PHARMACEUTICAL CONTAINERS WITH COATINGS COMPRISING POLYCYANURATES

Abstract

This description relates to pharmaceutical containers that include a coating comprising polycyanurate, and to methods for producing them; in one or more embodiments of this description, a pharmaceutical container may comprise a glass container comprising a first surface and a second surface opposite the first surface; the first surface may be an outer surface of the glass container; the pharmaceutical container may also comprise a coating positioned over at least a portion of the first surface of the glass container; the coating may comprise polycyanurate.

Description

PHARMACEUTICAL CONTAINERS WITH LININGS COMPRISING POLICIANO RATOS CROSS REFERENCE TO RELATED APPLICATIONS This application claims the benefit of priority under 35 USC§ 120 of the US Provisional Application serial number 62 / 884,731 filed on August 9, 2019, the contents of which are referenced and incorporated herein by reference in their entirety. FIELD OF INVENTION This description refers generally to glass articles and, more specifically, to coatings on glass articles, such as pharmaceutical containers. BACKGROUND OF THE INVENTION Historically, glass has been the preferred material for packaging pharmaceuticals due to its airtightness, optical clarity, and superior chemical durability compared to other materials. Specifically, glass used in pharmaceutical packaging should have adequate chemical durability to avoid compromising the stability of the pharmaceutical compositions it contains. Glass with suitable chemical durability for many pharmaceutical applications includes glass compositions that meet the ASTM Type IB standard, which have a proven track record of chemical resistance. However, the use of glass for such applications is limited by its mechanical performance. In the pharmaceutical industry, glass breakage is a safety concern for the end user, as broken containers and / or their contents can cause injury. Glass containers on the filling line also represent costly drug losses or even potential product recalls due to defective or broken glass contained within sealed containers. Furthermore, non-catastrophic breakage (i.e., when the glass cracks but does not shatter) can cause the contents to lose their sterility, which, in turn, can result in costly product recalls. Specifically, the high processing speeds used in the manufacture and filling of glass pharmaceutical containers can result in mechanical damage to the container surface, such as abrasions, as the containers come into contact with processing equipment, handling equipment, and / or other containers. This mechanical damage significantly reduces the strength of the glass pharmaceutical container, resulting in a ML / t / ZUZZ / UÓ IZ / + increased probability of cracks developing in the glass, potentially compromising the sterility of the pharmaceutical product contained in the package or causing total failure of the package. One approach to improving the mechanical durability of glass containers is chemical and / or thermal tempering. Thermal tempering strengthens glass by inducing a surface compressive force during rapid cooling after forming. This technique works well for glass articles with flat geometries (such as windows), glass articles with thicknesses greater than approximately 2 mm, and glass compositions with high thermal expansion. However, pharmaceutical glass containers typically have complex geometries (bottles, tubes, ampoules, etc.), thin walls (sometimes between approximately 1 and 1.5 mm), and are produced from low-expansion glass, making them unsuitable for reinforcement by conventional thermal tempering. Chemical tempering also strengthens glass by introducing surface compressive force.The stress is introduced by immersing the item in a molten salt bath. As the glass ions are replaced by larger molten salt ions, a compressive force is induced on the glass surface. The advantage of chemical tempering is that it can be used on complex geometries, thin samples, and is relatively insensitive to the thermal expansion characteristics of the glass substrate. However, while the aforementioned tempering techniques improve the ability of reinforced glass to withstand blunt impacts, these techniques are less effective at improving the glass's resistance to abrasions, such as scratches, that can occur during manufacturing, transport, and handling. Such defects can make the glass more susceptible to breakage. Therefore, there is a need for alternative glass articles that have improved resistance to mechanical damage. BRIEF DESCRIPTION OF THE INVENTION In one or more embodiments of the present description, a pharmaceutical container may comprise a glass container comprising a first surface and a second surface opposite the first surface. The first surface may be an outer surface of the glass container. The pharmaceutical container may also comprise a coating positioned over at least a portion of the first surface of the glass container. The coating may comprise polycyanurate. In one or more additional forms of the present description, a container A pharmaceutical container may comprise a glass container comprising a first surface and a second surface opposite the first surface. The first surface may be an outer surface of the glass container. The pharmaceutical container may also comprise a coating positioned on at least a portion of the first surface of the glass container. The coating may comprise a polymer formed from at least one or more cyanate ester monomers. In further embodiments of the present description, a coated pharmaceutical container may be produced by a method that may comprise depositing a coating precursor mixture onto a first surface of the outer surface of a glass container, and heating the coating precursor mixture to form a coating on the outer surface of the glass container. The coating precursor mixture may comprise one or more cyanate esters, and the coating may comprise polycyanurate. Additional features and advantages of the coatings that can be used to coat glass articles, coated glass articles, and the methods and procedures for manufacturing them will be set forth in the following detailed description, and will be in part readily apparent to those skilled in the art from that description or recognized by practicing the methods described herein, including the following detailed description, the claims, and the accompanying drawings. It is understood that both the preceding general description and the following detailed description describe various embodiments and are intended to provide a general overview or framework for understanding the nature and character of the claimed subject matter. The accompanying drawings are included to provide a further understanding of the various embodiments and are incorporated into and form part of this specification. The drawings illustrate the various embodiments described herein and, together with the description, serve to explain the principles and operations of the claimed subject matter. BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 schematically represents a cross-sectional view of a glass container with a low-friction coating, according to one or more of the modalities shown and described herein; Figure 2 schematically represents an enlarged cross-sectional view of the glass container of Figure 1 with a single-layer low-friction coating, according to one or more of the modalities shown and described herein; ML / t / ZUZZ / UÓ IZ / 4 Figure 3 schematically represents a positioning template for tests to determine the coefficient of friction between two surfaces, according to one or more of the modalities shown and described herein; and Figure 4 plots transmission percentage data for the Example 2 samples against the wavelength of light, according to one or more of the modes shown and described herein. DETAILED DESCRIPTION OF THE INVENTION Reference will now be made in detail to various types of coatings, coated glassware, and methods for producing them, examples of which are illustrated schematically in the figures. Such coated glassware may be glass containers suitable for use in various packaging applications, including, but not limited to, pharmaceutical packaging. It should be understood that coated glassware may refer to coated pharmaceutical containers as described herein. In one or more embodiments, the coatings and / or coated pharmaceutical containers are thermally stable when, after the initial coating application and curing, they are exposed to high temperatures, such as those used during a depyrogenation procedure.For example, the coated glass articles described herein may sufficiently retain their low coefficient of friction after heat treatment and / or may not be substantially yellow in color after such heat treatment. These pharmaceutical containers may or may not contain a pharmaceutical composition. In one or more embodiments, the coatings may comprise one or more polycyanurates. In some embodiments, the entire body may be made of polycyanurate. In one or more embodiments, the coatings may be low-friction coatings, such as those having a coefficient of friction that is less than that of glass alone, such as less than 0.7. In one or more of the embodiments described herein, the coatings that include polycyanurate may have desirable functionality and / or properties compared to other polymer materials that may be available for coatings in pharmaceutical containers.For example, coatings comprising or consisting of polycyanurate can provide a reduced coefficient of friction, improved adhesion without the use of a silane coupling agent, and / or solubility in non-toxic solvents during application, compared to coatings made from other classes of polymers. Various types of coatings, coated glass articles, and methods for forming them will be described in more detail herein with specific reference to the accompanying drawings. Although the types of coatings described in the ML / t / ZUZZ / UÓ IZ / 4 present are applied to the outer surface of a glass container, it should be understood that the described coatings can be used as a coating on a wide variety of materials, including non-glass materials and on substrates other than containers including, without limitation, glass display panels and the like. Generally, a coating can be applied to the surface of a glass item, such as a container used for pharmaceutical packaging. The coating can provide advantageous properties to the coated glass item, such as a reduced coefficient of friction and increased resistance to damage. The reduced coefficient of friction can impart improved strength and durability to the glass item by mitigating frictional damage. Furthermore, the coating can maintain these enhanced strength and durability characteristics after exposure to elevated temperatures and other conditions, such as those experienced during the packaging and pre-packaging steps used in pharmaceutical packaging, including depyrogenation, freeze-drying, autoclave sterilization, and similar processes.Therefore, coatings and glass articles with the coating can be thermally stable under conditions such as those used in depyrogenation. Figure 1 schematically represents a cross-section of a coated glass article, specifically a coated glass container 100. The coated glass container 100 comprises a glass body 102 and a coating 120. The glass body 102 has a glass container wall 104 extending between an outer surface 108 (i.e., a first surface) and an inner surface 110 (i.e., a second surface). The inner surface 110 of the glass container wall 104 defines an inner volume 106 of the coated glass container 100. A coating 120 is positioned on at least a portion of the outer surface 108 of the glass body 102. As used herein, a coating may be positioned on a substrate while not in direct contact with the substrate, such as if an intermediate layer is present between the substrate and a coating positioned on that substrate.In some embodiments, the coating 120 may be positioned over substantially the entire outer surface 108 of the glass body 102. In some embodiments, as illustrated in Figure 1, the coating 120 may be in direct contact with (for example, bonded to) the glass body 102 on the outer surface 108. The coating 120 has an outer surface 122 and a glass body contact surface 124 at the interface of the glass body 102 and the coating 120. In one or more forms, the coated glass container 100 is a pharmaceutical container. For example, the glass body 102 may be in the form of a jar, ampoule, vial, bottle, flask, or reliquary. ML / t / ZUZZ / UÓ IZ / 4 Beaker-shaped, bucket-shaped, carboy-shaped, container-shaped, syringe-body-shaped, or