Organogel pressure-sensitive adhesive for gentle release and long wear

Abstract

Organogel pressure-sensitive adhesives, compositions for preparing pressure-sensitive adhesives, and medical articles having organogel pressure-sensitive adhesives are described. Also described are methods for preparing organogel pressure-sensitive adhesives, methods for preparing medical articles having organogel pressure-sensitive adhesives, methods of using medical articles, and kits.

Description

PA200172WO02ORGANOGEL PRESSURE-SENSITIVE ADHESIVE FOR GENTLE RELEASE AND LONG WEARBACKGROUND

[0001] Medical adhesive-related injury (“MARSI”) is an occurrence in which erythema or other cutaneous abnormality (e.g., vesicle, bulla, erosion, or tear) persists 30 minutes or more after removal of an adhesive. Skin injuries relating to medical adhesives are prevalent, yet an under-recognized complication. Stripping is one mode of MARSI in which at least part of the epidermis remains attached to the adhesive when the adhesive is removed, resulting in epidermal damage and exposed dermis. Skin condition, adhesive characteristics, frequency of contact with the adhesive, and overall application and removal technique can all contribute to outcomes of MARSI.

[0002] Pressure-sensitive adhesives (“PSA”) are the most common type of adhesive for use on skin. They are self-stick adhesives that form a bond when pressure is applied to the adhesive in contact with a surface. Most medical PSAs are acrylic / acrylate-based or silicone-based. MARSI is more common with acrylic / acrylate PSAs than it is with silicone PSAs. However, silicone PSAs are much more expensive, require exotic processing, and compatible release liners require polyfluoroalkyl substances (“PF AS”).

[0003] What is needed are acrylic / acrylate-based pressure-sensitive adhesives that are less likely to cause MARSI. This need is satisfied with the organogel PSAs of the present disclosure.SUMMARY

[0004] In one embodiment, an organogel pressure-sensitive adhesive is described. The organogel pressure-sensitive adhesive includes a non-crosslinked acrylate polymer characterized by a glass transition temperature of at least -70 °C; at least one hydrocarbon compound; and a plasticizer characterized by an HLB value of no greater 5, a molecular weight of at least 400 Da, and a glass transition temperature of less than 0 °C. The non-crosslinked acrylate polymer is derived from one or more alkyl (alk)acrylate characterized by a homopolymer glass transition temperature of about -100 °C to about -25 °C, and one or more polar monomer characterized by a homopolymer glass transition temperature of at least 0 °C, wherein the one or more polar monomer is present within the non-crosslinked acrylate polymer in an amount of at least 20 mol% based on the total molar amount of the non-crosslinked acrylate polymer. At least 60 wt% of components of the organogel pressure-sensitive adhesive (excluding any solvents) are characterized as liquids at 25 °C at lOlkPa.

[0005] In one embodiment, a composition for preparing an organogel pressure-sensitive adhesive of the present disclosure is described. The composition includes one or more volatile solvent; the non-crosslinked acrylate polymer; the at least one hydrocarbon compound; the plasticizer; and optionally a tackifier.

[0006] In one embodiment, a composition for preparing an organogel pressure-sensitive adhesive of the present disclosure is described. The composition includes the one or more alkyl (alk)acrylate monomer; the one or more polar monomer; the at least one hydrocarbon compound; the plasticizer; and optionally a tackifier.

[0007] In one embodiment, a medical article is described. The medical article includes a substrate and an organogel pressure-sensitive adhesive of the present disclosure.

[0008] In one embodiment, a method for preparing an organogel pressure-sensitive adhesive of the present disclosure is described. The method includes providing a composition having: an acrylate polymer prepared from the one or more alkyl (alk)acrylate monomer and the one or more polar monomer, the at least one hydrocarbon compound, the plasticizer, and optionally a tackifier.

[0009] In one embodiment, a method for preparing an organogel pressure -sensitive adhesive of the present disclosure is described. The method includes providing a composition having: the one or more alkyl (alk)acrylate monomer, the one or more polar monomer, the at least one hydrocarbon compound, the plasticizer, and optionally a tackifier. The method further includes subjecting the composition to conditions effective to polymerize the one or more alkyl (alk)acrylate monomer and the one or more polar monomer.

[0010] In one embodiment, a solvent-cast method for preparing a medical article of the present disclosure is described. The solvent-case method includes providing a substrate and a composition having one or more volatile solvent and an organogel pressure-sensitive adhesive of the present disclosure. The solvent-case method further includes contacting the composition to the substrate; and removing the one of more volatile solvent to form the medical article.

[0011] In one embodiment, a hot-melt method for preparing a medical article of the present disclosure is described. The hot-melt method includes providing a substrate and an organogel pressuresensitive adhesive of the present disclosure; heating the organogel pressure-sensitive adhesive to form a heated pressure-sensitive adhesive; and contacting the heated pressure-sensitive adhesive to the substrate to form the medical article.

[0012] In one embodiment, a method of adhering a medical article of the present disclosure to a skin surface of a subject is described. The method includes contacting the organogel pressure-sensitive adhesive of the medical article to the skin surface of the subject.

[0013] In one embodiment, a kit is described. The kit includes a medical article of the present disclosure and a set of instructions directing a user to contact the medical article to a skin surface.

[0014] In one embodiment, a kit is described. The kit includes a composition for preparing an organogel pressure-sensitive adhesive of the present disclosure and a set of instructions directing a user to prepare a medical article.DETAILED DESCRIPTION

[0015] The acrylate-based organogel PSAs of the present disclosure have adhesive strengths and long wear times that are comparable to standard, non-organogel acrylic / acrylate-based PSAs, yet the organogel adhesives are much gentler on the skin to remove.

[0016] Standard acrylic / acrylate-based PSAs are relatively viscous and do not immediately flow into the fine structures of skin. Consequently, standard PSAs increase in adhesion over time as skin crevices become filled. Suboptimal initial adhesion is typically offset by incorporating tackifiers into the PSA compositions; however, it is believed that the magnitude of final adhesion is destructive to skin. Standard acrylic / acrylate-based PSAs strip skin cells upon removal of the adhesive, and it for this reason that they cannot be re-applied because the adhesive surface is coated with skin cells.

[0017] The organogel PSAs of the present disclosure do not lack initial adhesion nor do they increase in adhesion over time like standard PSAs. It is believed that the organogel nature (i.e., high liquid content) of the present PSAs allows for the polymer to uniformly coat the skin surface and immediately flow into the fine structures of the skin. Thus, the need for tackifiers is eliminated. Surprisingly, the organogel PSAs do not remove skin cells despite readily flowing into skin crevices. Thus, the organogel PSAs may be removed and re-applied several times without compromising adhesion. A mechanistic explanation for this property is presently unclear.

[0018] Additionally, the hydrocarbon compound(s) (i.e., liquid content) of the organogel PSAs appears to serve as an occlusive barrier. The organogel PSAs do not lose adhesion in the presence of water or other aqueous fluids. Thus, patients wearing the organogel PSAs may bathe without concern that water will reduce wear time or otherwise penetrate the article and possibly lead to water-based skin injuries. In contrast, hydrogel acrylic / acrylate-based PSAs readily swell when exposed to aqueous fluids resulting in poor length of wear. Like the organogel PSAs of the present disclosure, the concept of hydrogel PSAs were an attractive endeavor for solving problems associated with standard aery lic / acry late PSAs. Namely, the increased flowability of gels allowing for faster adhesion. Hydrogel PSAs also suffer from drying out since water in the hydrogel is the crosslinking agent (via hydrogen bonding) that gives the PSA cohesion. Thus, hydrogel PSAs lose adhesion if the water content is not maintained at optimal levels. The organogel PSAs solve the problems associated with both hydrogel PSAs and standard PSAs.

[0019] The organogels of the present disclosure are not largely dominated by a solids fraction, like standard acrylic / acrylate-based adhesives. Standard acrylic / acrylate-based adhesives typically have about 60-100 wt% of an acrylic / acrylate polymer(s), which are generally solids at 25 °C at 101 kPa. Tackified standard acrylic / acrylate-based adhesives typically have up to about 40 wt% tackifier(s), wherein suitable tackifiers for acrylic / acrylate polymers are also generally solids at 25 °C at 101 kPa. Plasticizers are employed to soften solid-dominated adhesive compositions to achieve a flowableconsistency. Suitable plasticizers are typically liquids at 25 °C at 101 kPa and are present in an amount of up to 40 wt%. Standard acrylic / acrylate-based adhesives having both tackifier and plasticizer typically have no less than 60 wt% of an acrylic / acrylate polymer. Efforts to reduce the amount of acrylic / acrylate polymer often results in adhesives that lose cohesion and become gooey. In contrast, the present disclosure demonstrates that organogels, which have a dominant liquid fraction, can have exceptional cohesion and adhesion despite having a relatively low amount acrylate-based polymer (e.g., 25-40 wt%). Organogels without tackifier may have a % solids value that is equivalent to the amount of acrylate-based polymer present. Conversely, organogels with a tackifier may have a % solids value of less than 60%.

[0020] Interestingly, the nature of these organogels allows for pressure-sensitive adhesives to be made via hot-melt processing (no solvent involved). Typically, standard acrylic / acrylate-based adhesives are too viscous to undergo hot-melt processing and must be made via solvent-casting. The ability to hot-melt process acrylate-based pressure-sensitive adhesives, due to this novel organogel form, will greatly improve manufacturing and reduce waste.

[0021] Organogel acrylic / acrylate PSA formulations were not known prior the present disclosure, let alone organogel PSAs that offer a hydrophobic occlusive barrier, fast adhesion, extended wear, complete debonding and re-positioning / re-application capabilities, and that, most importantly, avoid MARSI. An organogel PSA was a foreign concept until now since liquid hydrocarbon compounds are not miscible with typical acrylic / acrylate polymers (i.e., acrylic / acrylate polymers void of hydrophobic units, e.g., > Cs pendant groups). The present disclosure details that the hydrocarbon compounds can be solubilized in such acrylic / acrylate polymers with a suitable plasticizer. Stability of the composition is important because adhesion is lost if phase separation occurs. Surprisingly, the present disclosure also demonstrates that antimicrobial agents (e.g., quaternary ammonium salts) that are not soluble in these hydrocarbon compounds or soluble in acrylic / acrylate polymers can be solubilized within the organogel PSAs of the present disclosure, which is also likely due to the presence of the plasticizer. Perhaps even more surprising is that the organogel PSAs of the present disclosure do not appear to be detrimentally affected by sterilization processes involving gamma irradiation.

[0022] Furthermore, it has been discovered that there is no need to crosslink the acrylic / acrylate polymers if at least 20 wt% polar monomer (as described herein) is incorporated within the polymer. In other words, at least 20 wt% of polar monomer provides for adequate stiffness in the resulting PSA. Less than 20 wt% polar monomer, on the other hand, requires crosslinking. Foregoing the need to crosslink organogels further improves manufacturing and cost efficiency.Definitions

[0023] As used herein, “about” means ± 10 percent of a given value. For example, about 10 means 9 to 11.

[0024] As used herein, “acrylate” refers to a compound having at least one moiety represented by: -O(CO)-C(Rb)=C(Rc)2. The term “methacrylate” means Rbis -CH3. The term “(meth)acrylate” means Rbcan be -H or -CH3. The term alkyl (alk)acrylate means Ra-O(CO)-C(Rb)=C(Rc)2 wherein Raand Rbare each alkyl-based, e.g., alkyl, cycloalkyl, alkcycloalkyl, or the like. As used herein, “acrylic” refers to a compound in which Rais hydrogen. An acrylate polymer describes a compound derived at least from acrylate monomers. An acrylic polymer describes a polymer derived at least from acrylic monomers. An acrylic / acrylate polymer describes a polymer derived at least from acrylic monomers, acrylate monomers, or a combination thereof.

[0025] As used herein, “alkaryl” means a bivalent alkylene group terminated with an aryl group. An alkaryl may be represented as follows: -alkylene-aryl. For example, a C7 alkaryl group may be benzyl, i.e., -CH2PI1.

[0026] As used herein, “alkaralkyl” means a bivalent alkylene group bonded to a bivalent arylene group, which in turn is bonded to a monovalent alkyl group. An alkaralkyl is represented as follows: -alkylene-arylene-alkyl.

[0027] As used herein, “alkcycloalkyl” means a bivalent alkylene group bonded to a cycloalkane. “Alkcycloalkylene” means a bivalent alkylene group bonded to a bivalent cycloalkyl group. “ Alkcycloalkenylene” means a bivalent alkylene group bonded to a bivalent cycloalkene group.

[0028] As used herein, “alkenyl” means a monovalent unsaturated hydrocarbon chain having one or more alkene (i.e., -C(Ra)=C(Ra)2), wherein Rais -H, alkyl, alkenyl, or a substituent as indicated). The unsaturated hydrocarbon chain may be straight or branched as indicated. As used herein, “alkenylene” means a bivalent (i.e., -C(Ra)=C(Ra)-), unsaturated hydrocarbon chain having one or more alkene, straight or branched as indicated. As used herein, “olefin” is synonymous with alkene.

[0029] As used herein, “alkoxy” means a monovalent saturated hydrocarbon chain having one or more oxygen atoms intercepting the hydrocarbon chain. For example, a C3 alkoxy includes -CH2CH2-O-CH3, or the like; a C4 alkoxy includes -CH2CH2-O-CH2CH3, or the like; a Cs alkoxy includes -CH2CH2-O-CH2CH2CH3, -CH2CH2-O-CH2CH2-O-CH3, or the like. The term “alkoxy” does not encompass groups terminating with -OH - such groups are referred to herein as “alkoxylate,” e.g., -CH2CH2-O-CH2CH2-OH. The term “alkoxylene” means a bivalent alkoxy group, e.g., -CH2CH2-O-CH2-, -CH2CH2-O-CH2CH2-O-CH2CH2-, or the like.

[0030] As used herein, “alkyl” means a monovalent saturated hydrocarbon chain, straight or branched as indicated. For example, straight Ci-6 alkyl includes Ci alkyl (i.e., methyl), a C2 alkyl (i.e., ethyl), C3 alkyl (i.e., propyl –(CH₂)₂CH₃, C4 alkyl (e.g., butyl –(CH₂)₃CH₃, C5 alkyl (i.e., pentyl -(CH2)4CH3), or C₆ (i.e., hexyl –(CH₂)₅CH₃). For example, a branched C3-6 alkyl includes C3 alkyl (i.e., isopropyl -CH(CH3)2), C4 alkyl (e.g., sec-butyl -CH(CH3)CH2CH3), C5 alkyl (e.g., neopentyl -CH2C(CH3)3). An “alkylene” means a bivalent saturated hydrocarbon chain, straight or branched asindicated. For example, a C2 alkylene is ethylene, i.e., -CH2CH2-; a C3 alkylene is propylene, i.e., -CH2CH2CH2- or isopropylene, i.e., -CH(CH3)CH2-.

[0031] As used herein, “aryl” describes an aromatic group that is free of heteroatoms (e.g., N, O, S) within the ring. An aromatic group is cyclic, planar, fully conjugated, and follows Huckle’s Rule (i.e., having 4n + 2 ^-electrons, wherein n is an integer). For example, phenyl is a Cg aryl, naphthyl and azulenyl are C10 aiyls, and anthracenyl and phenanthrenyl are C14 aiyls. As used herein, “arylene” describes a bivalent aryl group. For example, a Cg arylene is phenylene, i.e., -Ph-, the connectivity may be ortho, meta, or para, unless otherwise as indicated.

[0032] As used herein, the expression “Cx-Cy” or“Cx” or“> Cx”, wherein X, Y are integers, denotes the total number of carbon atoms or range of carbon atoms within a particular group.

[0033] As used herein, “cycloalkyl” describes a monovalent saturated cycloaliphatic group. For example, a C5.6 cycloalkyl group includes C5 cycloalkyl (i.e., cyclopentyl -C5H9) and Cg cycloalkyl (i.e., cyclohexyl -CgHn). A “cycloalkylene” is a bivalent saturated cycloaliphatic group. For example, a Cs- cycloalkylene group includes Cs cycloalkylene (i.e., cyclopentylene -CsHs-) and Cg cycloalkylene (i.e., cyclohexylene -CgHio-), including all modes of connectivity (e.g., 1,2-, 1,3-, or the like) unless otherwise indicated. As used herein, an “alkcycloalkyl” describes a bivalent alkylene group terminated with a cycloalkyl group.

[0034] As used herein, “cross-linked” means at least two compounds (e.g., polymers) are covalently joined together by a connecting bond, a connecting atom, or connecting group of atoms. As used herein, “cross-linked” does not encompass ionic bonding. As used herein, “non-crosslinked” means that no two compounds (e.g., polymers) are covalently joined together by a connecting bond, a connecting atom, or a connecting group of atoms. The non-crosslinked acrylate polymers of the present disclosure have not been subjected to e-beam irradiation or subjected to UV irradiation post polymerization.

