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 priority to U.S. Provisional Application No. 63 / 191,871, filed May 21, 2021, the entire disclosure of which is incorporated herein by reference.

[0002] The present disclosure relates generally to bonding dissimilar materials of medical device components with adhesives that include (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 technology]

[0003] An assembly of tubing, valves, fittings, and spikes that connects a fluid container to a patient with or without an infusion pump is sometimes called an "IV set." Infusion sets are constructed by joining multiple polymeric tubing segments to multiple polymeric components. The joints are typically formed by applying a thin layer of solvent or adhesive to one or both of the contacting surfaces and then mating the two surfaces together.

[0004] However, infusion sets are increasingly being constructed of 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, especially components made of different polymeric materials. Thus, a more significant issue in manufacturing infusion sets using tubing made from thermoplastic elastomers is consistently bonding such tubing and infusion components to obtain a safe and / or leak-free joint with the desired fluid flow.

[0005] Thus, there is a continuing need to improve adhesion, improve cohesive failure resistance, and provide leak-proof joints between medical tubing and rigid connectors and / or needles to connector hubs, particularly with polyvinyl chloride-free materials for medical devices. Summary of the Invention

[0006] An embodiment of the present technology relates to an adhesive formulation comprising (a) a polyolefin oligomer having reactive acrylate 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 end segments comprising polar linking groups such as carbamates (urethane groups), esters linking the reactive (meth)acrylate end groups. Furthermore, the reactive polyolefin oligomer can comprise any functional group in addition to acrylate and vinyl groups that can react to form a covalent bond in response to an external stimulus such as heat, light, or ionizing radiation. The polyolefin oligomer having reactive acrylate groups can have a number average molecular weight of from about 500 to about 30,000 g / mol, for example, from about 500 to about 10,000 or 5,000, or 3,000 g / mol.

[0007] Further aspects of the present technology relate to bonding dissimilar materials of medical device components by applying an adhesive onto the surface of one medical component composed of a non-polar non-polyvinyl chloride thermoplastic polymeric material, or onto the surface of the other medical component composed of polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate, or onto both such surfaces, contacting and exposing the contacted surfaces to heat or light radiation to crosslink the adhesive and bond the surfaces, and sterilizing the bonded surfaces. Sterilization can advantageously further induce a chemical reaction of the adhesive and can include sterilization by ionizing radiation, etc.

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

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

[0010] Further advantages of the present technology will become readily apparent to those skilled in the art from the following detailed description, in which only certain aspects of the present technology are shown and described merely by way of example. As will be understood, the present technology is capable of other different configurations, and its several details are capable of modification in various other respects, all without departing from the present technology. Accordingly, the drawings and description should be regarded as illustrative in nature, and not as restrictive.

[0011] The accompanying drawings, which are included to provide a further understanding, are incorporated in and constitute a part of this specification, illustrate disclosed embodiments and, together with the description, serve to explain the principles of the disclosed embodiments. [Brief description of the drawings]

[0012] [Figure 1] 1 is a plot of the difference in tensile force of sample adhesive formulations that were not subjected to radiation and UV / gamma radiation. The UV / gamma radiation treatment group is statistically significant (p=0.000).

[0013] [Diagram 2] Figures 2A and 2B are plots of the difference in tensile force for sample adhesive formulations that were not exposed to radiation and UV / gamma radiation. The UV / gamma radiation treatment group is statistically significant (p=0.000).

[0014] [Diagram 3] 1 is a plot of the difference in tensile force of sample adhesive formulations subjected to various radiation conditions. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] The detailed description described below describes various configurations of the present technology and is not intended to represent the only configurations in which the present technology can be implemented. The detailed description includes specific details for the purpose of providing a thorough understanding of the present technology. Thus, dimensions are provided for specific embodiments as non-limiting examples. However, it will be apparent to those skilled in the art that the present technology can be implemented without these specific details. In some instances, well-known structures and components are shown in block diagram form to avoid obscuring the concepts of the present technology.

[0016] It should be understood that the present disclosure includes examples of the present technology and does not limit the scope of the appended claims. Various aspects of the present technology are disclosed herein according to specific, but non-limiting examples. The various embodiments described in the present disclosure can be implemented in different ways and with modifications according to a desired application or implementation.