similar. The coated glass container 100 can be used to contain any composition, and in one embodiment, it can be used to contain a pharmaceutical composition. A pharmaceutical composition can include any chemical substance intended for use in medical diagnosis, cure, treatment, or prevention of disease. Examples of pharmaceutical compositions include, but are not limited to, medicines, drugs, medications, remedies, and the like. The pharmaceutical composition can be in the form of a liquid, a solid, a gel, a suspension, a powder, or the like. Referring now to Figures 1 and 2, in one embodiment, the coating 120 comprises a single-layer structure, sometimes referred to herein as a monolayer structure. For example, the coating 120 may have a substantially homogeneous composition of polycyanurate alone, or polycyanurate mixed with one or more additional components. If two or more components are included in the coating 120, the coating 120 may be mixed but not completely homogeneous. For example, in one or more embodiments, one or more chemical constituents of the mixture may congregate at an interface of the coating 120 (e.g., the interface with the glass body 102 or the external surface 122). In such an embodiment, the local concentration of a constituent may differ over different areas of the coating 120.However, it should be understood that the term "mixed" as used herein refers to coatings that have at least some dispersion of at least two chemical components and includes coatings that are not completely homogeneous. In general, a mixed coating is deposited as a mixture of two or more chemical constituents contained in a precursor coating mixture. As noted herein, Coating 120 includes one or more polycyanurates. In general, polycyanurates are thermally stable polymers that will not degrade significantly, or at all, when exposed to temperatures suitable for depyrogenation, such as at least approximately 250°C, at least approximately 260°C, at least approximately 280°C, or even at least approximately 300°C for approximately 30 minutes. The polycyanurates, as described herein, include polymers formed from cyanate ester monomers. In additional embodiments, the polycyanurate may be formed from prepolymers that include cyanate ester monomers. Prepolymers refers to substantially partially polymerized polymers that are further polymerized to form the polycyanurate in Coating 120.Polycyanurates, as described herein, also include polymers with main polycyanurate structures that are modified by other chemical constituents, or copolymers. Polycyanurates include one or more cyanate ester monomeric units along with other non-cyanate ester monomers. For example, polycyanurate can be a homopolymer formed from a single cyanate ester species as monomeric units, copolymers (either random or block) formed from two or more cyanate ester species, or copolymers that include some polycyanurate main structure while additionally including another monomeric species, as described herein. Polycyanurate can be formed by polymerization means, such as heat curing or other methods, using monomers or prepolymers, or a combination thereof. Coating 120 may comprise at least 10% by weight, at least 20% by weight, at least 30% by weight, at least 40% by weight, at least 50% by weight, at least 60% by weight, at least 70% by weight, at least 80% by weight, at least 90% by weight, at least 95% by weight, at least 98% by weight, at least 99% by weight, or even at least 99.9% by weight of polycyanurate. The polycyanurate in coating 120 may comprise at least 10% by weight, at least 20% by weight, at least 30% by weight, at least 40% by weight, at least 50% by weight, at least 60% by weight, at least 70% by weight, at least 80% by weight, at least 90% by weight, at least 95% by weight, at least 98% by weight, at least 99% by weight, or even at least 99.9% by weight of cyanate ester-derived components.The coating portion derived from any individual species of cyanate ester may be at least 10% by weight, at least 20% by weight, at least 30% by weight, at least 40% by weight, at least 50% by weight, at least 60% by weight, at least 70% by weight, at least 80% by weight, at least 90% by weight, at least 95% by weight, at least 98% by weight, at least 99% by weight, or even at least 99.9% by weight of the total weight of the polycyanurate. In some embodiments of the present description, the polycyanurate may comprise a 3-dimensional cross-linked structure, wherein the -OCN functional groups of the cyanate ester monomers form triazine rings. The polycyanurate may comprise monomeric units formed from one or more cyanate esters. A generalized chemical structure of a cyanate ester, which can be used to form the polycyanurate, is represented in Chemical Structure 1. As represented, the cyanate ester comprises -OCN functionalities (as two -OCN functionalities linked by an R group). ML / t / ZUZZ / UÓ IZ / + Chemical structure 1: OΞN GOLD N = C In some embodiments of the present description, the R group is not necessarily limited. However, in some embodiments, the cyanate ester used may comprise bisphenol functionality, referred to herein as a bisphenol cyanate ester. Bisphenols generally refer to chemical compounds comprising two phenol groups, each of which includes an oxygen atom directly bonded to a phenol group. Such bisphenol functionality can provide good heat resistance. Tables 1 and 2 provide examples of the bisphenol cyanate esters considered, which may be included in the polycyanurate.For example, the cyanate esters used to form polycyanurate can be selected from bisphenol A cyanate ester, bisphenol E cyanate ester, C,C'-((2,2,2-trifluoro-1-(trifluoromethyl)ethylene)d1-4,1-phenylene) ester (sometimes known as hexafluorobisphenol A cyanate ester), tetramethylbisphenol F cyanate ester, bisphenol M cyanate ester, C,C'-((2,2,2-trifluoro-1-(trifluoromethyl)ethylene)d1-4,1-phenylene) ester, or combinations thereof. However, as will be understood, other types of cyanate can be used, and therefore Tables 1 and 2 are only examples of possible cyanate esters. Cyanate esters can include heteroatoms such as, but not limited to, Si, P and / or F. Additionally, aromatic dicyanate esters with phenylphosphine oxide, sulfone and carbonyl groups are being considered for use, as they can have good reactivity and thermal performance.Additionally, cyanate esters, such as those containing novolac or polystyrene, are contemplated for use in the embodiments described herein. It should be understood that prepolymers that can be used to form polycyanurate may include such cyanate esters as monomeric units. MA / t / ZUZZ / UÓ IZ / 4 TABLE 1 Structure Name Molecular Weight (g / mol) Bisphenol A Cyanate Ester 278.31 Bisphenol E Cyanate Ester 264.28 Hexafluorobisphenol A Cyanate Ester 386.25 Tetramethylbisphenol F Cyanate Ester 306.36 Bisphenol M Cyanate Ester 396.49 MA / t / ZUZZ / UÓ IZ / 4 TABLE 2 Structure Name Short Name Bisphenol A Cyanate Ester DCBA C,C'-[(dimethylsilylene)d-4,1-phenylene] ester Si-DCBA C,C'-((2,2,2-trifluoro-1(trifluoromethyl)ethylene)d-4,1-phenylene] ester F-DCBA According to additional embodiments, the polycyanurate may be formed from one or more cyanate esters described herein in Chemical Structures 2 to 56. The cyanate esters described in Chemical Structures 2 to 56 may include, but are not limited to, tris(cyanate phenoxy)phosphazene, poly(phenyl)phenylene dicyanate, polyarylene ether ketone (PEK) dicyanate, polyether sulfone (PES) dicyanate, poly(cyanate phenyl maleimide), poly(4-cyanatophenyl styrene), poly(4-cyanatophenyl styrene)-co-MMA, poly(4-cyanatophenyl styrene)-co-BD, bis(3-allyl-4-cyanatophenyl)propane, bis(3-propenyl-4-cyanatophenyl)propane, 4-cyanatophenyl, 4-cyanate benzoate, and 4,4'-dicyanate biphenyl. As can be understood, polycyanurate can be formed from a single cyanate ester composition or from multiple cyanate ester compositions, such as those in Chemical Structures 2 to 56. ML / t / ZUZZ / UÓ IZ / 4 Chemical structure 2: Chemical structure 4: Chemical structure 5: Chemical structure 6: Chemical structure 7: ML / t / ZUZZ / UÓ IZ / + Chemical structure 8: Chemical structure 9: Chemical structure 10: Chemical structure 11: Chemical structure 12: Chemical structure 13: ML / t / ZUZZ / UÓ IZ / 4 NCO' Chemical structure 14: 5 Chemical structure 15: Chemical structure 16: Chemical structure 17: 10 Chemical structure 18: NCO - im NCO^^ \ 4 λ—OCN Chemical structure 19: Chemical structure 22: ML / t / ZUZZ / UÓ IZ ! + Chemical structure 23: Chemical structure 24: Chemical structure 25: Chemical structure 26: Chemical structure 27: Chemical structure 28: OCN ML / t / ZUZZ / UÓ IZ / + Chemical structure 29: Chemical structure 30: Chemical structure 31: Chemical structure 32: Chemical structure 34: OCN D1 / D2 ML / t / ZUZZ / UÓ IZ / 4 Chemical structure 35: Chemical structure 36: Chemical structure 37: Chemical structure 38: NCO Chemical structure 39: OCN Chemical structure 40: ML / t / ZUZZ / UÓ IZ / 4 Chemical structure 43: NCO OCN Chemical structure 44: Chemical structure 45: NCO OCN ML / t / ZUZZ / UÓ IZ / + Chemical structure 46: NCO OCN ML / t / ZUZZ / UÓ IZ / 4 Chemical structure 47: OCN Chemical structure 48: Chemical structure 49: CH, Chemical structure 52: ch3 H3C\I NCO·^^^ Chemical structure 53: h3c^ 5 Chemical structure 54: FFFF nco. yy FF 10 Chemical structure 55: °yy^ ^OCIAn^ '-^'OCN CHj __ Va qa°cn FFFF oA-° Acó ML / IZ / ZUZZ / UO1 Z l + Chemical structure 56: ML / t / ZUZZ / UÓ IZ l + In one or more ways, cyanate esters can be synthesized from phenols and cyanogen halides in the presence of a tertiary amine at low temperatures. The following chemical equation A represents one such reaction. Chemical Equation A: / =\ (C2H5)3N / =\ r—ά )—oh + CNBr---------*· r—ά ύ—ocn + (CzHshNHBr / THF,, Acetone \ / -5to30C According to methods described herein, polycyanurate can be formed by curing (e.g., by heat) cyanate esters. The heating required for curing can be relatively mild, such as less than 230°C. A generalized curing reaction for forming polycyanurate from cyanate esters is represented in Chemical Equation B below. During the curing process, triazine rings are formed by the cyclotrimerization of three cyanate ester groups (-OCN) to produce a highly cross-linked polycyanurate polymer network. Generally, the reaction does not produce any byproducts. Additionally, the reaction does not release a toxic compound such as HCN, which can be harmful to the environment and / or people who come into contact with such a substance. Therefore, the cyclotrimerization of cyanate esters, as shown in Chemical Equation B, can be classified in the categories of green chemistry and click chemistry.For example, the curing process does not produce water, as occurs in some other polymerization reactions. In additional formulations, this curing process may be less corrosive to processing equipment and / or may exhibit less post-curing shrinkage. Chemical equation B: ML / t / ZUZZ / UÓ IZ / 4 In additional embodiments, polycyanurate can be functionalized with additional reagents, or it can be a polymer formed from a mixture of cyanate ester and other polymers. For example, cyanate esters can react with many other groups or reagents such as water, phenols, epoxies, etc. For instance, cyanate ester can be co-cured with epoxy to form polycyanurate. The co-reaction of cyanate ester and epoxy can result in a product whose water resistance and dielectric properties are improved compared to those of a homopolymer formed from cyanate ester or epoxy. Such cocured polycyanurates are described in 1 Bauer & M. Bauer (1990) Kinetic Structural Model for the Network Build-Up During the Reaction of Cyanic Acid Esters with Glycidyl Ethers, Journal of Macromolecular Science: Part A - Chemistry, 27:1, 97-116 and Shimp, DA, HF, Ising SJ. , Koreaaction of epoxide and cyanate resins.33rd Int SAMPE Symp 1988, 33, 754-766, the teachings of both are incorporated herein by reference. Cyanate esters can be co-cured or blended with other types of monomers, such as epoxides, phenols, amides, alkenes, and acrylates, to form interpenetrating networks (IPNs) or semi-IPNs, to further modify film properties and curing kinetics. According to additional formulations, cyanate esters can be comixed with bismaleimide (BMI). This mixture can combine the good mechanical properties of cyanate esters with the good heat resistance of BMI. In addition to BMI, BMI derivatives can also be used as a comixture to modify cyanate esters and improve their performance. In one embodiment, the coating 120 can be applied as an uncured coating precursor mixture and subsequently cured. The coating precursor mixture refers