Anaerobic curing composition

Abstract

Liquid anaerobic curing component, solid anaerobic hardening component, solid polyether polyvinyl butyral resin, and a curing component for curing the anaerobic curing component; 1. An anaerobic curable composition comprising: Advantageously, the compositions of the present invention are substantially solid and may be used as threadlockers.

Description

[Technical Field]

[0001] The present invention relates to an anaerobic curing composition that can be used in many applications, including thread locking. The composition is substantially solid and may be provided in any suitable solid form, such as a tape, filament, or coating applied to a substrate, including filaments or threads made from other materials, such as nylon or polyester threads. The present invention also relates to methods for preparing threaded fasteners and methods for assembling threaded fasteners. The composition is easily handled and can be applied to threaded members. The composition is heat resistant to temperatures of at least 150°C. [Background technology]

[0002] Thread locking compositions are used to lock and / or seal threaded fasteners, such as nuts and bolts, in their interlocking states. Such thread locking compositions significantly increase the torque required to break or turn the mating threaded fasteners. Conventional thread locking compositions often include co-reactive adhesive systems, in which two or more components are mixed together and the resulting composition is applied to the mating thread surfaces of a fastener, where the components of the thread locking composition react and harden. Examples of such co-reactive systems include epoxy resin adhesive compositions.

[0003] Liquid adhesive compositions have been used for many years for sealing and thread-locking applications and have become a standard part of assembly production as well as the maintenance of machinery, tools, etc. Among the liquid adhesive compositions commonly used in these applications are anaerobic compositions. These compositions provide excellent thread-locking and sealing properties upon curing. Anaerobic-curing compositions applied to threaded fasteners as thread-locking compositions remain in a stable (uncured) or liquid state until placed between the mated threaded fasteners and cured in the absence of oxygen.

[0004] Anaerobic curing compositions are generally well known. See, for example, R.D. Rich, "Anaerobic Adhesives," Handbook of Adhesives Technology, Vol. 29, pp. 467-79, edited by A. Pizzi and K.L. Mittal, Marcel Dekker, Inc., New York (1994), and references cited therein. Their uses are numerous, and new applications are continually being developed.

[0005] Anaerobic adhesive systems are stable in the presence of oxygen but polymerize in its absence. Polymerization is often initiated by the presence of free radicals generated from peroxide compounds. Anaerobic adhesive compositions are well known for their ability to maintain a liquid, non-polymerized state in the presence of oxygen and cure to a solid state upon the exclusion of oxygen.

[0006] Anaerobic adhesive systems often contain resin monomers terminated with polymerizable acrylate esters such as methacrylate, ethyl acrylate, and chloroacrylate esters 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 components typically included in anaerobically curable adhesive compositions include initiators such as organic hydroperoxides such as cumene hydroperoxide, tertiary butyl hydroperoxide, etc.; accelerators to increase the cure rate of the composition; and stabilizers such as quinones or hydroquinones to help prevent premature polymerization of the adhesive due to decomposition of the peroxide compounds.

[0007] Desirable cure-inducing compositions for inducing and accelerating anaerobic cure include one or more of saccharin, toluidine (e.g., N,N-diethyl-p-toluidine ("DE-pT") and N,N-dimethyl-o-toluidine ("DM-oT")), and acetylphenylhydrazine ("APH") with maleic acid. See, e.g., U.S. Patent Nos. 3,218,305 (Crieble), 4,180,640 (Melody), 4,287,330 (Rich), and 4,321,349 (Rich).

[0008] Saccharin and APH are standard accelerator components in anaerobic adhesive cure systems. In fact, many of Henkel's current Loctite® brand anaerobic adhesive products use either saccharin alone or both.

[0009] Anaerobic curing adhesive compositions also typically include a chelating agent such as ethylenediaminetetraacetic acid (EDTA) that is used to sequester metal ions.

[0010] Compositions suitable for pre-applied threadlocking applications are typically applied in a dry-to-the-touch state, but have anaerobic curing capabilities at a later stage.

[0011] In some cases, a dry-to-the-touch state is achieved using a curing mechanism, for example, a first curing mechanism creates a dry-to-the-touch state to hold the composition in place on the article, after which a second curing mechanism is activated to achieve thread lock.

[0012] For example, European Patent No. 0077659 (Thompson) describes a pre-applied polymerizable fluid for sealing and securing engineering components. This composition has two mechanisms for curing, resulting in two curing reactions. The first mechanism is ultraviolet curing. An opacifying agent is dispersed in the fluid, rendering the fluid substantially opaque to radiation. After the fluid is applied to a component, exposure to UV radiation forms a coating, forming a surface layer that is a dry, tack-free crust. The liquid underneath remains unaffected by the radiation and remains largely liquid. When the component is screwed onto another component, the surface layer breaks, initiating a second polymerization (e.g., free radical polymerization). Once the threaded components interlock and an anaerobic environment is established, a second curing reaction occurs. The second polymerization mechanism serves to secure the threads together. In Thompson, only the top layer forms during the first polymerization, while the remaining composition remains liquid beneath the top layer. Therefore, there is a risk that the top layer may break during handling of the coated engineering component, resulting in leakage of the liquid composition.

[0013] Similarly, EP 0548369 (Usami) describes a pre-applied adhesive composition for application to the thread contact surfaces of threaded components such as screws. The composition comprises a photocurable binder having dispersed therein a secondary curable composition, which includes a microencapsulated reactive monomer / activator / initiator.

