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WO2025096322A1 - Compositions d'adhésifs sensibles à la pression et diverses applications associées - Google Patents

Compositions d'adhésifs sensibles à la pression et diverses applications associées Download PDF

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Publication number
WO2025096322A1
WO2025096322A1 PCT/US2024/053179 US2024053179W WO2025096322A1 WO 2025096322 A1 WO2025096322 A1 WO 2025096322A1 US 2024053179 W US2024053179 W US 2024053179W WO 2025096322 A1 WO2025096322 A1 WO 2025096322A1
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WO
WIPO (PCT)
Prior art keywords
article
pressure sensitive
sensitive adhesive
marking
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2024/053179
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English (en)
Inventor
Richard T. Skov
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Flexcon Co Inc
Original Assignee
Flexcon Co Inc
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Filing date
Publication date
Application filed by Flexcon Co Inc filed Critical Flexcon Co Inc
Publication of WO2025096322A1 publication Critical patent/WO2025096322A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/21—Paper; Textile fabrics
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F3/00—Labels, tag tickets, or similar identification or indication means; Seals; Postage or like stamps
    • G09F3/08—Fastening or securing by means not forming part of the material of the label itself
    • G09F3/10—Fastening or securing by means not forming part of the material of the label itself by an adhesive layer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
    • C09J2301/18—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet characterized by perforations in the adhesive tape
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/414—Additional features of adhesives in the form of films or foils characterized by the presence of essential components presence of a copolymer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2400/00—Presence of inorganic and organic materials
    • C09J2400/20—Presence of organic materials
    • C09J2400/26—Presence of textile or fabric
    • C09J2400/263—Presence of textile or fabric in the substrate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2431/00—Presence of polyvinyl acetate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2433/00—Presence of (meth)acrylic polymer

Definitions

  • the invention generally concerns pressure sensitive adhesive (PSA) compositions.
  • PSD pressure sensitive adhesive
  • the compositions can be capable of allowing a marking medium (e.g., an ink or a die) to flow through the composition without substantially laterally spreading out within the composition.
  • a marking medium e.g., an ink or a die
  • Pressure sensitive adhesives can be utilized in numerous industries and/or applications.
  • One illustrative, non-limiting example of an application for a pressure sensitive adhesive is in the medical field, specifically as an adhesive for an image guided biopsy grid in which the grid is markable with ink so that a subject’s skin underlying the grid/adhesive can be marked with ink to identify a needle entry target.
  • most adhesives would not allow the ink to bleed through, much less allow for the ink to bleed through and form on the skin a marking that has the same size and shape as the marking made on the image-guided biopsy grid. As such, most adhesives may be inappropriate for such an end use application where a fine point or marking on the subject’s skin is important for proper needle insertion in order to perform a delicate biopsy procedure.
  • the solution can include a pressure sensitive adhesive (PSA) composition that can be capable of allowing a marking medium (e.g., an ink) to flow through the PSA composition without substantially laterally spreading out within the composition (when the composition is in the form of a layer having a desired thickness (e.g., 1 mil to 20 mils or 2 mils to 15 mils, or 3 mils to 12 mils).
  • PSA pressure sensitive adhesive
  • the adhesive composition of the present invention is capable of allowing a marking medium (e.g., ink from a SHARPIE ® pen) to bleed though the adhesive composition and form a narrow focused line, rather than a broad wide line.
  • a marking medium e.g., ink from a SHARPIE ® pen
  • a marking can be made on the grid substrate, and the marking medium can flow through the grid substrate and flow through the adhesive composition of the present invention such that the marking on the grid substrate makes it to the skin in substantially the same size and shape as the marking on the grid.
  • the PSA compositions of the present invention can be used in other applications as well.
  • the PSA compositions of the present invention can be used in label or tape applications such that the label or tape includes a film or substrate (e.g., thermoplastic, thermoset, paper, woven or non-woven material film or substrate), an adhesive layer comprising the PSA of the present invention, and optionally a release liner, wherein the PSA is positioned between the film or substrate and the release liner.
  • a film or substrate e.g., thermoplastic, thermoset, paper, woven or non-woven material film or substrate
  • an adhesive layer comprising the PSA of the present invention
  • optionally a release liner wherein the PSA is positioned between the film or substrate and the release liner.
  • Such labels or tapes can be used on surfaces such as tools (e.g., hand or power tools), toolboxes, consumer durables (e.g., washers, dryers, refrigerators, washing machines, microwaves, etc.), automobiles (e.g., under the hood, in the cabin, and/or on an outer surface), electronics, and/or graphics for buildings (e.g., for stores, store windows, etc.), transportation vehicles (e.g., planes, trains, automobiles (e.g., trucks, cars, motorcycles), helicopters, etc.), and any other article of manufacture.
  • tools e.g., hand or power tools
  • toolboxes e.g., consumer durables (e.g., washers, dryers, refrigerators, washing machines, microwaves, etc.)
  • automobiles e.g., under the hood, in the cabin, and/or on an outer surface
  • electronics e.g., for buildings, for stores, store windows, etc.
  • transportation vehicles e.g., plane
  • a PSA composition can include an acrylicvinyl acetate copolymer, a tackifier, a plasticizer, and a solvent system (e.g., a solvent system having a boiling point of 175 °C to 250 °C).
  • the PSA composition can be capable of allowing a marking medium (e.g., an ink or dye) to flow through the composition without substantially laterally spreading out within the composition when the composition is in the form of a layer having a particular thickness (e.g., a thickness of 1 mil to 20 mils or any range or number therein (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 mils).
  • the PSA composition does not include openings that extend through the composition.
  • blowing agents are not used to form the PSA composition of the present invention.
  • the PSA composition can include: 55 wt. % to 95 wt. % of the aery lie- vinyl acetate copolymer; 3 wt. % to 30 wt. % of the tackifier; 1 wt. % to 12 wt. % of the plasticizer; and 0.1 wt. % to 4 wt. % of the solvent system.