to the liquid solution containing cyanate esters or other precursors of the cured polycyanurate material that is applied to the glass body 102. In some embodiments, the coating precursor mixture will include one or more organic solvents along with the polymer precursor (e.g., cyanate ester). The coating precursor mixture may include one or more chemical constituents containing material that will become a constituent in the coating 120 after application and curing of the coated glass container 100 (e.g., by spray or dip coating, followed by heating). That is, at least some of the precursor atoms will be converted into atoms of the resulting coating.In additional modalities, prepolymers or even fully polymerized polycyanurate can be included in the precursor coating mixture. Referring again to Figures 1 and 2, Coating 120 can be applied in a single deposition step, where the Coating 120 comprises a single layer. Deposition can be by immersion or, alternatively, Coating 120 can be applied by a sprayer or other suitable means and optionally dried. A description of deposition methods appropriate for the Coatings 120 described herein can be found in U.S. Patent Application No. 13 / 780,740, entitled "Glass Articles with Low-Friction Coatings," which is incorporated herein by reference in its entirety. In further embodiments, multiple depositions can be used. For example, multiple depositions of the coating precursor mixture can be carried out and then cured, or curing can follow each deposition step, such that a second precursor coating is applied to a cured layer.As you can understand, the deposition technique may depend on the geometry of the glass article. After deposition of the coating precursor mixture, at least a portion of the organic solvent is released from the coating precursor mixture, either by passive drying or by active drying step(s), such as controlled airflow or increased temperatures. The coated glass containers 100 can then be cured by exposure to heat. As described herein, curing refers to any procedure (usually by heating) that changes the material in the coating from the precursor material to an intermediate or final material. For example, some embodiments use heat curing, which releases constituents from the metal oxide precursor and forms the metal oxide. Such curing may comprise heating the coated bottle to a temperature sufficient to polymerize the polycyanurate, such as 200°C to 230°C.Curing conditions may depend on the type of precursor materials used. Without intending to support any particular theory, it is believed that the curing step releases any remaining solvent from the coating precursor mixture. ML / t / ZUZZ / UÓ IZ / 4 The coating 120 applied to the glass body 102 can have a thickness of less than or equal to approximately 100 pm, less than or equal to approximately 10 pm, less than or equal to approximately 8 pm, less than or equal to approximately 6 pm, less than or equal to approximately 4 pm, less than or equal to approximately 3 pm, less than or equal to approximately 2 pm, or even less than or equal to approximately 1 pm. In some embodiments, the thickness of the coating 120 can be less than or equal to approximately 800 nm, less than or equal to approximately 600 nm, less than or equal to approximately 400 nm, less than or equal to approximately 300 nm, less than or equal to approximately 200 nm, or even less than or equal to approximately 100 nm thick.In other embodiments, the 120 coating may be less than approximately 90 nm thick, less than approximately 80 nm thick, less than approximately 70 nm thick, less than approximately 60 nm thick, less than approximately 50 nm thick, or even less than approximately 25 nm thick. In some embodiments, the 120 coating may have a thickness of at least approximately 10 nm, at least approximately 15 nm, at least approximately 20 nm, at least approximately 25 nm, at least approximately 30 nm, at least approximately 35 nm, at least approximately 40 nm, or even at least approximately 45 nm. Exemplary embodiments may have a thickness from approximately 20 nm to approximately 50 nm, from approximately 25 nm to approximately 45 nm, or from approximately 30 nm to approximately 40 nm.While not limited by theory, it is believed that relatively thin coatings (i.e., less than 20 nm) may not adequately protect the glass, resulting in cracking of the glass surface during bottle-to-bottle contact. Furthermore, such relatively thin coatings may not survive a depyrogenation process. On the other hand, relatively thick coatings (i.e., greater than 50 nm) can be easily damaged, and wear marks may appear on the coating due to bottle-to-bottle contact. It should be noted that in the case of relatively thick coatings, the wear marks are believed to be deformations in the coating and not in the glass. As described herein, wear marks are visible traces caused by abrasion on a coating, leaving a worn area or mark.In some models, signs of wear may indicate cracking of the glass and / or a relatively high coefficient of friction (e.g., 0.7 or higher). In some embodiments, the coating 120 may not be of uniform thickness over the entire glass body 102. For example, the coated glass container 100 may have a thicker coating 120 in some areas, due to the procedure of contacting the glass body 102 with one or more coating solutions that form the coating 120. In some embodiments, the coating 120 may not have a uniform thickness. For example, the coating thickness may vary over different regions of a coated glass container. ML / t / ZUZZ / UÓ IZ / + 100, which can promote protection in a selected region. Several non-limiting advantages of the polycyanurate coatings described herein can be observed compared to other polymer-based coatings for pharmaceutical packaging. One such advantage is a reduced coefficient of friction. For example, a coefficient of friction of less than 0.2, and approximately 0.1, has been observed in the embodiments described herein. Additionally, or alternatively, cyanate esters can provide improved adhesion to the glass surface due to stronger physical interactions and chemical reactions between the cyanate ester and the silanol on the glass surface. In contrast, polyimide coatings may require aminofunctionalized alkoxysilane as a coupling agent to improve coating adhesion, which adds cost and processing difficulties.Additionally or alternatively, cyanate esters, especially F-DCBA, and their prepolymers are readily soluble in various environmentally benign organic solvents with low boiling points, whereas precursors of other coating systems, such as polyimide coatings, may need to be dissolved in solvents with very high boiling points, such as Novastrat 800 polyamic acid in toluene / DMF, and PMDA-ODA (poly(4,4'-oxyphenylene-promelimide) in NMP. In additional modalities, the crosslinking reaction of cyanate esters to form polycyanurates can be classified as 'click chemistry,' which produces no byproducts and requires no additional reagents to facilitate the formation of crosslinked products, triazine rings. This can be a substantial advantage compared to crosslinking methodologies based on polycondensations, such as imide polymerization and silane curing in glass. Generally, polycondensation forms H₂O, while silane curing can release MeOH or EtOH. These byproducts can impede the polymerization / curing ratio because they shift the chemical equilibrium back towards the starting materials. An additional advantage is that polycyanurate coating precursors, cyanate esters, and oligomeric triazines (as in polycyanurate prepolymers) are readily soluble in commonly used, environmentally friendly solvents such as ketones, esters, and ethers. In comparison, high-temperature thermal plastics such as PEEK and PPSU are more difficult to dissolve in solvents at medium temperatures and are therefore not suitable for solution-based thin-film coating procedures. In addition to or as an alternative to other methods described herein, coatings comprising polycyanurate can be substantially clear for a film thickness of up to 1 micron. This provides a relatively wide processing window if transparency is desired. ML / t / ZUZZ / UÓ IZ / 4 In additional embodiments, the coatings 120 described herein, which include polycyanurate, can be an amorphous material due to their triazine ring functionalities formed during the thermal curing process. This can provide the coating 120 with good anisotropic behavior in terms of physical and chemical properties, as well as good post-curing dimensional stability. The glass containers for pharmaceutical packaging, to which coating 120 can be applied, can be formed from a variety of different glass compositions. The specific composition of the glass article can be selected according to the specific application so that the glass has a desired set of physical properties. In one or more embodiments, the glass can be a composition known to exhibit chemical durability and low thermal expansion, such as alkali borosilicate glass. In another embodiment, the glass container can be formed from Type I, Class B glass in accordance with ASTM E438-92. The glass containers can be formed from a glass composition having a coefficient of thermal expansion in the range of approximately 25 x 10⁻⁷ / °C to 80 x 10⁻⁷ / °C. For example, in some embodiments described herein, the glass body 102 is formed from alkali aluminosilicate glass compositions that are susceptible to ion-exchange strengthening. Such compositions generally include a combination of SiO₂, Al₂O₃, at least one alkaline earth oxide, and one or more alkali oxides, such as Na₂O and / or K₂O. In some of these embodiments, the glass composition may be free of boron and boron-containing compounds. In some other embodiments, the glass compositions may further comprise minor amounts of one or more additional oxides, such as SnO₂, ZrO₂, ZnO, TiO₂, As₂O₃, or the like.These components may be added as clarifying agents and / or to further increase the chemical durability of the glass composition. In another embodiment, the glass surface may comprise a metal oxide coating comprising SnO2, ZrO2, ZnO, TiO2, As2Oa, or similar. In some embodiments described herein, the glass body 102 is reinforced by ion-exchange reinforcement, hereinafter referred to as ion-exchange glass. For example, the glass body 102 may have a compressive strength greater than or equal to approximately 300 MPa or even greater than or equal to approximately 350 MPa. In some embodiments, the compressive strength may be in the range of approximately 300 MPa to approximately 900 MPa. However, it should be understood that, in some embodiments, the compressive strength in the glass may be less than 300 MPa or greater than 900 MPa. In some embodiments, the glass body 102 may have a layer depth greater than or equal to 20 pm. In some of these embodiments, the layer depth may be greater than 50 pm or ML / t / ZUZZ / UÓ IZ / 4 even greater than or equal to 75 pm. In still other embodiments, the coating depth can be up to or greater than 100 pm. The ion exchange strengthening can be carried out in a molten salt bath maintained at temperatures of approximately 350 °C to approximately 500 °C. To achieve the desired compressive strength, the (uncoated) glass container can be immersed in the salt bath for less than approximately 30 hours or even less than approximately 20 hours. For example, in one embodiment, the glass container is immersed in a 100% KNO3 salt bath at 450 °C for approximately 8 hours. In one particularly exemplary embodiment, the 102 glass body can be formed from an exchangeable ion glass composition described in pending U.S. Patent Application Serial No. 13 / 660894 filed October 25, 2012, and entitled Glass Compositions with Improved Chemical and Mechanical Durability assigned to Corning, Incorporated. However, as can be understood, the coated glass containers 100 described herein can be formed from other glass compositions, including, without limitation, ion-exchange glass compositions and non-ion-exchange glass compositions. For example, in some embodiments, the glass container can be formed from Type IB glass compositions such as, for example, Schott Type IB borosilicate glass. In some of the forms described herein, the glass article may be formed from a glass composition that meets the criteria for pharmaceutical-grade glass as described by regulatory agencies such as the USP (United States Pharmacopeia), the EP (European Pharmacopoeia), and the JP (Japanese Pharmacopoeia) based on its hydrolytic resistance. According to USP 660 and EP 7, borosilicate glass meets Type 1 criteria and is routinely used for parenteral packaging. Examples of borosilicate glass