Caps that do not contain polyfluoroalkyl substances

Abstract

The present disclosure provides a liner comprising a septum and a layer, wherein the layer comprises a thermoplastic polymer, the septum comprises an elastomer, and the septum is bonded to the layer comprising the thermoplastic polymer. The present disclosure also provides a cap assembly comprising the liner disclosed herein and a cap, wherein the cap is bonded to the liner. Further, the present disclosure provides a cap and vial assembly comprising the cap assembly disclosed herein and a vial, wherein the cap assembly is bonded to the vial. The present disclosure also provides a method of testing the water quality of a sample using an analytical instrument, wherein the sample is contained within a container comprising the liner disclosed herein, the cap assembly disclosed herein, or the cap and vial assembly disclosed herein, and the method comprises passing a syringe through the liner to remove a portion of the sample and testing the portion of the sample using an analytical instrument.

Description

Technical Field

[0001] Priority Information This application claims priority to U.S. Provisional Patent Application No. 63 / 389,440, filed on July 15, 2022, entitled "Polyfluoroalkyl Substance Free Caps", the disclosure of which is incorporated herein by reference.

Background Art

[0002] Perfluoroalkyl and polyfluoroalkyl substances (PFAS) are artificial chemicals developed in the 1940s. PFAS have been used for many years in a variety of industries ranging from the aerospace and military industries to consumer products such as clothing, food packaging, and non-stick cookware. Due to their widespread use, many individuals around the world are exposed to PFAS throughout their lives.

[0003] PFAS spread rapidly through the environment and ultimately spread into soil, water, and air, and then into agricultural products, livestock, and animal by-products for human consumption. These chemicals, including perfluorooctanoic acid (PFOA) and perfluorooctane sulfonic acid (PFOS), are considered "forever chemicals" because they do not break down in the environment and can remain in the human body indefinitely. There are several types of PFAS with various levels of toxicity and adverse effects that have been little studied.

[0004] Certain PFAS can be dangerous even at very low levels and can affect humans adversely as follows. - Decreased birth rate - High blood pressure in pregnant women, - Increased risk of obesity and high cholesterol, - Increased risk of cancer, - Liver disease, - Delayed child development, - Weakened immunity, - Thyroid problems, and - Hormonal changes.

[0005] To address the challenges posed by PFAS to humans, current and future PFAS testing will be essential.

[0006] Chromatography and mass spectrometry, methods for separating and identifying the components of a mixture, can be used for PFAS testing. PFAS testing is growing rapidly in the field of chromatography testing by the newly approved U.S. Environmental Protection Agency (EPA) test methods, as well as by a number of developing test methods.

[0007] The closures commonly used on chromatography vials are open-top caps through which a syringe can penetrate and have a liner containing polytetrafluoroethylene (PTFE). PTFE is used in chromatography because it is inert and chemically compatible with a wide variety of common laboratory chemicals and solvents. However, these standard chromatography caps made of PTFE, a common PFAS, are not suitable for any PFAS testing.

[0008] When conducting water quality tests for PFAS to prevent contamination of PTFE samples, polypropylene caps have been used, but polypropylene caps cannot be resealed. Therefore, multiple penetrations and / or injections from the same vial are not possible (Shoemaker, J.A. and Tettenhorst, D.R., Method 537.1: Determination of Selected Per- and Polyfluorinated Alkyl Substances in Drinking Water by Solid Phase Extraction and Liquid Chromatography / Tandem Mass Spectrometry (LC / MS / MS), EPA Document #: EPA / 600 / R-18 / 352, Version 1.0, November 2018). Further, since polypropylene caps cannot be resealed when a portion of the sample is removed from the vial by penetration, the sample evaporates, decomposes, and / or becomes contaminated, and the vial containing the sample cannot be stored for future tests. Therefore, when additional tests are to be performed, multiple vials containing the sample are required, and potentially, an individual needs to return to the site to collect additional samples.

[0009] The products and methods disclosed herein address these and other needs.

Summary of the Invention

[0010] According to the objectives of the disclosed products and methods, as embodied and broadly described herein, the disclosed subject matter, in one aspect, relates to a liner, a cap assembly, and a cap and vial assembly, and methods of using the same.

[0011] For example, as disclosed herein, there is provided a liner comprising a septum and a layer comprising a thermoplastic polymer, wherein the septum comprises an elastomer and the septum is bonded to the layer comprising the thermoplastic polymer.

[0012] In a further example, there is provided a cap assembly comprising a liner disclosed herein and a cap, the cap being coupled to the liner.

[0013] Additionally, there is provided a cap and vial assembly comprising a cap assembly disclosed herein and a vial, the cap assembly being coupled to the vial.

[0014] Further, herein also disclosed is a method of testing the water quality in a sample using an analytical instrument, the sample being contained within a container comprising a liner disclosed herein, a cap assembly disclosed herein, or a cap and vial assembly disclosed herein, the method comprising passing a syringe through the liner to remove a portion of the sample and testing a portion of the sample using an analytical instrument.

[0015] Additional advantages will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the aspects described below. The advantages described below will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are not restrictive.

[0016] Details of one or more embodiments of the invention are set forth in the accompanying drawings and the description below. Other features, objects, and advantages of the invention will be apparent from the description, the drawings, and the appended claims.

Brief Description of the Drawings

[0017] The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate several aspects of the disclosure and together with the description serve to explain the principles of the disclosure.

[0018]

Fig. 1A-1B

Fig. 2A-2B

Fig. 3

Fig. 4A-4C

Fig. 5A-5B

Fig. 6A-6C

Fig. 7A-7C

Fig. 8A-8B

Fig. 9A-9C

[0019] The following description of the disclosure is provided as an enabling teaching of the disclosure in its best presently known embodiments. Many modifications and other embodiments will come to the mind of one skilled in the art to which the disclosed products and methods relate, having the benefit of the teachings presented in the above description and the related drawings. Therefore, it is to be understood that the disclosure is not to be limited to the specific embodiments disclosed and that modifications and other embodiments are intended to be included within the scope of the appended claims. One skilled in the art will recognize many variations and adaptations of the aspects described herein. These variations and adaptations are intended to be included within the teachings of the disclosure and are intended to be encompassed by the claims of this specification.

[0020] Although certain terms are employed in this specification, they are used only in a general and illustrative sense and are not intended for purposes of limitation.

[0021] As will be apparent to those skilled in the art upon reading this disclosure, each of the individual embodiments described and illustrated herein has separate components and features that can be readily separated from, or combined with, the features of any of several other embodiments, without departing from the scope or spirit of the present disclosure.

[0022] Any of the described methods can be performed in the order of the described events or in any other order that is theoretically possible. That is, unless expressly stated otherwise, it is in no way intended that any method or aspect described herein be construed as requiring that its steps be performed in a particular order. Accordingly, where a method claim does not specifically recite steps in a particular order in the claim or description, no order should be inferred in any respect. This applies to any possible non-explicit basis for interpretation, including logical issues regarding the structure of steps or the flow of operations, the plain meaning derived from grammar or punctuation, or the number or type of aspects described in the specification.

[0023] All publications mentioned in this specification are hereby incorporated by reference herein for the purpose of disclosing and describing the methods and / or products to which the publications are cited. The publications discussed in this specification are provided solely for their disclosure prior to the filing date of the present application. It should not be construed that the present invention admits a right prior to such publications by virtue of prior invention. Further, the publication dates provided herein may be different from the actual publication dates and may require independent verification.

[0024] Also, it should be understood that the terms used in this specification are for the purpose of describing particular embodiments only and are not intended to be limiting. Unless otherwise defined, all technical and scientific terms used in this specification shall have the same meaning as commonly understood by one of ordinary skill in the art to which the disclosed products and methods pertain. Terms defined as in a commonly used dictionary shall be interpreted to have a meaning that coincides with their meaning in the context of the specification and the relevant art, and it can be further understood that they should not be interpreted in an idealized or overly formal sense unless explicitly defined in this specification.

[0025] Before describing various aspects of the present disclosure, the following definitions are provided and should be used unless otherwise indicated. Additional terms may be defined elsewhere in the present disclosure.

[0026] Definitions In this specification and the following claims, many terms are referenced and are defined to have the following meanings.

[0027] As used herein, the term "comprising" should be interpreted as specifying the presence of the referenced feature, element, step, or component, but not precluding the presence or addition of one or more other features, elements, steps, or components, or groups thereof. Further, each of the terms "by", "comprising", "comprised of", "including", "includes", "included", "involving", "involves", "involved", and "such as" is used in an open and non-limiting sense and may be used interchangeably. Further, the term "comprising" is intended to include examples and aspects subsumed by "consisting essentially of" and "consisting of". Similarly, the term "consisting essentially of" is intended to include examples subsumed by the term "consisting of".