[0017] An embodiment of the present technology relates to an adhesive formulation (or adhesive for short) comprising: (a) a polyolefin oligomer having reactive acrylate 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, reactive alkenyl groups, such as alkenes or pendant 1,2 vinyl groups along the polyolefin oligomer chain, and polar end segments comprising polar linking groups, such as carbamates (urethane groups), esters linking the reactive (meth)acrylate end groups. Furthermore, the reactive polyolefin oligomer may comprise any functional group, in addition to acrylate and vinyl groups, that may react to form a covalent bond in response to an external stimulus, such as heat, light, or ionizing radiation. The adhesive may further comprise an acrylate monomer component that copolymerizes 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 with reactive acrylate groups is the major component (at least 50% by weight) of the reactive component of the adhesive. In some embodiments, the adhesive formulation comprises at least 60%, 70%, 80% or more (by weight) of the reactive polyolefin oligomer as the reactive component of the adhesive. The adhesive can be cured by two separate modes due to the two different types of reactive groups of the polyolefin oligomer. That is, 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 radiation) under conditions useful for sterilization of medical devices. The 1,2 vinyl groups, which tend to react by ionizing radiation, can also react with components and constituents in the adhesive and mating surfaces, which increases the strength of the bond.

[0019] The adhesive formulations of the present 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-based polymer materials, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate-based materials, polyesters, polycarbonates, etc. Medical device components made from non-polyvinyl chloride thermoplastic polymer materials include medical tubing, and medical device components made from polyacrylates, polyacrylonitrile, polyesters, polycarbonates, etc. include rigid connectors, such as spikes, male luers, needleless valve connectors, and rigid couplers. The adhesive formulations of the present disclosure are further adapted to withstand sterilization by heat, chemicals, or radiation (e.g., sterilization with heat, ethylene oxide, or gamma radiation), which is common practice for medical devices, such that the medical device undergoes such sterilization after adhesive bonding of the surfaces.

[0020] The adhesive formulations of the present disclosure may be advantageously used to bond dissimilar materials of medical device components by applying the adhesive onto the surface of one medical component comprised of a non-polar, non-polyvinyl chloride thermoplastic polymeric material, or onto the surface of the other medical component comprised of polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate, or onto both such surfaces, contacting the surfaces with the applied adhesive, and contacting and exposing the contacted surfaces to heat or radiation to crosslink the adhesive and bond the surfaces. Radiation can include (i) photoradiation, such as UV radiation, and (ii) ionizing radiation, such as e-beam and / or gamma radiation.

[0021] In certain embodiments, one medical component can be constructed from a non-polar, non-polyvinyl chloride thermoplastic polymer material and can be medical tubing constructed from a non-polyvinyl chloride thermoplastic polymer material, while in other embodiments, the other medical component can be constructed from polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate and can be a rigid connector or coupler constructed from polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate.

[0022] Exemplary adhesive formulations of the present 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 the polyolefin oligomer chain. Such polyolefin oligomers can be polybutadiene oligomers having reactive acrylate groups, acrylic modified chlorinated polyolefins with or without maleic anhydride functionality. Such reactive polyolefin oligomers can have polar groups that link the reactive acrylate to the olefin, such as polybutadiene acrylate resins having (meth)acrylic groups attached to both ends of the polybutadiene chain via urethane linking groups. Additional reactive groups such as epoxy groups and maleic anhydride residues can also be included in the polyolefin oligomer. The polyolefin oligomers having reactive acrylate groups can have a number average molecular weight of about 500 to about 30,000 g / mol, such as about 500 to about 10,000 or 5,000, or 3,000 g / mol.

[0023] The use of polyolefin oligomers with reactive acrylate groups in the adhesive formulations of the present disclosure has the advantage that the repeating units of the reactive polyolefin are similar to the non-polar thermoplastic polymeric material of one of the medical components that is subjected to bonding, thus providing affinity to the thermoplastic material.In addition, the acrylate and other polar groups on the reactive polyolefin oligomers can create affinity to other medical device components made of polar materials.For example, urethanes or carbamates are strong polar groups that promote surface interaction with the polar surfaces of rigid plastics by dipole-dipole moments or hydrogen bonding.