[0035] As used herein, “exclude” means that the referenced substance is not present, i.e., 0 wt.%.

[0036] As used herein, “di(alk)acrylate monomer" means a compound having two (alk)acrylate units. Likewise, “tri(alk)acrylate monomer” means a compound having three (alk)acrylate units.

[0037] As used herein, “glass transition temperature” or “Tg” means the temperature or range of temperatures at which materials transition from a hard state to a viscous or rubbery state. As used herein, “homopolymer glass transition temperature” is used to characterize monomers by way of their homopolymer. The recited values herein are widely quoted in the literature.

[0038] As used herein, “hydrophilic-lipophilic balance” or “HLB” values are calculated using the method of Griffin (Griffin WC; J. Soc. of Cosmetic Chemists 5, 259 (1954)). The HLB Method used herein involves a calculation based on the following:HLB = 20*Mh / Mwherein Mh is the molecular mass of the hydrophilic portion of the molecule and M is the molecular mass of the whole molecule.

[0039] As used herein, “the hydrocarbon compound” is defined as a hydrocarbon consisting strictly of carbon and hydrogen atoms, i.e., no heteroatom functional groups, e.g., O, N, S, or the like.

[0040] As used herein, ''monomer" means a compound having at least one functional group (e.g., alkenes, alkynes, and the like) known to participate in polymerization reactions (e.g., radical polymerizations, cationic polymerizations, and the like).

[0041] As used herein, “A-vinyl lactam monomer” refers to a lactam moiety having a vinyl group directly attached to a nitrogen (i.e., -N-CH=CH2) within a lactam ring system. A lactam is a cycloaliphatic system having an amide (i.e., -NR-C(O)-) within the ring atoms.

[0042] As used herein, the phrase “one or more of’ such as used in the phrase “one or more of A and B” or “one or more of at least one A and at least one B” means a composition may include at least one A, more than one A, at least one B, more than one B, at least one A and at least one B, more than one A and more than one B. In other words, the phrase does not mean the composition must have at least one of each of A and B.

[0043] As used herein, “octanol-water partition coefficient” (Log P) is a partition coefficient for the two-phase system of octanol and water. It serves as a measure of the relationship between lipophilicity and hydrophilicity substance. Lipophilic substances have greater solubility in the octanol portion of the two-phase system and are represented by greater Log P values. Substances that are more hydrophilic have smaller Log P values and negative Log P values. Octanol-water partition coefficients may be measured or may be estimated, for example, via quantitative structure-activity relationships (QSAR) or linear free energy relationships (LFER). Log P values for known monomers can be found in the literature. As used herein, Log P values greater than 1 are denoted as “non-polar,” whereas Log P values less than 1 are denoted as “polar.”

[0044] As used herein, the phrase, “optionally substituted” when characterizing a chemical group, means that the chemical group may or may not be substituted with the subsequent group(s), i.e., a hydrogen is replaced with the listed group. It should be noted that the chemical groups identified herein are unsubstituted unless stated otherwise.

[0045] As used herein, “organogel” describes a class of gel composed of an organic liquid phase within a three-dimensional network involving polymer chains.

[0046] As used herein, “organic” defines a compound having carbon, whereas “inorganic” defines a compound without carbon. An “organic phase” includes all organic compounds. An “inorganic phase” includes all inorganic compounds.

[0047] As used herein, “pendant” refers to atoms or groups of atoms of a polymer that are not within the linear chain of polymerization.

[0048] As used herein, “polar” is a term to characterize a compound (e.g., monomer) having an octanol-water partition coefficient of less than 1.0. “Polar” may be used synonymously with “hydrophilic” herein. Conversely, “non-polar” is a term to characterize a compound having an octanolwater partition coefficient of greater than 1.

[0049] As used herein, “polycyclic aromatic hydrocarbon” means a compound with at least one aromatic ring (i.e., following Huckel’s rule: a cyclic, planar ring with 4n+27t electrons) and at least one additional ring (cycloaliphatic or aromatic) fused (i.e., sharing two atoms) to the at least one aromatic ring.

[0050] As used herein, “plasticizer” refers to a substance that is added to a material to make it softer, increase flexibility, increase plasticity, reduce viscosity, and / or decrease friction. Plasticizers have relatively low glass transition temperatures and thereby lower the glass transition temperature of the material when combined with said material.

[0051] As used herein, “pressure-sensitive adhesive” is a type of nonreactive adhesive that forms a bond when pressure is applied to adhesive in contact with a surface.

[0052] Regarding ratios: the order of the ratios correlates to the order in which the components appear in the preceding text. For example, component A and component B are present in a weight ratio of about A: B to about A: B, never B: A.

[0053] As used herein, “resin” describes solid or highly viscous substances of plant or synthetic origin that are typically polymerizable.

[0054] As used herein, “rosin” describes solidified resins from which volatile components have been removed by distillation.

[0055] As used herein, “self-priming” refers to the hydrophobic occlusive barrier that forms at between the PSA and a surface (e.g., skin) due to the presence of the at least one hydrocarbon compound described herein.

[0056] As used herein, “soluble” refers to at least 1 g of a component A completely dissolved (no visible cloudiness, precipitate, or phase separation) in 30 mL or less component B (e.g., acrylate polymer and plasticizer) at a temperature range of about 20 °C to about 23 °C and at atmospheric pressure (i.e., 760 mm / Hg). It is to be understood that the conditions to determine solubility only include the component A and the component B, i.e., no added salts, or the like.

[0057] As used herein, “solvent” refers to any volatile compound having a vapor pressure greater than 0.3 kPa at 20 °C.

[0058] As used herein, “tackifier” refers to a substance that is added to a material to increase tack. Tackifers have relatively high glass transition temperatures and thereby increase the glass transition temperature of a material when combined with said material. Tackifiers also decrease the modulus and allow for better flow of said material.

[0059] As used herein, “viscosity” is a property measured using a ThermoHaake Rotovisco 1 device with a plate / plate system (diameter 20 mm) and a slit of 0.2 mm. The viscosity values for each shear rate (e.g., 10 1 / s to 100 1 / s in 10 1 / s steps), with a delay of 5 seconds before collecting data. This method of measurement corresponds to DIN 53018-1. The viscosity values described herein are reported at 20 °C at a shear rate of 1 / s, unless otherwise stated.

[0060] As used herein, “volatile” defines a substance that evaporates at normal temperatures. Volatile substances, such as the solvents described herein, are characterized herein as having a vapor pressure of at least 0.3 kPa at 20 °C.PRESSURE SENSITIVE ADHESIVES

[0061] In various embodiments, an organogel pressure-sensitive adhesive is described. The organogel pressure-sensitive adhesive may include a non-crosslinked acrylate polymer characterized by a glass transition temperature of at least -70 °C; at least one hydrocarbon compound; and a plasticizer characterized by an HLB value of no greater 5, a molecular weight of at least 400 Da, and a glass transition temperature of less than 0 °C. The non-crosslinked acrylate polymer may be derived from one or more alkyl (alk)acrylate characterized by a homopolymer glass transition temperature of about -100 °C to about -25 °C, and one or more polar monomer characterized by a homopolymer glass transition temperature of at least 0 °C, wherein the one or more polar monomer may be present within the non-crosslinked acrylate polymer in an amount of at least 20 mol% based on the total molar amount of the non-crosslinked acrylate polymer. At least 60 wt% of components of the organogel pressuresensitive adhesive (excluding any solvents) may be characterized as liquids at 25 °C at lOlkPa.

[0062] In several embodiments, an organogel pressure-sensitive adhesive is described. The organogel pressure-sensitive adhesive may include a non-crosslinked acrylate polymer characterized by a glass transition temperature of at least -70 °C; at least one hydrocarbon compound; and a plasticizer characterized by an HLB value of no greater than 5, a molecular weight of at least 400 Da, and a glass transition temperature of less than 0 °C. The non-crosslinked acrylate polymer may be derived from one or more alkyl (alk)acrylate characterized by a homopolymer glass transition temperature of about -100 °C to about -25 °C, and one or more polar monomer characterized by a homopolymer glass transition temperature of at least 0 °C. At least 60 wt% of components of the organogel pressuresensitive adhesive (excluding any solvents) are characterized as liquids at 25 °C at lOlkPa.

[0063] In several embodiments, an organogel pressure-sensitive adhesive is described. The organogel pressure-sensitive adhesive may include a non-crosslinked acrylate polymer characterized by a glass transition temperature of at least -70 °C; at least one hydrocarbon compound; and a plasticizer characterized by an HLB value of no greater than 5, a molecular weight of at least 400 Da, and a glass transition temperature of less than 0 °C. The non-crosslinked acrylate polymer may be derived from one or more alkyl (alk)acrylate characterized by a homopolymer glass transition temperature of about -100 °C to about -25 °C, and one or more polar monomer characterized by a homopolymer glasstransition temperature of at least 0 °C. At least 60 wt% of components of the organogel pressuresensitive adhesive (excluding any solvents) are characterized as liquids at 25 °C at lOlkPa.

[0064] In many embodiments, the organogel pressure-sensitive adhesives of the present disclosure may exclude cross-linked acrylate polymers (e.g., acrylate polymers having been exposed to E-beam irradiation, acrylate polymers crosslinked via a crosslinking group within the polymer, and acrylate polymers crosslinked by reaction with a crosslinking compound).

[0065] Aspects of the non-crosslinked acrylate polymer(s), the hydrocarbon compound(s), and the plasticizer(s) are discussed in more detail below.

[0066] In some embodiments, the organogel pressure-sensitive adhesive may further include a tackifier. Tackifiers are discussed in more detail below.

[0067] In some embodiments, the organogel pressure-sensitive adhesive may further include one or more antimicrobial agent. Suitable antimicrobial agents may be inorganic or organic compounds. Inorganic antimicrobial agents include, for example, zinc salts (e.g., zinc oxide), silver salts, or the like. Organic antimicrobial agents include, for example, quaternary ammonium salts, (e.g., alkonium salts, benzalkonium salts, benzethonium salts, pyridinium salts). Antimicrobial agents are discussed in more detail below.

[0068] In many embodiments, the organogel pressure-sensitive adhesives are hydrophobic and not miscible with, or otherwise soluble, in water.

[0069] In many embodiments, the organogel pressure-sensitive adhesive may exclude additional polymers (other than those defined herein for the non-crosslinked acrylate polymer, hydrocarbon compound, plasticizer, and / or tackifier). Example polymers that may be excluded include, but are not limited to, acrylate polymers characterized by a Tgof less than -70 °C, rubber-based adhesive polymers such as styrene-butadiene-styrene, silicone polymers, thickening agents such as celluloses. Thickening agents such as silicates, diatomaceous earth, and kaolin clays may also be excluded.

[0070] In some embodiments, the organogel pressure-sensitive adhesive may further include a silicone polymer characterized by a viscosity no greater than 1000 cSt. For example, the organogel pressure-sensitive adhesive may further include a silicone polymer characterized by a viscosity (cSt) of about 5, 10, 15, 20, 25, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400, 500, 600, 700, 800, 900, or 1000, or a value within a range between any of the preceding values, e.g., between about 10 and about 30, between about 20 and about 50, or the like. In some embodiments, the pressure sensitive adhesive may only include silicone polymers characterized by a viscosity of less than 500 cSt. In some embodiments, the silicone polymer may be present in the organogel pressure-sensitive adhesive in an amount of about 1 wt% to about 35 wt%. For example, the silicone polymer may be present in the organogel pressuresensitive adhesive in an amount (wt%) of about 1, 2, 5, 8, 10, 12, 15, 18, 20, 22, 25, 28, 30, 32, or 35, or a value within a range between any of the preceding values, e.g., between about 15 and about 20,between about 10 and about 30, or the like. Example silicone polymers include, but are not limited to, phenyl trimethicone.

[0071] In some embodiments, the organogel pressure-sensitive adhesive may exclude other nonvolatile organic liquids and solids such as phthalates, adipate and sebacate esters, polyols such as ethylene glycol and glycerol, monoacylglycerides, triglyceride oils, tricresol phosphate, hydrocarbon compounds having heteroatom functional groups such as functionalized olefinic polymers, ethoxylated surfactants, poly ethers, and the like.

[0072] In some embodiments, the organogel pressure-sensitive adhesive may include at least 60 wt% of the components being liquids at 25 °C at 10 IkPa (excluding volatile solvents, i.e., any presence of volatile solvents are not included within the at least 60 wt%). For example, the organogel pressuresensitive adhesive may be comprised of components characterized as liquids in an amount (wt%) of about 60, 62, 65, 68, 70, 72, 75, 78, or 80, or a value within a range between any of the preceding values, e.g., between about 60 and about 70, between about 65 and about 80, or the like. In some embodiments, the organogel pressure-sensitive adhesive may include at least 20 wt% of the components being solids at 25 °C at lOlkPa. For example, the organogel pressure-sensitive adhesive may be comprised of components characterized as solids in an amount (wt%) of about 20, 22, 25, 28, 30, 32, 35, 38, or 40, or a value within a range between any of the preceding values, e.g., between about 20 and about 30, between about 25 and about 35, or the like. In some embodiments, the organogel pressuresensitive adhesive may be comprised of about 60 wt% to about 80 wt% liquid components and about 20 wt% to about 40 wt% solid components.

[0073] In many embodiments, the organogel pressure-sensitive adhesive may include volatile solvents, e.g., xylenes, heptane, methyl ethyl ketone, and the like, in an amount of no more than 1 wt% (i.e., residual solvent). In many embodiments, the organogel pressure-sensitive adhesive may exclude volatile solvents.

[0074] In many embodiments, the organogel pressure-sensitive adhesive may be characterized by one or more of: a peak value, a debonding energy value, and a displacement value, as described below in the Examples. In some embodiments, the organogel pressure-sensitive adhesive may be characterized by a peak value of no greater than about 65 g, or no greater than 60 g. For example, the organogel pressure-sensitive adhesive may be characterized by a peak value (in g) of about 15, 18, 20, 22, 25, 28, 30, 32, 35, 38, 40, 42, 45, 48, 50, 52, 55, 58, 60, 62, or 65, or a value within a range between any of the preceding values, e.g., between about 30 and about 40, or the like. In some embodiments, the organogel pressure-sensitive adhesive may be characterized by a debonding energy value of no greater than about 20 g.s. For example, the organogel pressure-sensitive adhesive may be characterized by a debonding energy value (in g.s.) of about 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, or a value within a range between any of the preceding values, e.g., between about 10 and about 20, or the like. In some embodiments, the organogel pressure-sensitive adhesive may be characterized bydisplacement value of no greater than 1.1 mm, or no greater than 0.8 mm. For example, the organogel pressure-sensitive adhesive may be characterized by a displacement value (in mm) of about 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, or 1.1, or a value within a range between any of the preceding values, e.g., between about 0.5 and about 0.8, or the like.

[0075] In many embodiments, the organogel pressure-sensitive adhesive may be characterized by a viscosity of no greater than 30 Pa*s according to the Rheological Measurement described herein. In some embodiments, the organogel pressure-sensitive adhesive may be characterized by a viscosity of less than 20 Pa*s, less than 10 Pa*s, or less than 5 Pa*s. For example, the organogel pressure -sensitive adhesive may be characterized by a viscosity (Pa*s, Rheological Measurement herein) of about 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.2, 2.5, 2.8, 3.0, 3.5, 4.0, 4.5, 5.0, 6.0, 7.0, 8.0, 9.0, 10, 12, 15, 18, 20, 22, 25, 28, or 30, or a value within a range between any of the preceding values, e.g., between 1 Pa*s and 15 5 Pa*s, or the like.

[0076] Further details pertaining to the individual components of the organogel pressure-sensitive adhesives are provided below.Non-Crosslinked Acrylate Polymer

[0077] In some embodiments, the non-crosslinked acrylate polymer may be characterized by a glass transition temperature of about -70 °C to about 10 °C. For example, the non-crosslinked acrylate polymer may be characterized by a glass transition temperature (°C) of about -70, -65, -60, -55, -50, -45, -40, -35, -30, -25, -20, -15, -10, -5, 0, 5, or 10, or a value within a range between any of the preceding values, e.g., between about -50 and about 0, between about -30 and 5, or the like. In some embodiments, the non-crosslinked acrylate polymer may be characterized by a glass transition temperature of at least -70 °C, at least -60, at least -50, at least -40, at least -30, at least -20, or at least -10.

[0078] In some embodiments, the non-crosslinked acrylate polymer may be characterized by a molecular weight of about 1000 kDa to about 1500 kDa. For example, the non-crosslinked acrylate polymer may be characterized by a molecular weight (kDa) of about 1000, 1050, 1100, 1150, 1200, 1250, 1300, 1350, 1400, 1450, or 1500, or a value within a range between any of the preceding values, e.g., between 1000 and 1200, between 1100 and 1400, or the like.