  • the PSA composition can be cured and can include 0.1 wt. % to 2.5 wt.
  • % of a crosslinker e.g., an aluminum crosslinker
  • a crosslinker e.g., an aluminum crosslinker
  • the PSA composition can be uncured and can be free of the crosslinker.
  • the acrylic-vinyl acetate copolymer of the PSA composition can include, based on the total weight of the copolymer, 55 wt. % to 98 wt. % of acrylic units and 2 wt. % to 45 wt. % of vinyl acetate units.
  • the tackifier can include a hydrogenated rosin and/or rosin ester (e.g., a glycol or pentaerythritol based resin), the plasticizer can include a benzyl phthalate (e.g., isononyl benzyl phthalate), and the solvent system can include a dibasic ester (e.g., dimethyl adipate, dimethyl glutarate, or dimethyl succinate, or any combination thereof).
  • a hydrogenated rosin and/or rosin ester e.g., a glycol or pentaerythritol based resin
  • the plasticizer can include a benzyl phthalate (e.g., isononyl benzyl phthalate)
  • the solvent system can include a dibasic ester (e.g., dimethyl adipate, dimethyl glutarate, or dimethyl succinate, or any combination thereof).
  • such an article e.g., a label or tape, an image biopsy grid, etc.
  • an adhesive layer comprising a PSA composition according to the present invention.
  • the substrate can include a first surface and a second surface opposite the first surface
  • the adhesive layer can include a third surface and a fourth surface opposite the third surface (where the second surface is in contact with the third surface).
  • the article can include a release liner in contact with the fourth surface.
  • the substrate (e.g., a flexible substrate) of the article can include openings that extend through the first and second surfaces, and the adhesive layer of the article does not include openings.
  • the first side of the substrate can include a marking (e.g., including a plurality of lines spaced relative to each other to form a grid pattern). In a particular aspect, at least a portion of the plurality of lines has a line width of less than about 1/8 inch.
  • the substrate of such an article can be a non-woven layer (e.g., to allow a marking applied to the article to pass substantially directly through the article). In some aspects, such a non-woven layer can have a particular basis weight (e.g., about 2/5 oz/yd 2 to about 1 oz/yd 2 ), a particular thickness (e.g., less than about 25 mils), or a combination thereof.
  • an article can have a particular substrate thickness (e.g., 2 mils to 10 mils), a particular adhesive layer thickness (e.g., 0.1 mils to 5.0 mils), a particular article thickness (e.g., 2 mils to 14 mils), or any combination thereof.
  • a particular substrate thickness e.g., 2 mils to 10 mils
  • a particular adhesive layer thickness e.g., 0.1 mils to 5.0 mils
  • a particular article thickness e.g., 2 mils to 14 mils
  • a marking medium e.g., an ink or dye
  • the method can include marking (e.g., by applying an ink pen) a first portion of an article, where at least a second portion of the article is in contact with the person’s skin, and the marking medium (e.g., ink from the ink pen) passes through the first and second portions of the article and marks the person’s skin.
  • the first portion of the article e.g., the substrate
  • the marking on the skin can be substantially the same size and shape as the marking on the first portion of the article.
  • the method can include imaging a portion of the person’s body and article attached to the body, identifying a needle entry target in the first portion of the article with reference to one or more grid lines on a portion of the article, and marking the needle entry target with the marking medium so that the marking medium passes through the article and marks the needle entry target on the skin.
  • the method can include removing the article from the skin and inserting a biopsy needle substantially at the marked needle entry target on the skin.
  • PSA compositions are described that can include, based on the total weight of the composition, 55 wt. % to 95 wt. % of an acrylicvinyl acetate copolymer, 3 wt. % to 30 wt. % of a tackifier, 1 wt. % to 12 wt. % of a plasticizer, and 0.1 wt. % to 4 wt. % of a solvent system having a boiling point of 175 °C to 250 °C.
  • the PSA composition can be cured and can include 0.1 wt. % to 2.5 wt.
  • the PSA composition can be uncured and can be free of any crosslinker.
  • the acrylic-vinyl acetate copolymer of the PSA composition can include, based on the total weight of the copolymer, 55 wt. % to 98 wt. % of acrylic units and 2 wt. % to 45 wt. % of vinyl acetate units.
  • the tackifier can include a hydrogenated rosin and/or rosin ester (e.g., a glycol or pentaerythritol based resin), the plasticizer can include a benzyl phthalate (e.g., isononyl benzyl phthalate), and the solvent system can include a dibasic ester (e.g., dimethyl adipate, dimethyl glutarate, or dimethyl succinate, or any combination thereof).
  • the PSA composition does not include openings that extend through the PSA composition.
  • an article can include a substrate and an adhesive layer comprising such a PSA composition.
  • the substrate can include a first surface and a second surface opposite the first surface, and the adhesive layer can include a third surface and a fourth surface opposite the third surface (where the second surface is in contact with the third surface).
  • the article can include a release liner in contact with the fourth surface.
  • the substrate can include a flexible substrate.
  • the article can include a label or tape.
  • Aspect 1 is a pressure sensitive adhesive composition comprising: an acrylic-vinyl acetate copolymer; a tackifier; a plasticizer; and a solvent system having a boiling point of 175 °C to 250 °C, wherein the composition is capable of allowing a marking medium to flow through the composition without substantially laterally spreading out within the composition when the composition is in the form of a layer having a thickness of 3 mils to 12 mils.
  • Aspect 2 is the pressure sensitive adhesive composition of aspect 1, wherein the composition is cured and comprises: 55 wt. % to 95 wt. % of the acrylic-vinyl acetate copolymer; 3 wt.
  • Aspect 3 is the pressure sensitive adhesive composition of aspect 2, wherein the crosslinker is an aluminum containing crosslinker.