[0024] Furthermore, the use of oligomers, as opposed to monomeric components, results in less volume shrinkage upon polymerization and minimizes gap-filling volume changes in the bond interface area. This is expected to improve potential leakage of bonded components. Another advantage of the specific polyolefin oligomers with reactive acrylate groups in the adhesive formulations of the present 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 to further cure the adhesive. For example, (meth)acrylate functional end groups and 1,2 vinyl side chains can have crosslinking reactions to produce highly crosslinked networks and form high tensile strength thermosets.

[0025] In one aspect of the present disclosure, the polyolefin oligomer having reactive acrylate groups in the adhesive formulation of the present disclosure comprises a polybutadiene oligomer having reactive acrylate groups 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, for example, 10 to about 100, and m is an integer from 0 to about 250, for example, 0 to about 100. In one embodiment of the present disclosure, the polybutadiene oligomer 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. The acrylate or methacrylate moiety can 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 the present disclosure can include those shown in Scheme 1 below. [ka] Scheme 1

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

[0030] The adhesive formulations of the present disclosure may also include an acrylate monomer component, such as, but not limited to, 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, benzyl acrylate, and the like.

[0031] The adhesive formulation may also include one or more initiators to initiate crosslinking of reactive groups of the polyolefin oligomers having reactive acrylate groups and / or other monomeric components. Useful initiators that may be included in the adhesive formulation of the present disclosure include, for example, thermal initiators and photoinitiators.

[0032] Thermal polymerization initiators are compounds that generate radicals or cations when exposed to heat. For example, azo compounds such as 2,2'-azobis(isobutyronitrile) (AIBN), 2,2'-azodi(2-methylbutyronitrile) (AMBN), 2,2'-azobis(2,4-dimethylvaleronitrile) (ADVN), and benzoyl peroxide (BPO), tert-butyl hydroperoxide (TBHP) thermal radical initiators, organic peroxides such as benzenesulfonic acid esters and alkylsulfonium salts can be used in the adhesive of the present disclosure as thermal initiators.

[0033] The adhesive formulation may also include a photoinitiator that generates free radicals upon irradiation with light, such as ultraviolet radiation, which may also or alternatively be used in the adhesives of the present disclosure, including, for example, but not limited to, ketones available as Darocur 1173, benzophenones, 2-hydroxy-2-methyl-1-phenyl-1-propanone, phosphine oxides such as 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), and the like.

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

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

[0036] According to certain embodiments, the tube for intravenous administration can include non-polyvinyl chloride (PVC) thermoplastic polymers and / or silicone materials. Such materials include, for example, silicone, thermoplastic olefin (TPO), thermoplastic elastomer (TPE), such as styrene-containing thermoplastic elastomer (S-TPE), such as styrene block copolymer (SBC), such as styrene-butadiene-styrene-styrene copolymer (SBS), styrene-butadiene-styrene-styrene block copolymer (SBSS), styrene-isoprene-styrene (SIS), polyolefin elastomer (POE), or other thermoplastic elastomers, or blends containing them. To improve thermo-oxidative and UV stability, the unsaturated rubber block of the S-TPE elastomer (e.g., the polybutadiene or polyisoprene rubber block of the SBS, SBSS, or SIS polymer) can be hydrogenated to form hydrogenated styrenic thermoplastic elastomers, including, but not limited to, styrene-ethylene-butylene-styrene thermoplastic elastomer (SEBS), styrene-ethylene / propylene-styrene (SEPS). High performance thermoplastic elastomers (TPEs) are being designed as sustainable alternatives to flexible PVC for medical tubing and films. Additionally, tubing can include blends of hydrogenated styrenic thermoplastic elastomers with hydrogenated or saturated polyolefins such as polypropylene, e.g. homo, block and / or random polypropylenes such as random copolymer polypropylene (RCPP).

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

[0038] The tube of the present disclosure may have an inner diameter through which fluid flows ranging from about 0.1 mm to about 3.5 mm, for example, from about 0.5 mm to about 2.5 mm, and an overall side wall thickness ranging from 0.1 mm to 2 mm, for example, from about 0.4 mm to about 1 mm.

[0039] The tubing of the present disclosure is particularly useful in conjunction with intravenous assemblies, gravity containers and / or infusion pumps for the transport of intravenous fluids to a patient. The assembly of tubing, valves, fittings and spikes that connects a fluid container intravenously to a patient is sometimes referred to as an "IV set." Infusion pumps are medical devices that can be used to administer intravenous (IV) fluids. Such assemblies, containers and pumps use tubing coupled to one or more medical connectors and tubing of the present disclosure and are useful in their own right.