include, but are not limited to, Corning® Pyrex® 7740, 7800 and Wheaton 180, 200, and 400, Schott Duran, Schott Fiolax, KIMAX® N-51A, Gerrescheimer GX-51 Flint, and others. Soda-lime glass meets Type III criteria and is acceptable in the packaging of dry powders that are subsequently dissolved to form solutions or buffers.Type III glasses are also suitable for packaging liquid formulations that are proven to be alkali-insensitive. Examples of Type III soda-lime glass include Wheaton 800 and 900. Dealkalized soda-lime glasses have higher levels of sodium hydroxide and calcium oxide and meet Type II criteria. These glasses are less resistant to leaching than Type I glasses but more resistant than Type III glasses. Type II glasses can be used for products that remain below a pH of 7 throughout their shelf life. Examples include soda-lime glasses treated with ammonium sulfate. These pharmaceutical glasses have varied chemical compositions and a coefficient of linear thermal expansion (CTE) on the scale of 20–85 x 10⁻⁷ / °C. When the coated glass articles described herein are containers ML / t / ZUZZ / UÓ IZ ! + of glass, the glass body 102 of the coated glass containers 100 can take a variety of different forms. For example, the glass bodies described herein can be used to form coated glass containers 100 such as flasks, ampoules, cartridges, syringe bodies, and / or any other glass container for storing pharmaceutical compositions. In addition, the ability to chemically strengthen the glass containers prior to coating can be used to further improve the mechanical durability of the glass containers. Accordingly, it should be understood that, in at least one embodiment, the glass containers can be strengthened by ion exchange prior to the application of the coating. Alternatively, other strengthening methods such as heat tempering, flame polishing, and lamination, as described in U.S. Patent No.7,201,965 could be used to reinforce the glass before coating. Several properties of coated glass containers (i.e., coefficient of friction, horizontal compression strength, 4-point bending strength) can be measured when the coated glass containers are in a coated condition (i.e., after application of the coating without any additional treatment other than curing if applicable) or after one or more processing treatments, such as those similar or identical to the treatments performed on a pharmaceutical product filling line, including, without limitation, washing, freeze-drying, depyrogenation, autoclave sterilization, or the like. Depyrogenation is a process in which pyrogens are removed from a substance. The depyrogenation of glass articles, such as pharmaceutical containers, can be carried out by heat treatment applied to a sample, in which the sample is heated to an elevated temperature for a period of time. For example, depyrogenation may involve heating a glass container to a temperature between approximately 250 °C and approximately 380 °C for a period of approximately 30 seconds to approximately 72 hours, including, but not limited to, 20 minutes, 30 minutes, 40 minutes, 1 hour, 2 hours, 4 hours, 8 hours, 12 hours, 24 hours, 48 ​​hours, and 72 hours. After the heat treatment, the glass container is cooled to room temperature. A conventional depyrogenation condition commonly used in the pharmaceutical industry is heat treatment at a temperature of approximately 250 °C for approximately 30 minutes.However, it is understood that the heat treatment time can be reduced by using higher temperatures. Coated glass containers, as described herein, can be exposed to elevated temperatures for a period of time. The elevated temperatures and heating times described herein may or may not be sufficient to depyrogenate a glass container. However, it should be understood that some of the temperatures and heating times described herein are sufficient to... ML / t / ZUZZ / UÓ IZ / 4 to depyrogenate a coated glass container, such as the coated glass containers described herein. For example, as described herein, the coated glass containers may be exposed to temperatures of approximately 250 °C, approximately 260 °C, approximately 270 °C, approximately 280 °C, approximately 290 °C, approximately 300 °C, approximately 310 °C, approximately 320 °C, approximately 330 °C, approximately 340 °C, approximately 350 °C, approximately 360 °C, approximately 370 °C, approximately 380 °C, approximately 390 °C, or approximately 400 °C, for a period of 30 minutes.It is recognized that depyrogenation processes may have different times than 30 minutes, and 30 minutes is used throughout this description with a depyrogenation temperature for comparative purposes such as, for example, coefficient of friction testing after exposure to a defined depyrogenation condition. As used herein, lyophilization conditions (i.e., freeze-drying) refer to a procedure in which a sample is filled with a protein-containing liquid and then frozen at low temperatures, such as -100°C, followed by water sublimation for a time such as 20 hours at temperatures such as -15°C under vacuum. As used herein, autoclave conditions refer to purging a sample with steam for a period of time such as 10 minutes at 100°C, followed by a 20-minute resting period where the sample is exposed to an environment of 121°C, followed by 30 minutes of heat treatment at 121°C. The coefficient of friction (μ) of the coated portion of the glass container may be lower than that of an uncoated glass container made of the same glass composition. A coefficient of friction (μ) is a quantitative measure of the friction between two surfaces and is a function of the mechanical and chemical properties of the first and second surfaces, including surface roughness, as well as environmental conditions such as, but not limited to, temperature and humidity. As used herein, a measurement of the coefficient of friction for a coated glass container is reported as the coefficient of friction between the outer surface of a first glass container (having an outside diameter of between approximately 16.00 mm and approximately 17.00 mm).00 mm) and the external surface of the second glass container, which is substantially identical to the first glass container, wherein the first and second glass containers have the same body and the same coating composition (when applied) and have been exposed to the same environments before, during, and after manufacturing. Unless otherwise denoted herein, the coefficient of friction refers to the maximum coefficient of friction measured under a normal load of 30 N. ML / t / ZUZZ / UÓ IZ ! + a bottle-on-bottle test positioning template, as described herein. However, it should be understood that a coated glass container that exhibits a maximum coefficient of friction at a specific applied load will also exhibit the same or better (i.e., lower) maximum coefficient of friction at a lower load. For example, if a coated glass container exhibits a coefficient of friction of 0.5 or less under an applied load of 50 N, the coated glass container will also exhibit a maximum coefficient of friction of 0.5 or less under an applied load of 25 N. To measure a maximum coefficient of friction, local maximums at or near the start of the test are excluded, as maximums at or near the start of the test represent static coefficient of friction.As described in the modalities herein, the coefficient of friction was measured where the speed of the containers relative to one another was approximately 0.67 mm / s. In the embodiments described herein, the coefficient of friction of the glass containers (both coated and uncoated) is measured using a bottle-on-bottle test positioning jig. The test positioning jig 200 is shown schematically in Figure 3. The same apparatus can also be used to measure the frictional force between two glass containers positioned on the positioning jig. The bottle-on-bottle test positioning jig 200 comprises a first clamp 212 and a second clamp 222 arranged in a transverse configuration (i.e., perpendicular to each other). The first clamp 212 comprises a first fixing arm 214 attached to a first base 216. The first fixing arm 214 connects the first glass container 210 and holds the first glass container 210 stationary relative to the first clamp 212.Furthermore, the second clamp 222 comprises a second fixing arm 224 attached to a second base 226. The second fixing arm 224 is attached to the second glass container 220 and holds it stationary with respect to the second clamp 222. The first glass container 210 is positioned in the first clamp 212 and the second glass container 220 is positioned in the second clamp 222 such that the long axis of the first glass container 210 and the long axis of the second glass container 220 are positioned at approximately a 90° angle to each other and in a horizontal plane defined by the xy axis. A first glass container 210 is positioned in contact with the second glass container 220 at a contact point 230. A normal force is applied in a direction orthogonal to the horizontal plane defined by the xy axis. The normal force can be applied by a stationary weight or another force applied to the second clamp 222 on a stationary first clamp 212. For example, a weight can be positioned on the second base 226 and the first base 216 can be placed on a stable surface, thus inducing a measurable force between the first ML / t / ZUZZ / UÓ IZ / 4 glass container 210 and the second glass container 220 at the contact point 230. Alternatively, the force can be applied with a mechanical apparatus, such as a UMT (universal mechanical tester). The first clamp 212 or the second clamp 222 can be moved relative to each other in a direction that is at an angle of 45° to the long axis of the first glass container 210 and the second glass container 220. For example, the first clamp 212 can be held stationary and the second clamp 222 can be moved so that the second glass container 220 moves through the first glass container 210 in the x-axis direction. A similar arrangement is described by RL De Rosa et al., in Scratch Resistant Polyimide Coatings for Alumino Silicate Glass surfaces in The Journal of Adhesion, 78: 113-127, 2002. To measure the coefficient of friction, the force required to move the second clamp 222 and the normal force applied to the first and second glass containers 210, 220 are measured with load cells and the coefficient of friction is calculated as the ratio of the friction force and the normal force.The positioning template is operated in an environment of 25°C and 50% relative humidity. In the embodiments described herein, the portion of the glass container coated with the coating has a coefficient of friction less than or equal to approximately 0.7 relative to a similarly coated glass container, as determined using the bottle-in-bottle positioning template described above. In other embodiments, the coefficient of friction may be less than or equal to approximately 0.6, or even less than or equal to approximately 0.5. In some embodiments, the portion of the glass container coated with the coating has a coefficient of friction less than or equal to approximately 0.4, or even less than or equal to approximately 0.3. Coated glass containers with coefficients of friction less than or equal to approximately 0.7 generally exhibit improved resistance to frictional damage and, as a result, have improved mechanical properties.For example, conventional glass containers (without a coating) can have a coefficient of friction greater than 0.7. In some of the embodiments described herein, the coefficient of friction of the coated portion of the glass container is at least 20% lower than the coefficient of friction of an uncoated glass container surface made of the same glass composition. For example, the coefficient of friction of the coated portion of the glass container may be at least 20% lower, at least 25% lower, at least 30% lower, at least 40% lower, or even at least 50% lower than the coefficient of friction of an uncoated glass container surface made of the same glass composition. ML / t / ZUZZ / UÓ IZ ! + In some embodiments, the portion of the glass container coated with the coating may have a coefficient of friction less than or equal to approximately 0.7 after exposure to a temperature of approximately 250 °C, approximately 260 °C, approximately 270 °C, approximately 280 °C, approximately 290 °C, approximately 300 °C, approximately 310 °C, approximately 320 °C, approximately 330 °C, approximately 340 °C, approximately 350 °C, approximately 360 °C, approximately 370 °C, approximately 380 °C, approximately 390 °C, or approximately 400 °C, for a period of time of 30 minutes. In other embodiments, the portion of