CURABLE ELASTOMER COMPOSITIONS WITH LOW TEMPERATURE SEALING CAPABILITY

- Henkel Corporation

Curable sealant compositions having low temperature sealing ability improved over convention curable sealing compositions. The composition is flowable and can be cured to a cross linked form to provide cured reaction products that exhibit elastomeric properties. The curable elastomeric sealant composition can include a cross linkable elastomeric oligomer; an initiator or cross-linking agent; a glassy monomer and/or a rubbery monomer; and optionally one or more additives. Cured reaction products of the composition have a single Tg and retain a higher sealing force at low temperatures (but above the cured product Tg) as compared to a curable composition made from the same cross linkable elastomeric oligomer but without the glassy and/or rubbery monomer.

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Description
FIELD

The present disclosure relates generally to curable sealant compositions having low temperature sealing ability improved over convention curable sealing compositions.

BRIEF DESCRIPTION OF RELATED TECHNOLOGY

Sealants are used in a broad range of applications from automobiles to aircraft engines to contain or prevent solids, liquids, and/or gases from moving across a mating surface, boundary or interfacial region into or on a surrounding or adjacent area, region or surface. Sealants are available in many forms from low viscosity liquids to highly thixotropic pastes and depending on the application can vary in properties from a rigid glassy material to a rubbery elastic network. Elastomers are an important class of polymeric materials useful as sealing compositions and the focus of the current invention.

Sealants formulated with monomers, oligomers, polymers and/or other ingredients that react to form new covalent bonds that increase the molecular weight of the chemical backbone leading to entanglements and/or chemical cross-links that exhibits elastic properties are generally referred to as “curing” compositions. Sealants containing ingredients that do not react but exhibit elastic properties based on the thermodynamic properties of the polymer, entanglement of network chains or other molecular interactions are generally referred to as “non-curing” formulations.

Definitions used in the literature to describe rubbery and elastomer materials are very similar and sometimes used interchangeably. Elastomer is more general and typically refers to the elastic-bearing properties of a material. Rubber was originally referred to as an elastomer derived from naturally occurring polyisoprene and has expanded over the years to include both natural and synthetic based materials. IUPAC Compendium of Chemical Terminology, 2nd ed. (the “Gold Book”); compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997) defines an elastomer as a polymer that displays rubber-like elasticity. Elastomers are defined in the Physical Polymer Science Handbook by L. H. Sperling John Wiley & Sons, Inc., Publications, New York (2001) as an amorphous, cross-linked polymer above its glass transition temperature (Tg).

The equation of state for rubber elasticity describes the relationship between macroscopic sample deformation of a polymer (chain extension) and the retractive stress of the elastomer. The theory of rubber elasticity, derived from the second law of thermodynamics, states that the retractive stress of an elastomer arises as a result of the reduction in entropy upon extension and not changes in enthalpy. As a polymer chain is extended the number of conformations decrease (entropy decreases) and the retractive stress increases. Sperling writes that a long-chain molecule, capable of reasonably free rotation about its backbone, joined together in a continuous network is required for rubber elasticity.

σ = nRT r i 2 r o 2 ( α - 1 α 2 ) Equation of State for Rubber Elasticity

Where σ is the stress, n is the number of active network chains per unit volume, R is the ideal gas constant, T is temperature, a is the chain extension, and ri2/ro2 is the front factor that is approximately equal to one. The equation of state predicts that as the extension of an elastomer increases the observed stress increases. The stress is the retractive force created when for example an elastomer is placed under tension, biaxial tension or compression.

The theory of rubber elasticity can be observed in practice when a cured seal operating at a temperature above its glass transition temperature is compressed and exhibits sealing forces that can be measured using instruments know in the art. The glass transition temperature of the elastomer in the cured seal defines an important boundary condition where free rotation of the main chain is restricted as the elastomer transitions from the rubbery to the glassy region resulting in a loss of molecular free rotation, molecular chain extension and the resulting retractive stress. As the temperature of the elastomer approaches the glass transition temperature, the resulting elastic retractive force approaches zero.

The utility of an elastomeric sealant is measured by the ability of the cured sealant composition to provide a positive sealing force when exposed to operating conditions over the lifetime of the product. Temperature is an important factor that affects the performance of a sealant and can have a significant impact on the operating lifetime. The temperature range in harsh ambient conditions can vary from +150° C. to −65° C. In less severe applications temperatures can vary from +100° C. to −40° C.

It was observed that some cured elastomeric sealants at temperatures well above the glass transition temperature of the overall polymer network have a sealing force that decreases to nearly zero. In one case a cured, elastomeric sealant with a −61° C. Tg, measured by DSC, had a very low sealing force at −40° C. that would be unacceptable for most sealing applications.

It is known from statistical thermodynamics of rubber elasticity that the force generated during the deformation of an elastomer is directly proportional to the end-to-end distance of the cross-linked network and the temperature of the matrix. When an elastomer is deformed the retractive force should remain positive, in the rubbery region, as long as the temperature is above the Tg. There is nothing in the above equation of state of rubbery elasticity that would predict that changing the glassy or hard segment in an elastomer having a single Tg, and which exhibits no other first or second order thermodynamic transitions, could increase the low temperature sealing force within the rubbery region.

SUMMARY

One aspect of the disclosure provides a curable elastomeric sealant composition. The composition is flowable and can be cured to a cross linked form to provide cured reaction products that exhibit elastomeric properties. The curable elastomeric sealant composition can include a cross linkable elastomeric oligomer; an initiator or cross-linking agent; a glassy monomer and/or a rubbery monomer; and optionally one or more of a catalyst; a filler; an antioxidant; and an optional reaction modifier. The cross linkable elastomeric sealant composition can be prepared by reacting a cross linkable elastomeric oligomer having a Tg with at least one of a glassy monomer and a rubbery monomer. Cured reaction products of the composition have a single Tg and retain a higher sealing force at low temperatures (but above the cured product Tg) as compared to a curable composition made from the same cross linkable elastomeric oligomer but without the glassy and/or rubbery monomer.

In one embodiment the cross linkable elastomeric oligomer is a telechelic polyisobutylene (PIB) based material terminated at each end with acrylate moieties.

Another aspect provides a component having a first predetermined sealing surface aligned with a second predetermined sealing surface. A cured reaction product of a polyisobutylene (PIB) based composition is disposed between the sealing surfaces to prevent movement of materials such as liquids, gasses or fuels between the aligned sealing surfaces. The composition may be cured in contact with one, both or none of the sealing surfaces. Advantageously, the seal formed by the cured reaction product provides low temperature sealing (about −40° C.) within the rubbery region along with excellent resistance to moisture, water, glycols, acids, bases and polar compounds.

The disclosed compounds include any and all isomers and stereoisomers. In general, unless otherwise explicitly stated the disclosed materials and processes may be alternately formulated to comprise, consist of, or consist essentially of, any appropriate components, moieties or steps herein disclosed. The disclosed materials and processes may additionally, or alternatively, be formulated so as to be devoid, or substantially free, of any components, materials, ingredients, adjuvants, moieties, species and steps used in the prior art compositions or that are otherwise not necessary to the achievement of the function and/or objective of the present disclosure.

When the word “about” is used herein it is meant that the amount or condition it modifies can vary some beyond the stated amount so long as the function and/or objective of the disclosure are realized. The skilled artisan understands that there is seldom time to fully explore the extent of any area and expects that the disclosed result might extend, at least somewhat, beyond one or more of the disclosed limits. Later, having the benefit of this disclosure and understanding the concept and embodiments disclosed herein, a person of ordinary skill can, without inventive effort, explore beyond the disclosed limits and, when embodiments are found to be without any unexpected characteristics, those embodiments are within the meaning of the term about as used herein.

BRIEF DESCRIPTION OF THE DRAWINGS

Referring now to the drawings wherein like elements are numbered alike in the several Figures:

FIG. 1 is a relaxation recovery sequence for the cured material of example 3. The lower plot is temperature at the time shown and the upper plot is sealing force of that cured material at the time shown.

FIG. 2 is a scan from the Differential Scanning calorimeter analysis of the cured products of composition of Example 1.

FIG. 3 is a scan from the Differential Scanning calorimeter analysis of the cured products of composition of Example 2.

FIG. 4 is a scan from the Differential Scanning calorimeter analysis of the cured products of composition of Example 3.

FIG. 5 is a scan from the Differential Scanning calorimeter analysis of the cured products of composition of Example 24.

FIG. 6 is a scan from the Differential Scanning calorimeter analysis of the cured products of composition of Example 30.

FIG. 7 is a scan from the Differential Scanning calorimeter analysis of the cured products of composition of Example 34.

FIG. 8 is a graph showing sealing force at −40° C. for compositions of Examples 1, 2 and 3 having varying oligomer:monomer ratio.

 DETAILED DESCRIPTION

A curable elastomeric sealant composition is a composition that is flowable and can be cured to a cross linked form to provide cured reaction products of the composition that exhibit elastomeric properties. The curable elastomeric sealant composition can include a cross linkable elastomeric oligomer; an initiator or cross-linking agent; a glassy monomer and/or a rubbery monomer; and optionally one or more of a catalyst; a filler; an antioxidant; and an optional reaction modifier. The cross linkable elastomeric sealant composition can be prepared by reacting a cross linkable elastomeric oligomer having a Tg with at least one of a glassy monomer and a rubbery monomer. The cross linkable elastomeric sealant composition can be cured by exposure to conditions and for a time sufficient to at least partially cross-link and cure that composition. Suitable cure conditions, depending on formulation of the cross linkable elastomeric sealant composition include exposure to heat and radiation such as actinic radiation.

Cured reaction products of the composition have a single Tg as measured by Differential Scanning calorimetry (DSC) and retain a higher sealing force at low temperatures (but above the cured product Tg) as compared to a curable composition made from the same cross linkable elastomeric oligomer but without the glassy and/or rubbery monomer.

