Hydrophilic modified silicone pressure-sensitive adhesive

Abstract

This application describes and presents compositions for forming novel hydrophilically modified silicones and hydrophilically modified silicone pressure-sensitive adhesives. These compositions comprise (i) MQ silicone resin, (ii) polyorganosiloxane, and (iii) siloxane containing a predetermined hydrophilic functional group. The mixture of (i), (ii), and (iii) is autocatalytic and does not require an external condensation catalyst. These compositions are suitable for forming cured silicone materials, such as pressure-sensitive adhesives compatible with polar additives or active substances used in various applications.

Description

[Technical Field]

[0001] The present invention relates to a siloxane containing a hydrophilic group, and a silicone composition containing the siloxane suitable for forming a silicone pressure-sensitive adhesive. In particular, the present invention relates to a composition that may be considered self-catalytic, and a pressure-sensitive adhesive material formed from such a composition. [Background technology]

[0002] Silicone pressure-sensitive adhesives can be used in a variety of applications. One area where silicone pressure-sensitive adhesives have found many advantages is in personal care and healthcare applications. These can include, but are not limited to, many different types of products, such as tapes, dressings, wearable devices, and others. In these applications, pressure-sensitive adhesives often come into direct contact with the skin of the person wearing the product or device. Compared to non-silicone pressure-sensitive adhesives, silicone pressure-sensitive adhesives and gels can provide improved comfort during wear and can be removed without causing damage.

[0003] While silicone pressure-sensitive adhesives offer advantages in terms of comfort, they are also hydrophobic. A high degree of hydrophobicity can limit the use of adhesives in personal care and healthcare applications. For example, high hydrophobicity may restrict the compatibility of the adhesive with components used in personal care and healthcare applications. Several conventional attempts to overcome this problem have involved using non-silicone polar materials as adhesives. Another option is to use additives that impart polar or hydrophilic properties to silicone adhesives. However, non-reactive additives are extractable or migrate, potentially altering the composition and properties of the adhesive over time. Furthermore, the use of additives to impart hydrophilicity, and especially the amount of additives that can be used, is limited to amounts that can be miscible in the composition. [Overview of the Initiative]

[0004] The following is an overview of the present disclosure, providing a basic understanding of some aspects. This overview is not intended to identify important or essential elements, nor to define any limitations on the embodiments or claims. Furthermore, this overview may present a simplified summary of some embodiments, which may be described in detail elsewhere in the present disclosure.

[0005] Provided are silicone compositions and materials formed from such compositions. The silicone compositions may be suitable for producing silicone pressure-sensitive adhesives. According to aspects of the present invention, the silicone compositions include a silicone resin, a polyorganosiloxane, and a siloxane containing a hydrophilic group selected from ionic groups and / or zwitterionic groups. The hydrophilic functional group silicone material can be selected from a silicone resin (e.g., an MQ-type resin) and / or a polyorganosiloxane functionalized with a hydrophilic group.

[0006] The silicone compositions are suitable for producing silicone materials such as, for example, silicone pressure-sensitive adhesives, which have improved hydrophilicity compared to other silicone pressure-sensitive adhesives while retaining the desired adhesive properties. In particular, the compositions of the present invention provide a silicone adhesive composition comprising a silicone having covalently bonded hydrophilic groups. These groups may also be considered polar functional groups. It has been found that a siloxane containing a hydrophilic group improves the hydrophilicity of a silicone adhesive that would be hydrophobic if it did not contain this group.

[0007] In one embodiment, a siloxane containing a hydrophilic group is provided, which has the following formula: M 1 a M 2 b M 3 c D 1 d D 2e D 3 f T 1 g T 2 h T 3 i Q 1 j Q 2 k Q 3 l Q 4 o Q 5 p Here we go M 1 =R 5 R 6 R 7 SiO 1 / 2 M 2 =R 8 R 9 R 10 SiO 1 / 2 M 3 =R 11 R 12 R 13 SiO 1 / 2 D 1 =R 14 R 15 SiO 2 / 2 D 2 =R 16 R 17 SiO 2 / 2 D 3 =R 18 R 19 SiO 2 / 2 T 1 =R 20 SiO 3 / 2 T 2 =R 21 SiO 3 / 2 T 3 =R 22 SiO 3 / 2 Q 1 =If(OR 23 )1O 3 / 2 Q2 =Si(OR 24 )2O 2 / 2 Q 3 =Si(OR 25 )3O 1 / 2 Q 4 =Si(OR 26 )4 Q 5 =SiO 4 / 2 Here: a, b, c, d, e, f, g, h, i, j, k, l, o, and p are zero or any integers, and follow the following constraints: 1 ≤ [a + b + c + d + e + f + g + h + i + j + k + l + o + p] ≤ 6000; [b + e + h + k] ≥ 1; R 5 , R 6 , R 7 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 17 , R 19 , and R 20 are each independently selected from hydrogen, C1-C60 alkyl, C6-C60 aromatic-containing groups, C1-C10 alkoxy, and hydroxyl; R 8 , R 16 , R 21 , and R 24 are each independently selected from monovalent hydrophilic groups of the following formula, where G ≥ 0:

Chemical formula

[0008] In one embodiment, the hydrophilic group is a polyetheramine group selected from the following compounds: R 36 -(OR 37 -) q -NH2 R in the formula 36 R is selected from C1-C60 hydrocarbons, 37 q is selected from C1 to C60 hydrocarbons, and q is ≥ 1.

[0009] In one embodiment of the siloxane according to any of the preceding embodiments, the polyetheramine is selected from the following compounds: R 36 -(O-CH2CH2) x -(O-CCH2CH2CH2) y -(OCH2CH2CH(CH3)) z -NH2 Then x, y, and z are independent of each other, ranging from 0 to approximately 300, where x+y+z is ≥ 2.

[0010] In one embodiment of the siloxane according to any of the preceding embodiments, the polyetheramine group is selected by the following general formula: [ka] [ka] [ka] [ka] [ka]

[0011] In one embodiment, a siloxane containing a hydrophilic group is given by formula M 1 a M 2 b M 3 c Q 5 p The equation has such that b is ≥ 1.

[0012] In one embodiment of the siloxane according to any of the preceding embodiments, I is carboxylate-COO - , dicarboxylate (-R(COO-)2), sulfone-SO2-, sulfonate-SO3 - Sulfate-OSO3 - , phosphonate-PO3 2- phosphate-OPO3 2- group, -N + R 30 R 31 H, -N + H2R 32 , -N + Selected from H3 or ammonium salts, each comprising a cation independently selected from hydrogen or alkali metals, alkaline earth metals, transition metals, quaternary ammonium groups, and phosphonium groups, where R 30 , R 31 , and R 32 These are independently selected from C1-C30 hydrocarbons.

[0013] In one embodiment of the siloxane according to any of the preceding embodiments, I is of formula -R 33 -N + (R 34 )2-R 35 -I z A group is selected from those having R 33 R is a divalent hydrocarbon group having 1 to 20 carbon atoms. 34R is a monovalent hydrocarbon group having 1 to 20 carbon atoms. 35 is a divalent hydrocarbon group having 2 to 20 carbon atoms; and I z is carboxylate-COO - , sulfone-SO2-, sulfonate-SO3 - Sulfate-OSO3 - , phosphonate-PO3 2- , and phosphate-OPO3 2- It is an ionic group selected from the available groups.

[0014] In another embodiment, a composition for forming a silicone pressure-sensitive adhesive is provided, comprising (i) an MQ silicone resin, (ii) a polyorganosiloxane, and (iii) a siloxane containing hydrophilic groups.

[0015] In one embodiment, the siloxane comprises a hydrophilic functional group, where the hydrophilic functional group is selected from an ionic group, an ionizable group, an amphoteric group, a polyetheramine group, or a combination of two or more of these.

[0016] In one embodiment of the composition according to any of the preceding embodiments, the siloxane (iii) containing a hydrophilic group is selected from the following compounds: M 1 a M 2 b M 3 c D 1 d D 2 e D 3 f T 1 g T 2 h T 3 i Q 1 j Q 2 k Q 3 l Q 4 o Q 5 p wherein M 1 =R 5 R 6 R 7 SiO 1 / 2 M 2 =R 8 R 9 R 10 SiO 1 / 2 M 3 =R 11 R 12 R 13 SiO 1 / 2 D 1 =R 14 R 15 SiO 2 / 2 D 2 =R 16 R 17 SiO 2 / 2 D 3 =R 18 R 19 SiO 2 / 2 T 1 =R 20 SiO 3 / 2 T 2 =R 21 SiO 3 / 2 T 3 =R 22 SiO 3 / 2 Q 1 =Si(OR 23 )1O 3 / 2 Q 2 =Si(OR 24 )2O 2 / 2 Q 3 =Si(OR 25 )3O 1 / 2 Q 4 =Si(OR 26 )4 Q 5 =SiO 4 / 2 where: a, b, c, d, e, f, g, h, i, j, k, l, o, and p are zero or any integer, subject to the following constraints: 1≦[a+b+c+d+e+f+g+h+i+j+k+l+o+p]≦6000; [b+e+h+k]≧1; R 5 , R 6 , R 7 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 17 , R 19 , and R 20 Each of these is independently selected from hydrogen, C1-C60 alkyl, C6-C60 aromatic-containing group, C1-C10 alkoxy, and hydroxyl; R 8 , R 16 , R 21 , and R 24 Each is independently selected from the monovalent hydrophilic groups of the following equation, where G≧0: [ka] Here, A is a crosslinking unit between the siloxane moiety and the hydrophilic group I, having at least one spacer atom selected from C1-C60 acyclic hydrocarbon radicals, C4-C60 alicyclic radicals, C6-C60 aromatic hydrocarbon radicals, polyetheramines, polyethers, polyamides, polyesters, polyurethanes, polysulfones, polycarbonates, or two or more combinations thereof, where the crosslinking unit may contain one or more parts selected from alkoxys, carboxyls, urethanes, ureas, ketones, or two or more combinations thereof; I is an ionic group, an ionizable group, an amphoteric group, or a polar hydrophilic group; G is a polymerizable group having the following general formula: [ka] Formula --FK nonpolymerizable group, where F is a linking group selected from C1-C60 acyclic hydrocarbon radicals, C4-C60 alicyclic radicals, C6-C60 aromatic hydrocarbon radicals, polyetheramines, polyethers, polyamides, polyesters, polyurethanes, polysulfones, polycarbonates, or two or more combinations thereof, where the crosslinking group may include one or more parts selected from alkoxys, carboxyls, urethanes, ureas, ketones, or two or more combinations thereof; R 27 , R 28 , and R 29 These are independently selected from hydrogen or a monovalent hydrocarbon radical with 1 to 5 carbon atoms, and K is independently selected from hydrogen, C1-C60 acyclic hydrocarbon radicals, C4-C60 alicyclic radicals, C6-C60 aromatic hydrocarbon radicals, epoxy groups, or ether groups; R 11 , R 18 , and R 22 Each is independently selected from the base-AG, where A and G are as described above; and R 23 , R 25 , and R 26 is R 5 From R 22 You can choose any one of these, or any combination thereof, independently.

