Anaerobically curable composition

Abstract

An anaerobically curable composition comprising: a liquid anaerobically curable component; a solid anaerobically curable component; a solid polyether polyvinyl butyral resin; and a curing component for curing the anaerobically curable component. Advantageously, the compositions of the present invention are substantially solid and can be used as thread locking agents.

Description

Technical Field

[0001] The present invention relates to anaerobically curable compositions which can be used in many applications including as threadlockers. The composition is substantially solid and can be provided in any suitable solid form including tape form, filament form or as a coating applied to a substrate including, for example, filaments or threads made of other materials such as nylon or polyester threads. The present invention also relates to methods of making threaded components and methods of assembling threaded components. The composition can be easily handled and applied to threaded members. The composition is heat resistant at a temperature of at least 150°C.

[0002] Related technologies

[0003] Threadlocking compositions are used to lock and / or seal threaded components such as nuts and bolts together in an interlocked state. Such threadlocking compositions significantly increase the torque required to disconnect or rotate the engaged threaded components. Conventional threadlocking compositions often include co-reactive adhesive systems, in which two or more components are mixed and then the resulting composition is applied to one or more threaded engagement surfaces of a fastener, and the components in the threadlocking composition react to cure on the one or more threaded engagement surfaces. Examples of such co-reactive systems include epoxy resin adhesive compositions.

[0004] Liquid adhesive compositions have long been used in sealing and thread locking applications and have become a standard part in component production and maintenance of machinery, tools, etc. The liquid adhesive compositions commonly used in these applications are anaerobic compositions. These compositions provide excellent thread locking and sealing properties after curing. The anaerobic curable compositions applied to the threaded parts as thread locking compositions remain stable (in an uncured state), and therefore in liquid form, until they are placed between the interlocking threaded parts, where they cure in the absence of oxygen.

[0005] Anaerobic curable compositions are generally well known. See, for example, RD Riich, "Anaerobic Adhesives", Handbook of Adhesive Technology, 29, 467-79, A. Pizzi and KL Mittal, eds., Marcel Dekker, Inc., New York (1994), and references cited therein. Their uses are widespread, and new applications are constantly being developed.

[0006] Anaerobic adhesive systems are those that are stable in the presence of oxygen but polymerize in the absence of oxygen. Polymerization is initiated by the presence of free radicals, usually generated by peroxide compounds. Anaerobic adhesive compositions are well known for their ability to remain in a liquid, unpolymerized state in the presence of oxygen and cure to a solid state when oxygen is excluded.

[0007] Typically, anaerobic adhesive systems comprise resin monomers terminated with polymerizable acrylates (e.g., methacrylates, ethacrylates, and chloroacrylates) derived according to known urethane chemistry [e.g., polyethylene glycol dimethacrylate and urethane-acrylates (e.g., U.S. Pat. No. 3,425,988 (Gorman)] Other ingredients typically present in anaerobically curable adhesive compositions include: initiators, such as organic hydroperoxides, e.g., cumene hydroperoxide, t-butyl hydroperoxide, and the like; accelerators for increasing the rate at which the composition cures; and stabilizers, such as quinones or hydroquinones, which are included to help prevent premature polymerization of the adhesive due to decomposition of the peroxide compound.

[0008] Desirable cure inducing compositions for inducing and accelerating anaerobic cure may include one or more of saccharin, toluidine (such as N,N-diethyl-p-toluidine ("DE-pT") and N,N-dimethyl-o-toluidine ("DM-oT")) and acetophenylhydrazine ("APH"), and maleic acid. See, e.g., U.S. Pat. Nos. 3,218,305 (Krieble), 4,180,640 (Melody), 4,287,330 (Rich), and 4,321,349 (Rich).

[0009] Saccharin and APH are used as standard cure accelerator components in anaerobic adhesive cure systems. In fact, many of the Brand anaerobic adhesive products use saccharin alone, or saccharin and APH.

[0010] Anaerobically curable adhesive compositions also typically include a chelating agent, such as ethylenediaminetetraacetic acid (EDTA), to chelate metal ions.

[0011] Compositions suitable for use in pre-applied threadlocking applications are typically applied dry to the touch but have a post-application anaerobic cure capability.

[0012] In some cases, the dry-to-touch form is achieved using a curing mechanism. For example, a first curing mechanism may form a dry-to-touch form to hold the composition in place on the article, while a second curing mechanism is later activated to achieve thread locking.

[0013] For example, European Patent No. 0 077 659 (Thompson) describes a pre-applied polymerizable fluid for sealing and locking engineering components. The composition has two curing mechanisms and two curing reactions occur. The first mechanism is UV curing. A sunscreen is dispersed in the fluid so that the fluid becomes substantially opaque to radiation. After the fluid is applied to the component, it is exposed to UV radiation and then a coating is formed, resulting in a surface layer that is a dry, non-sticky outer skin. The subcutaneous fluid is not affected by the radiation and remains generally liquid. When the component is screwed into another component, the surface layer breaks and initiates a second polymerization (such as free radical polymerization), and once an anaerobic environment is established due to the interlocking of the threaded components, a second curing reaction occurs. The second polymerization mechanism is used to lock the threads together. In Thompson, only the epidermis is formed in the first polymerization, and the remainder of the composition remains fluid under the epidermis. Therefore, there is a risk that the epidermis may be damaged and the fluid composition may leak during the handling of the coated engineering component.

[0014] Similarly, European Patent No. 0 548 369 (Usami) describes a pre-applied adhesive composition for application to the threaded contact surface of a screw component (such as a screw). The composition comprises a light-hardening binder in which a second curable composition is dispersed. The second curable composition includes a microencapsulated reactive monomer / activator / initiator.

[0015] International Patent Publication WO2004 / 024841A2 (Haller) describes a curable composition for application to a threaded article. The composition comprises a dispersion of: a first cure mechanism component comprising: (a) a (meth)acrylate functional monomer component; (b) a (meth)acrylate functional oligomer component; and (c) a photoinitiator component; and (ii) a second cure mechanism component comprising: (e) an amine component; and (f) an encapsulated epoxy resin component; together with (iii) a thickener component. The photoinitiator component is adapted to achieve a first cure through the depth of the composition applied to the threaded article upon irradiation of the composition, thereby forming a binder matrix with the second cure mechanism components dispersed throughout the matrix.