the glass container coated with the coating may have a coefficient of friction less than or equal to approximately 0.7, (i.e., less than or equal to approximately 0.6, less than or equal to approximately 0.5, less than or equal to approximately 0.4, or even less than or equal to approximately 0.3) after exposure to a temperature of approximately 250°C, approximately 260°C, approximately 270°C, approximately 280°C, approximately 290°C, approximately 300°C, approximately 310°C, approximately 320°C, approximately 330°C, approximately 340°C, approximately 350°C, approximately 360°C, approximately 370°C, approximately 380°C, approximately 390°C, or approximately 400°C, for a period of 30 minutes. In some embodiments, the coefficient of friction of the coated portion of the glass container may not increase by more than approximately 30% after exposure to a temperature of approximately 250°C (or approximately 260°C) for 30 minutes.In other embodiments, the coefficient of friction of the portion of the glass container coated with the coating may not increase by more than approximately 30% (i.e., approximately 25%, approximately 20%, approximately 15%, or even approximately 10%) after exposure to a temperature of approximately 250°C, approximately 260°C, approximately 270°C, approximately 280°C, approximately 290°C, approximately 300°C, approximately 310°C, approximately 320°C, approximately 330°C, approximately 340°C, approximately 350°C, approximately 360°C, approximately 370°C, approximately 380°C, approximately 390°C, or approximately 400°C, for a period of time of 30 minutes. In other embodiments, the coefficient of friction of the portion of the glass container coated with the coating may not increase by more than approximately 0.5 (i.e., approximately 0.45, approximately 0.4, approximately 0.35, approximately 0.3, approximately 0.25, approximately 0.2, approximately 0.15, approximately 0.1, or even approximately 0.05) after exposure to a temperature of approximately 250 °C, approximately 260 °C, approximately 270 °C, approximately 280 °C, approximately 290 °C, approximately 300 °C, approximately. ML / t / ZUZZ / UÓ IZ / 4 310 °C, approximately 320 °C, approximately 330 °C, approximately 340 °C, approximately 350 °C, approximately 360 °C, approximately 370 °C, approximately 380 °C, approximately 390 °C, or approximately 400 °C, for a period of time of 30 minutes. In some embodiments, the coefficient of friction of the coated portion of the glass container may not increase at all after exposure to a temperature of approximately 250°C, approximately 260°C, approximately 270°C, approximately 280°C, approximately 290°C, approximately 300°C, approximately 310°C, approximately 320°C, approximately 330°C, approximately 340°C, approximately 350°C, approximately 360°C, approximately 370°C, approximately 380°C, approximately 390°C, or approximately 400°C, for a period of time of 30 minutes. In some embodiments, the portion of the glass container coated with the lubricating coating may have a coefficient of friction less than or equal to approximately 0.7 after being immersed in a water bath at a temperature of approximately 70°C for 10 minutes. In other embodiments, the portion of the glass container coated with the coating may have a coefficient of friction less than or equal to approximately 0.7 (i.e., less than or equal to approximately 0.6, less than or equal to approximately 0.5, less than or equal to approximately 0.4, or even less than or equal to approximately 0.3) after being immersed in a water bath at a temperature of approximately 70°C for 5 minutes, 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, or even 1 hour.In some embodiments, the coefficient of friction of the coated portion of the glass container may not increase by more than approximately 30% after being immersed in a water bath at a temperature of approximately 70°C for 10 minutes. In other embodiments, the coefficient of friction of the coated portion of the glass container may not increase by more than approximately 30% (i.e., approximately 25%, approximately 20%, approximately 15%, or even approximately 10%) after being immersed in a water bath at a temperature of approximately 70°C for 5 minutes, 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, or even 1 hour.In some embodiments, the coefficient of friction of the coated portion of the glass container may not increase at all after being immersed in a water bath at a temperature of approximately 70°C for 5 minutes, 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, or even 1 hour. In some embodiments, the portion of the glass container coated with the coating may have a coefficient of friction less than or equal to approximately 0.7 after exposure to freeze-drying conditions. In other embodiments, the portion of the The glass container coated with the coating may have a coefficient of friction less than or equal to approximately 0.7 (i.e., less than or equal to approximately 0.6, less than or equal to approximately 0.5, less than or equal to approximately 0.4, or even less than or equal to approximately 0.3) after exposure to freeze-drying conditions. In some embodiments, the coefficient of friction of the portion of the glass container coated with the coating may not increase by more than approximately 30% after exposure to freeze-drying conditions. In other embodiments, the coefficient of friction of the portion of the glass container coated with the coating may not increase by more than approximately 30% (i.e., approximately 25%, approximately 20%, approximately 15%, or even approximately 10%) after exposure to freeze-drying conditions.In some forms, the coefficient of friction of the portion of the glass container coated with the coating may not increase at all after exposure to freeze-drying conditions. In some embodiments, the coated portion of the glass container may have a coefficient of friction less than or equal to approximately 0.7 after exposure to autoclave sterilization conditions. In other embodiments, the coated portion of the glass container may have a coefficient of friction less than or equal to approximately 0.7 (i.e., less than or equal to approximately 0.6, less than or equal to approximately 0.5, less than or equal to approximately 0.4, or even less than or equal to approximately 0.3) after exposure to autoclave sterilization conditions. In some embodiments, the coefficient of friction of the coated portion of the glass container may not increase by more than approximately 30% after exposure to autoclave sterilization conditions.In other embodiments, the coefficient of friction of the coated portion of the glass container may not increase by more than approximately 30% (i.e., approximately 25%, approximately 20%, approximately 15%, or even approximately 10%) after exposure to autoclave sterilization conditions. In some embodiments, the coefficient of friction of the coated portion of the glass container may not increase at all after exposure to autoclave sterilization conditions. The coated glass containers described herein have a horizontal compressive strength. The horizontal compressive strength, as described herein, is measured by placing the coated glass container 100 horizontally between two parallel rollers that are oriented parallel to the long axis of the glass container. A mechanical load is then applied to the coated glass container 100 with the rollers in the direction perpendicular to the long axis of the glass container. Before being placed on the rollers, the Four glass containers are wrapped in 5.08-centimeter (2-inch) wide tape, and the excess is cut off or folded around the bottom of the container. The container is then placed inside an index card, which is stapled around the specimen. The loading rate for compression of the flask is 1.27 cm / min (0.5 inches / min), meaning that the rollers move toward each other at a rate of 1.27 cm / min (0.5 inches / min). Horizontal compression strength is measured at 25 °C ± 2 °C and 50% ± 5% relative humidity. In some modalities, it is desirable to perform the horizontal compression test within 1 hour (and no more than 24 hours) after depyrogenation to simulate pharmaceutical filling line conditions.Horizontal compressive strength is a measure of load failure, and the measurement of horizontal compressive strength can be provided as a probability of failure at a selected normal compressive load. As used herein, failure occurs when the glass container breaks under horizontal compression in at least 50% of the samples. Thus, horizontal compression is provided for a group of samples. In some embodiments, a coated glass container may have a horizontal compressive strength at least 10%, 20%, or 30% greater than an uncoated flask. Referring now to Figures 1 and 3, the measurement of horizontal compression strength can also be performed on an eroded glass container. Specifically, the operation of the test positioning jig 200 can create damage to the outer surface of the coated glass container 122, such as scratching or erosion, which weakens the strength of the coated glass container 100. The glass container is then subjected to the horizontal compression procedure described earlier, where the container is placed between two rollers with the scratching facing outwards, parallel to the rollers. The scratching can be characterized by the selected normal pressure applied by a bottle-on-bottle positioning jig and the length of the scratch.Unless otherwise specified, the scoring for eroded glass containers for the horizontal compression procedure is characterized by a scoring length of 20 mm created by a normal load of 30 N. It may be preferable to have the scoring at an angle of 90° with respect to the rollers, ±5°. Coated glass containers can be evaluated for horizontal compressive strength after heat treatment. The heat treatment can consist of exposure to a temperature of approximately 250°C, approximately 260°C, approximately 270°C, approximately 280°C, approximately 290°C, approximately 300°C, approximately 310°C, approximately 320°C, approximately 330°C, approximately 340°C, approximately 350°C, approximately 360°C, approximately 370°C, approximately 380°C, approximately 390°C, or approximately 400°C, for a period of time. MA / t / ZUZZ / UÓ IZ !4 30-minute time period. In some embodiments, the horizontal compressive strength of the coated glass container is reduced by no more than approximately 20%, 30%, or even 40% after being exposed to a heat treatment, such as those described above, and then being eroded, as described above. In one embodiment, the horizontal compressive strength of the coated glass container is reduced by no more than approximately 20% after being exposed to a heat treatment of approximately 250°C, approximately 260°C, approximately 270°C, approximately 280°C, approximately 290°C, approximately 300°C, approximately 310°C, approximately 320°C, approximately 330°C, approximately 340°C, approximately 350°C, approximately 360°C, approximately 370°C, approximately 380°C, approximately 390°C, or approximately 400°C, for a period of time of 30 minutes, and then being eroded. The coated glass articles described herein may be thermally stable after heating to a temperature of at least 250°C (or 260°C, or 280°C, or 300°C) for a period of 30 minutes. The phrase "thermally stable," as used herein, means that the coating applied to the glass article remains substantially intact on the surface of the glass article after exposure to elevated temperatures, such that, after such exposure, the mechanical properties of the coated glass article, specifically the coefficient of friction and the resistance to horizontal compression, are only minimally affected, if at all. This indicates that the lubricating coating remains adhered to the surface of the glass after exposure to elevated temperatures and continues to protect the glass article from mechanical damage such as abrasions, impacts, and the like. In the modalities described herein, a coated glass article is considered to be thermally stable if the coated glass article meets both a coefficient of friction standard and a horizontal compressive strength standard after being heated to the specified temperature and held at that temperature for the specified time. To determine whether the coefficient of friction standard is met, the coefficient of friction of a first coated glass article is determined in an as-received condition (i.e., before any thermal exposure) using the test positioning template depicted in FIG. 3 and an applied load of 30 N.A second coated glass article (i.e., a glass article having the same glass composition and coating composition as the first coated glass article) is