[0028] As used in this specification and the appended claims, the singular forms "a", "an", and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, references to "a compound", "a composition", or "a disease" include two or more such compounds, compositions, or diseases, etc., but are not limited thereto.

[0029] It should be noted that ratios, concentrations, amounts, and other numerical data may be expressed herein in range format. It can be further understood that each endpoint of a range is important both in relation to the other endpoint and independently of the other endpoint.

[0030] When ranges are expressed, further aspects include from one particular value and / or up to and including another particular value. For example, if the indicated range includes one or both of the limits, ranges excluding one or both of such included limits are also included in the present disclosure. For example, the phrase "x to y" includes the range from "x" to "y", as well as ranges greater than "x" and less than "y". A range may also be expressed as an upper limit. For example, "about x, y, z or less" should be interpreted to include the specific ranges of "about x", "about y", and "about z", as well as ranges less than "x", less than "y", and less than "z". Similarly, the phrase "about x, y, z or more" should be interpreted to include the specific ranges of "about x", "about y", and "about z", as well as ranges greater than "x", greater than "y", and greater than "z". In addition, when "x" and "y" are numerical values, the phrase "about 'x' to 'y'" includes "about 'x' to about 'y'".

[0031] Such range formats are used for convenience and brevity and should therefore be interpreted flexibly to include not only the numerical values explicitly recited as the limits of the range, but also all individual numerical values or sub-ranges subsumed within that range as if each were explicitly recited. By way of illustration, the numerical range "about 0.1% to 5%" should be interpreted to include not only the explicitly recited values of about 0.1% to about 5%, but also the individual values (e.g., about 1%, about 2%, about 3%, and about 4%) and sub-ranges (e.g., about 0.5% to about 1.1%, about 5% to about 2.4%, about 0.5% to about 3.2%, and about 0.5% to about 4.4%, and other possible sub-ranges) subsumed within the indicated range.

[0032] There are several values disclosed in this specification, and each value, in addition to the value itself, is understood to be disclosed in this specification as "about" that particular value. For example, if the value "10" is disclosed, "about 10" is also disclosed. In this specification, a range can be expressed as from "about" a particular value and / or to "about" another particular value. Similarly, when a value is expressed as an approximation, it can be understood that the use of the antecedent "about" forms a further aspect of the particular value. For example, if the value "about 10" is disclosed, "10" is also disclosed.

[0033] As used herein, the terms "about," "approximately," "or about," and "substantially" mean that the quantity or value in question can be the exact value or a value that provides equivalent results or effects to those recited in the claims or taught in this specification. That is, the quantities, sizes, formulations, parameters, and other quantities and characteristics are not and need not be exact, but may be approximate and / or larger or smaller, as desired, so long as equivalent results and effects are obtained, reflecting tolerances, conversion factors, rounding, measurement errors, and the like, and other factors known to those of ordinary skill in the art. In some situations, the value providing equivalent results or effects may not be reasonably determinable. In such cases, as used herein, "about" and "or about" generally mean a nominal value that indicates a variation of ±10% unless otherwise indicated or inferred. Generally, a quantity, size, formulation, parameter, or other quantity or characteristic is "about," "approximately," or "or about," whether or not so expressly indicated. It is understood that when "about," "approximately," or "or about" is used before a quantitative value, the parameter includes the particular quantitative value itself as well, unless otherwise specifically indicated.

[0034] As used herein, the term "substantially free of" when used in the context of a product or a component of a product that is substantially absent, is intended to refer to an amount of less than about 70 parts per trillion, such as less than about 50 parts per trillion, less than about 40 parts per trillion, less than about 25 parts per trillion, or less than about 10 parts per trillion.

[0035] As used herein, "cross-sectional shape" refers to the shape of a plane that is substantially perpendicular to the thickness, and "thickness" refers to the average dimension between opposing surfaces of an object.

[0036] As used herein, the term "characteristic dimension" refers to the longest straight-line distance between two points within the plane of the cross-sectional shape. In this specification, the plane of the cross-sectional shape can be, for example, the plane of a liner or a cap. "Average characteristic dimension" generally refers to a statistical average characteristic dimension. For example, if a liner or a cap has a cross-sectional shape that is substantially circular, the average characteristic dimension can refer to the average diameter.

[0037] The term "(co)polymer" includes homopolymers, copolymers, or mixtures thereof.

[0038] As used herein, "molecular weight" refers to the number-average molecular weight measured by 1 1H NMR spectroscopy, unless otherwise explicitly indicated.

[0039] Chemical definition Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.

[0040] The organic moieties referred to when defining variable positions within general formulas described herein (e.g., the term "halogen") are a general term for the individual substituents encompassed by that organic moiety. The prefix C n ~C mIn each case, it indicates the possible number of carbon atoms in the following groups or moieties.

[0041] As used herein, the term "ion" refers to a charge (positive, negative, or both simultaneously contained within a single molecule, molecular cluster, molecular complex, or moiety (e.g., zwitterion)), or any molecule, part of a molecule, molecular cluster, molecular complex, moiety, or atom that can be made to contain a charge. Methods for imparting a charge to a molecule, part of a molecule, molecular cluster, molecular complex, moiety, or atom are disclosed herein and can also be achieved by methods known in the art, such as protonation, deprotonation, oxidation, reduction, alkylation, acetylation, esterification, de-esterification, hydrolysis, and the like.

[0042] The term "anion" is a type of ion and is included within the meaning of the term "ion". An "anion" is any molecule, part of a molecule (e.g., zwitterion), molecular cluster, molecular complex, moiety, or atom that contains a net negative charge or can be made to contain a net negative charge. As used herein, the term "anion precursor" is used to specifically refer to a molecule that can be converted to an anion via a chemical reaction (e.g., deprotonation).

[0043] The term "cation" is a type of ion and is included within the meaning of the term "ion". A "cation" is any molecule, part of a molecule (e.g., zwitterion), molecular cluster, molecular complex, moiety, or atom that contains a net positive charge or can be made to contain a net positive charge. As used herein, the term "cation precursor" is used to specifically refer to a molecule that can be converted to a cation via a chemical reaction (e.g., protonation or alkylation).

[0044] As used herein, the term "substituted" is contemplated to include all acceptable substituents of an organic compound. In a broad aspect, acceptable substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and non-aromatic substituents of an organic compound. Exemplary substituents include, for example, those described below. Acceptable substituents can be one or more, and can be the same or different with respect to a suitable organic compound. For the purposes of the present disclosure, a heteroatom such as nitrogen can have any acceptable substituent of the organic compounds described herein that satisfies the valence of the hydrogen substituent and / or the heteroatom. The present disclosure is not intended to be limited in any way by the acceptable substituents of the organic compounds. Also, the terms "substituted" or "substituted with" include the implicit conditions that such substitution follows the acceptable valences of the substituting atom and the substituent, and that the substitution results in a stable compound, i.e., a compound that does not undergo spontaneous conversion by rearrangement, cyclization, elimination, etc.

[0045] As used herein, "Z 1 ", "Z 2 ", "Z 3 ", and "Z 4 " are used as general symbols to represent various specific substituents. These symbols can be any substituent not limited to those disclosed herein, and can be defined as a specific substituent in one instance and as several other substituents in another instance.

[0046] As used herein, the term "aliphatic" refers to non-aromatic hydrocarbon groups and includes branched and unbranched, alkyl, alkenyl, or alkynyl groups.

[0047] As used herein, the term "alkyl" refers to a saturated, straight-chain, or branched saturated hydrocarbon moiety. Unless otherwise specified, C1-C 24 (e.g., C1-C 22 , C1-C 20 , C1-C 18 , C1-C 16 , C1-C14 , C1-C 12 , C1-C 10 , C1-C8, C1-C6, or C1-C4) alkyl groups are contemplated. Examples of alkyl groups include methyl, ethyl, propyl, 1-methyl-ethyl, butyl, 1-methyl-propyl, 2-methyl-propyl, 1,1-dimethyl-ethyl, pentyl, 1-methyl-butyl, 2-methyl-butyl, 3-methyl-butyl, 2,2-dimethyl-propyl, 1-ethyl-propyl, hexyl, 1,1-dimethyl-propyl, 1,2-dimethyl-propyl, 1-methyl-pentyl, 2-methyl-pentyl, 3-methyl-pentyl, 4-methyl-pentyl, 1,1-dimethyl-butyl, 1,2-dimethyl-butyl, 1,3-dimethyl-butyl, 2,2-dimethyl-butyl, 2,3-dimethyl-butyl, 3,3-dimethyl-butyl, 1-ethyl-butyl, 2-ethyl-butyl, 1,1,2-trimethyl-propyl, 1,2,2-trimethyl-propyl, 1-ethyl-1-methyl-propyl, 1-ethyl-2-methyl-propyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like. The alkyl substituent can be unsubstituted or substituted with one or more chemical moieties. The alkyl group can be substituted with one or more groups including, but not limited to, hydroxyl, halogen, acetal, acyl, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, aldehyde, amino, cyano, carboxylic acid, ester, ether, carbonate, carbamate, ketone, nitro, phosphonyl, silyl, sulfoxo, sulfonyl, sulfone, sulfoxide, or thiol, provided that the substituents are sterically compatible and the laws of chemical bonding and strain energy are satisfied, as described below.