Cross Linkable Elastomeric Oligomer

A number of sealant chemistries are believed to be suitable for use in the sealant composition. These chemistries include fluoroelastomer; EPDM and other hydrocarbons; styrenic block elastomer; C4 and C5 monomers such as isoprene and isobutylene; acrylates and methacrylates; acrylic emulsion; ethylene acrylate elastomer; functionalized polyacrylate; silylated acrylate; silicone; silylated polyether; silylated polyester; silylated polyamide; polyurethane; silylated polyurethane; plastisol and polyvinyl chloride; polysulfide and polythioether; flexible epoxy; vinyl acetate-ethylene latex; unsaturated polyester; polyolefins, amides and acetates for example EVA. Non-curable chemistries such as oleoresinous based (for example linseed oil) sealants and bituminous sealants may also be useful.

The curable elastomeric sealant composition advantageously includes a cross linkable elastomeric oligomer. In one desirable embodiment the cross linkable elastomeric oligomer is a telechelic, polyisobutylene polymer with acrylate moieties at each end (polyisobutylene diacrylate or PIB diacrylate).

Glassy Monomer

The curable elastomeric sealant composition can include a glassy monomer that is reacted with the cross linkable elastomeric oligomer. A glassy monomer has a glass transition temperature above the glass transition temperature of the cross linkable elastomeric oligomer. Typically the glassy monomer has a glass transition temperature above 20° C.

Some examples of glassy monomers include stearyl acrylate (Tg 35° C.); trimethylcyclohexyl methacrylate (Tg 145° C.); isobornyl methacrylate (Tg 110° C.); isobornyl acrylate (Tg 88° C.); and the FANCRYL methacryl esters marketed by Hitachi Chemical Corporation such as dicyclopentanylmethacrylate (FA-513M Tg 175° C.) and dicyclopentanyl Acrylate (FA-513AS, Tg 140° C.). Other examples of glassy and rubbery monomers are listed in the Tables at the end of the specification.

Rubbery Monomer

The curable elastomeric sealant composition can include a rubbery monomer that is reacted with the cross linkable elastomeric oligomer. A rubbery monomer has a glass transition temperature below the glass transition temperature of the glassy monomer. Typically the rubbery monomer has a glass transition temperature below 20° C. Some examples of rubbery monomers include isooctyl acrylate (Tg −54° C.); isodecyl acrylate (Tg −60° C.); isodecyl methacrylate (Tg −41° C.); n-lauryl methacrylate (Tg −65); and 1,12-dodecanediol dimethacrylate (Tg −37° C.). Other examples of glassy and rubbery monomers are listed in the Tables at the end of the specification.

Initiator or Cross-Linking Agent

The curable elastomeric sealant composition can include an initiator or cross-linking agent to at least partially cross-link and cure that composition.

The initiator or cross-linking agent can be a heat-cure initiator or initiator system comprising an ingredient or a combination of ingredients which at the desired elevated temperature conditions produce free radicals. Suitable initiators may include peroxy materials, e.g., peroxides, hydroperoxides, and peresters, which under appropriate elevated temperature conditions decompose to form peroxy free radicals which are initiatingly effective for the polymerization of the curable elastomeric sealant compositions. The peroxy materials may be employed in concentrations effective to initiate curing of the curable elastomeric sealant composition at a desired temperature and typically in concentrations of about 0.1% to about 10% by weight of composition.

Another useful class of heat-curing initiators comprises azonitrile compounds which yield free radicals when decomposed by heat. Heat is applied to the curable composition and the resulting free radicals initiate polymerization of the curable composition. Compounds of the above formula are more fully described in U.S. Pat. No. 4,416,921, the disclosure of which is incorporated herein by reference.

Azonitrile initiators of the above-described formula are readily commercially available, e.g., the initiators which are commercially available under the trademark VAZO from E.I. DuPont de Nemours and Company, Inc., Wilmington, Del.

The initiator or cross-linking agent can be a photoinitiator. Photoinitiators enhance the rapidity of the curing process when the photocurable elastomeric sealant composition is exposed to electromagnetic radiation, such as actinic radiation, for example ultraviolet (UV) radiation. Examples of some useful photoinitiators include, but are not limited to, photoinitiators available commercially from Ciba Specialty Chemicals, under the “IRGACURE” and “DAROCUR” trade names, specifically “IRGACURE” 184 (1-hydroxycyclohexyl phenyl ketone), 907 (2-methyl-1-[4-(methylthio)phenyl]-2-morpholino propan-1-one), 369 (2-benzyl-2-N,N-dimethylamino-1-(4-morpholinophenyl)-1-butanone), 500 (the combination of 1-hydroxy cyclohexyl phenyl ketone and benzophenone), 651 (2,2-dimethoxy-2-phenyl acetophenone), 1700 (the combination of bis(2,6-dimethoxybenzoyl-2,4,4-trimethyl pentyl)phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one), and 819 [bis(2,4,6-trimethyl benzoyl)phenyl phosphine oxide] and “DAROCUR” 1173 (2-hydroxy-2-methyl-1-phenyl-1-propan-1-one) and 4265 (the combination of 2,4,6-trimethylbenzoyldiphenyl-phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one); and the visible light [blue] photoinitiators, dl-camphorquinone and “IRGACURE” 784DC. Of course, combinations of these materials may also be employed herein.

Other photoinitiators useful herein include alkyl pyruvates, such as methyl, ethyl, propyl, and butyl pyruvates, and aryl pyruvates, such as phenyl, benzyl, and appropriately substituted derivatives thereof. Photoinitiators particularly well-suited for use herein include ultraviolet photoinitiators, such as 2,2-dimethoxy-2-phenyl acetophenone (e.g., “IRGACURE” 651), and 2-hydroxy-2-methyl-1-phenyl-1-propane (e.g., “DAROCUR” 1173), bis(2,4,6-trimethyl benzoyl)phenyl phosphine oxide (e.g., “IRGACURE” 819), and the ultraviolet/visible photoinitiator combination of bis(2,6-dimethoxybenzoyl-2,4,4-trimethylpentyl)phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one (e.g., “IRGACURE” 1700), as well as the visible photoinitiator bis(η5-2,4-cyclopentadien-1-yl)-bis[2,6-difluoro-3-(1H-pyrrol-1-yl)phenyl]titanium (e.g., “IRGACURE” 784DC). Useful actinic radiation includes ultraviolet light, visible light, and combinations thereof.

Desirably, the actinic radiation used to cure the photocurable elastomeric sealant composition has a wavelength from about 200 nm to about 1,000 nm. Useful UV includes, but is not limited to, UVA (about 320 nm to about 410 nm), UVB (about 290 nm to about 320 nm), UVC (about 220 nm to about 290 nm) and combinations thereof. Useful visible light includes, but is not limited to, blue light, green light, and combinations thereof. Such useful visible lights have a wavelength from about 450 nm to about 550 nm. Photoinitiators can be employed in concentrations effective to initiate curing of the curable elastomeric sealant composition at a desired exposure to actinic radiation and typically in concentrations of about 0.01% to about 10% by weight of composition.

Catalyst

The curable elastomeric sealant composition can include a catalyst to modify speed of the initiated reaction.

Filler

The curable elastomeric sealant composition can optionally include a filler. Some useful fillers include, for example, lithopone, zirconium silicate, hydroxides, such as hydroxides of calcium, aluminum, magnesium, iron and the like, diatomaceous earth, carbonates, such as sodium, potassium, calcium, and magnesium carbonates, oxides, such as zinc, magnesium, chromic, cerium, zirconium and aluminum oxides, calcium clay, fumed silicas, silicas that have been surface treated with a silane or silazane such as the AEROSIL products available from Evonik Industries, silicas that have been surface treated with an acrylate or methacrylate such as AEROSIL R7200 or R711 available from Evonik Industries, precipitated silicas, untreated silicas, graphite, synthetic fibers and mixtures thereof. When used filler can be employed in concentrations effective to provide desired physical properties in the uncured composition and cured reaction products and typically in concentrations of about 0.1% to about 70% by weight of composition.

Antioxidant

The curable elastomeric sealant composition can optionally include an anti-oxidant. Some useful antioxidants include those available commercially from Ciba Specialty Chemicals under the tradename IRGANOX. When used, the antioxidant should be used in the range of about 0.1 to about 15 weight percent of curable composition, such as about 0.3 to about 1 weight percent of curable composition.

Reaction Modifier

The curable elastomeric sealant composition can include a reaction modifier. A reaction modifier is a material that will increase or decrease reaction rate of the curable elastomeric sealant composition. For example, quinones, such as hydroquinone, monomethyl ether hydroquinone (MEHQ), napthoquinone and anthraquinone, may also be included to scavenge free radicals in the curable elastomeric sealant composition and thereby slow reaction of that composition and extend shelf life. When used, the reaction modifier can be used in the range of about 0.1 to about 15 weight percent of curable composition.

Adhesion Promoter

The curable elastomeric sealant composition can include one or more adhesion promoters that are compatible and known in the art. Examples of useful commercially available adhesion promoters include octyl trimethoxysilane (commercially available from Chemtura under the trade designation A-137), glycidyl trimethoxysilane (commercially available from Chemtura under the trade designation A-187), methacryloxypropyl trimethoxysilane (commercially available from Chemtura under the trade designation of A-174), vinyl trimethoxysilane, tetraethoxysilane and its partial condensation products, and combinations thereof. When used, the adhesion promoter can be used in the range of about 0.1 to about 15 weight percent of curable composition.

Rheology Modifiers

The curable elastomeric sealant composition can optionally include a thixotropic agent to modify rheological properties of the uncured composition. Some useful thixotropic agents include, for example, silicas, such as fused or fumed silicas, that may be untreated or treated so as to alter the chemical nature of their surface. Virtually any reinforcing fused, precipitated silica, fumed silica or surface treated silica may be used.

Examples of treated fumed silicas include polydimethylsiloxane-treated silicas, hexamethyldisilazane-treated silicas and other silazane or silane treated silicas. Such treated silicas are commercially available, such as from Cabot Corporation under the tradename CAB-O-SIL ND-TS and Evonik Industries under the tradename AEROSIL, such as AEROSIL R805. Also useful are the silicas that have been surface treated with an acrylate or methacrylate such as AEROSIL R7200 or R711 available from Evonik Industries.

Examples of untreated silicas include commercially available amorphous silicas such as AEROSIL 300, AEROSIL 200 and AEROSIL 130. Commercially available hydrous silicas include NIPSIL E150 and NIPSIL E200A manufactured by Japan Silica Kogya Inc.

