WO2013082222A1 - Adhésif autocollant - Google Patents

Adhésif autocollant Download PDF

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Publication number
WO2013082222A1
WO2013082222A1 PCT/US2012/066956 US2012066956W WO2013082222A1 WO 2013082222 A1 WO2013082222 A1 WO 2013082222A1 US 2012066956 W US2012066956 W US 2012066956W WO 2013082222 A1 WO2013082222 A1 WO 2013082222A1
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WO
WIPO (PCT)
Prior art keywords
acrylic acid
pressure sensitive
sensitive adhesive
monomers
acid ester
Prior art date
Application number
PCT/US2012/066956
Other languages
English (en)
Inventor
Weinan Wang
Jessie MA
Junfeng Cao
Jestine HUANG
Original Assignee
3M Innovative Properties Company
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Publication date
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Publication of WO2013082222A1 publication Critical patent/WO2013082222A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/58—Adhesives
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • 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
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • 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
    • C09J2301/312—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 parameters being the characterizing feature
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer
    • 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
    • C09J2475/00—Presence of polyurethane
    • C09J2475/006—Presence of polyurethane in the substrate

Definitions

  • the invention relates to a pressure sensitive adhesive and the application thereof, and specifically, to an acrylate pressure sensitive adhesive and the application of the acrylate pressure sensitive adhesive for a pressure sensitive adhesive tape and a medical dressing tape.
  • the wound dressing tape is a product for bandaging a wound or a material for covering a sore, a scar or other lesion.
  • the wound dressing tape has a typical structure comprising a layer of pressure sensitive adhesive applied on a backing and a release film attached on the adhesive side of the pressure sensitive adhesive tape, such as shown in Figure 1.
  • Some wound dressing tapes are waterproof and impermeable to a moisture vapor, and some wound dressing tapes are both waterproof and permeable to a moisture vapor.
  • the wound dressing tapes which are both waterproof and permeable to a moisture vapor are attracting more and more attention.
  • WO 84/03837 discloses a solvent-based acrylate pressure sensitive adhesive having a good adhesion to both of dry and moist skins.
  • This pressure sensitive adhesive contains a number of hydrophilic monomers as the components and thus has a good adhesive power under the high humidity environment.
  • this patent document does not relate to the moisture vapor transmission rate of the acrylate pressure sensitive adhesive.
  • US 6,680,1 13 discloses a pressure sensitive adhesive for a dressing tape, which has higher moisture vapor transmission rate and better adhesion value.
  • This pressure sensitive adhesive has a multilayer structure comprising one or more films having high moisture vapor transmission and a pressure sensitive adhesive layer having high adhesion, and exhibits an overall moisture vapor transmission rate of 1200g/m 2 /24hrs/37°C and an adhesion value of 15g/inch.
  • the high moisture vapor transmission of the pressure sensitive adhesive for a dressing tape is accomplished mainly by the one or more films having high moisture vapor transmission. However, the effect of the pressure sensitive adhesive used on the moisture vapor transmission is not discussed.
  • the present disclosure relates to an acrylate pressure sensitive adhesive which has high moisture vapor transmission, high hydrophilicity and good adhesion.
  • an acrylate pressure sensitive adhesive comprising a polymer formed by a free radical polymerization of the following monomers:
  • an acrylate pressure sensitive adhesive which has not only good moisture vapor transmission rate but also good adhesion to both of dry and moist skins and exhibits properties such as low irritation and no adhesive residue can be obtained.