[0014] International Patent Publication WO 2004 / 024841 A2 (Haller) describes a curable composition for application to a screw article. The composition includes components of a first cure mechanism, including (a) a (meth)acrylate-functional monomer component, (b) a (meth)acrylate-functional oligomer component, and (c) a photoinitiator component; (ii) a dispersion of components of a second cure mechanism, including (e) an amine component and (f) an encapsulated epoxy resin component; and (iii) a thickener component. The photoinitiator component is suitable for achieving a first cure throughout the depth of the composition applied to the screw article upon irradiation of the composition, forming a binder matrix with the components of the second cure mechanism dispersed throughout the matrix.

[0015] U.S. Patent No. 9,181,457 (Attawalla) describes dry-feel compositions containing a polymer matrix and an anaerobic curing component present within the polymer matrix. In a particularly desirable form, the compositions are moisture-curable. The compositions do not flow at elevated temperatures and exhibit improved solvent resistance after curing. The compositions are useful as threadlocking compositions and can be formulated as coatings on carrier substrates such as tapes, strips, or sheets.

[0016] British Patent No. 2,543,756 (Ledwis) describes a threadlocking composition comprising an anaerobic curable component and a curing component that cures the anaerobic curable component, the composition being in the form of flowable particles and having a melting point in the range of 30 to 100°C. The anaerobic curable component may comprise an anaerobic curable monomer and a resin component. The composition may be provided in at least two parts. The anaerobic curable component is preferably provided in powder form. The resin component is preferably selected from methacrylated polyurethane resins, novolac resins, or higher methacrylated polyester resins. The anaerobic curable monomer preferably contains at least one acrylate or methacrylate ester group. The composition is preferably solvent-free. Also disclosed is a method for threadlocking two threaded articles, which comprises applying the composition to the threads of at least one article, melting and fusing the composition to the threads, and then, after optional cooling, screwing the two articles together and initiating anaerobic curing of the threadlocking composition to chemically bond the two articles. Articles having the compositions are also disclosed.

[0017] U.S. Patent Application Publication No. 4,039,705 (Douk) relates to an anaerobic-curing pressure-sensitive adhesive stock, such as sheets and tapes, in which the pressure-sensitive adhesive layer obtained from the stock contains at least one anaerobic resin system that is completely transferred to one substrate for bonding to another substrate and cured by activation with a peroxide initiator and exclusion of oxygen. The anaerobic pressure-sensitive adhesive is contained between two different release surfaces, allowing the pressure-sensitive adhesive to be transferred to a substrate that is firmly secured to another substrate upon curing of the anaerobic-curing pressure-sensitive adhesive.

[0018] While traditional anaerobic threadlockers have been and remain popular in the marketplace, certain drawbacks to their use in commercial applications have been observed with traditional liquid anaerobic threadlockers and known non-flowing thixotropic anaerobic-based threadlockers. For example, these compositions often do not fully cure across large gaps. Furthermore, because they are anaerobic-curing, the portions of the adhesive that remain exposed to air after application to a part are less likely to cure (unless an induced secondary cure mechanism exists). Therefore, external bondlines that remain exposed to air on nut / bolt assemblies often remain liquid unless additional additives and curing measures are applied to ensure cure. As a result, the liquid composition in the external bondline tends to migrate. In the case of traditional non-flowing compositions, their non-flowability relies on the thixotropic and / or rheological properties of the composition, which will flow if exposed to sufficiently high temperatures. Furthermore, the solvent resistance of cured products (which still have uncured portions, as described above) can be poor, indicating questionable integrity when interacting with the environment. This can lead to contamination issues and potentially dangerous conditions for the surrounding environment.

[0019] Despite the state of the art, it is desirable to provide alternative thread locking systems, including threaded members that include dry feel thread locking compositions, methods of forming such threaded members, and methods of assembling such threaded members. Summary of the Invention

[0020] In one aspect, the present invention provides a method for producing a medicament for the treatment of a pulmonary arthritis. Liquid anaerobic hardening component; Solid anaerobic hardening components; solid thermoplastic polyvinyl butyral resin; and Hardening component for hardening anaerobic hardening components The present invention provides an anaerobic curable composition comprising:

[0021] 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 for any suitable application.For example, they can be provided on a screw article in a solid form, provided in a screw form, or provided in a tape form.The compositions of the present invention can be provided on a carrier or can be in a self-supporting form.

[0022] The solid thermoplastic polyvinyl butyral resin may have a softening point ranging from about 50°C to about 300°C, suitably from about 100°C to about 250°C, and preferably from about 140°C to about 200°C. The solid thermoplastic polyvinyl butyral resin may function as a film former. The use of a solid thermoplastic polyvinyl butyral resin having a high softening point, such as from about 140°C to about 200°C, is believed to impart good heat resistance to the resulting composition, enabling it to function well at high temperatures. For example, the composition of the present invention in the form of a tape is suitable for applications at high temperatures of 100°C, 150°C, or even higher.

[0023] The solid thermoplastic polyvinyl butyral resin may have 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, for example, about 40,000 g / mol to 120,000 g / mol, e.g., 50,000 g / mol to 80,000 g / mol, where Mw is measured in accordance with ASTM D5296-05 (Standard Test Method for Molecular Weight Average and Molecular Weight Distribution of Polystyrene by High Performance Size Exclusion Chromatography).