When used rheology modifier can be employed in concentrations effective to provide desired physical properties in the uncured composition and cured reaction products and typically in concentrations of about 0.1% to about 70% by weight of composition.

Coloring Agent.

The curable elastomeric composition can be clear to translucent. For some applications a colored composition can be beneficial to allow for inspection of the applied composition. A coloring agent, for example a pigment or dye, can be used to provide a desired color beneficial to the intended application. Exemplary coloring agents include titanium dioxide, C.I. Pigment Blue 28, C.I. Pigment Yellow 53 and phthalocyanine blue BN. In some applications a fluorescent dye can be added to allow inspection of the applied composition under UV radiation. The coloring agent will be present in amounts sufficient to allow for detection. If present, the coloring agent is desirably incorporated in amounts of about 0.002% or more by weight. The maximum amount is governed by considerations of cost and absorption of radiation that interferes with cure of the composition. More desirably, the dye is present in amounts of about 0.002% to about 1.0% weight by weight of the total composition.

The curable elastomeric sealant composition can optionally include other additives at concentrations effective to provide desired properties so long as they do not inhibit the desirable properties such as curing mechanism, elongation, low temperature sealing force, tensile strength, chemical resistance. Example of such optional additives include, for example, reinforcing materials such as fibers, diluents, reactive diluents, coloring agents and pigments, moisture scavengers such as methyltrimethoxysilane and vinyltrimethyloxysilane, inhibitors and the like may be included.

Exemplary Composition Ranges:

A curable elastomeric sealant composition can typically comprise:

about 50 to 99 wt % of a cross linkable elastomeric oligomer;
about 1 to 30 wt % of a glassy monomer;
about 0 to 30 wt % of a rubbery monomer;
about 0.01 to 10 wt % of an initiator or cross-linking agent;
about 0 to 5 wt % of a catalyst;
about 0 to 70 wt % of a filler;
about 0 to 15 wt % of a antioxidant;
about 0 to 15 wt % of a reaction modifier;
about 0 to 15 wt % of adhesion promoter;
about 0 to 70 wt % of rheology modifier;
about 0 to 1.0 wt % of coloring agent.

The glassy monomer(s) and the rubbery monomer(s) can be chosen so that a desired average glass transition temperature for that combination of monomers is obtained. The average glass transition temperature for a combination of monomers is defined by the Fox equation (1/Tgcomb=M1/Tg1+M2/Tg2 see T. G. Fox, Bull. Am. Phys. Soc., 1, 123 (1956), the contents of which are incorporated by reference herein.

The ratio of cross linkable elastomeric oligomer to glassy monomer must be chosen to provide sufficient glassy monomer to increase low temperature sealing force of the cured sealant reaction products. However, the ratio must not add so much glassy monomer that the elastomeric properties of the cured sealant reaction products are undesirably affected. Thus, there is a need to balance the ratio of cross linkable elastomeric oligomer to glassy monomer depending on desired properties: too little glassy material and the cured sealant composition will not have a desirable low temperature sealing force but too much glassy material and sealing ability of the cured sealant at higher temperatures is lost.

The ratio of cross linkable elastomeric oligomer to glassy monomer will depend on the oligomer and monomer used; the final application for the sealant; and the cured sealant properties desired for that application. A ratio of cross linkable elastomeric oligomer to glassy monomer in the range of 75:25 to 95:5 respectively provides a general starting point. At present there is no way to predict cured sealant properties for a cross linkable sealant composition formulation. Testing of formulations for low temperature sealing force and higher temperature sealing properties is required to arrive at a formulation and ratio providing desired properties.

Specific physical properties required for the uncured, sealant composition will depend on application. For example, sealant composition viscosity can be formulated for application method and desired cycle time. Viscosity of the uncured sealant composition can be 10,000 Cps to 1,000,000 Cps at 25° C.

Specific physical properties required for cured reaction products of the sealant composition will depend on sealing application, minimum and maximum operating temperatures within the application, desired tensile strength at high temperatures and desired sealing force at low temperatures. Some useful physical properties for the cured reaction products include: Hardness, Shore A about 20 to about 90 and desirably about 40 to about 60. Tensile strength, about 100 psi to about 2,000 psi and desirably about 500 psi to about 1,000 psi. Elongation, about 10% to about 1,000% and desirably about 100% to about 500%. Low temperature (−40° C.) sealing force, about 0 Newtons to about 50 Newtons and desirably about 6 Newtons to about 30 Newtons. Desirably the cured reaction product has a compression set value that allows a seal made therefrom to maintain a predetermined minimum sealing force throughout the design life of the seal.

Components to be sealed by the disclosed curable compositions have a first predetermined sealing surface that is aligned with a second predetermined sealing surface. Typically, the aligned sealing surfaces are in a fixed relationship and move very little relative to each other. The aligned sealing surfaces are generally in fluid communication with a chamber. The seal formed between the aligned sealing surfaces prevents movement of materials between the surfaces and into, or out of, the chamber.

One or both of the sealing surfaces can be machined or formed. The predetermined sealing surfaces are designed to allow a curable composition to be disposed on one or both surfaces during initial assembly of the component to form a seal therebetween. Design of the predetermined sealing surfaces enhances parameters such as alignment of the surfaces, contact area of the surfaces, surface finish of the surfaces, “fit” of the surfaces and separation of the surfaces to achieve a predetermined sealing effect. A predetermined sealing surface does not encompass surfaces that were not identified or designed prior to initial assembly to accommodate a seal or gasket, for example the outside surface of a component over which a repair material is molded or applied to lessen leaking. Sealing surfaces on an engine block and oil pan or engine intake manifold are examples of sealing surfaces in fixed relationship.

The disclosed curable compositions can be in a flowable state for disposition onto at least a portion of one sealing surface to form a seal between the surfaces when they are aligned. The curable composition can be applied as a film over the sealing surface. The curable composition can also be applied as a bead in precise patterns by tracing, screen printing, robotic application and the like. In bead applications the disclosed compositions are typically dispensed as a liquid or semi-solid under pressure through a nozzle and onto the component sealing surface. The nozzle size is chosen to provide a line or bead of composition having a desired width, height, shape and volume. The curable composition can be contained in a small tube and dispensed by squeezing the tube; contained in a cartridge and dispensed by longitudinal movement of a cartridge sealing member; or contained in a larger container such as a 5 gallon pail or 55 gallon drum and dispensed at the point of use by conventional automated dispensing equipment. Container size can be chosen to suit the end use application.

The curable composition can be used to form a formed in place gasket (FIPG). In this application the composition is dispensed onto a first predetermined sealing surface. The first predetermined sealing surface and dispensed composition is aligned and sealingly engaged with a second predetermined sealing surface before the composition has fully cured. The composition will adhere to both sealing surfaces as it cures.

The curable composition can be used to form a cured in place gasket (CIPG). In this application the composition is dispensed onto a first predetermined sealing surface and allowed to substantially cure before contact with a second predetermined sealing surface. The first sealing surface and cured composition is sealingly engaged with the second sealing surface thereby compressing the cured composition to provide a seal between the sealing surfaces. The composition will adhere to only the first sealing surface.

The curable composition can be used to form a mold in place gasket (MIPG). In this application the part comprising the first predetermined sealing surface is placed in a mold. The composition is dispensed into the mold where it contacts the first sealing surface. The composition is typically allowed to cure before removal from the mold. After molding, the first sealing surface and molded composition is sealingly engaged with a second predetermined sealing surface thereby compressing the cured composition to provide a seal between the sealing surfaces. The composition will adhere to only the first sealing surface.

The curable composition can be used in liquid injection molding (LIM). In this application uncured composition is dispensed into a mold without any predetermined sealing surface under controlled pressure and temperature. The composition is typically allowed to cure before removal from the mold. After removal the molded part will retain its shape. In sealing applications the molded gasket is disposed between two predetermined sealing surfaces and compressed to provide a seal between the sealing surfaces.

The following examples are included for purposes of illustration so that the disclosure may be more readily understood and are in no way intended to limit the scope of the disclosure unless otherwise specifically indicated.

Unless otherwise specified the following test procedures were used on cured specimens in the Examples.

Shore A hardness ASTM D2240-05 Tensile strength ASTM D412-98A modulus ASTM D412-98A elongation ASTM D412-98A

Compression

set “A” ASTM D395. Samples were allowed to cool to room temperature in the uncompressed stated before testing.

Compression

set “B” ASTM D395 modified. Samples were allowed to cool to room temperature in a compressed state before testing.
glass transition Tg Differential Scanning calorimetry (DSC).

Curable, elastomeric gasketing compositions were made. Polyisobutylene diacrylate (PIB diacrylate) is a telechelic, polyisobutylene polymer with acrylate moieties at each end, with a molecular weight of about 1,000 to about 1,000,000 and a very low glass transition temperature (Tg) of −67° C. PIB diacrylate was chosen as the rubber matrix of the elastomeric gasketing compositions. PIB diacrylate can be prepared using a number of known reactions schemes, some of which are listed below and the contents of which are incorporated by reference herein in their entirety. The method of scheme 2 can be used to prepare the PIB diacrylate used in the following compositions.

Various acrylates and methacrylates having a Tg greater than 20° C. were selected as the glassy monomer. Various acrylates and methacrylates having a Tg less than 0° C. were selected as the rubbery monomer and as a reactive diluent. The ratio of rubber phase over glass phase was adjusted by trial and error to provide the desired elasticity and sealing force at lower temperature.

Preparation of Curable Gasketing Compositions:

1) Premix preparation: Charge all liquids including initiator, antioxidant, reaction modifier. Mix until no solids remain.
2) Charge elastomeric oligomer into premix. Mix until uniform.
3) Add fillers and mix until uniform.
4) Apply vacuum to degas sample. Discharge bubble free material into storage container.