[0048] Throughout this specification, the term "alkyl" is generally used to refer to both unsubstituted alkyl groups and substituted alkyl groups. However, in this specification, substituted alkyl groups are also specifically referred to by identifying specific substituents on the alkyl group. For example, the term "halogenated alkyl" or "haloalkyl" specifically refers to an alkyl group substituted with one or more halides (halogens: e.g., fluorine, chlorine, bromine, or iodine). The term "alkoxyalkyl" specifically refers to an alkyl group substituted with one or more alkoxy groups, as described below. The term "alkylamino" specifically refers to an alkyl group substituted with one or more amino groups, as described below. When the term "alkyl" is used in one instance and a specific term such as "alkyl alcohol" is used in another instance, the term "alkyl" does not mean to refer to specific terms such as "alkyl alcohol".

[0049] This convention is also used for other groups described in this specification. That is, terms such as "cycloalkyl" refer to both unsubstituted and substituted cycloalkyl moieties, but the substituted moieties can additionally be specifically identified in this specification. For example, a specific substituted cycloalkyl can be referred to as, for example, "alkylcycloalkyl". Similarly, substituted alkoxy can specifically be referred to as, for example, "halogenated alkoxy", and a specific substituted alkenyl can be, for example, "alkenyl alcohol", etc. Again, the convention of using general terms such as "cycloalkyl" and specific terms such as "alkylcycloalkyl" does not imply that the general term does not include the specific term.

[0050] As used herein, the term "alkenyl" refers to an unsaturated, straight-chain, or branched hydrocarbon moiety containing a double bond. Unless otherwise specified, C2-C 24 (e.g., C2-C 22 , C2-C 20 , C2-C 18 , C2-C 16 , C2-C 14 , C2-C12 , C2~C 10, (C2-C8, C2-C6, or C2-C4) alkenyl groups are contemplated. The alkenyl group may contain more than one unsaturated bond.Examples include ethenyl, 1-propenyl, 2-propenyl, 1-methyltenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl.The term "vinyl" refers to a group having the structure -CH=CH2, 1-propenyl refers to a group having the structure -CH=CH-CH3, and 2-propenyl refers to a group having the structure -CH2-CH=CH2. (Z. 1 Z 2 )C=C(Z 3 Z 4 ) Asymmetric structures such as are intended to include both E and Z isomers. This can be inferred from the structural formulas in this specification where asymmetric alkenes are present, or it can be explicitly indicated by the bond symbol C=C. The alkenyl substituent can be unsubstituted or substituted by one or more chemical moieties. Examples of suitable substituents are, as described below, provided that the substituent is sterically compatible and the laws of chemical bonding and strain energy are satisfied, for example, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acetal, acyl, aldehyde, amino, cyano, carboxylic acid, ester, ether, carbonate, carbamate, halide, hydroxyl, ketone, nitro, phosphonyl, silyl, sulfooxo, sulfonyl, sulfone, sulfoxide, or thiol.

[0051] As used herein, the term "alkynyl" represents a straight or branched hydrocarbon moiety containing a triple bond. Unless otherwise specified, C2-C 24 (e.g., C2-C 24 , C2-C 20 , C2-C 18 , C2-C 16 , C2-C 14 , C2-C 12 , C2-C 10, a (C2-C8, C2-C6, or C2-C4) alkynyl group is contemplated. The alkynyl group may contain more than one unsaturated bond. Examples include C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2-pentynyl, 4-methyl-2-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl. The alkynyl substituent may be unsubstituted or substituted by one or more chemical moieties. Examples of suitable substituents include, as described below, for example, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acetal, acyl, aldehyde, amino, cyano, carboxylic acid, ester, ether, carbonate ester, carbamate ester, halide, hydroxyl, ketone, nitro, phosphonyl, silyl, sulfoxo, sulfonyl, sulfone, sulfoxide, or thiol.

[0052] As used herein, the term "aryl" and terms for derivatives such as aryloxy refer to groups containing a monovalent aromatic carbocyclic group of 3 to 50 carbon atoms. The aryl group may contain a single ring or multiple fused rings. In some embodiments, the aryl group is C6-C 10It contains an aryl group. Examples of aryl groups include, but are not limited to, benzene, phenyl, biphenyl, naphthyl, tetrahydronaphthyl, phenylcyclopropyl, phenoxybenzene, and indanyl. The term "aryl" also includes "heteroaryl", which is defined as a group containing an aromatic group having at least one heteroatom incorporated within the ring of the aromatic group. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorus. The term "non-heteroaryl", which is also included in the term "aryl", defines a group containing an aromatic group that does not contain a heteroatom. The aryl substituent can be unsubstituted or substituted by one or more chemical moieties. Examples of suitable substituents include, as described herein, for example, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acetal, acyl, aldehyde, amino, cyano, carboxylic acid, ester, ether, carbonate ester, carbamate ester, halide, hydroxyl, ketone, nitro, phosphonyl, silyl, sulfooxo, sulfonyl, sulfone, sulfoxide, or thiol. The term "biaryl" is a particular type of aryl group and is included in the definition of aryl. A biaryl refers to two aryl groups that are joined together via a fused ring structure such as naphthalene or via one or more carbon-carbon bonds such as biphenyl.

[0053] As used herein, the term "cycloalkyl" refers to a non-aromatic carbon-based ring consisting of at least 3 carbon atoms. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The term "heterocycloalkyl" refers to a cycloalkyl group as defined above, wherein at least one of the carbon atoms of the ring is substituted by a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. Cycloalkyl groups and heterocycloalkyl groups can be substituted or unsubstituted. Cycloalkyl groups and heterocycloalkyl groups can be substituted by one or more groups including, but not limited to, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acetal, acyl, aldehyde, amino, cyano, carboxylic acid, ester, ether, carbonate, carbamate, halide, hydroxyl, ketone, nitro, phosphonyl, silyl, sulfoxo, sulfonyl, sulfone, sulfoxide, or thiol as described herein.

[0054] As used herein, the term "cycloalkenyl" refers to a non-aromatic carbon-based ring consisting of at least 3 carbon atoms and containing at least one double bond, i.e., C=C. Examples of cycloalkenyl groups include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, and the like. The term "heterocycloalkenyl" is a type of cycloalkenyl group as defined above, is included within the meaning of the term "cycloalkenyl", and at least one of the carbon atoms of the ring is substituted by a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. The cycloalkenyl group and the heterocycloalkenyl group can be substituted or unsubstituted. The cycloalkenyl group and the heterocycloalkenyl group can be substituted by one or more groups including, but not limited to, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acetal, acyl, aldehyde, amino, cyano, carboxylic acid, ester, ether, carbonate, carbamate, halide, hydroxyl, ketone, nitro, phosphonyl, silyl, sulfooxo, sulfonyl, sulfone, sulfoxide, or thiol as described herein.

[0055] As used herein, the term "cyclic group" is used to refer to either, or both, an aryl group, a non-aryl group (i.e., a cycloalkyl, heterocycloalkyl, cycloalkenyl, and heterocycloalkenyl group). A cyclic group has one or more ring systems (e.g., monocyclic, bicyclic, tricyclic, polycyclic, etc.) which can be substituted or unsubstituted. A cyclic group can contain one or more aryl groups, one or more non-aryl groups, or one or more aryl groups and one or more non-aryl groups.

[0056] As used herein, the term "acyl" refers to the formula -C(O)Z 1 represented by the formula, wherein Z 1may be a hydrogen, hydroxyl, alkoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group as described above. As used herein, the term "acyl" may be used interchangeably with "carbonyl". Throughout this specification, "C(O)" or "CO" is a shorthand notation for C=O.

[0057] As used herein, the term "acetal" refers to the formula (Z 1 Z 2 )C(=OZ 3 )(=OZ 4 ), wherein Z 1 , Z 2 , Z 3 , and Z 4 are each independently a hydrogen, halogen, hydroxyl, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group as described above.

[0058] As used herein, the term "alkanol" refers to the chemical formula Z 1 OH, wherein Z 1 is an alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group as described above.