thermally exposed under the prescribed conditions and cooled to room temperature. The coefficient of friction of the second glass article is then determined using the test positioning template shown in Figure 3. The coated glass article is eroded with an applied load of 30 N, resulting in an erosion (i.e., a scratch) approximately 20 mm long. If the coefficient of friction of the second coated glass article is less than 0.7 and the glass surface of the second glass article in the eroded area has no observable damage, then the standard coefficient of friction is met for the purpose of determining the thermal stability of the coating. The term observable damage, as used herein, means that the glass surface in the eroded area of ​​the glass article contains fewer than six glass cracks per 0.5 cm of eroded area length when viewed with a Nomarski microscope or differential interference contrast (DIC) spectroscopy at 100X magnification using LED or halogen light sources. A standard definition of a glass crack or glass fissure is described in G.D. Quinn, NIST Recommended Practice Guide: Fractography of Ceramics and Glasses, NIST Special Publication 960-17 (2006). To determine if the standard for horizontal compression strength is met, a first coated glass article is etched into the test positioning template shown in Figure 3 under a 30 N load to form a 20 mm scratch. The first coated glass article is then subjected to a horizontal compression test, as described herein, and the retained strength of the first coated glass article is determined. A second coated glass article (i.e., a glass article having the same glass composition and coating composition as the first coated glass article) is thermally exposed under the prescribed conditions and cooled to room temperature. The second coated glass article is then etched into the test positioning template shown in Figure 3 under a 30 N load.The second coated glass article is then subjected to a horizontal compression test, as described herein, and the retained strength of the second coated glass article is determined. If the retained strength of the second coated glass article does not decrease by more than approximately 20% compared to the first coated glass article (i.e., the load at failure does not decrease by more than 20%), then the standard for horizontal compression strength is met for the purpose of determining the thermal stability of the coating. Coated glass containers are considered thermally stable if they meet the coefficient of friction standard and the horizontal compression strength standard after being exposed to a temperature of at least approximately 250 °C (or 260 °C or 280 °C) for a period of at least approximately 30 minutes (i.e., coated glass containers are thermally stable at a temperature of at least approximately 250 °C (or 260 °C or 280 °C) for a period of approximately 30 minutes). Thermal stability is also measured at temperatures from approximately 250 °C (or 260 °C or 280 °C) up to approximately 400 °C. For example, in some embodiments, glass containers Coated glass containers will be considered thermally stable if they meet the standards at a temperature of at least approximately 270 °C or even approximately 280 °C for a period of approximately 30 minutes. In other embodiments, coated glass containers will be considered thermally stable if they meet the standards at a temperature of at least approximately 290 °C or even approximately 300 °C for a period of approximately 30 minutes. In further embodiments, coated glass containers will be considered thermally stable if they meet the standards at a temperature of at least approximately 310 °C or even approximately 320 °C for a period of approximately 30 minutes.In some other applications, coated glass containers will be considered thermally stable if they meet the standards at a temperature of at least approximately 330 °C or even approximately 340 °C for a period of approximately 30 minutes. In some other applications, coated glass containers will be considered thermally stable if they meet the standards at a temperature of at least approximately 350 °C or even approximately 360 °C for a period of approximately 30 minutes. In some other applications, coated glass containers will be considered thermally stable if they meet the standards at a temperature of at least approximately 370 °C or even approximately 380 °C for a period of approximately 30 minutes.Still in other forms, coated glass containers will be considered thermally stable if they meet the standards at a temperature of at least approximately 390 °C or even approximately 400 °C for a period of approximately 30 minutes. The coated glass containers described herein can also be thermally stable over a temperature range, meaning that the coated glass containers are thermally stable by meeting the standard coefficient of friction and the standard resistance to horizontal compression at each temperature on the range. For example, in the embodiments described herein, the coated glass containers can be thermally stable from at least approximately 250 °C (or 260 °C or 280 °C) to a temperature less than or equal to approximately 400 °C. In some embodiments, the coated glass containers can be thermally stable on a scale from at least approximately 250 °C (or 260 °C or 280 °C) to approximately 350 °C.In some other embodiments, coated glass containers can be thermally stable from at least approximately 280 °C to a temperature less than or equal to approximately 350 °C. Still in other embodiments, coated glass containers can be thermally stable from at least approximately 290 °C to approximately 340 °C. In another embodiment, the coated glass container can be thermally stable on a scale of. ML / t / ZUZZ / UÓ IZ / 4 temperatures of approximately 300 °C to approximately 380 °C. In another embodiment, the coated glass container can be thermally stable at a temperature scale of approximately 320 °C to approximately 360 °C. The coated glass containers described herein have a four-point bend strength. To measure the four-point bend strength of a glass container, a glass tube, which is the precursor to the coated glass container 100, is used for measurement. The glass tube has the same diameter as the glass container but does not include a glass container base or a glass container mouth (i.e., before the tube is formed into a glass container). The glass tube is then subjected to a four-point bend strength test to induce mechanical failure. The test is performed at 50% relative humidity with outer contact elements separated by 22.86 cm (9 in) and inner contact elements separated by 7.62 cm (3 in) at a loading rate of 10 mm / min. The four-point bend strength measurement can also be performed on a coated and eroded tube. The operation of the test positioning jig 200 can create surface erosion on the tube, such as surface scoring, which weakens the tube's strength, as described in the measurement of the horizontal compressive strength of an eroded flask. The glass tube is then subjected to a four-point bend strength test to induce mechanical failure. The test is performed at 25°C and 50% relative humidity using outer probes spaced 22.86 cm (9 in) apart and inner contact elements spaced 7.62 cm (3 in) apart at a loading rate of 10 mm / min, while the tube is positioned so that the scoring is under tension during the test. In some cases, the four-point bending strength of a coated glass tube after erosion shows on average at least 10%, 20%, or even 50% greater mechanical strength than that for an uncoated glass tube eroded under the same conditions. In some embodiments, after coated glass container 100 is eroded by an identical glass container with a normal force of 30 N, the coefficient of friction of the eroded area of ​​coated glass container 100 does not increase by more than approximately 20% after further erosion by an identical glass container with a normal force of 30 N at the same location, or it does not increase at all. In other embodiments, after coated glass container 100 is eroded by an identical glass container with a normal force of 30 N, the coefficient of friction of the eroded area of ​​coated glass container 100 does not increase by more than approximately 15% or even 10% after further erosion by an identical glass container with a normal force of 30 N at the same location, or it does not increase at all. ML / t / ZUZZ / UÓ IZ / 4 absolute. However, it is not necessary for all forms of the coated glass container 100 to exhibit such properties. The transparency and color of the coated container can be evaluated by measuring the container's light transmission within a wavelength range of 400–700 nm using a spectrophotometer. Measurements are taken with a light beam directed perpendicular to the container wall so that the beam passes through the coating twice: first upon entering the container and then upon exiting. In some configurations, the light transmission through the coated glass container can be greater than or equal to approximately 55% of the light transmission through an uncoated glass container (passing through two container walls) for wavelengths from approximately 400 nm to approximately 700 nm. As described herein, light transmission can be measured before or after a heat treatment, such as the heat treatments described herein.For example, for each wavelength from approximately 400 nm to approximately 700 nm, the light transmission can be greater than or equal to approximately 55% of the light transmission through an uncoated glass container. In other configurations, the light transmission through the coated glass container is greater than or equal to approximately 55%, approximately 60%, approximately 65%, approximately 70%, approximately 75%, approximately 80%, or even approximately 90% of the light transmission through an uncoated glass container for wavelengths from approximately 400 nm to approximately 700 nm. As described herein, light transmission can be measured before an environmental treatment, such as a heat treatment described herein, or after an environmental treatment.For example, after heat treatment at approximately 250°C, approximately 260°C, approximately 270°C, approximately 280°C, approximately 290°C, approximately 300°C, approximately 310°C, approximately 320°C, approximately 330°C, approximately 340°C, approximately 350°C, approximately 360°C, approximately 370°C, approximately 380°C, approximately 390°C, or approximately 400°C, for a period of 30 minutes, or after exposure to freeze-drying conditions, or after exposure to autoclave sterilization conditions, the light transmission through the coated glass container is greater than or equal to approximately 55%, approximately 60%, approximately 65%, approximately 70%, approximately 75%, approximately 80%, or even approximately 90% of the light transmission through a uncoated glass container for wavelengths from approximately 400 nm to approximately 700 nm. Yellowing caused by exposure to heat treatments can be measured ML / t / ZUZZ / UÓ IZ / 4 by means of the xyy coordinates according to the IEC 1931 color space, which is described with the Examples provided herein. The change in the xyy coordinates after the depyrogenation conditions may indicate a yellowing of the coated glass article. In some embodiments, the coated glass container 100 may appear colorless and transparent to the naked eye when viewed from any angle. In other embodiments, the coating 120 may have a perceptible tint, such as when the coating 120 comprises a colored polymer. In some embodiments, the coated glass container 100 may have a coating 120 that is capable of receiving an adhesive label. That is, the coated glass container 100 can receive an adhesive label on its coated surface in such a way that the label is firmly affixed. However, the ability to affix an adhesive label is not a requirement for all embodiments of the coated glass containers 100 described herein. EXAMPLES The different types of coated glass containers will become clearer with the following examples. These examples are illustrative and should not be interpreted as limiting the scope of this description. In the examples, all reported CoF values ​​are the average CoF, not the maximum CoF as described herein. EXAMPLE 1 Cyanate ester monomers were compared to estimate their solubility in various commonly used commercial solvents. The selected monomers were bisphenol A cyanate ester (DCBA), C,C'-[(dimethylsilylene)de-4,1-phenylene] ester (Si-DCBA), and C,C'-((2,2,2-tnfluoro-1-(trifluoromethyl)ethylene)de-4,1-phenylene) ester (F-DCBA). The selected solvents were ethanol, methanol, acetone, butanone (also known as methyl ethyl ketone (MEK)), methylene