Examples - curable gasketing composition 1 2 3 4 5 mass mass mass mass mass Component (gm) (gm) (gm) (gm) (gm) PIB diacry- 59.1 66.9 71.1 75.3 79.5 late FA-513M1 19.7 16.7 12.6 8.4 4.2 Irgacure 2.1 0.8 0.8 0.8 0.8 8192 Irganox 0.8 0.8 0.8 0.8 0.8 10103 Aerosil 3.8 4.1 4.1 4.1 4.1 R1064 H30RY5 4.0 4.2 4.2 4.2 4.2 diluent6 4.7 5.0 5.0 5.0 5.0 viscosity 180000 289000 456000 664500 995000 (cps, 25° C., 12/s) 1Dicyclopentanylmethacrylate glassy monomer marketed by Hitachi Chemical Corporation. 2available from Ciba. 3available from Ciba. 4Available from Evonik. 5Available from Wacker. 62 CsT polyalphaolefin diluent.

Typical properties for thermally cured reaction products of Examples 1 2 3 4 5 Shore A hardness (point) 64 55 45 42 32 Tensile strength (psi) 1084 727 543 398 296 Elongation (%) 225 195 174 156 148 100% modulus (psi) 460 323 264 215 156 Compression set A (%, 25%) 9 5 6 7 4 Compression set B (%, 25%) 62 41 27 17 11

Compression set B values of greater than 0 but less than 40 indicate a cured material may have an advantageous low temperature sealing force. The high compression set B value (62) of Example 1 indicates a cured material that will not maintain desirable sealing force at low temperatures.

Example (mass, gm) Tg 6 7 8 9 10 11 12 PIB diacrylate −67 62.7 59.1 63.8 64.8 65.9 62.7 62.7 FA-513M 175 19.7 FA-513AS1 140 20.9 isobornyl acrylate 88 19.9 18.8 17.8 16 16 isobornyl methacrylate 110 trimethylcyclohexyl methacrylate 145 stearyl acrylate 35 isooctyl acrylate −54 Isodecyl acrylate −60 2.6 2.6 2.6 5.0 Isodecyl methacrylate −41 n-lauryl methacrylate −65 1,12-dodecanediol −37 dimethacrylate Irgacure 819 0.8 2.1 0.8 0.8 0.8 0.8 0.8 Irganox 1010 0.8 0.8 0.8 0.8 0.8 0.8 0.8 Aerosil R106 4.1 3.8 4.1 4.1 4.1 4.1 2.5 H30Ry 4.2 3.9 4.2 4.2 4.2 4.2 4.2 2 cSt polyalphaolefin diluent 4.7 9 cSt polyalphaolefin diluent uncured viscosity (cps, 25° C., 340,000 180000 252000 284000 299000 548000 181000 12/s) Shore A hardness 51 64 44 40 41 40 tensile strength (psi) 623 912 501 469 426 436 elongation (%) 192 226 218 215 202 212 100% modulus (psi) 326 388 197 187 187 166 compression set A (% 25%) 14 25 11 12 11 13 compression set B (% 25%) 46 72 31 32 30 25 Example (mass, gm) Tg 13 14 15 16 17 18 19 PIB diacrylate −67 62.7 62.7 62.7 62.7 62.7 62.7 62.7 FA-513M 175 10.5 10.5 FA-513AS 140 isobornyl acrylate 88 15.7 15.7 15.7 isobornyl methacrylate 110 trimethylcyclohexyl methacrylate 145 10.5 stearyl acrylate 35 11.5 isooctyl acrylate −54 5.2 10.5 5.2 10.5 Isodecyl acrylate −60 4.2 10.5 Isodecyl methacrylate −41 n-lauryl methacrylate −65 1,12-dodecanediol −37 1.0 0.5 dimethacrylate Irgacure 819 .8 0.4 0.8 0.8 0.8 0.8 0.8 Irganox 1010 .8 0.5 0.8 0.8 0.8 0.8 0.8 Aerosil R106 4.1 4.1 3.5 4.1 4.1 3.0 4.1 H30Ry 4.2 4.2 4.2 4.2 4.2 4.2 4.2 2 cSt polyalphaolefin diluent 9 cSt polyalphaolefin diluent uncured viscosity (cps, 25° C., 235000 175000 204000 194000 130000 177000 170000 12/s) Shore A hardness 48 36 45 44 41 45 48 tensile strength (psi) 451 168 484 437 421 534 534 elongation (%) 158 110 222 208 213 212 231 100% modulus (psi) 251 150 183 187 172 196 198 compression set A (% 25%) 15 14 8 14 13 11 23 compression set B (% 25%) 34 20 29 33 30 26 40 Example (mass, gm) Tg 20 21 22 23 24 25 26 PIB diacrylate −67 62.7 62.7 62.7 62.7 62.7 62.7 62.7 FA-513M 175 FA-513AS 140 6.2 6.2 isobornyl acrylate 88 15.7 12.6 12.6 6.2 15.7 7.8 15.7 isobornyl methacrylate 110 trimethylcyclohexyl methacrylate 145 stearyl acrylate 35 isooctyl acrylate −54 5.2 8.4 5.2 5.2 5.2 Isodecyl acrylate −60 6.4 8.4 Isodecyl methacrylate −41 n-lauryl methacrylate −65 1,12-dodecanediol dimethacrylate −37 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Irgacure 819 0.8 0.8 0.8 0.8 0.8 0.8 0.8 Irganox 1010 0.8 0.8 0.8 0.8 0.8 0.8 0.8 Aerosil R106 3.0 3.0 3.0 3.0 3.0 3.0 3.0 H30Ry 4.2 4.2 4.2 4.2 4.2 4.2 4.2 2 cSt polyalphaolefin diluent 9 cSt polyalphaolefin diluent uncured viscosity (cps, 25° C., 164000 166000 148000 162000 177000 210000 182000 12/s) Shore A hardness 43 44 40 42 45 46 47 tensile strength (psi) 435 336 409 423 572 515 515 elongation (%) 188 167 191 186 197 197 187 100% modulus (psi) 192 181 180 189 222 212 219 compression set A (% 25%) 7 5 6 7 7 7 6 compression set B (% 25%) 26 21 20 18 23 24 20 Example (mass, gm) Tg 27 28 29 30 31 32 33 PIB diacrylate −67 62.7 62.7 62.7 62.7 62.7 62.7 62.7 FA-513M 175 10.5 10.5 12.6 FA-513AS 140 isobornyl acrylate 88 20.9 12.6 isobornyl methacrylate 110 20.9 trimethylcyclohexyl methacrylate 145 stearyl acrylate 35 isooctyl acrylate −54 Isodecyl acrylate −60 8.4 8.4 Isodecyl methacrylate −41 10.5 n-lauryl methacrylate −65 20.9 10.5 1,12-dodecanediol −37 dimethacrylate Irgacure 819 0.8 0.8 0.8 0.8 0.8 0.8 0.8 Irganox 1010 0.8 0.8 0.8 0.8 0.8 0.8 0.8 Aerosil R106 4.1 4.1 4.1 4.1 4.1 4.1 4.1 H30Ry 4.2 4.2 4.2 4.2 4.2 4.2 4.2 2 cSt polyalphaolefin diluent 5.0 9 cSt polyalphaolefin diluent uncured viscosity (cps, 25° C., 69000 185000 184000 292000 228000 211000 345000 12/s) Shore A hardness 29 48 53 53 53 43 79 tensile strength (psi) 217 544 612 812 590 465 1134 elongation (%) 157 171 194 217 187 189 213 100% modulus (psi) 118 279 278 293 280 209 526 compression set A (% 25%) 7 5 11 4 7 3 11 compression set B (% 25%) 11 24 38 26 31 17 61 Example (mass, gm) Tg 34 35 36 37 38 39 40 PIB diacrylate −67 62.7 62.7 62.7 62.7 62.7 62.7 62.7 FA-513M 175 FA-513AS 140 isobornyl acrylate 88 15.7 15.7 15.7 20.9 20.9 isobornyl methacrylate 110 trimethylcyclohexyl methacrylate 145 20.9 stearyl acrylate 35 20.9 isooctyl acrylate −54 5.2 Isodecyl acrylate −60 4.2 Isodecyl methacrylate −41 n-lauryl methacrylate −65 1,12-dodecanediol −37 5.2 1.0 dimethacrylate Irgacure 819 0.8 0.8 0.8 0.8 0.8 0.8 0.8 Irganox 1010 0.8 0.8 0.8 0.8 0.8 0.8 0.8 Aerosil R106 4.1 4.1 4.1 4.1 4.1 4.1 4.1 H30Ry 4.2 4.2 4.2 4.2 4.2 4.2 4.2 2 cSt polyalphaolefin diluent 9 cSt polyalphaolefin diluent 4.0 uncured viscosity (cps, 25° C., 200000 200000 122000 260000 226000 257000 178000 12/s) Shore A hardness 45 69 42 68 50 50 45 tensile strength (psi) 478 883 218 924 598 614 428 elongation (%) 179 201 111 100 161 205 191 100% modulus (psi) 235 409 194 824 309 241 189 compression set A (% 25%) 5 8 3 6 3 12 14 compression set B (% 25%) 21 51 7 41 19 35 30 Example (mass, gm) Tg 41 42 43 44 PIB diacrylate −67 62.7 62.7 67.5 67.4 FA-513M 175 FA-513AS 140 isobornyl acrylate 88 20.9 20.9 16.9 16.8 isobornyl methacrylate 110 trimethylcyclohexyl methacrylate 145 stearyl acrylate 35 isooctyl acrylate −54 5.6 5.6 Isodecyl acrylate −60 2.6 Isodecyl methacrylate −41 n-lauryl methacrylate −65 1,12-dodecanediol −37 0.5 0.5 dimethacrylate lauroyl peroxide 1.0 Irgacure 819 0.8 0.8 0.9 Irganox 1010 0.8 0.8 0.9 0.9 Aerosil R106 4.1 4.1 3.2 3.2 H30Ry 4.2 4.2 4.5 4.5 2 cSt polyalphaolefin diluent 9 cSt polyalphaolefin diluent uncured viscosity (cps, 25° C., 169000 348000 177000 100000 12/s) Shore A hardness 43 48 45 44 tensile strength (psi) 523 612 534 413 elongation (%) 209 220 212 150 100% modulus (psi) 203 243 196 235 compression set A (% 25%) 11 11 11 compression set B (% 25%) 34 31 26 1Glassy monomer marketed by Hitachi Chemical Corporation.