[0016] U.S. Patent No. 9,181,457 (Attarwala) describes a dry-to-touch composition comprising a polymer matrix and an anaerobic curable component present in the polymer matrix. In a particularly desirable form, the composition is moisture curable. The composition is non-flowable at elevated temperatures and has improved solvent resistance once cured. The composition is useful as a threadlocking composition and can be formulated as a coating on a carrier substrate such as a tape, string or sheet.

[0017] British Patent No. 2,543,756 (Ledwith) describes a threadlocking composition comprising an anaerobic curable component and a curing component for curing the anaerobic curable component; wherein the composition is in the form of a flowable granule and has a melting point in the range of 30-100°C. The anaerobic curable component may comprise an anaerobic curable monomer and a resin component. The composition may be provided in the form of at least two parts. The anaerobic curable component is preferably provided in the form of a powder. Preferably, the resin component is selected from a methacrylated polyurethane resin, a novolac resin or a high methacrylated polyester resin. The anaerobic curable monomer preferably comprises at least one acrylate or methacrylate group. The composition is preferably solvent-free. A method of threadlocking two threaded articles together is also disclosed, the method comprising: applying the composition to the threads of at least one article so as to fuse them by melting onto the threads; subsequently and optionally after cooling, threading the two articles together so as to initiate anaerobic curing of the threadlocking composition, thereby chemically bonding the two articles together. Also disclosed are articles having the compositions applied thereto.

[0018] U.S. Patent Application Publication No. 4,039,705 (Douek) relates to anaerobically curable pressure-sensitive adhesive stock such as sheets and tapes, from which a pressure-sensitive adhesive layer comprising at least one anaerobic resin system can be completely transferred to one substrate to bond to another substrate, and cured when activated by a peroxy initiator and with the exclusion of oxygen. The anaerobic pressure-sensitive adhesive is contained between two different release surfaces, which enables the pressure-sensitive adhesive to be transferred to a substrate to be securely fixed to another substrate when the anaerobic curable pressure-sensitive adhesive is cured.

[0019] Although conventional anaerobic threadlockers have been and are still popular in the market, for some commercial applications, some disadvantages have been observed when using conventional liquid anaerobic threadlockers and known non-flowable thixotropic anaerobic threadlockers. For example, such compositions are often unable to fully cure through large gaps. In addition, due to their anaerobic curing properties, once applied to the adhesive portion that is still exposed to the air on the component, it will be difficult to cure (without a triggered secondary curing mechanism). Therefore, the outer glue layer that is still exposed to the air on the nut / bolt assembly will often remain liquid unless additional additives and curing measures are taken to ensure curing. Therefore, the liquid composition at the outer glue layer tends to migrate. In the case of conventional non-flowable compositions (their non-flowability depends on the thixotropic and / or rheological properties of the composition), if the temperature to which they are exposed is high enough, these compositions will flow. In addition, the solvent resistance of the cured product (with a still uncured portion, as noted above) may be poor, which shows that integrity is problematic when environmental interactions occur. This may lead to pollution problems and hazardous conditions for the surroundings.

[0020] Despite the prior art, it would be desirable to provide alternative threadlocking systems including threaded members including a dry-to-touch threadlocking composition; methods for forming such threaded members; and methods for assembling such threaded members. Summary of the invention

[0021] In one aspect, the present invention provides an anaerobically curable composition, the anaerobically curable composition comprising:

[0022] Liquid anaerobically curable components;

[0023] Solid anaerobically curable components;

[0024] Solid thermoplastic polyvinyl butyral resin; and

[0025] A curing component for curing anaerobically curable components.

[0026] Advantageously, the compositions of the present invention are substantially solid and can be used to provide any suitable solid form. The compositions of the present invention can be used in any suitable application. For example, they can be provided in solid form on a threaded article, in a thread form or in a tape form. The compositions of the present invention can be provided on a carrier or can be in a self-supporting form.

[0027] The softening point of the solid thermoplastic polyvinyl butyral resin may be in the range of about 50°C to about 300°C, suitably about 100°C to about 250°C, preferably about 140°C to about 200°C. The solid thermoplastic polyvinyl butyral resin may act as a film former. It is believed that the use of a solid thermoplastic polyvinyl butyral resin having a high softening point (e.g., about 140°C to about 200°C) imparts good heat resistance to the resulting composition, thereby enabling them to perform well at high temperatures. For example, the composition of the present invention in the form of a tape is suitable for use at elevated temperatures (e.g., at 100°C, 150°C, or even higher).

[0028] The molecular weight Mw of the solid thermoplastic polyvinyl butyral resin may be in the range of about 40,000 g / mol to about 250,000 g / mol, suitably in the range of about 40,000 g / mol to about 170,000 g / mol, such as about 40,000 g / mol to 120,000 g / mol, for example 50,000 g / mol to 80,000 g / mol, wherein the molecular weight Mw is determined according to ASTM D5296-05 (Standard Test Method for Molecular Weight Averages and Molecular Weight Distribution of Polystyrene by High Performance Size-Exclusion Chromatography).

[0029] The liquid anaerobic curable component may be present in an amount of about 5 wt % to about 50 wt % based on the total weight of the curable composition, suitably about 10 wt % to about 40 wt % based on the total weight of the curable composition, such as about 30 wt % based on the total weight of the curable composition. When the liquid anaerobic curable component is present in an amount less than about 5 wt % based on the total weight of the composition, the composition may be too hard / non-flowable when applied / coated to a substrate and may therefore not be able to move adequately, for example may not be able to move into the space between mutually threaded threads that are screwed together, may have poor thread locking properties, or may have poor adhesion properties. When the liquid anaerobic curable component is present in an amount greater than about 50 wt % based on the total weight of the composition, the integrity of the component may be adversely affected and the composition may be too flowable / soft and, for example, a coating formed from the composition may be susceptible to rupture when in contact with other surfaces, such as surfaces of processing equipment or other substrates, including other substrates to which the coating may have been applied. When the liquid anaerobically curable component is present in an amount of about 5 wt % to about 50 wt % based on the total weight of the curable composition, this provides the composition with an acceptable balance of thread locking and / or adhesive properties and a composition that forms a coating with sufficient integrity that is required for application of the composition to the parts to be bonded and cures to give good bond strength that is required for the bonding end use.