[0059] As used herein, the term "alkoxy" as used herein is an alkyl group attached through a single terminal ether bond, i.e., as defined above, an "alkoxy" group can be defined as a group of the formula Z 1 -O-, wherein Z 1 is unsubstituted or substituted alkyl. Unless otherwise specified, Z 1 is C1-C 24 (e.g., C1-C 22 , C1-C 20 , C1-C 18 , C1-C 16, C1 to C 14 , C1 to C 12 , C1 to C 10 , an alkoxy group that is a C1 to C8, C1 to C6, or C1 to C4 alkyl group is contemplated. Examples include methoxy, ethoxy, propoxy, 1-methyl-ethoxy, butoxy, 1-methyl-propoxy, 2-methyl-propoxy, 1,1-dimethyl-ethoxy, pentoxy, 1-methyl-butoxy, 2-methyl-butoxy, 3-methyl-butoxy, 2,2-di-methyl-propoxy, 1-ethyl-propoxy, hexoxy, 1,1-dimethyl-propoxy, 1,2-dimethyl-propoxy, 1-methyl-pentoxy, 2-methyl-pentoxy, 3-methyl-pentoxy, 4-methyl-penoxy, 1,1-dimethyl-butoxy, 1,2-dimethyl-butoxy, 1,3-dimethyl-butoxy, 2,2-dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-dimethyl-butoxy, 1-ethyl-butoxy, 2-ethylbutoxy, 1,1,2-trimethyl-propoxy, 1,2,2-trimethyl-propoxy, 1-ethyl-1-methyl-propoxy, and 1-ethyl-2-methyl-propoxy.

[0060] As used herein, the term "aldehyde" is represented by the formula -C(O)H. Throughout this specification, "C(O)" is a shorthand notation for C=O.

[0061] As used herein, the term "amine" or "amino" is represented by the formula -NZ 1 Z 2 Z 3 and in the formula, Z 1 , Z 2 , and Z 3 can each be a substituent as described herein, such as the aforementioned hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group.

[0062] As used herein, "amide" or "amido" is represented by the formula -C(O)NZ1 Z 2 represented by, wherein Z 1 and Z 2 are each a substituent described herein, such as the above-mentioned hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group, and can be such substituents.

[0063] As used herein, the term "anhydride" is represented by the formula Z 1 C(O)OC(O)Z 2 represented by, wherein Z 1 and Z 2 can each be the above-mentioned alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group.

[0064] As used herein, the term "cyclic anhydride" is represented by the following formula:

Chemical formula

[0065] As used herein, the term "azide" is represented by the formula -N=N=N.

[0066] As used herein, the term "carboxylic acid" is represented by the formula -C(O)OH.

[0067] As used herein, the term "carboxylate" or "carboxyl" group is represented by the formula -C(O)O - represented by.

[0068] As used herein, the term "carbonate" group is represented by the formula Z 1 OC(O)OZ2 is represented by

[0069] As used herein, the term "cyano" is represented by the formula -CN.

[0070] As used herein, the term "ester" is represented by the formula -OC(O)Z 1 or -C(O)OZ 1 wherein Z 1 can be an alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group as described above.

[0071] As used herein, the term "ether" is represented by the formula Z 1 OZ 2 wherein Z 1 and Z 2 can each be an alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group as described above.

[0072] As used herein, the term "epoxy" or "epoxide" refers to a cyclic ether having a three - membered ring and can be represented by the following formula:

Chemical formula

[0073] As used herein, the term "ketone" is represented by the formula Z 1 C(O)Z 2 wherein Z 1 and Z 2can each be an alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group as described above.

[0074] As used herein, the terms "halide", "halogen", or "halo" refer to fluorine, chlorine, bromine, and iodine.

[0075] As used herein, the term "hydroxyl" is represented by the formula -OH.

[0076] As used herein, the term "nitro" is represented by the formula -NO2.

[0077] The term "phosphonyl" is used herein to refer to a phospho-oxo group represented by the formula -P(O)(OZ 1 )2, wherein Z 1 can be a hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group as described above.

[0078] As used herein, the term "silyl" is represented by the formula -SiZ 1 Z 2 Z 3 wherein Z 1 Z 2 Z 3 can each be a hydrogen, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group as described above.

[0079] The term "sulfonyl" or "sulfone" is used herein to refer to a sulfo-oxo group represented by the formula -S(O)2Z 1 wherein Z 1can be a hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group as described above.

[0080] As used herein, the term "sulfide" includes the formula -S-.

[0081] As used herein, the term "thiol" is represented by the formula -SH.

[0082] As used herein, "R 1」 ", "R 2 ", "R 3 ", "R n " (where n is an integer), etc. can each have one or more of the groups listed above. For example, when R 1 is a linear alkyl group, one of the hydrogen atoms of the alkyl group can optionally be substituted by a hydroxyl group, an alkoxy group, an amine group, an alkyl group, a halide, etc. Depending on the group selected, the first group can be incorporated into the second group or, alternatively, the first group can be pendant (i.e., attached) to the second group. For example, with respect to the phrase "alkyl group containing an amino group", the amino group can be incorporated into the backbone of the alkyl group. Alternatively, the amino group can be attached to the backbone of the alkyl group. The nature of the group selected determines whether the first group is embedded in or attached to the second group.

[0083] Unless otherwise specified, a formula having chemical bonds shown only as solid lines rather than as wedges or dashed lines contemplates each possible stereoisomer or mixture of stereoisomers (e.g., each enantiomer, each diastereomer, each meso compound, a racemic mixture, or a scalemic mixture).

[0084] Product Liner As used herein, a liner (104) is provided that includes a septum (110) and a layer that includes a thermoplastic polymer (108), where the septum (110) includes an elastomer and the septum (110) is bonded to the layer that includes the thermoplastic polymer (108).

[0085] As used herein, the liner (104) can securely enclose a sample within a container, for example, via a syringe (118), such that the sample is separated from the external environment and at the same time, extraction of the sample is enabled.

[0086] Referring now to FIGS. 5A - 5B, FIG. 5A is a perspective view of an exemplary liner (104) having a diameter of 24 mm. FIG. 5B is a side perspective view of an exemplary liner (104) having a diameter of 24 mm that includes an exemplary septum (110) that includes silicone rubber bonded to an exemplary first layer of a first thermoplastic polymer (108), where the first thermoplastic polymer includes polypropylene.

[0087] As used herein, the septum (110) refers to a membrane used in techniques for transferring substances. In some examples, the septum (110) can be made of rubber. In further examples, the membrane can be chemical resistant. In specific examples, the septum (110) can be used by a syringe (118) to transfer substances to a gas chromatograph, liquid chromatograph, mass spectrometer, or any combination thereof for separation, purification, and / or identification, for example, from a vial. The septum (110) can be used when transferring solids, liquids, gases, or any combination thereof.

[0088] The septum (110) may include an elastomer. An elastomer is any material that exhibits elastic or rubbery properties and can be natural or synthetic. Elastomeric materials (e.g., materials containing an elastomer) include, but are not limited to, foams and sponges, rubber, cork products, and any combination thereof. Examples of rubber include, for example, urethane, chloroprene, neoprene, isoprene rubber, acrylonitrile butadiene rubber, ethylene propylene rubber, fluoroelastomer, silicone rubber, styrene butadiene rubber, fluorosilicone, and polyisobutylene rubber (also referred to as "butyl").

[0089] In some examples, the elastomer includes silicone rubber. Silicone rubber is a durable and resistant elastomer that includes silicone containing silicon, carbon, hydrogen, and oxygen. Silicone rubber includes a siloxane backbone and an organic moiety bonded to silicon according to the following general formula (where "R" is an organic moiety).

Chemical formula

[0090] Silicone can have a tensile strength of 500 - 2500 psi and an elongation rate of 450 - 900%. Silicone is ozone resistant and can withstand low temperatures (e.g., as low as -75°F) and high temperatures (e.g., as high as 500°F). In some examples, the silicone rubber is room temperature vulcanizing silicone rubber.

[0091] The liner (104) further includes a layer containing a thermoplastic polymer. Like all polymers, a thermoplastic polymer is composed of small molecules called monomers, which form long chains through a polymerization process. For example, one thermoplastic polymer chain can contain thousands of monomers. Examples of thermoplastic polymers include, but are not limited to, polyethylene (PE), polypropylene (PP), polyvinyl chloride (PVC), polystyrene (PS), polyethylene terephthalate (PET), polybutylene terephthalate (PBT), and polyamide (PA).

[0092] In a further example, a liquid disposed on the thermoplastic polymer has a contact angle with the thermoplastic polymer of 0° to 90°. The contact angle is a measure of the ability of a liquid to wet the surface of a solid. The contact angle is the angle formed by the liquid at the three-phase boundary where the liquid, gas, and solid intersect. As the contact angle decreases, the surface energy increases, the surface tension decreases, and the wettability increases. In some examples, when the contact angle between the liquid and the surface is less than 90°, it is very advantageous for the liquid to wet the surface, and the liquid can spread over a large area of the surface. As described herein, a liquid having a contact angle of less than 90° with the thermoplastic polymer can be advantageous for binding the thermoplastic polymer to an elastomer (e.g., for binding polypropylene to silicone).