[0079] In some embodiments, the non-crosslinked acrylate polymer may be characterized by an inherent viscosity (“IV”) of about 1.2 dL / g to about 2.0 dL / g. Inherent viscosity is an indirect measure of molecular weight and may be measured according to the methods within U. S. Pat. No. 6,245,838 (incorporated herein by reference in its entirety). For example, IV can be determined using a Cannon-Fenske #50 viscosimeter in a water bath controlled at 25 °C to measure the flow time of 10 mL ofpolymeric solution (i.e., 0.2 g non-crosslinked acrylate polymer in 100 mL ethyl acetate). For example, the non-crosslinked acrylate polymer may be characterized by an inherent viscosity (dL / g) of about 1.2, 1.25, 1.3, 1.35, 1.4, 1.45, 1.5, 1.55, 1.6, 1.65, 1.7, 1.75, 1.8, 1.85, 1.9, 1.95, or 2.0, or a value within a range between any of the preceding values, e.g., between about 1.4 and about 1.75, or the like.

[0080] In some embodiments, the non-crosslinked acrylate polymer may exclude having units derived from chain transfer agents. In many of such embodiments, the non-crosslinked acrylate polymer may be characterized by an inherent viscosity (“IV”) of about 1.2 dL / g to about 2.0 dL / g (or any range therebetween), despite not having units derived from chain transfer agents. However, in other embodiments, the non-crosslinked acrylate polymer may include units derived from chain transfer agents. In many of such embodiments, the non-crosslinked acrylate polymer may be characterized by an inherent viscosity of about 1.2 dL / g to about 2.0 dL / g (or any range therebetween), accounting for the presence and amount of units derived from chain transfer agents within the non-crosslinked acrylate polymer. Chain transfer agents are further described below.

[0081] In many embodiments, the non-crosslinked acrylate polymer may be present in an amount of about 20 wt% to about 50 wt% with respect to the weight of the organogel pressure-sensitive adhesive. For example, the non-crosslinked acrylate polymer may be present in the organogel pressuresensitive adhesive in an amount in wt% with respect to the weight of the non-crosslinked acrylate polymer of about 20, 2225, 28, 30, 33, 35, 37, 40, 42, 45, 48, or 50, or a value within a range between any of the preceding values, e.g., between about 25 and about 33, between about 25 and about 40, or the like. In some embodiments, the non-crosslinked acrylate polymer may be present in an amount of no more than 40 wt% with respect to the weight of the organogel pressure-sensitive adhesive.

[0082] In many embodiments, the non-crosslinked acrylate polymer may be present in the organogel pressure-sensitive adhesive in an amount relative to the hydrocarbon compound(s) at a weight ratio of about 0.5:1 to about 2.5:1. For example, the weight ratio of non-crosslinked acrylate polymer to hydrocarbon compound(s) (polymerhydrocarbon) may be about 0.5:1, 0.6:1, 0.7:1, 0.8:1, 0.9:1 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1, 1.9:1, 2:1, 2.1:1, 2.2:1, 2.3:1, 2.4:1, or 2.5:1, or a value within a range between any of the preceding values, e.g., between about 0.8:1 and about 1.2, between about 1:1 and about 1.5:1, or the like.

[0083] In many embodiments, the non-crosslinked acrylate polymer may be present in an amount relative to the plasticizer at a weight ratio of about 0.5:1 to about 2:1. For example, the weight ratio of the non-crosslinked acrylate polymer and the plasticizer (polymer:plasticizer) may be about 0.5:1, 0.6:1, 0.7:1, 0.8:1, 0.9:1 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1, 1.9:1, or 2:1, oravalue within a range between any of the preceding values, e.g., between about 0.8:1 and about 1.2, between about 1:1 and about 1.5:1, or the like.

[0084] In some embodiments, the non-crosslinked acrylate polymer may be present:in an amount of about 20 wt% to about 50 wt% (e.g., 25 wt% to 33 wt%) with respect to the weight of the organogel pressure-sensitive adhesive; andin a weight ratio relative to the hydrocarbon compound(s) of about 0.5:1 to about 2.5:1 (e.g., 0.8:1 to 1.2:1) (polymer: hydrocarbon)).

[0085] In some embodiments, the non-crosslinked acrylate polymer may be present:in an amount of about 20 wt% to about 50 wt% (e.g., 25 wt% to 33 wt%) with respect to the weight of the organogel pressure-sensitive adhesive; andin a weight ratio relative to a plasticizer(s) of about 0.5:1 to about 2:1 (e.g., 0.8:1 to 1.2:1) (polymerplasticizer)).

[0086] In some embodiments, the non-crosslinked acrylate polymer may be present:in an amount of about 20 wt% to about 50 wt% (e.g., 25 wt% to 33 wt%) with respect to the weight of the organogel pressure-sensitive adhesive;in a weight ratio relative to the hydrocarbon compound(s) of about 0.5:1 to about 2.5:1 (e.g., 0.8:1 to 1.2:1) (polymer: hydrocarbon)); andin a weight ratio relative to a plasticizer(s) of about 0.5:1 to about 2:1 (e.g., 0.8:1 to 1.2:1) (polymerplasticizer)).

[0087] In some embodiments, the non-crosslinked acrylate polymer may be derived only from the one or more alkyl (alk)acrylate monomer and the one or more polar monomer, as described herein. In other words, the non-crosslinked acrylate polymer may exclude units derived from monomers other than the one or more alkyl (alk)acrylate monomer and the one or more polar monomer, as described herein.

[0088] In some embodiments, the non-crosslinked acrylate polymer may be derived only from the one or more alkyl (alk)acrylate monomer and the one or more polar monomer, as described herein. In other words, the non-crosslinked acrylate polymer may exclude units derived from monomers other than the one or more alkyl (alk)acrylate monomer and the one or more polar monomer, as described herein.

[0089] In some embodiments, the non-crosslinked acrylate polymer may exclude being derived from monomers characterized by a homopolymer glass transition temperature of less than 0 °C that are not acrylate-based.

[0090] In some embodiments, the non-crosslinked acrylate polymer may exclude being derived from monomers having silicone-based functional groups. Likewise, the non-crosslinked acrylate polymer may exclude having any pendant silicone-based functional groups.

[0091] In some embodiments, the non-crosslinked acrylate polymer may exclude being derived from olefinic hydrocarbon monomers, e.g., ethylene, propylene, butene, butadiene, or the like, whether co-polymerized or through post-polymerized functionalization. Likewise, the non-crosslinked acrylatepolymer may exclude having any pendant hydrocarbon groups (e.g., > Ci2) derived from olefinic hydrocarbon monomers.

[0092] In some embodiments, the non-crosslinked acrylate polymer may exclude hydroxyl groups.

[0093] In some embodiments, the non-crosslinked acrylate polymer may exclude pendant ether groups (e.g., pendant > Cs ether groups). For example, the non-crosslinked acrylate polymer may exclude pendant ether groups of the formula: -X-O-Y, wherein X is a bond or an alkylene and Y is an alkyl. For example, X+Y may include 8, 10, 12, 15, 18, 20, 22, 25, 30, 35, 40, 45, or 50 carbon atoms, or more, or a value within a range between any of the preceding values, e.g., a C8-C20 ether group, or the like.Alkyl (Alk)Acrylate Monomers (Low Tg)

[0094] In some embodiments, each of the one or more alkyl (alk)acrylate monomer may be characterized by a homopolymer glass transition temperature of about -100 °C to about -25 °C. For example, the one or more alkyl (alk)acrylate monomer may be characterized by a homopolymer glass transition temperature (°C) of about -100, -95, -90, -85, -80, -75, -70, -65, -60, -55, -50, -45. -40, -35, -30, or -25, or a value within a range between any of the preceding values, e.g., between about -80 and about -60, between about -50 and -30, or the like. The one or more alkyl (alk)acrylate monomer characterized by a Tgof about -100 °C to about -25 °C may be referred to as a “low Tgalkyl (alk)acrylate monomer” if additional alkyl (alk)acrylate monomer(s) characterized by comparatively “high Tg” are present within the non-crosslinked acrylate polymer, for distinction. Optional high Tgalkyl (alk)acrylate monomers are discussed below.

[0095] In some embodiments, each of the one or more alkyl (alk)acrylate monomer may be characterized by a molecular weight of about 50 Da to about 200 Da. For example, the one or more alkyl (alk)acrylate monomer may be characterized by a molecular weight (Da) of about 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, or 200, or a value within a range between any of the preceding values, e.g., between about 110 and 190, between about 90 and about 120, or the like.

[0096] In some embodiments, the one or more alkyl (alk)acry late monomer may be represented by Formula I:R1-OC(O)-C(R2)=CH2(I),wherein:R1is a straight or branched C4-C20 alkyl or a Ce-Cn alkcycloalkyl, andR2is -H or C1-4 alkyl.

[0097] In some embodiments, the one or more alkyl (alk)acrylate monomer of Formula I, wherein R1is a straight or branched alkyl having a number of carbon atoms selected from 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, oravalue within a range between any of the preceding values, e.g., between 8 and 10 (i.e., Cs-Cio), between 6 and 14 (i.e., Ce-Cu), or the like. In some embodiments, eachof the one or more alkyl (alk)acrylate monomer of Formula I is selected from R1being a straight or branched alkyl selected as such.

[0098] In some embodiments, the one or more alkyl (alk)acrylate monomer of Formula I, wherein R1is a straight or branched alkoxy having a number of carbon atoms selected from 2, 3, 4, 5, or 6, or a value within a range between any of the preceding values, e.g., between 2 and 4, or the like.

[0099] Example alkyl (alk)acrylate monomers include, but are not limited to, 2-ethylhexyl acrylate, isooctyl acrylate, n-butyl acrylate, 2-methylbutyl acrylate, lauryl acrylate, 4- methyl-2 -pentyl acrylate, isoamyl acrylate, sec-butyl acrylate, n-hexyl acrylate, n-octyl acrylate, n-decyl acrylate, isodecyl acrylate, isodecyl methacrylate, isononyl acrylate, 2-ethoxyethyl acrylate.

[0100] In some embodiments, the one or more alkyl (alk)acrylate monomer may be selected from 2-ethylhexyl acrylate, isooctyl acrylate, n-butyl acrylate, and a combination thereof.

[0101] In some embodiments, the non-crosslinked acrylate polymer may be derived from only one alkyl (alk)acrylate monomer, the alkyl (alk)acrylate monomer selected from 2-ethylhexyl acrylate and isooctyl acrylate.

[0102] In some embodiments, the non-crosslinked acrylate polymer may exclude acrylate-type monomers other than those provided for in Formula I.

[0103] In some embodiments, units of the one or more alkyl (alk)acrylate monomer (e.g., Formula I) may be about 60 wt% to about 90 wt% of the weight of the non-crosslinked acrylate polymer. For example, the non-crosslinked acrylate polymer may be derived from the one or more alkyl (alk)acrylate monomer in an amount (wt%) of about 60, 62, 65, 68, 70, 72, 75, 78, 80, 85, or 90, or a value within a range between any of the preceding values, e.g., between about 60 and about 75, between about 70 and about 80, or the like. For example, the non-crosslinked acrylate polymer may include units of 2-ethylhexyl acrylate (“2-EHA”) and / or units of iso-octyl acrylate (“IO A”) present in an amount of about 70% to about 80% (e.g., 75%) of the weight of the non-crosslinked acrylate polymer. The designated percentages may refer to the total % of all alkyl (alk)acrylate monomers (low Tg) within the non-crosslinked acrylate polymer.

[0104] In some embodiments, units of the one or more alkyl (alk)acrylate monomer (e.g., 2-EHA, IO A) may be present in an amount relative to the units of the one or more polar monomer (e.g., A-vinyl pyrrolidone), within the non-crosslinked acrylate polymer, in weight ratio of about 9: 1 to about 1.5:1. For example, the weight ratio between the arylate monomer(s) and the polar monomer(s) may be about 9:1, 8.5:1, 8:1, 7.5:1, 7:1, 6.5:1, 6:1, 5.5:1, 5:1, 4.5:1, 4:1, 3.5:1, 3:1, 2.5:1, 2:1, or 1.5:1, or a value within a range between any of the preceding values, e.g., between about 6:1 and about 5:1, between about 8:1 and about 5: 1, or the like.

[0105] In some embodiments, units of the one or more alkyl (alk)acrylate monomer (e.g., 2-EHA, IO A) may be present in an amount relative to the units of the one or more polar monomer (e.g., A-vinyl pyrrolidone), within the non-crosslinked acrylate polymer, in mole ratio of about 4:1 to about 0.5:1.For example, the weight ratio between the arylate monomer(s) and the polar monomer(s) may be about 4:1, 3.8:1, 3.5:1, 3.2:1, 3:1, 2.8:1, 2.5:1, 2.2:1, 2:1, 1.8:1, 1.5:1, 1.2:1, 1:1, 0.9:1, 0.8:1, 0.7:1, 0.6:1, or 0.5:1, or a value within a range between any of the preceding values, e.g., between about 3.5:1 and about0.9:l,betweenabout2:l and about 1:1, or the like.Polar monomer

[0106] Polar monomers of the present disclosure serve to increase the glass transition temperature of the resulting non-crosslinked acrylate polymer and offer hydrogen-bonding capabilities for forming 3D networks within the adhesive, i.e., improving cohesion.

[0107] In some embodiments, the one or more polar monomer may be characterized by a homopolymer glass transition temperature of about 0 °C to about 180 °C. For example, the one or more polar monomer may be characterized by a homopolymer glass transition temperature (°C) of about 0, 2, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, or 180, or a value within a range between any of the preceding values, e.g., between about 50 and about 100, between about 100 and about 150, or the like. In some embodiments, the one or more polar monomer may be characterized by a homopolymer glass transition temperature of greater than 10 °C.

[0108] In some embodiments, the one or more polar monomer may be characterized by a molecular weight of about 100 Da to about 150 Da. For example, the one or more polar monomer may be characterized by a molecular weight of about 100, 105, 110, 115, 120, 125, 130, 135, 140, 145, or 150, or a value within a range between any of the preceding values, e.g., between about 100 and about 120, between about 105 and about 115, or the like.

[0109] In some embodiments, the one or more polar monomer may be characterized by a Log P (i.e., octanol-water partition coefficient) value of about 0.1 to about 1.0. For example, the one or more polar monomer may be characterized by a Log P value of about 0.1, 0.15, 0.2, 0.25, 0.3, 0.35, 0.4, 0.45, 0.5, 0.55, 0.6, 0.65, 0.7, 0.75, 0.8, 0.85, 0.9, 0.95, or 1.0, or a value within a range between any of the preceding values, e.g., between about 0.3 and about 0.5, between about 0.4 and about 0.6, or the like.

[0110] In some embodiments, the one or more polar monomer may be selected from a (alk)acrylic acid monomer, an (alk)acrylamide monomer, an alkylamino (alk)acrylate, a \ -vinvl lactam monomer, a vinyl ester monomer, a vinyl amide monomer a vinyl ether monomer, a vinyl aryl monomer, and a vinyl heteroaryl monomer.

[0111] Example (alk)acrylic acid monomers include, but are not limited to, acrylic acid, a methacrylic acid, itaconic acid, crotonic acid, maleic acid, fumaric acid, and the like.

[0112] Example (alk)acrylamide monomers include, but are not limited to, acrylamide, methacrylamide, \-mcthyl acrylamide, \-cthyl acrylamide, diacetone acrylamide, \, \-dimcthvl acrylamide, \.\-dicthyl acrylamide, \-cthvl-\-aminocthvl acrylamide, / -butyl acrylamide, N, N-dimethylaminoethyl acrylamide, and \ -octyl acrylamide, and the like.

[0113] Example alkylamino (alk)acrylates include, but are not limited to, 2-(N, N-methylamino)ethyl (meth)acrylate, 2-( \, \-dicthvlamino)cthvl (meth)acrylate, 2-tert-butylaminoethyl (meth)acrylate, and the like.

[0114] Example \-vinvl lactam monomers include, but are not limited to, \-vinvlpvrrolidonc. methyl \-vinvlpyrrolidonc. and \-vinvlcaprolactam. and the like.

[0115] Example vinyl ester monomers include, but are not limited to, vinyl acetate, vinyl propionate, vinyl pivalate, and the like.

[0116] Example vinyl amine monomers include, but are not limited to, \-vinvl formamide, V- vmyl acetamide, JV-vinyl acetamide, and the like.

[0117] Example vinyl ether monomers include, but are not limited to butyl vinyl ether, / -butyl vinyl ether, cyclohexyl vinyl ether, and the like.

[0118] Example vinyl aryl monomers include, but are not limited to, styrene, alphα-methyl styrene, 4-tert-butyl styrene, vinyl 4-t-butylbenzoate, 2-vinyl napththalene, and the like.

[0119] Examples of vinyl heteroaryl monomers include, but are not limited to, 2-vinylpyridine, 4-vinylpyridine, 2-vinylpyrazine, 1-vinylpyrrole, 1-vinylimidazole, methyl 2-vinyloxazole-4-carboxylate, and the like.