[0024] The liquid anaerobic curable component can 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, for example, about 30 wt% based on the total weight of the curable composition. If 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 not move sufficiently, for example, it may not move into the space between interlocking threaded surfaces, may have poor thread locking performance, or may have poor adhesive performance. If 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 part may be adversely affected, the composition may become too flowable / soft, and for example, a coating formed by the composition may easily rupture when contacted with other surfaces, such as the surface of processing equipment, or other substrates, including other substrates that may be coated with a coating. When the liquid anaerobic 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 between threadlocking and / or adhesive performance and the composition curing to form a coating with sufficient integrity and good bond strength required for application of the composition to the parts to be bonded and the bond strength required for the adhesive end use.

[0025] The solid anaerobic curable component may 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, for example, about 13% by weight based on the total weight of the curable composition. Compositions containing less than about 6% by weight of the solid anaerobic curable component tend to lack cohesive strength and may not be suitable for application onto parts. For example, coatings formed by such compositions may easily fracture upon contact with other surfaces, such as surfaces of handling equipment, or other substrates, including other substrates that may be coated. Compositions containing more than about 50% by weight of the solid anaerobic curable component tend to form coatings that are too brittle for application to bonded parts. When the 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 the composition (when applied as a coating) with an acceptable balance between threadlocking and / or adhesive performance (when cured) and a composition that can be applied as a coating with sufficient integrity and strength.

[0026] The solid thermoplastic polyvinyl butyral resin may be present in an amount of about 10% to about 50% by weight, suitably about 15% to about 40% by weight, for example, about 15% to about 35% by weight, for example, about 20% by weight, based on the total weight of the curable composition. Compositions containing less than about 10% by weight of the solid thermoplastic polyvinyl butyral resin tend to have insufficient elastomeric properties to allow the composition to be properly applied to the parts to be bonded. Compositions containing more than about 50% by weight of the solid thermoplastic polyether polyurethane component tend to exhibit poor threadlock / adhesion properties. When the 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 threadlock and / or adhesive performance and the ability to form a coating with sufficient elastomeric properties to allow the composition to be applied to the parts to be bonded.

[0027] The curing component for curing the anaerobic curable component may be present in an amount of about 0.1 to about 10 wt % based on the total weight of the curable composition, for example, about 1 to about 5 wt % based on the total weight of the curable composition.

[0028] Suitably, the liquid anaerobic curable component comprises a liquid (meth)acrylate monomer component.

[0029] The liquid (meth)acrylate monomer component may be one or more selected from those having the following formula: H2C=CGCO2R 8 , where G is hydrogen, halogen, or an alkyl group having 1 to 4 carbon atoms; R 8 is selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, alkaryl, or aryl groups having 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted with silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbonate, amine, amide, sulfur, sulfonate, sulfone, and the like.

[0030] Suitably, the solid anaerobic curable component comprises one or more solid (meth)acrylate monomer components. For example, the solid anaerobic curable may be the reaction product of an isocyanate-containing compound, such as phenyl isocyanate, with a hydroxyl alkyl (meth)acrylate, such as hydroxyethyl methacrylate (HEMA).

[0031] [ka]

[0032] This is a 2-methacryloxylethyl urethane with a melting point of about 70-75°C.

[0033] The solid anaerobic curable component can also be the reaction product of two molar equivalents of HEMA with one molar equivalent of a diisocyanate, such as isophorone diisocyanate (IPDI), 4,4'-methylenebis(cyclohexyl isocyanate) (HMDI), or 1,5-cyclohexyl diisocyanate (CHDI). For example:

[0034] [ka]

[0035] This is HEMA-IPDI-HEMA, which has a melting point of about 72-74°C.

[0036] [ka]

[0037] This is HEMA-HMDI-HEMA, which has a melting point of about 75-85°C.

[0038] [ka]

[0039] This is HEMA-CHDI-HEMA, which has a melting point of about 75-85°C.

[0040] The solid anaerobic curing component can also be a polyurethane methacrylate resin with a molecular weight greater than 2000 g / mol and a semi-crystalline polyester polyol backbone. An example of such a resin is described in International Patent Publication WO 2017 / 68196 A1, which is the reaction product of a polyol known as Dynacol 7380 with toluene diisocyanate, then end-capped with HEMA. The melting points of these resins range from 50 to 80°C.

[0041] Novolac vinyl ester resins, which are the reaction products of novolac epoxy resins and methacrylic acid, are also used as solid anaerobic curing components. Examples of these resins and their preparation are shown in U.S. Patent No. 9,957,344. For example,

[0042] [ka]

[0043] In the formula, n is an integer of 2 to 10, and the compound has a melting point of about 70 to 75°C.

[0044] Suitably, the curing component comprises one or more selected from the group consisting of 1-acetyl-2-phenylhydrazine, N,N-dimethyl para-toluidine, N,N-diethyl para-toluidine, N,N-diethanol-para-toluidine, N,N-dimethyl orthotoluidine, N,N-dimethyl meta-toluidine, indoline, 2-methylindoline, isoindoline, indole, 1,2,3,4-tetrahydroquinoline, 3-methyl-1,2,3,4-tetrahydroquinoline, 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.

[0045] The anaerobic curable compositions of the present invention may include a cure accelerator encompassed by the formula:

[0046] [ka]

[0047] In the formula, X is CH2, O, S, NR 4 , C.R. 5 R 6 or C═O; R is one or more of hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynyl; R 1 ~R 6are 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 and 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.

[0048] Optionally, the above cure accelerators are used in combination with at least one co-accelerator selected from the group consisting of amines, amine oxides, sulfonamides, metal sources, acids, and mixtures thereof.