[0017] In one embodiment, a siloxane containing a hydrophilic group is given by formula M 1 a M 2 b M 3 c Q 5 p The expression is such that b is ≥ 1.

[0018] In one embodiment of the composition according to any of the preceding embodiments, I is carboxylate-COO - , dicarboxylate (-R(COO-)2), sulfone-SO2-, sulfonate-SO3 -Sulfate-OSO3 - , phosphonate-PO3 2- phosphate-OPO3 2- group, -N + R 30 R 31 H, -N + H2R 32 , -N + Selected from H3 or ammonium salts, each comprising a cation independently selected from hydrogen or alkali metals, alkaline earth metals, transition metals, quaternary ammonium groups, and phosphonium groups, where R 30 , R 31 , and R 32 These are independently selected from C1-C30 hydrocarbons.

[0019] In one embodiment of the composition according to any of the preceding embodiments, I is formula -R 33 -N + (R 34 )2-R 35 -I z A group is selected from those having R 33 R is a divalent hydrocarbon group having 1 to 20 carbon atoms. 34 R is a monovalent hydrocarbon group having 1 to 20 carbon atoms. 35 is a divalent hydrocarbon group having 2 to 20 carbon atoms; and I z is carboxylate-COO - , sulfone-SO2-, sulfonate-SO3 - Sulfate-OSO3 - , phosphonate-PO3 2- , and phosphate-OPO3 2- It is an ionic group selected from the available groups.

[0020] In one embodiment of the composition according to any of the preceding embodiments, I is a polar group selected from polyetheramines, polyethers, polyamides, polyesters, polyurethanes, polysulfones, and / or polycarbonates.

[0021] In one embodiment of the composition according to any of the above embodiments, the hydrophilic group is a polyetheramine group selected from the following compounds: R 36 -(OR 37 -) q -NH2 R in the formula 36 R is selected from C1-C60 hydrocarbons, 37 q is selected from C1 to C60 hydrocarbons, and q is ≥ 1.

[0022] In one embodiment, the polyetheramine is selected from the following compounds: R 36 -(O-CH2CH2) x -(O-CCH2CH2CH2) y -(OCH2CH2CH(CH3)) z -NH2 Then x, y, and z are independent of each other, ranging from 0 to approximately 300, where x+y+z is ≥ 2.

[0023] In one embodiment of the composition according to any of the preceding embodiments, the polyetheramine group is selected by the following general formula: [ka] [ka] [ka] [ka] [ka]

[0024] In one embodiment of the composition according to any of the preceding embodiments, the hydrophilic siloxane (iii) is present in an amount of about 0.1% to about 20% by weight based on the total weight of the composition.

[0025] In one embodiment of the composition according to any of the preceding embodiments, the hydrophilic siloxane (iii) is present in an amount of about 1.5% to about 8% by weight based on the total weight of the composition.

[0026] In yet another embodiment, a pressure-sensitive adhesive formed from a composition according to any of the preceding embodiments is provided.

[0027] In one embodiment, the adhesive contains less than 2500 ppm of one or more of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and / or dodecamethylcyclohexasiloxane.

[0028] In one embodiment, the adhesive contains less than 1000 ppm of one or more of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and / or dodecamethylcyclohexasiloxane.

[0029] In one embodiment, the adhesive contains less than 500 ppm of one or more of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and / or dodecamethylcyclohexasiloxane.

[0030] In one embodiment, the adhesive contains less than 100 ppm of one or more of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and / or dodecamethylcyclohexasiloxane.

[0031] In yet another embodiment, the provided article is one comprising a pressure-sensitive adhesive according to any of the preceding embodiments or designs.

[0032] In one embodiment, the article is selected from wound dressings, scar reduction dressings, drug delivery devices, medical tubes, clinical surfaces, pacemaker leads, wound healing patches, wound management devices, catheters, shunts, valves, stents, percutaneous patches, tissue engineering scaffolds, antimicrobial devices, ophthalmic devices, bioinserts, plugs, surgical devices, respiratory support devices, prosthetic devices, reconstructive devices, or implants.

[0033] In one embodiment, the article is selected from creams, lotions, bioactive compounds, deodorants, insecticides, cosmetic cosmetics, lipsticks, eyeshadows, stage makeup, hand cleaners, face masks, pore cleansers, knee or elbow protectors, bras, surgical gowns, nasal patches, prosthetics, cooling wraps, heat wraps, hearing aids, protective face masks, anti-snoring patches, jewelry, earrings, ornaments, tattoos, eyewear, tapes, or bandages.

[0034] The following description and drawings disclose various exemplary embodiments. Some improvements and novel aspects may be explicitly identified, while others may be evident from the description. [Modes for carrying out the invention]

[0035] Referencing the following exemplary embodiments, examples are illustrated in the accompanying drawings. As will be understood, other embodiments may also be used, and structural and functional modifications may be made. Furthermore, features of various embodiments may be combined or modified. Thus, the following description is presented merely as an example and does not in any way limit the various alternatives or modifications that may be made to the exemplary embodiments. In this disclosure, several specific details will lead to a complete understanding of the disclosed subject matter. It should be understood that embodiments of this disclosure may be carried out in other embodiments, which do not necessarily include all aspects described in this application or elsewhere.

[0036] As used in this application, the terms “example” and “illustration” mean examples or illustrations. The terms “example” or “illustration” do not indicate essential or preferred embodiments or forms. The term “or” is intended to be inclusive, not exclusive, unless the context suggests otherwise. For example, the statement “A uses B or C” includes any inclusive substitution (e.g., A uses B; A uses C; or A uses both B and C). Separately, the articles “one” and “a” are generally intended to mean “one or more,” unless the context suggests otherwise.

[0037] It is understood that the ranges for specific components can be combined to form new, unspecified ranges.

[0038] As used in this application, the term "hydrocarbon radical" generally refers to acyclic, cyclic (or alicyclic), and aromatic hydrocarbons, which may be saturated or unsaturated and may be optionally substituted or interrupted by one or more atoms or functional groups, such as carboxyl, cyano, hydroxyl, halo, and oxy. As understood, this term may include monovalent, divalent, and trivalent radicals, and in the context of a given formula or structure, the appropriate type of radical is intended.

[0039] As used in this application, the term “acyclic hydrocarbon radical” means a linear or branched hydrocarbon radical, preferably comprising 1 to 60 carbon atoms per radical, which may be saturated or unsaturated, and which may optionally be substituted or interrupted by one or more atoms or functional groups, such as carboxyl, cyano, hydroxy, halo, and oxy. Suitable monovalent acyclic hydrocarbon radicals include, for example, alkyl, alkenyl, alkynyl, hydroxyalkyl, cyanoalkyl, carboxyalkyl, alkyloxy, oxaalkyl, alkylcarbonyloxaalkylene, carboxyamide, and haloalkyl, such as methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl, and 3,3,3-fluoropropyl.

[0040] As used in this application, the term "alicyclic hydrocarbon radical" means a radical comprising one or more saturated hydrocarbon rings, preferably comprising 4 to 12 carbon atoms per ring and per radical, and optionally, one or more of the rings may be substituted with one or more alkyl radicals, halo radicals or other functional groups, each preferably comprising 2 to 6 carbon atoms per alkyl radical, and in the case of monovalent alicyclic hydrocarbon radicals comprising two or more rings, they may be fused rings. Suitable monovalent alicyclic hydrocarbon radicals include, for example, cyclohexyl and cyclooctyl.

[0041] As used in this application, the term “aromatic hydrocarbon radical” means a hydrocarbon radical containing one or more aromatic rings per radical, where the aromatic rings may optionally be substituted with one or more alkyl radicals, halo radicals, or other functional groups, each preferably containing 2 to 6 carbon atoms per alkyl radical, and in the case of a monocyclic aromatic hydrocarbon radical containing two or more rings, the rings may be fused. Suitable monovalent aromatic hydrocarbon radicals include, for example, phenyl, tolyl, 2,4,6-trimethylphenyl, 1,2-isopropylmethylphenyl, 1-pentalenyl, naphthyl, and anthryl. As used in this application, the term “aralkyl” means an aromatic derivative of an alkyl group, preferably a (C2-C6) alkyl group, where a portion of the alkyl partial aromatic derivative may optionally be interrupted by an oxygen atom, such as phenylethyl, phenylpropyl, 2-(1-naphthyl)ethyl, preferably phenylpropyl, phenoxypropyl, biphenyloxypropyl, etc.

[0042] In the context of this application, viscosity may be evaluated using any suitable method. Unless otherwise specified, viscosity is measured at 25°C using a Brookfield (DV1) viscometer.

[0043] Provided are compositions and processes for producing silicone-based materials. The composition comprises a mixture of components for producing silicone-based materials, including a siloxane containing a hydrophilic group component. The use of a siloxane containing a hydrophilic group has been found to result in autocatalytic activity, eliminating the need for an external catalyst to produce the silicone-based material. This process and composition can be used to produce silicone-based materials, such as silicone pressure-sensitive adhesives. The resulting materials produced from this composition and process may exhibit excellent properties, avoiding problems associated with the use of external catalysts, including solution clarity, reduced viscosity increase, low cyclic content, and others.

[0044] A composition for forming a silicone material comprises (i) a silicone resin; (ii) a polyorganosiloxane; and (iii) a siloxane containing a hydrophilic group. The silicone material (iii) can be selected from the polyorganosiloxane and / or the siloxane containing a hydrophilic group. This composition is substantially free of or does not contain an external catalyst. As used in this application, a composition is considered substantially free of an external catalyst if it contains less than 0.1% by weight, less than 0.01% by weight, or less than 0.001% by weight of the catalyst.