Example 43 is a UV curable composition. Example 43 was formed into samples. The samples were exposed to an UV A radiation source having an intensity of about 1434 mw/cm2 for an energy of about 9872 mJ/cm2. Cured samples of composition 43 had a sealing force at −40° C. of 8N at 25% compression. Example 44 is a thermally curable composition.

The sealing force for example 24 is shown in the table below as a function of temperature and percent compression. The composition in example 24 exhibits typical elastomeric properties. The sealing force at a constant temperature increases as the percent compression is increased, which is expected based on the theory of rubber elasticity as the extension increases. The force, at a constant compression, increases as the temperature is increased. This is also expected based on the temperature dependency defined in the equation of state of rubber elasticity.

Sealing Force (Newtons) vs Compression UV Cured Polyisobutylene, Example 24 Temperature Compression −40° C. 23° C. 95° C.  5% 3 3 28 10% 3 21 66 15% 5 28 81 20% 6 48 103 25% 9 70 154 40% 18 154 289

The sealing force at −40° C. for several cured films that were compressed twenty-five percent are shown in the table below, titled UV cured Isoprene & PIB Cured-In-Place Gasketing Compositions. It was observed as shown in examples 1, 2 and 3 that the sealing force at −40° C. and 25 percent compression varied significantly as a function of the monomer content as shown in the table and graph below. The step function in change from examples 1, 2, and 3 was surprising and not expected based on observing a single glass transition temperature in the DSC scan. If there was a distinct or separate glassy phase that occurred as a result of the higher glass transition monomer, it should appear as a first or second order thermodynamic transition as measured by DSC. No such first or second order thermodynamic transition is observed in the DSC scans for examples 1, 2 and 3 shown in the figures. High monomer content is desirable to lower the viscosity of the uncured sealant. This allows the sealant to be dispensed quickly while obtaining a cured elastomer with high tensile strength and high elongation. As the monomer content decreases the viscosity increases, tensile strength decreases and the elongation decreases. A high viscosity is undesirable as it is difficult to rapidly dispense the composition. A low elongation is undesirable which can lead to cracks in the seal. A high sealing force at low temperature is desirable as this defines the practical lower limit of ability of the elastomeric seal to perform its intended function over the operating temperature range. The low temperature sealing force, i.e. at −40° C., can be modulated dramatically with changes in the glassy and/or rubbery monomer ratio.

Each of these cured networks exhibited a single glass transition temperature when measured with a differential scanning calorimetry (DSC) as shown in FIGS. 2, 3 and 4 (Examples 1, 24 and 30).

While preferred embodiments have been set forth for purposes of illustration, the description should not be deemed a limitation of the disclosure herein. Accordingly, various modifications, adaptations and alternatives may occur to one skilled in the art without departing from the spirit and scope of the present disclosure.

UV cured Isoprene & PIB Cured-in-Place Gasketing Compositions 25% Compression Sealing Force Example 45 1 2 3 30 34 24 PIB-Diacrylate 100.0 100.0 100.0 100.0 100.0 100.0 Kuraray UC-203 100.0 FA-513M, Tg = 175° C. 33.3 33.3 25.0 17.7 Isobornyl Acrylate Tg = 88° C. 33.3 25.0 25.0 isooctyl acrylate Tg = −54° C. 8.3 8.3 Sartomer Ricacryl 3850 6.7 2 cst PAO 8.0 8.0 7.6 7.1 BHT 1.3 Tinuvin 765 1.3 Darocur 1173 4.0 1,12-dodecanediol dimethacrylate 0.8 Irgacure 819 1.3 3.6 1.2 1.1 1.3 1.3 1.3 I-1010 1.3 1.3 1.2 1.3 1.3 1.3 Aerosil R106 6.5 6.5 6.2 5.7 6.5 6.5 4.8 H30RY 6.7 6.7 6.3 5.9 6.7 6.7 6.7 Total 169.2 159.4 147.6 138.6 149.1 149.1 148.2 Viscosity (cps, 25° C., 12/s) 82,100 180,200 288,700 456,600 291,900 200,200 177,200 Shore A, ASTM D2240 44 64 55 45 53 45 45 Tensile (psi) ASTM D412 871 1084 727 543 812 478 572 Elongation (%) ASTM D412 150 225 195 174 217 179 197 100% modulus (psi), D412 483 460 323 264 293 235 222 CS % (25%), ASTM D395 — 9 5 6 4 5 7 CS % (25%), Cooled closed fixture 62 41 27 26 21 26 Tg, Degree ° C. −61 −61 −63 −64 −58 −59 −59 Other DSC Transitions none none none none none none none −40° C. force, 25% comp. (Newtons) 4 5 6 15 6 11 8