  • the disclosure further relates to a pressure sensitive adhesive tape having a high Moisture Vapor Transmission Rate (MVTR) property, comprising a layer of the disclosed acrylate pressure sensitive adhesive applied on a backing, wherein the pressure sensitive adhesive tape can have a MVTR (upright) of 1900g/m 2 /24hrs/37°C, measured after applying a 25 ⁇ thick dry adhesive film on a 25 ⁇ thick polyurethane film.
  • MVTR Moisture Vapor Transmission Rate
  • the disclosure further relates to a method of preparing the pressure sensitive adhesive tape, comprising: applying a layer of the disclosed acrylate pressure sensitive adhesive on a backing, and curing the acrylate pressure sensitive adhesive by a cross-linking reaction.
  • the disclosure further relates to a medical dressing tape comprising the disclosed pressure sensitive adhesive tape and a release film attached on the adhesive side of the pressure sensitive adhesive tape.
  • the medical dressing tape exhibits an initial dry skin adhesion value of -lOOg/inch and an initial moist skin adhesion value of ⁇ 45g/inch, and exhibits a dry/moist skin adhesion value after 72 hours of ⁇ 170g/inch, and a dry/moist skin adhesion value after 168 hours of ⁇ 1 10g/inch (as used in the invention, " ⁇ " represents an average; since different peoples have much different skins, the adhesion to the skin is represented by an average).
  • the disclosed acrylate pressure sensitive adhesive and medical dressing tape has high moisture vapor transmission, good adhesion and superior hydrophilicity as well as low cost, and further exhibits advantages of high adhesion, little adhesive residue and low irritation to the skin and the like, and can maintain very high adhesive power even under a high humidity environment.
  • Fig. 1 is a cross section view of the structure of an exemplified wound dressing tape.
  • Fig. 2 shows the relationships between intrinsic viscosity (I.V.) / moisture vapor transmission rate (MVTR) and the ratio of 2-(2-ethoxyethoxy) ethyl acrylate (EEEA) monomer.
  • Fig. 3 shows the internal clinical test results of the adhesion of the pressure sensitive adhesive of the invention.
  • Fig. 4 is a schematic view of the measuring method of the moisture vapor transmission rate (MVTR). While the above-identified drawings and figures set forth embodiments of the invention, other embodiments are also contemplated, as noted in the discussion. In all cases, this disclosure presents the invention by way of representation and not limitation. It should be understood that numerous other modifications and embodiments can be devised by those skilled in the art, which fall within the scope and spirit of this invention. The figures may not be drawn to scale.
  • the disclosed acrylate pressure sensitive adhesive comprises a polymer formed by copolymerization of the following four monomers:
  • the copolymerization method may be a conventional free radical polymerization method.
  • the specific conditions of the polymerization are as follows:
  • the temperature is controlled at 60 °C
  • the stirring rate is controlled at 70 revolutions/min.
  • the reaction time is controlled at 24 hrs so that the conversion rate is 99 % or more.
  • the materials are finally cooled to 43 °C and discharged.
  • the final resulting polymer has an I.V. between 0.9 and l . ldl/g and a weight average molecular weight Mw between 500,000 and 900,000.
  • the method for measuring the conversion rate is as follows:
  • EtOAc herein comprises EtOAc for dissolving AIBN.
  • the hydrophilic acrylic acid ester monomer which has a hydroxyl group or an ethoxy group of the invention includes, but is not limited to, trimethylolpropane diacrylate, pentaerythritol triacrylate, trimethylolpropane triacrylate, 2-hydroxyethyl acrylate (2-HEA), 4-hydroxybenzyl acrylate (4-HBA), 2- (2-ethoxyethoxy)ethyl acrylate (EEEA). EEEA, 2-HEA and 4-HBA are most preferable.
  • EEEA As an example, as can be seen from Fig.2, when the ratio of EEEA is increased from 5 % to 10 % of the total content of monomers, MVTR is increased by 56 g/m 2 /24hrs. However, when the ratio of EEEA is increased from 15 % to 22 %, MVTR is only increased by 5 g/m 2 /24hrs. On the other hand, when the concentration of EEEA is increased, the intrinsic viscosity (I.V.) is also greatly increased. However, too high intrinsic viscosity is found to decrease the adhesion to the surface of the skin, including initial adhesion and persistent adhesion.
  • I.V. intrinsic viscosity
  • the ratio of the hydrophilic acrylic acid ester monomer which has a hydroxyl group or an ethoxy group is preferably 10% to 30%, and more preferably 15 % to 25 % of the total weight of all monomers.