[0049] For example, the co-promoter may be selected from the group consisting of triazine, ethanolamine, diethanolamine, triethanolamine, N,N-dimethylaniline, benzenesulfanimide, cyclohexylamine, triethylamine, butylamine, saccharin, N,N-diethyl-p-toluidine, N,N-dimethyl-O-toluidine, acetylphenylhydrazine, maleic acid, and mixtures thereof.

[0050] The cure accelerator may be:

[0051] [ka]

[0052] wherein R is one or more of hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynyl; R 1 and R 2are each independently selected from halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl.

[0053] For example, the cure accelerator may be selected from one or more of the following:

[0054] [ka]

[0055] where R is as defined above.

[0056] The cure accelerator may be:

[0057] [ka] 1,2,3,4-Tetrahydrobenzo-h-quinolin-3-ol

[0058] The composition of the present invention may further comprise a radical polymerization initiator such as a peroxide.

[0059] The radical polymerization initiator is one or more selected from the group consisting of cumene hydroperoxide ("CHP"), para-menthane hydroperoxide, t-butyl hydroperoxide ("TBH"), t-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1,3-bis(t-butylperoxyisopropyl)benzene, diacetyl peroxide, butyl 4,4-bis(t-butylperoxy)valerate, p-chlorobenzoyl peroxide, t-butylcumyl peroxide, t-butyl perbenzoate, di-t-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di-t-butylperoxyhexane, 2,5-dimethyl-2,5-di-t-butyl-peroxyhex-3-yne, 4-methyl-2,2-di-t-butylperoxypentane, t-amyl hydroperoxide, 1,2,3,4-tetramethylbutyl hydroperoxide, and combinations thereof. Free-radical polymerization initiators may include encapsulated peroxides.

[0060] The compositions of the present invention may further comprise a cure accelerator in addition to or instead of the above. For example, the cure accelerator may comprise one or more metallocenes, such as ferrocene, suitably n-butylferrocene. Advantageously, the presence of the cure accelerator facilitates the curing of the compositions of the present invention on "inactive" or "passive" substrates, such as plastic substrates.

[0061] The composition of the present invention may further comprise at least one solvent.The use of a solvent may be beneficial, for example, for the purpose of blending or distribution.Suitably, the at least one solvent may be selected from the group comprising ethyl acetate, tetrahydrofuran, dichloromethane, chloroform, or a combination thereof.

[0062] However, when weight percentages are used, they are based on the total weight of the composition excluding solvent.

[0063] Desirably, the solid thermoplastic polyvinyl butyral resin may be soluble at room temperature or above in various solvents or combinations thereof that may be used during formulation or manufacturing processes, such as ethyl acetate. Advantageously, the use of a solid thermoplastic polyvinyl butyral resin with high solubility in, for example, ethyl acetate may avoid some of the practical problems commonly encountered, especially during large-scale manufacturing. For example, the use of a solid thermoplastic polyvinyl butyral resin with high solubility may eliminate the risk of gelation of the composition of the present invention during the manufacturing process or storage.

[0064] Suitably, the compositions of the present invention may be provided in any suitable solid form, such as a tape, filament, or coating applied to a substrate, including filaments or threads made from other materials, such as nylon or polyester threads. The thickness of the tape or filament of the solid composition may be less than 100 microns (μm). The tape or filament may be applied by wrapping, i.e., in a manner similar to current PTFE tape or thread sealing cords used to seal pipe joints. It is understood that the solid form may be formed into any desired pattern or layout, including sticks, tapes, filaments, gaskets, or patches. The composition in solid form, such as a tape or filament, may have sufficient integrity to be handled without breaking. The composition in solid form, such as a tape or filament, may be applied to a substrate, such as a metal bolt, at room temperature. The composition in solid form, such as a tape or filament, may be heat-resistant at temperatures of at least 150°C, e.g., at least 180°C, e.g., 200°C. This means that the composition is robust enough to maintain performance at temperatures typical of industrial environments. Even at elevated temperatures, compositions in solid form, such as tapes or filaments, are tack-free and dry to the touch, eliminating the need for a carrier such as a release liner. Tape or filament compositions may be wound onto themselves and, because they are tack-free and dry to the touch, will not adhere to themselves. Alternatively, tapes or filaments may comprise the anaerobic curable composition of the present invention and one or more release liners. For example, if the composition is stored at temperatures above 40°C, a release liner may be useful, as tack-free compositions may become sticky and adhere to themselves at temperatures above 40°C. As noted above, the compositions of the present invention may also be in any suitable solid form as a coating (solid and dry to the touch) applied to substrates, including tapes, filaments, or filaments or threads made from other materials, such as nylon or polyester threads.

[0065] 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 may be cured by exposure to an anaerobic environment. For example, the curable composition may be cured by exposure to an anaerobic environment for a period ranging from about 1 minute to about 30 minutes, e.g., from about 1 minute to about 20 minutes. Optionally, the curable composition may be cured within a temperature range of from about 40°C to about 100°C. For example, the curable composition may be cured by exposure to an anaerobic environment for a period ranging from about 1 minute to about 30 minutes within a temperature range of from about 40°C to about 100°C.

[0066] Once cured, the compositions of the present invention desirably exhibit breakaway torque values ​​of greater than 10 Nm against black oxidized mild steel or zinc phosphate substrates when evaluated on M10 nuts and bolts according to ISO 10964. Furthermore, the cured compositions of the present invention desirably exhibit breakaway torque values ​​of greater than 10 Nm at temperatures up to 180°C, e.g., 50°C, 80°C, 120°C, 150°C, or 180°C, when evaluated on zinc phosphate M10 nuts and bolts according to ISO 10964.