[0030] Solid anaerobic curable components can be present in an amount of about 6% to about 50% by weight based on the total weight of the composition, suitably about 10% to about 25% by weight based on the total weight of the curable composition, such as about 13% by weight based on the total weight of the curable composition. Compositions containing less than about 6% by weight of solid anaerobic curable components tend to lack cohesive strength and may not be suitable for application on parts. For example, a coating formed by such a composition may be easily broken when contacting with other surfaces (such as the surface of a processing device or other substrate, other substrates including other substrates to which a coating may have been applied). Compositions containing greater than about 50% by weight of solid anaerobic curable components are prone to forming a coating that is too brittle for any component to be bonded. When a solid anaerobic curable component is present in an amount of about 6% to about 50% by weight based on the total weight of the composition, this provides an acceptable balance between (when cured) thread locking and / or adhesive properties and a composition that can be applied as a coating with sufficient integrity and strength.

[0031] Solid thermoplastic polyvinyl butyral resin can be present in an amount of about 10% to about 50% by weight based on the total weight of the curable composition, suitably about 15% to about 40% by weight based on the total weight of the curable composition, such as about 15% to about 35% by weight based on the total weight of the curable composition, for example, about 20% by weight. Compositions containing less than about 10% by weight of solid thermoplastic polyvinyl butyral resin are prone to have elastomeric properties that are insufficient to enable the composition to be properly applied to the parts to be bonded. Compositions containing greater than about 50% by weight of solid thermoplastic polyether polyurethane components are prone to exhibit poor thread locking / adhesion properties. When solid thermoplastic polyether polyurethane resin is present in an amount of about 10% to about 50% by weight based on the total weight of the curable composition, this provides the composition with an acceptable balance between thread locking and / or adhesion properties and a coating having sufficient elastomeric properties to allow the composition to be applied to the parts to be bonded.

[0032] The curing component for curing the anaerobically curable component may be present in an amount of about 0.1 to about 10 weight percent based on the total weight of the curable composition, such as about 1 to about 5 weight percent based on the total weight of the curable composition.

[0033] Suitably, the liquid anaerobic curable component comprises a liquid (meth)acrylate monomer component.

[0034] The liquid (meth)acrylate monomer component may be one or more selected from those having the following formula:

[0035] H 2 C=CGCO 2 R 8 ,

[0036] wherein G is hydrogen, halogen or an alkyl group having 1 to 4 carbon atoms, and R 8 Selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, alkaryl or aryl groups having from 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted by silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, carbamate, carbonate, amine, amide, sulfur, sulfonate, sulfone, etc., as the case may be.

[0037] Suitably, the solid anaerobic curable component comprises one or more solid (meth)acrylate monomer components. For example, the solid anaerobic curable component may be the reaction product of an isocyanate-containing compound such as phenyl isocyanate and a hydroxyalkyl (meth)acrylate such as hydroxyethyl methacrylate (HEMA):

[0038]

[0039] It is 2-methacryloyloxyethyl carbamate with a melting point of about 70-75°C.

[0040] The solid anaerobic curable component can also be the reaction product of 2 molar equivalents of HEMA and 1 molar equivalent of a diisocyanate such as isophorone diisocyanate (IPDI), 4,4′-methylenebis(cyclohexyl isocyanate) (HMDI), or 1,5-cyclohexyl diisocyanate (CHDI). For example:

[0041]

[0042] It is HEMA-IPDI-HEMA with a melting point of about 72-74°C.

[0043]

[0044] It is HEMA-HMDI-HEMA with a melting point of about 75-85°C.

[0045]

[0046] It is HEMA-CHDI-HEMA with a melting point of about 75-85°C.

[0047] The solid anaerobic curable component may also be a polyurethane methacrylate resin having a molecular weight > 2000 g.mol and having a semi-crystalline polyester polyol backbone. Examples of such resins are given in International Patent Publication WO 2017 / 68196A1 and are the reaction products of polyols known as Dynacoll 7380 with toluene diisocyanate, subsequently end-capped with HEMA. The melting points of these resins are in the range of 50-80°C.

[0048] Also used as solid anaerobic curable components are novolac vinyl ester resins, which are the reaction products of novolac epoxy resins and methacrylic acid. Examples of these resins and their preparation are shown in U.S. Pat. No. 9,957,344. For example

[0049]

[0050] wherein n is an integer of 2-10, and the melting point of the compound is about 70-75°C.

[0051] Suitably, the curing component comprises one or more selected from the group consisting of 1-acetyl-2-phenylhydrazine, N,N-dimethyl-p-toluidine, N,N-diethyl-p-toluidine, N,N-diethanol-p-toluidine, N,N-dimethyl-o-toluidine, N,N-dimethyl-m-toluidine, indoline, 2-methylindoline, isoindoline, indole, 1,2,3,4-tetrahydroquinoline, 3-methyl-1,2,3,4-tetrahydro-quinoline, 2-methyl-1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinoline-4-carboxylic acid, and 1,2,3,4-tetrahydro-benzo(H)quinolin-3-ol.

[0052] The anaerobically curable composition of the present invention may include a curing accelerator encompassed by the following formula:

[0053]

[0054] Where X is CH 2 , O, S, NR 4 , CR 5 R 6 or C=O; R is one or more of hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynyl; R 1 -R 6 R is independently selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; 7 is hydrogen or CHR 8 R 9 , where R 8 and R 9 each is independently selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; and n is 0 or 1.

[0055] Optionally, the above curing accelerator is used in combination with at least one co-accelerator selected from amines, amine oxides, sulfonamides, metal sources, acids and mixtures thereof.

[0056] For example, the co-accelerator can be selected from triazines, ethanolamine, diethanolamine, triethanolamine, N,N dimethylaniline, benzene sulphanimide, cyclohexylamine, triethylamine, butylamine, saccharin, N,N-diethyl-p-toluidine, N,N-dimethyl-o-toluidine, acetophenylhydrazine, maleic acid and mixtures thereof.