  • Fig.4 shows an apparatus for measuring MVTR and a method for mounting the sample to be measured.
  • the MVTR measurement is performed at a temperature of 37°C, according to TMS0759.
  • the PU film used is a PU film supplied by Bayer. The specific steps and conditions are as follows:
  • T test time (hrs), which is greater than 18 hrs. b) Short-chain hydrophobic acrylic acid ester monomer and c) long-chain hydrophobic acrylic acid ester monomer
  • the present inventors has further studied the effects of a hydrophobic acrylic acid ester monomer on the moisture vapor transmission and adhesion of the pressure sensitive adhesive, and found that a good balance between the MVTR and adhesion can be achieved by classifying the hydrophobic acrylic acid ester monomer into a short-chain hydrophobic acrylic acid ester monomer and a long-chain hydrophobic acrylic acid ester monomer and properly controlling the ratio between the two monomers.
  • the specific examples thereof includes, but is not limited to, methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate and the like, preferably methyl acrylate, ethyl acrylate, butyl acrylate, and most preferably butyl acrylate (BA).
  • R 2 is an alkyl group having 6 to 14 carbon atoms.
  • the specific examples thereof includes, but is not limited to, 2-ethyl-hexyl acrylate, isooctyl acrylate, octyl acrylate, decyl acrylate, dodecyl acrylate, tridecyl acrylate and the like, and preferably 2-ethyl-hexyl acrylate (2-EHA) and isooctyl acrylate.
  • the ratio between b) short-chain hydrophobic acrylic acid ester monomer and c) long-chain hydrophobic acrylic acid ester monomer of the invention has a significant influence on the MVTR and adhesion of the pressure sensitive adhesive.
  • Table IV if the content of EEEA is kept unchanged, the ratio of BA is increased and the ratio of 2-EHA is decreased, the MVTR is greatly improved.
  • the weight percent of BA in all monomers is increased from 0 to 75 parts, the MVTR is improved from ⁇ 1500g/m 2 /24hrs to ⁇ 2200g/m 2 /24hrs, while the adhesion is significantly decreased.
  • the ratios of monomers must be kept within suitable ranges in order to achieve a good balance between the MVTR and adhesion.
  • the ratio of the short-chain hydrophobic acrylic acid ester monomer is preferably 50% to 70% and most preferably 55% to 65% by weight of the total monomers and the ratio of the long-chain hydrophobic acrylic acid ester monomer is preferably 10% to 35% and most preferably 20% to 30% by weight of the total monomers.
  • the substrate for adhesion test stainless steel plate
  • I.V. intrinsic viscosity, measured according to TM0148
  • PU film polyurethane film supplied by Vix Co., Korea, a 20.3 ⁇ PU blank film with a MVTR of 3000g/m 2 /24hrs
  • the acryl monomer having a polar group copolymerizable with the above monomers (a) to (c) of the invention is preferably an acryl monomer having a high glass transition temperature, and more preferably an acryl monomer having a carboxyl group or amide group.
  • the specific examples thereof include, but are not limited to, acrylamide, acrylic acid, methacrylamide, and methacrylic acid; preferably acrylamide and acrylic acid due to their stronger polarity; and more preferably acrylamide because it has no irritation.
  • the weight ratio of the acryl monomer having a polar group copolymerizable with the above monomers (a) to (c) in all monomers is preferably 0.5% to 5% and more preferably 1% to 3%.
  • the monomers are mainly consisting of four types of monomers.
  • the first type is a hydrophilic monomer having a hydroxyl group or an ethoxy group at a ratio of 10 to 30% of all monomers, which can mainly provide a certain moisture vapor transmission and further improve the adhesive power to the moist skin.
  • this type of monomers are generally considered to be hydrophobic, they have better moisture vapor transmission as compared with the long-chain acrylic acid ester monomer (see Table IV), and can adjust the balance between the adhesion and the moisture vapor transmission and provide a certain cohesion strength.
  • These long-chain monomers have good flexibility and can enhance the wettability of the adhesive and improve the initial adhesion and peeling power so as to improve the adhesion of the adhesive as a whole.