[0067] In another aspect, the present invention provides a threaded member including at least one threaded surface, wherein the at least one threaded surface comprises the anaerobic curable composition of the present invention. For example, the anaerobic curable composition may be in the form of a tape or filament. Alternatively, it may be in the form of a composition applied / coated on a thread made of another material. The tape, thread, or fiber can be applied to the threaded surface, for example, by at least partially wrapping the tape, thread, or fiber around the threaded surface. For example, the anaerobic curable composition can be coated onto a thread or fiber made of a different material to form a coated thread or fiber. The coated thread or fiber can be applied to the threaded surface, for example, by at least partially wrapping the coated thread or fiber around the threaded surface.

[0068] In yet another aspect, the present invention provides a method for manufacturing a threaded member comprising a thread-locking composition, the method comprising the steps of providing at least one threaded member having at least one threaded flank and applying the anaerobic curable composition of the present invention to the at least one threaded flank. Suitably, the anaerobic curable composition is applied to the at least one threaded flank as a coating applied to a substrate such as a tape, filament, or thread or fiber formed from a different material; for example, the tape, filament, or coated substrate may be at least partially wrapped around the at least one threaded flank of the threaded member. Suitably, the anaerobic curable composition in a tape, filament, or coated substrate is non-tacky and dry-feeling, eliminating the need for a carrier such as a release liner.

[0069] In yet another aspect, the present invention provides a method of assembling threaded members, comprising the steps of providing a first threaded member including at least one threaded surface; applying an anaerobic curable composition of the present invention to the at least one threaded surface; providing a second threaded member that matingly mates with the first threaded member; and matingly mating the first and second threaded members, thereby exposing the anaerobic curable composition to an anaerobic environment for a time sufficient to allow the anaerobic curable composition to harden between the first and second threaded members.

[0070] Also, (i) combining at least one solid thermoplastic polyvinyl butyral resin with a solvent; the at least one solid thermoplastic polyvinyl butyral resin optionally has 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, for example, about 40,000 g / mol to 120,000 g / mol, for example, 50,000 g / mol to 80,000 g / mol, the molecular weight Mw being determined according to ASTM D5296-05, and optionally 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; The solvent may be selected from ethyl acetate, tetrahydrofuran, dichloromethane, chloroform, or a combination thereof; (ii) mixing therein a liquid anaerobically curable component, a solid anaerobically curable component, and a curing component for curing the anaerobically curable component; and optionally, adding additives to the mixture to form an anaerobically curable composition; (iii) forming the mixture into the desired shape, for example by casting, or extruding, and / or applying it to a carrier such as a screw article or release liner; Also provided is a method for producing a threadlocking tape, thread, or fiber, comprising: removing the solvent and / or allowing the solvent to evaporate, thereby forming a tape, thread, or fiber comprising the anaerobic curable composition of the present invention and optionally a carrier: [Means for solving the problem]

[0071] As noted above, the present invention provides an anaerobic curable composition that includes 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.

[0072] Definitions and Standard Test Methods The term "liquid" means in the liquid state within a temperature range of about 5°C to 30°C, suitably at room temperature and atmospheric pressure.

[0073] The term "solid" refers to the solid state within the temperature range of about 5°C to 40°C, suitably at room temperature and atmospheric pressure. The solid state is defined as a state of matter in which the substance is not fluid, maintains its boundaries without a support, and the atoms or molecules occupy fixed positions relative to one another and are not free to move.

[0074] In the context of the present invention, "tack-free" means that the composition does not flake off during handling or use, despite feeling dry to the touch. For example, a molded article coated with the composition of the present invention feels dry to the touch. Articles coated with the composition of the present invention are considered to feel dry to the touch if 20 articles are individually placed on dry tissue paper for 4 hours and the appearance of the tissue remains unchanged.

[0075] Molecular weights disclosed herein are determined in accordance with ISO 13885-1:2008 "Binders for paints and varnishes -- Gel permeation chromatography (GPC) -- Part 1: Tetrahydrofuran (THF) as eluent."

[0076] The melting and resolidification temperature ranges were measured in accordance with ISO1137-1:2016 "Plastics - Differential scanning calorimetry (DSC) - Part 1 General principles."

[0077] Liquid anaerobic hardening component Suitably, the liquid anaerobic curable component comprises a liquid (meth)acrylate monomer component.

[0078] The liquid (meth)acrylate components are 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 triacrylate. The composition may comprise one or more (meth)acrylate monomers selected from acrylate, pentaerythritol tetraacrylate, phenoxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, cyclohexyl methacrylate, glycerol mono-methacrylate, glycerol 1,3-dimethacrylate, trimethylcyclohexyl methacrylate, methyl triglycol 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.

[0079] Preferred liquid (meth)acrylate monomers include 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, phenoxyethyl methacrylate, and methacrylic acid.

[0080] The one or more suitable (meth)acrylates may be selected from multifunctional (meth)acrylates, such as 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-(pentamethylene glycol) dimethacrylate, tetraethylene diglycol diacrylate, diglycerol Examples of suitable bisphenol A mono- and di(meth)acrylates include, but are not limited to, ethoxylated bisphenol A (meth)acrylate, 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.

[0081] For example, the redox curable component may include bisphenol A dimethacrylate:

[0082] [ka]

[0083] Suitably, the redox curable composition may include an ethoxylated bisphenol A di(meth)acrylate.