chloride (CH2Cl2), propylene glycol methyl ether acetate (PGMEA), and acetonitrile. Sample solutions were prepared by dissolving 50 mg of cyanate ester monomer powders in 10 mL of solvent. Sample solutions of each monomer were prepared in each solvent.The sample solutions were observed to determine the amount of time elapsed before the monomer dissolved completely, that is, the amount of time that elapsed before the sample solutions became completely transparent. Monomers in sample solutions in which more than 30 minutes elapsed were considered to have dissolved. MA / t / ZUZZ / UÓ IZ / 4 minutes before complete transparency, were unable to dissolve completely. The results are reported in Table 1 below. ML / t / ZUZZ / UÓ IZ / 4 TABLE 1 Ethanol Methanol CH2CI2 PGMEA Acetone MEK Acetonitrile DCBA >30 min. >30 min. ~10 min. ~5 min. ~30 sec. ~30 sec. <10 sec. F-DCBA <10 sec. <10 sec. <10 sec. <10 sec. <10 sec. <10 sec. <10 sec. SiDCBA >30 min. >30 min. >30 min. >30 min. >30 min. >30 min. >30 min. As shown in Table 1, DCBA was able to dissolve completely in CH2CI2, PGMEA, acetone, MEK, and acetonitrol within several seconds to several minutes, but it did not dissolve completely in ethanol or methanol. F-DCBA exhibited superior solubility and was able to dissolve completely in all solvents within seconds. Si-DCBA exhibited the poorest solubility and was not able to dissolve completely in any of the solvents. Si-DCBA exhibited particularly low transparency in ethanol and methanol solutions. EXAMPLE 2 Two sets of coated glass wafers were tested for percentage transmission to estimate the transparency of various cyanate ester coatings in the UV-visible light range. The first set (glasses 1–5) was 1 mm thick, and the second set (glasses 6–10) was 2 mm thick. The percentage transmission of glasses 1 and 7 was tested in an uncoated condition. The percentage transmission of glass 2 was tested after spin-coating with an F-DCBA prepolymer coating. The percentage transmission of glasses 3–6 was tested after spin-coating with 30 mg / ml, 20 mg / ml, 10 mg / ml, and 5 mg / ml F-DCBA monomer coatings, respectively. The percentage transmission of glass 8 was tested after spin-coating with a DCBA prepolymer coating.The transmission percentage of glasses 9-10 was tested after spin-coating with 30 mg / ml and 20 mg / ml DCBA monomer coatings, respectively. The results are graphically represented in Figure 4 and reported in Table 2 below. In Figure 4, line 301 represents the data for glasses 1-5 and line 302 represents the data for glasses 6-10. TABLE 2 No. Coating Glass Thickness % Transmission Glass 1 No coating 1 mm 92.08 Glass 2 F-DCBA prepolymer solution 1 mm 91.77 Glass 3 30 mg / ml F-DCBA monomer solution 1 mm 92.06 Glass 4 20 mg / ml F-DCBA monomer solution 1 mm 92.06 Glass 5 10 mg / ml F-DCBA monomer solution 1 mm 91.88 Glass 6 5 mg / ml F-DCBA monomer solution 1 mm 92.06 Glass 7 No coating 2 mm 91.88 Glass 8 DCBA prepolymer solution 2 mm 91.77 Glass 9 30 mg / ml DCBA monomer solution 2 mm 91.41 Glass 10 20 mg / ml DCBA monomer solution 2 mm 92.00 ML / t / ZUZZ / UÓ IZ / 4 As shown in Table 2, the thickness of the glass wafer, the cyanate ester, the concentration of the coating solution, and whether the coating solution was refluxed to form a prepolymer solution had little influence on the final optical properties of the glass. The decrease in the percentage of transmission when comparing an uncoated glass wafer with a coated glass wafer was never more than 0.5%. Furthermore, with reference to Figure 4, almost any difference between the percentage of transmission of the two sets of coated flasks was located entirely within the UV range (10–400 nm). That is, any influence these properties had on the percentage of transmission would not be detectable by visual inspection. EXAMPLE 3 Pharmaceutical packaging bottles were coated by immersion in an F-DCBA monomer coating, and the coating was subsequently cured (Initial Curing). After curing, the coated bottles were tested for CoF using the testing procedures described herein. The coated bottles were then subjected to further heat treatments for 30 minutes at 260 °C (Second Heat Treatment) and retested for CoF. Finally, the coated bottles were subjected to yet another heat treatment for 16 hours at 335 °C (Final Heat Treatment) and tested for CoF. The results are reported in Table 3 below. TABLE 3 Force (N) Position Avg. CoF 5 After Initial Curing 0.100 5 After Second Heat Treatment 0.431 5 After Final Heat Treatment 0.923 30 After Initial Curing 0.128 30 After Second Heat Treatment 0.406 30 After Final Heat Treatment 0.762 ML / t / ZUZZ / UÓ IZ / 4 As shown in Table 3, the coated flasks have excellent CoF values ​​after the initial curing process. However, after heat treatments, the CoF values ​​increase significantly. This increase in CoF values ​​may be the result of incomplete curing of the coating, indicating that a temperature higher than 200 °C may be necessary to achieve complete crosslinking and good thermal resistance. Furthermore, this increase in CoF values ​​may be due to the decomposition of F-DCBA caused by side reactions during the coating and curing processes. Compared to DCBA, F-DCBA is less stable due to its highly active cyanate ester portion, which produces side reactions with both Lewis acids and bases such as water and non-dried solvents. Nevertheless, the CoF after the second heat treatment remained lower than that of the uncoated glass. EXAMPLE 4 F-DCBA monomer coatings were tested for contact angle to characterize liquid wettability on the coating surface. Glass wafers measuring 50 mm x 50 mm x 1.1 mm were spin-coated with an F-DCBA monomer coating. After spin-coating, the F-DCBA monomer was cured for 1 hour at 80 °C and an additional 1 hour at 200 °C. After curing, the coated glass wafers were heated for 16 hours at 335 °C. The contact angle was measured by measuring the contact angle between a 2.0 pL water droplet and the cyanate ester-coated surface. The contact angle was measured once after curing and at various stages of the heat resistance test, for a total of six measurements. The results are reported in Table 4 below. TABLE 4 Measurement time Contact angle After curing 80.1 After 1 h at 335 °C 79.5 After 2 h at 335 °C 75.2 After 4 h at 335 °C 72.0 After 8 h at 335 °C 70.0 After 16 h at 335 °C 61.5 MA / t / ZUZZ / UÓ IZ / 4 As can be seen in Table 4, the contact angle gradually decreased with increasing heating time. This may indicate the gradual decomposition of the F-DCBA coating during the thermal resistance test. This decrease in the contact angle is believed to be due to the coating surface's wettability approaching that of uncoated glass, resulting from a reduction in coating thickness. Based on the results in Table 4, the contact angle measured after 4 hours at 335 °C was chosen as the critical heating time for assessing the thermal resistance of the cyanate ester coatings. At this point, the change in the contact angle becomes evident when compared to the initial state. EXAMPLE 5 DCBA monomer coatings were tested for contact angle and CoF in a manner similar to Example 4. Glass wafers measuring 50 mm x 50 mm x 1.1 mm were spin-coated with a DCBA monomer in a MEK. After spin-coating, the DCBA monomer was cured for 1 hour at 180 °C and an additional 1 hour at 200 °C. After curing, the flasks were heated for 8 hours at 335 °C. The contact angle was measured after curing and at various stages of the heat resistance test. The results are reported in Table 5 below. TABLE 5 Measurement time Contact angle After curing 101.9 After 1 ha 335 °C 102.4 After 2 ha 335 °C 98.7 After 4 ha 335 °C 88.5 After 8 ha 335 °C 72.9 After 16 ha 335 °C 46.9 ML / t / ZUZZ / UÓ IZ ! + As shown in Table 5, the DCBA coatings are more hydrophobic than the F-DCBA coatings in Example 4. Although fluorinated compounds, such as F-DCBA, should have greater hydrophobicity and lubrication, the results demonstrate that the DCBA coatings can have a contact angle as high as 102.4° compared to the highest measured contact angle of 80.1° for the F-DCBA coating in Example 4. Furthermore, even after the 4-hour heat resistance test, the DCBA coatings had a higher contact angle than the initial contact angle of the F-DCBA coating reported in Table 4. This may be due to the instability of F-DCBA during the curing process, indicating that F-DCBA coatings may have a tendency to decompose faster than the relatively stable DCBA coatings. EXAMPLE 6 Two batches of pharmaceutical packaging bottles were coated by immersion in DCBA monomer in a MEK solvent. The first batch (DCBA-1) was cured for 1 hour at 180 °C and an additional 1 hour at 200 °C. The second batch (DCBA-4) was cured for 1 hour at 180 °C and an additional 4 hours at 200 °C. After curing, the coated bottles were tested for CoF using the test procedures described herein. The coated bottles were then subjected to further heat treatments for 35 minutes at 320 °C and retested for CoF. Finally, the coated bottles were subjected to yet another heat treatment for 9 hours at 335 °C and tested for CoF. The results are reported in Table 6 below. TABLE 6 Batch Strength Position Avg. CoF DCBA-1 5 After Initial Curing 0.276 DCBA-1 5 After Second Heat Treatment 0.244 DCBA-1 5 After Final Heat Treatment 0.522 DCBA-1 30 After Initial Curing 0.263 DCBA-1 30 After Second Heat Treatment 0.235 DCBA-1 30 After Final Heat Treatment 0.610 DCBA-4 5 After Initial Curing 0.355 DCBA-4 5 After Second Heat Treatment 0.330 DCBA-4 5 After Final Heat Treatment - DCBA-4 30 After Initial Curing 0.295 DCBA-4 30 After Second Heat Treatment 0.269 DCBA-4 30 After Final Heat Treatment - ML / t / ZUZZ / UÓ IZ ! + As shown in Table 6, the CoF of DCBA-1 decreased slightly after the second heat treatment but increased significantly after the extended final heat treatment. The CoF of DCBA-4, like DCBA-1, decreased slightly after the second heat treatment, but its CoF values ​​were higher than those of DCBA-1 both after the initial curing and after heating. Based on these results, an extended curing time may have little impact on the CoF or the thermal resistance of the DCBA coating. EXAMPLE 7 The thickness of DCBA coatings applied by dip coating was observed using scanning electron microscopy (SEM). Glass wafers measuring 50 mm x 50 mm x 1.1 mm were spin-coated with a DCBA monomer coating at 20 mg / ml and a prepolymer coating at 30 mg / ml. After spin curing, the DCBA coatings were cured for 1 hour at 180 °C and an additional 1 hour at 200 °C. The thicknesses of the cured coatings were then measured using SEM. The average coating thickness of the DCBA monomer coating was 37.7 nm. The prepolymer coating was more concentrated and viscous, with an average coating thickness of 221 nm. A small gap was also observed between the prepolymer coating and the glass surface. This could indicate that coating adhesion may be affected by residual solvent during the curing process. EXAMPLE 8The thickness of F-DCBA coatings applied by dip coating was observed using SEM. Glass wafers measuring 50 mm x 50 mm x 1.1 mm were spin-coated with F-DCBA monomer at 20 mg / ml, F-DCBA monomer at 30 mg / ml, and F-DCBA prepolymer at 20 mg / ml. After spin curing, the F-DCBA coatings were cured for 1 hour at 180 °C and an additional 1 hour at 200 °C. The thicknesses of the cured coatings were then measured using SEM. The average coating thickness of the F-DCBA monomer coating at 20 mg / ml was 58.2 nm. The average coating thickness of the F-DCBA monomer coating at 30 mg / ml was 158 nm. The prepolymer coating was again more concentrated and viscous with an average coating thickness of 480 nm.Furthermore, it was observed that not only did the coating thickness increase as the coating concentration increased, but the variation in thickness across the glass surface also increased. It should now be understood that the low-friction coated glass containers described herein exhibit improved resistance to mechanical damage as a result of the application of the low-friction coating, and therefore, the glass containers have enhanced mechanical durability. This property makes the glass containers suitable for use in various applications, including, but not limited to, pharmaceutical packaging materials. It will be evident to those skilled in the art that various modifications and variations can be made to the embodiments described herein without departing from the spirit and scope of the subject matter claimed. It is thus intended that this specification cover modifications and variations of the various embodiments described herein, provided that such modifications and variations fall within the scope of the appended claims and their equivalents.