Examples of glassy or rubbery monomers. Tg VISCOSITY COMPANY PRODUCT DESCRIPTION CAS # (° C.) (mPa · s) MW (Da) AkzoNobel Nourycryl MC 110 4-tert-Butylcylcohexyl Methacryalte AkzoNobel Nourycryl MA 123- Ethylene Ureaethyl Methacrylate M50 50% in MMA AkzoNobel Nourycryl MA 128 2,2-Pentamethylene-1,3- oxazolidyl-3) Ethylmethacryate Arkema MA: Methyl Methyl Acrylate 96-33-3 10 Acrylate Arkema Norsocryl ® Tetrahydrofurfuryl Methacrylate 2455-24-5 60 Tetrahydrofurfuryl Methacrylate (THFMA) Arkema MATRIFE Trifluoroethyl methacrylate (Trifluoroethyl methacrylate) Arkema Norsocryl ® Methacrylic Anhydride Methacrylic Anhydride (Norsocryl ® 500) Arkema LMA: Norsocryl ® Lauryl Methacryalate 142-90-5 −65 Lauryl 2549-53-3 Methacrylate 2495-27-4 Arkema SMA: Norsocryl ® Stearyl Methacrylate 2495-27-4 −100 Stearyl 32360-05-7 Methacrylate Arkema A18-22: Behenyl Acrylate 4813-57-4 Norsocryl ® 48076-38-6 Acrylate C18-22 18299-85-9 Arkema Norsocryl ® 121: Alkyl Acrylate in aromatic Norsocryl ® hydrocarbon (40/60) Acrylate C18-44 in solution in aromatic hydrocarbon solvents (40/60) Arkema Norsocryl ® Heptyl Heptyl Methacrylate Methacrylate (HMA) Arkema EA: Ethyl Acrylate Ethyl Acrylate 140-88-5 −24 Arkema BA: Butyl Acrylate Butyl Acrylate 141-32-2 −54 Arkema 2EHA: 2- 2-Ethylhexyl Acrylate 103-11-7 −70 Ethylhexyl Acrylate Arkema Norsocryl ® 102: 2-ethyl (2-oxoimidazolidin-1-yl) 25% MEIO methacrylate (MEIO), an ureido monomer, as two solutions in methyl methacrylate: Arkema Norsocryl ® 104: 2-ethyl (2-oxoimidazolidin-1-yl) 50% MEIO methacrylate (MEIO), an ureido monomer, as two solutions in methyl methacrylate: Arkema Norsocryl ® 402: Methoxy PEG 2000 Methacrylate Methoxy PEG 2000 Methacrylate Arkema Norsocryl ® 405: Methoxy PEG 5000 Methacrylate Methoxy PEG 5000 Methacrylate Arkema Norsocryl ® Allyl Allyl Methacrylate 96-05-9 Methacrylate (AMA) BASF Dihydrocyclopentadienyl Dihydrocyclopentadienyl Acrylate 12542-30-2 110 204 Acrylate (DCPA) BASF Tertiarybutyl Tertiarybutyl acrylate 1663-39-4 55 128 acrylate (TBA) BASF Cyclohexyl Cyclohexyl Methacrylate 101-43-9 83 168 Methacrylate (CHMA) BASF Tertiarybutyl Tertiarybutyl methacrylate 585-07-9 107 142 methacrylate (TBMA) BASF tert-Butyl tert-Butyl Methacrylate low acid 585-07-9 114 142 Methacrylate low acid (TBMA LA) BASF tert-Butyl tert-Butyl Methacrylate low 585-07-9 114 142 Methacrylate low stabilizer stabilizer (TBMA LS) BASF Ureido Ureido Methacrylate 25% in MMA 86261-90-7 198 Methacrylate 25% in MMA (UMA 25%) BASF N,N- N,N-Dimethylaminoethyl 2867-47-2 157 Dimethylaminoethyl Methacrylate Methacrylate (DMAEMA) BASF N,N- N,N-Diethylaminoethyl 105-16-8 144 Diethylaminoethyl Methacrylate Methacrylate (DEAEMA) BASF tert- tert-Butylaminoethyl Methacrylate 3775-90-4 185 Butylaminoethyl Methacrylate (TBAEMA) BASF Hydroxypropyl Hydroxypropyl acrylate 25584-83-2 24 acrylate (HPA) BASF 2-Ethylhexyl 2-Ethylhexyl acrylate 103-11-7 50,-68  acrylate (2-EHA) BASF 4-Hydroxybutyl 4-Hydroxybutyl acrylate 2478-10-6 144 acrylate (4HBA) BASF Ethyldiglycol Ethyldiglycol acrylate 7328-17-8 188 acrylate (EDGA) BASF Allyl Methacrylate Allyl Methacrylate 96-05-9 52 126 (AMA) BASF Behenyl Acrylate Behenyl Acrylate 4813-57-4 325 (BEA) (C18) BASF Lauryl Lauryl Methacrylate 142-90-5 Methacrylate (C12) (LMA) 2549-53-3 (C14) 2495-27-4 (C16) BASF Stearyl Stearyl Methacrylate 2495-27-4 Methacrylate (C16) (SMA) 32360-05-7 (C18) BASF Behenyl Behenyl Methacrylate 32360-05-7 Methacrylate (C18) (BEMA) 45294-18-6 (C20) 16669-27-5 (C22) BASF Stearyl Acrylate Stearyl Acrylate 4813-57-4 (SA) (C16) 13402-02-3 296 (C18) BASF Lauryl acrylate Lauryl acrylate 2156-97-0 −3 240 (LA) Butyl acrylate (BA) Butyl acrylate 141-32-2 −43 128 Isodecyl Acrylate Isodecyl Acrylate 1330-61-6 −60 (IDA) BASF Isobutyl acrylate Isobutyl acrylate 106-63-8 128 (IBA) Hydroxyethyl Hydroxyethyl acrylate 818-61-1 −15 116 acrylate (HEA) 2-Propylheptyl 2-Propylheptyl Acrylate high grade 149021-58-9 −7 130 Acrylate high grade (2-PHA HG) BASF 2-Propylheptyl 2-Propylheptyl Acrylate techn. 149021-58-9 −7 130 Acrylate techn. (2- PHA TG) Methacrylic Acid Methacrylic Acid 79-41-4 228 1.4  86 (MAA) tert-Butyl tert-Butyl Methacrylate 585-07-9 107 0.93 142 Methacrylate (TBMA) Bimax BETA-C 2-Carobxyethyl Acrylate 24615-84-7 <30 — 144 Bimax BX-ADMA 1-Adamantyl Methacrylate 16887-36-8 — viscous liq. 220 Bimax BX-PTEA Phenylthioethyl Acrylate 95175-38-5 — — 208 Bimax BX-DMANPA Dimethylaminoneopentyl acrylate 20166-73-8 285 Bimax BX-NASME N-Acryloyl sarcosine methyl ester 72065-23-7 157 Bimax BX-BHPEA 2-(4-Benzoyl-3- 16432-81-8 312 hydroxyphenoxy)ethyl acrylate Bimax BX-AHBP 4-Allyloxy-2-hydroxy 2549-87-3 254 benzophenone Bimax BX-DCPA Dicyclopentenyl acrylate 33791-58-1 204 Bimax BX-DCPMA Dicyclopentenyl methacrylate 51178-59-7 218 Bimax BX-HEMA 2-Hydroxyethyl methacrylate 868-77-9 130 Bimax BX-EOEMA 2-Ethoxyethyl methacrylate 2370-63-0 158 Bimax BX-TFEMA Trifluoroethyl methacrylate 352-87-4 168 Bimax BX-MAA Methacrylic acid 79-41-4  86 Bimax HEMA-5 Polyethoxy (5) methacrylate 95% active Bimax HEMA-10 Polyethoxy (10) methacrylate 90% active Bimax BEM-25 Behenylpolyethoxy (25) waxy solid methacrylate 93% active Bimax LEM-23 Laurylpolyethoxy (23) methacrylate 93% active Bimax MPEM-7 Methoxypolyethoxy (7) methacrylate 95% active Bimax MPEM-12 Methoxypolyethoxy (12) methacrylate 95% active Bimax MPEM-16 Methoxypolyethoxy (16) methacrylate 95% active Bimax Development 3-PHENOXY-2-HYDROXY product 2 PROPYL METHACRYLATE Bimax Development METHOXYETHOXYETHYL product 3 METHACRYLATE Cytec B-CEA β-carboxyethyl acrylate 24615-84-7 <30 75 144 Cytec IBO-A Isobornyl Acrylate 5888-33-5 95 9 208 Cytec EBECRYL 110 Oxyethylated Phenol Acrylate 56641-05-5 −8 13-27 236 Cytec EBECRYL 113 Mono-functional aliphatic epoxy 6  90-150 acrylate Cytec EBECRYL 114 2-Phenoxyethyl Acrylate 48145-04-6 5 20 max 192 Cytec EBECRYL 1039 Urethane Mono Acrylate 20-50 Cytec ODA-N Octyl/Decyl Acrylate 2499-59-4 −65 2-3 184 2156-96-9 312 Dow Glacial Acrylic Glacial Acrylic Acid 79-10-7 106 1.2  72 Chemical Acid (GAA) 99.0% Dow Methyl Acrylate Methyl Acrylate 96-33-3 8 0.5  86 Chemical (MA) Dow Glacial Acrylic Glacial Acrylic Acid 79-10-7 106 1.2  72 Chemical Acid (GAA-FG) Floculant Grade 99.6% Dow Ethyl Acrylate (EA) Ethyl Acrylate 140-88-5 −71 0.6 100 Chemical Dow Butyl Acrylate (BA) Butyl Acrylate 141-32-2 −54 0.9 128 Chemical Dow 2-Ethylhexyl 2-Ethylhexyl Acrylate 103-11-7 −85 1.7 184 Chemical Acrylate (2-HEA) Hitachi FA-512M (500-600 ppm Dicyclopentenyloxyethyl 68586-19-6 40-50 15-20 262 MEHQ) Methacrylate Hitachi FA-512MT Dicyclopentenyloxyethyl 68586-19-6 40-50 15-20 262 (325-375 ppm Methacrylate PTZ + 22-28 ppm HQ) Hitachi FA-THFA Tetrahydrofurly Acrylate 2399-48-6 — 1-5 156 Hitachi FA-BZA Benzyl Acrylate 2495-35-4 — 3-8 162 Hitachi FA-THFM Tetrahydrofurfyl Methacrylate 2455-24-5 —  8-18 170 Hitachi FA-BZM Benzyl Methacrylate 2495-37-6 — 2-3.5 (20° C.) 176 Hitachi FA-310A Phenoxyethyl Acrylate 48145-04-6 —  3-13 192 Hitachi FA-711MM Pentamethylpiperldinyl 68548-08-3 — 11-14 239 Methacrylate Hitachi FA-314A Nonylphenoxypolyethylene Glycol 50974-47-5 — 120-180 452 Acrylate Hitachi FA-318A Nonylphenoxypolyethylene Glycol 50974-47-5 — 120-180 626 Acrylate Hitachi FA-511AS Dicyclopentenyl Acrylate 33791-58-1 10-15  8-18 204 Hitachi FA-512AS Dicyclopentenyloxyethyl Acrylate 65983-31-5 10-15 15-25 248 Hitachi FA-513M Dicyclopentanyl Methacrylate 34759-34-7 175  7-17 220 Hitachi FA-513AS Dicyclopentanyl Acrylate 79637-74-4 120  7-17 206 Hitachi FA-310M Phenoxyethyl Methacrylate 10595-06-9 36  3-13 206 Hitachi FA-712HM Tetramethylpiperldinyl 31582-45-3 — 3-6 (60° C.) 225 Methacrylate Hitachi FA-400M(100) Methoxy Polyethylene Glycol 26915-72-0 — 20-30 496 Methacrylate Jarchem Jarchem ® LA Lauryl Acrylate 2156-97-0 Jarchem Jarchem ® LMA Lauryl Methacrylate 142-90-5 Jarchem Jarchem ® SA Stearyl Acrylate 4813-57-4 Jarchem Jarchem ® SMA Stearyl Methacrylate 32360-05-7 Kyyoeisha LIGHT ESTER BZ Benzyl methacrylate 2495-37-6 54 3 Kyyoeisha LIGHT ESTER IB Isobutyl methacrylate 97-86-9 48 2 Kyyoeisha LIGHT ESTER G Glycidyl methacrylate 106-91-2 46 Kyyoeisha LIGHT ESTER S n-Stearyl methacrylate 32360-05-7 38 9 Kyyoeisha LIGHT ESTER 2-Hydroxpropyl methacrylate 923-26-2 26 10 HOP(N) Kyyoeisha LIGHT ESTER DE Diethylaminoethyl methacrylate 105-16-8 20 Kyyoeisha LIGHT ESTER NB n-Butyl metacrylate 97-88-1 20 Kyyoeisha LIGHT ESTER DM Dimethylaminoethyl methacrylate 2867-47-2 18 3 Kyyoeisha EPOXY ESTER 2-hydroxy 3-phenoxy propyl 16969-10-1 17 175 M-600A acrylate Kyyoeisha LIGHT Lauryl acrylate 2156-97-0 −3 4 ACRYLATE L-A Kyyoeisha LIGHT ESTER 2-Hydroxypropyl acrylate 25584-83-2 −7 6 HOP-A(N) Kyyoeisha LIGHT ESTER 2-Hydroxypropyl acrylate 25584-83-2 −7 HOP-A(N) Kyyoeisha LIGHT ESTER EH 2-Ethyl hexyl methacrylate 688-84-6 −10 3 Kyyoeisha LIGHT ESTER 2-Hydroxyethyl acrylate 818-61-1 −15 5 HOA(N) Kyyoeisha LIGHT ESTER 2-Hydroxyethyl acrylate 818-61-1 −15 HOA(N) Kyyoeisha LIGHT Phenoxy ethyl acrylate 48145-04-6 −22 13 ACRYLATE PO-A Kyyoeisha LIGHT Phenoxy polyethyleneglycol 56641-05-5 −25 11 ACRYLATE P- acrylate 200A Kyyoeisha HOA-MS(N) 2-Acryloyloxy ethyl succunate 50940-49-3 −40 180 Kyyoeisha LIGHT ESTER ID Isodecyl methacrylate 29964-84-9 −41 Kyyoeisha LIGHT Isoamyl acrylate 4245-35-6 −45 2 ACRYLATE IAA Kyyoeisha LIGHT Methoxy triethyleneglycol acrylate 32171-39-4 −50 6 ACRYLATE MTG-A Kyyoeisha LIGHT ESTER L n-Lauryl methacrylate 142-90-5 −65 6 Kyyoeisha LIGHT Ethoxy diethyleneglycol acrylate 7328-17-8 −70 5 ACRYLATE EC-A Kyyoeisha HOA-MPE(N) 2-Acryloyloxy ethyl 2-hydroxy ethyl 38056-88-1 800 phthalate Kyyoeisha LIGHT 2-Acryloyloxy ethyl phosphate 32120-16-4 23000 ACRYLATE P- 1A(N) Kyyoeisha HOA-MPL(N) 2-Acryloyloxy ethyl phthalate 30697-40-6 7500 Kyyoeisha LIGHT 2-Acryloyloxyethyl hexahydro 57043-35-3 6000 ACRYLATE HOA- phthalate HH(N) Kyyoeisha LIGHT 2-Ethyl hexyl diglycol acrylate 117646-83-0 7 ACRYLATE EHDG-AT Kyyoeisha LIGHT 2-Hydroxy butyl acrylate 2421-27-4 9 ACRYLATE HOB-A Kyyoeisha LIGHT ESTER 2-Hydroxybutyl methacrylate 13159-51-8 HOB(N) Kyyoeisha LIGHT ESTER P- 2-Methacryloyloxyethyl acid 52628-03-2 5250 1M phoshate Kyyoeisha LIGHT ESTER 2-Methacryloyloxyethyl 51252-88-1 HO-HH(N) hexahydrophthalate Kyyoeisha LIGHT ESTER 2-Methacryloyloxyethyl succynic 20882-04-6 HO-MS(N) acid Kyyoeisha LIGHT ESTER PO 2-Phenoxy ethyl methacrylate 10595-06-9 7 Kyyoeisha LIGHT ESTER L-7 Alkyl(C12~C13) methacrylate 142-90-5/ C12?45%, C12?55% 2495-25-2 Kyyoeisha LIGHT Arcylate of ethyleneoxide modified 50974-47-5 100 ACRYLATE NP- nonylphenol 4EA Kyyoeisha LIGHT