[0045] The composition contains a silicone resin (i). This silicone resin is typically called MQ silicone resin or MQ resin, and its formula is R3SiO 1 / 2 The M unit represented by, and the formula SiO 4 / 2 The Q unit is represented by , where R is generally selected from hydrocarbons from C1 to C60. This hydrocarbon can be selected from alkyl radicals, alicyclic radicals, unsaturated hydrocarbon radicals, and aromatic radicals. In one embodiment, R is selected from C1-C60 alkyl radicals, C2-C60 unsaturated radicals, C5-C60 alicyclic radicals, and C6-C60 aromatic radicals. In one embodiment, R is selected from C1-C10 alkyl radicals. In one embodiment, R is selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, or octyl.

[0046] In one embodiment, each R group is independently selected from monovalent C1-C6 hydrocarbons, C5-C20 alicyclic radicals, C2-C6 olefinic radicals, and C6-C20 aromatic radicals. Suitable examples of monovalent C1-C6 hydrocarbon radicals include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, and hexyl. Suitable examples of alicyclic radicals include, but are not limited to, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and others. Suitable examples of C2-C6 olefinic radicals include, but are not limited to, vinyl, allyl, and others. Suitable examples of aromatic radicals include, but are not limited to, phenyl. Within a given M, D, or T unit, each R group may be identical or different. In one embodiment, about 95 to 100% of the R groups are methyl. In one embodiment, substantially all of the R groups are non-unsaturated. In one embodiment, 0 to 0.5 mol% of the R groups in the MQ resin are unsaturated.

[0047] MQ resin is mainly formed from such M and Q units, but also contains some residual D units (R2SiO2). 2 / 2 ) and T units (RSiO 3 / 2 ) may contain. Generally, MQ resin contains less than 20 mol% D units and T units, less than 15 mol% D units and T units, less than 10 mol% D units and T units, less than 5 mol% D units and T units, and even less than 1 mol% D units and T units.

[0048] The ratio of M units to Q units in the silicone resin may be approximately 0.2:1 to approximately 1.7:1, approximately 0.4:1 to approximately 1.5:1, approximately 0.6:1 to approximately 1.2:1, or approximately 0.8:1 to approximately 1:1.

[0049] The silicone resin may contain some residual free silanol groups (Si-OH). In one embodiment, the silicone resin may have a silanol content of about 0.5% to about 12.0% by weight, about 0.75% to about 10% by weight, about 1% to about 7.5% by weight, or about 2.5% to about 5% by weight, based on the weight of the silicone resin.

[0050] Silicone resins can also be solids, liquids, dispersions, or solutions in solvents.

[0051] In an embodiment, the silicone resin may have a viscosity of about 1 cps to about 10,000 cps, about 10 cps to about 7,500 cps, about 25 cps to about 5,000 cps, about 50 cps to about 2,500 cps, or about 75 cps to about 1,000 cps. In an embodiment, the silicone resin may have a viscosity of about 1 cps to about 100 cps, about 100 to about 1,000 cps, or about 1,000 to about 10,000 cps. The viscosity of the silicone resin may be based on the silicone resin as a liquid; or on the silicone resin in a dispersion or solution, where the solids content of the silicone resin in the dispersion or solution is about 10% to about 98% solids. In one embodiment, the viscosity is based on a solution with about 60% solids.

[0052] Silicone resins can be a single type of silicone resin or a mixture of two or more different types of resins. Different resins can differ in terms of structure, viscosity, molecular weight, ratio of M units to Q units, and other properties.

[0053] According to aspects of the present invention, the silicone resin is provided as a solid resin, which is prepared by removing a volatile solvent from the resin, thereby providing a solid, solvent-free MQ resin. This can be achieved by spray drying.

[0054] Polyorganosiloxane (ii) is selected from silanol-terminated polyorganosiloxanes. In one embodiment, polyorganosiloxane (ii) is a silanol-terminated compound having the following formula: [ka] R in the formula 1 is hydroxy(-OH), and R 2 , R 3 , and R 4 The elements are independently selected from C1-C60 hydrocarbons, which may be optionally substituted with one or more halogen atoms, and n+m≧50 at 25°C.

[0055] In one embodiment, R 2 , R 3 , and R 4 The group is independently selected from C1-C60 alkyl, C1-C60 fluoroalkyl, C2-C60 alkenyl, C6-C60 aromatic-containing group, phenyl, aryl, arylalkyl, fluoroalkyl, or two or more combinations thereof. The aromatic-containing compound may include alkylaryl groups, arylalkyl groups, and groups containing two or more aromatic rings that may be separated or fused by bonding, linking groups. In one embodiment, R 2 , R 3 , and R 4 R is independently selected from C1-C10 alkyl and C6-30 aromatic, or comprises two or more combinations thereof. In one embodiment, R 2 R is selected from C1-C10 alkyl groups, 3 is selected from C1-C10 alkyl groups, and R 4 is selected from C6-C30 aromatic groups. In one embodiment, R 2 , R 3 , and R 4 Each of these is methyl. In one embodiment, R 2 and R 3 is methyl, and R 4It is phenyl.

[0056] Polyorganosiloxane (ii) is available in the following ranges: 300 to 200,000,000, approximately 500 to approximately 150,000,000, approximately 1,000 to approximately 100,000,000, approximately 2,500 to approximately 75,000,000, approximately 5,000 to approximately 50,000,000, approximately 10,000 to approximately 25,000,000, and approximately 20,000. The viscosity may range from approximately 10,000,000, 30,000 to approximately 5,000,000, 50,000 to approximately 1,000,000, 75,000 to approximately 750,000, 100,000 to approximately 500,000, or approximately 250,000 to approximately 400,000 centipoise (cps) at 25°C. The viscosity of polyorganosiloxane(II) can be easily measured using known conventional viscometers and techniques.

[0057] In one embodiment, the polyorganosiloxane(ii) has a viscosity of about 50,000 to about 750,000, about 75,000 to about 500,000, about 100,000 to about 400,000, or about 200,000 to about 300,000 cps.

[0058] As can be understood, polyorganosiloxane(ii) can be provided as a mixture of two or more different polyorganosiloxane compounds. Different polyorganosiloxanes can differ from one another in terms of structure, viscosity, size, and other respects. In one embodiment, polyorganosiloxane(ii) can include a mixture of a first polyorganosiloxane having an alkyl group and a second polyorganosiloxane having an alkyl group and an aromatic group. In one embodiment, polyorganosiloxane(ii) comprises a first polyorganosiloxane having a first viscosity and a second polyorganosiloxane having a second viscosity. In one embodiment, the first polyorganosiloxane has a viscosity greater than 15,000 cps, and the second polyorganosiloxane has a viscosity less than 12,000 cps. In one embodiment, the first polyorganosiloxane has a viscosity of about 15,000 cps to about 1,000,000 cps, about 25,000 cps to about 750,000 cps, about 50,000 cps to about 500,000 cps, or about 75,000 cps to about 250,000 cps; and the second polyorganosiloxane has a viscosity of about 500 cps to about 12,000 cps, about 1,000 cps to about 10,000 cps, about 2,500 cps to about 7,500 cps, or about 3,000 cps to about 5,000 cps.

[0059] The silicone resin (i) may be present in amounts of approximately 40% to approximately 70% by weight, approximately 45% to approximately 65% ​​by weight, or approximately 50% to approximately 55% by weight, based on the total weight of the silicone resin (i) and the polyorganosiloxane (ii). The polyorganosiloxane (ii) may be present in amounts of approximately 30% to approximately 60% by weight, approximately 35% to approximately 55% by weight, or approximately 45% to approximately 50% by weight, based on the total weight of the silicone resin (i) and the polyorganosiloxane (ii).

[0060] The composition comprises a siloxane (iii) containing a hydrophilic group. The siloxane containing a hydrophilic group can be selected from hydrophilic functionalized silicone resins (e.g., MQ-type resins) and / or hydrophilic functionalized polyorganosiloxanes. The hydrophilic functional group can be selected from ionic groups, ionizable groups, or amphoteric functional groups.

[0061] In one embodiment, the siloxane containing a hydrophilic group is a compound of the following formula: M 1 a M 2 b M 3 c D 1 d D 2 e D 3 f T 1 g T 2 h T 3 i Q 1 j Q 2 k Q 3 l Q 4 o Q 5 p

[0062] During the ceremony

[0063] M 1 =R 5 R 6 R 7 SiO 1 / 2

[0064] M 2 =R 8 R 9 R 10 SiO 1 / 2

[0065] M 3 =R 11 R 12 R 13 SiO 1 / 2

[0066] D 1 =R 14 R 15 SiO 2 / 2

[0067] D 2 =R 16 R 17 SiO 2 / 2

[0068] D 3 =R 18 R 19 SiO 2 / 2

[0069] T 1 =R 20 SiO 3 / 2

[0070] T 2 =R 21 SiO 3 / 2

[0071] T 3 =R 22 SiO 3 / 2

[0072] Q 1 =If(OR 23 )1O 3 / 2

[0073] Q 2 =If(OR 24 )2O 2 / 2

[0074] Q 3 =If(OR 25 )3O 1 / 2

[0075] Q 4 =If(OR 26 )4

[0076] Q 5 =SiO 4 / 2

[0077] Here:

[0078] a, b, c, d, e, f, g, h, i, j, k, l, o, and p are zero or any positive integer, subject to the following constraints:

[0079] 1≦[a+b+c+d+e+f+g+h+i+j+k+l+o+p]≦6000;

[0080] [b+e+h+k]≧1;

[0081] R 5 , R 6 , R 7 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 17 , R 19 , and R 20 Each of these is independently selected from hydrogen, C1-C60 alkyl, C6-C60 aromatic-containing group, C1-C10 alkoxy, and hydroxyl;

[0082] R 8 , R 16 , R 21 , and R 24 Each is independently selected from the monovalent hydrophilic groups of the following equation, where G≧0:

[0083] [ka]

[0084] Here, A is a crosslinking unit between the siloxane moiety and the hydrophilic group I, and has at least one spacer atom selected from a C1-C60 acyclic hydrocarbon radical, a C4-C60 alicyclic radical, a C6-C60 aromatic hydrocarbon radical, a polyetheramine, a polyether, a polyamide, a polyester, a polyurethane, a polysulfone, a polycarbonate, or a combination of two or more thereof, where the crosslinking unit may contain one or more moieties selected from alkoxy, carboxy, urethane, urea, ketone, or a combination of two or more thereof;

[0085] I is an ionic group, an ionizable group, an amphoteric ionic group, or a polar hydrophilic group or moiety;

[0086] G is a polymerizable group having the following general formula:

[0087]

Chemical formula

[0088] The non-polymerizable group of the formula --F-K, where F is a linking group selected from a C1-C60 acyclic hydrocarbon radical, a C4-C60 alicyclic radical, a C6-C60 aromatic hydrocarbon radical, a polyetheramine, a polyether, a polyamide, a polyester, a polyurethane, a polysulfone, a polycarbonate, or a combination of two or more thereof, where the crosslinking group may contain one or more moieties selected from alkoxy, carboxy, urethane, urea, ketone, or a combination of two or more thereof;

[0089] R 27 、R 28 、and R 29 are independently selected from hydrogen or a monovalent hydrocarbon radical of 1-5 carbon atoms, and

[0090] K is independently selected from hydrogen, C1-C60 acyclic hydrocarbon radicals, C4-C60 alicyclic radicals, C6-C60 aromatic hydrocarbon radicals, epoxy groups, or ether groups;

[0091] R 11 , R 18 , and R 22 Each is independently selected from the base-AG, where A and G are as described above; and

[0092] R 23 , R 25 , and R 26 is R 5 From R 22 You can choose any one of these, or any combination thereof, independently.