[0093] In a specific example, the thermoplastic polymer includes polypropylene. Polypropylene is a thermoplastic polymer derived from propylene monomers and can have the formula shown below. Polypropylene can be produced through chain-growth polymerization. Polypropylene can have a melting point of 320°F. [Chemical formula]

[0094] In the liner (104), a layer of thermoplastic polymer (108) is bonded to a septum (110) containing an elastomer. The thermoplastic polymer can be bonded to the elastomer using methods known in the art. For example, the thermoplastic polymer can be bonded to the elastomer via the application of a bonding composition such as a primer, a prime coat, an adhesion promoter, or any combination thereof, which can be a dilute solution containing a silane coupling agent along with other active ingredients. The bonding composition is generally liquid and enhances adhesion and bonding to various silicone materials. In some examples, these materials include, but are not limited to, Dow Corning® 3-6060, 92-023, S-2260, or any combination thereof.

[0095] In a further example, the liner (104) includes a septum (110) having a top surface and a bottom surface, the bottom surface being on the opposite side of and spaced from the top surface. The liner may further include a first layer including a first thermoplastic polymer (108), the first layer having, for example, a first surface and a second surface, the second surface being on the opposite side of and spaced from the first surface. In some examples of the liner (104), the bottom surface of the septum (110) is disposed on and in physical contact with the first surface of the first layer including the first thermoplastic polymer (108), such that the septum (110) is disposed on the first layer including the first thermoplastic polymer (108). In some examples, the top surface of the septum (110) is bonded to the first surface of the first layer including the first thermoplastic polymer (108). In a further example, the septum (110) may be disposed on a second layer including a second thermoplastic polymer (108) having, for example, a third surface and a fourth surface, the third surface being on the opposite side of and spaced from the fourth surface. In a particular example, the top surface of the septum (110) is disposed on and in physical contact with the third surface of the second layer including the second thermoplastic polymer (108), such that the septum (110) is disposed on the second layer such that the septum (110) is sandwiched between the first layer of the first thermoplastic polymer (108) and the second layer of the second thermoplastic polymer (108). In some examples, the bottom surface of the septum (110) is disposed on and in physical contact with the third surface of the second layer including the second thermoplastic polymer (108), such that the septum (110) is disposed on the second layer such that the septum (110) is sandwiched between the first layer of the first thermoplastic polymer (108) and the second layer of the second thermoplastic polymer (108).

[0096] Referring to FIGS. 8A-8B below, FIG. 8A is a perspective view of an exemplary liner (104) having a diameter of 24 mm. FIG. 8B is a perspective view of an exemplary septum (110) including a silicone rubber bonded to an exemplary first layer of a first thermoplastic polymer (108) on its top surface and an exemplary second layer of a second thermoplastic polymer (108) on its bottom surface, the liner (104) including a septum (110), and the first and second thermoplastic polymers include polypropylene.

[0097] In a specific example, the liner (104) can have a thickness and a cross-sectional shape. The cross-sectional shape can be, for example, substantially circular.

[0098] In some examples, the liner (104) has an average characteristic dimension. As used herein, the term "characteristic dimension" refers to the longest straight-line distance between two points in the plane of the cross-sectional shape. "Average characteristic dimension" generally refers to a statistical average characteristic dimension. For example, when the liner has a cross-sectional shape that is substantially circular, the average characteristic dimension can refer to the average diameter, which is used interchangeably herein with "diameter". In the case of a cap (102) without threads (106), the average diameter can refer to the inner diameter of the cap (102). In the case of a cap (102) having threads (106), the average diameter can refer to the longest straight-line distance between two points inside the threads (106).

[0099] In some examples, the liner (104) can have an average characteristic dimension of 9 millimeters (mm) or more (e.g., 10 mm or more, 11 mm or more, 12 mm or more, 13 mm or more, 14 mm or more, 15 mm or more, 16 mm or more, 17 mm or more, 18 mm or more, 19 mm or more, 20 mm or more, 21 mm or more, 22 mm or more, 23 mm or more, 24 mm or more, 25 mm or more, 26 mm or more, 27 mm or more, 28 mm or more, or 29 mm or more). In some examples, the liner (104) can have an average characteristic dimension of 30 mm or less (e.g., 29 mm or less, 28 mm or less, 27 mm or less, 26 mm or less, 25 mm or less, 24 mm or less, 23 mm or less, 22 mm or less, 21 mm or less, 20 mm or less, 19 mm or less, 18 mm or less, 17 mm or less, 16 mm or less, 15 mm or less, 14 mm or less, 13 mm or less, 12 mm or less, 11 mm or less, or 10 mm or less). The average characteristic dimension of the liner (104) can be in the range from any of the above-mentioned minimum values to any of the above-mentioned maximum values. For example, the liner 9104) can have an average characteristic dimension of 9 millimeters (mm) to 30 mm (e.g., 9 - 12 mm, 12 - 15 mm, 15 - 18 mm, 18 - 21 mm, 21 - 24 mm, 24 - 27 mm, 27 - 30 mm, 9 - 15 mm, 9 - 18 mm, 9 - 21 mm, 9 - 24 mm, 9 - 27 mm, 9 - 30 mm, 20 - 22 mm, 20 - 24 mm, 20 - 26 mm, 20 - 28 mm, 20 - 30 mm, 22 - 23 mm, 23 - 24 mm, 24 - 25 mm, 25 - 26 mm, 16 - 18 mm, 16 - 20 mm, 16 - 22 mm, 16 - 24 mm, 18 - 19 mm, 19 - 20 mm, 20 - 21 mm, or 21 - 22 mm). In a further example, the liner (104) has a diameter of 24 mm. In a specific example, the liner (104) has a diameter of 20 mm.

[0100] In some examples, the liner (104) has a thickness of 0.5 inches (inches) or less (e.g., 0.4 inches or less, 0.3 inches or less, 0.2 inches or less, or 0.1 inches or less). In certain examples, the liner (104) has a thickness of 0 to 0.1 inches, 0.1 to 0.2 inches, 0.2 to 0.3 inches, 0.3 to 0.4 inches, or 0.4 to 0.5 inches. In a specific example, the liner (104) has a thickness of 0 to 0.05 inches, 0.05 to 0.1 inches, 0.1 to 0.15 inches, 0.15 to 0.2 inches, 0.2 to 0.25 inches, 0.25 to 0.3 inches, 0.3 to 0.35 inches, 0.35 to 0.4 inches, 0.4 to 0.45 inches, or 0.45 to 0.5 inches. In some examples, the liner (104) has a thickness of 0 to 0.1 inches, 0 to 0.2 inches, 0 to 0.3 inches, 0 to 0.4 inches, or 0 to 0.5 inches.

[0101] In a specific example, the liner (104) is substantially free of perfluoroalkyl and polyfluoroalkyl substances (PFAS). In some examples, the liner (104) is free of PFAS. In some examples, the liner (104) contains PFAS in an amount of 0 parts per trillion to 140,000 parts per trillion (e.g., 0 to 20,000 parts per trillion, 20,000 to 40,000 parts per trillion, 40,000 to 60,000 parts per trillion, 60,000 to 80,000 parts per trillion, 80,000 to 100,000 parts per trillion, 100,000 to 120,000 parts per trillion, or 120,000 to 140,000 parts per trillion). In a further example, the liner (104) contains 140,000 parts per trillion or less (e.g., a maximum of 140,000 parts per trillion, a maximum of 130,000 parts per trillion, a maximum of 120,000 parts per trillion, a maximum of 110,000 parts per trillion, a maximum of 100,000 parts per trillion, a maximum of 90,000 parts per trillion, a maximum of 80,000 parts per trillion, a maximum of 70,000 parts per trillion, a maximum of 60,000 parts per trillion, a maximum of 50,000 parts per trillion, a maximum of 40,000 parts per trillion, a maximum of 30,000 parts per trillion, a maximum of 20,000 parts per trillion, or a maximum of 10,000 parts per trillion). In a particular example, the liner (104) contains 0 parts per trillion to 1,000 parts per trillion (e.g., 0 to 100 parts per trillion, 100 to 200 parts per trillion, 200 to 300 parts per trillion, 300 to 400 parts per trillion, 400 to 500 parts per trillion, 500 to 600 parts per trillion, 600 to 700 parts per trillion, 700 to 800 parts per trillion, 800 to 900 parts per trillion, or 900 to 1,000 parts per trillion).In a specific example, the liner 9104) contains from 0 parts per trillion to 100 parts per trillion (for example, 0 to 10 parts per trillion, 10 to 20 parts per trillion, 20 to 30 parts per trillion, 30 to 40 parts per trillion, 40 to 50 parts per trillion, 50 to 60 parts per trillion, 60 to 70 parts per trillion, 70 to 80 parts per trillion, 80 to 90 parts per trillion, or 90 to 100 parts per trillion).