  • the fourth type is a polar monomer such as acrylamide, acrylic acid, methacrylamide, methacrylic acid and the like, which generally has a polar group such as a carboxyl group or an amide group and can impart good cohesion strength to the adhesive, is easy to be crosslinked and can form firm hydrogen bonds with the bonded substrate.
  • This type of monomer comprises 0.5 to 5% of the total weight of all monomers.
  • the acrylate adhesive which is formed by combining one or more monomers selected from each of the above four type monomers and performing the free radical copolymerization reaction, can have not only good moisture vapor transmission rate but also good adhesion to both of dry and moist skins and further exhibit properties such as little irritation and no adhesive residue.
  • the formulations as shown in Table V are several combinations which are preferable in the invention.
  • I.V. intrinsic viscosity, measured according to TM0148
  • PU film polyurethane film, supplied by Vix Co., Korea, a 20.3 ⁇ PU blank film with a MVTR of 3000g/m 2 /24hrs
  • Tegaderm std is Tegaderm Film, product 1626, available from 3M Company
  • Tegaderm HP is Tegaderm HP Transparent Dressing, product 9546, available from 3M Company MMD is Tegaderm Diamond Film, product 1686, available from 3M Company.
  • IV-3000 is a product of Smith & Nephew.
  • the MVTR of 1837 g/m 2 /24hrs for HPA-14/14-L and the MVTR of 1900 g/m 2 /24hrs for HPA-12/12-L are greatly higher than 900g/m 2 /24hrs for Tegadem std and 1 100 g/m 2 /24hrs for Tegaderm HP, and slightly higher than 1700 g/m 2 /24hrs for MMD, but lower than 2700 g/m 2 /24hrs for IV-3000. Lower than IV-3000 mainly due to the different thicknesses of substrate and adhesive.
  • the thickness of the adhesive layer of IV-3000 is only 12 ⁇ , which is a half of those of HPA- 14/14-L and HPA-12/12-L, and the moisture vapor transmission of the substrate is also higher than that of the substrate supplied by the supplier Vix Co.
  • MMD is prepared by using a dot coating process, where the dry adhesive has a dot distribution on the PU film, so there are very great gaps permeable to the moisture vapor between the dots, which allows the MVTR of the adhesive tape to be greatly improved as compared with conventional continuous coating in the case of using the same pressure sensitive adhesive.
  • HPA-14/14-L or HPA-12/12-L which uses a pressure sensitive adhesive having high moisture vapor transmission and is prepared by a conventional continuous coating process.
  • HPA-14/14-L and HPA- 12/12-L have a significant advantage in terms of the MVTR over Tegaderm std and Tegaderm HP with similar thicknesses of the substrate and adhesive layer and coating process.
  • Pressure sensitive adhesive tape and medical dressing tape :
  • the disclosed acrylate pressure sensitive adhesive can be widely applied for various adhesive fields requiring high moisture vapor transmission rate, including industrial, medical and household adhesives.
  • the disclosed acrylate pressure sensitive adhesive can be applied on a backing to form a pressure sensitive adhesive tape.
  • the backing may be a known and conventional backing, such as woven fabric, nonwoven fabric, paper or synthetic material. In order to provide a pressure sensitive adhesive tape having high moisture vapor transmission, the backing would have high moisture vapor transmission in addition to the provision of supporting function.
  • Such backing can be made of a material with high moisture vapor transmission, such as a polyurethane film.
  • the acrylate pressure sensitive adhesive is crosslinked and cured.
  • the crosslinking may be carried out by the irradiation with a ray or by the addition of a cross-linking agent.
  • the ray may be ⁇ -ray or electron beam.
  • the cross-linking agent may be one or more selected from the group consisting of a metal ion cross-linking agent, an aziridine crosslinking agent, and an isocyanate cross-linking agent, and the amount of the cross-linking agent is 0.01 to 5% of the total weight of all monomers.
  • the disclosed acrylate pressure sensitive adhesive is particularly suitable for a medical dressing tape. When the pressure sensitive adhesive tape is used for a medical dressing tape, a release film may be attached on an adhesive side of the pressure sensitive adhesive tape so as to exhibit a very low and stable release force to the pressure sensitive adhesive.