[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 contacting 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 can be the inner diameter, the outer diameter, or both the inner and outer diameters, depending on whether the contact surfaces being joined are the inner layer, the outer layer, or both. The adhesive can be applied on the inside, the outside, or both.

[0041] Medical connectors that may benefit from the present disclosure include, but are not limited to, connectors constructed from acrylic polymeric materials, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate based materials, polyester, polycarbonate, and the like, or combinations thereof.

[0042] In one embodiment of the present application, a tube according to the present disclosure can be easily mated and bonded to a medical connector by applying an adhesive on the surface of the tube, or on the surface of a medical component such as the medical connector, or on both the surface of the tube and the surface of the medical component. The adhesive-coated surfaces are brought into contact and the contacted surfaces are exposed to heat or radiation to crosslink the adhesive and bond the surfaces together. The bonded medical components can then be sterilized by heat, chemicals, or radiation. In certain embodiments, when the adhesive comprises a polyolefin oligomer with pendant vinyl groups, sterilization by gamma radiation further cures the adhesive to form a stronger bond to the mated surfaces. EXAMPLES

[0043] The following examples are intended to further illustrate certain aspects of the present technology and are not limiting in nature. Those skilled in the art will recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the specific embodiments of the invention described herein.

[0044] A series of adhesive formulations were prepared by combining one of two grades of polybutadiene acrylate resin with (meth)acrylic groups attached to both ends of the 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 below in Scheme 2 and Table 1. TE-2000 [ka] TEAI-1000 [ka] Scheme 2 [Table 1]

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

[0046] Sample 1: A laboratory study was conducted to develop a formulation containing TE2000 dissolved in methyl ether ketone (MEK) to produce a solution of 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 to produce a solution of uniform viscosity at 50% w / w concentration.

[0048] Sample 3: To 7 g of 50% TE-2000 from sample 1 (3.5 g of TE-2000), 0.1 g of photoinitiator Irgacure 819 was added to give a weight ratio of TE-2000 to Irgacure 819 of 70:2.

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

[0050] Sample 5: To 7g of 50% TE-2000 from Sample 1 (3.5g TE-2000), 1.5g Isobornyl acrylate (IBOA), 0.1g Irgacure 819 were added to make 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 TE-2000) from Sample 2, 1.5 g IBOA, 0.1 g Irgacure 819 were added to make a solution of TEAI-1000, IBOA and Irgacure 819 in a weight ratio of 70:30:2.

[0052] Joining assemblies and processing styrenic TPE tubing into female pocket luer connectors:

[0053] Extruded styrenic block copolymer-based TPE tubing with dimensions of 0.107" ID and 0.145" OD was cut into 3" lengths each, then a thin layer of adhesive coating was applied by cotton Q-tip to the outer surface of the tube in a range of approximately 0.5" length. The adhesive was from Samples 1-6 prepared above. The adhesive-covered tubing segment was manually fully inserted into the female pocket of the Luer connect (mABS material) until it stopped and firmly engaged. The assembly was then UV cured for 20 seconds using a 365 nm wavelength LED. The UV power was 1-1.5 W / cm. 2 and the cure distance between the LED head and the assembly joint was 1 inch. The assembly was also sterilized with gamma radiation to test the effectiveness from gamma radiation with doses of 21.4 to 35 kGy.

[0054] Bonded Assembly Separation Force Measurements by Instron:

[0055] Tensile force testing was performed at a strain rate of 20 in / min using a generic tester (Instron). The luer connector was placed in the holding fixture and then the upper gripper was adjusted so that it clamped onto the tubing 1 inch away from the opening of the binding pocket.

[0056] Tensile force results (sample size 5) from a set of samples at different processing conditions (UV, gamma) are shown in Table 2 below along with failure modes (TPO=tube pullout, TB=tubing break). [Table 2]

[0057] The adhesive compositions of Samples 1 and 2 include polybutadiene with acrylate reactive groups and the solvent MEK. Although no UV or thermal initiators are present in the adhesive compositions, the tensile strength was observed to increase by 25% for Sample 1 and 18% for Sample 2 after UV and gamma treatment (Figure 1A). Figure 2 shows the minitab results of the statistical improvement after UV / gamma sterilization.