[0093] In one embodiment, A is a C1-C10 alkyl, C1-C10 cycloalkyl, or C6-C12 aromatic group. In one embodiment, A is a C1-C4 alkyl. As can be understood, depending on whether G is 0 or 1, the radical A is divalent or trivalent.

[0094] If I is an ionic group or an ionizable group, then I is a carboxylate-COO - , dicarboxylate (-R(COO-)2), sulfone-SO2-, sulfonate-SO3 - Sulfate-OSO3 - , phosphonate-PO3 2- phosphate-OPO3 2- group, -N + R 30 R 31 H, -N + H2R 32 , -N + A selection from an acid or base containing H3 or an ammonium salt, each containing a cation independently selected from hydrogen or alkali metals, alkaline earth metals, transition metals, quaternary ammonium groups, and phosphonium groups, where R 30 , R 31 , and R 32These are independently selected from C1-C30 hydrocarbons.

[0095] If I is an amphoteric moiety, the amphoteric group moiety is selected from groups that include anionic and cationic groups in the covalently bonded compound and whose total charge is neutralized. In one embodiment, the amphoteric group is of formula -R 33 -N + (R 34 )2-R 35 -I z A group having R is selected, where R 33 R is a divalent hydrocarbon group having 1 to 20 carbon atoms. 34 R is a monovalent hydrocarbon group having 1 to 20 carbon atoms. 35 is a divalent hydrocarbon group having 2 to 20 carbon atoms; and I z is carboxylate-COO - , sulfone-SO2-, sulfonate-SO3 - Sulfate-OSO3 - , phosphonate-PO3 2- , and phosphate-OPO3 2- It is an ionic group selected from the available groups.

[0096] In one embodiment, I is a polar group or polar moiety. A polar group or polar moiety refers to a group that is not inherently ionizable or ionic but contains a heteroatom that makes the group polar. Although not bound by any particular theory, a polar group may act as a hydrogen bond acceptor, and a group having a hydrogen atom directly bonded to a heteroatom may further act as a hydrogen bond donor. Suitable examples of polar groups or polar moieties include, but are not limited to, polyetheramines, polyethers, polyamides, polyesters, polyurethanes, polysulfones, and / or polycarbonates.

[0097] In one embodiment, the hydrophilic group is selected from polyetheramines. The polyetheramine can be selected from compounds comprising an amine group and at least one polyalkylene oxide group. In one embodiment, the polyetheramine is selected from compounds of the following formula:

[0098] R 36 -(OR 37 -) q -NH2 R in the formula 36 R is selected from C1-C60 hydrocarbons, 37 is selected from C1 to C60 hydrocarbons, and q is ≥ 1. In one embodiment, R 36 and R 37 R is independently selected from C1-C60 alkyl, C4-C30 cycloalkyl, and C6-C30 aromatic groups, where R 36 and R 37 It can optionally contain amine functional groups. In one embodiment, R 36 and R 37 R is independently selected from C1-C10 alkyl, C4-C10 cycloalkyl, and C6-C20 aromatic groups, where R 36 and R 37 The amine functional group may optionally be included. In one embodiment, q is 1 to about 200, about 4 to about 100, about 10 to about 50, or about 20 to about 40. In one embodiment, q is 2 to about 40, about 4 to about 30, about 6 to about 25, about 8 to about 20, or about 10 to about 15.

[0099] In one embodiment, the polyetheramine is selected from the following compounds:

[0100] R 36 -(O-CH2CH2) x -(O-CCH2CH2CH2) y -(OCH2CH2CH(CH3)) z -NH2 R in the formula 36is as described above, and x, y, and z are independently from 0 to about 300, where x + y + z is ≧2.

[0101] Some examples of suitable polyetheramines include, but are not limited to, the following:

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

[0102] In one embodiment, the siloxane (iii) containing a hydrophilic group is selected from MD-type polyorganosiloxanes. In one embodiment, the hydrophilic functionalized siloxane (iii) is selected from MQ-type silicone resins and has one or more M 2 groups as described above. In embodiments where the hydrophilic siloxane (iii) is an MQ-type resin, the hydrophilic siloxane can be of the formula M 1 a M 2 b M 3 c Q 5 p where b is ≧1.

[0103] The siloxane (iii) containing a hydrophilic group can be a solid, liquid, dispersion, or solution in a solvent.

[0104] Siloxane(iii) containing hydrophilic groups can, in embodiments, have viscosities of 1 cps to about 10,000 cps, about 10 cps to about 7,500 cps, about 25 cps to about 5,000 cps, about 50 cps to about 2,500 cps, or about 75 cps to about 1,000 cps. Siloxane(iii) containing hydrophilic groups can, in embodiments, have viscosities of about 1 cps to about 100 cps, about 100 cps to about 1,000 cps, or about 1,000 cps to about 10,000 cps. The viscosity of siloxane containing hydrophilic groups can be based on siloxane as a liquid; or siloxane in a dispersion or solution, where the solids content of siloxane containing hydrophilic groups in a dispersion or solution is about 10% to about 98% solids. In one embodiment, the viscosity is based on siloxane as a liquid.

[0105] Siloxane(iii) containing a hydrophilic group may be present in amounts of about 0.1% to about 20% by weight, about 0.5% to about 15% by weight, about 1% to about 10% by weight, about 2% to about 8% by weight, or about 3% to about 5% by weight, based on the total weight of the composition.

[0106] Siloxanes containing hydrophilic groups are prepared by the reaction of an olefin supporting at least one polar group with a silyl hydride in the presence of a hydrosilylation catalyst.

[0107] Silyl hydrides are selected from silicon-containing compounds that include at least one -SiH group. This -SiH group can be part of the M, D, or T unit of a siloxane. In one embodiment, silyl hydrides are selected when the -SiH is part of an M unit bonded to a Q unit. As used in this application, M is of the formula R3SiO 1 / 2 D represents the monofunctional group of the formula R2SiO 2 / 2 It represents a difunctional group, and T is in the formula RSiO 3 / 2 Q represents the trifunctional group of the formula SiO 4 / 2 It represents the tetrafunctional group.

[0108] Some non-limiting examples of silyl hydrides include pentamethyldisiloxane, e.g., P1535; tetramethyldisiloxane, e.g., T1437; heptamethyltrisiloxane, e.g., H1267; and tris(trimethylsiloxy)silane, e.g., T3520, all available from TCI; polymethylhydrosiloxanes include HMS-082, HMS-501, HPM-502, 65HMS-992, and HMS-064, all available from Gelest; polyhydrosilsesquioxanes, octakis(dimethylsiloxy)-T8-silsesquioxane, e.g., SiO6696.5 from Gelest; and other hydride-containing copolymers or homopolymers of dimethylsiloxane or phenyl-containing siloxanes, e.g., HDP-111-hydride-terminated poly-15phenyl(dimethylhydrosiloxy)siloxane, all available from Gelest.

[0109] Other examples of silyl hydride agents include, but are not limited to, Q resins, which may be referred to as MQ hydride or hydride-modified silica Q resin. These silyl hydrides have an activity of 1 to 25 equivalents / kg. Examples of these compounds, but are not limited to, those commercially available under the following trade names: MQH-9 (Milliken), which is a hydride-modified silica Q resin characterized by a molecular weight of 900 g / mol and an activity of 9.5 equivalents / kg; HQM-105 (Gelest), which is a hydride-modified silica Q resin characterized by a molecular weight of 500 g / mol and an activity of 8 to 9 equivalents / kg; and HQM-107 (Gelest), which is a hydride-modified silica Q resin characterized by a molecular weight of 900 g / mol and an activity of 8 to 9 equivalents / kg. The solids content of the resulting pressure-sensitive adhesive can be adjusted as desired using a suitable solvent. The solids content of the pressure-sensitive adhesive can be selected as desired depending on the specific purpose or intended use. In one embodiment, the solids content of the pressure-sensitive adhesive can be adjusted from about 30% to about 80%, from about 40% to about 70%, or from about 50% to about 60%. The solvent is preferably a non-aromatic solvent, and more preferably a solvent other than BTX (benzene, toluene, xylene) type solvents. Examples of suitable solvents that may be used to dissolve the pressure-sensitive adhesive include, but are not limited to, hydrocarbon solvents, silicone solvents, amides, esters, ketones, alcohols, or ethers. The solvent can be a natural or synthetic substance.

[0110] Suitable examples of aliphatic hydrocarbons include linear, branched, or cyclic aliphatic hydrocarbons having 6 to 16 carbon atoms, such as saturated acyclic aliphatic hydrocarbons (paraffins) like heptane, hexane, octane, isooctane, decane, and dodecane, and their isomers such as isodecane, isohexadecane, or isododecane, as well as cyclic aliphatic hydrocarbons like cyclohexane, methylcyclohexane, or decahydronaphthalene. The aliphatic hydrocarbon solvent can be an alkene, such as hebutene, cyclohexadiene, cyclohexene, or 2,5-dimethyl-2,4-hexadiene. Mixtures of aliphatic hydrocarbons are also suitable, such as the trademark ISOPAR. 登録商標 Below is a mixture of branched-chain paraffins sold. Other suitable materials include natural terpenes, such as, but are not limited to, pinene isomers, myrcene, bisabolene, cadinene, and others.