  • Aspect 4 is the pressure sensitive adhesive composition of any one of aspects 2 to 3, wherein the composition is in the form of a layer or film having a thickness of 3 mils to 12 mils.
  • Aspect 5 is the pressure sensitive adhesive composition of aspect 1, wherein the composition is uncured and comprises: 55 wt. % to 95 wt.
  • Aspect 6 is the pressure sensitive adhesive composition of any one of aspects 1 to 5, wherein: the acrylicvinyl acetate copolymer comprises 55 wt. % to 98 wt. % of acrylic units and 2 wt. % to 45 wt.
  • aspects 7 is the pressure sensitive adhesive composition of aspect 6, wherein: the hydrogenated rosin and/or rosin ester comprises a glycol or pentaerythritol based resin; the benzyl phthalate comprises isononyl benzyl phthalate; and the dibasic ester comprises dimethyl adipate, dimethyl glutarate, or dimethyl succinate, or any combination thereof.
  • Aspect 8 is the pressure sensitive adhesive composition of any one of aspects 1 to 7, wherein the marking medium includes an ink or dye.
  • Aspect 9 is the pressure sensitive adhesive composition of any one of aspects 1 to 8, wherein the pressure sensitive adhesive composition does not include openings that extend through the pressure sensitive adhesive composition.
  • Aspect 10 is an article comprising the pressure sensitive adhesive composition of any one of aspects 1 to 9.
  • Aspect 11 is the article of aspect 10, comprising: a substrate comprising a first surface and a second surface opposite the first surface; and an adhesive layer comprising the pressure sensitive adhesive composition, a third surface, and a fourth surface opposite the third surface, wherein the second surface is in contact with the third surface.
  • Aspect 12 is the article of aspect 11, wherein the article further comprises a release liner in contact with the fourth surface.
  • Aspect 13 is the article of any one of aspects 11 to 12, wherein the substrate is a flexible substrate.
  • Aspect 14 is the article of any one of aspects 11 to 13, wherein the substrate comprises a plurality of openings that extend through the first and second surfaces of the substrate and wherein the adhesive layer does not include a plurality of openings.
  • Aspect 15 is the article of any one of aspects 11 to 14, wherein the first side of the substrate comprises a marking.
  • Aspect 16 is the article of aspect 15, wherein the marking comprises a plurality of lines spaced relative to each other to form a grid pattern.
  • Aspect 17 is the article of aspect 16, wherein at least a portion of the plurality of lines has a line width of less than about 1/8 inch.
  • Aspect 18 is the article of any one of aspects 15 to 17, wherein the marking is at least partially a radiopaque marking.
  • Aspect 19 is the article of any one of aspects 15 to 18, wherein at least one of the plurality of openings extends through the marking.
  • Aspect 20 is the article of any one of aspects 11 to 19, wherein the adhesive layer covers at least about 30% of the surface area of the second side of the substrate.
  • Aspect 21 is the article of any one of aspects 11 to 20, wherein the substrate is a non-woven layer.
  • Aspect 22 is the article of aspect 21 , wherein the non-woven layer has a basis weight of about 2/5 oz/yd 2 to about 1 oz/yd 2 .
  • Aspect 23 is the article of any one of aspects 21 to 22, wherein the non-woven layer has a thickness of less than about 25 mils.
  • Aspect 24 is the article of any one of aspects 11 to 23, wherein: the substrate has a thickness of 2 mils to 10 mils; and the adhesive layer has a thickness of 0.1 mils to 5.0 mils.
  • Aspect 25 is the article of any one of aspects 10 to 24, wherein the article has a thickness of 2 mils to 14 mils.
  • Aspect 26 is the article of any one of aspects 10 to 25, wherein the article is configured to allow a marking applied to the article to pass substantially directly through the article.
  • Aspect 27 is the article of any one of aspects 10 to 26, wherein the article is a label or tape.
  • Aspect 28 is the article of any one of aspects 10 to 26, wherein the article is an image guided biopsy grid.
  • Aspect 29 is a method of marking a person’s skin with a marking medium, the method comprising marking a first portion of the article of any one of aspects 10 to 28, wherein at least a second portion of the article is in contact with the person’s skin, and wherein the marking medium passes through the first and second portions and marks the person’s skin.
  • Aspect 30 is the method of aspect 29, wherein the first portion is opposite the second portion.
  • Aspect 31 is the method of any one of aspects 29 to 30, wherein the marking on the skin is substantially the same size and shape as the marking on the first portion of the article.
  • Aspect 32 is the method of any one of aspects 29 to 31, wherein the marking medium includes an ink or dye.
  • Aspect 33 is the method of aspect 32, wherein the marking includes applying an ink pen to the first portion of the article.
  • Aspect 34 is the method of any one of aspects 29 to 33, wherein the first portion of the article comprises the substrate and the second portion of the article comprises the adhesive layer.
  • Aspect 35 is the method of any one of aspects 29 to 34, further comprising imaging a portion of the person’s body and article attached to the body, identifying a needle entry target in the first portion of the article with reference to one or more grid lines on a portion of the article, and marking the needle entry target with the marking medium so that the marking medium passes through the article and marks the needle entry target on the skin.
  • Aspect 36 is the method of aspect 35, further comprising removing the article from the skin and inserting a biopsy needle substantially at the marked needle entry target on the skin.
  • Aspect 37 is a pressure sensitive adhesive composition comprising: 55 wt. % to 95 wt. % of an acrylic-vinyl acetate copolymer; 3 wt. % to 30 wt. % of a tackifier; 1 wt. % to 12 wt. % of a plasticizer; and 0.1 wt. % to 4 wt. % of a solvent system having a boiling point of 175 °C to 250 °C.
  • Aspect 38 is the pressure sensitive adhesive composition of aspect 37, wherein the composition is cured and further comprises 0.1 wt. % to 2.5 wt. % of a crosslinker.