[0058] The tensile force data in Table 2 from Adhesive Sample 3, Sample 4, Sample 5 and Sample 6 were collected and the increasing percentage change in tensile force from each processing condition tabulated in Table 3 was plotted in Figure 3 for comparison under different processing conditions. [Table 3]

[0059] Additionally, to understand if the changes in tensile force were statistically significant upon treatment, an ANOVA analysis was performed using graph plots and Tukey's comparison test was demonstrated below for samples 3-6. The analysis showed that treatment (Gamma, UV, or a combination of UV and Gamma) was required to improve tensile force from the control, which was statistically significant for samples 3-6.

[0060] In addition to the ingredients listed for the samples, 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 include tackifiers. Additionally, free radical inhibitors such as HQ, BHT, MEHQ, etc. may be added to extend the shelf life of the thermal or photocurable adhesive formulation.

[0061] It is understood that any particular order or hierarchy of blocks in the disclosed process methods is illustrative of an example approach. Based on design or implementation preferences, it is understood that the particular order or hierarchy of blocks in the processes may be rearranged, or all of the illustrated blocks may be performed. In some implementations, any of the blocks may be performed simultaneously.

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

[0063] Reference to a singular element does not mean "one and only one" unless otherwise specified, but rather "one or more." The term "several" refers to one or more, unless otherwise specified. Masculine pronouns (e.g., his) include the feminine and neuter genders (e.g., her and its), and vice versa. Headings and subheadings, if any, are used for convenience only and are not intended to limit the invention.

[0064] The term "exemplary" is used herein to mean "serving as an example or illustration." Any aspect or design described herein as "exemplary" is not necessarily to be construed as preferred or advantageous over other aspects or designs. In an aspect, various alternative configurations and operations described herein may be considered at least equivalent.

[0065] As used herein, the phrase "at least one" before a series of items, together with the term "or" to separate any of the items, modifies the entire list, not each item in the list. The phrase "at least one" does not require the selection of at least one of the items. Rather, the phrase allows for a meaning 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. By way of example, the phrase "at least one of A, B, or C" may refer to only A, only B, or only C; or any combination of A, B, and C.

[0066] A phrase such as "aspect" does not mean that such aspect is essential to the technology or that such aspect applies to all configurations of the technology. Disclosure regarding an aspect may apply to all configurations or to one or more configurations. An aspect may provide one or more examples. A phrase such as an aspect may refer to one or more aspects, and vice versa. A phrase such as "aspect" does not mean that such aspect is essential to the technology or that such aspect applies to all configurations of the technology. Disclosure regarding an embodiment may apply to all embodiments, or to one or more embodiments. An aspect may provide one or more examples. A phrase such as an aspect may refer to one or more aspects, and vice versa. A phrase such as "aspect" does not mean that such aspect is essential to the technology or that such aspect applies to all configurations of the technology. Disclosure regarding a configuration may apply to all configurations or to one or more configurations. A configuration may provide one or more examples. A phrase such as a configuration may refer to one or more configurations, and vice versa.

[0067] In one aspect, unless otherwise specified, all measurements, values, ratings, positions, dimensions, sizes, and other specifications set forth in this specification, including the following claims, are approximate and not exact, and are intended in one aspect to have a reasonable range consistent with the function to which they relate and that which is customary in the art to which they pertain.

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

[0069] All structural and functional equivalents to the elements of the various aspects described throughout this disclosure that are known or that later become known to those skilled in the art are intended to be expressly incorporated herein by reference and encompassed by the claims. Moreover, nothing disclosed herein is intended to be dedicated to the public, regardless of whether such disclosure is expressly recited in the claims. No element of a claim is to be construed under the provisions of 35 USC § 112(f) unless the element is expressly recited using the phrase "means for" or, in the case of a method claim, unless the element is recited using the phrase "step for". Moreover, to the extent that terms such as "include", "have", and the like are used, such terms are intended to be inclusive in the same manner as the term "comprise" is interpreted when "comprise" is used as a transitional term in the claims.

