Adhesives for bonding dissimilar materials in medical devices

Abstract

Bonding of dissimilar materials of medical device components can be performed by applying an adhesive to at least one surface of two components composed of dissimilar materials, contacting the surfaces, and exposing the contacted surfaces to heat and / or radiation to cure the adhesive and bond the surfaces. One medical component, e.g., medical tubing, can be composed of a non-polar polyvinyl chloride-free thermoplastic polymer material, while the other medical component, e.g., medical connectors, can be composed of polyacrylate, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), polyester, and / or polycarbonate materials. The adhesive formulation can include (a) a polyolefin oligomer having reactive acrylate and alkenyl groups, (b) an initiator, and optionally (c) a solvent.

Description

TECHNICAL FIELD

[0001] Cross-reference to Related Applications This application claims the priority benefit of U.S. Provisional Application No. 63 / 191,871, filed on May 21, 2021, the entire disclosure of which is incorporated herein by reference.

[0002] The present disclosure generally relates to bonding dissimilar materials of medical device components with an adhesive comprising (a) a polyolefin oligomer having reactive acrylate groups and pendant 1,2-vinyl groups along the polyolefin oligomer chain, (b) an initiator, and optionally (c) a solvent.

BACKGROUND ART

[0003] Assemblies of tubes, valves, fittings, and spikes that connect a fluid container to a patient, with or without an infusion pump, are sometimes referred to as "IV sets". Infusion sets are constructed by joining a plurality of polymer tube segments to a plurality of polymer components. Joints are typically formed by applying a thin layer of solvent or adhesive to one or both of the contact surfaces, then bringing the two surfaces together.

[0004] However, infusion sets are increasingly constructed from non-polyvinyl chloride materials such as thermoplastic elastomers and polyolefins, which, due to their relative chemical inertness, are difficult to bond to other medical components, particularly components made of different polymeric materials. Accordingly, a more significant issue in manufacturing infusion sets using tubes made from thermoplastic elastomers is consistently joining such tubes and infusion components to obtain safe and / or leak-free joints with desired fluid flow.

[0005] Therefore, there is an ongoing need to provide leak-proof joints between medical tubing and rigid connectors, and / or between needles and connector hubs, using polyvinyl chloride-free materials, particularly for medical devices, that improve adhesion, enhance resistance to aggregation failure, and provide such joints. [Overview of the project]

[0006] Aspects of this technology relate to adhesive formulations comprising (a) a polyolefin oligomer having reactive acrylate groups and reactive alkenyl groups, (b) an initiator such as a thermal or photoinitiator, and optionally (c) a solvent. The adhesive is adapted to bond dissimilar materials of medical device components. Advantageously, the reactive polyolefin oligomer comprises a non-polar primary polymer backbone, reactive alkenyl groups such as alkenes or pendant 1,2 vinyl groups along the polyolefin oligomer chain, and polar terminal segments containing polar linking groups such as carbamates (urethane groups), and esters linking reactive (meth)acrylate terminal groups. Furthermore, in addition to acrylate and vinyl groups, the reactive polyolefin oligomer may contain any functional groups that can react to form covalent bonds in response to external stimuli such as heat, light, or ionizing radiation. Polyolefin oligomers having reactive acrylate groups can have a number average molecular weight of about 500 to about 30,000 g / mol, for example, about 500 to about 10,000 or 5,000 or 3,000 g / mol. Furthermore, although this may overlap with other descriptions, various aspects of the present invention are shown below. However, the present invention is not limited to the following. [1] A method for joining dissimilar materials of medical device components, The aforementioned method, Applying an adhesive to the surface of one medical component made of a non-polar, non-polyvinyl chloride thermoplastic polymer material, or to the surface of another medical component made of polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate, or to both such surfaces, Bringing the aforementioned surfaces into contact, In order to crosslink the adhesive and bond the surfaces, the contacted surfaces are exposed to heat or light radiation, Sterilizing the bonded surfaces, Includes, A method wherein the adhesive compound comprises (a) a polyolefin oligomer having a reactive acrylate group and an alkenyl group, (b) an initiator, and optionally (c) a solvent. [2] The method according to [1], further comprising subjecting the bonded surfaces to sterilization by ionizing radiation. [3] The method according to [1], wherein the one medical component is a medical tube. [4] The method according to [3], wherein the tube comprises a styrene-containing thermoplastic elastomer. [5] The method according to [1], wherein the other medical components include a medical connector composed of an acrylic polymer, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate material, polyester, polycarbonate, or a combination thereof. [6] The method according to [1], wherein one medical component comprises a medical tube made of a styrene-containing thermoplastic elastomer, and the other medical component comprises a medical connector made of an acrylic polymer, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate material, polyester, polycarbonate, or a combination thereof. [7] The method according to [1], wherein the initiator comprises a photopolymerization initiator. [8] The method according to [1], wherein the adhesive compound comprises a solvent. [9] The method according to any one of [1] to [8], wherein the polyolefin oligomer having a reactive acrylate group comprises the polybutadiene oligomer having a reactive acrylate group bonded to the polybutadiene oligomer along the polybutadiene oligomer chain via carbamate bonds and / or pendant 1,2 vinyl groups.