[0111] Examples of suitable volatile silicone solvents include, but are not limited to, linear, branched, and cyclic polydiorganosiloxanes, such as linear trimethylsilyl-terminated polydimethylsiloxanes having viscosities of 0.65 to 5 cP at 25°C, and cyclic polydimethylsiloxanes such as decamethylcyclopentasiloxane and octamethylcyclotetrasiloxane. Volatile silicone solvents may contain organic groups other than methyl, such as higher alkyl or phenyl groups. One example is 3-octylheptamethyltrisiloxane. In one embodiment, viscosity is determined by dissolving the resulting PSA molten material in a suitable solvent with a solid content of 60% and measuring the viscosity at 25°C using a Brookfield (DV1) viscometer.

[0112] Suitable ester solvents include, but are not limited to, carboxylate esters, such as alkyl carboxylate esters, and carbonate esters, such as alkyl carbonate esters. For example, volatile solvents may include at least one C1-C8 alkyl ester of a C2-C4 carboxylic acid, such as ethyl acetate or butyl acetate. Suitable carbonate ester solvents include, but are not limited to, diethyl carbonate and dicaprylyl carbonate.

[0113] Suitable ketone solvents include, but are not limited to, methyl isobutyl ketone (4-methyl-2-pentanone), 2-pentanone, 3-hexanone, methyl isoamyl ketone (5-methyl-2-hexanone), camphor, menthone, carvone, pulegone, and others.

[0114] Suitable ether solvents include, but are not limited to, dibutyl ether, volatile polyethers such as 1-(propoxymethoxy)propane, and cyclic ethers such as cyclopentamethyl ether.

[0115] Suitable alcohol solvents include, but are not limited to, methanol, ethanol, propanol, butanol, cis-3-hexanol, trans-2,cis-6-nonadienol, cis-6-noneol, linalool, geraniol, nerol, citronellol, nerolidol, farnesol, benzyl alcohol, phenylethyl alcohol, cinnamyl alcohol, citronellol, hydroxycitronellol, linalool, dihydrolinalool, tetrahydrolinalool, ethyllinalool, geraniol, nerol, tetrahydrogeraniol, myrcenol, dihydromyrcenol, tetrahydromyrcenol, osimenol, terpineol, menthol, borneol, phenethyl alcohol, farnesol, nerolidol, cedrol, terpineol, and others.

[0116] The silicone pressure-sensitive adhesives prepared by the method of this invention readily adhere to and support solid supports or substrates, whether flexible or rigid. These pressure-sensitive adhesive compositions may be applied to the bonding surface by any suitable means, such as rolling, spreading, or spraying. The surface of the support and the substrate to which the support is bonded may be any known solid material, such as metal, paper, wood, leather, textiles, organic polymer materials, painted surfaces, siliceous materials such as concrete, brick, concrete blocks, and glass cloth. After application to the surface, the adhesive may be cured by air drying or by heating at a temperature of, for example, up to 300°C.

[0117] In addition, the pressure-sensitive adhesive produced by this technology may exhibit a low concentration of cyclic siloxanes. In embodiments, the pressure-sensitive adhesive contains one or more of octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), or dodecamethylcyclohexasiloxane (D6) in amounts of less than 2500 ppm, less than 2000 ppm, less than 1800 ppm, less than 1500 ppm, less than 1250 ppm, less than 1000 ppm, less than 750 ppm, less than 500 ppm, less than 250 ppm, and even less than 100 ppm. In one embodiment, the pressure-sensitive adhesive contains each of the cyclic siloxanes D4, D5, or D6 in amounts less than 2500 ppm, less than 2000 ppm, less than 1800 ppm, less than 1500 ppm, less than 1250 ppm, less than 1000 ppm, less than 750 ppm, less than 500 ppm, less than 250 ppm, and even less than 100 ppm.

[0118] Adhesive materials formed from the compositions of the present invention can be provided by reacting the compositions in the presence of heat for a sufficient time to cause condensation of the silicone resin and for the silicone polymer to undergo molecular weight increase, crosslinking, or both. This process involves reacting a polyorganosiloxane and a silicone resin in the presence of a hydrophilic functionalized siloxane (e.g., a hydrophilic functionalized polyorganosiloxane and / or a hydrophilic functionalized silicone resin). In one embodiment, a solid silicone resin (in the form of an MQ-type resin) is dispersed in a polyorganosiloxane polymer and heated at a temperature of about 80 to about 150°C. The hydrophilic functionalized polyorganosiloxane and / or hydrophilic functionalized silicone resin is added to the mixture of polyorganosiloxane and silicone resin and heated for a sufficient time to allow the condensation reaction to occur to a selected degree. In one embodiment, no additional catalyst (e.g., a metal catalyst such as a platinum-based catalyst, but not limited to) is required to form a cured material.

[0119] The pressure-sensitive adhesive formed from the composition of the present invention is suitable for a number of applications. This pressure-sensitive adhesive exhibits appropriate hydrophilicity while simultaneously showing excellent adhesion and other properties desirable for a variety of applications. In one embodiment, this pressure-sensitive adhesive can be used in gels, emulsions, healthcare applications, household applications, clothing, sports equipment such as driving masks, paints, coatings, fuel cells, electronic and electro-optical applications, agriculture, films, injection-molded and compression-molded rubbers and plastics, various silicone rubbers, the manufacture of home appliances, the manufacture of machinery and equipment, coatings such as release coatings, protective coatings, and antifouling coatings, and consumer goods, for example, but not limited to, personal care products, beauty products, cosmetics, and other application fields. As a specific example, in the healthcare field, silicone elastomers are used in the manufacture of wound dressings, scar reduction dressings, drug delivery devices, medical tubing, clinical surfaces, pacemaker leads, pressure-sensitive adhesives, wound healing patches, wound management devices, medical adhesives, catheters, shunts, valves, stents, percutaneous patches, tissue engineering scaffolds, antimicrobial devices, ophthalmic devices, bioinserts, plugs, surgical devices, medical devices, medical storage devices, childcare products, ventilator assist devices, prosthetic devices, reconstructive devices, and implants.

[0120] This adhesive may find applications in personal care products. It may be useful for bonding cosmetic or drug delivery articles that deliver substances to the skin, such as skin treatment substances, creams, lotions, hormones, vitamins, deodorants, and medicines; cosmetic or drug delivery articles that deliver substances to be released away from the skin, such as insecticides, inhalants, and perfumes; functional articles that do not necessarily adhere to the skin but require a long period of residence on the skin, such as cosmetic cosmetics, lipsticks, eyeshadows, and stage makeup; and functional articles that adhere to the skin, such as cleansing articles (hand cleaners, face masks, and sanitary pore cleansers). In addition, this adhesive may also find applications in protective items such as knee or elbow protectors or bandages; clothing such as bras, surgical gowns, or partial garments for fitting in a tailor; nasal patches; prosthetics such as breast implants or wigs; cooling wraps for relieving pain and reducing swelling from bruises, for example; heat wraps for relieving temporary and chronic pain such as neck wraps and knee wraps; hearing aids; protective face masks (for reducing or preventing the inhalation of harmful substances); anti-snoring patches; decorative items such as jewelry, earrings, ornaments, and tattoos; goggles and other eyewear; tapes, bandages, and others for attaching to the skin.

[0121] The curable compositions of the present invention can be made antimicrobial by contact with antimicrobial agents, exemplified by silver, copper, zinc, chlorhexidine, benzalkonium chloride, biguanides, polyquaternary ammonium compounds, polyquaternary phosphonium compounds, chitosan and its derivatives, and antimicrobial peptides, nisin, pediosin, gomesin, piericidine, and derivatives and recombinants thereof that can bind to ionic groups present on the silicone ionomer of the present invention, but are not limited to these.

[0122] These microbial fungicides can be released upon contact with the physiological or clinical environment and provide temporary or permanent antimicrobial effects at the contact site.

[0123] In yet another example, addition-curing pressure-sensitive silicone adhesives are used to adhere wound dressings to the skin surrounding a wound. The silicone adheres to the skin rather than to the wound surface. Therefore, they can be removed or repositioned without causing damage.

[0124] This technology has been described in the above detailed description with reference to various aspects and embodiments. This technology may be further understood by referring to the following examples. The examples are intended to further illustrate aspects and embodiments of this technology and are not necessarily limited to such aspects or embodiments.

[0125] Examples

[0126] MQ silicone resin

[0127] Solid MQ silicone resins used in the preparation of PSA. The solid MQ silicone resins used for the preparation of the pressure-sensitive adhesive had silanol content ranging from 95,473 ppm to 47,746 ppm. The MQ resins used are referred to as MQ1 resin (silanol content 95,473 ppm), MQ2 resin (silanol content 47,746 ppm), MQ3 resin (silanol content 56,642 ppm), and MQ4 resin (silanol content 80,722 ppm).

[0128] Polyorganosiloxane

[0129] Ingredients 1-3

[0130] Components 1, 2, and 3 describe polyorganosiloxanes according to the aspects and embodiments of the present invention, and also based on properties such as molecular weight (MW) and cyclic siloxane content.

[0131] The mass quantities (MWs) of the components, examples, and comparative examples were determined by gel filtration chromatography (GPC) using chloroform solvent and calibrated using polystyrene standards. The viscosity of the components, examples, and comparative examples was determined at 25°C using a Brookfield (DV1) viscometer with spindles #2 to #6. The cyclic siloxane content of the components, examples, and comparative examples was quantified using gas chromatography.

[0132] The polyorganosiloxanes of components 1 to 3 are listed in Table 1 below:

[0133] [Table 1]

[0134] 4 siloxane components containing hydrophilic groups

[0135] Dicarboxylate polydimethylsiloxane was prepared as described in Synthesis Example 1 of EP3280496A1.

[0136]

[0137] Ingredient 5

[0138] Silsoft TM BAPD fluid and aminopolydimethylsiloxane were used as component 5.