[0057] The curing accelerator can be

[0058]

[0059] wherein R is one or more of hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynyl; and R 1 and R 2 Each is independently selected from halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl.

[0060] For example, the curing accelerator may be selected from one or more of the following:

[0061]

[0062] wherein R is as defined above.

[0063] The curing accelerator can be

[0064]

[0065] 1,2,3,4-Tetrahydrobenzo-h-quinolin-3-ol.

[0066] The compositions of the present invention may also contain a free radical polymerization initiator, such as a peroxide.

[0067] The free radical polymerization initiator is one or more selected from the following: isopropylbenzene hydroperoxide ("CHP"), terpene hydroperoxide, tert-butyl hydroperoxide ("TBH"), tert-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1,3-bis(tert-butylperoxyisopropyl)benzene, diacetyl peroxide, 4,4-bis(tert-butylperoxy)butyl valerate, p-chlorobenzoyl peroxide, tert-butyl isopropylbenzene peroxide, tert-butyl perbenzoate, di-tert-butyl peroxide, diisopropylbenzene peroxide, 2,5-dimethyl-2,5-di-tert-butyl peroxyhexane, 2,5-dimethyl-2,5-di-tert-butyl-peroxyhex-3-yne, 4-methyl-2,2-di-tert-butyl peroxypentane, tert-amyl hydroperoxide, 1,2,3,4-tetramethylbutyl hydroperoxide, and combinations thereof. The free radical polymerization initiator may comprise an encapsulated peroxide.

[0068] In addition to or in place of those described above, the composition of the present invention may further comprise a curing accelerator. For example, the curing accelerator may comprise one or more metallocenes, such as ferrocene, suitably n-butylferrocene. Advantageously, the presence of a curing accelerator promotes the curing of the composition of the present invention on a "non-active" or "passive" substrate (such as a plastic substrate).

[0069] The composition of the present invention may further comprise at least one solvent. The use of a solvent may be beneficial, for example, for formulation or distribution purposes. Suitably, at least one solvent may be selected from: ethyl acetate, tetrahydrofuran, dichloromethane, chloroform, or a combination thereof.

[0070] However, whenever weight percentages are used, they are based on the total weight of the composition without solvent.

[0071] Ideally, the solid thermoplastic polyvinyl butyral resin is soluble in various solvents or combinations thereof that can be used during the formulation or manufacturing process, such as ethyl acetate, at room temperature and above. Advantageously, the use of a solid thermoplastic polyvinyl butyral resin with high solubility (e.g., in ethyl acetate) can avoid some practical problems commonly encountered during manufacturing, especially on a large scale. For example, the use of a solid thermoplastic polyvinyl butyral resin with high solubility can eliminate the risk of gelling of the composition of the present invention during the manufacturing process or during storage.

[0072] Suitably, the composition of the present invention can be provided in any suitable solid form, including tape form, silk form or as a coating applied to a substrate, the substrate including, for example, silk or thread made of other materials such as nylon or polyester thread. The tape or silk of the solid composition can be less than 100 microns (μm) thickness. The tape or silk can be applied by winding (that is, in a similar manner to the current PTFE tape or thread-sealing rope used to seal joints in pipeline engineering). It should be understood that the solid form can be a desired pattern or arrangement, including rods, tapes, silk, washers or patches. The composition in its solid form (such as tape form or silk form) can have integrity sufficient to be handled without rupture. The composition in its solid form (such as tape form or silk form) can be applied to a substrate (such as a metal bolt) at room temperature. The composition in its solid form (such as tape form or silk form) can be heat resistant at a temperature of at least 150°C, such as at least 180°C, such as 200°C. This means that the composition is robust enough to maintain performance at the temperature of a common industrial environment. Even at elevated temperatures, the composition in its solid form (such as tape form or silk form) can be non-sticky and dry to the touch, thereby eliminating the need for a carrier, such as a release liner. The tape form or silk composition can be rolled up on itself and will not adhere to itself because it is non-sticky and dry to the touch. Alternatively, the tape form or silk form may contain the anaerobically curable composition of the present invention and one or more release liners. For example, when the temperature when the composition is to be stored is above 40° C., the release liner may be useful because the non-sticky composition may become sticky and may adhere to itself at temperatures above 40° C. As mentioned above, the composition of the present invention may also be in any suitable solid form, including tape form, silk form, or as a (solid, dry to the touch) coating applied to a substrate (including, for example, silk or thread made of other materials such as nylon or polyester thread).

[0073] Another aspect of the present invention provides a cured composition formed by curing the curable composition of the present invention claimed herein. Suitably, the curable composition can be cured by exposure to an anaerobic environment. The curable composition can be cured, for example, by being exposed to an anaerobic environment for about 1 minute to 30 minutes, such as a period in the range of about 1 minute to about 20 minutes. Optionally, the curable composition can be cured in a temperature range of about 40°C to about 100°C. For example, the curable composition can be cured by being exposed to an anaerobic environment for about 1 minute to about 30 minutes in a temperature range of about 40°C to about 100°C.

[0074] Once cured, the compositions of the present invention advantageously exhibit breakaway torque values ​​greater than 10 Nm for black oxide mild steel or zinc phosphate substrates when evaluated for M10 nuts and bolts according to ISO 10964. In addition, when evaluated for zinc phosphate M10 nuts and bolts according to ISO 10964, the cured compositions of the present invention advantageously exhibit break loose torque values ​​greater than 10 Nm at temperatures up to 180°C, for example at 50°C, 80°C, 120°C, 150°C, or 180°C.

[0075] In another aspect, the present invention provides a threaded member comprising at least one thread face, wherein the at least one thread face comprises an anaerobically curable composition of the present invention. For example, the anaerobically curable composition may be in the form of a tape or a filament. Alternatively, it may be in the form of a composition applied to / coated on a thread made of different materials. The tape, thread or fiber may be applied to the thread face, for example by wrapping the tape, thread or fiber at least partially around the thread face. For example, the anaerobically curable composition may be coated on a thread or fiber made of different materials to form a coated thread or fiber. The coated thread or fiber may be applied to the thread face, for example by wrapping the coated thread or fiber at least partially around the thread face.