[10] An adhesive formulation for bonding together polyvinyl chloride-free materials, comprising (a) a polyolefin oligomer having reactive acrylate groups and pendant 1,2 vinyl groups along a polyolefin oligomer chain, and (b) an initiator and optionally (c) a solvent.

[11] The polyolefin oligomer having a reactive acrylate group is of formula (I) [C1] JPEG0007933800000001.jpg34127 (In the formula, R 1 (where n represents an acrylate or methacrylate portion bonded to a polyolefin chain via a urethane bond, where n is an integer between 10 and approximately 500, and m is an integer between 0 and approximately 250.) The adhesive formulation according to

[10] , comprising a polybutadiene oligomer having a reactive acrylate group represented by .

[12] The adhesive formulation according to

[10] , wherein the initiator comprises a photopolymerization initiator.

[13] The adhesive formulation according to any one of

[10] to

[12] , wherein the polyolefin oligomer comprises at least 50% by weight of the reactive component of the adhesive formulation.

[14] An infusion set comprising a tube made of a non-polar polyvinyl chloride-free thermoplastic polymer material bonded to a medical connector with a curing adhesive formulation as described in any of

[10] to

[13] .

[15] The infusion set according to

[14] , wherein the tube comprises a styrene-containing thermoplastic elastomer, and the medical connector is composed of an acrylic polymer, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate material, polyester, polycarbonate, or a combination thereof.

[0007] Further aspects of this technology relate to bonding dissimilar materials of medical device components by applying an adhesive to the surface of one medical component made of a non-polar, non-polyvinyl chloride thermoplastic polymer material, or to the surface of another medical component made of polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate, or to both such surfaces; exposing the contacted surfaces to heat or light radiation to crosslink the adhesive and bond the surfaces; and sterilizing the bonded surfaces. Sterilization may advantageously include sterilization by ionizing radiation, which can further induce chemical reactions of the adhesive.

[0008] Another aspect of the present technology relates to an infusion set comprising a tube made of a non-polar polyvinyl chloride-free thermoplastic polymer material bonded to a medical connector by a cured adhesive formulation, wherein the adhesive formulation comprises (a) a polyolefin oligomer having reactive acrylate groups and alkenyl groups, (b) an initiator, and optionally (c) a solvent.

[0009] The embodiments include one or more of the following features individually or in combination: For example, one medical component to be joined may be a medical tube, and the other medical component may be a medical connector, the tube may include a styrene-containing thermoplastic elastomer, and for example, the connector may be composed of an acrylic polymer, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate material, polyester, polycarbonate, or a combination thereof.

[0010] Further advantages of this technology will be readily apparent to those skilled in the art from the detailed description below, and only specific aspects of this technology are shown and described merely as examples. As will be understood, other different configurations of this technology are possible, and some of its details can be modified in various other ways, all without departing from this technology. Therefore, the drawings and description should be considered as illustrative and not as limiting.

[0011] To provide further understanding, the accompanying drawings, which are included and incorporated herein and constitute part of herein, illustrate the disclosed embodiments and help illustrate the principles of the disclosed embodiments together with the description. [Brief explanation of the drawing]

[0012] [Figure 1] This plot shows the difference in tensile strength between sample adhesive formulations that were not exposed to radiation and those that were not exposed to UV / gamma rays. The UV / gamma ray treated group is statistically significant (p=0.000).

[0013] [Figure 2] Figures 2A and 2B plot the difference in tensile strength between sample adhesive formulations that were not exposed to radiation and those that were not exposed to UV / gamma rays. The UV / gamma ray treated group is statistically significant (p=0.000).