[0139] Ingredient 6 MQH-9, or MQ hydride (100 grams), was introduced into a 500 mL three-necked round-bottom flask equipped with a water condenser, a thermo-pocket, and a dropping funnel, while sparging nitrogen into the flask. The dropping funnel was filled with allyl succinic anhydride (CAS No. 7539-12-0) (72.2 g). The contents of the round-bottom flask were heated to 85°C, and 7.22 g of allyl succinic anhydride was added to the flask. To this mixture, 10 ppm of Karstedt catalyst (CAS No. 68478-92-2) was added, followed by the addition of the remaining allyl succinic anhydride from the dropping funnel dropwise. The reaction was allowed to proceed for 4 to 5 hours. Next, triisopropoxy(vinyl)silane (CAS No. 18023-33-1) (119.8 g) was poured into a dropping funnel and added dropwise to a round-bottom flask, and the reaction was allowed to proceed again for 4 to 5 hours. After the reaction, the round-bottom flask was cooled to 50°C and held under vacuum for 2 hours to obtain ionic MQ resin. The ionic MQ resin was analyzed using GPC and showed a single-peaked resin peak.

[0140] Ingredient 7

[0141] MQH-9, or MQ hydride (100 grams), was introduced into a 500 mL three-necked round-bottom flask equipped with a water condenser, a thermo-pocket, and a dropping funnel, while sparging nitrogen into the flask. The dropping funnel was filled with vinylcyclohexene oxide (CAS No. 106-86-5) (64.0 g). The contents of the round-bottom flask were heated to 85°C, and 6.4 g of vinylcyclohexene oxide was added to the flask. To this mixture, 10 ppm of Karstedt catalyst (CAS No. 68478-92-2) was added, followed by the addition of the remaining vinylcyclohexene oxide in the dropping funnel dropwise. The reaction was allowed to proceed for 4 to 5 hours. Next, triisopropoxy(vinyl)silane (CAS No. 18023-33-1) (119.8 g) was poured into a dropping funnel and added dropwise to a round-bottom flask, and the reaction was allowed to proceed again for 4 to 5 hours. After the reaction, the round-bottom flask was cooled to 50°C, Jeffamine M-600 (CAS No. 83713-01-3) (300.93 g) was added, and the reaction was allowed to proceed for 24 hours. After 24 hours, the contents of the round-bottom flask were held under vacuum for 2 hours to obtain a polyether-functionalized MQ resin. The polyether-functionalized MQ resin was analyzed using GPC and showed a single-peaked resin peak.

[0142] Ingredient 8

[0143] Ethylene glycol monoallyl ether (CAS No. 111-45-5) (100 g), N,N-dimethylcarbamilcloride (CAS No. 79-44-7) (115.83 g), and 4-(dimethylamino)pyridine (CAS No. 1122-58-3) (5.98 g) were placed in a 500 mL two-necked round-bottom flask equipped with a condenser and a thermopocket. The contents of the round-bottom flask were heated to 80°C, and the reaction was allowed to proceed for 24 hours to synthesize 2-allyloxyethyl N,N-dimethylcarbamate. The product was dissolved in hexane and washed with a 1N HCl solution, followed by 1N sodium bicarbonate and saturated brine. The organic phase was dried over anhydrous sodium sulfate, and then hexane was removed by vacuum distillation. 200 g of 2-allyloxyethyl N,N-dimethylcarbamate was obtained.

[0144] MQH-9, or MQ hydride (100 grams), was introduced into a 1000 mL three-necked round-bottom flask equipped with a water condenser, a thermo-pocket, and a dropping funnel, while sparging nitrogen. The dropping funnel was filled with 2-allyloxyethyl N,N-dimethylcarbamate (89.3 g). The contents of the round-bottom flask were heated to 85°C, and 8.9 g of 2-allyloxyethyl N,N-dimethylcarbamate was added to the round-bottom flask. To this mixture, 10 ppm of Karstedt catalyst (CAS No. 68478-92-2) was added, followed by the addition of the remaining 2-allyloxyethyl N,N-dimethylcarbamate from the dropping funnel dropwise. The reaction was allowed to proceed for 4 to 5 hours. Next, triisopropoxy(vinyl)silane (CAS No. 18023-33-1) (119.8 g) was poured into a dropping funnel and added dropwise to a round-bottom flask, and the reaction was allowed to proceed again for 4 to 5 hours. After the reaction, the round-bottom flask was cooled to 50°C. Tetrahydrofuran (CAS No. 109-99-9) (300 mL) and chloroacetic acid (CAS No. 79-11-8) (48.7 g) were added to the round-bottom flask, and the reaction was allowed to proceed for 24 hours. Tetrahydrofuran was removed under reduced pressure distillation to obtain an amphoteric MQ resin. The amphoteric MQ resin was analyzed using GPC and showed a monomodal resin peak.

[0145] Preparation of silicone PSA

[0146] Example 1

[0147] Component 1 polyorganosiloxane (52.07 g) and Component 2 polyorganosiloxane (52.07 g) were placed in a 3-liter planetary mixer equipped with helical blades and a heating device, thermocouple, and sparge tube (for nitrogen sparging), followed by the addition of MQ3 (171.84 g), or the order was reversed. The reactor temperature was initially set to 125–130°C under a positive nitrogen flow. The above mixture was stirred at a final temperature of 135–145°C until a completely homogeneous solution / dispersion was obtained. This mixing process was continued for 1–4 hours until MQ3 was completely dissolved or dispersed in the polyorganosiloxane mixture. 12 g (4%) of Component 4 was added, and the reaction was continued for a further 7 hours. The reactor temperature was maintained at 145°C under vacuum for 1–2 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~200 grams) at 50°C to adjust the solid content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0148] Example 2

[0149] In a glass reactor equipped with a helical blade, heating device, thermocouple, sparge tube (for nitrogen sparging), and a Dean-Stark water trap filled with heptane, 18 grams of polyorganosiloxane component 2 and 18 grams of polyorganosiloxane component 3 were added, followed by 54 grams of MQ4 in 36 grams of heptane. The mixture was homogeneously mixed under a positive nitrogen stream at 90°C for 3 hours. 3.6 grams (4%) of component 4 were added, and the reaction was continued for 12 hours. The reaction temperature was raised to 110°C, and the mixture was refluxed until the last stream of water was observed. The resulting PSA was obtained in heptane solution. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0150] Example 3

[0151] Component 2, polyorganosiloxane (36 g), was placed in a 3-liter planetary mixer equipped with helical blades and a heating device, thermocouple, and sparge tube (for nitrogen sparging), followed by the addition of MQ4 (54 g), or the order was reversed. The reactor temperature was initially set to 125-130°C under a positive nitrogen flow. The above mixture was stirred at 135-145°C until a completely homogeneous solution / dispersion was obtained. This mixing process was continued for 1-4 hours until MQ4 was completely dissolved or dispersed in the polyorganosiloxane. 3.6 g (4%) of component 5 was added, and the reaction was continued for a further 12 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~60 g) at 50°C to adjust the solids content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0152] Example 4

[0153] In a glass reactor equipped with helical blades and heating devices, thermocouples, and sparge tubes (for nitrogen sparging), 16.98 grams of polyorganosiloxane component 1 and 16.98 grams of polyorganosiloxane component 2 were added, followed by the addition of MQ4 (53.79 grams), or the reverse order. The reactor temperature was initially set to 125-130°C under a positive nitrogen flow. The mixing process continued overnight until MQ4 was completely dissolved or dispersed in the polyorganosiloxane mixture. 2.25 grams (2.5%) of component 6 was added, and the reaction was continued for a further 12 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~60 grams) at 50°C to adjust the solids content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0154] Example 5

[0155] In a glass reactor equipped with helical blades and a heating device, thermocouples, and sparge tubes (for nitrogen sparging), 16.98 grams of polyorganosiloxane component 1 and 16.98 grams of polyorganosiloxane component 2 were added, followed by the addition of MQ4 (51.54 grams), or the reverse order. The reactor temperature was initially set to 125-130°C under a positive nitrogen flow. The mixing process was continued overnight until MQ4 was completely dissolved or dispersed in the polyorganosiloxane mixture. 4.5 grams (5%) of component 6 were added, and the reaction was continued for a further 12 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~60 grams) at 50°C to adjust the solids content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0156] Example 6

[0157] In a glass reactor equipped with helical blades and a heating device, thermocouples, and sparge tubes (for nitrogen sparging), 38.30 grams of polyorganosiloxane component 2 was added, followed by 49.45 grams of MQ4, or the order was reversed. The reactor temperature was set to 125-130°C under a positive nitrogen flow. The mixing process continued overnight until MQ4 was completely dissolved or dispersed in the polyorganosiloxane mixture. 2.25 grams (2.5%) of component 7 was added, and the reaction was continued for a further 7 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~60 grams) at 50°C to adjust the solids content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0158] Example 7

[0159] In a glass reactor equipped with helical blades and a heating device, thermocouples, and sparge tubes (for nitrogen sparging), 38.30 grams of polyorganosiloxane (component 2) were added, followed by 47.20 grams of MQ4 (component 47.20 grams), or the order was reversed. The reactor temperature was set to 125-130°C under a positive nitrogen flow. The mixing process continued overnight until MQ4 was completely dissolved or dispersed in the polyorganosiloxane. 4.5 grams (5%) of component 7 were added, and the reaction was continued for a further 7 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~60 grams) at 50°C to adjust the solids content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0160] Example 8

[0161] In a glass reactor equipped with helical blades and a heating device, thermocouples, and sparge tubes (for nitrogen sparging), 38.30 grams of polyorganosiloxane (component 2) were added, followed by 42.70 grams of MQ4 (component 42.70 grams), or the order was reversed. The reactor temperature was set to 125-130°C under a positive nitrogen flow. The mixing process continued overnight until MQ4 was completely dissolved or dispersed in the polyorganosiloxane. 9.0 grams (10%) of component 7 were added, and the reaction was continued for a further 7 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~60 grams) at 50°C to adjust the solids content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0162] Example 9

[0163] In a glass reactor equipped with helical blades and a heating device, thermocouples, and sparge tubes (for nitrogen sparging), 16.98 grams of polyorganosiloxane component 1 and 16.98 grams of polyorganosiloxane component 2 were added, followed by the addition of MQ4 (53.79 grams), or the reverse order. The reactor temperature was set to 125-130°C under a positive nitrogen flow. The mixing process was continued overnight until MQ4 was completely dissolved or dispersed in the polyorganosiloxane. 2.25 grams (2.5%) of component 8 was added, and the reaction was continued for a further 7 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~60 grams) at 50°C to adjust the solids content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0164] Example 10

[0165] In a glass reactor equipped with helical blades and a heating device, thermocouples, and sparge tubes (for nitrogen sparging), 16.98 grams of polyorganosiloxane component 1 and 16.98 grams of polyorganosiloxane component 2 were added, followed by the addition of MQ4 (51.54 grams), or the reverse order. The reactor temperature was set to 125-130°C under a positive nitrogen flow. The mixing process was continued overnight until MQ4 was completely dissolved or dispersed in the polyorganosiloxane mixture. 4.5 grams (5%) of component 8 was added, and the reaction was continued for a further 7 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~60 grams) at 50°C to adjust the solids content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0166] Example 11

[0167] In a glass reactor equipped with helical blades and a heating device, thermocouples, and sparge tubes (for nitrogen sparging), 16.98 grams of polyorganosiloxane component 1 and 16.98 grams of polyorganosiloxane component 2 were added, followed by the addition of MQ4 (47.04 grams), or the reverse order. The reactor temperature was set to 125-130°C under a positive nitrogen flow. The mixing process was continued overnight until MQ4 was completely dissolved or dispersed in the polyorganosiloxane mixture. 9.0 grams (10%) of component 8 was added, and the reaction was continued for a further 7 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~60 grams) at 50°C to adjust the solids content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks.