[0102] PFAS includes molecules composed of linked carbon and fluorine atoms. Due to the strength of the carbon-fluorine bond, PFAS can decompose very slowly or not at all. PFAS can be used in coatings for cooking utensils, stain-resistant clothing, and carpets, or in foam fire extinguishers to enhance their effectiveness. Additionally, PFAS can be used in industries such as aerospace, automotive, construction, electronics, and military. Currently, over 9,000 types of PFAS have been identified. Concerns about the impact of PFAS on public health are increasing due to the fact that PFAS can remain in the environment for an unknown period of time, gradually accumulate, and stay in the human body.

[0103] PFAS includes, but is not limited to, perfluorooctanoic acid (PFOA), perfluorooctane sulfonate (PFOS), hexafluoropropylene oxide (HFPO) dimer acid, and their ammonium, sodium, potassium salts, or any combination thereof. Further examples of PFAS include N-ethyl perfluorooctane sulfonamide acetic acid, N-methyl perfluorooctane sulfonamide acetic acid, perfluorobutane sulfonic acid, perfluorodecanoic acid, perfluorododecanoic acid, perfluoroheptanoic acid, perfluorohexane sulfonic acid, perfluorohexanoic acid, and perfluorononanoic acid. In a specific example, PFAS includes perfluorooctanoic acid (PFOA), perfluorooctane sulfonic acid (PFOS), or any combination thereof.

[0104] Cap assembly Also provided herein is a cap assembly (100) comprising a liner (104) disclosed herein and a cap (102), with the cap (102) coupled to the liner (104). For example, the liner (104) can be coupled inside the cap (102). The liner (104) can be coupled to the cap (102) using methods known in the art, such as those disclosed in U.S. Patent Nos. 5,647,939 and / or 6,234,335.

[0105] As used herein, the cap (102) is a lid for an object such as a vial (112). Herein, the cap (102) seals the vial (112) to prevent, for example, evaporation and / or contamination of a sample contained within the vial. The cap (102) disclosed herein can be, for example, a screw cap, a crimp cap, or a snap cap, meaning that the cap (102) can be screwed onto the vial (112), crimped onto the vial (112), or snap-fastened onto the vial (112), respectively. In some examples, the cap (102) is made of plastic, and the plastic can be a thermosetting plastic, a thermoplastic, or any combination thereof. Examples of plastics include, but are not limited to, phenolic resins, polyolefins, or any combination thereof. Examples of polyolefins include, but are not limited to, polyethylene, polypropylene, polybutylene, or any combination thereof.

[0106] In some examples, the cap (102) includes a thermoplastic polymer. In further examples, the cap (102) includes polypropylene.

[0107] In certain examples, the cap (102) comprises a thread (106).

[0108] Referring to FIGS. 6A - 6C below, FIG. 6A is a perspective view of an exemplary cap (102) made of plastic and including a thread (106) for coupling to a vial via a screw mechanism. FIG. 6B is a perspective view of an exemplary cap (102) made of plastic and including a thread (106). FIG. 6C is a side perspective view of an exemplary cap (12) made of plastic and having a diameter of 24 mm.

[0109] In a specific example, the cap (102) includes a metal. The metal is any class of substances characterized by high electrical and thermal conductivity and, in some aspects, malleability, ductility, and high light reflectivity. Examples of metals include, but are not limited to, aluminum, copper, brass, magnesium, tin, lead, bronze, zinc, or any combination thereof.

[0110] In some examples, the metal is malleable. Malleability describes the ability to deform the metal under compression. Thus, a malleable metal enables the cap (102) to be deformed via techniques such as crimping.

[0111] In a further example, the metal includes aluminum. Aluminum is silver - white, lightweight, highly corrosion - resistant, malleable, ductile, and has a low density. The cap (102) described herein can be made of aluminum, as in some examples, and the cap (102) is sealed to the vial (112) via a crimping mechanism, which utilizes the malleability and ductility of aluminum.

[0112] In a particular example, the cap (102) has a cross - sectional shape. In some examples, the cross - sectional shape of the cap (102) is substantially circular.

[0113] In a specific example, the cap (102) can have an average characteristic dimension of 9 millimeters (mm) or more (e.g., 10 mm or more, 11 mm or more, 12 mm or more, 13 mm or more, 14 mm or more, 15 mm or more, 16 mm or more, 17 mm or more, 18 mm or more, 19 mm or more, 20 mm or more, 21 mm or more, 22 mm or more, 23 mm or more, 24 mm or more, 25 mm or more, 26 mm or more, 27 mm or more, 28 mm or more, or 29 mm or more). In some examples, the cap (102) can have an average characteristic dimension of 30 mm or less (e.g., 29 mm or less, 28 mm or less, 27 mm or less, 26 mm or less, 25 mm or less, 24 mm or less, 23 mm or less, 22 mm or less, 21 mm or less, 20 mm or less, 19 mm or less, 18 mm or less, 17 mm or less, 16 mm or less, 15 mm or less, 14 mm or less, 13 mm or less, 12 mm or less, 11 mm or less, or 10 mm or less). The average characteristic dimension of the cap (102) can be in the range from any of the above-mentioned minimum values to any of the above-mentioned maximum values. For example, the cap (102) can have an average characteristic dimension of 9 millimeters (mm) to 30 mm (e.g., 9 to 12 mm, 12 to 15 mm, 15 to 18 mm, 18 to 21 mm, 21 to 24 mm, 24 to 27 mm, 27 to 30 mm, 9 to 15 mm, 9 to 18 mm, 9 to 21 mm, 9 to 24 mm, 9 to 27 mm, 9 to 30 mm, 20 to 22 mm, 20 to 24 mm, 20 to 26 mm, 20 to 28 mm, 20 to 30 mm, 22 to 23 mm, 23 to 24 mm, 24 to 25 mm, 25 to 26 mm, 16 to 18 mm, 16 to 20 mm, 16 to 22 mm, 16 to 24 mm, 18 to 19 mm, 19 to 20 mm, 20 to 21 mm, or 21 to 22 mm). In some examples, the cap (102) has an average characteristic dimension of 24 mm. In a further example, the cap (102) has an average characteristic dimension of 20 mm.

[0114] Referring to FIGS. 1A - 1B below, FIG. 1A is a perspective view of an exemplary cap assembly (100) comprising a liner (104) coupled inside a cap (102) such that the liner (104) hides the hole of the cap (102). Further, the cap (102) has threads (106) inside the cap (102), and thus the cap can be coupled to a vial (112) via a threading mechanism.

[0115] Referring to FIG. 3 below, an exemplary cap assembly (100) is shown comprising an exemplary cap (102) having a 24 - mm diameter, made of polypropylene, and having threads (106), and a liner (104) coupled therein.

[0116] Cap and vial assembly Also provided herein is a cap and vial assembly (114) comprising the cap assembly (100) disclosed herein and a vial (112), with the cap assembly (100) being coupled to the vial (112).

[0117] As used herein, a vial (112) is a closable container that can hold solids, liquids, gases, or any combination thereof. The vial (112) can be made of any suitable material. For example, the vial (112) can be made of plastic, glass, or any combination thereof, but is not limited thereto. Examples of the vial (112) can include, but are not limited to, containers, well plates of any volume, ampoules, or bottles. Examples of plastics that can be used to make the vial (112) include, but are not limited to, acrylic, high-density polyethylene, or any combination thereof. In some examples, the vial (112) can be made of pharmaceutical-grade plastic. In further examples, the vial (112) can be made of glass, and examples of the glass used to make the vial (112) can include, but are not limited to, soda-lime glass, borosilicate glass, or any combination thereof. In further examples, the vial (112) includes glass. In a specific example, the glass includes borosilicate glass. In a specific example, the vial (112) includes plastic.

[0118] Referring now to FIGS. 7A - 7C, these figures are perspective views of an exemplary vial (112) made of glass, including threads (116), the threads enabling the vial (112) to be coupled to a cap or cap assembly via a threading mechanism.

[0119] In some examples, the vial (112) can have a volume of 1 mL to 500 mL (e.g., 1 - 50 mL, 50 - 100 mL, 100 - 150 mL, 150 - 200 mL, 200 - 250 mL, 250 - 300 mL, 300 - 350 mL, 350 - 400 mL, 400 - 450 mL, or 450 - 500 mL).