[0014] [Figure 3] This is a plot of the difference in tensile force of sample adhesive formulations subjected to various radiation conditions. [Modes for carrying out the invention]

[0015] The detailed descriptions below illustrate various configurations of the Art and are not intended to represent only the configurations in which the Art may be implemented. The detailed descriptions include specific details for the purpose of providing a complete understanding of the Art. Therefore, dimensions are provided for certain embodiments as non-limiting examples. However, it will be apparent to those skilled in the art that the Art may be implemented without these specific details. In some examples, well-known structures and components are shown in block diagram form to avoid obscuring the concepts of the Art.

[0016] This disclosure includes examples of the technology and should not be understood as limiting the scope of the appended claims. Herein, various aspects of the technology are disclosed in accordance with specific but non-limiting examples. The various embodiments described herein can be carried out in different ways and variations according to the desired use or implementation.

[0017] Aspects of this technology relate to adhesive formulations (or simply adhesives) comprising (a) a polyolefin oligomer having reactive acrylate groups and alkenyl groups, (b) an initiator such as a thermal or photoinitiator, and optionally (c) a solvent. Advantageously, the reactive polyolefin oligomer comprises a non-polar primary polymer backbone, a polar terminal segment containing a non-polar primary polymer backbone, reactive alkenyl groups such as alkenes or pendant 1,2 vinyl groups along the polyolefin oligomer chain, and polar linking groups such as carbamates (urethane groups), and an ester linking the reactive (meth)acrylate terminal groups. Furthermore, in addition to acrylate and vinyl groups, the reactive polyolefin oligomer may contain any functional groups that can react to form covalent bonds in response to external stimuli such as heat, light, or ionizing radiation. The adhesive may further comprise an acrylate monomer component copolymerized with the polyolefin oligomer, viscosity modifiers, tackifiers and / or inhibitors, such as free radical inhibitors, to extend the shelf life of the thermal or photocurable adhesive formulation.

[0018] Advantageously, the polyolefin oligomer having reactive acrylate groups constitutes the main component (at least 50% by weight) of the reactive component of the adhesive. In some embodiments, the adhesive formulation contains at least 60%, 70%, 80%, or more (by weight) of reactive polyolefin oligomer as the reactive component of the adhesive. The adhesive can be cured by two distinct modes due to two different types of reactive groups of the polyolefin oligomer. Namely, the acrylate groups can be cured by photocuring, and the 1,2-vinyl groups can be cured by ionizing radiation (e.g., e-beam and / or gamma rays) under conditions useful for sterilizing medical devices. The 1,2-vinyl groups, which tend to react with ionizing radiation, can also react with components and constituents in the adhesive and mating surfaces, thereby increasing the strength of the bond.

[0019] The adhesive formulations of this disclosure are adapted to bond dissimilar materials of medical device components, such as medical device components made from generally non-polar, polyvinyl chloride-free thermoplastic polymer materials, to medical device components made from generally polar acrylic polymer materials, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate materials, polyester, polycarbonate, etc. Medical device components made from non-polyvinyl chloride thermoplastic polymer materials include medical tubing, while medical device components made from polyacrylate, polyacrylonitrile, polyester, polycarbonate, etc., include rigid connectors such as spikes, male Luer, needleless valve connectors, and rigid couplers. The adhesive formulations of this disclosure are further adapted to withstand sterilization by heat, chemicals, or radiation (e.g., sterilization by heat, ethylene oxide, or gamma rays), which is a common practice for medical devices, so that the medical device undergoes such sterilization after the surfaces have been bonded with adhesive.

[0020] The adhesive formulations of this disclosure may be advantageously used to bond dissimilar materials of medical device components by applying the adhesive to the surface of one medical component made of a non-polar, non-polyvinyl chloride thermoplastic polymer material, or to the surface of another medical component made of polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate, or to both such surfaces, bringing the surfaces having the applied adhesive into contact, and exposing the contacted surfaces to heat or radiation in order to crosslink the adhesive and bond the surfaces. The radiation may include (i) optical radiation such as UV radiation, and (ii) ionizing radiation such as e-beams and / or gamma rays.

[0021] In certain embodiments, one medical component may consist of a non-polar, non-polyvinyl chloride thermoplastic polymer material, and may be a medical tube made of a non-polyvinyl chloride thermoplastic polymer material. In other embodiments, other medical components may consist of polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate, and may be a rigid connector or coupler made of polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate.