  • the release film includes, but is not limited to, a release film made of a substrate having a coating layer.
  • the substrate includes, but is not limited to, paper-based substrate, film-based substrate, aluminum foil-based substrate and polyolefin-based substrate.
  • the above-mentioned release films each have a coating layer with a low surface energy on at least one surface thereof, and the coating layer comprises one or more of the following compounds: organosilicons, fluorides, fluorosilicon copolymers and compounds with a polyolefin long side chain.
  • the release film is preferably a paper-based release film with a basic weight of 80 to 120g/m 2 available from Baoyan, loparex, etc.
  • the medical dressing tape has a typical structure comprising a polyurethane film 1 , a pressure sensitive adhesive 2 and a release film 3 in this order from up to down.
  • the polyurethane film 1 is supplied from supplier, Vix Co., Korea and has a thickness of 20.3 ⁇ .
  • the pressure sensitive adhesive 2 is the acrylate pressure sensitive adhesive of the invention having an adhesive layer thickness of 25 ⁇ and coated by transfer coating method.
  • the release paper 3 is 80 g onesided release paper supplied from Baoyan, Shanghai. The crosslinking/curing and sterilization are carried out by ⁇ -ray irradiation using a cobalt source from Jin Pengyuan radiation technology limited company, Shanghai, at a dose range of 25-50 kGy.
  • the internal clinical test is performed so as to further verify the properties of preferable examples of the invention in the application, that is, to evaluate the application of the samples of the examples on a healthy person and observe the MVTR, adhesion, adhesive residue, edge curling and skin response of the dressing tapes.
  • Commercially available samples Tegaderm std, Tegaderm HP, IV-3000 and MMD are used as references.
  • the process of preparing the samples is as follows:
  • the four formulations, HPA- 12, HPA- 12L, HPA- 14 and HPA- 14L, of the invention are selected and coated by the coating method: the adhesive is firstly applied on a release paper and a PU film is then applied on the adhesive side.
  • the PU film has a film thickness of 20.3 ⁇
  • the coating amount of the adhesive is 20g/m 2
  • the dry adhesive film has a thickness of 25 ⁇ .
  • the above samples are generally sterilized and crosslinked by ⁇ -ray, then cut into 2.5x8 cm specimens, and attached on backsides of volunteers for clinical test. 12 volunteers are selected and the attached samples are randomly distributed.
  • the adhesion, adhesive residue, edge curling and skin response of the samples at the time of initial 0 h (TO), 72 h (T72) or 168 h (T168) are evaluated.
  • the measuring method is as follows:
  • a clinical research engineer firstly cleans the skin of backside of the subject with a diluted aqueous soap solution.
  • the clinical research engineer attaches 8 dressing tapes (dry) (one per sample) at left side of the backside of the subject. Small amounts of warm water is sprayed at right side of the backside of the subject and further 8 dressing tapes (wet) (one per sample) are attached. After 5 min., these samples are measured according to ASTMD3330 method and the results are recorded as TO. The samples have a size of 2.5x8 cm 2 .
  • the clinical research engineer attaches the same dressing tapes in the same positions of the backside of the subject.
  • the subject is required by the clinical research engineer to return back to IHP testing room after 72 hrs so as to evaluate the floating rate and skin response of all samples. A half of samples are torn off so as to evaluate the adhesion and a ratio of adhesive residue (T72).
  • the subject is required by the clinical research engineer to return back to IHP testing room after 168 hrs so as to evaluate the samples.
  • the remaining half of samples are torn off so as to evaluate the floating ratio, adhesion, ratio of adhesive residue and skin response (T168).
  • Fig. 3 shows the internal clinical test results of the adhesion of the pressure sensitive adhesive.
  • the method for measuring the adhesion is similar to ASTMD3330, except for the change of the steel plate to the backside of a human body, 180° peeling-off and 12 inch/min.
  • TO (Dry) represents an initial adhesion of the measured sample to the dry skin
  • TO (wet) represents an initial adhesion of the measured sample to the moist skin