[0084] Still other (meth)acrylates that may be suitable for use herein are silicone (meth)acrylate moieties (“SiMA”), such as those taught and claimed by U.S. Pat. No. 5,605,999 (Chu), the disclosure of which is expressly incorporated herein by reference.

[0085] Other suitable materials may be selected from polyacrylate esters represented by the formula:

[0086] [ka]

[0087] In the formula, R 4 is a group selected from hydrogen, halogen, or alkyl having from 1 to about 4 carbon atoms; q is an integer at least equal to 1, preferably from 1 to about 4; and X is an organic group containing at least two carbon atoms and having a total binding capacity equal to q plus 1. Regarding the upper limit of the number of carbon atoms in X, essentially any value is workable for the monomer. However, as a practical matter, a typical upper limit is about 50 carbon atoms, preferably about 30, and more preferably about 20.

[0088] For example, X can be an organic group of the formula:

[0089] [ka]

[0090] In the formula, Y 1 and Y 2where each is an organic group, for example a hydrocarbon group containing at least 2 carbon atoms, desirably from 2 to about 10 carbon atoms, and z is an organic group, preferably a hydrocarbon group containing at least 1 carbon atom, preferably from 2 to about 10 carbon atoms. Other materials can be selected from reaction products of di- or tri-alkylolamines (e.g., ethanolamine or propanolamine) with acrylic acid, such as those disclosed in French Patent No. 1,581,361.

[0091] Suitable oligomers having (meth)acrylate functionality may also be used. Examples of such (meth)acrylate-functionalized oligomers include those having the following general formula:

[0092] [ka]

[0093] In the formula, R 5 is hydrogen, alkyl of 1 to about 4 carbon atoms, hydroxyalkyl of 1 to about 4 carbon atoms, or a group selected from the following:

[0094] [ka]

[0095] In the formula, R 4 is a group selected from hydrogen, halogen, or alkyl having 1 to about 4 carbon atoms; R 6 is hydrogen, hydroxyl, or a group selected from the following:

[0096] [ka]

[0097] m is an integer at least equal to 1, for example, 1 to about 15 or more, desirably 1 to about 8; n is an integer at least equal to 1, for example, 1 to about 40 or more, desirably about 2 to about 10; and p is 0 or 1.

[0098] Typical examples of acrylic ester oligomers corresponding to the above general formula include di-, tri-, and tetraethylene glycol dimethacrylate; di(pentamethylene glycol) dimethacrylate; tetraethylene glycol diacrylate; tetraethylene glycol di(chloroacrylate); diglycerol diacrylate; diglycerol tetramethacrylate; butylene glycol dimethacrylate; neopentyl glycol diacrylate; and trimethylolpropane triacrylate.

[0099] Di- and other polyacrylate esters, particularly the polyacrylate esters described in the previous paragraph, are preferred, although monofunctional acrylate esters (esters containing one acrylate group) may also be used.

[0100] Suitable compounds may be selected from cyclohexyl methacrylate, tetrahydrofurfuryl methacrylate, hydroxyethyl acrylate, hydroxypropyl methacrylate, t-butylaminoethyl methacrylate, cyanoethyl acrylate, and chloroethyl methacrylate.

[0101] Another useful class of materials are the reaction products of (meth)acrylate-functionalized hydroxyl- or amino-containing materials with polyisocyanates, used in appropriate proportions to convert all of the isocyanate groups to urethane or ureido groups, respectively.

[0102] The (meth)acrylate urethane or urea ester so formed may contain hydroxy or amino functional groups in the non-acrylate portion. Suitable (meth)acrylate esters for use may be selected from those of the following formula:

[0103] [ka]

[0104] wherein X is selected from --O-- and the following:

[0105] [ka] In the formula, R 9 is selected from hydrogen or lower alkyl having 1 to 7 carbon atoms; R 7 is selected from hydrogen, halogen (e.g., chlorine), or alkyl (e.g., methyl and ethyl groups); R 8 is a divalent organic group selected from alkylene, phenylene, and naphthylene having 1 to 8 carbon atoms.

[0106] These groups, when appropriately reacted with polyisocyanates, give monomers of the general formula:

[0107] [ka]

[0108] wherein n is an integer from 2 to about 6; B is a polyvalent organic radical selected from substituted and unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, alkaryl, and heterocyclic groups, and combinations thereof; R 7 , R 8 and X has the above meaning.

[0109] Depending on the nature of B, these (meth)acrylate esters with urea or urethane bonds may have molecular weights that fall into the oligomeric class (e.g., from about 1,000 g / mol to about 5,000 g / mol) or polymeric class (e.g., greater than about 5,000 g / mol).

[0110] Other unsaturated reactive monomers and oligomers can be used, such as styrene, maleimide, vinyl ether, allyl, allyl ether, and those described in US Pat. No. 6,844,080 B1. Vinyl resins such as those described in US Pat. No. 6,433,091 (Xia) can also be used. Methacrylate or acrylate monomers containing these unsaturated reactive groups can also be used.

[0111] Of course, combinations of these (meth)acrylates and other monomers may also be used.

[0112] Solid anaerobic hardening component The anaerobic curable composition of the present invention comprises a solid anaerobic curable component. The solid anaerobic 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 above.