[0076] In yet another aspect, the present invention provides a method for manufacturing a threaded component comprising a thread locking composition, the method comprising: providing at least one threaded component comprising at least one threaded face, applying the anaerobically curable composition of the present invention to the at least one threaded face. Suitably, the anaerobically curable composition is applied to at least one threaded face in the form of a tape, a filament, or as a coating applied to a substrate (such as a wire form or fiber formed of a different material), for example, the tape, filament, or coated substrate may be at least partially wrapped around at least one threaded face of the threaded component. Suitably, the anaerobically curable composition of the tape form, filament, or coated substrate may be non-sticky and dry to the touch, so that no carrier such as a release liner is required.

[0077] In yet another aspect, the present invention provides a method of assembling threaded components, the method comprising: providing a first threaded component comprising at least one thread face; applying the anaerobically curable composition of the present invention to the at least one thread face; providing a second threaded component capable of matingly engaging the first threaded component; matingly engaging the first and second threaded components and thereby exposing the anaerobically curable composition to an anaerobic environment for a time sufficient to cure the anaerobically curable composition between the first and second threaded components.

[0078] A method of manufacturing a tape, wire, or fiber for thread locking is also provided, the method comprising the steps of:

[0079] (i) mixing at least one solid thermoplastic polyvinyl butyral resin and a solvent, the solid thermoplastic polyvinyl butyral resin optionally having a molecular weight Mw in the range of about 40,000 g / mol to about 250,000 g / mol, suitably in the range of about 40,000 g / mol to about 170,000 g / mol, such as about 40,000 g / mol to 120,000 g / mol, for example 50,000 g / mol to 80,000 g / mol, wherein the molecular weight Mw is determined according to ASTM D5296-05, and optionally having a softening point of 80°C to about 300°C, suitably about 100°C to about 250°C, preferably about 140°C to about 200°C; suitably wherein the solvent may be selected from ethyl acetate, tetrahydrofuran, dichloromethane, chloroform, or combinations thereof;

[0080] (ii) mixing the above mixture with a liquid anaerobic curable component, a solid anaerobic curable component and a curing component for curing the anaerobic curable component; optionally adding an additive to the mixture; so as to form an anaerobic curable composition;

[0081] (iii) forming the mixture into a desired form, for example by casting or extruding the mixture and / or applying it to a carrier such as a threaded article or a release liner;

[0082] The solvent is removed and / or allowed to evaporate, thereby forming a tape, thread, or fiber comprising the anaerobically curable composition of the present invention and an optional carrier. DETAILED DESCRIPTION

[0083] As summarized above, the present invention provides an anaerobic curable composition comprising: a liquid anaerobic curable component; a solid anaerobic curable component; a solid thermoplastic polyvinyl butyral resin; and a curing component for curing the anaerobic curable component.

[0084] Definitions and Standard Test Methods

[0085] The term "liquid" means liquid in the temperature range of about 5°C to 30°C, suitably liquid at room temperature and atmospheric pressure.

[0086] The term "solid" means solid in the temperature range of about 5°C to 40°C, suitably solid at room temperature and atmospheric pressure. The solid state is defined as a state of matter in which the material is not fluid but holds its boundaries without support, with atoms or molecules occupying fixed positions relative to each other and not free to move.

[0087] For purposes of the present invention, tack-free means dry to the touch, but the composition will not flake off during handling or use. For example, an article to which the composition of the present invention is applied is dry to the touch. An article to which the composition of the present invention has been applied is considered dry to the touch if 20 such articles are placed individually on a dry tissue for four hours and the appearance of the tissue does not change.

[0088] The molecular weights disclosed herein are determined according to ISO 13885-1:2008, "Binders for paints and varnishes--Gel permeation chromatography (GPC)--Part 1: Tetrahydrofuran (THF) as eluent."

[0089] The melting and re-hardening temperature ranges are measured according to ISO 1137-1:2016 "Plastics - Differential scanning calorimetry (DSC) - Part 1 General Principles".

[0090] Liquid anaerobic curing components

[0091] Suitably, the liquid anaerobic curable component comprises a liquid (meth)acrylate monomer component.

[0092] The liquid (meth)acrylate component may include one or more (meth)acrylate monomers selected from the group consisting of β-carboxyethyl acrylate, isobornyl acrylate, n-octyl acrylate, n-decyl acrylate, cyclohexyl acrylate, tetrahydrofurfuryl acrylate, 2-ethylhexyl acrylate, ethoxyethoxyethyl acrylate, ethoxylated phenyl monoacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, isooctyl acrylate, n-butyl acrylate, neopentyl glycol diacrylate, ethylene glycol diacrylate, diethylene glycol diacrylate, dipropylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, 1,6-hexanediol diacrylate, tripropylene glycol diacrylate, glycerol triacrylate, trimethylolpropane diacrylate, trimethylolpropane methacrylate, phenoxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, cyclohexyl methacrylate, glycerol monomethacrylate, glycerol 1,3-dimethacrylate, trimethylcyclohexyl methacrylate, methyl triethylene glycol methacrylate, isobornyl methacrylate, trimethylolpropane trimethacrylate, neopentyl glycol dimethacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, 1,6-hexanediol dimethacrylate, hydroxybutyl methacrylate, tetrahydrofurfuryl methacrylate, cyclohexyl methacrylate, phenoxyethyl methacrylate, glycerol methacrylate, glycidyl methacrylate, methyl methacrylate and methacrylic acid and mixtures thereof.

[0093] Preferred liquid (meth)acrylate monomers include 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, phenoxyethyl methacrylate, and methacrylic acid.

[0094] One or more suitable (meth)acrylates may be selected from multifunctional (meth)acrylates such as, but not limited to, difunctional or trifunctional (meth)acrylates, such as polyethylene glycol di(meth)acrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate ("TRIEGMA"), tetraethylene glycol dimethacrylate, dipropylene glycol dimethacrylate, di-(pentylene glycol) dimethacrylate, tetraethylene diglycol diacrylate, diglycerol tetramethacrylate, tetramethylene dimethacrylate, ethylene dimethacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate, polyethylene glycol di(meth)acrylate, and bisphenol-A mono- and di(meth)acrylates, such as ethoxylated bisphenol-A (meth)acrylate ("EBIPMA"), and bisphenol-F mono- and di(meth)acrylates, such as ethoxylated bisphenol-F (meth)acrylate.