  • T72 represents an adhesion of the measured sample to the dry or moist skin after 72 hrs
  • T168 represents an adhesion of the measured sample to the dry or moist skin after 168 hrs.
  • the adhesion values of the above measured samples to the skin are all greater than 40 g/inch.
  • HPA- 12/12L or HPA- 14/14L have an initial adhesion value of 90 to 1 10 g/inch and preferably -l OOg/inch to the dry skin, an initial adhesion value of 30 to 50 g/inch and preferably ⁇ 45g/inch to the moist skin, an adhesion value of 160 to 190 g/inch and preferably -170 g/inch after 72 hrs to the dry or moist skin and an adhesion value of 100 to 120 g/inch and preferably ⁇ 1 l Og/inch after 168 hrs to the dry or moist skin.
  • HPA- 12L and HPA- 14L have similar adhesion as compared with those of commercially available samples Tegaderm std, Tegaderm HP and IV-3000, and the adhesion values thereof are higher than that of the reference sample MMD, showing that the above two formulations have good persistent adhesion.
  • HPA- 12 and HPA- 14 have an adhesion similar to that of MMD, but their adhesion values at T72 and T168 are lower than those of commercially available samples Tegaderm std, Tegaderm HP and IV-3000.
  • the adhesive residue and edge curling are also important factors affecting the properties of the dressing tape in the application.
  • the rating of 0-5 is used to evaluate the adhesive residue and edge curling of the dressing tape, wherein 0 represents no adhesive residue or edge curling, 2- 4 represent incremental adhesive residue or edge curling, and 5 represents whole adhesive residue or sample peeling-off.
  • the adhesive residue and edge curling of the evaluated samples at T72 are shown in Table VI.
  • the formulations HPA- 12L, HPA- 14L, HPA- 12 and HPA- 14 of the invention are observed to have no adhesive residue in the internal clinical test and thus have significant advantage as compared with the commercially available products, Tegaderm HP and IV-3000.
  • the evaluated samples do not peel off within 72 h for the evaluation.
  • HPA- 12L and HPA- 14L are observed to have no or slight edge curling, which are same as the commercially available products, Tegaderm HP, Tegaderm Std and rV-3000.
  • HPA- 12 and HPA- 14 have an edge curling which is severer than the above samples, but still better than MMD.
  • the results for evaluating adhesive residue and edge curling of the evaluated samples at T 168 are shown in Table VII.
  • the formulations HPA- 12L, HPA- 14L, HPA- 12 and HPA- 14 of the invention are observed to have no adhesive residue in the long-term internal clinical test of 168 h (that is, 7 days) and thus have significant advantage as compared with the commercially available products, Tegaderm HP and IV-3000.
  • HPA- 12L and HPA- 14L have an edge curling property similar to that of the commercially available products, Tegaderm HP and IV-3000 in the long-term test of 7 days (T168), wherein one or two samples peel off.
  • HPA- 12 and HPA- 14 have an edge curling or peeling-off severer than the above samples, wherein 3-4 samples are peeled off.
  • HPA- 12L and HPA-14L have better adhesion, fewer adhesion residues and better edge curling as compared with HPA-12 and HPA- 14. Furthermore, HPA-12L and HPA-14L have higher MVTR than HPA-12 and HPA-14. Therefore, they are desirably used as the new generation of dressing tape and adhesive tape products having higher moisture vapor transmission and fewer adhesive residues.
  • the invention discloses a pressure sensitive adhesive having high moisture transmission (MVTR ⁇ 1900g/m 2 /24hrs), high adhesion (no peel-off for 7 days, no edge curling and a peeling power of 1 OOg/inch) and low irritation at the same time.
  • It mainly consists of the four types of monomers, that is, the hydrophilic acrylic acid ester monomer which has a hydroxyl group or an ethoxy group, the soft short-chain and long-chain hydrophobic acrylic acid ester monomers, and the hard acryl monomer having a polar group.
  • the pressure sensitive adhesive of the present invention exhibits a great advantage in terms of the properties in the human body test, so it is the first choice of the next generation of medical dressing tapes, and has also wide application prospect in the other industrial adhesive fields such as electronic industry requiring high moisture vapor transmission rate.