[0113] Solid Thermoplastic Polyvinyl Butyral Resin The anaerobic curable composition of the present invention includes a solid thermoplastic polyvinyl butyral resin. The solid thermoplastic polyvinyl butyral resin may have a molecular weight Mw in the range of about 40,000 g / mol to about 250,000 g / mol, suitably about 40,000 g / mol to about 170,000 g / mol, for example, about 40,000 g / mol to 120,000 g / mol, for example, 50,000 g / mol to 80,000 g / mol, where the molecular weight Mw is determined according to ASTM D5296-05. The solid thermoplastic polyvinyl butyral resin may have a softening point 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 Butval® B-79 available from Eastman. Butvar® B-79 is a solid thermoplastic polyvinyl butyral resin having a molecular weight of 50,000 to 80,000 (size exclusion chromatography using low angle laser light scattering standards) and a softening point in the range of 140 to 200° C. Other suitable commercially available solid thermoplastic polyvinyl butyral resins include Butvar® B-72, Butvar® B-74, Butvar® B-76, Butvar® B-90, and Butvar® B-98, available from Eastman.

[0114] The anaerobic curable compositions shown in Table 1 were formulated into tapes.

[0115] [Table 1]

[0116] The compositions in Table 1 were prepared as follows. Solid thermoplastic polyvinyl butyral resin was dissolved in ethyl acetate at room temperature and then transferred to a Speedmixer® DAC150.147. The remaining ingredients were then added, and mixing continued until each component was dissolved. For compositions containing microencapsulated peroxide or methacrylate, the encapsulated components were not dissolved, so mixing continued until the microencapsulated components were dispersed throughout the solution. Each solution was then cast onto a silicone-treated polyester release liner (HiFi SR4-122, 75 microns thick) using an Elcometer® 4340 automatic film coater, with the coating plate temperature maintained at 30°C. After coating, the ethyl acetate was allowed to evaporate from the heated coating plate. A dry-feeling film was obtained.

[0117] The high-temperature thread-locking performance of the film formed from Example Composition 1 was evaluated on zinc phosphate nuts and bolts according to ISO 10964. The composition of the present invention was applied to an M10 bolt, and a screw assembly, torqued to 5 Nm, was formed with an M10 nut that could be matably mated with the M10 bolt. The screw assembly was held at 22°C for one week before the break strength and prevail strength of the cured composition were measured over the temperature ranges specified below. The results are shown in Table 2.

[0118] [Table 2]

[0119] The high temperature threadlocking performance of films formed from Example Compositions 2 and 3 was evaluated on zinc phosphate bolts and mild steel nuts according to ISO 10964. A composition of the present invention was applied to an M10 bolt, and a threaded assembly was formed with an M10 nut that could be matably mated with the M10 bolt and torqued to 5 Nm. The threaded assembly was held at 22°C for the specified time before measuring the break strength and prevail strength of the cured compositions at the temperature ranges specified below. The results are shown in Table 3.

[0120] [Table 3]

[0121] The threadlocking performance of each film formed from Example Compositions 1-4 was evaluated on M10 nuts and bolts of various substrates. Threaded assemblies were formed as described above and cured at 22°C for 24 hours before measuring the break strength and prevail strength of the cured compositions. The results for each composition are shown in Table 4.

[0122] [Table 4]

[0123] The threadlock performance of each film formed from Example Compositions 1 and 2 was measured after heat aging.

[0124] Screw assemblies were formed from films formed from Example Composition 1, torqued to 5 Nm, and attached to zinc phosphate nuts and bolts as described above. The screw assemblies were cured at 22°C for one week, and then aged at the specified temperatures for 1000 hours. The break strength and prevail strength of the cured compositions were then measured as described above. The results are shown in Table 5.

[0125] [Table 5]

[0126] Threaded assemblies of films formed from Example Composition 2 were torqued to 5 Nm and attached to zinc phosphate bolts and mild steel nuts as described above. The threaded assemblies were held at 22°C for 1 week to cure, and then aged at the specified temperatures for 2000 hours. The break strength and prevail strength of the cured compositions were then measured as described above. The results are shown in Table 6.

[0127] [Table 6]

[0128] The words "comprise" and "have / include" as used herein in relation to the present invention 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.

[0129] It will be appreciated that certain features of the invention, which are, for clarity, described in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features of the invention, which are, for brevity, described in the context of a single embodiment, may also be provided separately or in any suitable subcombination.

Claims

1. Liquid anaerobic curing component, solid anaerobic hardening component, a solid thermoplastic polyvinyl butyral resin, and a curing component for curing the anaerobic curing component; 1. An anaerobic curable composition comprising:

2. 2. The composition of claim 1, wherein the solid thermoplastic polyvinyl butyral resin has 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, for example 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. 3. The composition of claim 1 or 2, wherein the solid thermoplastic polyvinyl butyral resin has a softening point in the range of from about 50°C to about 300°C, suitably from about 100°C to about 250°C, preferably from about 140°C to about 200°C.

4. 4. The composition of any one of claims 1 to 3, wherein the liquid anaerobic curable component is present in an amount of from about 5 wt% to about 50 wt%, suitably from about 10 wt% to about 40 wt%, for example about 30 wt%, based on the total weight of the curable composition.

5. 5. The composition of any one of claims 1 to 4, wherein the solid anaerobic curable component is present in an amount of from about 6% to about 50% by weight based on the total weight of the composition, suitably from about 10% to about 25% by weight, for example about 13% by weight based on the total weight of the curable composition.

6. 6. The composition of any one of claims 1 to 5, wherein the solid thermoplastic polyvinyl butyral resin is present in an amount of from about 10% to about 50% by weight based on the total weight of the composition, suitably from about 15% to about 40% by weight, for example from about 15% to about 35% by weight, for example about 20% by weight based on the total weight of the curable composition.