[0095] For example, the redox curable component may include bisphenol A dimethacrylate:

[0096]

[0097] Suitably, the redox curable composition may include ethoxylated bisphenol A di(meth)acrylate.

[0098] Other (meth)acrylates that may be suitable for use herein are silicone (meth)acrylate moieties ("SiMA") such as those taught and claimed in US Pat. No. 5,605,999 (Chu), the disclosure of which is hereby expressly incorporated herein by reference.

[0099] Other suitable materials may be selected from polyacrylates represented by the following formula:

[0100]

[0101] Where R 4 is a group selected from hydrogen, halogen or an alkyl group of 1 to about 4 carbon atoms; q is an integer equal to at least 1, and preferably equal to 1 to about 4; and X is an organic group containing at least two carbon atoms and a total bonding capacity of q+1. Regarding the upper limit of the number of carbon atoms in X, feasible monomers exist at essentially any value. However, for practical purposes, the general upper limit is about 50 carbon atoms, such as advantageously about 30, and advantageously about 20.

[0102] For example, X may be an organic group of the formula:

[0103]

[0104] where Y 1 and Y 2 Each is an organic group, such as a hydrocarbon group, containing at least 2 carbon atoms, and advantageously 2 to about 10 carbon atoms, and Z is an organic group, preferably a hydrocarbon group, containing at least 1 carbon atom, and preferably 2 to about 10 carbon atoms. Other materials can be selected from the reaction products of di- or tri-alkanolamines (e.g., ethanolamine or propanolamine) and acrylic acid, as disclosed in French Patent No. 1,581,361.

[0105] Suitable oligomers having (meth)acrylate functional groups may also be used. Examples of such (meth)acrylate functional oligomers include those having the following general formula:

[0106]

[0107] Where R 5 represents a group selected from hydrogen, an alkyl group having 1 to about 4 carbon atoms, a hydroxyalkyl group having 1 to about 4 carbon atoms, or a group of the formula

[0108]

[0109] Where R 4 is a group selected from hydrogen, halogen, or an alkyl group of 1 to about 4 carbon atoms; R 6 is selected from hydrogen, hydroxyl, or a group of the formula

[0110]

[0111] m is an integer equal to at least 1, such as 1 to about 15 or more, and advantageously an integer from 1 to about 8; n is an integer equal to at least 1, such as 1 to about 40 or more, and advantageously an integer from about 2 to about 10; and p is 0 or 1.

[0112] Typical examples of acrylate oligomers corresponding to the above general formula include di-, tri- and tetraethylene glycol dimethacrylates; di(pentylene glycol) dimethacrylate; tetraethylene glycol diacrylate; tetraethylene glycol di(chloroacrylate); diglycerol diacrylate; diglycerol tetramethacrylate; butanediol dimethacrylate; neopentyl glycol diacrylate; and trimethylolpropane triacrylate.

[0113] While diacrylates and other multiacrylates, and particularly the multiacrylates described in the preceding paragraphs, may be desirable, monofunctional acrylates (esters containing one acrylate group) may also be used.

[0114] Suitable compounds may be selected from cyclohexyl methacrylate, tetrahydrofurfuryl methacrylate, hydroxyethyl acrylate, hydroxypropyl methacrylate, tert-butylaminoethyl methacrylate, cyanoethyl acrylate and chloroethyl methacrylate.

[0115] Another useful class of materials are the reaction products of (meth)acrylate functionalized hydroxyl or amino containing materials and polyisocyanates in suitable proportions to convert all of the isocyanate groups to urethane or urea groups, respectively.

[0116] The (meth)acrylate urethane or urea thus formed may contain hydroxyl or amino functional groups on the non-acrylate portion thereof. Suitable (meth)acrylates for use may be selected from those of the following formula:

[0117]

[0118] Where X is selected from --O-- and

[0119]

[0120] Where R 9 is selected from hydrogen or a lower alkyl group of 1 to 7 carbon atoms; R7 is selected from hydrogen, halogen (such as chlorine) or alkyl (such as methyl and ethyl groups); and R 8 It is a divalent organic group selected from an alkylene group having 1 to 8 carbon atoms, a phenylene group and a naphthylene group.

[0121] These groups, when appropriately reacted with polyisocyanates, produce monomers of the general formula:

[0122]

[0123] wherein n is an integer from 2 to about 6; B is a polyvalent organic group selected from substituted and unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, alkaryl, alkaryl and heterocyclic groups and combinations thereof; and R 7 , R 8 and X have the meanings given above.

[0124] Depending on the nature of B, these (meth)acrylates having urea or urethane linkages can have molecular weights that place them in the oligomeric category (eg, about 1,000 g / mol to about 5,000 g / mol) or in the polymeric category (eg, about greater than 5,000 g / mol).

[0125] Other unsaturated reactive monomers and oligomers may be used, such as styrene, maleimide, vinyl ether, allyls, allyl ethers, and those mentioned in US6844080B1 (Kneafsey et al.). Vinyl resins such as those mentioned in US6433091 (Xia) may also be used. Methacrylate or acrylate monomers containing these unsaturated reactive groups may also be used.

[0126] Of course, combinations of these (meth)acrylates and other monomers may also be used.

[0127] Solid anaerobic curable components

[0128] The anaerobically curable composition of the present invention comprises a solid anaerobically curable component. The solid anaerobically curable component may be a solid (meth)acrylate resin. Suitably, the solid (meth)acrylate resin is selected from the list of suitable (meth)acrylate components listed above.