  • Aspect 39 is the pressure sensitive adhesive composition of aspect 38, wherein the crosslinker is an aluminum containing crosslinker.
  • Aspect 40 is the pressure sensitive adhesive composition of aspect 37, wherein the composition is uncured.
  • Aspect 41 is the pressure sensitive adhesive composition of any one of aspects 37 to 40, wherein: the acrylic-vinyl acetate copolymer comprises 55 wt. % to 98 wt. % of acrylic units and 2 wt. % to 45 wt. % of vinyl acetate units based on the total weight of the copolymer; the tackifier comprises a hydrogenated rosin and/or rosin ester; the plasticizer comprises a benzyl phthalate; and the solvent system comprises a dibasic ester.
  • Aspect 42 is the pressure sensitive adhesive composition of aspect 41 , wherein: the hydrogenated rosin and/or rosin ester comprises a glycol or pentaerythritol based resin; the benzyl phthalate comprises isononyl benzyl phthalate; and the dibasic ester comprises dimethyladipate, dimethyl glutarate, or dimethyl succinate, or any combination thereof.
  • Aspect 43 is the pressure sensitive adhesive composition of any one of aspects 37 to 42, wherein the pressure sensitive adhesive composition does not include openings that extend through the pressure sensitive adhesive composition.
  • Aspect 44 is an article comprising the pressure sensitive adhesive composition of any one of aspects 37 to 43.
  • Aspect 45 is the article of aspect 44, comprising: a substrate comprising a first surface and a second surface opposite the first surface; and an adhesive layer comprising the pressure sensitive adhesive composition, a third surface, and a fourth surface opposite the third surface, wherein the second surface is in contact with the third surface.
  • Aspect 46 is the article of aspect 45, wherein the article further comprises a release liner in contact with the fourth surface.
  • Aspect 47 is the article of any one of aspects 45 to 46, wherein the substrate is a flexible substrate.
  • Aspect 48 is the article of any one of aspects 44 to 47, wherein the article is a label or tape.
  • pen is includes without limitation any of various instruments for marking, writing or drawing with ink or a similar substance.
  • the pen has its own ink- source, and a tip made of porous, pressed fibers, such as felt.
  • marking medium includes any substance capable of marking, such as, for example, without limitation, ink or dye.
  • grid lines includes without limitation a plurality of spaced lines or other markings, which may be used, for example, to localize a needle entry site for any of numerous different types of procedures, including without limitation any of numerous different types of image-guided procedures, such as computed tomography (“CT”), magnetic resonance imaging (“MRI”) and x-ray procedures, including without limitation image-guided biopsy procedures, and drainage procedures, on any of numerous different body parts, including without limitation thyroid, lung, liver, abdominal, pelvic and extremity biopsies and drainages.
  • CT computed tomography
  • MRI magnetic resonance imaging
  • x-ray procedures including without limitation image-guided biopsy procedures
  • drainage procedures on any of numerous different body parts, including without limitation thyroid, lung, liver, abdominal, pelvic and extremity biopsies and drainages.
  • needle includes without limitation any of numerous different slender, pointed, instruments made of any of numerous different materials, such as steel or plastic, that are used to pierce tissues, which may be used for any of numerous different procedures when piercing tissues, including without limitation injecting a substance into tissue, withdrawing a substance from tissue, suturing and/or otherwise operating on tissue.
  • wt.% refers to a weight percentage of a component, a volume percentage of a component, or molar percentage of a component, respectively, based on the total weight, the total volume of material, or total moles, which includes the component.
  • 10 grams of component in 100 grams of the material is 10 wt.% of component.
  • the PSA compositions of the present invention can “comprise,” “consist essentially of,” or “consist of’ particular ingredients, components, compositions, etc. disclosed throughout the specification.
  • a basic and novel characteristic of the PSA compositions of the present invention is that they can include an acrylic-vinyl acetate copolymer, a tackifier, a plasticizer, and a solvent system (having a boiling point of 175 °C to 250 °C).
  • the PSA compositions of the present invention can be capable of allowing a marking medium to flow through the composition without substantially laterally spreading out within the composition (when the composition is in the form of a layer having a thickness within a particular thickness range).
  • FIGS. 1A - IB is an illustration of a label or tape of the present invention that includes a PSA composition of the present invention without channels (FIG. 1A) and with channels (FIG. IB).
  • FIG. 2 is a front surface of an image guided biopsy grid to which a PSA composition of the present invention can be attached to.
  • FIG. 3 is an illustration of a method of forming a marking on a patient’ s skin in one aspect of the present invention.
  • a marking medium e.g., ink such as from a pen (e.g., a SHARPIE® pen) is desired to go through/bleed through image guided biopsy grid and the adhesive composition to make a marking on a surface (e.g., a subject skin) to which the adhesive is attached.
  • PSA compositions according to the present invention can be capable of allowing a marking medium (e.g., an ink) to flow through the composition without substantially laterally spreading out within the composition (when the composition is in the form of a layer having a desired thickness). That is, the composition was capable of allowing the ink to quickly bleed though the composition and form a narrow focused line, rather than a broad wide line.
  • a marking medium e.g., an ink
  • PSA Pressure Sensitive Adhesive
  • the PSA compositions of the present invention can include an acrylic-vinyl acetate copolymer, a tackifier, a plasticizer, and a solvent system (having a boiling point of 175 °C to 250 °C).
  • the PSA composition can include, based on the total weight of the composition, 55 wt. % to 95 wt. % of the acrylic-vinyl acetate copolymer (or 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, or 95 to 95 wt. % or any number or range therein).
  • the acrylic-vinyl acetate copolymer or 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78
  • the PSA composition can include, based on the total weight of the composition, 3 wt. % to 30 wt. % of the tackifier (or 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 to 30 wt. % or any number or range therein).