7. 7. The composition of any one of claims 1 to 6, wherein the curing component for curing the anaerobic curable component is present in an amount of about 0.1 to about 10 wt%, for example about 1 to about 5 wt%, based on the total weight of the curable composition.

8. The composition of any one of claims 1 to 7, wherein the liquid anaerobically curable component comprises a liquid (meth)acrylate monomer component.

9. The liquid (meth)acrylate monomer component has 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; R ８ is selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, alkaryl, or aryl groups having 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted with silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbonate, amine, amide, sulfur, sulfonate, sulfone, etc.

9. The composition of claim 8, wherein the composition is one or more selected from the group consisting of:

10. The composition of any one of claims 1 to 9, wherein the solid anaerobic curable component comprises one or more solid (meth)acrylate monomer components.

11. 11. The composition of any one of claims 1 to 10, wherein the curing component comprises one or more selected from the group consisting of 1-acetyl-2-phenylhydrazine, N,N-dimethyl para-toluidine, N,N-diethyl para-toluidine, N,N-diethanol para-toluidine, N,N-dimethyl orthotoluidine, N,N-dimethyl meta-toluidine, indoline, 2-methylindoline, isoindoline, indole, 1,2,3,4-tetrahydroquinoline, 3-methyl-1,2,3,4-tetrahydroquinoline, 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. The composition of any one of claims 1 to 11, further comprising a radical polymerization initiator, such as a peroxide.

13. The radical polymerization initiator is selected from the group consisting of cumene hydroperoxide ("CHP"), para-menthane hydroperoxide, t-butyl hydroperoxide ("TBH"), t-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1,3-bis(t-butylperoxyisopropyl)benzene, diacetyl peroxide, butyl 4,4-bis(t-butylperoxy)valerate, p-chlorobenzoyl peroxide, t-butylcumyl peroxide, t- 13. The composition of claim 12, wherein the peroxysilane is one or more selected from the group consisting of butyl perbenzoate, di-t-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di-t-butylperoxyhexane, 2,5-dimethyl-2,5-di-t-butyl-peroxyhex-3-yne, 4-methyl-2,2-di-t-butylperoxypentane, t-amyl hydroperoxide, 1,2,3,4-tetramethylbutyl hydroperoxide, and combinations thereof.

14. 14. The composition of claim 12 or 13, wherein the free-radical polymerization initiator comprises an encapsulated peroxide.

15. The composition of any one of claims 1 to 14, further comprising a cure accelerator.

16. The cure accelerator may comprise one or more metallocenes, such as ferrocene, suitably n-butylferrocene; and / or a compound of the formula: 【Chemical 1】 (Wherein, X is CH ２ ,O,S,NR ４ , C.R. 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 and 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. The composition of claim 15, comprising a cure accelerator encompassed by

17. The composition of any one of claims 1 to 16 provided in the form of a tape, filament, or coated substrate.

18. The composition of any one of claims 1 to 16 provided as a coating on a yarn or fiber.

19. A tape comprising the anaerobic curable composition of any one of claims 1 to 18 and one or more release liners.

20. 19. A threaded member having at least one threaded surface, the at least one threaded surface comprising the anaerobic curable composition of any one of claims 1 to 18, optionally the anaerobic curable composition being in the form of a tape, filament, or coated substrate, and optionally the anaerobic curable composition in the form of a tape, filament, or coated substrate being applied to the threaded surface, for example, by wrapping the tape around at least a portion of the threaded surface.

21. a. providing at least one threaded member having at least one threaded surface; and b. applying to the at least one threaded surface the anaerobic curable composition of any one of claims 1 to 17; A method for producing a threaded member comprising the thread locking composition, comprising:

22. 22. The method of claim 21, wherein the anaerobic curable composition is in the form of a tape, filament, or coated substrate, and optionally the anaerobic curable composition in the form of a tape, filament, or coated substrate is wrapped around at least a portion of at least one threaded flank of the screw member.

23. (a) providing a first threaded member having at least one threaded surface; (b) applying the anaerobic curable composition of any one of claims 1 to 17 to the at least one threaded surface; (c) providing a second threaded member matingly mateable with the first threaded member; and matingly engaging the first and second threaded members and 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 members; A method for assembling a screw member, comprising:

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

25. (i) combining at least one solid thermoplastic polyvinyl butyral resin with a solvent; the at least one solid thermoplastic polyvinyl butyral resin optionally has 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, for example about 40,000 g / mol to 120,000 g / mol, for example 50,000 g / mol to 80,000 g / mol, the molecular weight Mw being determined according to ASTM D5296-05, and optionally a softening point of from 80°C to 30°C, for example from 100°C to 250°C, for example from 140°C to 200°C; The solvent is suitably selected from tetrahydrofuran, dichloromethane, chloroform, ethyl acetate, or combinations thereof; (ii) mixing therewith a liquid anaerobically curable component, a solid anaerobically curable component, and a curing component for curing the anaerobically curable component, and optionally adding additives to the mixture to form an anaerobically curable composition; (iii) forming the mixture into a desired shape, for example, by casting and / or spreading it onto a carrier such as a threaded article or a release liner; and removing the solvent and / or allowing the solvent to evaporate to form a tape, thread, or fiber comprising the anaerobic curable composition and optionally a carrier; 1. A method for producing a threadlocking tape, thread, or fiber, comprising:

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