[0120] In some embodiments, the one or more polar monomer may be a \ -vinvl lactam monomer, e.g., \-vinvl pyrrolidone.

[0121] In some embodiments, the one or more polar monomer may exclude monomers having a hydroxyl group. Monomers having a hydroxyl group include, but are not limited, to 2 -hydroxyethyl acrylate or methacrylate, 3-hydroxypropyl acrylate or methacrylate, \ -hydroxy ethyl acrylamide.

[0122] In some embodiments, units of the one or more polar monomer (e.g., \ -vinvl lactam monomer) may be about 10 wt% to about 40 wt% of the weight of the non-crosslinked acrylate polymer. For example, the non-crosslinked acrylate polymer may be derived from one or more polar monomer (e.g., \-vinvl lactam monomer) in an amount (wt%) of about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40, or a value within a range between any of the preceding values, e.g., between about 20 and about 25, between about 20 and about 30, or the like. For example, the non-crosslinked acrylate polymer may include units of \-vinvl pyrrolidone present in an amount of about 20 wt% to about 30 wt% (e.g., about 25 wt%) of the weight of the non-crosslinked acrylate polymer. The designated percentages may refer to the total % of all polar monomers within the non-crosslinked acrylate polymer that characterized by a homopolymer glass transition temperature of 0 °C - 180 °C.

[0123] In some embodiments, units of the one or more polar monomer (e.g., \ -vinvl lactam monomer) may be about 20 mol% to about 55 mol% of the total molar amount of the non-crosslinked acrylate polymer. For example, the non-crosslinked acrylate polymer may be derived from one or more polar monomer (e.g., \ -vinvl lactam monomer) in an amount (mol%) of about 20, 22, 25, 28, 30, 32,35, 36, 38, 40, 42, 45, 48, 50, 52, or 55 or a value within a range between any of the preceding values, e.g., between about 22 and about 52, between about 20 and about 30, or the like.

[0124] In some embodiments, the non-crosslinked acrylate polymer may be derived from (1) the one or more acrylate monomer (e.g., Formula I, e.g., 2-EHA, IOA) and (2) the one or more polar monomer (e.g., \ -vinvl lactam monomer, e.g., A-vinylpyrrolidone). Units of (1) and (2) may be present within the non-crosslinked acrylate polymer in a weight ratio (1:2) of about 9:1 to about 1.5:1 and a mole ratio (1:2) of about 4:1 to about 0.5:1.

[0125] In some embodiments, the non-crosslinked acrylate polymer may be derived only of, or otherwise consisting essentially of (1) and (2). In other words, the non-crosslinked acrylate polymer may exclude monomers other than the one or more acrylate monomer (e.g., Formula I, e.g., 2-EHA, IOA) and the one or more polar monomer (e.g., \ -vinvl lactam monomer, e.g., A-vinyl pyrrolidone).Optional Alkyl (Alk)Acrylate Monomers (High Tg)

[0126] In some embodiments, the non-crosslinked acrylate polymer may be further derived from one or more additional alkyl (alk)acrylate monomer characterized by a homopolymer glass transition temperature of greater than -25 °C to about 200 °C. For example, the one or more additional alkyl (alk)acrylate monomer may be characterized by a homopolymer glass transition temperature (°C) of about -26, -20, -10, 0, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, or 200, or a value within a range between any of the preceding values, e.g., between about 20 and about 100, between about 0 and about 180, or the like.

[0127] Example alkyl (alk)acrylate (high Tg) monomers include, but are not limited to, methyl (meth)acrylate, ethyl (meth)acrylate, isobomyl (meth)acrylate, biphenylyl (meth)acrylate, t-butylphenyl (meth)acrylate, cyclohexyl acrylate, dimethyladamantyl (meth)acrylate, 2-naphthyl (meth)acrylate, phenyl (meth)acrylate, and the like.

[0128] In some embodiments, the non-crosslinked acrylate polymer may be further derived one or more high Tgalkyl (alk)acrylate monomer, the one or more high Tgalkyl (alk)acrylate monomer (if present) may be present in an amount of no greater than 20 wt% of the weight of the non-crosslinked acrylate polymer. For example, the one or more high Tgalkyl(alk)acrylate monomer may be present within the non-crosslinked acrylate polymer in an amount (wt%) in an amount of about 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, or a value within a range between any of the preceding values, e.g., between about 5 and about 15, between about 10 and about 20, or the like.

[0129] In other embodiments, the non-crosslinked acrylate polymer may exclude being derived from high Tgalkyl (alk)acrylate monomers.Hydrocarbon Compound

[0130] Many of the hydrocarbon compound(s) described herein are known to plasticize rubbers and rubber adhesives (i.e., diene monomer-based polymers) because they are highly hydrophobic. However, such hydrocarbon compound(s) are not compatible with acrylate-based adhesives. In other words, hydrocarbon compound(s) are not miscible with acrylate-based adhesives, such as the noncrosslinked acrylate polymer (or crosslinked acrylate polymer) of the present disclosure, without the presence of a suitable solubilizing substance, such as the plasticizers described herein.

[0131] In many embodiments, the organogel pressure-sensitive adhesive may include one or more hydrocarbon compound defined below.

[0132] In many embodiments, the at least one hydrocarbon compound may be characterized as being immiscible with the non-crosslinked acrylate polymer described herein. As used herein, “immiscible” or “not miscible” means that two substances, when combined, do not form a homogenous solution. For example, two immiscible liquids result in a biphasic mixture, i.e., the two liquids separate like oil and water. As used herein, these terms regard a temperature of 25 °C and pressure of lOlkPa, and only concern the components that are stated, i.e., absent any additional component(s) such as surfactant, salts, phase transfer catalysts, or the like.

[0133] In some embodiments, the at least one hydrocarbon compound may be characterized as a liquid at 25 °C and lOlkPa.

[0134] In some embodiments, the at least one hydrocarbon compound may be characterized by a molecular weight of about 200 Da to about 700 Da. For example, the at least one hydrocarbon compound may be characterized by a molecular weight of about 200, 220, 250, 280, 300, 320, 350, 380, 400, 420, 450, 480, 500, 520, 550, 580, 600, 620, 650, 680, or 700, or a value within a range between any of the preceding values, e.g., between about 200 and about 250, between about 200 and about 280, or the like.

[0135] In some embodiments, the at least one hydrocarbon compound may be a polymer and characterized by a molecular weight of up to about 3000 Da. For example, the polymer may be characterized by a molecular weight (Da) of about 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2100, 2200, 2300, 2400, 2500, 2600, 2700, 2800, 2900, or 3000, or a value within a range between any of the preceding values, e.g., between about 1000 and about 2300, between about 800 and about 2500, or the like.

[0136] In some embodiments, the at least one hydrocarbon compound may be characterized by a boiling point of at least 200 °C at lOlkPa. In some embodiments, the at least one hydrocarbon compound may be characterized by a boiling point of about 200 °C to about 600 °C at lOlkPa. For example, the at least one hydrocarbon compound may be characterized by a boiling point (°C at 10 IkPa) of 200, 225, 250, 275, 300, 325, 350, 375, 400, 425, 450, 475, 500, 525, 550, 575, or 600, or a value within a range between any of the preceding values, e.g., between about 350 and about 400, or the like.

[0137] In many embodiments, the at least one hydrocarbon compound may include at least 15 carbon atoms. In some embodiments, the at least one hydrocarbon compound may include up to 50 carbon atoms. For example, the hydrocarbon compound as defined may be a hydrocarbon compound having a number of carbon atoms of 15, 18, 20, 22, 25, 28, 30, 32, 35, 38, 40, 42, 45, 48, or 50 (i.e., C15-50), or a value within a range between any of the preceding values, e.g., between 15 and 18 (i.e., C15-18), between 20 and 28 (i.e., C20-28), or the like. In other embodiments, the hydrocarbon compound (if polymeric) may have up to 250 carbons, e.g., 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, or 250, or a value within a range between any of the preceding values, e.g., between 80 and 200 carbons, between 100 and 150 carbons, or the like.

[0138] In many embodiments, the at least one hydrocarbon compound may be a saturated hydrocarbon, i.e., does not include units of unsaturation, e.g., alkenes, alkynes.

[0139] In many embodiments, the at least one hydrocarbon compound (e.g., C15-50or range selected from above) may be selected from a linear or branched alkane, a cycloalkane optionally substituted with one or more linear or branched alkyl group, a polycyclic cycloalkane optionally substituted with one or more linear or branched alkyl group, and a combination thereof. In many embodiments, the at least one hydrocarbon may be selected from the above-listed components which may exclude one or more of: heteroatom-containing functional groups (e.g., alcohols, esters, amines, amides, ketones, heterocycles, and the like), polymerizable groups (e.g., olefins), and polycyclic aromatic hydrocarbons groups.

[0140] In some embodiments, the at least one hydrocarbon may be one or more component of mineral oil. Mineral oil may be a combination of mostly paraffins (linear or branched alkanes) and naphthenes (cycloalkane-containing alkanes), having carbon counts of less than 20 (e.g., ≤C18, i.e., liquid hydrocarbons).

[0141] In other embodiments, the at least one hydrocarbon may be one or more component of petrolatum (i.e., petroleum jelly). Petrolatum contains both solid (e.g., >C20) and liquid (e.g., ≤C20, e.g., ≤C18) paraffin and naphthene-type hydrocarbons. Paraffin wax, on the other hand, is primarily a mixture of solid (e.g., C20-C30) paraffins and naphthene-type hydrocarbons. In other words, petrolatum may be a mixture of mineral oil-type hydrocarbons and paraffin wax-type hydrocarbons.

[0142] In many embodiments, the hydrocarbon compound may be a polymer. In some embodiments, the polymer may be a saturated hydrocarbon, i.e., derived from monoalkenes or otherwise derived from dienes or the like and the polymer has been subsequently hydrogenated. In some embodiments, the at least one hydrocarbon carbon may be a polymer derived solely from one or more C2-C6monoalkene (e.g., C2alkene (ethylene), C3alkene (e.g., propylene, isopropylene), C4alkene (e.g., butylene, isobutylene), and the like). Polyisobutylene is one example of a hydrocarbon compound polymer.

[0143] In many embodiments, the at least one hydrocarbon compound (i.e., liquid hydrocarbon compounds) may be present in an amount of about 20 wt% to about 50 wt% with respect to the weightof the organogel pressure-sensitive adhesive. For example, the at least one hydrocarbon compound may be present in an amount of about 20, 22, 25, 28, 30, 32, 35, 38, 40, 42, 45, 48, or 50, or a value within a range between any of the preceding values, e.g., 25 and about 35, between about 30 and about 45, or the like. The designated percentages may encompass a total % of all hydrocarbon compounds, as defined.

[0144] In some embodiments, the at least one hydrocarbon compound may be present in an amount relative to an amount of the plasticizer at a weight ratio of about 0.5: 1 to about 3:1. For example, the weight ratio of hydrocarbon compound(s) to plasticizer(s) may be about 0.5:1, 0.8:1, 1:1, 1.2:1, 1.5:1, 1.8:1, 2:1, 2.2:1, 2.5:1, 2.8:1, or 3:1, or a value within a range between any of the preceding values, e.g., between about 1:1 to about 2:1, between about 0.5:1 and about 2.2:1, or the like. In some embodiments, the at least one hydrocarbon compound may be a mineral oil present in a weight ratio relative to the plasticizer of about 0.5:1 to about 3:1 (e.g., 0.5:1 to 2:1). In some embodiments, the at least one hydrocarbon compound may be a polymer derived from one or more C2-C6alkene (e.g., polyisobutylene) and present in a weight ratio relative to the plasticizer of about 0.5:1 to about 3:1 (e.g., 0.5:1 to 2:1). In other embodiments, the at least one hydrocarbon compound may be a petroleum jelly and present in a weight ratio relative to the plasticizer of about 0.5:1 to about 2.2:1 (e.g., 0.5:1 to 2:1, e.g., 0.5: 1 to 1: 1). If the weight ratio between the at least one hydrocarbon compound and the plasticizer is too high (i.e., not enough plasticizer), then the at least one hydrocarbon compound may phase separate from the organogel pressure-sensitive adhesive over time or upon debonding. While non-optimal weight ratios may afford suitable pressure-sensitive adhesives, such adhesives may not have desired wear times or may preclude such adhesives from being removed and re-applied due to blooming.Plasticizer

[0145] In some embodiments, the plasticizer may be characterized as a liquid at 25 °C and 101 kPa.

[0146] In some embodiments, the plasticizer may be characterized by a molecular weight of about 1500 Da to about 3500 Da. For example, the plasticizer may be characterized by a molecular weight (Da) of about 1500, 1600, 1700, 1800, 1900, 2000, 2100, 2200, 2300, 2400, 2500, 2600, 2700, 2800, 2900, 3000, 3100, 3200, 3300, 3400, or 3500, or a value within a range between any of the preceding values, e.g., between about 1800 and about 2200, between about 1500 and about 2500, or the like. In some embodiments, the plasticizer may be characterized by a glass transition temperature of about -100 °C to about 0 °C. For example, the plasticizer may be characterized by a glass transition temperature (°C) or about -100, -95, -90, -85, -80, -75, -70, -65, -60, -55, -50, -45, -40, -35, -30, -25, -20, -15, -10, -5, or 0, or a value within a range between any of the preceding values, e.g., between about -75 and about -50, between about -60 and about -5, or the like.

[0147] In some embodiments, the plasticizer may be characterized by an HLB value of about 0.1 to about 5. For example, the plasticizer may be characterized by an HLB value of about 0.1, 0.5, 1, 1.2, 1.5, 1.8, 2.0, 2.2, 2.5, 2.8, 3.0, 3.2, 3.5, 3.8, 4.0, 4.2, 4.5, 4.8, or 5, or a value within a range between any of the preceding values, e.g., between about 1 and about 2, between about 2.5 and about 3, or the like. In many embodiments, the organogel pressure-sensitive adhesive may exclude plasticizing components characterized by an HLB value of greater than 5.

[0148] In some embodiments, the plasticizer may be a polyester polyol.

[0149] In some embodiments, the plasticizer may be a polyester polyol derived from dimerized fatty acids, dimerized fatty alcohols, or a combination thereof.

[0150] In some embodiments, the plasticizer may be represented by one or more compound of Formula IV:R9-A-R11-B-R10(IV),wherein:R9and R10are each independently selected from a straight or branched C1-C40 alkyl optionally substituted with -OH or -CO2R12, a straight or branched C1-C40 alkenyl optionally substituted with -OH or -CO2R12, a C8-C40 alkcycloalkyl optionally substituted with -OH or -CO2R12, and a C8-C40 alkcycloalkenyl optionally substituted -OH or -CO2R12,R11is a straight or branched C8-C40 alkylene, a straight or branched C8-C40 alkenylene, a C8-C40 alkcycloalkylene, or a C8-C40 alkcycloalkenylene,R12is -H or a C1-C4 alkyl, andA and B are independently selected -OC(O)-, -C(O)O-, -NHC(O)-, -C(O)NH-, and -O-.

[0151] In some embodiments, R9and R10may each an alkyl having a number of carbon atoms selected from 1, 2, 3, 4, 5, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, or 40, or a value within a range between any of the preceding values, e.g., between 2 and 4, between 34 and 38, or the like. In some embodiments, R9and R10may each an alkyl (e.g., C34-C38) substituted with -OH. In some embodiments, R9and R10may each a straight or branched C1-4alkyl.

[0152] In some embodiments, R9and R10may each be an alkcycloalkenyl substituted with and -OH and represented by the formula:

[0153] In some embodiments, R9and R10may each a branched alkyl substituted with -OH and represented by the formula:

[0154] In some embodiments, R11may be a straight or branched alkylene or a straight or branched alkenylene having a number of carbon atoms selected from 8, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, or 40, or a value within a range between any of the preceding values, e.g., between 18 and 22, between 34 and 38, or the like.

[0155] In some embodiments, R11may be an alkcycloalkylene or an alkcycloalkenylene having a number of carbon atoms selected from 8, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, or 40, or a value within a range between any of the preceding values, e.g., between 8 and 10, between 34 and 38, or the like.

[0156] In some embodiments, R11may be an alkcycloalkenylene represented by the formula:

[0157] In some embodiments, R11may be a branched alkyl represented by the formula:

[0158] In some embodiments, the organogel pressure-sensitive adhesive may exclude plasticizing components other than the plasticizers described herein.

[0159] In some embodiments, the plasticizer may be present in an amount of about 30 wt% to about 55 wt% with respect to the weight of the organogel pressure-sensitive adhesive. For example, the plasticizer may be present in an amount (wt%) of about 30, 32, 35, 38, 40, 42, 45, 48, or 50, 55, or a value within a range between any of the preceding values, e.g., between about 30 and about 35, between about 32 and about 40, or the like.Tackifier

[0160] In some embodiments, the organogel pressure-sensitive adhesive may further include a tackifier. Tackifiers increase tack and peel strength but decrease cohesion. In other embodiments, the organogel pressure-sensitive adhesive may exclude tackifiers.