[0022] Exemplary adhesive formulations of this disclosure include, but are not limited to, polyolefin oligomers having reactive acrylate groups (i.e., at least two reactive acrylate groups) and reactive pendant 1,2 vinyl groups along a polyolefin oligomer chain. Such polyolefin oligomers may be polybutadiene oligomers having reactive acrylate groups, or acrylic-modified chlorinated polyolefins with or without maleic anhydride functionality. Such reactive polyolefin oligomers may have polar groups that bond reactive acrylate to the olefin, such as polybutadiene acrylate resins having (meth)acrylic groups bonded to both ends of the polybutadiene chain via urethane linking groups. Additional reactive groups, such as epoxy groups and maleic anhydride residues, may also be included in the polyolefin oligomers. Polyolefin oligomers having reactive acrylate groups may have a number average molecular weight of about 500 to about 30,000 g / mol, for example, about 500 to about 10,000 or 5,000 or 3,000 g / mol.

[0023] The use of polyolefin oligomers having reactive acrylate groups in the adhesive formulations of this disclosure has the advantage that the repeating units of the reactive polyolefin are similar to one of the non-polar thermoplastic polymer materials of the medical component being bonded, thus resulting in an affinity for thermoplastic materials. Furthermore, the acrylate and other polar groups on the reactive polyolefin oligomer can create an affinity for other medical device components made from polar materials. For example, urethane or carbamate are strong polar groups that promote surface interactions with polar surfaces of rigid plastics by dipole-dipole moments or hydrogen bonds.

[0024] Furthermore, in contrast to monomer components, the use of oligomers results in smaller volume shrinkage during polymerization and minimizes the change in filling volume of the gaps in the bonding interface region. Therefore, it is expected that potential leakage of bonding components can be improved. Another advantage of certain polyolefin oligomers having reactive acrylate groups in the adhesive formulations of this disclosure is that, after sterilization from gamma or electron beam radiation, the reaction of residual reactive groups such as 1,2-vinyl groups can continue, allowing the adhesive to further cure. For example, (meth)acrylate functional end groups and 1,2-vinyl side chains undergo crosslinking reactions to generate a highly crosslinked network, forming a thermosetting resin with high tensile strength.

[0025] In one aspect of the present disclosure, the polyolefin oligomer having a reactive acrylate group in the adhesive formulation of the present disclosure includes a polybutadiene oligomer having a reactive acrylate group represented by the following formula (I). [ka]

[0026] In the formula, R1 represents an acrylate or methacrylate moiety, n is an integer from 10 to about 500, e.g., 10 to about 100, and m is an integer from 0 to about 250, e.g., 0 to about 100. In one aspect of the present disclosure, a polybutadiene oligomer having a reactive acrylate group may have a number-average molecular weight of about 500 to about 30,000 g / mol, e.g., about 500 to about 10,000 or 5,000 or 3,000 g / mol. The acrylate or methacrylate moiety may be represented as shown below. [ka]

[0027] In the formula, R2 represents H or methyl.

[0028] Other polyolefin oligomers having reactive acrylate groups in the adhesive formulations of this disclosure may include those shown in Scheme 1 below. [ka] Scheme 1

[0029] Such polyolefin oligomers having reactive acrylate groups bonded to the polyolefin oligomer chain via polar ester bonds also contain reactive alkenyl groups along the polyolefin oligomer chain.

[0030] The adhesive formulations of this disclosure may also contain, but are not limited to, acrylate monomer components such as isobornyl acrylate (IBOA), methyl acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, tert-butyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, decyl acrylate, isodecyl acrylate, isooctyl acrylate, lauryl acrylate, octadecyl acrylate, tridecyl acrylate, 2-naphthyl acrylate, and benzyl acrylate.

[0031] The adhesive formulation may also contain one or more initiators for initiating the crosslinking of the reactive groups of a polyolefin oligomer having reactive acrylate groups and / or other monomer components. Useful initiators that may be included in the adhesive formulation of this disclosure include, for example, thermal polymerization initiators and photopolymerization initiators.

[0032] A thermal polymerization initiator is a compound that generates a radical or cation when exposed to heat. For example, azo compounds such as 2,2'-azobis(isobutyronitrile) (AIBN), 2,2'-azoddi(2-methylbutyronitrile) (AMBN), and 2,2'-azobis(2,4-dimethylvaleronitrile) (ADVN), as well as organic peroxides such as benzoyl peroxide (BPO), tert-butyl hydroperoxide (TBHP) thermal radical initiators, benzenesulfonic acid esters, and alkylsulfonium salts, can be used as thermal initiators in the adhesives of this disclosure.