[0129] Solid thermoplastic polyvinyl butyral resin

[0130] The anaerobic curable composition of the present invention comprises a solid thermoplastic polyvinyl butyral resin. The molecular weight Mw of the solid thermoplastic polyvinyl butyral resin may be in the range of about 40,000 g / mol to about 250,000 g / mol, suitably in the range of about 40,000 g / mol to about 170,000 g / mol, such as about 40,000 g / mol to 120,000 g / mol, for example 50,000 g / mol to 80,000 g / mol, wherein the molecular weight Mw is determined according to ASTM D5296-05. The softening point of the solid thermoplastic polyvinyl butyral resin may be in the range of about 80°C to about 300°C, suitably about 100°C to about 250°C, preferably about 140°C to about 200°C. Suitable solid thermoplastic polyvinyl butyral resins include those available from Eastman B-79. B-79 is a solid thermoplastic polyvinyl butyral resin having a molecular weight of 50,000-80,000 (size exclusion chromatography using low angle laser light scattering standards) and a softening point in the range of 140-200°C. Other suitable commercially available solid thermoplastic polyvinyl butyral resins may include B-72, B-74, B-76, B-90 and B-98 (available from Eastman).

[0131] The anaerobically curable compositions provided in Table 1 were formulated in tape form.

[0132]

[0133]

[0134] The composition of Table 1 was prepared as follows:

[0135] Solid thermoplastic polyvinyl butyral resin was dissolved in ethyl acetate at room temperature and then transferred to a Speedmixer. TM DAC150.147. The remaining components are then added and mixing continued until the individual components are dissolved. For compositions containing microencapsulated peroxides or methacrylates, the encapsulated components will not dissolve and mixing is continued until the microencapsulated components form a dispersion in the solution. Then, an Elcometer coating plate temperature maintained at 30°C is used. TM Each solution was cast onto a siliconized polyester release liner (HiFi SR4-122, 75 micron thick) using a 4340 automatic film coater. After coating, the ethyl acetate was evaporated by passing it through a heated coating plate. A dry-to-touch film was obtained.

[0136] The thread locking properties of the films formed from Example Composition 1 were evaluated at elevated temperatures on fixed zinc phosphate nuts and bolts according to ISO 10964. The composition of the invention was applied to an M10 bolt and a threaded assembly with a torque of 5 Nm was formed with an M10 nut capable of matingly engaging the M10 bolt. The threaded assembly was maintained at 22°C for one week before measuring the fracture and primary strength of the cured composition within the temperature range specified below. The results are shown in Table 2.

[0137]

[0138] *Results are average of 4 runs

[0139] The thread locking properties of films formed from Example Compositions 2 and 3 were evaluated at elevated temperatures for fixed zinc phosphate bolts and mild steel nuts according to ISO 10964. The composition of the invention was applied to an M10 bolt and a threaded assembly with a torque of 5 Nm was formed with an M10 nut capable of matingly engaging the M10 bolt. The threaded assembly was maintained at 22°C for the specified time before measuring the fracture and primary strength of the cured composition within the temperature range specified below. The results are shown in Table 3.

[0140]

[0141] *Results are average of 4 runs

[0142] The thread locking performance of each film formed from Example Compositions 1-4 was evaluated on M10 nuts and bolts of various substrates. The threaded assemblies were formed as described above and cured at 22° C. for 24 hours before measuring the fracture and primary strength of the cured compositions. The results for each composition are provided in Table 4.

[0143]

[0144] The threadlocking properties of each of the films formed from Example Compositions 1 and 2 were measured after heat aging.

[0145] As described above, a threaded assembly of a film formed of Example Composition 1 was formed on a fixed zinc phosphate nut and bolt, with a torque of 5 Nm. The threaded assembly was kept at 22°C for 1 week for curing and then aged at the specified temperature for 1000 hours. The fracture and primary strength of the cured composition were then measured as described above. The results are shown in Table 5.

[0146]

[0147] *Results are averages of 5 runs

[0148] As described above, a threaded assembly of a film formed of Example Composition 2 was formed on a fixed zinc phosphate bolt and a mild steel nut, with a torque of 5 Nm. The threaded assembly was kept at 22°C for 1 week for curing and then aged for 2000 hours at the specified temperature. The fracture and primary strength of the cured composition were then measured as described above. The results are shown in Table 6.

[0149]

[0150] *Results are averages of 5 runs

[0151] When used herein in conjunction with the present invention, the words “comprises / comprising” and the words “having / including” are used to specify the presence of stated features, integers, steps or components, but do not exclude the presence or addition of one or more other features, integers, steps, components or groups thereof.

[0152] It should be understood that certain features of the present invention described in the context of separate embodiments for clarity may also be provided in combination in a single embodiment. Conversely, various features of the present invention described in the context of a single embodiment for brevity may also be provided separately or in any suitable sub-combination.

Claims

1. An anaerobic curable composition comprising: Liquid anaerobically curable components; Solid anaerobically curable components; Solid thermoplastic polyvinyl butyral resin; and A curing component for curing the anaerobic curable component.

2. The composition according to claim 1, wherein the molecular weight Mw of the solid thermoplastic polyvinyl butyral resin is in the range of about 40,000 g / mol to about 250,000 g / mol, suitably in the range of about 40,000 g / mol to about 170,000 g / mol, such as about 40,000 g / mol to 120,000 g / mol, for example 50,000 g / mol to 80,000 g / mol, wherein the molecular weight Mw is determined according to ASTM D5296-05.

3. A composition according to any one of the preceding claims, wherein the solid thermoplastic polyvinyl butyral resin has a softening point in the range of about 50°C to about 300°C, suitably about 100°C to about 250°C, preferably about 140°C to about 200°C.

4. A composition according to any one of the preceding claims, wherein the liquid anaerobically curable component is present in an amount of about 5 wt % to about 50 wt % based on the total weight of the composition, suitably about 10 wt % to about 40 wt %, such as about 30 wt % based on the total weight of the curable composition.

5. A composition according to any one of the preceding claims, wherein the solid anaerobically curable component is present in an amount of about 6 wt % to about 50 wt % based on the total weight of the composition, suitably about 10 wt % to about 25 wt %, such as about 13 wt % based on the total weight of the curable composition.

6. A composition according to any one of the preceding claims, wherein the solid thermoplastic polyvinyl butyral resin is present in an amount of about 10 wt % to about 50 wt % based on the total weight of the composition, suitably about 15 wt % to about 40 wt %, such as about 15 wt % to about 35 wt %, for example about 20 wt %, based on the total weight of the curable composition.

7. The composition according to any one of the preceding claims, wherein the curing component for curing the anaerobically curable component is present in an amount of about 0.1 to about 10 wt %, such as about 1 to about 5 wt %, based on the total weight of the curable composition.