[0161] In some embodiments the tackifier may be characterized as being a solid at 25 °C and 101 kPa. In some embodiments, the tackifier may be characterized by a softening point of about 70 °C to about 180 °C at 101 kPa. For example, the tackifier may be characterized by a softening point (°C) of about 70, 75, 80, 85, 90, 95, 100, 105, 110, 115, 120, 125, 130, 135, 140, 145, 150, 155, 160, 165, 170, 175, or 180, or a value within a range between any of the preceding values, e.g., between about 95 and about 160, between about 80 and about 100, or the like.

[0162] In some embodiments, the tackifier may be characterized by a molecular weight of at least 700 Da. In some embodiments, the tackifier may be characterized by a molecular weight of no greater than 1500 Da. For example, the tackifier may be characterized by a molecular weight of 700, 725, 750, 775, 800, 825, 850, 875, 900, 925, 950, 975, 1000, 1025, 1050, 1075, 1100, 1125, 1150, 1175, 1200, 1250, 1275, 1300, 1325, 1350, 1375, 1400, 1425, 1450, 1475, or 1500, or a value within a range between any of the preceding values, e.g., between about 1000 and about 1300, between about 700 and about 1000, or the like.

[0163] In some embodiments, the tackifier may be characterized by a glass transition temperature of at least 25 °C. In some embodiments, the tackifier may be characterized by a glass transition temperature of no greater than 120 °C. For example, the tackifier may be characterized by a glass transition temperature (°C) of 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 105, 110, 115, or 120, or a value within a range between any of the preceding values, e.g., between about 40 and about 110, between about 50 and about 75, or the like.

[0164] In some embodiments, the tackifier may be characterized by an HLB value of no greater than 5. For example, the tackifier may be characterized by an HLB value of 0.1, 0.5, 0.8, 1.0, 1.2, 1.5, 1.8, 2.0, 2.2, 2.5, 2.8, 3.0, 3.2, 3.5, 3.8, 4.0, 4.2, 4.5, 4.8, or 5.0, or a value within a range between any of the preceding values, e.g., between about 1.0 and about 2.5, between about 0.5 and about 2, or the like.

[0165] In some embodiments, the tackifier may be a resin or a rosin. The resin or rosin may be derived from plants, petroleum, or both.

[0166] In some embodiments, the tackifier may be an unsaturated hydrocarbon polymer.

[0167] In many embodiments, the tackifier may be a polymer derived at least from 1,3 -diene monomers. Example conjugated diene monomers may include, but are not limited to, C5 dienes such as isoprene and piperylene, CIO and C15 terpenes such as (3-myrcene and [3-farnesene, respectively. Thus, the resulting polymer retains units of unsaturation (i.e., olefins) within the polymer structure (via 1,4-addition) and / or via unsaturated side chains, which may offer desirable tackifying properties. In other words, the tackifier may be a hydrocarbon polymer having units of unsaturation, i.e., an unsaturated hydrocarbon polymer. In some embodiments, the tackifier may be polymer derived from a co-polymerization of 1,3-dienes and other polymerizable monomers, e.g., aromatic monomers such as styrene, α-methyl styrene, vinyl toluene, indene, or the like.

[0168] In some embodiments, the tackifer may be a terpene-based polymer, terpenoid-based polymer, or terpene-terpenoid-based polymer. Examples of terpene and terpenoid-based polymerizations can be found at Palenzuela, M. Adv. Organomet. Chem. 2021, 75, 55-93, which is incorporated herein by reference in its entirety.

[0169] In some embodiments, the tackifer may be an aromatically -modified C5 hydrocarbon resin. The term “aromatically-modified C5 hydrocarbon resin” may be a hydrocarbon copolymer derived from one or more 1,3-diene having a carbon count in multiples of 5 (e.g., 5, 10, 15, 20, etc) and one or more aromatic monomer.

[0170] In some embodiments, the tackifier (if present) may be present in an amount of no greater than 40 wt%. In some embodiments, the tackifier may be present in an amount of about 1 wt% to about 25 wt% with respect to the weight of the organogel pressure-sensitive adhesive. For example, the plasticizer may be present in an amount of about 1, 2, 3, 4, 5, 8, 9 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25, or a value within a range between any of the preceding values, e.g., between about 10 and about 20, between about 14 and about 16, or the like. In other embodiments, the organogel pressure-sensitive adhesive may exclude tackifiers.

[0171] In some embodiments, the tackifier, if present, may be present in an amount relative to an amount of plasticizer at a weight ratio of about 0.1:1 to about 1:1. For example, the weight ratio of tackifier(s) (e.g., aromatically-modified C5 hydrocarbon resin) to plasticizer(s) (e.g., polyester polyol) may be about 0:1, 0.1:1, 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, 0.7:1, 0.8:1, 0.9:1, 1:1, or a value within a rangebetween any of the preceding values, e.g., between about 0.5: 1 to about 0.8:1, between about 0.2:1 and about 0.6:1, or the like.

[0172] In some embodiments, the tackifier, if present, may be present in an amount relative to an amount of non-crosslinked acrylate polymer at a weight ratio of about 1:0.25 to about 1:1. For example, the weight ratio of tackifier(s) (e.g., aromatically-modified C5 hydrocarbon resin) to non-crosslinked acrylate polymer may be about 1:0.25, 1:0.3, 1:0.35, 1:0.4, 1:0.45, 1:0.5, 1:0.55, 1:0.6, 1:0.65, 1:0.7, 1:0.75, 1:0.8, 1:0.85, 1:0.9, 1:0.95, or 1:1, or a value within a range between any of the preceding values, e.g., between about 1:0.4 to about 1:0.9, between about 1:0.5 to about 1:0.8, or the like.

[0173] In some embodiments, the tackifier, if present, may be present in an amount relative to an amount of the at least one hydrocarbon compound (e.g., mineral oil) at a weight ratio of about 1:1 to about 1:3. For example, the weight ratio of tackifier(s) (e.g., aromatically-modified C5 hydrocarbon resin) to hydrocarbon compound(s) may be about 1:1, 1:1.2, 1:1.5, 1:1.8, 1:2, 1:2.2, 1:2.5, 1:2.8, or 1:3, or a value within a range between any of the preceding values, e.g., between about 1:1.5 and about 1:2, between about 1:2 and about 1:2.5, or the like.Antimicrobial Agents / Compounds

[0174] In many embodiments, the organogel pressure-sensitive adhesive may further include an antimicrobial agent. In some embodiments, the antimicrobial agent may be a quaternary ammonium salt.

[0175] In some embodiments, the quaternary ammonium salt may be an alkonium salt of formula Va:R1-N+(CH3)2R2X- (Va),wherein R1may be a C6-22alkyl, e.g., a C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, or C22alkyl, or a range between any of the preceding values, e.g., a C12-16alkyl, a C8-18alkyl, or the like; R2may be a C1-22 alkyl, e.g., a C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, or C22alkyl, or a range between any of the preceding values, e.g., a C1-6alkyl, a C1-4alkyl, or the like; and X is Cl, Br, or I.

[0176] In some embodiments, the quaternary ammonium salt may be an alkonium salt of formula (Vb):R1-N+(CH3)3X-(Vb),wherein R1may be a C6-22alkyl, e.g., a Ce, C7, C8, C9, C10, Cn, C12, Cn, C14, C15, Ci6, C17, Cis, C19, C20, C21, or C22 alkyl, or a range between any of the preceding values, e.g., a C12-16alkyl, a C8-18alkyl, or the like; and X is Cl, Br, or I.

[0177] In some embodiments, the quaternary ammonium salt may be an alkonium salt of the formula:

[0178] In some embodiments, the quaternary ammonium salt may be an alkonium salt of the formula:

[0179] In many embodiments, the quaternary ammonium salt may be a benzalkonium salt selected from one or more compound of the formula (Via):(Via),wherein n may be an integer from 1-22, e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18, or a range between any of the preceding values, e.g., 8-18, 10-16, or the like; and X may be Cl, Br, or I. In some embodiments n may be selected from an integer of 8, 10, 12, 14, 16, or 18. In some embodiments the composition may include one or more benzalkonium chloride of formula Via. For example, the wound care composition may include a mixture of benzalkonium salts wherein n is 8, 10, 12, 14, 16, and 18.

[0180] In some embodiments, the quaternary ammonium salt may be a benzalkonium salt of formula VIb:PhCH2N+(CH3)2-(CH2)m-NH-C(O)-R4X’ (VIb), wherein R4may be a C4-22alkyl group, e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, or C22alkyl, or a range between any of the preceding values, e.g., a C13-17alkyl, a C10-18alkyl, or the like; m may be an integer of 2-4; and X may be Cl, Br, or I. “Ph” is phenyl.

[0181] In some embodiments, the quaternary ammonium salt may be a benzalkonium salt of the formula:

[0182] In some embodiments, the quaternary ammonium salt may be a benzethonium salt selected from one or more compound of formula (Vila):PhCH2N+(CH3)2(CH2CH2O)n-R6X’ (Vila),wherein R6may be Ph or -Ph-R10, R10may be a C4-10 alkyl, n may be an integer selected from 1-6, and X may be Cl, Br, or I. “Ph” is phenyl or phenylene.

[0183] In some embodiments, the quaternary ammonium salt may be a benzethonium salt of the formula:Cl⁻

[0184] In some embodiments, the quaternary ammonium salt may be a pyridinium salt of formula Villa:. J v- AR9(Villa),wherein R9may be a C4-22 alkyl, e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, or C22alkyl, or within a range of any of the preceding values, e.g., a C12-18alkyl, a C10-16alkyl, or the like; and X may be Cl or Br.

[0185] In some embodiments, the quaternary ammonium salt may be a pyridinium salt of formula:

[0186] In some embodiments, the quaternary ammonium salt may be a pyridinium salt of formula VIIIb:NHR11X-R10wherein R10may be a C4-C22alkylene, e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, or C22alkylene, or within a range between any of the preceding values, e.g., C8-C12, or the like; R11may be a C1-C12alkyl, e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, or C12alkyl, or within a range between any of the preceding values, e.g., C6-C10alkyl, or the like; and X may be Cl or Br.

[0187] In some embodiments, the quaternary ammonium salt may be a pyridinium salt of formula:

[0188] In some embodiments, the quaternary ammonium salt (e.g., benzalkonium chloride, octenidine hydrochloride) may be present in an amount of about 0.01 wt.% to about 3 wt.% with respect to the weight of the organogel pressure sensitive adhesive. For example, the quaternary ammonium salt may be present in an amount, in wt.%, of about 0.01, 0.02, 0.03, 0.04, 0.05, 0.1, 0.13, 0.15, 0.18, 0.2, 0.23, 0.25, 0.28, 0.3, 0.32, 0.35, 0.38, 0.4, 0.45, 0.5, 0.55, 0.6, 0.65, 0.7, 0.75, 0.8, 0.85, 0.9, 0.95, 1.0, 1.2, 1.5, 1.8, 2.0, 2.2, 2.5, 2.8, or 3.0 a value within a range between any of the preceding values, e.g., between about 0.05 and about 0.5, between about 0.7 and about 0.9, between about 1.5 and about 3.0 or the like.

[0189] In some embodiments, the quaternary ammonium salt (e.g., benzalkonium salt) may be accompanied by one or more of: a C8-12alkyl 1,2-diol (e.g., 1,2-octanediol) and a chelator compound (e.g., citric acid, citrate). It is known that both C8-12alkyl 1,2-diols and chelator compounds can synergistically enhance the antimicrobial activity when combined with benzalkonium salts. Thus, in some embodiments, the organogel pressure sensitive adhesive may further include a C8-12alkyl 1,2-diol, a chelator compound, or a combination thereof.

[0190] In many embodiments, the organogel pressure-sensitive adhesive may exclude other antiseptic compounds, such as polyhexamethylene biguanide (“PHMB”), iodine, chlorhexidine, silver salts, or the like.COMPOSITIONS FOR PREPARING PRESSURE-SENSITIVE ADHESIVES

[0191] In various embodiments, a composition for preparing an organogel pressure-sensitive adhesive of the present disclosure is described. In some embodiments, the composition may include any organogel pressure-sensitive adhesive described herein, with the addition of one or more volatile solvent (e.g., characterized by a vapor pressure of greater than 0.3 kPa at 20 °C). The one or more volatile solvent may be selected such that each component within the organogel pressure-sensitive adhesive is dissolved within the selected solvent.

[0192] In various embodiments, a composition for preparing an organogel pressure-sensitive adhesive described herein is provided. The composition may include one or more volatile solvent (e.g., characterized by a vapor pressure of greater than 0.3 kPa at 20 °C); the one or more alkyl (alk)acrylate monomer; the one or more polar monomer; the at least one hydrocarbon compound; the plasticizer; and optionally a tackifier (all of which as described above). In some embodiments, the composition may further include a photoinitiator system.

[0193] In many embodiments, the composition for preparing the organogel pressure-sensitive adhesive may include a co-solvent system, i.e., two or more volatile solvents. The co-solvent system may include a non-polar solvent that is miscible with the hydrocarbon compound(s) described herein and a relatively more polar solvent that is miscible with the non-crosslinked acrylate polymer described herein. The non-polar solvent and relatively more polar solvent may be selected based on their miscibility with each other. For example, the non-polar solvent may be selected from pentane, hexanes, cyclohexane, heptane, xylenes, benzene, or the like. For example, the relatively polar solvent may be selected from methyl ethyl ketone, methyl t-butyl ether, tetrahydrofuran, diethyl ether, acetone, or the like. In some embodiments, the non-polar solvent and the relatively polar solvent may be present in a ratio of about 3:1 to about 1:1, e.g., 3:1, 2.5:1, 2:1, 1.5:1, or 1:1, or a value within a range between any of the preceding values.

[0194] In some embodiments, the composition for preparing the organogel pressure sensitive adhesive may exclude water.

[0195] In some embodiments, the one or more volatile solvent may be present within the composition in an amount of at least 10 wt%. For example, the one or more volatile solvent may be present within the composition in an amount (wt%) of about 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, or more, or a value within a range between any of the preceding values, e.g., between about 30 to about 50, between about 50 and about 75, or the like.

[0196] Compositions having one or more volatile solvent may be used in solvent-cast processes for preparing the pressure sensitive adhesives. However, the organogel pressure-sensitive adhesives may also be prepared by a hot-melt process. Thus, in other embodiments, the compositions may exclude solvents and water.

[0197] In some embodiments, the composition for preparing the organogel pressure-sensitive adhesive may exclude chain transfer reagents. A chain transfer agent is a compound that can control the molecular weight of a polymer during polymerization, i.e., chain transfer agents are reactive toward a growing polymer. Such agents are characterized by having a labile chemical bond under polymerization reaction conditions (e.g., radical polymerization). Example labile chemical bonds or functional groups containing labile chemical bonds include, but are not limited to, hydroxyl (i.e., -OH; e.g., alcohols such as methanol, ethanol, isopropanol, or the like), thiol (i.e., -SH; e.g., dodecyl mercaptan), thioester (i.e., -C(O)-S-R), dithioesters (i.e., -C(S)-S-R), halocarbons (e.g., carbon tetrachloride, chloroform), and the like. Known acrylate-based PSAs that are capable of being hot-melt processed require chain transfer agents to control the molecular weight, and thus, control the viscosity. The organogel nature of the PSAs of the present disclosure avoids the need to control molecular weight / viscosity of the acrylate polymer for the PSA to be processed by a hot-melt technique. This unique aspect of the organogel PSAs of the present disclosure greatly reduces manufacturing costs, improves manufacturing safety, and aligns with sustainability efforts, in addition to drastically reducing MARSI due to its gentle-release properties. However, this acknowledged benefit should not prohibit the use of chain transfer agents within the organogel PSAs of the present disclosure. Thus, in some embodiments, the composition for preparing the organogel PSAs of the present disclosure may further include a chain transfer agent.ARTICLES OF MANUFACTURE

[0198] In various embodiments, a medical article having an organogel pressure-sensitive adhesive described herein, is described.

[0199] In some embodiments, the medical article may include the organogel pressure-sensitive adhesive of the present disclosure on a substrate. The substrate may be composed of any material. Various polymeric materials in the form of films, woven materials, and non-woven materials, or the like, are known as backing materials known in use for medical articles.

[0200] In some embodiments, the medical article may be a wound bandage, a compression wrap, a catheter or port cover, a moisture barrier, a wearable medical article (e.g., continuous glucose monitoring device), a surgical drape, steri-strips, a medical tape, a transdermal patch, an ostomy bag mount, a biomedical electrode, or the like.