Claims

1. A pharmaceutical container comprising: a glass container comprising a first surface and a second surface opposite the first surface, wherein the first surface is an outer surface of the glass container; and a coating positioned over at least a portion of the first surface of the glass container, the coating comprising polycyanurate.

2. The pharmaceutical packaging according to claim 1, further characterized in that the polycyanurate comprises monomeric units formed from one or more bisphenol cyanate esters.

3. The pharmaceutical packaging according to claim 2, further characterized in that the one or more bisphenol cyanate esters are selected from bisphenol cyanate ester A, bisphenol cyanate ester E, C,C'-((2,2,2-tnfluoro-l-(trifluoromethyl)ethylidene)di4,1-phenylene) ester, tetramethylbisphenol cyanate ester F, bisphenol cyanate ester M, C,C'((2,2,2-trifluoro-l-(trifluoromethyl)ethylidene)di-4,l-phenylene) ester, or combinations thereof.

4. The pharmaceutical packaging according to claim 1, further characterized in that the coating has a thickness of 100 nm or less.

5. The pharmaceutical packaging according to claim 1, further characterized in that the coating is in direct contact with at least a portion of the first surface of the glass container.

6. The pharmaceutical container according to claim 1, further characterized in that the portion of the first surface of the glass container with the coating has a coefficient of friction less than or equal to approximately 0.

7.

7. The pharmaceutical container according to claim 6, further characterized in that the portion of the first surface of the glass container with the coating maintains the coefficient of friction less than or equal to approximately 0.7 after heat treatment at a temperature of at least approximately 250 °C for 30 minutes.

8. The pharmaceutical packaging according to claim 1, further characterized in that a light transmission through the pharmaceutical packaging is greater than or equal to approximately 55% of a light transmission through an uncoated pharmaceutical packaging for each wavelength from approximately 400 nm to approximately 700 nm.

9. The pharmaceutical container according to claim 8, further characterized in that the pharmaceutical container maintains light transmission through the pharmaceutical container greater than or equal to approximately 55% of the light transmission through the uncoated pharmaceutical container for each wavelength from approximately 400 nm to approximately 700 nm after heat treatment at a temperature of at least approximately 250 °C for 30 minutes.

10. A pharmaceutical container comprising: a glass container comprising a first surface and a second surface opposite the first surface, wherein the first surface is an outer surface of the glass container; and a coating positioned over at least a portion of the first surface of the glass container, the coating being formed of one or more cyanate asters.

11. The pharmaceutical packaging according to claim 10, further characterized in that the one or more cyanate esters are selected from one or more bisphenol cyanate esters.

12. The pharmaceutical container according to claim 11, further characterized in that the one or more bisphenol cyanate esters are selected from bisphenol cyanate ester A, bisphenol cyanate ester E, C,C'-((2,2,2-trifluoro-1-(trifluoromethyl)ethylidene)d1-4,1-phenylene) ester, tetramethylbisphenol cyanate ester F, bisphenol cyanate ester M, C,C'-((2,2,2-trifluoro-1-(trifluoromethyl)ethylidene)d1-4,1-phenylene) ester, or combinations thereof.

13. The pharmaceutical packaging according to claim 11, further characterized in that the coating has a thickness of 100 nm or less.

14. The pharmaceutical packaging according to claim 11, further characterized in that the coating is in direct contact with at least a portion of the first surface of the glass container.

15. The pharmaceutical container according to claim 11, further characterized in that the portion of the first surface of the glass container with the coating has a coefficient of friction less than or equal to approximately 0.

7.

16. The pharmaceutical container according to claim 11, further characterized in that a light transmission through the pharmaceutical container is greater than or equal to approximately 55% of a light transmission through an uncoated pharmaceutical container for each wavelength from approximately 400 nm to approximately 700 nm.

17. A method for producing a coated pharmaceutical container, the method comprising: depositing a coating precursor mixture onto a first surface of an outer surface of a glass container, the coating precursor mixture comprising one or more cyanate esters; and heating the coating precursor mixture to form a coating on the outer surface of the glass container, the coating comprising polycyanurate.

18. The method according to claim 17, further characterized in that the one or more cyanate esters are selected from one or more bisphenol cyanate esters. 5 19. The pharmaceutical container according to claim 11, further characterized in that the one or more bisphenol cyanate esters are selected from bisphenol cyanate ester A, bisphenol cyanate ester E, C,C'-((2,2,2-trifluoro-1-(trifluoromethyl)ethylene)d1-4,1-phenylene ester), tetramethylbisphenol cyanate ester F, bisphenol cyanate ester M, C,C'-((2,2,2-trifluoro-1-(trifluoromethyl)ethylene)d1-4,1-phenylene ester), or combinations thereof.

20. The method according to claim 18, further characterized in that the heating of the coating precursor mixture is to a temperature of less than 230°C.

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