[0033] The adhesive formulation may also contain a photopolymerization initiator that generates free radicals upon light irradiation, such as ultraviolet irradiation, which may also be used in the adhesives of this disclosure, or alternatively, include, for example, ketones available as Darocur 1173, benzophenone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, diphenylphosphine oxide initiators, such as diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide available as Irgacure® TPO, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (Irgacure 819), etc.

[0034] The solvents that can be used in the adhesive formulations of this disclosure include, but are not limited to, one or more alcohols such as methanol, ethanol, isopropanol, propanol, butanol, pentanol, and benzyl alcohol; glycols such as diethylene glycol and propylene glycol; ethers such as dioxolane, tetrahydrofuran, and 1,3-dioxane; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; esters such as ethyl acetate and ethyl formate; amides such as dimethylformamide, dimethyl and diethylacetamide; sulfoxides such as N-methylpyrrolidone and dimethyl sulfoxide; hydrocarbons such as hexane; and chlorinated solvents such as toluene and methylene chloride.

[0035] The adhesive formulations of this disclosure are useful for bonding dissimilar medical device components, such as components of an infusion set, including medical tubing and connectors for administering medication via infusion.

[0036] In certain embodiments, tubes for intravenous administration may include non-polyvinyl chloride (PVC) thermoplastic polymers and / or silicone materials. Such materials include, for example, one or more thermoplastic elastomers such as silicone, thermoplastic olefins (TPO), thermoplastic elastomers (TPE), e.g. styrene-containing thermoplastic elastomers (S-TPE), e.g. styrene block copolymers (SBC), e.g. styrene-butadiene-styrene-styrene copolymers (SBS), styrene-butadiene-styrene-styrene block copolymers (SBSS), styrene-isoprene-styrene (SIS), and polyolefin elastomers (POE), or blends thereof. To improve thermal oxidation stability and UV stability, unsaturated rubber blocks of S-TPE elastomers (e.g., polybutadiene or polyisoprene rubber blocks of SBS, SBSS, or SIS polymers) can be hydrogenated to form hydrogenated styrene-based thermoplastic elastomers, including, but not limited to, styrene-ethylene-butylene-styrene thermoplastic elastomers (SEBS) and styrene-ethylene / propylene-styrene (SEPS). High-performance thermoplastic elastomers (TPEs) are designed as a sustainable alternative to flexible PVC for medical tubing and films. Furthermore, tubing can include blends of hydrogenated styrene-based thermoplastic elastomers with hydrogenated or saturated polyolefins such as polypropylene, including homo, block, and / or random polypropylenes, such as random copolymer polypropylene (RCPP).

[0037] Such exemplary materials may be optically transparent, thermally stable, chemically and radiologically sterilizable (e.g., sterilized by heat, ethylene oxide, or ionizing radiation), and physiologically inert. Such exemplary materials may also be environmentally compatible and can be incinerated with minimal pollutants.

[0038] The tube of this disclosure may have an inner diameter through which the fluid flows in the range of approximately 0.1 mm to approximately 3.5 mm, for example, approximately 0.5 mm to approximately 2.5 mm, and the overall thickness of the side wall may be in the range of 0.1 mm to 2 mm, for example, approximately 0.4 mm to approximately 1 mm.

[0039] The tubing of this disclosure is particularly useful in conjunction with intravenous assemblies, gravity vessels, and / or infusion pumps for the delivery of intravenous fluids to a patient. An assembly of tubing, valves, fittings, and spikes that intravenously connects a fluid vessel to a patient may be referred to as an "IV set." An infusion pump is a medical device that may be used to administer intravenous (IV) fluids. Such assemblies, vessels, and pumps may be useful on their own, using tubing coupled to one or more medical connectors and tubing of this disclosure.

[0040] For example, a tube according to the present disclosure can be easily mated and bonded to a medical connector or other medical component by applying a thin layer of the adhesive of the present disclosure to one or both of the contact surfaces. After the adhesive is applied, the tube surface and the surface of the other medical component are brought into contact and exposed to heat and / or radiation to crosslink the adhesive and bond the surfaces. The contact surface of the tube may be an inner diameter, an outer diameter, or both, depending on whether the contact surfaces to be bonded are an inner layer, an outer layer, or both. The adhesive may be applied to the inside, the outside, or both.