  • the PSA composition can include, based on the total weight of the composition, 1 wt. % to 12 wt. % of the plasticizer (or 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 to 12 wt. % or any number or range therein). [0043] In some aspects, the PSA composition can include, based on the total weight of the composition, 0.1 wt. % to 4 wt.
  • % of the solvent system (or 0.1, 0.2, 0.3, 0.4, 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, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, or 4 to 4 wt. % or any number or range therein).
  • the PSA compositions can be uncured.
  • the PSA compositions can be cured and can include a crosslinker (e.g., an aluminum-based crosslinker).
  • the cured PSA composition can include, based on the total weight of the composition, 0.1 wt. % to 2.5 wt. % of a crosslinker (or 0.1, 0.2, 0.3, 0.4, 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, 2.1, 2.2, 2.3, 2.4, or 2.5 to 2.5 wt. % or any number or range therein).
  • an “uncured” PSA composition of the present invention can include, based on the total weight of the composition, 73.5 wt. % of the acrylic-vinyl acetate copolymer, 21 wt. % of the tackifier, 2.1 wt. % of the plasticizer, 1.2 wt. % of the solvent system, and the crosslinker, as described further herein with respect to Example 1.
  • the crosslinker can be added in any amount disclosure throughout this specification.
  • the PSA compositions of the present invention can include an acrylic-vinyl acetate copolymer.
  • the acrylic-vinyl acetate copolymer can include, based on the total weight of the copolymer, 55 wt. % to 98 wt.
  • the aery lie- vinyl acetate copolymer can include, based on the total weight of the copolymer, 2 wt. % to 45 wt.
  • the acrylic-vinyl acetate copolymer can be LOCTITE® Duro-Tak® 788 (available from Henkel Corporation).
  • the PSA compositions of the present invention can include a tackifier.
  • a tackifier can help increase the adhesive strength or stiffness of the PSA composition.
  • Non-limiting examples of tackifiers that can be used in the context of the present invention include rosinbased tackifier resins, terpene -based tackifier resins, phenolic tackifier resins, and/or hydrocarbon-based tackifier resins or any combination thereof.
  • the tackifier can include a hydrogenated rosin and/or rosin ester.
  • the hydrogenated rosin and/or rosin ester can be a glycol or pentaerythritol based resin.
  • the tackifier may correspond to a highly hydrogenated pentaerythritol ester, such as TECKROSTM H95 (available from Teckrez, Inc. of Jacksonville, FL).
  • rosin-based tackifier resins include unmodified rosins (raw rosins) such as gum rosin, wood rosin and tail-oil rosin; modified rosins (hydrogenated rosins, disproportionated rosins, polymerized rosins, other chemically-modified rosins, etc.) obtainable by subjecting these unmodified rosins to modifications such as hydrogenation, disproportionation and polymerization; and various other rosin derivatives.
  • the rosin derivatives include rosin esters such as rosin esters obtainable by esterifying unmodified rosins with alcohols (i.e.
  • esterified rosins and modified rosin esters obtainable by esterifying modified rosins (hydrogenated rosins, disproportionated rosins, polymerized rosins, etc.) with alcohols (i.e. esterified modified rosins); unsaturated fatty acid- modified rosins obtainable by modifying unmodified rosins or modified rosins (hydrogenated rosins, disproportionated rosins, polymerized rosins, etc.) with unsaturated fatty acids; unsaturated fatty acid-modified rosin esters obtainable by modifying rosin esters with unsaturated fatty acids; rosin alcohols obtainable by reduction of carboxy groups in unmodified rosins, modified rosins (hydrogenated rosins, disproportionated rosins, polymerized rosins, etc.), unsaturated fatty acid-modified rosins, or unsaturated fatty acid-modified rosin esters; and
  • Non-limiting examples of terpene-based tackifier resins include terpenes (typically monoterpenes) such as a-pinene, P-pinene, d-limonene, 1-limonene, dipentene, etc.
  • the resin can be a homopolymer of one species of terpene or a copolymer of two or more species of terpene.
  • Examples of the homopolymer of one species of terpene include a-pinene polymer, P- pinene polymer and dipentene polymer.
  • Other examples of the terpene-based tackifier resin include resins obtainable by modifying the terpene resins. Specific examples include styrene- modified terpene resins and hydrogenated terpene resins.
  • phenolic tackifier resins include terpene phenol resins, alkyl phenol resins, or rosin-phenol resins.
  • the terpene phenol resin includes a polymer comprising a terpene residue and a phenol residue, which encompasses both a copolymer of a terpene and a phenol compound (terpene-phenol copolymer resin) and a phenol-modified terpene homopolymer or copolymer (phenol-modified terpene resin).
  • terpenes forming such terpene-phenol resins include the aforementioned monoterpenes.
  • the hydrogenated terpene-phenol resin has a structure obtained by hydrogenating such a terpene-phenol resin.
  • the alkylphenol resin is a resin (oil-phenol resin) obtainable from an alkylphenol and formaldehyde. Examples of the alkylphenol resin include novolacs and resoles.
  • Rosin-phenol resins are typically phenol-modified products of rosins or the aforementioned various rosin derivatives (including rosin esters, unsaturated fatty acid- modified rosins, and unsaturated fatty acid-modified rosin esters).
  • the rosin- phenol resin include rosin-phenol resins obtainable by a method where a phenol is added to a rosin or one of the aforementioned rosin derivatives in the presence of an acid catalyst and thermally polymerized, and like method.
  • a phenol-modified rosin ester rosin ester-phenol resin
  • hydrocarbon-based tackifier resin examples include various hydrocarbon resins such as aliphatic hydrocarbon resins, aromatic hydrocarbon resins, aliphatic cyclic hydrocarbon resins, aliphatic/aromatic petroleum resins (styrene-olefin copolymers and the like), aliphatic/alicyclic petroleum resins, hydrogenated hydrocarbon resin, coumarone resins, and coumarone indene resins.