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  • Health & Medical Sciences (AREA)
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  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Hematology (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Materials For Medical Uses (AREA)
  • Adhesive Tapes (AREA)

Abstract

La présente invention concerne un adhésif autocollant d'acrylate qui est formé par une polymérisation par radicaux libres des monomères suivants : (a) un monomère d'ester d'acide acrylique hydrophile qui a un groupe hydroxyle ou un groupe éthoxy, la quantité du monomère d'ester d'acide acrylique hydrophile étant de 10 à 30 % du poids total de tous les monomères ; (b) un monomère d'ester d'acide acrylique hydrophobe à chaîne courte représenté par la formule CH2=CHCOOR1, où R1 est un groupe alkyle ayant de 1 à 5 atomes de carbone, la quantité du monomère d'ester d'acide acrylique hydrophobe à chaîne courte étant de 50 à 70 % du poids total de l'ensemble des monomères ; (c) un monomère d'ester d'acide acrylique hydrophobe à chaîne longue représenté par la formule CH2=CHCOOR2, où R2 est un groupe alkyle ayant de 6 à 14 atomes de carbone, la quantité du monomère d'ester d'acide acrylique hydrophobe à chaîne longue étant de 10 à 35 % du poids total de l'ensemble des monomères ; et (d) un monomère acrylique ayant un groupe polaire copolymérisable avec les monomères (a) à (c), la quantité du monomère acrylique étant de 0,5 à 5 % du poids total de l'ensemble des monomères.
PCT/US2012/066956 2011-11-29 2012-11-29 Adhésif autocollant WO2013082222A1 (fr)

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CN201110388243.3A CN102719205B (zh) 2011-11-29 2011-11-29 压敏胶、压敏胶带及其制备方法和医用敷料
CN201110388243.3 2011-11-29

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JP2019014852A (ja) * 2017-07-10 2019-01-31 日本合成化学工業株式会社 粘着剤組成物、粘着剤および粘着シート
CN115779156A (zh) * 2022-12-16 2023-03-14 振德医疗用品股份有限公司 一种脱碘粘胶组合物及其手术膜
CN115820199A (zh) * 2022-12-09 2023-03-21 浙江工业大学 改性黑滑石抗菌导电压敏胶、医用电极片及其制备方法

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CN103865443B (zh) * 2012-12-07 2016-08-24 上海华谊丙烯酸有限公司 转移型粘合剂及其制备方法
CN105288812A (zh) * 2015-11-13 2016-02-03 合肥美迪普医疗卫生用品有限公司 一种气管插管固定装置
CN105885741A (zh) * 2016-05-17 2016-08-24 上海巍盛化工科技有限公司 一种医用压敏胶及医用敷料
CN107163866B (zh) * 2017-05-27 2020-09-15 江苏理工学院 一种医用紫外光固化水性导电压敏胶
CN109589445A (zh) * 2018-12-05 2019-04-09 广东高璐美数码科技有限公司 一种止汗剂改进的水性医疗压敏胶带及其制备方法
CN112107720A (zh) * 2020-09-18 2020-12-22 华熙生物科技股份有限公司 透气性好的医用压敏胶及依克多因在提高医用压敏胶透气性中的应用

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WO1984003837A1 (fr) 1983-04-07 1984-10-11 Minnesota Mining & Mfg Adhesif et materiau en feuille enduit d'adhesif pour la peau mouillee
US6680113B1 (en) 1989-12-29 2004-01-20 3M Innovative Properties Company Multi-layered dressing
EP0501124A1 (fr) * 1991-02-28 1992-09-02 National Starch and Chemical Investment Holding Corporation Composition d'adhésif sensible à la pression, perméable à la vapeur d'eau
WO1995026759A1 (fr) * 1994-04-01 1995-10-12 Minnesota Mining And Manufacturing Company Adhesif medical autocollant et pansement medical comportant cet adhesif
WO2001042384A2 (fr) * 1999-11-30 2001-06-14 Avery Dennison Corporation Adhesifs autocollants, permeables a la vapeur d'eau
WO2007038323A1 (fr) * 2005-09-23 2007-04-05 National Starch And Chemical Investment Holding Corporation Adhesifs acryliques a base de polymeres

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Publication number Priority date Publication date Assignee Title
JP2019014852A (ja) * 2017-07-10 2019-01-31 日本合成化学工業株式会社 粘着剤組成物、粘着剤および粘着シート
CN115820199A (zh) * 2022-12-09 2023-03-21 浙江工业大学 改性黑滑石抗菌导电压敏胶、医用电极片及其制备方法
CN115820199B (zh) * 2022-12-09 2024-05-03 浙江工业大学 改性黑滑石抗菌导电压敏胶、医用电极片及其制备方法
CN115779156A (zh) * 2022-12-16 2023-03-14 振德医疗用品股份有限公司 一种脱碘粘胶组合物及其手术膜

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CN102719205B (zh) 2015-02-18

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