[0041] Medical connectors that can benefit from this disclosure include, but are not limited to, connectors made of acrylic polymer materials, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate materials, polyester, polycarbonate, or combinations thereof.

[0042] In one embodiment of this application, a tube according to the present disclosure can be easily mated and coupled to a medical connector by applying an adhesive to the surface of the tube, or to the surface of a medical component such as a medical connector, or to both the surface of the tube and the surface of the medical component. The surfaces to which the adhesive is applied are brought into contact, and the contacted surfaces are exposed to heat or radiation to crosslink the adhesive and bond the surfaces. The bonded medical component can then be sterilized by heat, chemicals or radiation. In certain embodiments, if the adhesive contains a polyolefin oligomer having pendant vinyl groups, gamma sterilization further cures the adhesive to form a stronger bond on the mated surface. [Examples]

[0043] The following examples are intended to further illustrate, and not to limit, certain aspects of the present technology. Those skilled in the art will be able to recognize or confirm many equivalents to the specific embodiments of the invention described herein by means of routine experimentation alone.

[0044] A series of adhesive formulations were prepared by combining one of two grades of polybutadiene acrylate resin with (meth)acrylic groups bonded to both ends of a polybutadiene chain via urethane linking groups. Such resins are commercially available from Nippon Soda Co., Ltd. as TE-2000 and TEAI-1000. The chemical structures and properties of these resins are shown in Scheme 2 and Table 1 below. TE-2000 [ka] TEAI-1000 [ka] Scheme 2 [Table 1]

[0045] The following six samples were prepared as described.

[0046] Sample 1: Experimental studies were conducted to develop a formulation containing TE2000 dissolved in methyl ether ketone (MEK) in order to prepare a solution with uniform viscosity at a 50% w / w concentration.

[0047] Sample 2: Experimental studies were conducted to develop a formulation containing TEAI-1000 dissolved in methyl ether ketone in order to prepare a solution with uniform viscosity at a 50% w / w concentration.

[0048] Sample 3: 7 g of 50% TE-2000 (3.5 g of TE-2000) from Sample 1 was mixed with 0.1 g of the photoinitiator Irgacure 819 to achieve a weight ratio of 70:2 for TE-2000 to Irgacure 819.

[0049] Sample 4: 7 g of 50% TEAI-1000 (3.5 g of TE-2000) from Sample 2 was mixed with 0.1 g of the photoinitiator Irgacure 819 to a weight ratio of 70:2.

[0050] Sample 5: To 7 g of 50% TE-2000 (3.5 g of TE-2000) from Sample 1, 1.5 g of isobornyl acrylate (IBOA) and 0.1 g of Irgacure 819 were added to prepare a solution of TE-2000, isobornyl acrylate (IBOA), and Irgacure 819 in a weight ratio of 70:30:2.

[0051] Sample 6: To 7 g of 50% TEAI-1000 (3.5 g of TE-2000) from Sample 2, 1.5 g of IBOA and 0.1 g of Irgacure 819 were added to prepare a solution of TEAI-1000, IBOA, and Irgacure 819 in a weight ratio of 70:30:2.

[0052] Assembly joining and processing of styrene-based TPE tubing into female pocket luer connectors:

[0053] Extruded styrene-based block copolymer TPE tubes with dimensions of ID 0.107 inches and OD 0.145 inches were each cut to a length of 3 inches, and then a thin layer of adhesive coating was applied to the outer surface of the tubes in a range of approximately 0.5 inches in length using a cotton Q tip. The adhesive was derived from the prepared samples 1-6 described above. The adhesive-coated tube segments were manually and fully inserted into the female pockets of a Luer connect (mABS material) until they stopped and engaged securely. The assemblies were then UV-cured for 20 seconds using a 365 nm LED. The UV output was 1-1.5 W / cm². 2 The curing distance between the LED head and the assembly joint was 1 inch. The assembly was also sterilized with gamma rays to test its effectiveness from gamma radiation with doses of 21.4–35 kGy.

[0054] Measurement of joint assembly separation force using Instron:

[0055] A tensile strength test was performed using a standard test (Instron) at a strain rate of 20 inches / minute. The luer connector was positioned in a retaining fixture, and the upper gripper was then adjusted to clamp onto the tube 1 inch away from the opening of the coupling pocket.