ESTER BC Butoxy diethyleneglycol 7328-22-5 methacrylate Kyyoeisha LIGHT Methoxy dipropyleneglycol acrylate 83844-54-6 3 ACRYLATE DPM-A Kyyoeisha LIGHT Methoxy polyethylenegrycol 32171-39-4 25 ACRYLATE 130A acrylate Kyyoeisha LIGHT ESTER Methoxy polyethylenegrycol 26915-72-0 25 130MA methacrylate Kyyoeisha LIGHT ESTER Methoxy polyethylenegrycol 26915-72-0 041MA methacrylate Kyyoeisha LIGHT Neopenthylglycol benzoate 66671-22-5 70 ACRYLATE BA- acrylate 104 Kyyoeisha LIGHT Phenoxy diethyleneglycol acrylate 61630-25-9 11 ACRYLATE P2H-A Kyyoeisha LIGHT Stearyl acrylate 4813-57-4 9 ACRYLATE S-A Kyyoeisha LIGHT Tetrahydrofurfuryl acrylate 2399-48-6 5 ACRYLATE THF-A Kyyoeisha LIGHT ESTER M- Trifluoroethyl methacrylate 352-87-4 3 3F Kyyoeisha LIGHT Dimethylol tricylco decane 352-87-4 ACRYLATE DCP-A diacrylate Lucite Methyl Methyl Methacrylate 80-62-6 105 0.56 100 Methacrylate (MMA) Mitsubishi Methyl Methyl Methacrylate 80-62-6 105 0.56 100 Rayon Methacrylate (MMA) Mitsubishi Cyclohexyl Cyclohexyl Methacrylate 101-43-9 83 2.5 168 Rayon Methacrylate (CHMA) Mitsubishi Ethyl Methacrylate Ethyl Methacrylate 97-63-2 65 0.62 114 Rayon (EMA) Mitsubishi 2-Hydoxyethyl 2-Hydoxyethyl Methacrylate 868-77-9 55 6.8 130 Rayon Methacrylate (HEMA) Mitsubishi Benzyl Benzyl Methacrylate 2495-37-6 54 2.7 176 Rayon Methacrylate (BZMA) Mitsubishi Allyl Methacrylate Allyl Methacrylate 96-05-9 52 1.1 126 Rayon (AMA) Mitsubishi iso-Butyl iso-Butyl Methacrylate 97-86-9 48 0.88 142 Rayon Methacrylate (IBMA) Mitsubishi Glycidyl Glycidyl Methacrylate 106-91-2 46 2.5 142 Rayon Methacrylate (GMA) Mitsubishi Hydroxypropyl Hydroxypropyl Methacrylate 27813-02-1 26 9.3 144 Rayon Methacrylate (HPMA) Mitsubishi n-Butyl n-Butyl Methacrylate 97-88-1 20 0.92 142 Rayon Methacrylate (BMA) Mitsubishi Diethylaminoethyl Diethylaminoethyl Methacrylate 105-16-8 16~24 1.8 185 Rayon Methacrylate (DEMA) Mitsubishi Dimethylaminoethyl Dimethylaminoethyl Methacrylate 2867-47-2 18 1.3 157 Rayon Methacrylate (DMMA) Mitsubishi 2-Ethylhexyl 2-Ethylhexyl Methacrylate 688-84-6 −10 1.85 198 Rayon Methacrylate (EHMA) Mitsubishi 2-Ethoxyethyl 2-Ethoxyethyl Methacrylate 2370-63-0 −31 3.5 158 Rayon Methacrylate (ETMA) Mitsubishi Tridecyl Tridecyl Methacrylate 2495-25-2 −46 5.8 268 Rayon Methacrylate (TDMA) Mitsubishi Alkyl Methacrylate Alkyl Methacrylate 142-90-5 −62 5.1 263 (avg) Rayon (SLMA) 2495-25-2 Mitsubishi Lauryl Lauryl Methacrylate 142-90-5 −65 4.6 255 Rayon Methacrylate (LMA) Mitsubishi Stearyl Stearyl Methacrylate 32360-05-7 −100 8.2 339 Rayon Methacrylate (@30° C.) (SMA) Mitsubishi 2-Methoxyethyl 2-Methoxyethyl Methacrylate 6976-93-8 144 Rayon Methacrylate (MTMA) Mitsubishi Tertahydrofurfuryl Tertahydrofurfuryl Methacrylate 2455-24-5 170 Rayon Methacrylate (THFMA) MRC Unitec TBCHMA 4-tbutylcyclohexyl methacrylate 46729-07-1 224 MRC Unitec MBP 4-methacryloxyoxybenzophenone 56467-43-7 solid 266 MRC Unitec MEU 2- 3089-23-4 solid 255 (methacryloxyoxyaceamidoethylene)N, N′-ethyleneurea Nippon (CHDMMA) 1,4-Cyclohexanedimethanol 23117-36-4 18 88 198 Kasei Monoacrylate Nippon (4HBAGE) 4-Hydroxybutyl Acrylate 119692-59-0 −64 7 200 Kasei Glycidylether Nippon (4HBA) 4-Hydroxybutyl Acrylate 2478-10-6 −40 10.2 144 Kasei Osaka IBXA Iso-Bornyl Acylate 5888-33-5 97 7.7 208 Organic Chemicals Osaka Viscoat 3FM 2,2,2-Trifluoroethyl Methacrylate 352-87-4 81 1 168 Organic Chemicals Osaka TBA (C4) Tert.-butyl Acrylate 1663-39-4 41 1.3 128 Organic Chemicals Osaka Viscoat 8FM 1H,1H,5H-Octafluoropentyl 355-93-1 36 4.1 300 Organic Methacrylate Chemicals Osaka STA (C18) Stearyl Acrylate 4813-57-4 30 8.6 325 Organic (30° C.) Chemicals Osaka CHDOL-10 Cyclohexanesppiro-2-(1,3-dioxate- 97773-09-6 22 16.9 154 Organic 4-yl) Methyl Acrylate Chemicals Osaka LA (C12) Lauryl Acrylate 2156-97-0 15 4 240 Organic Chemicals Osaka Viscoat#155 Cyclohexyl Acrylate 3066-71-5 15 2.5 154 Organic (CHA) Chemicals Osaka Viscoat#160 (BZA) Benzyl Acrylate 2495-35-4 6 8 162 Organic Chemicals Osaka OXE-30 3-Ethyl-3-oxetanyl Methacrylate 37674-57-0 2 4.1 192 Organic Chemicals Osaka OXE-10 3-Ethyl-3-oxanylmethyl Acrylate 41988-14-1 — 4.3 162 Organic Chemicals Osaka GBLMA gamma-Butylolactone 195000-66-9 — Mp = 22-24 170 Organic Methacrylate Chemicals Osaka Viscoat 3F 2,2,2-Trifluoroethyl Acrylate 407-47-6 −5 1.1 154 Organic Chemicals Osaka Viscoat#150 Tetrahydofurfuryl Acrylate 2399-48-6 −12 2.8 156 Organic (THFA) Chemicals Osaka Viscoat 8F 1H,1H,5H-Octafluoropentyl 376-84-1 −35 3.1 286 Organic Acrylate Chemicals Osaka Viscoat 4F 2,2,3,3-Tetrafluropropyl Acrylate 7283-71-3 — 1.9 186 Organic Chemicals Osaka HPA 2-hydroxypropyl Acrylate 25584-83-2999- −7 4.1 130 Organic 61-1 Chemicals Osaka MEDOL-10 (2-Ethyl-2-methyl-1,3-dioxolate-4- 69701-99-1 −7 5.1 208 Organic yl) Methyl Acrylate Chemicals Osaka HEA Hydroxyethyl Acrylate 818-61-1 −15 5.9 116 Organic Chemicals Osaka ISTA (C18) Iso-Steryl Acrylate 93841-48-6 −18 17 325 Organic Chemicals Osaka Viscoat#192 (PEA) Phenoxyethyl Acrylate 48145-04-6 −22 8.7 192 Organic Chemicals Osaka 4-HBA 4-hydroxybutyl Acrylate 10/6/2478 −32 5.5 144 Organic Chemicals Osaka 2-MTA 2-Methoxyethyl Acrylate 3121-61-7 −50 1.5 130 Organic Chemicals Osaka IOAA (C8) Iso-Octyl Acylate 29590-42-9 −58 2-4 184 Organic Chemicals Osaka INAA (C9) Iso-Nonyl Acrylate 51952-49-9 −58 — 198 Organic Chemicals Osaka NOAA (C8) N-Ocyl Acrylate 2499-59-4 −65 — 184 Organic Chemicals Osaka Viscoat 190 Ethoxyethoxyethyl Acrylate 7328-17-8 −67 2.9 188 Organic (EOEOEA, CBA) Chemicals Osaka Viscoat MTG Methoxytriethyleneglycol Acrylate 48067-72-7 — — 218 Organic Chemicals Osaka MPE400A Methoxypolyethyleneglycol 32171-39-4 — 25-30 470 Organic Acrylate Chemicals Osaka MPE550A Methoxypolyethyleneglycol 32171-39-4 — 50-60 620 Organic Acrylate Chemicals Osaka GBLA gamma-Butylolactone Acrylate 328249-37-2 — — 156 Organic Chemicals Osaka V#2100 acid functional acrylate 121915-68-2 —  5,000-10,000 278 Organic Chemicals Osaka V#2150 acid functional acrylate 61537-62-0 — 8,200 284 Organic Chemicals Osaka Viscoat#315 Structure only (Bis-F, PEG — 170 226 + 44n Organic acrylate) Chemicals Polysciences 24891-100 Beta-Carboxyethyl Acrylate, >98% 24615-84-7 144 Active Polysciences 02092-5 Cinnamyl methacrylate 31736-34-2 202 Polysciences 22493-100 iso-Decyl methacrylate, min. 90% 29964-84-9 226 Polysciences 24897-250 Methacrylic Acid, 99.9% 79-41-4  86 Polysciences 24360-10 o-Nitrobenzyl methacrylate, min. 95% Polysciences 06344-10 Pentabromophenyl acrylate 52660-82-9 solid 542 Polysciences 04253-10 Pentabromophenyl methacrylate 18967-31-2 solid 557 Polysciences 06349-5 Pentafluorophenyl acrylate 71195-85-2 238 Polysciences 06350-5 Pentafluorophenyl methacrylate, 13642-97-2 252 95% Polysciences 16712-100 Poly(ethylene glycol) (n) 25736-86-1 MW of monomethacrylate PEG Block = 200 Polysciences 16713-100 Poly(ethylene glycol) (n) 25736-86-1 MW of monomethacrylate PEG Block = 400 Polysciences 16664-500 Poly(ethylene glycol) (n) 26915-72-0 MW of monomethyl ether PEG monomethacrylate Block = 200 Polysciences 15934-250 Poly(propylene glycol) (300) 39240-45-6 MW of monomethacrylate PEG Block ~370 Polysciences 06127-10 tert-Amyl Methacrylate 2397-76-4 156 Polysciences 03057-10 Tribromoneopentyl methacrylate CASRN03057 393 Polysciences 18556-500 Triethylene glycol monoethyl ether 39670-09-2 246 monomethacrylate Polysciences 02544-25 Undecyl methacrylate 16493-35-9 240 San Esters ADMA 1-Adamantyl Methacrylate 16887-36-8 220 San Esters MADMA 2-Methyl-2-Adamantyl 177080-67-0 234 Methacrylate San Esters MADA 2-Methyl-2-Adamantyl Acrylate 249562-06-9 220 San Esters EtADA 2-Ethyl-3-Adamantyl Acrylate 303186-14-3 234 San Esters EtADMA 2-Methyl-2-Adamantyl Acrylate 209982-56-9 Solid 220 San Esters ADA 1-Adamantyl Acrylate 121601-93-2 Solid 206 Sartomer SR423A Isobornyl Methacrylate 7534-94-3 110 11 — Sartomer SR506A Isobornyl Acrylate 5888-33-5 95 8 Sartomer SR340 2-Phenoxyethyl Methacrylate 10595-06-9 54 10 206 Sartomer CD535 Dicyclopentandienyl Methacrylate 31621-69-9 45 8 218 Sartomer CD590 Aromatic Acrylate Monomer proprietary 38 180 — Sartomer SR324 Stearyl Methacrylate 32360-05-7 38 14 338 2495-27-4 (33%) Sartomer SR257 Stearyl Acrylate 4813-57-4 35 MP = 24 324 Sartomer CD420 Acrylic Monomer Proprietary 29 6 — Sartomer SR531 Cyclic Trimethylpropane Formal 66492-51-1 10 15 200 Acrylate 15625-89-5 (5% tri- acrylate) Sartomer CD588 Acrylate Ester proprietary 6 7 — Sartomer SR339 2-Phenoxyethyl Acrylate 48145-04-6 5 12 192 Sartomer CD9087 Alkoxylated Phenol Acrylate proprietary −24 24 — Sartomer SR285 Tetrahydrofurfuryl Acrylate 2399-48-6 −28 6 156 Sartomer SR335 Lauryl Acrylate −30 Sartomer CD9088 Alkoxylated Phenol Acrylate proprietary −40 65 — Sartomer SR493D Tridecyl Methacrylate 2495-25-2 −40 6 268 Sartomer SR242 Isodecyl Methacrylate 29964-84-9 −41 5 226 Sartomer CD9075 Alkoxylated Lauryl Acrylate proprietary −45 24 — Sartomer CD553 Methoxy Polyethylene Glycol (550) 32171-39-4 −50 50 693 Monoacrylate 9004-74-4 Sartomer SR484 Octadecyl Acrylate 2499-99-4 −50 4 203 2156-96-9 Sartomer CD611 Alkoxylated Tetrahydrofurfuryl proprietary −51 11 — Acylate Sartomer SR495B Caprolactone Acrylate 110489- −53 80 344 0509 818- 61-1 Sartomer SR256 2(2-Ethoxyethoxy)-Ethyl Acrylate 7328-17-8 −54 6 188 Sartomer SR440 Iso-Octyl Acrylate 29590-42-9 −54 5 184 Sartomer SR440A Iso-Octyl Acrylate (high purity) 29590-42-9 −54 5 184 Sartomer SR489D Tridecyl Acrylate 3076-04-8 −55 7 255 Sartomer CD551 Methoxy Polyethylene Glycol (350) 32171-39-4 −57 22 550 Monoacrylate 9004-74-4 (2% di funct.) Sartomer SR395 Isodecyl acrylate 1330 −60 5 212 Sartomer SR550 Methoxy Polyethylene Glycol (350) 26915-72-0 −62 100 450 Monomethacrylate 9004-74-4 (2%) Sartomer CD552 Methoxy Polyethylene Glycol (550) 26915-72-0 −65 39 693 Monomethacrylate 9004-74- 4 (2% di funct.) Sartomer SR313A Lauryl Methacrylate 142-90-5 −65 6 254 Sartomer SR313B C12 C14 Alkyl Methacrylate 142-90-5 −65 6 254 2549-53-3 2495-27-4 Sartomer SR313D C12 C14 Alkyl Methacrylate 142-90-5 −65 6 254 2549-53-3 2495-27-4 Sartomer CD278 Acrylate Ester proprietary −74 5 — Sartomer CD545 Diethylene Glycol Methyl Ether 45103-58-0 — 3 — Methacrylate 111-77- 3 (1% di funct.) Sartomer CD585 Acrylic Ester proprietary — 8 — Sartomer CD586 Acrylic Ester proprietary — 6-9 (38° C.) — Sartomer CD587 Acrylic Ester proprietary — solid — (MP = 55° C.) Sartomer CD591 Acrylic Ester proprietary — 20 — Sartomer CD613 Ethoxylated Nonyl Phenol Acrylate 678991-31- — 75 — 6 68412-54- 4 (5-10%) Sartomer CD730 Triethylene Glycol Ethyl Ether proprietary — 6 — Methacrylate