[0201] In some embodiments, the organogel pressure-sensitive adhesive may be present on the substrate at a thickness of about 0.1 mil to about 5 mil. For example, the organogel pressure-sensitiveadhesive may be present on the medical article at a thickness (mil) of about 0.2, 0.5, 0.8, 1.0, 1.2, 1.5, 1.8, 2.0, 2.2, 2.5, 2.8, 3.0, 3.2, 3.5, 3.8, 4.0, 4.2, 4.5, 4.8, or 5.0, or a value within a range between any of the preceding values, e.g., between about 1 mil to about 2.5 mil, between about 0.5 mil to about 2.5 mil, or the like.PROCESSES FOR PREPARING PRESSURE-SENSITIVE ADHESIVES AND ARTICLES

[0202] In various embodiments, a process for preparing an organogel pressure-sensitive adhesive of the present disclosure is described. The process may include providing and combining 1) an acrylate polymer prepared from the one or more alkyl (alk)acrylate monomer and 2) the one or more polar monomer, the at least one hydrocarbon compound, the plasticizer, and optionally a tackifier to form a composition; and mixing the composition to form the organogel pressure-sensitive adhesive.

[0203] In various embodiments, a process for preparing an article (e.g., medical article) having an organogel pressure-sensitive adhesive of the present disclosure is described. The process may include providing a composition having 1) an acrylate polymer prepared from the one or more alkyl (alk)acrylate monomer and 2) the one or more polar monomer, the at least one hydrocarbon compound, the plasticizer, and optionally a tackifier; and a substrate. The process may further include contacting the composition to the substrate to form the article.

[0204] In various embodiments, an in-situ polymerization process for preparing an organogel pressure-sensitive adhesive of the present disclosure is described. The process may include providing a composition having 1) the one or more alkyl (alk)acrylate monomer, and 2) the one or more polar monomer, the at least one hydrocarbon compound, the plasticizer, and optionally a tackifier. The process may include subjecting the composition to conditions effective to promote polymerization of the 1) the one or more alkyl (alk)acrylate monomer and 2) the one or more polar monomer. In some embodiments, the conditions may include contacting the composition to a photoinitiator system to form a mixture and irradiating the mixture with UV irradiation.

[0205] In various embodiments, a solvent-cast process for preparing an article (e.g., medical article) of the present disclosure is described. The process may include providing a substrate and a composition having 1) one or more volatile solvent, 2) the non-crosslinked acrylate polymer, 3) the at least one hydrocarbon compound, 4) the plasticizer, and 5) optionally a tackifier; contacting the composition to the substrate; and removing the one or more volatile solvent to form the article having the organogel pressure-sensitive adhesive thereon.

[0206] In various embodiments, a hot-melt process for preparing a medical article of the present disclosure is described. The process may include providing a substrate and an organogel pressuresensitive adhesive of the present disclosure; heating the organogel pressure-sensitive adhesive to form a heated pressure-sensitive adhesive; and contacting the heated pressure-sensitive adhesive to the substrate to form the medical article having the organogel pressure-sensitive adhesive thereon.METHODS OF USE

[0207] In various embodiments, a method of adhering a medical article of the present disclosure to a skin surface is described. The method may include contacting the organogel pressure-sensitive adhesive on the medical article to the skin surface of the subject.

[0208] The organogel pressure-sensitive adhesives of the present disclosure may be removed and reapplied without causing injury to the skin surface or compromising the integrity of the organogel pressure-sensitive adhesive. Thus, in some embodiments, the method may further include removing the medical article and reapplying. Removing and reapplying may be necessary when a user incorrectly applies the medical article.KITS

[0209] In various embodiments, a kit is described. The kit may include a medical article of the present disclosure and a set of instructions directing a user to contact the medical article to a skin surface.

[0210] In various embodiments, a kit is described. The kit may include a composition described herein for preparing an organogel pressure-sensitive adhesive as described herein and a set of instructions directing a user to prepare a medical article as described herein.EXAMPLESMethods

[0212] The formulations below were cured and tested according to the test procedures provided below.UV Curing Procedure

[0213] UV-curing was performed by exposing the uncured adhesive coated on substrate backing to UV radiation from a Fusion UV lamp at 300W / in. power, equipped with a conveyor belt. The sample is cured on the conveyor belt at a speed of 15-30fpm.E-beam Curing Procedure

[0214] E-beam curing was performed on a Model CB-300 electron beam generating apparatus (available from Energy Sciences, Inc. (Wilmington, Mass.)). Generally, a support film (e.g., polyester terephthalate support film) was run through the inerted chamber (50 ppm oxygen) of the apparatus. Samples of uncured material were attached to the support fdm and conveyed at a fixed speed of about 12.2 meters / min (40 feet / min) through the inerted chamber and exposed to electron beam irradiation at an acceleration voltage of 280 V to achieve dose values of 10, 12, and 14 MRad.

[0215] The results indicate that e-beam curing is a viable alternative to UV to achieve crosslinking. In general, an increase in the dose results in a decrease in debonding energy and a reduction in the displacement at debonding.Tack Test Procedure

[0216] Tack was measured using a TA-X T2iHR Texture Analyzer equipped with a 6 mm diameter spherical stainless steel cylinder probe. The tack test is used to measure peak value, debonding energy, and displacement at debonding.Test parameters:Pretest: 0.5 mm / sec;Test speed: 1.0 mm / sec;Post-test speed: 1.0 mm / sec;Applied force: 28 grams;Contact time: 5 Seconds,Trigger force: 1 gram, andWithdraw distance: 2 mm.

[0217] The peak value is related to the immediate tack of the adhesive. The peak value is defined as the maximum force during retraction for the primary peak.

[0218] The debonding energy is related to the work of adhesion. The debonding energy is defined as the area under the curve from the initiation of retraction to debonding.

[0219] The displacement at debonding is of particular interest. It relates to the shear adhesion or holding power of the adhesive. A higher value indicates that the energy of debonding is dissipated through the adhesive rather than the substrate resulting in a gentler release. The displacement at debonding is defined as the X-Y travel of the probe from initiation of retraction to debonding.Re-application Test

[0220] Pigskins were shaved and cleaned with isopropyl alcohol and each pressure-sensitive adhesive tape was contacted to a portion of the pigskin. The tapes were removed after 5 seconds dwell and were immediately contacted to another portion of shaved and cleaned pigskin. The removal and re-application process was repeated with each pressure-sensitive adhesive tape until the organogel pressure-sensitive adhesive tape no longer adhered reliably.Moisture Vapor Transmission Rate (" MVTR”) Test

[0221] Adhesive samples are pre-cut to a disc shape having a diameter of 3.8 cm. The paper liner is removed from the adhesive surface of the dressing and the disc is placed between two foil rings with elliptical openings, thus exposing a dressing sample surface area of 5.1 cm2 and forming a foil / dressing / foii assembly (the "assembl ") ). To test upright MVTR, 50 ml of deionized water is placed inside a 4-oz. jar.

[0222] One or two drops of methylene blue mixture (0.17% wt / wt methylene blue aqueous solution) are added to the jar as a visual aid to detect sample leakage. An assembly is placed on the rubber washer ring over the bottle mouth with the adhesive surface of the assembly facing downward toward the interior of the jar. The jar is placed in a chamber at a temperature of 40°C + / - 1 °C and 20% relative humidity for four hours. A sealing ring having a circular opening in its center, the opening having a diameter of 1.5 in.(3.8 cm), is tightened onto the jar mouth while the jar is inside the chamber to secure the assembly to the jar. The jar is removed from the chamber and weighed immediately; the mass is recorded as e

[0223] The jar is returned to the chamber for a minimum of eighteen hours (the "test period"), then the jar is removed from the chamber and is immediately reweigbed; the mass is recorded as W?. The time the jar is in tire draniber after measuring Wt. i.e., the lest period, is recorded as T. The upright MVTR is calculated using Formula I below:MVTR ~ (W; - Wj4 74;< 104(houss) minimum 18WlW2 ~ final weigh! (grams)- ss><:. >>^».<f.>.i Fcjnnula Iwhere:W1is the mass of bottle before test period;W>;s she mass of botle after test period; andT is the test period in hours.

[0224] The tests are done in triplicate. The reported results are an average of three measurements.Rheological Measurement: Analysis Procedure for Hot-Melt Processing Capabilities

[0225] Analysis to determine viscosity was performed using a TA DHR-20 Rheometer in a parallel plate configuration. Heating and cooling were performed via Peltier plate. Samples were cylindrical with 1 mm thickness (height) and 25 mm in diameter. The rheological method was used to determine the viscosity in Pa*s.Method:Sample heated to 150 °C at a rate of 3 °C / min, then equilibrated for 180 sec.Sample oscillated at 100 rad / s and 150 °C for 60 sec.Sampled cooled to 25 °C, then equilibrated for 180 sec.

[0226] The viscosity (Pa*s) at 150 °C and 100 rad / s is related to the melt-flow viscosity of a material that is processed via gear pump through a tube at 150 °C and 100 rad / s. If the viscosity increases over the 60 seconds test period, it can be inferred that a material that is processed under these conditions will increase viscosity over time. Likewise, if the measured viscosity remains steady throughout the test period, a material is likely to be stable to the conditions and is considered processable. Additionally, materials with similar viscosities under the test conditions and do not significantly increase or decrease viscosity overtime, will behave similarly.Table 1. Chemical List.Acronym / Name Description SourceAcrylate PolymerRandom co-polymer of IOA / NVP (80:20)25 wt% in ethyl acetate Solventum Company, IOA / NVP in EAMaplewood, MN Tg > -52 °CRandom co-polymer of 2-EHA / NVP / ABP(85:14.8:0.2)2-EHA / NVP / ABP in Solventum Company,20 wt% in ethyl acetateEA Maplewood, MN Tg > -70 °CAcrylate Monomer2-ethylhexyl acrylateOA2-EHA n / aHomopolymer Tg = -70 °CIso-octyl acrylateCH3IOA n / a0Homopolymer Tg = -52 °C / V-vinyl lactam monomerN-vinyl pyrrolidoneNVP n / aHomopolymer Tg = 180 °CMonomer with Benzophenone for UV crosslinking4-(acryloyloxy)benzophenoneABP n / aHomopolymer Tg = n / aHydrocarbon CompoundMineral oil (USP)Mineral oils refined from petroleum crude oils arecomplex and variable mixtures of straight andbranched-chain paraffinic, naphthenic Cumberland Swan, (cycloparaffinic), having carbon numbers of 15 or Smyrna, TNmore with a melting point ofLess than -9°C and boiling points in the range of300-600°C.Petroleum jelly (USP)Petrolatum is obtained by dewaxing heavylubricating-oil stocks. It has a melting-point range TopCo Associates, Skokie, from 38° to 54° C. Chemically, petrolatum is a IL mixture of hydrocarbons, chiefly of the paraffinseries.Preperse Permethyl Polyisobutylene Presperse Inc. Somerset, 105A MW = 2300 Da NJPolyisobutyleneTPC595 TPC Group, Houston, TX MW = 1000 DaPlasticizerPolyester polyol: condensation of C36 dimerdiacid and C36 dimer diols Cargill BioIndustrial, PRIPLAST 3197Wayzata, MNHLB <5di-isopropyl dimer dilinoleatedi-isopropyl ester of C36 dimer diacid Lubrizol Corporation, DIPDDLWickliffe, OHHLB <5TackifierAromatic-modified C5 hydrocarbon resin Resin Solutions LLC, WingTack 86Mn = 650 Da Beaumont, TX Aromatic-modified C5 hydrocarbon resin Resin Solutions LLC, Wingtack STSMn = 1000 Da Beaumont, TX SolventSigma-Aldrich, St. Louis, XyleneMOSigma-Aldrich, St. Louis, HeptaneMOSigma-Aldrich, St. Louis, Methyl ethyl ketoneMOSiliconesPhenyl trimethicone Tris(trimethylsiloxy)-phenylsilane oligomer with AB Specialty Silicones, 20 a kinematic viscosity of 20 cSt. Waukegan, IL Wacker Chemical Phenyl trimethicone Tris(trimethylsiloxy)-phenylsilane polymer with aCorporation, Ann Arbor, 1000 kinematic viscosity of 1000 cSt.MICommercial ProductsTransparent and perforated polyethylene 3M Company,3M Transporesurgical tape with acrylate adhesive Maplewood, MNA woven fabric, non-elastic acrylate adhesive 3M Company,3M Duraporetape with silk-like acetate taffeta backing. Maplewood, MNA multi-purpose, hypoallergenic paper tape 3M Company,3M Microporewith acrylate adhesive that is gentle to skin Maplewood, MN3M Kind Removal Breathable, hypoallergenic medical tape with 3M Company, Silicone Tape silicone adhesive Maplewood, MN3M Nexcare A breathable, perforated acrylate adhesive tape 3M Company, Flexible Clear Tape with a clear, stretchy design Maplewood, MN AcResin ® A 260UV-curable acrylate adhesive prepolymer BASF, Schweiz, AG UVExamples 1-2: Organogel adhesive compositions for non-crosslinked PSAs

[0227] Organogel adhesive compositions for preparing pressure-sensitive adhesives having an acrylate polymer, a hydrocarbon compound, a plasticizer, each as described herein, were prepared. The components for the organogel adhesive compositions of Examples 1-2 are listed in Table 1A. Said components were combined and mixed to form a clear solution. The resulting mixture was solvent coated onto a 2 mil. polyester backing and dried at 77 °C for 5 minutes. The dried pressure-sensitive adhesive for each example were 1.5 mil thick. Table IB lists the component wt% within the dried pressure-sensitive adhesive. Silicone liners were found to be suitable as release materials for the constructions.Table 1A. Compositions for preparing non-crosslinked organogel pressure-sensitive adhesives EX I EX 2g gIOA / NVP(25% solids in 40 40ethyl acetate)Mineral oil 13 10Petroleum jelly — —Presperse— —Permethyl 105ATPC595 — 3Priplast 3197 7 7DIDDL — —Zinc oxide — —Heptane 20 20Propyl acetate 20 20Methyl ethyl— —ketoneTotal 100 100Table 1B. Non-crosslinked organogel pressure-sensitive adhesives (dried)EX I EX 2wt% wt%IOA / NVP33.3 33.3(non-crosslinked)Mineral oil 43.3 33.3Petroleum jelly — —Presperse— —Permethyl 105ATPC595 — 10Priplast 3197 23.3 23.3DIPDDL — —Zinc oxide — —Total 100 100UV cure N NE-beam cure N NComparative Examples 1-7: Organogel adhesive compositions for crosslinked PSAs

[0228] Organogel adhesive compositions for preparing crosslinked pressure-sensitive adhesives having an acrylate polymer, a hydrocarbon compound, a plasticizer, each as described herein, were prepared. The components for the organogel adhesive compositions of Comparative Examples 1-7 are listed in Table 2A. Said components were combined and mixed to form a clear solution. The resulting mixture was solvent coated onto a 2 mil. polyester backing and dried at 77 °C for 5 minutes. The dried pressure-sensitive adhesive for each example were 1-2.5 mil thick. Table 2B lists the component wt% within the dried pressure-sensitive adhesive. The dried pressure sensitive adhesives were UV cured under a 300W / in Fusion UV lamp using 2 passes at 50fpm to cross-link the arylate polymer to form the cross-linked acrylate polymer, unlike_Examples 1-2. Silicone liners were found to be suitable as release materials for the constructions.Comparative Examples 8-9: Organogel adhesive compositions for crosslinked PSAs

[0229] Comparative Examples 8-9 were prepared in the same manner as Comparative Examples 1-7 above; however, the samples were cured via E-beam at the designated dosage. Table 2A lists the compositions for preparing the organogel pressure-sensitive adhesives and Table 2B lists the organogel pressure-sensitive adhesives.Comparative Example 10: No hydrocarbon compound

[0230] Comparative Example 10 was prepared in the same manner as Comparative Examples 8-9. Comparative Example 10 differs from Comparative Examples 8-9 in that it does not include a hydrocarbon compound as described herein. Table 2A lists the compositions for preparing the organogel adhesives and Table 2B lists the organogel pressure-sensitive adhesives.Comparative Example 11 and Comparative Example 12: Further including silicone

[0231] Comparative Example 11 and Comparative Example 12 were each prepared in the same manner as Comparative Examples 1-7; however, each of Comparative Example 11 and Comparative Example 12 further include a silicone polymer. Comparative Example 11 and Comparative Example 12 differ from one another in the type of silicone polymer - Comparative Example 11 has a silicone of lower molecular weight / viscosity than Comparative Example 12. Table 2C lists the organogel pressure-sensitive adhesives.Comparative Examples 13-17