[0056] The tensile force results (sample size 5) for sample groups under different processing conditions (UV, gamma) are shown in Table 2 below, along with the failure modes (TPO = tube pull-out, TB = tubing break). [Table 2]

[0057] The adhesive compositions of Samples 1 and 2 contained polybutadiene with acrylate reactive groups and the solvent MEK. Although no UV or thermal initiators were present in the adhesive compositions, tensile strength increased by 25% in Sample 1 and 18% in Sample 2 after UV and gamma treatment (Figure 1A). Figure 2 shows the results of a mini-tab of statistical improvement after UV / gamma sterilization.

[0058] Tensile force data from adhesive samples 3, 4, 5, and 6 were collected in Table 2, and the percentage change in tensile force from each treatment condition, as shown in Table 3, was plotted in Figure 3 for comparison under different treatment conditions. [Table 3]

[0059] Furthermore, to understand whether the change in tensile force was statistically significant during treatment, ANOVA analysis was performed using graph plots, and Tukey's comparative study was demonstrated below for samples 3–6. The analysis showed that for samples 3–6, treatment (gamma, UV, or a combination of UV and gamma) was necessary to improve the statistically significant tensile force derived from the control.

[0060] In addition to the components listed for the sample, other thermal and / or photoinitiators may be used. Viscosity modifiers may be used for manufacturability and ease of assembly. The adhesive formulation may be diluted with additional suitable organic solvents and may further contain tackifiers. Furthermore, free radical inhibitors such as HQ, BHT, and MEHQ may be added to extend the shelf life of the thermal or photocurable adhesive formulation.

[0061] Any particular order or hierarchy of blocks in the disclosed process method is to be understood as an example of an exemplary technique. Based on design or implementation preferences, any particular order or hierarchy of blocks in the process may be rearranged, or all illustrated blocks may be executed. In some implementations, any of the blocks may be executed simultaneously.

[0062] This disclosure is provided to enable those skilled in the art to carry out various embodiments described herein. This disclosure provides various examples of the art, and the art is not limited to these examples. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the general principles defined herein may be applied to other embodiments.

[0063] References to singular elements, unless otherwise specified, mean "one or more," not "one and only one." Unless otherwise specified, the term "several" refers to one or more. Masculine pronouns (e.g., his) include feminine and neuter genders (e.g., her and its), and vice versa. Headings and subheadings, where present, are used for convenience only and do not limit the invention.

[0064] The term “exemplary” is used herein to mean “serving as an example or illustration.” An embodiment or design described herein as “exemplary” should not necessarily be construed as being preferable or advantageous to other embodiments or designs. In one embodiment, various alternative configurations and operations described herein may be considered at least equivalent.

[0065] When used herein, the phrase “at least one” preceding a set of items, along with the term “or” to separate any of the items, modifies the entire list, rather than each individual item in the list. The phrase “at least one” does not require the selection of at least one item. Rather, the phrase allows for meanings including at least one of any one of the items, and / or at least one of any combination of the items, and / or at least one of each of the items. For example, the phrase “at least one of A, B, or C” could refer to A only, B only, or C only, or any combination of A, B, and C.

[0066] The terms "aspects" and similar phrases do not imply that such aspects are essential to the Art or that such aspects apply to all configurations of the Art. Disclosures relating to aspects may apply to all configurations or to one or more configurations. An aspect may provide one or more examples. A term such as "one aspect" may refer to one or more aspects, and vice versa. The terms "aspects" and similar phrases do not imply that such aspects are essential to the Art or that such aspects apply to all configurations of the Art. Disclosures relating to embodiments may apply to all embodiments or to one or more embodiments. An aspect may provide one or more examples. A term such as "one aspect" may refer to one or more aspects, and vice versa. The terms "aspects" and similar phrases do not imply that such aspects are essential to the Art or that such aspects apply to all configurations of the Art. Disclosures relating to configurations may apply to all configurations or to one or more configurations. A configuration may provide one or more examples. The term "such configuration" may refer to one or more configurations, and vice versa.

[0067] In one embodiment, unless otherwise specified, all measurements, values, ratings, locations, sizes, dimensions, and other specifications described herein, including the following claims, are approximate and not precise. In one embodiment, they are intended to have a reasonable range that is consistent with the functions to which they relate and with those commonly used in the art to which they relate.

[0068] The specific sequence or hierarchy of steps, actions, or processes disclosed is understood to be illustrative of an exemplary method. It is understood that the specific sequence or hierarchy of steps, actions, or processes may be rearranged based on design preferences. Some of the steps, actions, or processes may be performed simultaneously. Some or all of the steps, actions, or processes may be performed automatically without user intervention. The attached method claims present various elements of steps, actions, or processes in a sample sequence, if any, and are not limited to the specific sequence or hierarchy presented.