[0168] Comparative Example 1

[0169] In a 3-liter planetary mixer equipped with helical blades and a heating device, thermocouples, and sparge tubes (for nitrogen sparging), 153.19 grams of polyorganosiloxane (component 2) were added, followed by 206.81 grams of MQ4, or the order was reversed. The reactor temperature was set to 125–130°C under a positive nitrogen flow. The above mixture was stirred at 125–130°C until a completely homogeneous solution / dispersion was obtained. This mixing process was continued for 1–4 hours until MQ4 was completely dissolved or dispersed in the polyorganosiloxane. 2.0 grams of 2,4,6-trimethyl-2,4,6-trivinylcyclotrisilazane (CAS-No: 5505-72-6) were added, and the reaction was continued for a further 3 hours. Finally, the reactor temperature was raised to 150°C and maintained under nitrogen for 2–3 hours. After this reaction step, the reactor was cooled. The resulting highly viscous mass was then dissolved in 40 parts ethyl acetate (~200 grams) at 50°C to adjust the solid content to 60%. The GPC of the PSA showed multi-peaked resin and polymer peaks. [Table 2]

[0170] Adhesive performance

[0171] PSA samples were coated to a thickness of 70-80 micrometers, and probe tack adhesion and peel strength adhesion were measured. The adhesive used was 3M's Scotchpak. TM Applied onto a 9733 polyester film laminate support, and 3M's Scotchpak TM 1022 release liner was used. The adhesive was dried in an oven at 90°C for 10 minutes. Tack tests were performed according to FINAT Test Method 9, and tack was measured in grams. Peel adhesion tests were performed according to ASTM D3330 / D3330M, and the adhesion to a mirror-finish stainless steel plate was measured at a peel angle of 180°. Peel adhesion results were recorded per inch strip as peel force in N / inch at a peel rate of 12 inches per minute from the stainless steel panel. [Table 3]

[0172] Estimation of cyclic siloxane content

[0173] The cyclic siloxane content in PSA was quantified using gas chromatography. Samples were extracted over 24 hours as described below.

[0174] Experimental method:

[0175] Approximately 0.5 g of the sample was weighed into a vial. The exact weight was recorded. Using acetone as the solvent, the sample was extracted for 24 hours in 10 mL of working solution prepared with toluene and dodecane as internal standards (0.05 mg / mL). Calibration plots for cyclic siloxanes D4, D5, and D6 were generated by preparing various concentration standards ranging from 0.005 to 0.1 mg / mL in acetone. The peak areas were normalized by dividing by the peak area for dodecane and plotted against concentration. The cyclic siloxanes present in the sample were calculated using the normalized peak areas and calibration curves in the sample's GC chromatogram.

[0176] GC conditions Equipment: Agilent 7890A GC Detector: FID 350℃; H2: 30 mL / min, Air: 300 mL / min, Makeup flow: 25.4 mL / min Sample introduction: Split injection / 225°C / Split ratio 50:1 Injection volume: 2 μL (Agilent 7693 autosampler) Carrier gas: Nitrogen (1.4 mL / min, constant flow mode) Capillary column: Agilent HP-5 (30m x 0.32mm x 0.25μm) Temperature program: From 50°C (5 minutes) to 200°C at a rate of 15°C / minute, then up to 315°C (20 minutes). [Table 4]

[0177] Viscoelastic properties

[0178] The viscoelastic properties of silicone PSAs prepared by the process described herein were fully characterized by dynamic rheological analysis. G' at low angular frequencies (w=0.01 rad / s) represents the adhesive strength during application, while G' at high angular frequencies (w=100 rad / s) relates to the peeling force during desorption. Complex viscosity values, on the other hand, compare the cold flow properties of these adhesives. The data shown in Table 5 suggest that for all given compositions [Examples 1 to 11], the PSA properties are comparable to those using known state-of-the-art condensation catalysts. The experimental method involved molding the PSA onto a suitable release liner, drying at 150°C for 1 hour, and then transferring it from the release liner to a DHR3 rheometer (TA Instruments). A 25 mm parallel plate configuration was used in vibration mode, and flow curves were generated with an angular strain of 0.01%. [Table 5]

[0179] Moisture intake from DSC

[0180] Experimental method: A PSA sample was applied to a release liner, which was a PET foil coated with fluororesin. This foil was dried at 100°C for 8 hours. The PSA-coated foil was then immersed in a boiling water bath for 10 minutes. The coated surface was air-dried to remove surface moisture. The PSA-coated foil was then analyzed using DSC to quantitatively estimate water uptake. [Table 6]

[0181] The above description includes examples provided herein. Of course, for the purposes of this specification, it is impossible to describe all recognizable combinations of components or methodologies, but those skilled in the art will recognize that many further combinations and substitutions of this specification are possible. Thus, this specification is intended to encompass all such changes, modifications and variations that are included within the idea and scope of the appended claims. Furthermore, wherever the term “encompasses” is used in the detailed description or claims, such term is intended to be as comprehensive as “includes,” as is the case when “includes” is used as a substitute in the claims.

[0182] The above description illustrates various non-limiting embodiments of silicone compositions, adhesives formed from the compositions, and articles using the compositions or adhesives. Modifications may be conceived by those skilled in the art and those who create and use the present invention. The disclosed embodiments are for illustrative purposes only and are not intended to limit the scope of the invention or subject matter described in the claims.

Claims

1. A siloxane containing a hydrophilic group, having the following formula: M １ ａ M ２ ｂ M ３ ｃ D １ ｄ D ２ ｅ D ３ ｆ T １ ｇ T ２ ｈ T ３ ｉ Q １ ｊ Q ２ ｋ Q ３ ｌ Q ４ ｏ Q ５ ｐ During the ceremony M １ =R ５ R ６ R ７ SiO １／２ M ２ =R ８ R ９ R １０ SiO １／２ M ３ =R １１ R １２ R １３ SiO １／２ D １ =R １４ R １５ SiO ２／２ D ２ =R １６ R １７ SiO ２／２ D ３ =R １８ R １９ SiO ２／２ T １ =R ２０ SiO ３／２ T ２ =R ２１ SiO ３／２ T ３ =R ２２ SiO ３／２ Q １ =Si(OR ２３ ) １ O ３／２ Q ２ =Si(OR ２４ ) ２ O ２／２ Q ３ =Si(OR ２５ ) ３ O １／２ Q ４ =Si(OR ２６ ) ４ Q ５ =SiO ４／２ Here: a, b, c, d, e, f, g, h, i, j, k, l, o, and p are zero or any positive integer, subject to the following constraints: 1≦[a+b+c+d+e+f+g+h+i+j+k+l+o+p]≦6000; [b+e+h+k]≧1; R ５ 、 R ６ 、 R ７ 、 R ９ 、 R １０ 、 R １２ 、 R １３ 、 R １４ 、 R １５ 、 R １７ 、 R １９ 、 and R ２０ are each independently selected from hydrogen, C1-C60 alkyl, C6-C60 aromatic-containing group, C1-C10 alkoxy, and hydroxyl; R ８ , R １６ , R ２１ , and R ２４ are each independently selected from monovalent hydrophilic groups of the following formula, where G ≧ 0: 【Chemistry 23】 Here, A is a crosslinking unit between the siloxane moiety and the hydrophilic group I, having at least one spacer atom selected from C1-C60 acyclic hydrocarbon radicals, C4-C60 alicyclic radicals, C6-C60 aromatic hydrocarbon radicals, polyetheramines, polyethers, polyamides, polyesters, polyurethanes, polysulfones, polycarbonates, or two or more combinations thereof, where the crosslinking unit may contain one or more parts selected from alkoxys, carboxyls, urethanes, ureas, ketones, or two or more combinations thereof; I includes, but is not limited to, ionic groups, ionizable groups, amphoteric groups, or polar hydrophilic groups or parts thereof, polyetheramines, polyethers, polyamides, polyesters, polyurethanes, polysulfones, or polycarbonates; G is a polymerizable group having the following general formula: 【Chemistry 24】 A nonpolymerizable group of formula F-K, where F is a linking group selected from C1-C60 acyclic hydrocarbon radicals, C4-C60 alicyclic radicals, C6-C60 aromatic hydrocarbon radicals, polyetheramines, polyethers, polyamides, polyesters, polyurethanes, polysulfones, polycarbonates, or two or more combinations thereof, where the crosslinking group may include one or more parts selected from alkoxys, carboxyls, urethanes, ureas, ketones, or two or more combinations thereof; R ２７ , R ２８ , and R ２９ These are independently selected from hydrogen or a monovalent hydrocarbon radical with 1 to 5 carbon atoms, and K is independently selected from hydrogen, C1-C60 acyclic hydrocarbon radicals, C4-C60 alicyclic radicals, C6-C60 aromatic hydrocarbon radicals, epoxy groups, or ether groups; R １１ , R １８ , and R ２２ Each is independently selected from bases A-G, where A and G are as described above; and R ２３ , R ２５ , and R ２６ is R ５ From R ２２ Siloxanes, which can be independently selected from any one or a combination thereof.

2. The hydrophilic group is a polyetheramine group selected from the following compounds: R ３６ -(O-R ３７ -) ｑ -NH ２ In the formula R ３６ R is selected from C1 to C60 hydrocarbons, ３７ The siloxane of claim 1, wherein is selected from C1 to C60 hydrocarbons, and q is ≥ 1.