  • the aliphatic hydrocarbon resins include polymers of one, two or more of aliphatic hydrocarbons selected among olefins and dienes having about 4 to 5 carbon atoms.
  • the olefin examples include 1 -butene, isobutylene and 1 -pentene.
  • diene examples include butadiene, 1,3 -pentadiene and isoprene.
  • aromatic hydrocarbon resins examples include polymers of vinyl-group- containing aromatic hydrocarbons (styrene, vinyl toluene, a-methyl styrene, indene, methyl indene, etc.) having 8 to 10 carbon atoms.
  • alicyclic hydrocarbon resins examples include alicyclic hydrocarbon-based resins obtainable by polymerization of cyclic dimers of so-called “C4 petroleum fractions” and “C5 petroleum fractions”; polymers of cyclic diene compounds (cyclopentadiene, dicyclopentadiene, ethylidene norbomene, dipentene, etc.) or hydrogenation products of these polymers; and alicyclic hydrocarbon-based resins obtainable by hydrogenation of aromatic rings in aromatic hydrocarbon resins or aliphatic-aromatic petroleum resins.
  • the PSA compositions of the present invention can include a plasticizer.
  • plasticizers include phthalates, benzoates, trimethylolpropane esters, trimethylolethane esters, trimethylolmethane esters, glycerol esters, pentaerythritol esters, naphthenic mineral oils, adipates, cyclohexyldicarboxylates, liquid paraffins, natural oils (optionally epoxidized), polypropylenes, polybutylenes, hydrogenated polyisoprenes, and mixtures thereof.
  • phthalates examples include diisononyl phthalate, diisobutyl phthalate, dioctyl phthalate, dicyclohexyl phthalate, diisooctyl phthalate, diisododecyl phthalate, dibenzyl phthalate or butylbenzyl phthalate.
  • benzoates include neopentyl glycol dibenzoate (available, for example, under the name Uniplex® 512 from Lanxess), dipropylene glycol dibenzoate (available, for example, under the name Benzoflex® 9-88SG from Eastman), a mixture of diethylene glycol dibenzoate and of dipropylene glycol dibenzoate (available, for example, under the name K-Flex® 850 S from Kalama Chemical), or a mixture of diethylene glycol dibenzoate, dipropylene glycol dibenzoate and triethylene glycol dibenzoate (available, for example, under the name Benzoflex® 2088 from Eastman).
  • pentaerythritol esters include pentaerythrityl tetravalerate (available, for example, under the name PevalenTM from the company Perstorp).
  • cyclohexanedicarboxylates include diisononyl 1,2-cyclohexanedicarboxylate (available, for example, under the name Hexamoll Dinch® from BASF).
  • the plasticizer can include a benzyl phthalate.
  • the benzyl phthalate can be isononyl benzyl phthalate.
  • the isononyl benzyl phthalate is commercially available from Valtris Specialty Chemicals (Independent, Ohio) under the trade name SANTICIZER® 261 A.
  • the PSA compositions of the present invention can include a solvent system having a boiling point of 175 °C to 250 °C.
  • the solvent system can include a dibasic ester.
  • the dibasic ester can be dimethyl adipate, dimethyl glutarate, or dimethyl succinate, or any combination thereof.
  • the solvent system can include a combination of dimethyl succinate and dimethyl adipate, which is commercially available from Ataman Chemicals (Istanbul, Turkey) under the tradename Santosol DME-8.
  • additional solvents can be used in the context of the present invention, preferably those that have a boiling point of at least 170 °C or at least 175 °C or even more preferably 175 °C to 250 °C or any number or range therein (e.g., 175, 180, 185, 190, 195, 200, 205, 210, 215, 220, 225, 230, 235, 240, 245, 250 °C).
  • additional solvents include 2-amino-2-methyl-l -propanol, and/or water.
  • the additional solvents can include a 95% 2-amino-2-methyl-l -propanol solution (5% water), which is commercially available from Angus Chemical Company (Buffalo Grove, Illinois) under the tradename AMP-95®. 5.
  • AMP-95® 95% 2-amino-2-methyl-l -propanol solution
  • the PSA compositions of the present invention can include a cross-linking agent.
  • cross-linking agents include titanium acetylacetonate, tert n-butyl titanate, methylene-bis-acrylamide, diethylene glycol diacrylate, ethylene glycol diacrylate, triethylene glycol-bis-methacrylate, ethylene glycol-bis-methacrylate, ethylene glycoldimethacrylate, bisacrylamide, triethyleneglycol-bis-acrylate, 3,3'-ethylidene-bis(N-vinyl-2- pyrrolidone), trimethylolpropate trimethacrylate, glycerol trimethacrylate, polyethylene glycol dimethacrylate, and/or other poly acrylate and polymethacrylate esters.
  • aluminum-based cross-linking agents can be used.
  • aluminum-based cross linking agents include aluminum citrate, aluminum tartrate, and/or aluminum acetylacet
  • the PSA compositions of the present invention can include an additive or multiple additives.
  • the PSA compositions of the present invention can include an amount of additives, based on the total weight of the composition, of 0 and 1 wt. %, preferably 0.01 wt.% and less than 1 wt. % or between 0.5 wt. % and less than 1 wt.
  • % or 0 wt.%, 0.1 wt.%, 0.2 wt.%, 0.3 wt.%, 0.4 wt.%, 0.5 wt.%, 0.6 wt.%, 0.7 wt.%, 0.8 wt.%, 0.9 wt.%, or 1 wt.% or any range or value therebetween.
  • Non-limiting examples of additives include, but are not limited to, fillers, additionally solvents, moisture absorbers, antioxidants, pigments, colorants, adhesion promoters, UV stabilizers, flame-retardant additives, rheological additives, waxes, or combinations thereof.
  • Non-limiting examples of fillers include organic fillers, inorganic fillers and mixtures thereof.
  • organic filler one can use any (s) load (s) organic (s) and in particular polymeric (s) typically used (s) in the field of adhesives.
