to claim 1, wherein the curable composition has a continuous phase containing a polysiloxane network.

9. The composition according to claim 1, further comprising a hydrosilylation inhibitor.

10. The composition according to claim 1, wherein the antibacterial agent and the hydrophilic compound are present in a discontinuous phase.

11. The composition according to claim 2, wherein the composition comprises 0.5 to 5% by weight of an organopolysiloxane resin based on the total weight of the composition.

12. The composition according to claim 4, wherein the curable composition does not show observable phase separation after 90 days at 23°C and 55% relative humidity, or after centrifugation at 23°C and 5000 rpm for 5 minutes.

13. The composition according to claim 5, wherein the interfacial tension between the continuous phase and the discontinuous phase is 22 to 28 mN / m.

14. The composition according to claim 7, wherein the polyol is glycerol.

15. The composition according to claim 7, wherein the hydrophilic compound is a polyhydric alcohol or a polyether.

16. A method for forming a gel-like adhesive, The steps of applying the composition described in claim 1 to a substrate, A step of curing the composition, Methods that include...

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