[0120] In some examples, the cap (102) and the vial (112) each independently comprise threads (106, 116) such that the cap assembly (100) is configured to be coupled to the vial (112) by a threading mechanism. As used herein, a "threading mechanism" refers to a mechanism in which a cylindrical shaft having a helical groove known as a thread around at least a portion of the outside of the shaft passes through a hole in another object or medium having threads inside the hole, and the threads inside the hole mesh with the threads outside the shaft. In this specification, the threads on the cylindrical shaft are the threads (116) on the vial (112), and the threads inside the hole are the threads (106) inside the cap (102). By screwing the cap assembly (100) onto the vial (112), the cap assembly (100) is sealed to the vial (112), and thus the contents of the vial (112) are encapsulated within the vial (112) to minimize or prevent, for example, evaporation and / or contamination.

[0121] In a further example, the cap assembly (100) is configured to be coupled to the vial (112) by a crimping mechanism. As used herein, a "crimping mechanism" refers to a mechanism in which an object made of a malleable metal is attached to a container such as the vial (112) by bending the metal over the outer edge of the vial (112). This can be done by a device such as a vial crimper. In this specification, the crimping mechanism is utilized as a means of sealing the metal cap assembly (100) to the vial (112) such that the contents of the vial (112) are encapsulated within the vial (112) to minimize or prevent, for example, evaporation and / or contamination, and necessarily involves placing the metal cap assembly (100) on the vial (112) and using a crimping tool to crimp the cap assembly (100) to the vial (112).

[0122] In certain examples, the cap assembly (100) is configured to be coupled to the vial (112) by a snap mechanism. As used herein, a "snap mechanism" refers to a mechanism by which the cap (102) is clamped to the container through the application of a force to the cap (102). As used herein, the snap mechanism is used as a means of sealing the plastic cap assembly (100) to the vial (112) such that, for example, the contents of the vial (112) are enclosed within the vial (112) to minimize or prevent evaporation and / or contamination, and necessarily, the cap assembly (100) is placed over the vial (112), a force is applied to the cap assembly (100), and thus, it clamps onto the top of the vial (112).

[0123] Referring now to FIGS. 4A - 4C, FIG. 4A is an exploded perspective view of an exemplary cap and vial assembly (114). An exemplary cap (102) made of plastic and having a diameter of 24 mm is coupled to an exemplary liner (104) having a diameter of 24 mm, and the liner (104) includes an exemplary septum (110) including silicone rubber bonded to a layer of an exemplary thermoplastic polymer (108) including polypropylene. The cap (102) and the liner (104) can be coupled to an exemplary vial (112) via a screw mechanism using the threads (116) of the vial (112). FIG. 4B is a perspective view of an exemplary cap and vial assembly (114). An exemplary cap assembly (100) including an exemplary cap (102) made of plastic and having a diameter of 24 mm is coupled to an exemplary vial (112) including glass. FIG. 4C is a perspective view of an exemplary cap and vial assembly (114) comprising an exemplary cap assembly (100) including an exemplary cap (102) made of plastic and having a diameter of 24 mm, an exemplary liner (104) having a diameter of 24 mm and including silicone rubber and polypropylene, and being coupled to an exemplary vial (112) including glass.

[0124] Method Water quality test method In one aspect, the present disclosure provides a method for testing the water quality in a sample.

[0125] Water quality testing can follow various regulations and methods that may depend on factors such as the designated uses of the water body, the criteria for protecting the designated uses, and the requirements for preventing degradation to protect existing uses and high-quality / high-value water. Examples of the designated uses of water can include (1) protection and propagation of fish, crustaceans, and wildlife, (2) recreation, (3) public drinking water supply, or (4) agriculture, industry, navigation, and other purposes. Water quality testing can include testing water for contaminants such as PFAS, as well as other contaminants. In some examples, the criteria for the method of water quality testing can be determined by the U.S. Environmental Protection Agency (EPA), the European Chemicals Agency (ECHA), Environment Canada, states, localities, recognized tribal organizations, or any combination thereof. Additionally, water quality criteria such as maximum concentration levels of contaminants or specifications for desired water conditions can also be determined by the above organizations. An exemplary method for water quality testing of PFAS in drinking water is included in Shoemaker, J.A. and Tettenhorst, D.R., Method 537.1: Determination of Selected Per- and Polyfluorinated Alkyl Substances in Drinking Water by Solid Phase Extraction and Liquid Chromatography / Tandem Mass Spectrometry (LC / MS / MS), EPA Document #: EPA / 600 / R-18 / 352, Version 1.0, November 2018.

[0126] For example, in one aspect, the present disclosure provides a method of testing the water quality in a sample using an analytical instrument, wherein the sample is contained within a container comprising a liner (104) disclosed herein, a cap assembly (100) disclosed herein, and a cap and vial assembly (114) disclosed herein, the method including withdrawing a portion of the sample through the liner (104) with a syringe (118) and testing a portion of the sample using the analytical instrument.

[0127] As used herein, a syringe (118) is a reciprocating pump that includes a plunger that fits snugly within a cylindrical tube having a longitudinal axis. The plunger can be displaced axially linearly along the inside of the tube (e.g., pulled and / or pushed), enabling the syringe (118) to take in liquid or gas at an open end of the tube and discharge it through a discharge orifice. The end of the open tube can be fitted, for example, with a hypodermic needle, nozzle, and / or tube to direct flow in and out of the syringe (118). As used herein, "syringe" and "needle" are used interchangeably. Further, the syringe (118) can include a syringe or needle connected to an autosampler device, and the autosampler is a device that automatically loads collected samples into experimental utility instruments (e.g., analytical instruments) such as gas chromatographs, liquid chromatographs, mass spectrometers, or any combination thereof. The syringe (118) can be single-use or multi-use.

[0128] Furthermore, the syringe (118) can have any suitable size and / or volume. In some examples, the syringe (118) can have a volume of 1 mL to 50 mL (e.g., 1 mL to 10 mL, 10 mL to 20 mL, 20 mL to 30 mL, 30 mL to 40 mL, or 40 mL to 50 mL). In further examples, the syringe (118) can have a volume of 1 mL to 25 mL or 25 mL to 50 mL (e.g., 1 mL to 5 mL, 1 mL to 10 mL, 1 mL to 15 mL, 1 mL to 20 mL, 1 mL to 25 mL, 1 mL to 30 mL, 1 mL to 35 mL, 1 mL to 40 mL, 1 mL to 45 mL, or 1 mL to 50 mL).

[0129] In some examples, the syringe (118) can have a volume of 5 to 1000 μL. In further examples, the syringe (118) can have a volume of 5 to 100, 100 to 200, 200 to 300, 300 to 400, 400 to 500, 500 to 600, 600 to 700, 700 to 800, 800 to 900, or 900 to 1000 μL. In certain examples, the syringe (118) can have a volume of 5 μL or more, 10 μL or more, 25 μL or more, 50 μL or more, 100 μL or more, 250 μL or more, 500 μL or more, or 1000 μL or more. A syringe (118) having a volume of 5 to 1000 μL can also be referred to as a "micro syringe".

[0130] In some examples, the analytical instrument is a gas chromatograph, a liquid chromatograph, a mass spectrometer, or any combination thereof.

[0131] Gas chromatography is an analytical technique used to separate the chemical components of a mixture, detect the chemical components, and determine the presence, absence, and / or concentration of the chemical components. The chemical components to be detected may include organic molecules or gases. Gas chromatography can be used for quality control, research, or environmental samples, microplastics, or food safety and monitoring in the manufacture of products ranging from automobiles to chemical products such as petrochemicals or pharmaceuticals. Gas chromatography can be performed on a gas chromatograph (GC). The GC operates by transporting sample molecules from solids, liquids, and / or gases in a carrier gas through a heated analytical column into a detector, and the detector generates a signal in response to the chemical components eluting from the column, and the signal is recorded by appropriate software to generate a chromatogram. The sample can be extracted via a syringe (118) and / or an autosampler. If the sample is not a gas, the chemical components of the sample are first evaporated.

[0132] Liquid chromatography is an analytical technique that dissolves sample ions or molecules in a liquid mobile phase. Liquid chromatography can be performed on a liquid chromatograph (LC) that operates by transporting the sample in the liquid mobile phase through a column or a plane packed with a stationary phase. Different solutes interact with the stationary phase to different extents due to differences in ion exchange, adsorption, partitioning, and / or size, and thus separate the compounds. Based on these differences, the transit time of the solute through the column is determined. The sample can be extracted into the liquid chromatograph via a syringe (118) and / or an autosampler.

[0133] The gas chromatograph and / or liquid chromatograph can further be equipped with a mass spectrometer.

[0134] Mass spectrometry is an analytical tool useful for measuring the mass-to-charge ratio (m / z) of one or more molecules present in a sample. A mass spectrometer (MS) can convert individual molecules from a sample into ions and move and manipulate the ions by an internal electromagnetic field. A mass spectrometer comprises three components, namely, an ion source, a mass analyzer, and a detector. The ion source ionizes the sample. In some examples, the ion source ionizes the sample into cations by the loss of electrons. In further examples, the ion source ionizes the sample into anions. The mass analyzer classifies and separates the ions according to the mass and charge of the ions. The detector measures the separated ions and displays the results on a chart. In some examples, the mass spectrometer can be used together with a gas chromatograph and / or a liquid chromatograph.