  • polyvinyl chloride PVC
  • polyolefin s
  • rubber ethylene vinyl acetate
  • EVA aramid fibers
  • KEVLAR® expandable or non-expandable thermoplastic polymer hollow microspheres
  • thermoplastic polymer chosen from those used in the preparation of HMPSA, such as ethylene vinyl acetate (EVA), or styrenic block copolymers (such as SIS, SBS, SIBS, SEBS, SEPS, and their derivatives grafted with for example maleic anhydride).
  • Non-limiting examples of additional solvents include hydrophilic solvents (e.g., water) or hydrophobic solvents (e.g., organic liquids such as dimethyl sulfoxide).
  • Non-limiting examples of moisture absorbers (or desiccant) include non-polymeric hydrolyzable alkoxysilane derivatives, with a molecular mass of less than 500 g/mol, preferably chosen from trimethoxy silane and triethoxy silane derivatives. Such an agent can typically extend the storage life of the composition during storage and transportation before it is used.
  • Silquest® A- 174 for example available, under the trade name Silquest® A- 174, from Momentive
  • methacryloxymethyltrimethoxysilane for example available, under the name Geniosil® XL33, from Wacker
  • vinyltrimethoxysilane isooctyltrimethoxysilane or phenyltrimethoxy silane .
  • Antioxidants can include compounds that may be introduced to protect the composition from degradation resulting from a reaction with oxygen which is liable to be formed by the action of heat or light. These compounds may include primary antioxidants which trap free radicals. The primary antioxidants may be used alone or in combination with other secondary antioxidants or UV stabilizers. Non-limiting examples of antioxidants include Irganox® 1010, Irganox® B561, Irganox® 245, Irganox® 1076 and Irgafos® 168 sold by BASF.
  • Non-limiting examples of pigments include organic or inorganic pigments (e.g., titanium dioxide), such as Kronos® 2059 sold by Kronos.
  • Non-limiting examples of rheological additives include thixotropic agents, PVC plastisols (corresponding to a suspension of PVC in a plasticizer miscible with PVC, obtained in situ by heating at temperatures ranging from 60 ° C to 80 ° C.
  • PVC plastisols corresponding to a suspension of PVC in a plasticizer miscible with PVC, obtained in situ by heating at temperatures ranging from 60 ° C to 80 ° C.
  • These plastisols can be those described in particular in the book "Polyurethane Sealants", Robert M. Evans, ISBN 087762- 998-6), fumed silica, and/or urea derivatives resulting from the reaction of an aromatic diisocyanate monomer such as 4,4'-MDI with an aliphatic amine such as butylamine (the preparation of such urea derivatives is described in particular in application FR 1 591 172).
  • Non-limiting examples of micronized amide waxes include CRAYVALLAC ® SL, CRAYVALLAC ® SLX, CRAYVALLAC ® SLT marketed by ARKEMA.
  • a tackifier can be added to an aery lie- vinyl acetate copolymer and mixed until the tackifier is completely dissolved.
  • a plasticizer, a solvent system, and a crosslinker can be then be added and blended, resulting in an “uncured” PSA composition.
  • the “uncured” PSA composition may then be cured and dried in an oven to form a “cured” PSA composition.
  • the tackifier and high boiling point solvent(s) do not evaporate during the curing/drying process but instead remain in the “cured” PSA composition.
  • retention of one or more high boiling point solvents e.g., a mixture of dimethyl succinate and dimethyl adipate, in some embodiments
  • the tackifier e.g., TECKROSTM H95 [Teckrez], in some embodiments
  • retention of one or more high boiling point solvents e.g., a mixture of dimethyl succinate and dimethyl adipate, in some embodiments
  • the tackifier e.g., TECKROSTM H95 [Teckrez], in some embodiments
  • TECKROSTM H95 [Teckrez] TECKROSTM H95 [Teckrez]
  • compositions of the present disclosure have properties described above. Such compositions are appropriate for a wide-variety of applications. Accordingly, the compositions of the present disclosure can be comprised in an article of manufacture and aspects of the disclosure also relate to articles including the PSA compositions described herein.
  • articles of manufacture may be utilized in one or more of the following industries or applications: an image guided biopsy grid application; a label application; or a tape application (among numerous other possible applications).
  • the compositions as described herein can be adapted to be used in various applications.
  • the compositions as described herein can be used to make various articles or components of the articles.
  • the article can be an image guided biopsy grid which may be utilized in the medical field.
  • the article can be a label or tape, which may be utilized in numerous possible fields.
  • article 10 can include a film or substrate layer 11, an adhesive layer comprising a PSA composition of the present invention 12, and an optional release liner 13. In some instances, release liner 13 is not included (not shown) or can be removed, and then the article 10 can be adhered to a surface (not shown).
  • the substrate 11 can be any type of material to which the adhesive 12 can be applied.
  • the substrate 11 is a polyolefin based substrate (e.g., polyethylene or polypropylene).
  • the substrate 11 is a thermoplastic substrate or a thermoset substrate.
  • the substrate 11 is a paper or a woven or a non-woven material.
  • the substrate 11 can include a first surface and a second surface opposite the first surface, and the adhesive layer 12 can include a third surface and a fourth surface opposite the third surface (where the second surface is in contact with the third surface).
  • the article 10 can include a release liner 13 in contact with the fourth surface.
  • the substrate 11 of the article 10 can include openings or channels (14) that extend through the first and second surfaces of the substrate 11, but the adhesive layer 12 does not include such openings.
  • the channels can allow a marking medium (e.g., ink) to flow through the substrate 11 and reach the adhesive 12.
  • the adhesive 12 can then allow the marking medium to flow through it and ultimate mark a surface to which the adhesive 12 is attached (e.g., skin of a subject such as an animal or a person).