[0070] The title, background, summary, brief description of the drawings and abstract of this disclosure are hereby incorporated into this disclosure and are provided as illustrative examples of this disclosure, not as a limiting description. They are submitted with the understanding that they will not be used to limit the scope or meaning of the claims. Furthermore, in the detailed description, it will be seen that the description provides illustrative examples, and that various features have been grouped together in various embodiments for the purpose of streamlining the disclosure. This method of disclosure should not be interpreted as reflecting an intention that the claimed subject matter requires more features than are expressly recited in each claim. Rather, as the following claims reflect, the inventive subject matter lies in less than all features of a single disclosed structure or operation. The following claims are incorporated into the detailed description, with each claim standing on its own as separately claimed subject matter.

[0071] The claims are not intended to be limited to the embodiments described herein, but are to be accorded the full scope consistent with the language of the claims, including all legal equivalents. Nonetheless, none of the claims are intended, and should not be construed, to cover subject matter that does not meet the requirements of 35 USC §§ 101, 102, or 103.

Claims

1. 1. A method for bonding dissimilar materials of medical device components, comprising: The method comprises: applying an adhesive onto a surface of one medical component comprised of a non-polar, non-polyvinyl chloride thermoplastic polymeric material, or onto a surface of the other medical component comprised of polyacrylate, polyacrylonitrile, polyester, and / or polycarbonate, or onto both such surfaces; contacting the surface; exposing the contacted surfaces to heat or light radiation to crosslink the adhesive and bond the surfaces; sterilizing the bonded surfaces; and Including, The adhesive formulation comprises: (a) a polyolefin oligomer having reactive acrylate and alkenyl groups; (b) an initiator; and optionally (c) a solvent; The polyolefin oligomer is represented by the formula (I): 【Chemistry 1】 (In the formula, R １ represents an acrylate or methacrylate moiety attached to the polyolefin chain via a urethane bond, n is an integer from 10 to 500, and m is an integer from 0 to 250. The method is represented by

2. The method of claim 1 further comprising subjecting the bonded surfaces to sterilization by ionizing radiation.

3. The method of claim 1 , wherein the one medical component is a medical tubing.

4. The method of claim 3 , wherein the tube comprises a styrene-containing thermoplastic elastomer.

5. 10. The method of claim 1, wherein the other medical components include medical connectors comprised of acrylic polymers, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), acrylic-polycarbonate based materials, polyester, polycarbonate, or combinations thereof.

6. 10. The method of claim 1, wherein the one medical component comprises a medical tubing comprised of a styrene-containing thermoplastic elastomer and the other medical component is a medical connector comprised of an acrylic-based polymer, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), an acrylic-polycarbonate based material, polyester, polycarbonate, or a combination thereof.

7. The method of claim 1 , wherein the initiator comprises a photoinitiator.

8. The method of claim 1 , wherein the adhesive formulation comprises a solvent.

9. 9. The method of any one of claims 1 to 8, wherein the polyolefin oligomer having reactive acrylate groups comprises the polybutadiene oligomer having reactive acrylate end groups attached to the polybutadiene oligomer via carbamate linkages and pendant 1,2 vinyl groups along the polybutadiene oligomer chain.

10. 1. An adhesive formulation for bonding together polyvinyl chloride free materials comprising: (a) a polyolefin oligomer having reactive acrylate end groups and pendant 1,2 vinyl groups along the polyolefin oligomer chain; (b) an initiator; and optionally (c) a solvent, The polyolefin oligomer having reactive acrylate groups is represented by the formula (I): 【Chemistry 2】 (In the formula, R １ represents an acrylate or methacrylate moiety attached to the polyolefin chain via a urethane bond, n is an integer from 10 to 500, and m is an integer from 0 to 250.

1. An adhesive formulation comprising a polybutadiene oligomer having reactive acrylate groups represented by:

11. The adhesive formulation of claim 10 , wherein the initiator comprises a photoinitiator.

12. 11. The adhesive formulation of claim 10, wherein said polyolefin oligomer comprises at least 50% by weight of said reactive component of said adhesive formulation.

13. 13. An infusion set comprising tubing constructed of a non-polar, polyvinyl chloride-free thermoplastic polymeric material bonded to a medical connector by a cured adhesive formulation according to any one of claims 10 to 12.

14. 14. The infusion set of claim 13, wherein the tubing comprises a styrene-containing thermoplastic elastomer and the medical connector is constructed from an acrylic polymer, polyacrylonitrile, acrylonitrile-butadiene-styrene (ABS), methyl methacrylate-acrylonitrile-butadiene-styrene (mABS), an acrylic-polycarbonate based material, polyester, polycarbonate, or a combination thereof.

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