Claims

1. A cross linkable sealant composition, prepared from:

a cross linkable elastomeric oligomer having a Tg;
a monomer having a Tg higher than the elastomeric oligomer Tg or a combination of monomers having an average Tg for the combination higher than the elastomeric oligomer Tg;
an initiator or cross-linking agent; and
optionally at least one of catalyst; filler; antioxidant; reaction modifier; adhesion promoter; diluent and coloring agent;
wherein a cured reaction product of the composition has a single Tg and retains a higher sealing force at temperatures above the cured product Tg as compared to a similar composition made as above without the monomer.

2. The composition of claim 1 wherein the cross linkable elastomeric oligomer comprises reactive moieties adjacent each end and the oligomer backbone comprises polyisobutylene.

3. The composition of claim 1 wherein the cross linkable elastomeric oligomer backbone comprises about 1% to about 100% polyisobutylene.

4. The composition of claim 1 wherein the cross linkable elastomeric oligomer has spacing between reactive moieties to provide the oligomer with elastomeric properties.

5. The composition of claim 1 wherein the cross linkable elastomeric oligomer is a telechelic, (meth)acrylate terminated polyisobutylene.

6. The composition of claim 1 wherein the monomer is reacted to the cross linkable elastomeric oligomer.

7. The composition of claim 1 wherein cured reaction products are free of first and second order thermodynamic transitions as shown by DSC.

8. A method of increasing the low temperature sealing force of a cured elastomeric sealant comprising:

providing a cross linkable sealant composition, prepared from a cross linkable elastomeric oligomer, an initiator or cross-linking agent, and optionally at least one of catalyst, filler, antioxidant, reaction modifier, and coloring agent; wherein cured reaction products of the sealant composition have a Tg; and
adding about 10 to about 30% by weight of sealant composition of a monomer having a Tg higher than the elastomeric oligomer Tg or a combination of monomers having an average Tg for the combination higher than the elastomeric oligomer Tg to form an improved sealant composition;
wherein cured reaction products of the improved sealant composition have a single Tg and have a higher sealing force at temperatures between their Tg and 0° C. than cured reaction products of the sealant composition.

9. A component defining an internal chamber, comprising:

a first predetermined sealing surface in fluid communication with the chamber;
a second predetermined sealing surface aligned with the first sealing surface and in fluid communication with the chamber; and
a cured reaction product of the composition of claim 1 disposed between the first and second predetermined sealing surfaces and sealing the chamber.

10. The component of claim 9 wherein the first sealing surface and the second sealing surface do not move in relationship to each other.

11. The component of claim 9 wherein the reaction product is adhesively bonded to only one of the first and second sealing surfaces.

12. The component of claim 9 wherein the reaction product is adhesively bonded to both the first and second sealing surfaces.

13. The component of claim 9 wherein the reaction product is liquid injection molded or molded on the sealing surface.

14. A method of using the curable composition of claim 1 as a liquid gasketing composition, comprising:

providing the composition of claim 1;
dispensing the composition onto a first predetermined sealing surface,
aligning the first predetermined sealing surface and dispensed composition with a second predetermined sealing surface; and
exposing the dispensed the composition to conditions appropriate to effect cure thereof, wherein cured reaction products of the composition have a single Tg and retain a positive sealing force at temperatures above the cured product Tg.

15. The method of claim 14 wherein the composition is cured while in contact with the first and second sealing surfaces.

Patent History
Publication number: 20130287980
Type: Application
Filed: Mar 12, 2013
Publication Date: Oct 31, 2013
Applicant: Henkel Corporation (Rocky Hill, CT)
Inventor: Henkel Corporation
Application Number: 13/796,588