3. Polyetheramines are selected from the following compounds: R ３６ -(O-CH ２ CH ２ ) ｘ -(O-CCH ２ CH ２ CH ２ ) ｙ -(OCH ２ CH ２ CH(CH ３ )) ｚ -NH ２ The siloxane of claim 1 or 2, wherein x, y, and z are independently from 0 to about 300, where x + y + z ≥ 2.

4. The polyetheramine group is selected by the following general formula: 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 The siloxane according to claim 2 or 3.

5. Siloxanes containing hydrophilic groups are given by formula M １ ａ M ２ ｂ M ３ ｃ Q ５ ｐ The siloxane of claim 1, wherein b is ≥ 1.

6. I is carboxylate-COO － , dicarboxylate (-R(COO-) ２ ), sulfone-SO ２ -, sulfonate-SO ３ － Sulfate-OSO ３ － , phosphonate-PO ３ ２－ phosphate-OPO ３ ２－ Group, -N ＋ R ３０ R ３１ H, -N ＋ H ２ R ３２ , -N ＋ H ３ Selected from , or ammonium salts, each comprising a cation independently selected from hydrogen or alkali metals, alkaline earth metals, transition metals, quaternary ammonium groups, and phosphonium groups, where R ３０ , R ３１ , and R ３２ A siloxane according to claim 1 or 5, wherein is independently selected from C1 to C30 hydrocarbons.

7. I is equation -R ３３ -N ＋ (R ３４ ) ２ -R ３５ -I ｚ A group having R is selected, where R ３３ R is a divalent hydrocarbon group having 1 to 20 carbon atoms. ３４ R is a monovalent hydrocarbon group having 1 to 20 carbon atoms. ３５ is a divalent hydrocarbon group having 2 to 20 carbon atoms; and I ｚ is carboxylate-COO － , sulfone-SO ２ -, sulfonate-SO ３ － Sulfate-OSO ３ － , phosphonate-PO ３ ２－ , and phosphate-OPO ３ ２－ The composition according to claim 1 or 5, wherein the ionic group is selected from the group.

8. A composition for forming a silicone pressure-sensitive adhesive, comprising (i) MQ silicone resin, (ii) polyorganosiloxane, and (iii) siloxane containing hydrophilic groups.

9. The composition of claim 8, wherein the siloxane comprises a hydrophilic functional group, where the hydrophilic functional group is selected from an ionic group, an ionizable group, an amphoteric group, a polyetheramine group, or a combination of two or more of these.

10. Siloxane (iii) containing a hydrophilic group is selected from the following compounds: M １ ａ M ２ ｂ M ３ ｃ D １ ｄ D ２ ｅ D ３ ｆ T １ ｇ T ２ ｈ T ３ ｉ Q １ ｊ Q ２ ｋ Q ３ ｌ Q ４ ｏ Q ５ ｐ During the ceremony M １ =R ５ R ６ R ７ SiO １／２ M ２ =R ８ R ９ R １０ SiO １／２ M ３ =R １１ R １２ R １３ SiO １／２ D １ =R １４ R １５ SiO ２／２ D ２ =R １６ R １７ SiO ２／２ D ３ =R １８ R １９ SiO ２／２ T １ =R ２０ SiO ３／２ T ２ =R ２１ SiO ３／２ T ３ =R ２２ SiO ３／２ Q １ =Si(OR ２３ ) １ O ３／２ Q ２ =Si(OR ２４ ) ２ O ２／２ Q ３ =Si(OR ２５ ) ３ O １／２ Q ４ =Si(OR ２６ ) ４ Q ５ =SiO ４／２ Here: a, b, c, d, e, f, g, h, i, j, k, l, o, and p are zero or any positive integer, subject to the following constraints: 1≦[a+b+c+d+e+f+g+h+i+j+k+l+o+p]≦6000; [b+e+h+k]≧1; R ５ , R ６ , R ７ , R ９ , R １０ , R １２ , R １３ , R １４ , R １５ , R １７ , R １９ , and R ２０ Each of these is independently selected from hydrogen, C1-C60 alkyl, C6-C60 aromatic-containing group, C1-C10 alkoxy, and hydroxyl; R ８ , R １６ , R ２１ , and R ２４ Each is independently selected from the monovalent hydrophilic groups of the following equation, where G≧0: 【Transformation 30】 Here, A is a crosslinking unit between the siloxane moiety and the hydrophilic group I, having at least one spacer atom selected from C1-C60 acyclic hydrocarbon radicals, C4-C60 alicyclic radicals, C6-C60 aromatic hydrocarbon radicals, polyetheramines, polyethers, polyamides, polyesters, polyurethanes, polysulfones, polycarbonates, or two or more combinations thereof, where the crosslinking unit may contain one or more parts selected from alkoxys, carboxyls, urethanes, ureas, ketones, or two or more combinations thereof; I is an ionic group, an ionizable group, an amphoteric group, or a polar hydrophilic group; G is a polymerizable group having the following general formula: 【Chemistry 31】 A nonpolymerizable group of formula F-K, where F is a linking group selected from C1-C60 acyclic hydrocarbon radicals, C4-C60 alicyclic radicals, C6-C60 aromatic hydrocarbon radicals, polyetheramines, polyethers, polyamides, polyesters, polyurethanes, polysulfones, polycarbonates, or two or more combinations thereof, where the crosslinking group may include one or more parts selected from alkoxys, carboxyls, urethanes, ureas, ketones, or two or more combinations thereof; R ２７ , R ２８ , and R ２９ These are independently selected from hydrogen or a monovalent hydrocarbon radical with 1 to 5 carbon atoms, and K is independently selected from hydrogen, C1-C60 acyclic hydrocarbon radicals, C4-C60 alicyclic radicals, C6-C60 aromatic hydrocarbon radicals, epoxy groups, or ether groups; R １１ , R １８ , and R ２２ Each is independently selected from bases A-G, where A and G are as described above; and R ２３ , R ２５ , and R ２６ is R ５ From R ２２ You can independently choose any one of these or any combination thereof. The composition according to claim 8 or 9.

11. Siloxanes containing hydrophilic groups are given by formula M １ ａ M ２ ｂ M ３ ｃ Q ５ ｐ The composition of claim 10, wherein b is ≥ 1.

12. I is carboxylate-COO － , dicarboxylate (-R(COO-) ２ ), sulfone-SO ２ -, sulfonate-SO ３ － Sulfate-OSO ３ － , phosphonate-PO ３ ２－ phosphate-OPO ３ ２－ Group, -N ＋ R ３０ R ３１ H, -N ＋ H ２ R ３２ , -N ＋ H ３ Selected from , or ammonium salts, each comprising a cation independently selected from hydrogen or alkali metals, alkaline earth metals, transition metals, quaternary ammonium groups, and phosphonium groups, where R ３０ , R ３１ , and R ３２ The composition of claim 10 or 11, wherein is independently selected from C1 to C30 hydrocarbons.

13. I is equation -R ３３ -N ＋ (R ３４ ) ２ -R ３５ -I ｚ A group having R is selected, where R ３３ R is a divalent hydrocarbon group having 1 to 20 carbon atoms. ３４ R is a monovalent hydrocarbon group having 1 to 20 carbon atoms. ３５ is a divalent hydrocarbon group having 2 to 20 carbon atoms; and I ｚ is carboxylate-COO － , sulfone-SO ２ -, sulfonate-SO ３ － Sulfate-OSO ３ － , phosphonate-PO ３ ２－ , and phosphate-OPO ３ ２－ The composition of claim 10 or 11, wherein the ionic group is selected from the group.

14. The composition of claim 10 or 11, wherein I is a polar group selected from polyetheramine, polyether, polyamide, polyester, polyurethane, polysulfone, and / or polycarbonate.

15. The hydrophilic group is a polyetheramine group selected from the following compounds: R ３６ -(O-R ３７ -) ｑ -NH ２ In the formula R ３６ R is selected from C1 to C60 hydrocarbons, ３７ The composition of claim 10 or 11, wherein is selected from C1 to C60 hydrocarbons and q is ≥ 1.

16. Polyetheramines are selected from the following compounds: R ３６ -(O-CH ２ CH ２ ) ｘ -(O-CCH ２ CH ２ CH ２ ) ｙ -(OCH ２ CH ２ CH(CH ３ )) ｚ -NH ２ The composition of claim 15, wherein x, y, and z are independently from 0 to about 300, where x + y + z ≥ 2.

17. The polyetheramine group is selected by the following general formula: 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 The composition of claim 9, 10, 15, or 16.

18. The composition according to any one of claims 8 to 17, wherein the hydrophilic group-containing siloxane (iii) is present in an amount of about 0.1% to about 20% by weight based on the total weight of the composition.

19. The composition according to any one of claims 8 to 18, wherein the hydrophilic group-containing siloxane (iii) is present in an amount of about 1.5% to about 8% by weight based on the total weight of the composition.

20. A pressure-sensitive adhesive formed from any composition of claims 8 to 18.

21. The pressure-sensitive adhesive of claim 20, wherein the adhesive has less than 2,500 ppm of one or more of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and / or dodecamethylcyclohexasiloxane.

22. The pressure-sensitive adhesive of claim 20, wherein the adhesive comprises less than 1000 ppm of one or more of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and / or dodecamethylcyclohexasiloxane.

23. The pressure-sensitive adhesive of claim 20, wherein the adhesive comprises less than 500 ppm of one or more of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and / or dodecamethylcyclohexasiloxane.

24. The pressure-sensitive adhesive of claim 20, wherein the adhesive comprises less than 100 ppm of one or more of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and / or dodecamethylcyclohexasiloxane.

25. An article comprising a pressure-sensitive adhesive according to any one of claims 20 to 24.

26. The article according to claim 25, selected from wound dressings, scar reduction dressings, drug delivery devices, medical tubes, clinical surfaces, pacemaker leads, wound healing patches, wound management devices, catheters, shunts, valves, stents, percutaneous patches, tissue engineering scaffolds, antimicrobial devices, ophthalmic devices, bioinserts, plugs, surgical devices, respiratory support devices, prosthetic devices, reconstructive devices, or implants.

27. The article of claim 25, selected from creams, lotions, bioactive compounds, deodorants, insecticides, cosmetic cosmetics, lipsticks, eyeshadows, stage makeup, hand cleaners, face masks, pore cleansers, knee or elbow protectors, bras, surgical gowns, nasal patches, prosthetics, cooling wraps, heat wraps, hearing aids, protective face masks, anti-snoring patches, jewelry, earrings, ornaments, tattoos, eyewear, tapes, or bandages.

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