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EP-4735497-A1 - DUAL CURE ADHESIVE COMPOSITION

EP4735497A1EP 4735497 A1EP4735497 A1EP 4735497A1EP-4735497-A1

Abstract

An adhesive composition is shown and described herein. The composition comprises a silylated polyurethane, an epoxy functional compound, and an amine functional compound. The compositions are provided to control the molar ratio of amine active hydrogen (AH) to epoxy (E) groups. By controlling the amine active hydrogen to epoxy molar ratio, an adhesive with excellent adhesion and strength on a variety of types of substrates is provided.

Inventors

  • DUSSAUD, ANNE
  • YOUNGBERG, MICHAEL

Assignees

  • Momentive Performance Materials Inc.

Dates

Publication Date
20260506
Application Date
20240627

Claims (20)

  1. CLAIMS What is claimed is: 1. A composition comprising: a silylated polyurethane; an amine functional compound; and an epoxy functional compound; wherein the composition has a molar ratio of amine active hydrogen to epoxy of in a range from about 0.3 to less than 0.8.
  2. 2. The composition of claim 1, wherein the composition has a molar ratio of amine active hydrogen to epoxy from about 0.3 to about 0.75.
  3. 3. The composition of claim 1, wherein the composition has a molar ratio of amine active hydrogen to epoxy of in a range from about 0.4 to about 0.7.
  4. 4. The composition of claim 1, wherein the composition has a molar ratio of amine active hydrogen to epoxy of from about 0.5 to about 0.6.
  5. 5. The composition of any of claims 1 to 4, wherein the amine functional compound is selected from a polyether amine, an amino silane, or a combination thereof.
  6. 6. The composition of claim 5, wherein the polyether amine has a weight average molecular weight of from about 150 to about 6000.
  7. 7. The composition of claims 5 or 6, wherein the composition comprises the polyether amine in an amount of from about 0.1 wt.% to about 10 wt.%, and the amino silane in an amount of from about 0.1 wt.% to about 10 wt.% based on the total weight of the composition.
  8. 8. The composition of any of claims 5 to 7, wherein the amino silane is selected from a compound of the formula: 28 33809650.1 (R 11 )(R 12 )N-R 13 -Si(OR 14 )3-h(R 15 )h; R 16 -NH-R 17 -Si(OR 18 ) 3-i (R 19 )i; (R 20 )j(R 21 O)3-jSi-R 22 -NH-R 23 -Si(OR 24 )3-k(R 25 )k; N-(R 26 -Si(OR 27 )3-m(R 28 m)3; where R 11 , R 12 , and R 16 are independently selected from H or a monovalent C1-C20 hydrocarbon; R 14 , R 15 , R 18 , R 19 , R 20 , R 21 , R 24 , R 25 , R 27 , and R 28 are independently selected from a C1-C20 monovalent hydrocarbon; R 13 , R 17 , R 22 , and R 26 are independently selected from a divalent C1-C20 hydrocarbon; h, i, j, k, and m are independently selected from 0-2.
  9. 9. The composition of any of claims 1 to 8, further comprising additive selected from pigments, fillers, curing catalysts, dyes, plasticizers, thickeners, coupling agents, extenders, volatile organic solvents, wetting agents, tackifiers, crosslinking agents, thermoplastic polymers, moisture scavengers, and UV stabilizers.
  10. 10. The composition of claim 9, wherein the catalyst is a Tin catalyst.
  11. 11. The composition of claim 9, wherein the filler is selected from organic fillers, inorganic fillers, conductive fillers, or combinations thereof.
  12. 12. The composition of claim 11, wherein the conductive filler is a thermally conductive filler selected from alumina, magnesia, ceria, hafnia, lanthanum oxide, neodymium oxide, samaria, praseodymium oxide, thoria, urania, yttria, zinc oxide, zirconia, silicon aluminum oxynitride, borosilicate glasses, barium titanate, silicon carbide, silica, boron carbide, titanium carbide, zirconium carbide, boron nitride, silicon nitride, aluminum nitride, titanium nitride, zirconium nitride, zirconium boride, titanium diboride, aluminum dodecaboride, barytes, barium sulfate, asbestos, barite, diatomite, feldspar, gypsum, hormite, kaolin, mica, nepheline syenite, perlite, phyrophyllite, smectite, talc, vermiculite, zeolite, calcite, calcium carbonate, wollastonite, calcium metasilicate, clay, aluminum silicate, talc, magnesium aluminum silicate, hydrated alumina, hydrated aluminum oxide, aluminum hydroxide, magnesium hydroxide, silica, silicon dioxide, titanium dioxide, glass fibers, glass flake, clays, exfoliated clays, or other high aspect ratio fibers, rods, or flakes, calcium carbonate, zinc oxide, magnesia, titania, calcium carbonate, talc, mica, wollastonite, alumina, aluminum nitride, graphite, graphene, aluminum powder, copper powder, bronze powder, brass powder, fibers or whiskers of carbon, graphite, silicon carbide, silicon nitride, alumina, 29 33809650.1 aluminum nitride, zinc oxide, carbon nanotubes, boron nitride nanosheets, zinc oxide nanotubes, or a combination of two or more thereof.
  13. 13. A composition comprising a first part and a second part, wherein the first part comprises (i) a silylated polyurethane and an amino functional compound, and the second part comprises (ii) an epoxy functional compound.
  14. 14. A method of forming an adhesive comprising: (i) exposing the composition of any of claims 1 to 12 to moisture; and subsequently (ii) curing the composition to a temperature of from about 50 °C to about 130 °C.
  15. 15. The method of claim 14, wherein the adhesive is formed on a substrate.
  16. 16. A method of bonding two substrates comprising: applying the composition of any of claims 1 to 12 on a first substrate; contacting a second substrate with the composition applied on the first substrate; and curing the composition at a temperature of from about 50 °C to about 130 °C.
  17. 17. The method of claim 16, wherein the first and second substrate are each independently of a type selected from a metal, a thermoplastic, a thermoset, a glass, a carbon substrate, a ceramic, cement, and wood.
  18. 18. The method of claim 16 or 17, wherein the first substrate and the second substrate are the same type of material.
  19. 19. The method of claim 17, wherein the first substrate is a thermoplastic substrate, and the second substrate is a metal substrate.
  20. 20. The method of any of claims 16 to 19, wherein the first and second substrate are each free of a primer coating. 30 33809650.1