8. The composition of any one of the preceding claims, wherein the liquid anaerobically curable component comprises a liquid (meth)acrylate monomer component.

9. The composition according to claim 8, wherein the liquid (meth)acrylate monomer component is one or more selected from those having the following formula: H 2 C=CGCO 2 R 8 , wherein G is hydrogen, halogen or an alkyl group having 1 to 4 carbon atoms, and R 8 Selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, alkaryl or aryl groups having from 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted by silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, carbamate, carbonate, amine, amide, sulfur, sulfonate, sulfone, etc., as the case may be.

10. The composition of any preceding claim, wherein the solid anaerobically curable component comprises one or more solid (meth)acrylate monomer components.

11. The composition according to any one of the preceding claims, wherein the curing component comprises one or more selected from the group consisting of 1-acetyl-2-phenylhydrazine, N,N-dimethyl-p-toluidine, N,N-diethyl-p-toluidine, N,N-diethanol-p-toluidine, N,N-dimethyl-o-toluidine, N,N-dimethyl-m-toluidine, indoline, 2-methylindoline, isoindoline, indole, 1,2,3,4-tetrahydroquinoline, 3-methyl-1,2,3,4-tetrahydro-quinoline, 2-methyl-1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroquinoline-4-carboxylic acid, and 1,2,3,4-tetrahydro-benzo(H)quinolin-3-ol.

12. A composition according to any preceding claim further comprising a free radical polymerisation initiator, such as a peroxide.

13. The composition of claim 12, wherein the free radical polymerization initiator is one or more selected from the group consisting of cumene hydroperoxide ("CHP"), terpane hydroperoxide, tert-butyl hydroperoxide ("TBH"), tert-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1,3-bis(tert-butylperoxyisopropyl)benzene, diacetyl peroxide, 4,4-bis(tert-butylperoxy)butyl valerate, p-chlorobenzoyl peroxide, tert-butylcumene peroxide, tert-butyl perbenzoate, di-tert-butyl peroxide, diisopropylbenzene peroxide, 2,5-dimethyl-2,5-di-tert-butylhexylperoxide, 2,5-dimethyl-2,5-di-tert-butyl-peroxyhex-3-yne, 4-methyl-2,2-di-tert-butylpentane, tert-amyl hydroperoxide, 1,2,3,4-tetramethylbutyl hydroperoxide, and combinations thereof.

14. A composition according to claim 12 or 13, wherein the free radical polymerization initiator comprises an encapsulated peroxide.

15. The composition of any preceding claim further comprising a cure accelerator.

16. A composition according to claim 15, wherein the curing accelerator comprises one or more metallocenes, such as ferrocene, suitably n-butylferrocene; and / or The curing accelerators are covered by the following formula: wherein X is CH 2 , O, S, NR 4 , CR 5 R 6 or C═O; R is one or more of hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynyl; R 1 -R 6 are each independently selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; R 7 is hydrogen or CHR 8 R 9 , wherein R 8 and R 9 are each independently selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; and n is 0 or 1.

17. A composition according to any preceding claim provided in tape form, filament form or in the form of a coated substrate.

18. A composition according to any one of claims 1 to 16 provided as a coating on a thread or fibre.

19. A tape comprising an anaerobically curable composition according to any one of the preceding claims and one or more release liners.

20. A threaded component comprising at least one thread face, wherein the at least one thread face comprises an anaerobically curable composition according to any one of claims 1 to 18, optionally wherein the anaerobically curable composition is in the form of a tape, filament or a coated substrate, and optionally wherein the anaerobically curable composition in the form of a tape, filament or a coated substrate is applied to the thread face, for example by wrapping the tape at least partially around the thread face.

21. A method for manufacturing a threaded component comprising a thread locking composition, wherein include: a. providing at least one threaded member comprising at least one threaded surface, b. applying anaerobically curable composition according to any one of claims 1 to 17 to said at least one threaded face.

22. A method for manufacturing a threaded member according to claim 21, wherein the anaerobically curable composition is in the form of a tape, a filament or a coated substrate, and optionally wherein the anaerobically curable composition in the form of a tape, a filament or a coated substrate is at least partially wrapped around the at least one thread face of the threaded member.

23. A method of assembling a threaded member, wherein include: (a) providing a first threaded member, wherein the first threaded member comprises at least one thread surface; (b) applying an anaerobic curable composition according to any one of claims 1 to 17 to the at least one threaded surface; (c) providing a second threaded member capable of matingly engaging the first threaded member; The first and second threaded members are matingly engaged and the anaerobically curable composition is thereby exposed to an anaerobic environment for a time sufficient to cure the anaerobically curable composition between the first and second threaded members.

24. The method of claim 23, wherein the anaerobically curable composition is in the form of a tape, a filament, or a coated substrate, and optionally wherein the anaerobically curable composition in the form of a tape, a filament, or a coated substrate is at least partially wrapped around the at least one thread face.

25. A method of making a tape, wire, or fiber for thread locking, wherein The following steps are involved: (i) mixing at least one solid thermoplastic polyvinyl butyral resin and a solvent, the solid thermoplastic polyvinyl butyral resin optionally having a molecular weight Mw in the range of about 40,000 g / mol to about 250,000 g / mol, suitably in the range of about 40,000 g / mol to about 170,000 g / mol, such as about 40,000 g / mol to 120,000 g / mol, for example 50,000 g / mol to 80,000 g / mol, wherein the molecular weight Mw is determined according to ASTM D5296-05, and optionally having a softening point of 80°C to 300°C, such as 100°C to 250°C, for example 140°C to 200°C; suitably wherein the solvent is selected from tetrahydrofuran, dichloromethane, chloroform, ethyl acetate, or a combination thereof; (ii) mixing the above mixture with a liquid anaerobic curable component, a solid anaerobic curable component and a curing component for curing the anaerobic curable component; optionally adding an additive to the mixture; so as to form an anaerobically curable composition; (iii) forming the mixture into a desired form, for example by casting and / or applying the mixture onto a support such as a threaded article or a release liner; The solvent is removed and / or evaporated to form a tape, thread, or fiber comprising the anaerobically curable composition and, optionally, a carrier.

Images