[0135] In further examples, the method includes taking out one or more portions of the sample by the syringe (118) penetrating the liner (104) one or more times (for example, 2 or more times, 3 or more times, 4 or more times, 5 or more times, 6 or more times, 7 or more times, 8 or more times, 9 or more times, 10 or more times, 11 or more times, 12 or more times, 13 or more times, 14 or more times, 15 or more times, 16 or more times, 17 or more times, 18 or more times, or 19 or more times). In some examples, the method includes taking out one or more portions of the sample by the syringe (118) penetrating the liner (104) 20 or fewer times (for example, 19 or fewer times, 18 or fewer times, 17 or fewer times, 16 or fewer times, 15 or fewer times, 14 or fewer times, 13 or fewer times, 12 or fewer times, 11 or fewer times, 10 or fewer times, 9 or fewer times, 8 or fewer times, 7 or fewer times, 6 or fewer times, 5 or fewer times, 4 or fewer times, 3 or fewer times, or 2 or fewer times). The number of times of penetrating the liner (and thus the number of portions of the sample taken out) can range from any of the above minimum values to the above maximum values. For example, the method can include taking out one or more portions of the sample by the syringe (118) penetrating the liner (104) 1 to 20 times.

[0136] Referring now to FIGS. 2A - 2B, FIG. 2A shows an exemplary cap and vial assembly (114) in which a syringe (118) actively penetrates a liner (104). The exemplary liner (104) has a diameter of 9 mm and is coupled to an exemplary cap (102) having a corresponding diameter of 9 mm, thus providing an exemplary cap assembly (100). The exemplary vial (112) is 1.5 mL and includes glass. FIG. 2B similarly shows an exemplary cap and vial assembly (114) in which a syringe (118) actively penetrates a liner (104). The exemplary liner (104) of FIG. 2B has a diameter of 24 mm and is coupled to an exemplary cap (102) having a corresponding diameter of 24 mm, thus providing an exemplary cap assembly (100). The exemplary vial (112) is 20 mL and includes glass.

[0137] Referring now also to FIGS. 9A - 9C, FIG. 9A is an exploded perspective view of an exemplary cap and vial assembly (114). An exemplary cap (102) made of plastic and having a 24 mm diameter is coupled to an exemplary liner (104) having a 24 mm diameter, the liner (104) including an exemplary septum (110) comprising silicone rubber bonded to a first exemplary layer of thermoplastic polymer (108) on its top surface and a second exemplary layer of thermoplastic polymer (108) on its bottom surface, the polymer including polypropylene. The cap (102) and liner (10) are then coupled to an exemplary vial (112) via a screw mechanism using threads (116) on the vial (112). FIG. 9B is a perspective view of the exemplary cap and vial assembly (114). An exemplary cap assembly (100) made of plastic and having a 24 mm diameter, including the exemplary cap (102), is coupled to an exemplary vial (112) comprising glass. FIG. 9C is a perspective view of an exemplary cap and vial assembly (114) comprising an exemplary cap assembly (100) including an exemplary cap (102) made of plastic and having a 24 mm diameter, an exemplary liner (104) having a 24 mm diameter and comprising silicone rubber and polypropylene, and coupled to an exemplary vial (112) comprising glass.

[0138] Numerous embodiments of the present disclosure have been described. Nevertheless, it will be understood that various modifications may be made without departing from the spirit and scope of the invention. Accordingly, other embodiments are within the scope of the following claims.

[0139] Other advantages, which are apparent and specific to the present invention, will be apparent to those skilled in the art. It will be understood that certain features and subcombinations are useful and may be employed without reference to other features and subcombinations. This is contemplated by the claims and is within the scope of the claims. Since many possible embodiments may be made from the present invention without departing from their scope, all matters described or shown in the accompanying drawings should be construed as illustrative and not in a limiting sense.

[0140] The methods and products of the appended claims are not limited in scope by the specific methods and products described herein, but are intended as illustrations of some aspects of the claims and any methods and products functionally equivalent are intended to be within the scope of the claims. In addition to what is illustrated and described herein, various modifications of the methods and products are intended to be within the scope of the appended claims. Further, although only certain representative method steps specifically disclosed herein are specifically described, other combinations of method steps, even if not specifically recited, are intended to be within the scope of the appended claims. Thus, steps, elements, components, or combinations thereof may be explicitly recited herein, but other combinations of steps, elements, components, and elements are included even if not explicitly stated.

Claims

1. A liner comprising a septum and a layer, the layer comprising a thermoplastic polymer, the septum comprising an elastomer, and the septum bonded to the layer comprising the thermoplastic polymer.

2. The liner of claim 1 , wherein the elastomer comprises a silicone rubber.

3. The liner of claim 1, wherein a liquid disposed on the thermoplastic polymer has a contact angle with the thermoplastic polymer of between 0° and 90°.

4. The liner of claim 1 , wherein the thermoplastic polymer comprises polypropylene.

5. The liner of claim 1 , wherein the liner has a thickness and a cross-sectional shape, the cross-sectional shape being substantially circular.

6. The liner of claim 1 , wherein the liner has an average characteristic dimension between 9 millimeters (mm) and 30 mm.

7. The liner of claim 1 , wherein the liner has a diameter of 24 mm.

8. The liner of claim 1 , wherein the liner has a diameter of 20 mm.

9. The liner of claim 1 , wherein the liner is free of perfluoroalkyl and polyfluoroalkyl substances (PFAS).

10. The liner of claim 1 , wherein the liner is substantially free of PFAS.

11. The liner of claim 1 , wherein the liner comprises 0 parts per trillion to 140,000 parts per trillion of PFAS.

12. 10. The liner of claim 9, wherein the PFAS comprises perfluorooctanoic acid (PFOA), perfluorooctanesulfonic acid (PFOS), or any combination thereof.

13. The liner of claim 1 , wherein the liner has a thickness of 0.5 inches or less.

14. A cap assembly comprising the liner of claim 1 and a cap, said cap being coupled to said liner.

15. The cap assembly of claim 14 , wherein the cap comprises a thermoplastic polymer.

16. The cap assembly of claim 14 , wherein the cap comprises polypropylene.

17. The cap assembly of claim 14 , wherein the cap comprises threads.

18. The cap assembly of claim 14 , wherein the cap comprises a metal.

19. The cap assembly of claim 18 , wherein the metal is malleable.

20. The cap assembly of claim 18 , wherein the metal comprises aluminum.

21. The cap assembly of claim 14 , wherein the cap has a cross-sectional shape, the cross-sectional shape being substantially circular.

22. The cap assembly of claim 14, wherein the cap has an average characteristic dimension between 9 mm and 30 mm.

23. The cap assembly of claim 14, wherein the cap has an average characteristic dimension of 24 mm.

24. The cap assembly of claim 14, wherein the cap has an average characteristic dimension of 20 mm.

25. A cap and vial assembly comprising the cap assembly of claim 14 and a vial, the cap assembly being coupled to the vial.

26. 26. The cap and vial assembly of claim 25, wherein the vial has a volume of 1 mL to 500 mL.

27. 26. The cap and vial assembly of claim 25, wherein the vial comprises glass.

28. 28. The cap and vial assembly of claim 27, wherein the glass comprises borosilicate glass.

29. 26. The cap and vial assembly of claim 25, wherein the vial comprises plastic.

30. 26. The cap and vial assembly of claim 25, wherein the cap and the vial both include threads such that the cap assembly is configured to be coupled to the vial by a screw mechanism.

31. 26. The cap and vial assembly of claim 25, wherein the cap assembly is configured to be coupled to the vial by a crimping mechanism.

32. 26. The cap and vial assembly of claim 25, wherein the cap assembly is configured to be coupled to the vial by a snap mechanism.

33. 32. A method of testing water quality in a sample using an analytical instrument, the sample contained in a container comprising a liner according to any one of claims 1 to 13, a cap assembly according to any one of claims 14 to 24, or a cap and vial assembly according to any one of claims 25 to 32, the method comprising: penetrating the liner with a syringe to remove a portion of the sample; and testing the portion of the sample using the analytical instrument.

34. 34. The method of claim 33, wherein the analytical instrument is a gas chromatograph, a liquid chromatograph, a mass spectrometer, or any combination thereof.

35. 34. The method of claim 33, wherein the method comprises removing one or more portions of the sample by penetrating the liner with the syringe 1 to 20 times.

36. 34. The method of claim 33, wherein the liner is penetrated by the syringe through an automatic sampling device.

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