[0069] All structural and functional equivalents of elements of various aspects described herein, known to those skilled in the art, or to become known to those skilled in the art, are expressly incorporated herein by reference and are intended to be included in the claims. Furthermore, nothing disclosed herein is intended to be exclusive to the public, whether such disclosure is expressly included in the claims or not. No element of a claim should be construed under 35 U.S.C. § 112(f) unless the element is expressly described using the phrase “means for” or, in the case of a method claim, the element is described using the phrase “steps for.” Furthermore, to the extent that terms such as “include” and “have” are used, such terms are intended to be as comprehensive as the term “comprise,” as “comprise” is construed when “comprise” is used as a transitional term in the claims.

[0070] The title, background art, summary, brief description of the drawings, and abstract of this disclosure are incorporated herein by reference and are provided as exemplary examples of the disclosure, not as limiting descriptions. They are submitted with the understanding that they are not to be used to limit the claims or their meaning. Furthermore, in the detailed description, it will be found that the description provides exemplary examples and various features in various embodiments are grouped together for the purpose of simplifying the disclosure. This method of disclosure should not be construed as reflecting an intention that the claimed subject matter requires more features than expressly described in each claim. Rather, as reflected in the following claims, the subject matter of the invention lies in fewer features than all features of a single disclosed configuration or operation. The following claims are incorporated in the detailed description, and each claim stands alone as separately claimed subject matter.

[0071] The claims are not intended to be limited to the embodiments described herein, but are given the full scope consistent with the language claims and encompass all legal equivalents. Nevertheless, none of the claims are intended, nor should they be construed, to encompass subject matter that does not satisfy the requirements of 35 U.S.C § 101, 102, or 103.

Claims

1. A method for joining dissimilar materials of medical device components, The aforementioned method, Applying an adhesive to the surface of one medical component made of a non-polar, non-polyvinyl chloride thermoplastic polymer material, or to the surface of another medical component made of polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate, or to both such surfaces, Bringing the aforementioned surfaces into contact, In order to crosslink the adhesive and bond the surfaces, the contacted surfaces are exposed to heat or light radiation, Sterilizing the bonded surfaces, Includes, The adhesive compound comprises (a) a polyolefin oligomer having a reactive acrylate group and an alkenyl group, (b) an initiator, and optionally (c) a solvent. The aforementioned polyolefin oligomer is of formula (I) 【Chemistry 1】 (In the formula, R １ (where n represents an acrylate or methacrylate portion bonded to a polyolefin chain via a urethane bond, where n is an integer from 10 to 500 and m is an integer from 0 to 250) It is represented as, A method comprising a medical connector comprising one medical component comprising a styrene-containing thermoplastic elastomer, and the other medical component comprising an acrylic polymer, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate material, polyester, polycarbonate, or a combination thereof.

2. The method according to claim 1, further comprising subjecting the bonded surfaces to sterilization with ionizing radiation.

3. The method according to claim 1, wherein the one medical component is a medical tube.

4. The method according to claim 1, wherein the initiator comprises a photopolymerization initiator.

5. The method according to claim 1, wherein the adhesive compound comprises a solvent.

6. The method according to any one of claims 1 to 5, wherein the polyolefin oligomer having a reactive acrylate group comprises a polybutadiene oligomer having a reactive acrylate-terminated group bonded to the polybutadiene oligomer along a polybutadiene oligomer chain via carbamate bonds and pendant 1,2 vinyl groups.

7. An infusion set comprising a tube made of a non-polar polyvinyl chloride-free thermoplastic polymer material bonded to a medical connector by a curing adhesive formulation comprising (a) a polyolefin oligomer having reactive acrylate-terminated groups and pendant 1,2 vinyl groups along a polyolefin oligomer chain, and (b) an initiator and optionally (c) a solvent, The polyolefin oligomer having a reactive acrylate group is of formula (I) 【Chemistry 2】 (In the formula, R1 represents an acrylate or methacrylate portion bonded to a polyolefin chain via a urethane bond, n is an integer from 10 to 500, and m is an integer from 0 to 250.) The polybutadiene oligomer having a reactive acrylate group represented by the following: An infusion set comprising one medical component comprising a styrene-containing thermoplastic elastomer, and the other medical component comprising a medical connector composed of an acrylic polymer, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate material, polyester, polycarbonate, or a combination thereof.

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