[0232] Comparative Examples 13-17 are commercially-available medical articles having a pressure-sensitive adhesive. Table 2D lists said medical articles.Table 2A. Compositions for preparing crosslinked organogel pressure-sensitive adhesives CE 10 (no CE CE 1 CE 2 CE 3 CE 4 CE 5 CE 7 CE 8 CE 9 hydro6carbon ) 2- EHA / NVP / ABP41.7 41.7 41.7 41.7 41.7 41.7 41.7 41.7 41.7 41.7 (20% solids inethyl acetate)Mineral oil 8.3 — — 8.3 — 8.3 8.3 8.3 — — Petroleum jelly — 8.3 — — 11.7 — — — — — Presperse— — 8.3 — — — — — — — Permethyl 105ATPC595 — — — — — — — — 8.3 —Priplast 3197 4.2 4.2 4.2 4.2 5.0 8.3 8.3 8.3 8.3 — DIDDL 4.2 4.2 4.2 4.2 — — — — — 16.7Zinc oxide — — — 0.25 — — — — Heptane 25.0 25.0 25.0 25.0 25.0 25.0 25.0 25.0 25.0 25.0 Methyl ethyl16.6 16.6 16.6 16.35 16.6 16.7 16.7 16.7 16.7 16.6 ketoneTotal 100 100 100 100 100 100 100 100 100 100Table 2B. Crosslinked organogel pressure-sensitive adhesives (dried)CE 10 (no CE 1 CE 2 CE 3 CE 4 CE 5 CE 6 CE 7 CE 8 CE 9hydrocarbon) 2- EHA / NVP / ABP 33.3 33.3 33.3 33.0 33.3 33.4 33.4 33.4 33.4 33.3 (cross-linked)Mineral oil 33.1 — — 32.8 — 33.3 33.3 33.3 — — Petroleum jelly — 33.1 — — 46.7 — — — — — Presperse— — 33.1 — — — — — — — Permethyl 105ATPC595 — — — — — — — — 33.3 —Priplast 3197 16.8 16.8 16.8 16.6 20 33.3 33.3 33.3 33.3 — DIPDDL 16.8 16.8 16.8 16.6 — — — — — 66.7Zinc oxide — — — 1.0 — — — — — —Total 100 100 100 100 100 100 100 100 100 100UV cure Y Y Y Y Y Y Y N N N E-beam cure N N N N N N N Y Y YTable 2C. Organogel crosslinked pressure-sensitive adhesives with silicones (dried)CE 11 CE 12(nohydrocarbon)2-EHA / NVP / ABP33.3 33.3(crosslinked)Mineral oil 33.3 —PRIPLAST 3197 16.7 16.7DIPDDL — 16.7Phenyl trimethicone 20 16.7 —Phenyl trimethicone 1000 — 33.3Total 100 100UV cure Y YE-beam cure N NTable 2D. Commercial Comparative Examples 13-17Transparent and perforated polyethylene surgical CE 13 3M Transporetape with acrylate adhesiveA woven fabric, non-elastic acrylate adhesive tape with CE 14 3M Duraporesilk-like acetate taffeta backing.A multi-purpose, hypoallergenic paper tape with CE 15 3M Microporeacrylate adhesive that is gentle to skin Breathable, hypoallergenic medical tape with silicone CE 16 3M Kind Removal Silicone TapeadhesiveA breathable, perforated acrylate adhesive tape with a CE 17 3M Nexcare Flexible Clear Tapeclear, stretchy designProperty Testing of Examples 1-2 and Comparative Examples 1-17

[0233] Examples 1-2 and Comparative Examples 1-17 were tested for peak value, debonding energy, and displacement at bonding according to the Tack Test above. The results are tabulated in Table 3. Each of Examples 1-2 provided excellent adhesive properties, despite not being crosslinked, and were surprisingly comparable to the crosslinked compositions of Comparative Examples 1-9 and the commercial articles of Comparative Examples 13-16. Comparative Example 10, on the other hand, had higher than desired peak values and debonding energies. As these values increase, removal could cause disruption of the substrate resulting in poor re-adhesion.

[0234] Examples 1-2 and Comparative Examples 1-5, 10, 11, 12, 14, 15, and 17 were further tested for re-application according to the Re-application Test above. The results are also tabulated in Table 3. Examples 1-2 and Comparative Examples 1-4 were able to be removed and reapplied atleast 20 times without causing injury to the skin surface or compromising the integrity of the organogel pressure-sensitive adhesive. Conversely, Comparative Example 5 did not perform well in the reapplication test, despite having good adhesive properties. Without wishing to be bound by theory, this observation was likely due to blooming of the hydrocarbon compound due to an inadequate ratio of hydrocarbon compound and plasticizer. Comparative Examples 11, 12, 14, 15, and 17 caused skin surface disruptions and loss of adhesion, thereby preventing these constructions from being reapplied.

[0235] Comparative Examples 6-7 were further tested for moisture vapor transmission rate (MVTR) according to the MVTR Test above. The results are also tabulated in Table 3. Surprisingly, these adhesives have very high MVTR (>600 g / m2 / 24 hours) despite being highly non-polar. Although the non-crosslinked examples (i.e., Examples 1 and 2) were not tested for MVTR, it is expected that they would also have excellent values.Table 3. Properties of pressure-sensitive adhesivesuv No.MVTcure* E- Adhesive Peak Debondin Displacemen successfulTap R (No. of beam thicknes valu g energy t at bonding ree g / m2passes cure s e (g) (g.s) (mm) application24 h ) sNon-crosslinked PSAsEX I — — 1.5 mil 54.6 9.3 1.7 20 n / a EX 2 — — 1.5 mil 44.3 6.7 1.0 20 n / a Crosslinked PSAsCE 1 2 — 1.5 mil 37.3 10.5 1.06 20 n / a CE 2 2 — 1.5 mil 54.0 15.8 1.79 20 n / a CE 3 1 — 1.5 mil 36.8 6.0 0.86 20 n / a CE 4 2 — 1.5 mil 24.2 12.0 1.04 20 n / a CE 5 2 — 1.5 mil 38.9 9.8 0.96 1 n / a CE 6 2 — 1 mil n / a n / a n / a n / a 4528 CE 7 2 — 2.5 mil n / a n / a n / a n / a 115710CE 8 — MRa 2 mil 50.3 12.2 0.94 n / a n / a d12CE 8 — MRa 2 mil 44.6 7.8 0.64 n / a n / a d14CE 8 — MRa 2 mil 36.4 6.4 0.56 n / a n / a d10CE 9 — MRa 2 mil 63.8 17.1 1.04 n / a n / a d14CE 9 — MRa 2 mil 59.6 16.0 0.86 n / a n / a dNo hydrocarbon compound crosslinked PSAs10CE MRa 2 mil 81.4 27.4 1.52 n / a n / a 10d14CE MRa 2 mil 77.0 24.0 1.13 n / a n / a 10dCrosslinked PSAs with siliconeCE2 — 1.5 mil 31.3 9.7 0.98 20 n / a 11CE1 — 1.5 mil 55.3 9.0 0.95 3 n / a 12Commercial PSAsCE— — — 68.3 12.2 0.41 n / a n / a 13CE— — — 34.8 16.5 0.70 1 n / a 14CE— — — 40.8 7.0 0.34 1 n / a 15CE— — — 36.9 10.4 0.83 n / a n / a 16CE— — — — — — 1 n / a 17* 300 W / in. fusion lamp at 50 fpmComparative Examples 18-19: Crosslinked PSAs with tackifier

[0236] Organogel adhesive compositions for preparing pressure-sensitive adhesives having an acrylate polymer, hydrocarbon compound, a plasticizer, and a tackifier, as described herein, were prepared. The components for Comparative Examples 18-19 are listed in Table 4A. Said components were combined and mixed to form a clear solution. The resulting mixture was solvent coated onto a 2 mil. polyester backing and dried at 77 °C for 5 minutes. The dried pressure-sensitive adhesive for each example were 2 mil thick. Table 4B lists the component wt% within the dried pressure-sensitive adhesive. The dried pressure sensitive adhesives were UV cured under a 300W / in Fusion UV lamp using 2 passes at 50fpm to cross-link the acrylate polymer to form the cross-linked acrylate polymer. Silicone liners were found to be suitable as release materials for the constructions.

[0237] Comparative Examples 18-19 differ from the Examples above in that they further include a tackifier. Although non-crosslinked compositions with tackifier were not prepared, it is reasonable to assume that including a tackifier in non-crosslinked compositions would be successful in view of Comparative Examples 18-19.Comparative Examples 20-21: Crosslinked PSAs with tackifier, without hydrocarbon and without plasticizer

[0238] Comparative Examples 20-21 were prepared according to the preparations of Comparative Examples 18-19 above (see Tables 4A and 4B). Each of said comparatives do not include a hydrocarbon compound or a plasticizer, as defined herein. Rather, Comparative Examples 20-21 only include the cross-linked acrylate polymer and a tackifier.Table 4A. Compositions for preparing crosslinked organogel adhesive composition with tackifierCE 18 CE 19 CE 20 CE 212- EHA / NVP / ABP 47.7 47.7 47.95 47.95 inEAMineral oil 8.34 8.34 — —Wingtack 86 4.17 — 4.09 —Wingtack STS — 4.17 — 4.09Priplast 3197 4.17 4.17 — —Heptane 16.62 16.62 19.18 19.18Xylene 25.0 25.0 28.77 28.77Total 100 100 100 100Table 4B. Crosslinked organogel pressure-sensitive adhesives with tackifier (dried)CE 18 CE 19 CE 20 CE 212- EHA / NVP / ABP 36 36 70 70(cross-linked)Mineral oil 32 32 — —Wingtack 86 16 — 30 —Wingtack STS — 16 — 30Priplast 3197 16 16 — —Total 100 100 100 100UV cure Y Y Y YE-beam cure N N N NProperty Testing of Comparative Examples 18-19 and Comparative Examples 20-21

[0239] The tape constructions having the pressure-sensitive adhesives of Table 4B were tested for peak value, debonding energy, and displacement at bonding according to the Tack Test above. The results are tabulated in Table 4C below.

[0240] The results indicate that adding a tackifier to the compositions does not compromise the adhesive characteristics. Comparative Examples 18-19 retain good tack, debonding energy, and holding power. Comparative Examples 20-21 behave like traditional PSAs with high tack and debonding energy but have lower dissipation.

[0241] Comparative Examples 18-19 and Comparative Examples 20-21 were not tested for reapplication.

[0242] Although the non-crosslinked organogel PSAs were not prepared with tackifier, these comparative examples serve as proof-of-concept that tackifiers may readily be incorporated into noncrosslinked organogel PSAs.Table 4C. Properties of pressure-sensitive adhesives having a tackifierUV Adhesiv No.Peak Displacementcure* E-beam e Debonding successful Tape value at bonding(No. of cure thicknes energy (g.s) re(g) (mm)passes) s applications CE 18 2 — 2 mil 52.5 11.6 0.8 n / a CE 19 2 — 2 mil 53.0 11.4 0.76 n / a CE 20 2 — 2 mil 114.0 21.1 0.31 n / a CE21 2 — 2 mil 105.3 23.2 0.35 n / aComparative Examples 22-24: Inclusion of quaternary ammonium antimicrobial agents within crosslinked organogel PSAs

[0243] Solubility Screening. It is important to note that neither benzalkonium chloride nor octenidine hydrochloride are soluble in mineral oil. Screening tests were conducted to determine the solubility of solid benzalkonium chloride and octenidine hydrochloride in the liquid phase (i.e., hydrocarbon compound and plasticizer) of the adhesive composition. The screening involved dissolving the antimicrobial at 25% w / w in methoxyisopropanol and adding an appropriate amount of these solutions to a blend of 43% Priplast 3197 and 57% mineral oil to obtain a 0.17% solution of benzalkonium chloride and 0.285% solution of octenidine dihydrochloride. Each solution was placed on a hotplate equipped with a magnetic stirrer and heated to 80 °C to flash off the methoxyisopropanol. The Priplast / mineral oil blends with the antimicrobials were then individually applied to glass slides and observed in thin sections for transparency and clarity. Both solutions were transparent, though the octenidine solution showed a slight translucency. The results demonstrated the feasibility of solvating these antimicrobials in the liquid phase, and ultimately, within the organogel PSA. In other words, the plasticizer allowed for benzalkonium chloride and octenidine hydrochloride to be incorporated into a ‘solvent’ (i.e., the hydrocarbon compound) that was otherwise incompatible.

[0244] It is important to further note that neither benzalkonium chloride nor octenidine hydrochloride are miscible with the acrylate polymer. As will be shown below, each antimicrobial agent is solubilized within the organogel PSA due to the presence of the plasticizer.

[0245] The components for the organogel adhesive compositions of Comparative Examples 22-24 are listed in Table 5A. Said components were combined and mixed to form a clear solution. The resulting mixture was solvent coated onto a 2 mil. polyester backing and dried at 77 °C for 5 minutes. The dried pressure-sensitive adhesive for each example were 1.0 mil thick. Table 5B lists the component wt% within the dried pressure-sensitive adhesive. The dried pressure sensitive adhesives were UV cured under a 300W / in Fusion UV lamp on a conveyor belt at a speed of 15 fpm to cross-linkthe arylate polymer to form the cross-linked acrylate polymer. The resulting construction was then laminated to a silicone release liner.

[0246] Comparative Examples 22 and 23 include an antimicrobial agent - benzalkonium chloride and octendine hydrochloride, respectively. Comparative Example 24 does not include an antimicrobial agent as a control. The antimicrobial activity of Examples 13-15 was tested in a timekill method adapted from AATCC Test Method 100-2012, as follows:1. All steps are performed with autoclaved and / or 70% IPA treated tools and materials.2. In triplicate, cut out 1 inch circles of adhesive using a punch die and remove liner using forceps. Place adhesive side up in a petri dish.3. Place 50 uL of a liquid overnight culture of S. aureus 6538 diluted to ~10A8 CFU / mL in 3-5 drops onto the adhesive. Place at 37C in a humidified incubator. Separate triplicates are incubated for 3 hours and 24 hours each.4. Make serial dilutions and plate on appropriate agar the inoculating culture called the "numbers control".5. After incubation, place the adhesive circle in 20 mL of DE neutralizing media and vortex for 1 minute to remove the bacterial challenge from the adhesive.6. Perform serial dilutions of the recovered samples and plate on appropriate agar plates.7. Count colonies on plates with between 20-200 colony forming units.8. Calculate the log reduction based on the change of recovered bacteria in the sample compared to the numbers control. Any samples that do not have recovery on 1 mL of recovered sample directly plated (no dilution) will be considered as having 1 CFU, in order to calculate the log reduction.

[0247] The results of the antimicrobial assay are provided in Table 5C.Table 5A. Compositions for preparing crosslinked organogel pressure-sensitive adhesives with antimicrobial agentsCE 24CE CE 23 (no22AA)g g g2- EHA / NVP / ABP10 10 10(20% solids inethyl acetate)Mineral oil 2.66 2.66 2.66Petroleum jelly — — —Presperse— — —Permethyl 105ATPC595 — — —Priplast 3197 2 2 2DIDDL — — —Zinc oxide — — —BAC (25% inmethoxyisoprop 0.032 —anol)OCT (25% inmethoxyisoprop 0.053 —anol)Heptane 4 4 4Methyl ethyl— — —ketoneTotal 18.7 18.7 18.7Table 5B. Crosslinked organogel pressure-sensitive adhesives (dried) with antimicrobial agents CE 24CE 22 CE 23 (noAA)wt% wt% wt%2- EHA / NVP / ABP 30 30 30(cross-linked)Mineral oil 39.88 39.8 40Petroleum jelly — — —Presperse— — —Permethyl 105ATPC595 — — —Priplast 3197 30 30 30DIPDDL — — —Zinc oxide — — —BAC 0.12 — —OCT — 0.2 —Total 100 100 100UV cure Y Y YE-beam cure N N NTable 5C. Antimicrobial activity of organogel pressure-sensitive adhesivesCE 24CE 22 CE 23 (noAA)Average Log0.82 0.83 0.04Reduction 3 hAverage Log5.78 5.78 0.04Reduction 24 h** Average Log6.26 6.25 7.04Recovery 3 h** Average Log1.30 1.30 7.04Recovery 24 h**Numbers control = 7.08

[0248] Comparative Examples 22 and 23 exhibited high levels of antibacterial activity against S. aureus. The increase in kill at 24 h compared to 3 h is indicative of a sustained release of antimicrobial from the adhesive.

[0249] Although the non-crosslinked organogel PSAs were not prepared with quaternary ammonium salts, these comparative examples serve as proof-of-concept that such antimicrobials may readily be incorporated into non-crosslinked organogel PSAs.Example 3 and Comparative Examples 25-26: Viscosity Observations and Hot-Melt Processing

[0250] Example 3 and Comparative Examples 25 and 26 were tested for viscosity (Pa*s), according to the rheological procedure above. Comparative Example 25 is a non-organogel version of Example 3 and cannot be hot-melt processed. Comparative Example 26 is a known adhesive (AcResin®) which is readily processable via drum unloader and / or gear pump at 150 °C (i.e., hot-melt processing).