  • the first side of the substrate 11 can include a marking (e.g., including a plurality of lines spaced relative to each other to form a grid pattern). Referring to FIG. 2, and in one-non-limiting aspect, a grid pattern is shown that can be included on a surface of the substrate 11 that is opposite the adhesive layer 12. In a particular aspect, at least a portion of the plurality of lines can have a line width of less than about 1/8 inch.
  • the substrate 11 of such an article 10 can be a non-woven layer (e.g., to allow a marking applied to the article to pass substantially directly through the article).
  • a non-woven layer can have a particular basis weight (e.g., about 2/5 oz/yd 2 to about 1 oz/yd 2 ), a particular thickness (e.g., less than about 25 mils), or a combination thereof.
  • an article 11 can have a particular substrate 12 thickness (e.g., 2 mils to 10 mils), a particular adhesive layer 12 thickness (e.g., 0.1 mils to 5.0 mils), a particular article 10 thickness (e.g., 2 mils to 14 mils), or any combination thereof.
  • a marking medium e.g., an ink or dye
  • the method can include marking (e.g., by applying an ink pen) a first portion of an article, where at least a second portion of the article is in contact with the person’s skin, and the marking medium (e.g., ink from the ink pen) passes through the first and second portions of the article and marks the person’s skin.
  • the first portion of the article e.g., the substrate
  • the marking on the skin can be substantially the same size and shape as the marking on the first portion of the article.
  • the method can include imaging a portion of the person’s body and article attached to the body, identifying a needle entry target in the first portion of the article with reference to one or more grid lines on a portion of the article, and marking the needle entry target with the marking medium so that the marking medium passes through the article and marks the needle entry target on the skin.
  • the method can include removing the article from the skin and inserting a biopsy needle substantially at the marked needle entry target on the skin.
  • FIG. 3 provides an overview of one aspect of the present invention for marking a person’s skin with a marking medium.
  • an “uncured” PSA composition was formed that included, based on the total weight of the composition, 73.5 wt. % of an acrylic-vinyl acetate copolymer [LOCTITE® Duro-Tak® 788, Henkel], 21 wt. % of a tackifier [TECKROSTM H95, Teckrez], 2.1 wt. % of a plasticizer [SANTICIZER® 261 A, Valtris], 1.2 wt. % of a solvent system [Santosol DME-8, Ataman], and a crosslinker [aluminum acetylacetonate] .
  • an acrylic-vinyl acetate copolymer [LOCTITE® Duro-Tak® 788, Henkel]
  • 21 wt. % of a tackifier [TECKROSTM H95, Teckrez]
  • SANTICIZER® 261 A, Valtris 1.2 wt. % of a solvent
  • the tackifier was added to the acrylic-vinyl acetate copolymer and mixed until the tackifier completely dissolved.
  • the plasticizer, solvent system, and crosslinker were then added and blended, resulting in the “uncured” PSA composition.
  • Example 1 The “uncured” PSA composition of Example 1 was then cured and dried in an oven to form an example of a “cured” PSA composition. It was discovered that the tackifier and the solvent system do not evaporate during the curing/drying process but instead remain in the “cured” PSA composition.
  • the example of the “cured” PSA composition included the acrylic-vinyl acetate copolymer, the tackifier, the plasticizer, the solvent system, and 1.3 wt. % of the crosslinker. The amount of each component can be modified in a manner described throughout this specification.
  • retention of the solvent system and/or the tackifier in the cured adhesive composition may provide the capability for a marking medium (e.g., an ink) to flow through the composition (e.g., when applied as an adhesive to a substrate, such as a non-woven substrate that may be utilized for an image guided biopsy grid application, as one non-limiting example).
  • a marking medium e.g., an ink
  • a substrate such as a non-woven substrate that may be utilized for an image guided biopsy grid application, as one non-limiting example.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Theoretical Computer Science (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne des compositions d'adhésifs sensible à la pression (PSA) qui comprennent au moins un copolymère acrylique-acétate de vinyle, un agent poisseux, un plastifiant et un système de solvant (ayant un point d'ébullition de 175 °C à 250 °C). Selon certains aspects, de telles compositions peuvent être capables de permettre à un milieu de marquage (par exemple, une encre ou un colorant) de s'écouler à travers la composition sans s'étaler sensiblement latéralement à l'intérieur de la composition.
PCT/US2024/053179 2023-10-31 2024-10-28 Compositions d'adhésifs sensibles à la pression et diverses applications associées Pending WO2025096322A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5360845A (en) * 1992-12-23 1994-11-01 National Starch And Chemical Investment Holding Corporation Starch ester based hot melt adhesive
US20030068491A1 (en) * 1999-10-08 2003-04-10 Dai Nippon Printing Co., Ltd. Pressure-sensitive adhesive for pressure-sensitive adhesive layer in volume hologram laminate
US20090308278A1 (en) * 2003-07-03 2009-12-17 Mcdaniel C Steven Antifungal Paints and Coatings
US20110079651A1 (en) * 2002-12-02 2011-04-07 Kuolih Tsai Method for labeling fabrics and heat-transfer label well-suited for use in said method
US20150252195A1 (en) * 2012-10-29 2015-09-10 Alexander J. Kugel Pavement marking compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5360845A (en) * 1992-12-23 1994-11-01 National Starch And Chemical Investment Holding Corporation Starch ester based hot melt adhesive
US20030068491A1 (en) * 1999-10-08 2003-04-10 Dai Nippon Printing Co., Ltd. Pressure-sensitive adhesive for pressure-sensitive adhesive layer in volume hologram laminate
US20110079651A1 (en) * 2002-12-02 2011-04-07 Kuolih Tsai Method for labeling fabrics and heat-transfer label well-suited for use in said method
US20090308278A1 (en) * 2003-07-03 2009-12-17 Mcdaniel C Steven Antifungal Paints and Coatings
US20150252195A1 (en) * 2012-10-29 2015-09-10 Alexander J. Kugel Pavement marking compositions

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