Description

PCT PATENT APPLICATION Docket No.: 5072661 32219-01599 DUAL CURE ADHESIVE COMPOSITION FIELD OF INVENTION [0001] The present invention relates to an adhesive composition. In particular, the present invention relates to a dual cure adhesive composition comprising a silylated polyurethane, an amine functional compound, and an epoxy functional compound. The compositions exhibit high adhesion on substrates and high adhesion to substrates of different materials or classes of materials. BACKGROUND [0002] Silylated moisture curable resins have broad application as adhesive materials for use in a wide variety of applications. Such adhesives may be used in, for example, construction, transportation, and/or electronic applications to name a few. Silylated polyurethanes (SPUR) can provide an isocyanate-free alternative to polyurethane resins. Isocyanates potentially create toxicity issues in some applications. [0003] While providing an isocyanate-free alternative to polyurethanes, silylated polyurethanes may still not be a viable solution for many applications. For example, silylated polyurethanes may not exhibit suitable bonding strengths that may be necessary for many applications. Further, silylated polyurethanes may not exhibit sufficient bonding across a wide range of substrate types. [0004] Two-part polyurethane adhesives are a potential solution to provide an adhesive with the desired elasticity and strength requirements for the desired applications. Such adhesives, however, typically require the use of primers. The primers for such materials are often isocyanate-based primers, which does not achieve the goal of reducing or eliminating isocyanate from the adhesive composition. SUMMARY [0005] The following presents a summary of this disclosure to provide a basic understanding of some aspects. This summary is intended to neither identify key or critical elements nor define any limitations of embodiments or claims. Furthermore, this summary 1 33809650.1 may provide a simplified overview of some aspects that may be described in greater detail in other portions of this disclosure. [0006] Provided is an adhesive composition. The composition comprises a silylated polyurethane, an epoxy functional compound, and an amine functional compound. The compositions are provided to control the molar ratio of amine active hydrogen (AH) to epoxy (E) groups . By controlling the amine active hydrogen to epoxy molar ratio, an adhesive with excellent adhesion and strength on a variety of types of substrates is provided. [0007] In one aspect, provided is a composition comprising: a silylated polyurethane; an amine functional compound; and an epoxy functional compound; wherein the composition has a molar ratio of amine active hydrogen to epoxy of in a range from about 0.3 to less than 0.8. [0008] In one embodiment, the composition has a molar ratio of amine active hydrogen to epoxy from about 0.3 to about 0.75. [0009] In one embodiment, the composition has a molar ratio of amine active hydrogen to epoxy of in a range from about 0.4 to about 0.7. [0010] In one embodiment, the composition has a molar ratio of amine active hydrogen to epoxy of from about 0.5 to about 0.6. [0011] In one embodiment in accordance with any of the previous embodiments, the amine functional compound is selected from a polyether amine, an amino silane, or a combination thereof. [0012] In one embodiment, the polyether amine has a weight average molecular weight of from about 150 to about 6000. [0013] In one embodiment in accordance with any of the previous embodiments, the composition comprises the polyether amine in an amount of from about 0.1 wt.% to about 10 wt.%, and the amino silane in an amount of from about 0.1 wt.% to about 10 wt.% based on the total weight of the composition. [0014] In one embodiment in accordance with any of the previous embodiments, the amino silane is selected from a compound of the formula: (R11)(R12)N-R13-Si(OR14)3-h(R15)h; R16-NH-R17-Si(OR18)3-i(R19)i; (R20)j(R21O)3-jSi-R22-NH-R23-Si(OR24)3-k(R25)k; N-(R26-Si(OR27)3-m(R28m)3; where R11, R12, and R16 are independently selected from H or a monovalent C1-C20 hydrocarbon; R14, R15, R18, R19, R20, R21, R24, R25, R27, and R28 are independently selected 2 33809650.1 from a C1-C20 monovalent hydrocarbon; R13, R17, R22, and R26 are independently selected from a divalent C1-C20 hydrocarbon; h, i, j, k, and m are independently selected from 0-2. [0015] In one embodiment in accordance with any of the previous embodiments, the composition further comprises an additive selected from pigments, fillers, curing catalysts, dyes, plasticizers, thickeners, coupling agents, extenders, volatile organic solvents, wetting agents, tackifiers, crosslinking agents, thermoplastic polymers, moisture scavengers, and UV stabilizers. [0016] In one embodiment, the catalyst is a Tin catalyst. [0017] In one embodiment in accordance with any of the previous embodiments, the filler is selected from organic fillers,