[0251] The pressure-sensitive adhesive compositions are described in Table 6A.Table 6A. Organogel and non-organogel PSA compositionsEX 3 CE 25 CE 26wt% wt%2-EHA / NVP / ABP(not cross-linked)Intrinsic viscosity =33.4 1001.75AcResin®No chain transferagentsMineral oil 33.3 —Priplast 3197 33.3 —Total 100 100 100

[0252] Example 3 and Comparative Examples 25-26 were tested for viscosity (Pa*s), according to the rheological method above. The viscosity results for Example 3 and Comparative Examples 25-26 are tabulated in Table 6B.Table 6B. Viscosities of organogel vs non-organogel pressure-sensitive adhesives Viscosity (Pa*s)EX 3 1.1CE 25 140.1CE 26 AcResin® 20.4

[0253] Example 3 displayed a viscosity significantly below the viscosity of Comparative Example 26, which demonstrates that Example 3 can be readily processed with a drum unloader since it has been established that Comparative Example 26 can be hot-melt processed. Comparative Example 25 displayed a viscosity significantly greater than Comparative Example 26 and is therefore not processable via drum unloader.Comparative Example 27 and Comparative Example 28: Gamma sterilization

[0254] Comparative Example 27 (crosslinked organogel pressure-sensitive adhesive): A 37% solids composition of 30 wt% poly (2-ethylhexyl acrylate / N-vinyl pyrrolidone / acryloxy benzophenone)(85 / 15 / 0.4), 30 wt% mineral oil, 30 wt% Priplast 3197, 10 wt% polyisobutylene) in heptane / ethyl acetate was obtained, knife-coated onto a silicone release liner, and dried at 77 °C for 5 minutes to afford a 1.5 mil. thick pre-crosslinked organogel pressure-sensitive adhesive. The precrosslinked organogel pressure-sensitive adhesive was then laminated to a 0.8 mil. thick thermoplastic polyurethane backing and the resulting construction was UV-crosslinked through the adhesive face by exposure to a Fusion UV lamp at 300W / in. power on a conveyor belt at a speed of 15 fpm. A portion of the article was subjected to 33kGy of gamma irradiation.

[0255] Comparative Example 28 (standard pressure-sensitive adhesive): A solvent-based 97 / 3 poly(Isooctyl acrylate / acrylamide) composition was knife coated on a silicone release line and dried at 77 °C for 5 minutes to afford a 1 mil. thick adhesive. The adhesive was then laminated to a 0.8 mil. thick thermoplastic polyurethane backing. A portion of this polyurethane backed adhesive on silicone liner was subjected to 25kGy of gamma irradiation.

[0256] Comparative Example 27 and Comparative Example 28 were tested for immediate tack of the adhesive (peak value, the maximum force during retraction for primary peak) and the work of adhesion (debonding energy, area under the curve from initiation of retraction to debonding), as outlined in the Tack Test Procedure above, before gamma sterilization and after gamma sterilization. The results are provided in Table 7.Table 7. Properties Pre- and Post-SterilizationPeak Value (g) Debonding Energy (g.s) Before gamma After gamma Before gamma After gamma sterilization sterilization sterilization sterilization CE 27 45 ± 3.6 60 ± 4.4 7.19 ± 0.42 7.16 ± 0.61 CE 28 45 ± 3.6 42 ± 7.6 21.6 ± 2.45 14.9 ± 0.72

[0257] Gamma irradiation typically causes a reduction in adhesion strength due to additional crosslinking caused by the irradiation, as evidenced by the results of Comparative Example 28. Conversely, adhesion increases after gamma irradiation for the organogel pressure-sensitive adhesives of the present disclosure. Without wishing to be bound by theory, it is presumed that the dilution of the polymer chains within the organogel pressure-sensitive adhesive of Comparative Example 27 may prevent further cross-linking upon exposure to gamma irradiation. Further, the results show that debonding energy is unaffected by gamma irradiation in Comparative Example 27, unlike Comparative Example 28.

[0258] Although the non-crosslinked organogel PSAs were not tested, these comparative examples serve as proof-of-concept that organogel PSAs are resistant to detrimental effects during sterilization under gamma irradiation.EQUIVALENTSThose skilled in the art will recognize, or be able to ascertain, using no more than routine experimentation, numerous equivalents to the specific embodiments described specifically herein. Such equivalents are intended to be encompassed in the scope of the following claims.

Claims

1. What is claimed is:

1. An organogel pressure-sensitive adhesive comprising:a non-crosslinked acrylate polymer,the non-crosslinked acrylate polymer characterized by a glass-transition temperature of at least -70 °C, andthe non-crosslinked acrylate polymer derived from:one or more alkyl (alk)acrylate monomer characterized by a homopolymer glass transition temperature of about -100 °C to about -25 °C; andone or more polar monomer characterized by a homopolymer glass transition temperature of at least 0 °C,wherein the one or more polar monomer is present within the non-crosslinked acrylate polymer in an amount of at least 20 mol% based on the total molar amount of the non-crosslinked acrylate polymer;at least one hydrocarbon compound; anda plasticizer characterized by:an HLB value of no greater than 5, anda molecular weight of at least 400 Da, anda glass transition temperature of less than 0 °C,wherein at least 60 wt% of components of the organogel pressure-sensitive adhesive, excluding solvents, are characterized as liquids at 25 °C at 101 kPa,wherein wt% is with respect to the weight of the organogel pressure-sensitive adhesive.

2. The organogel pressure-sensitive adhesive of claim 1, characterized by a viscosity of no greater than 30 Pa*s according to the Rheological Measurement.

3. The organogel pressure-sensitive adhesive of any one of the preceding claims, the non-crosslinked acrylate polymer characterized by a molecular weight of about 100 kDa to about 1500 kDa.

4. The organogel pressure-sensitive adhesive of any one of the preceding claims, the non-crosslinked acrylate polymer excluding hydroxyl groups.

5. The organogel pressure-sensitive adhesive of any one of the preceding claims, the non-crosslinked acrylate polymer excluding being derived from chain transfer agents.

6. The organogel pressure-sensitive adhesive of any one of the preceding claims, the noncrosslinked acrylate polymer characterized by an inherent viscosity of about 1.2 dL / g to about 2.0 dL / g.

7. The organogel pressure-sensitive adhesive of any one of the preceding claims, the noncrosslinked acrylic polymer present in an amount of about 20 wt% to about 50 wt% with respect to the weight of the organogel pressure-sensitive adhesive.

8. The organogel pressure-sensitive adhesive of any one of the preceding claims, the noncrosslinked acrylic polymer present in an amount of no more than 40 wt% with respect to the weight of the organogel pressure-sensitive adhesive.

9. The organogel pressure-sensitive adhesive of any one of the preceding claims, the noncrosslinked acrylic polymer present in an amount of about 25 wt% to about 33 wt% with respect to the weight of the organogel pressure-sensitive adhesive.

10. The organogel pressure sensitive adhesive of any one of the preceding claims, the noncrosslinked acrylic polymer present in an amount relative to the at least one hydrocarbon compound in a weight ratio ofabout 0.5:l to about 2.5:l.

11. The organogel pressure-sensitive adhesive of any one of the preceding claims, the noncrosslinked acrylic polymer present in an amount relative to the plasticizer in a weight ratio of about 0.5:1 to about 2:1.

12. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more alkyl (alk)acrylate monomer characterized by a molecular weight of about 50 Da to about 200 Da.

13. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more alkyl (alk)acrylate monomer represented by Formula I:R1-OC(O)-C(R2)=CH2(I),wherein:R1is a straight or branched C4-C20 alkyl or a Ce-Cn alkcycloalkyl, andR2is -H or C1.4 alkyl.

14. The organogel pressure-sensitive adhesive of any one of the preceding claims, wherein R1is a G-C12 alkyl.

15. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more alkyl (alk)acrylate monomer selected from 2-ethylhexyl acrylate, isooctyl acrylate, n-butyl acrylate, cyclohexyl acrylate, and a combination thereof.

16. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more alkyl (alk)acrylate monomer being about 60 wt% to about 90 wt% of the weight of the noncrosslinked acrylate polymer.

17. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more alkyl (alk)acrylate monomer and the one or more polar monomer present in the non-crosslinked acrylate polymer in a weight ratio of about 9: 1 to about 1.5: 1.

18. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more alkyl (alk)acrylate monomer and the one or more polar monomer present in the non-crosslinked acrylate polymer in a mole ratio of about 4: 1 to about 0.5:1.

19. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more polar monomer characterized by a homopolymer glass transition temperature of about 0 °C to about 180 °C.

20. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more polar monomer characterized by a molecular weight of about 100 Da to about 150 Da.

21. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more polar monomer characterized by a Log P value of about 0.3 to about 0.5.

22. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more polar monomer selected from an (alk)acrylic acid monomer, a (alk)acrylamide monomer, an alkylamino (alk)acrylate, an \ -vinvl lactam monomer, a vinyl ester monomer, a vinyl amide monomer, a vinyl ether monomer, a vinyl aryl monomer, and a vinyl heteroaryl monomer.

23. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more polar monomer being a \ -viny I lactam monomer.

24. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more polar monomer selected from \ -vinvlpyrrolidonc. methyl. A -■v nylpyrrotidooe, and N-vinylcaprolactam.

25. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more polar monomer being about 10 wt% to about 40 wt% of the weight of the non-crosslinked acrylate polymer.

26. The organogel pressure-sensitive adhesive of any one of the preceding claims, the one or more polar monomer being present in amount of about 20 mol% to about 55 mol% of the total molar amount of the non-crosslinked acrylate polymer.

27. The organogel pressure-sensitive adhesive of any one of the preceding claims, the non-crosslinked acrylate polymer derived from:2-ethylhexyl acrylate, isooctyl acrylate, or a combination thereof; and-vinyl pyrrolidone.

28. The organogel pressure-sensitive adhesive of any one of the preceding claims, the non-crosslinked acrylate polymer being further derived from one or more high Tg alkyl (alk)acrylate monomer characterized by a homopolymer glass transition temperature of about -25 °C to about 200 °C, the one or more high Tg alkyl (alk)acrylate monomer being present in an amount of no greater than about 20 wt% of the weight of the non-crosslinked acrylate polymer.

29. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon compound characterized by a molecular weight of about 200 Da to about 700 Da.

30. The organogel pressure-sensitive adhesive of any one of claims 1-27, the at least one hydrocarbon compound being a polymer characterized by a molecular weight of about up to about 3000 Da.

31. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon compound characterized by a boiling point of at least 200 °C at 101 kPa.

32. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon comprising 15-50 carbon atoms.

33. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon comprising 15-18 carbon atoms.

34. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon being one or more components of mineral oil.

35. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon being one or more components of petroleum jelly.

36. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon compound being a polymer.

37. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon being a polyisobutylene polymer.

38. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon compound present in an amount of about 20 wt% to about 50 wt% with respect to the weight of the organogel pressure-sensitive adhesive.

39. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon compound present in an amount relative to the plasticizer in a weight ratio of about 0.5:1 to about 3:1.

40. The organogel pressure-sensitive adhesive of any one of the preceding claims, the at least one hydrocarbon compound being void of one or more of: heteroatom-containing functional groups, polymerizable groups, and polycyclic aromatic hydrocarbon groups.

41. The organogel pressure-sensitive adhesive of any one of the preceding claims, the plasticizer characterized as a liquid at 25 °C at 101 kPa.

42. The organogel pressure-sensitive adhesive of any one of the preceding claims, the plasticizer characterized by a molecular weight of about 1500 Da to about 3500 Da.

43. The organogel pressure-sensitive adhesive of any one of the preceding claims, the plasticizer characterized by a glass transition temperature of about -100°C to about 0 °C.

44. The organogel pressure-sensitive adhesive of any one of the preceding claims, excluding plasticizing components characterized by an HLB value greater than 5.

45. The organogel pressure-sensitive adhesive of any one of the preceding claims, the plasticizer being a polyester polyol.

46. The organogel pressure-sensitive adhesive of any one of the preceding claims, the plasticizer being a polyester polyols derived from dimerized fatty acids, dimerized fatty alcohols, or a combination thereof.

47. The organogel pressure-sensitive adhesive of any one of the preceding claims, the plasticizer represented by one or more compound of Formula III:R9-A-R11-B-R10(IV),wherein:R9and R10are each independently selected from a straight or branched C1-C40 alkyl optionally substituted with -OH or -CO2R12, a straight or branched C1-C40 alkenyl optionally substituted with -OH or -CO2R12, a C8-C40 alkcycloalkyl optionally substituted with -OH or -CO2R12, and a C8-C40 alkcycloalkenyl optionally substituted -OH or -CO2R12,R11is a straight or branched C8-C40 alkylene, a straight or branched C8-C40 alkenylene, a C8-C40 alkcycloalkylene, or a C8-C40 alkcycloalkenylene,R12is -H or a C1-C4 alkyl, andA and B are independently selected -OC(O)-, -C(O)O-, -NHC(O)-, -C(O)NH-, and -O-.

48. The organogel pressure-sensitive adhesive of any one of the preceding claims, the plasticizer is present in an amount of about 30 wt% to about 55 wt% with respect to the weight of the organogel pressure-sensitive adhesive.

49. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier.

50. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier characterized by a molecular weight of at least 700 Da.

51. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifer characterized by a glass transition temperature of at least 25 °C.

52. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifer characterized by an HLB value of no greater than 5.

53. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier characterized as a solid at 25 °C and 101 kPa.

54. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier, the tackifier being an unsaturated hydrocarbon polymer.

55. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier, the tackifier being a polymer derived from one or more 1,3 diene monomer and one or more aromatic monomer.

56. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier, the tackifier being a polymer derived from one or more 1,3 diene monomer having 5, 10, 15, or 20 carbon atoms.

57. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier, the tackifier being a polymer derived from one or more aromatic monomer selected from styrene, α-methyl styrene, and vinyl toluene.

58. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier, the tackifier present in an amount of no greater than 40 wt%.

59. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier, the tackifier present in an amount of about 1 wt% to about 25 wt% with respect to the weight of the organogel pressure-sensitive adhesive.

60. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier, the tackifier and the non-crosslinked acrylate polymer being present in a weight ratio of an about 1:0.25 to about 1:1.

61. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a tackifier, the tackifier and the at least one hydrocarbon compound present in a weight ratio of about 1:1 to about 1:3.

62. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising an antimicrobial compound.

63. The organogel pressure-sensitive adhesive of any one of the preceding claims, further comprising a silicone polymer characterized by a viscosity of no greater than 1000 cSt.

64. The organogel pressure-sensitive adhesive of any one of claims 1-63, excluding silicone polymers.

65. A composition for preparing an organogel pressure-sensitive adhesive of any one of claims 1- 64, the composition comprising:one or more volatile solvent;the non-crosslinked acrylate polymer;the at least one hydrocarbon compound;the plasticizer; andoptionally a tackifier.

66. A composition for preparing an organogel pressure-sensitive adhesive of any one of claims 1- 64, the composition comprising:one or more volatile solvent;the one or more alkyl (alk)acrylate monomer;the one or more polar monomer;the at least one hydrocarbon compound;the plasticizer; andoptionally a tackifier.

67. A medical article comprising:a substrate; andan organogel pressure-sensitive adhesive of any one of claims 1-64.

68. The medical article of claim 67, the organogel pressure-sensitive adhesive being present on the substrate at a thickness of about 0.1 mil to about 5 mil.

69. A method for preparing an organogel pressure-sensitive adhesive of any one of claims 1-64, the method comprising:providing a composition comprising:an acrylate polymer prepared from the one or more alkyl (alk)acrylate monomer, and the one or more polar monomer,the at least one hydrocarbon compound,the plasticizer,a volatile solvent; andoptionally a tackifier; andremoving the volatile solvent.

70. A method for preparing an organogel pressure-sensitive adhesive of any one of claims 1-64, the method comprising:providing a composition comprising:the one or more alkyl (alk)acrylate monomer, and the one or more polar monomer, the at least one hydrocarbon compound,the plasticizer, andoptionally a tackifier; andsubjecting the composition to conditions effective to polymerize the one or more alkyl (alk)acrylate monomer and the one or more polar monomer.

71. A solvent-cast method for preparing a medical article, the solvent-cast method comprising:providing a composition of claim 65;providing a substrate;contacting the composition to the substrate; andremoving the one of more volatile solvent to form the medical article.

72. A hot-melt method for preparing a medical article, the hot-melt method comprising:providing an organogel pressure-sensitive adhesive of any one of claims 1-64 and a substrate; heating the organogel pressure-sensitive adhesive to form a heated pressure-sensitive adhesive; andcontacting the heated pressure-sensitive adhesive to the substrate to form the medical article.

73. A method of adhering a medical article of any one of claims 67-68 to a skin surface of a subject, the method comprising:contacting the organogel pressure-sensitive adhesive of the medical article to the skin surface of the subject.

74. A kit comprising:a composition of any one of claims 65-66; anda set of instructions directing a user to prepare a medical article.

75. A kit comprising:a medical article of any one of claims 67-68; anda set of instructions directing a user to contact the medical article to a skin surface.

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